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Chapter Text

Raine scrabbled back into the cave, finally having collected the last of the ingredients for the summoning circle he had been working on. Placing the 11 Tallow Candles in their respective positions as described in the tome, he sighed to himself, having completed the work he began after escaping the bandit sacking of the mage academy two months ago. He had been raised in that academy, abandoned on its doorstep some 22 years ago now, it was all he had ever known. He tried not to think about how the only home he’d ever had had burned down and been looted by a horde of common brigands. Likewise he tried not to think about how the only friends he’d ever had had all been cut down before him as they tried to escape. It was only thanks to his natural affinity for mana storage that he had enough spells to forcibly break out of the besieged complex.

He sat down on a rock in the cave that’d been his home for the past two months. He felt quite nervous about the spell he would soon be casting. Raine hadn’t ever been involved in a summoning before, despite his many years at the academy and intense focus on demonology. Now he was attempting to summon a greater demon in hopes of getting revenge on the remaining bandits that now resided in the half-destroyed halls of his home at the mere level of 17. The Half-Elf sighed to himself, if he was being honest with himself, he was also doing this because of his deep fascination (to the point of nearing obsession) with demonic culture - whether it be their chaotic systems of governance or their complete lack of shame and sexual openness. All of it seemed so much more preferable to the bureaucratic, overly ordered structure of the academy and their draconian rules and outdated views on sexuality down to the very smallest things even for adult students.

Standing back up, Raine sighed, “nothing to do but start the summoning now”. Kneeling down before the circle, he lit the candles with his torch and began chanting, tome open to the page to summon a Succubus. Slowly, energy gathered as his mana depleted and the circle began to glow. The chant ended, and an inky void appeared inside the vibrantly glowing circle. From this darkness rose a large female figure. Raine’s eyes followed the form as the woman rose to her full height. Standing before him, at least 7 feet tall was a very large and very beautiful succubus. Her hair was a shade of deep pink, framed by an impressive pair of black horns that jutted out from the sides of her head, which increased her height to almost 8 feet. She was clad in black leather - wearing only a sleeveless crop top with a sizeable window for her sizeable cleavage; a pair of short shorts that complimented her top and; a pair of large black leather boots. A rapier and a black bullwhip sat on her hips - clearly her weapons.

She opened her eyes and looked down at Raine, who matched her gaze - staring into the red irises that seemed to glow slightly. Her gaze then turned to the circle she was trapped in, analysing it. It was at that time that [Dangersense] warned him that she was likely strong enough to break the circle, given enough time. He looked at the Demon once again, slowly feeling arousal build in him.

[Gained effect: Aphrodisiac Affected Lv1]

He focused on the message, wanting to know more about what he’d just been afflicted with.

[Aphrodisiac Affected (temporary, ongoing) - become 1% more aroused per level. Current Level: 1]

Raine felt relief at the simplicity and weakness of the effect, and the fact it was temporary. It would do him no good to succumb to the Succubus's charms before he could even negotiate any sort of contract. It was at this moment that the Demoness spoke.

“Mortal, I am the Greater Demon Tazamoth Homophagos, state your name and the reason for my summoning.” She said.

“I. uh. Want to form a contract” Raine stuttered in reply, caught off guard by the Demoness, Tazamoth, speaking first.

“Practically all summonings involve a contract, what sort of contract do you want Man-thing. Name your desired terms and we will bargain.” Tazamoth scolded

“Yes. um… I want to form a. A covenant with you.” Raine said, suddenly nervous.

For her part, the Demoness seemed quite taken aback by this admission.

“I’m sorry? You are aware of what that would entail right? You would give over your soul and body to me perpetually, just like that, don’t you have anyone that’d question your sudden disappearance? What could you possibly want in return?” Tazamoth asked, a lot more earnestly.

“I want you to kill the bandits that destroyed my academy. They were the only friends and family I ever had.”

The Demoness cocked her head and raised an eyebrow at that.

“A normal contract where you fed me some mana and then set me loose on the plane afterwards would be more than enough payment for that, Man-thing. Why do you really want to form a perpetual covenant?” She demanded.

“I… In truth, I um. I am obsessed with Demonology. I know what forming a covenant with a Succubus entails, and I. I want that as well.” Raine Confessed, feeling his member engorging as he said the words.

[[Aphrodisiac Affected] increased in level. Level 1 ===> Level 2]

[Attempt to apply [Entranced] on you resisted!]

[Attempt to apply [Heightened Submission] on you resisted!]

Tazamoth smiled, revealing sharp canines and a long wet tongue, taking on a predatory appearance. “Oh, and what does forming a covenant with a succubus entail, exactly Man-thing? Would you care to enlighten me?”

“Uh… um… I will be magically tied to serve you. And you’ll use me as a recharging battery for mana, so you can cast more powerful spells.” Raine stammered, turning red as he continued.

“And you’ll um… fuck me. It’d be like I was your personal sex toy and plaything.” Raine finished, now completely erect.

“Good boy. Oh I can definitely work with you. I’ve needed a covenanter for some time now, as is befitting of a Demon of my status.” Tazamoth said, stepping right up to the edge of the barrier. “Let’s begin forming this covenant then shall we?”.

Her eyes flashed green, and she held out a hand engulfed in unholy flame. Reaching across the barrier, Raine shook her hand, sealing the short man’s fate, and collapsing the seal keeping Tazamoth in. He was then spammed with notifications

[Covenant formation begun]

[Covenant terms are as follows]

[The Half-Elf Raine will swear to eternally serve the Greater Demon Tazamoth]

[The Greater Demon Tazamoth will swear to eternally protect the Half-Elf Raine]

[Raine’s soul shall be bound to Tazamoth’s soul]

[Raine shall refer to Tazamoth as his Mistress]

[Raine shall allow his Mistress to control him]

[Raine shall forfeit all possessions to his Mistress]

[Raine shall allow his Mistress access to his Mana pool]

[Mistress Tazamoth will kill all Bandits residing within Whitcrest Academy]

[These parties will consummate their covenant after this is completed]

[Raine’s class will then change from Adept Mage to Covenanter]

[Raine’s level will then change from 17 to 0]

[Raine’s stats will then be returned to their baseline]

[Lost stats and levels will then be converted to XP and given to Mistress Tazamoth]

[This Covenant cannot be negotiated without both parties' consent]

[[Aphrodisiac Affected] increased in level. Level 2 ===> Level 3]

Raine’s cock twitched as he felt [Aphrodisiac Affected] increase in level. His new Mistress looked down at him as it happened. “Oh, does my good little slut like that? How about I give you a little gift then.” She purred, stepping forward and laying a hand on Raine’s shoulder.

[Tazamoth has just cast [Black Passion] on you!]

[Gained Permanent Effect: Aphrodisiac Affected: Level 1]

Raine focused on this new effect, letting out a slightly shaky breath as he did.

[Aphrodisiac Affected (permanent): become 1% more aroused per level. Stacks with temporary version of this effect. Current Level: 1. Current Cumulative Level: 4].

“We will go and kill those bandits now. I want to consummate our covenant as soon as possible.” Tazamoth commanded.

“Y-Yes mistress Tazamoth.” Raine responded, leading her out of the Cave towards the bandits.

Changes this Chapter:

[Gained Permanent Effect: Aphrodisiac Affected: Level 1]
[Gained Effect: Aphrodisiac Affected: Level 3]

Chapter Text

Ultimately, the battle was very one-sided. The bandits had already taken many casualties when razing the academy, and even though there were still about thirty of them, their levels ranged from about 20 to 25, no match for a level 72 demon, even a less combat focused one such as a Succubus. It had been over in just 20 minutes, various charred corpses once again littered the ruins as Raine sat down next to his Mistress. As he sat, he flicked through his notifications.

[[Aphrodisiac Affected](temporary) increased in level. Level 3 ===> Level 10. Cumulative Level: 11]

[You killed Bandit - Level 21 - +37xp]

[You killed Bandit - Level 20 - +34xp]

Seeing nothing of any real importance, Raine dismissed his notifications, turning to face his Mistress. With [Aphrodisiac Affected] at level 11, just looking at his mistress's scantily clad form was enough to cause an erection. His mistress must have finished looking through her notifications (which must've been much longer) as she turned to him with that predatory gleam in here eyes. Raine felt his face flush red as he imagined her holding him down and having her way with him.

She must've had the same idea as she spoke, "Man-thing - lead me to a bedroom - We will be consummating our covenant now."

Raine stood up, leading her towards the mostly intact hallway of private quarters. They went into the first bedroom along the hallway, he didn't even know whose room it had been, he found that he didn't even care. He needed this.

"Strip." She commanded.

He took off his tunic and trousers, exposing his thin and effeminate body to Tazamoth as she began to take off her shorts.

"Not much body hair. Good, I like boys to be effeminate, it's how they should be. Still, we'll have to make some improvements to make you into a real subservient male like the ones back home" She said.

"What do you mean, Mistress?" Raine asked.

"I come from a nation of hell known as the Matriarchate of Ioketara, there males know their place and do their best to imitate femininity, unlike the Man-things of other nations and other planes." She responded, as Raine took off his underwear.

Raine turned to face his mistress, displaying his cock to her. He had always been insecure about it, as his penis was quite short, just 4.5 inches fully erect. He blamed it on the fact he was a Half-elf and thus sterile - but if the gossip from his now deceased fellow students were true, then these two things weren't correlated. In fact, he was deeply worried now, what if his mistress didn't like how short his cock was? Surely as a 7 foot tall demon it wouldn't be enough for her.

"Aw. How cute, the pathetic little Man-thing has a pathetic little penis. I can see why you wanted to enter into a covenant with me, you were practically made to be dominated, to be feminised, to be mine." She purred. "I will mold you into a proper plaything."

With that, she advanced on him, grabbing his wrists in her hands and hoisting them above his head. She pushed him down onto the bed, keeping one hand restraining his arms, whilst the other toyed with his penis, a bead of precum forming as she stroked it. Her large breasts, E cups most likely, still held within her top were just centimetres from his face, and he longed to reach out and grab them. But his mistress hadn't given him permission to do that, and his arms were held above his head anyhow. Still massaging his cock, she lent in close to his face and planted a kiss on his lips, her long saliva-coated tongue sliding into his mouth as he tried to let out a moan.

[Your Mistress, Tazamoth, has used [Succubus Kiss] against you.]

[Gained Permanent Effect: Body Sensitivity Lv1]

[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Afflicted] increased in level. Level 10 ===> Level 13. Cumulative Level: 14]

Raine didn't need to look at the new Permanent Effect's description to figure out what it did. Every movement of his Mistress's hand over his penis felt just that little bit more explosive. Her tongue continued its way into his mouth, hitting the back of his mouth and sliding downwards into his throat, trailing saliva with it. Raine gagged around it and his Mistress shushed him. After what seemed like an eternity, she finally withdrew with a whispered "Good boy."

She stopped stroking his penis and moved to straddle him, sticking a finger in her covenanter's mouth which he dutifully sucked on. She withdrew the hand that had pinned his arms above his head, chosing instead to grab his jaw with it. The other hand returned to his penis, grabbing it. She then lowered herself onto the diminutive member, letting out a soft moan as she did so. Raine himself felt as though he might explode from the pleasure as her slick cunt met the base of his shaft. He let out another moan as she began to grind against him, her hips undulating against him causing him to twitch in erotic pleasure. She moved her hands back to his face, embracing it and forcing him into another [Succubus Kiss] that Raine greedily let into his mouth.

[Your Mistress, Tazamoth, has used [Succubus Kiss] against you.]

[[Body Sensitivity](permanent) has increased in level. Level 1 ===> Level 2].

In his pleasure-filled haze, Raine started to feel as if something was being drained from him. His mistress continued to grind against him, moaning as she did so. Soon, he couldn't hold it in anymore and with a groan Raine came in his mistress. The pleasure was unlike anything he'd ever felt before, even masturbating couldn't compare with the sheer pleasure of the succubus-induced orgasm. Tazamoth smiled as his seed spurted into her. She lifted herself off his small shaft, semen dripping from her pussy onto Raine's stomach as he smiled daftly.

[A [Succubus] brought you to orgasm! [Body Sensitivity] increased in level. Level 2 ==> Level 3]

"Good little Man-thing... I've fulfilled my part of the covenant now, but I'm yet to come, and I don't think your cute little cocklet will be roused for a while. I think it's time for you to taste your Mistress." she said almost hypnotically as she positioned her pussy in Raine's face.

Raine complied enthusiastically as she thrust her cunt into his face, tonguing her perfect pussy as she rode his face, eliciting another moan from the Demoness. Encouraged by her lustful vocalisations, Raine continued to use his tongue to pleasure her. She ground on his face and murmured encouraging words to him as he ate her out until her grinding became less controlled and she breathed out a shaky "fuck, I'm coming."

[Ingested Aphrodisiac Fluids (Vaginal fluids). [Aphrodisiac Afflicted] increased in level. Level 13 ===> Level 16. Cumulative Level: 17]

[Covenant Consummated, enacting changes...]

Raine felt dizzy as the draining sensation returned. His mistress lifted herself off of his face and lay down next to him.

[Level decreased! Level 17 ===> Level 0]

[HP decreased! 56 ===> 20]
[MP decreased! 37 ===> 10]
[All Attributes decreased to 10!]
[Class Changed! Adept Mage ===> Covenanter]
[Converting losses into XP]
[Transferring XP to Mistress Tazamoth]
[Binding Soul in service of Mistress Tazamoth]

As the notifications rapidly piled up, Raine felt amazing. Even as his stats fell, the joy of being bound to Mistress Tazamoth was immense. He turned his head to look over at his Mistress, thanks to his lowered [Wisdom] and [Intelligence] atributes, he could feel the effects of her demonic aura even more strongly than before.

[Attempt to apply [Aphrodisiac Affected] on you has failed! Reason: Trait applying the effect not strong enough to increase further!]

[Gained effect: Entranced]

[Gained effect: Heightened Submission]

'Oh', thought Raine, that must be because of my lower stats. He focused on [Entranced] to find out its effects.

[[Entranced](temporary, ongoing) - You gain disadvantage on [Intelligence] and [Wisdom] Saving Throws. +1% Arousal per level if a sapient you've had sex with is in Line of Sight. Current Level: 1]

Raine found it to be not too dissimilar to [Aphrodisiac Affected], so he moved onto the next effect, [Heightened Submission].

[[Heightened Submission](temporary, ongoing) - You feel compelled to complete orders given to you by faction members of a higher rank. Orders become 1% harder to ignore per level. Current Level: 1]

Raine thought that this one was perhaps a bit redundant, given his covenant already had him obeying Mistress Tazamoth's orders. So he decided to move onto his core character info as a whole.

It seemed that all his stats really had been returned to their baseline. Though he evidently still had his one Trait [Slight] which buffed his Agility at the cost of his Strength and Vitality. Exhausted from the stat drain and the sex, Raine quickly fell asleep next to his mistress, still covered in a mix of their fluids.

-----------

Changes in this chapter:

[Gained Permanent Effect: Body Sensitivity: Level 3]

[Gained Effect: Entranced: Level 1]

[Gained Effect: Heightened Submission: Level 1]

[Effect Increased: Aphrodisiac Affected: Level 3 ===> Level 16. Cumulative Level: 17]

Chapter Text

Raine awoke some time later. It appeared his mistress had left him in the room. Not knowing when she'd be back, he decided to check through his notifications.

[Trait Gained: [Covenant Bond (Covenanter)]]

[Effect Lost: Entranced]

[Effect Lost: Heightened Submission]

[Effect Diminished: Aphrodisiac Affected. Level 16 ===> Level 15. Cumulative Level: 16]

It seemed as though the temporary effects decreased a level every time he slept. Their was also the new Trait that he had gained, [Covenant Bond (Covenanter)]. Focusing on it, he read its description.

[[Covenant Bond (Covenanter)] - You are bonded to a Demon via covenant. You can see their HP, MP and level, and in return they will sustain you. You will feel compelled to follow their orders.]

Interesting, though Raine would have to wait until Mistress Tazamoth returned and gave him orders to see just what that meant, and what it felt like. His mind went back to what had happened last night, he could scarcely believe that it had happened. If it weren't for his new class and his bond, Raine would've written it off as a dream or something. He felt a warm feeling wash over him as he remembered his Mistress's embrace, and the way she ground against him. The summoning had gone better than he ever could've imagined or hoped. He hoped that when she returned from wherever she had gone, that she would continue to use him like that. He hoped she used him in ways she hadn't yet. Damn, he was horny. He felt his cock getting hard even now, just fantasising about last night. His mistress certainly had many plans for him, sexually and magically. As a lover of both, it excited him.

He stood up, taking stock of the room he was in. Aside from the double bed, there was also a dresser, a wardrobe and a couple shelves. Atop the shelves were various magic books, mostly dealing with restoration magics. Raine had dabbled in restoration during his studies, learning the spell [Minor Cure] during this time. However, he hadn't felt the need to take his study further and decided to focus primarily on demonology. Whoever lived in this room prior to the bandit attack had obviously been a healer of some sort though. A couple of the other books covered other schools of magic - one on cryomancy, one on transformation and another on alchemy. Alchemy did interest Raine, though he had sadly never gotten to study it. Perhaps in the future he would be able to.

He turned his attention to the dresser. It had 4 drawers. Going through them all he found were men's clothes in sizes too large for him. With that he moved onto the wardrobe. In the wardrobe were various coats, cloaks and even a pair of boots (once again all too large for him) but what there also was, hidden beneath a folded up cloak, was a lockbox. [Dangersense] didn't detect any traps, so he tried to open it. Unfortunately it was locked. The key for the box wasn't in the wardrobe - at least not that he could find - so he turned his attention back to the dresser. Despite chucking clothes out of the dresser, he couldn't find any sort of key in the piece of furniture. Sitting back down on the bed he pondered his next move. He realised now that he was still naked and covered in a mixture of his own and his mistress's juices, and that he probably shouldn't have been handling the books like that. The academy always taught students to not touch any book when even slightly dirty, and never to touch another persons books at all. Then he realised, no one in the academy would touch the books.

He stood back up, moving over to the books, taking the first one down from the shelf and flicking through it, nothing inside. The next one, the same. So was the third and the fourth. The fifth book however, had several pages stuck together as he flipped through it. Stopping, he took a closer look, opening the book to the first of the stuck pages. Sat there, in a carved out divot was a small brass key. Grabbing it, he ran back over to the lockbox and unlocked it. Raine opened the lid to find a book inside, facing down. Taking it out and flipping it over, he saw that it was a demonology book - specifically one named 'The Traits and Effects of Hell on Humans' - Raine remembered that the Masters of the Academy had investigated a stolen book from the Master library just a few months before the academy fell, interrogating all of the Journeyman and Apprentice Demonology students including himself - obviously this must've been the book stolen, and to end up in a restoration student's room was very strange. Looking back into the lockbox, Raine discovered various notes, written by the student. They wove a story of a student trying to figure out how to apply the effects from the books to others.

'Book mentions effects transferred by aura. Maybe check out books on illusion and spirituality from Library?'

'Some references to alchemical solutions in effects. Warrants further investigation'

'Perhaps should summon lesser demon to form contract for knowledge. but where?'

Raine shook his head, whoever this student was, he was in far too deep and barely seemed to have a basic understanding of demonology. It was pretty clear he'd made no breakthroughs at all. It was also pretty clear what his motives were.

'Finding way to control living sapients would greatly reduce cost of creating army. Potential replacement for undead?'

It seemed this student was a dark artist and wannabe necromancer. Raine figured he wouldn't have to worry about that though as he had almost certainly died at the hands of the bandits. What interested him much more was the Master-only book on Demonology sat right in front of him. This would be a great opportunity to learn more. Opening the book, he began to read it. The first section was mostly a preamble extolling the dangers of demonology, and urging readers without familiarity with demons to put the book down. Raine figured himself to have gotten pretty familiar with Demons last night, so carried on. Following that was a brief introduction, covering what lead up to the writing of the book. Apparently several humans had been captured after a group of knights had banished a handful of demons. The captured humans, believed to be in covenant with the demons, had been held long enough that some of their character information had been revealed, which was generally considered taboo and in some cases, even illegal - no wonder it was in the master section. It turns out they eventually killed themselves - though the mages investigating weren't able to locate their souls after they did so and some speculated that they had been returned to their masters. Given the existence of his Trait [Covenant Bond (Covenanter)], Raine considered that speculation pretty much confirmed. Following this, there was a list of the most commonly found effects on the humans, accompanied by brief descriptions of each effect. Of the effects, a handful were found on all 7 captured humans.

'[Body Sensitivity] was found on all 2 males and 5 females in the study. This effect was found to be permanent, and across the board the level of this effect was high, ranging from 67 to on one female (dubbed F3) 300. It evidently affected the sensitivity of the afflicted to most physical stimuli, all subjects experienced sexual gratification from all but the slightest of touches.' 

Raine could feel the effects of [Body Sensitivity] at just level 3. The thought of that level hitting 300 made him shiver with anticipation. He carried on reading.

'[Aphrodisiac Affected] was another effect found on all subjects in the study. This effect was found to have both permanent and temporary versions in the subjects. This affliction is well known in demonology, and most Greater Demons do seem to be able to afflict it to those nearby, either through spells or their aura. Unlike in demonologists, where the affliction rarely exceeds the level 20, in these humans, all of them had a permanent level of at least 54, with most having a permanent level of 100 - suggesting some sort of cap on the ability of demons to inflict this effect. Once again however, F3 had a higher level than the other subjects, having a permanent level of 150. The level of temporary effects were even higher. Ranging from Level 187 in F5 to Level 398 in F3. This effect is known to increase arousal of the afflicted by 1% per level. F3 then, had a heightened arousal by 548%. It should be noted that the subjects had to be separated to prevent attempts of sexual intercourse with each other.

Raine was once again familiar with this effect, currently sat at 1 permanent level and 15 temporary levels. He hoped to increase that soon.

'[Sex addiction] was found on all subjects in the study as well. This effect was permanent in all subjects. Generally in humans it is extremely rare naturally, and rarely exceeds the level of 10. In all subjects this was found to be level 50, suggesting a cap on the ability of demons to inflict this effect. When questioned, subject M1 revealed he first obtained this effect after engaging in intercourse with his master 10 times in one day. It is unclear if this is the most common way of getting this effect or if there are other ways. Subject M1 refused to testify any further. This effect encourages the afflicted to have sex more frequently, though the exact mechanism by which it does is unknown.'

Raine had heard of this effect, having read of it in some of his studies about the accounts of survivors of Succubus encounters. 

'[Heightened Submission] was the fourth effect found on all subjects. All had a temporary version of the effect, whilst all but M1 had a permanent version as well. Unfortunately all subjects expired before the exact levels were uncovered. It is known that of those with a permanent version of the effect, F2 had a level between 1 and 9; M2, F1, F4 had a level between 10 and 49; F5 had a level between 50 and 99 and; F3 had a level of 100 or higher. Subjects did not display significant submission towards researchers and so the exact effects of [Heightened Submission] are unknown. It is theorised at this time that it may be specific to individuals.'

Raine turned the page. It seems as though these researchers really hadn't gotten that far before the covenanters had expired. Several entries were listed below.

'[Breast Expansion] was found on all female subjects. This effect was permanent in all subjects. Levels ranged from Level 10 in F2 to Level 120 in F3. Exact effects unknown, but it is understood that it increases breast size.'

'[Oral Addiction] was found on 3 subjects - M1, F2 and F4. This effect was permanent in all subjects. Levels ranged from Level 9 in M1 to Level 98 in F4. Effects unknown, theorised to encourage oral sex. May develop into [Oral Obsession] found in subjects M2, F1 and F5.' 

'[Oral Obsession] was found on another 3 subjects - M2, F1 and F5. This effect was permanent in all subjects. Levels ranged from Level 12 in M2 to Level 33 in F5. Effects unknown, theorised to greatly encourage oral sex.'

'[Vaginal Addiction] was found on 2 subjects - F2 and F4. This effect was permanent in all subjects. Levels discovered were 93 and 97 respectively. Effects unknown, theorised to encourage vaginal sex. Likely develops into [Vaginal Obsession] found in subjects F1 and F5.'

'[Vaginal Obsession] was found on 2 subjects - F1 and F5. This effect was permanent in all subjects. Levels discovered were 13 and 33 respectively. Effects unknown, theorised to greatly encourage vaginal sex. May develop into [Vaginal Mania] found in subject F3.'

'[Vaginal Mania] was found in only 1 subject - F3. This effect is believed to be permanent. The level was not uncovered before subject expired. Effects unknown, theorised to greatly encourage any kind of vaginal stimulation. Existence suggests the existence of [Oral Mania], which F3 may also have possessed but wasn't identified during research due to premature expiration of the subject.'

'[Semen Hungry] was found in 2 subjects - M2 and F3. Nothing else is known about this effect as it was discovered shortly before expiry of these two subjects. Given that 2 subjects had already expired prior to its discovery, it is possible that it was present in more of them. Effects are unknown.'

Raine went to turn the page. Despite its rather dry manner of wording things, it was turning Raine on, and he felt himself flush slightly. Then, there was the sound of boots on stone, and the door opened. Raine spun around and saw his mistress. Seeing he was awake, she grinned at him, licking her lips with her slimy tongue. His covenant bond supplied him with her level - 74, it seems his guess at her being about level 70 had been right.

"I see my good little Man-thing is awake. I sensed a demonic artefact was nearby when I woke up and just had to investigate. Did you know the academy had a Demon Lordship's scrying ball in one of their vaults?" She inquired.

Raine shook his head.

"Hmm, well then it was just a matter of good fortune then. This ball will greatly improve the efficiency of my spells. I will be bringing it home with me when we return." She stated.

"Home, Mistress?" Raine asked confused.

"Well yes, whilst it is a shame that I can't stay in the Middle plane and level up, staying in the Middle Plane with a new covenanter is just asking for some archmage to come and break the covenant whilst its still weak. I plan on us returning to hell so we can strengthen our bond and I can prepare for a much longer and more successful expedition." She explained.

"Oh, right. What's it like in Ioketara? I read in my character info that that is our faction." He asked again.

"Ioketara is a land of red stones, I'm sure you've seen it's a Matriarchy. Male or other masculine demons are expelled from the region, whilst foreign demonesses have unrestricted access to joining it - though there are no similar restrictions on non-demon males. It's lead by Matriarch Ioketoth, a daughter of Lilith. It's highly urban, though my personal domain is in a more sparse location for I intend to create to create my own town when I reach Ladyship at Level 100." She explained, before continuing "Speaking of other demonesses, they'd try and snatch you up as you are now, without any markers of being mine. Why don't we fix that?"

Mistress Tazamoth strode up to Raine, pinning him against the wall.

[Attempt to Apply [Aphrodisiac Affected] on you has failed! Reason: Trait applying the effect not strong enough to increase further! Cap: Level 10]

[Gained Effect: Entranced]

[Gained Effect: Heightened Submission]

She licked his chest, trailing saliva up it and onto his neck as he shuddered in anticipation.

[You have come into contact with Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] cannot be raised any higher by these fluids through contact alone! Cap: Level 15]

Then, halfway up his neck, she paused, a rapacious look in her eyes as she got closer to it. Raine felt her hot breath against his throat and then the pain of her teeth sinking into his neck.

[Your Mistress, Tazamoth, has used [Foolish Bite] against you.]
[Critical Hit!]
[You took 2d8 piercing damage]
[Rolling]
[Rolled: 5, 2]
[You lost 7 HP!]

[Beginning Hard Wisdom Save with Disadvantage (Entranced)]
[Minimum saving roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling]
[Rolled: 13, 9]
[Hard Wisdom Save Failed!]
[You have gained 2 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity](Permanent) increased in level. Level 3 ===> Level 5]

Raine shuddered as his Mistress withdrew, holding a hand up to his throat as it bled lazily.

"There. Much better my little Raine. Now my peers will know you're mine until we can get a better solution." She said soothingly. "Now come here and give your mistress a kiss."

"Yes Mistress" he obediently replied as he walked into her embrace. Almost immediately, her lips pressed against his, and he felt her long tongue work its way past his own and down his throat.

[Your Mistress, Tazamoth, has used [Succubus Kiss] against you.]

[[Body Sensitivity](Permanent) increased in level. Level 5 ==> Level 6]

[You have ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 15 ===> Level 18. Cumulative Level: 19]

His mistress withdrew her tongue, and looked down at Raine's hard penis, which now pressed against her thighs, smearing them with precum. 

"Yesterday I was too generous, letting you cum first, and inside me. This time, you're going to make me cum before I so much as even touch your pathetic little dick." She said cruelly.

"Yes mistress" Raine replied.

The two moved to the bed, where Tazamoth wasted no time in once again discarding her shorts and boots, before pulling Raine in to her crotch. Dutifully, Raine began to pleasure her with his tongue like he had last night. He realised now how the covenant bond's orders worked, now feeling as though the idea of him cumming right now would be disrespectful, perhaps even shameful - no matter how much he wanted it. Instead he focused on lapping at his mistress's pussy, hoping to bring her to orgasm.

[You have ingested Aphrodisiac Fluids (Vaginal Fluids). [Aphrodisiac Affected] increased in level. Level 18 ===> Level 21. Cumulative level: 22].

He continued to lick hungrily until his Mistress came. Her thighs pressed around his head as she did so.

[You have brought your master to Orgasm. +10 XP]

Raine blinked in surprise, he hadn't known that Covenanters could gain XP like that. Though he supposed it made sense since humans sighted alongside demons were often of a high level.

His mistress sat up. "Good boy Raine. I think I'll reward you now" She said.

She pushed him onto his back, mounting him with her wet cunt. Her eyes flashed green as she cast a spell on him as his penis entered her.

[Your Mistress, Tazamoth, has cast [Black Passion] on you!]
[[Aphrodisiac Affected](permanent) increased in level. Level 1 ===> Level 2. Cumulative Level: 23]

[You have come into contact with Aphrodisiac Fluids (Vaginal Fluids). [Aphrodisiac Affected] cannot be raised any higher by these fluids through contact alone! Cap: Level 15]

Mistress Tazamoth bounced and ground on his dick causing him to moan in pleasure, [Aphrodisiac Affected] and [Body Sensitivity] causing him to flinch from the sheer pleasure. Already after just a few seconds he felt himself nearing orgasm. He bucked slightly under his mistress, the Demoness' size making it difficult to move underneath her. As he watched her fuck him, he felt himself falling deeper under her control.

[Attempt to Apply [Aphrodisiac Affected] on you has failed! Reason: Trait applying the effect not strong enough to increase further! Cap: Level 10]

[[Entranced] increased in level. Level 1 ===> Level 2]

[[Heightened Submission] increased in level. Level 1 ===> Level 2]

Then his mistress got off of him. Shooting her a look of betrayal, got her to raise an eyebrow at him.

"Oh, did you think eating me out once was enough to earn you a chance to cum in me? How greedy. I was going to finish you off with my hands, but now I'm not sure you deserve even that. Hm." She declared haughtily

"Please Mistress, I need to cum!" Raine begged.

"Maybe you can convince me to help you finish if you ask nicely" She stated

"Please Mistress Tazamoth, this pathetic one would like you to make him cum with your hands. I am sorry I insulted your generosity." He pleaded with an edge of desperation

"Much better! See little Raine, that wasn't so hard was it? Of course I can help you cum from your needy little dick" she purred soothingly, reaching down to grab his glistening shaft.

She began to slowly stroke his cock, each stroke eliciting a small jerk or moan from Raine. She spat into her hands, the thick saliva helping to lubricate his penis more as she began to use both hands, rotating opposite directions, still moving oh so slowly. She had that hungry smile on her face she seemed to get often during sexual intercourse, it made Raine feel like he was just a morsel of food to her, and gods did that only make him harder. Her lower hand moved down to play with his balls, squeezing them sensually right up until they started to hurt, driving Raine insane. He slipped even further into her command.

[[Entranced] increased in level. Level 2 ===> Level 3]

[[Heightened Submission] increased in level. Level 2 ===> Level 3]

"Mistress, I'm going to cum" He moaned.

"Go on my little man-thing" She permitted, as she returned her other hand to his shaft and began to stroke faster and faster, reducing Raine's mind and focus to only his penis and her hands stroking it. He felt himself buck once more, and then he watched blissfully as semen spurted out of his penis, landing on his stomach and coating his shaft and his mistress's hands.

[A [Succubus] brought you to orgasm! [Body Sensitivity] has increased in level. Level 6 ===> Level 7]

Tazamoth licked the cum off of her fingers and stood up.

"Good boy." She said slowly, "When I bring you back home we can begin your training proper."

At that, an exhausted Raine shivered with expectation.

-----------

Changes in this chapter:

[Gained Effect: Entranced: Level 3]

[Gained Effect: Heightened Submission: Level 3]

[Permanent Effect Increased: Body Sensitivity: Level 3 ===> Level 7]

[Permanent Effect Increased: Aphrodisiac Affected: Level 1 ===> Level 2]

[Effect Increased: Aphrodisiac Affected: Level 16 ===> Level 21]

Chapter Text

Raine sat up after a minute, no longer feeling quite so tired. Since entering into the covenant, Raine had felt less energetic - probably an effect of the lost attributes. If the small window in the room was anything to go by, it was currently the early evening. Mistress Tazamoth also sat up, getting her shorts and boots back on. She scanned around the room, catching sight of the opened lockbox and the half-read demonology book, before looking back at Raine. 

"Been reading ahead have we?" She teased

"I... uh... yeah" Raine said

"Well we can't have that. No spoilers for you." She said smugly, as the book disappeared right in front of Raine's eyes, giving him a bit of a shock. Looking up at her, he saw her eyes fading from green to red.

"Spatial magic." He said more than asked

"Yes, most Greater demons develop some sort of spatial magic to help them store items found in Middleplane until they get back to Hell." Tazamoth confirmed. 

"Speaking of, we'll be going back to hell shortly. We'll go back to where you summoned me, since the spell to return will be much cheaper where the veil between planes has already been pierced." She continued.

Raine felt slightly worried at the thought of having to walk back to that cave, the hike was nothing to sneeze at.

"I will carry you there, Little Raine." Tazamoth offered, seemingly seeing his concern.

Just like that, Raine found himself being princess-carried out of the room, and through the half collapsed halls of the academy.

"Thank you mistress" Raine said after the shock of being picked up as if he were no heavier than a plate of food or stack of books wore off.

Tazamoth placed a gentle kiss on his forehead in response.

As they began their hike through the forest, up the gentle slope that led to the Cave, Raine realised he hadn't yet taken a look at the additional information. So he decided that whilst he was being carried he might as well see if anything had changed.

There were several changes that he spotted immediately. Firstly, the Levels until class change had changed to 1. This kind of made sense, as generally most people gained a class at level 1, after pushing past level 0 - though Raine didn't know enough to think about what the class change could be. The next one he noticed was the 'Levels until Subspecies Change' which had gone from 83 to 26, meaning instead of reaching the 'Lesser Immortal' subspecies at level 100, he'd instead reach a new subspecies at level 25. Raine was a little less confident about this one, sure subspecies changes were known to correspond to a pretty large increase in power, and getting that sooner would be pretty great (especially since most people died before reaching level 100), the Lesser Immortal Subspecies most humanoid sapients had access to was particularly powerful. Still, he'd cross that bridge when he got to it. The next two changes were more minor and a lot less intimidating. Whereas previously his profession had been [Arcane Student], and his Alignment had been [Neutral](Leaning Chaos), it made sense that the destruction of the academy and his new covenant had left him without a profession and had tipped him across into chaos.

Deciding just to lie in his Mistress's arms and meditate, he dismissed the information and closed his eyes.

[Short Rest: Healing 1d4 HP]
[Rolling]
[Rolled: 3]
[HP increased: 13/20 ===> 16/20]

Waking up from his impromptu nap as Mistress Tazamoth set him down, Raine saw that he was back in the cave he had summoned her in. He'd been set on a relatively smooth part of the cave floor, just a couple metres away from the remains of the summoning circles. Looking outside revealed that it was almost night, the last pink slivers of sunlight clinging on desperately to the horizon. Mistress Tazamoth noticed he was awake then.

"Ah, good timing. I was just probing the circle to see how malleable the space was. Looks like it won't be the easiest jump, but it'll only be difficult enough to make it tiring, rather than dangerous." She said.

Raine only nodded.

"Now come, stand in the circle my good little boy." She demanded "I'll be using your mana to supplement my own part of the spell, so I can recover mine quicker for what I have planned for you soon. You'll probably feel quite tired when we get back, as will I, so we'll be sleeping in my bed when we get in, now stay still." she continued.

Raine stood stock still, as he watched his Mistress's eyes flash green.

[Your Mistress, Tazamoth, is siphoning your mana!]
[10 MP lost!]

Then, there was a falling sensation for just a split second and then they were in a large bedroom. The sudden falling feeling left Raine feeling quite green as he landed in what was presumably his mistress's bedroom. The first thing he noticed was the temperature, although it wasn't scorching like some liked to depict hell as, it was definitely warmer than his home in the Academy had been. If he had to guess, he'd say the temperature was about 25°C, and the air was a lot drier than the academy. Next, he looked around the room, a dark wooden floor underfoot, with a King-sized canopy bed seemingly made of the same dark metal that his Mistress's sword was made of, adorned with crimson bedding and curtains. To the right, several wooden drawers and dressers were lined against the right side wall. Opposite the bed, a map of what appeared to be the Matriarchate of Ioketara was on the wall, flanked on either side by a window. Finally, on the left wall was a large dark metal door that reminded Raine of the vault doors of the Academy. It honestly looked so heavy that he'd struggle to open it - which was honestly kind of pathetic of him (though he seemed to enjoy being pathetic as of recent, so maybe that wasn't such a bad thing). Overhead was a chandelier made of that ever-present dark metal, the candles atop it didn't seem to actually be dripping wax, and [Dangersense] told him there was some complex, but mostly harmless, magic on the thing.

Then he felt the tiredness that mana loss caused as a wave of fatigue crashed over him. He felt a guiding hand from Tazamoth against his back, slowly herding him towards the bed, which he crashed onto immediately. His mistress lay down next to him, stripping off her own clothes. It occurred to him that he'd never seen his mistress topless before as she lifted the leather top off of her, revealing nearly impossibly perky tits featuring simple metallic nipple piercings. Raine blushed slightly when his mistress noticed him staring, before leaning in to kiss him. Once more, he felt her long tongue enter his throat as he once again got a notification.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level. Level 7 ===> Level 8]
[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 21 ===> Level 24. Cumulative Level: 26]

He felt his mistress withdraw from the kiss and then he was out like a light.

-----------

Changes this Chapter:

[Permanent Effect Increased: Body Sensitivity: Level 7 ===> Level 8]

[Effect Increased: Aphrodisiac Affected: Level 21 ===> Level 24. Cumulative Level 26]

Chapter Text

Raine's POV:

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 5]
[HP increased: 16/20 ===> 20/20]
[Rolling]
[Rolled: 2]
[MP increased: 0/10 ===> 2/10]

[Effect Diminished: Aphrodisiac Affected: Level 24 ===> Level 23]

[Effect Diminished: Entranced: Level 3 ===> Level 2]

[Effect Diminished: Heightened Submission: Level 3 ===> Level 2]

Raine awoke, initially wondering where exactly he was. He didn't sleep in a Canopy bed. Then, he remembered being taken back to his Mistress's domain in hell. The memory of being carried to the summoning circle and then guided to the bed flooded back into his mind. Slowly, so as not to wake his still sleeping mistress, he worked his way off of the bed. He looked around to try and find his clothes, only to realise that he was naked when he was brought back to hell. That probably constituted an issue, but he was sure his Mistress had some clothes for him to wear somewhere. Putting that aside for a moment, he decided to look out the windows - he hadn't gotten a clean look last night. Did hell have nights? Looking outside revealed a landscape of ash interspersed with active volcanoes and lava flows, occasional red boulders dotted the landscape. Which seemed fitting for hell even if it wasn't as sweltering as its name would suggest. A couple times, he thought he could see figures moving about in the distance.

Now that he was less tired, he realised just how different Hell was from Middleplane. Everything seemed more malleable here, as if casting a spell would be so much easier, as if the world wanted him to cast spells. Looking outside he could sense how the mana of the environment shifted and swirled, changing like the dunes of ash that made up the landscape physically. 

He kept staring out of the window until his Mistress woke up. He heard her get up from the bed and slowly step towards him. He could feel his cock getting harder at just the thought of her. He felt her grab his waist, pulling him in closer to her. He turned his head up to look at her, and was greeted with a kiss on the lips. His mouth opened obediently and his Mistress's long slimy tongue slipped into his mouth and then his throat as he moaned around it.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level. Level 8 ===> Level 9]
[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 23 ===> Level 26. Cumulative Level: 28]

"Come on little Raine, back to bed, it's time to serve your mistress."

Raine complied immediately, walking back to the bed and sitting down on top of it. His mistress climbed onto the bed as well, drawing the scarlet curtains of the bed shut. She turned to look at him ravenously.

"I need to go out and buy you some things today to help with your training, but I can start it now - teach you some lessons before I go out. I know you're eager to learn about demons, especially their more sexual habits, since I caught you reading that book." She began.

Raine flushed slightly, his mistress teasing him making him even more aroused. A drop of precum dripped down onto the sheets.

"So, my first lesson is that Demons have much more mouldable bodies than Middleplane sapients such as yourself." she said as she grinned.

Her eyes turned green, as she underwent some sort of magical process. At first, Raine didn't notice anything. Then he saw his mistress's clit growing, expanding in length and girth. Her vagina began to shrink and close up, before the flesh started expanding outwards, swelling in size and wrinkling somewhat. Realisation dawned on Raine's face. The transformation finished, Mistress Tazamoth's eyes no longer glowing. There, before Tazamoth's eyes was a huge penis and large, virile balls. The penis must've been about 8 inches in length, with a circumference of 6 inches as well. Raine stared at it in shock as precum dribbled from its tip.

"A dick?" Raine said in shock

"Yes, very perceptive. I know I said that Ioketara expels non-females, but for demons sex has little to do with gender, and since we're so malleable physically, being non-female is a choice. As a Greater Demoness, I'm able to shift my shape a fair bit more than the average lesser demoness. And whilst I find males to be pathetic, I can acknowledge they have the better tool for training Middleplaners like you. Besides, mine's bigger than most pathetic males. Like yours. I hope you like cock, little Raine, because you're going to be sucking it." His mistress said evilly.

"I-I... do actually. Like dick that is. I'm bisexual." Raine replied flustered.

"Good boy, that'll make training much easier. Now, open wide."

[[Entranced] increased in level. Level 2 ===> Level 3]

[[Heightened Submission] increased in level. Level 2 ===> Level 3]

[You have ingested Aphrodisiac Fluids (Precum). [Aphrodisiac Affliction](temporary) increased in level. Level 26 ===> Level 29. Cumulative level: 31]

Mistress Tazamoth's cock hit the back of his throat hard and Raine gagged, tears welling up in his eyes as he got a rough facefucking from his Mistress's mighty she-cock. Her fat nuts slapped against his chin as she thrust in and out of his mouth. He felt utterly emasculated as his mistress's girthy cock plunged into his mouth once more, thoughts of his own cock and sterile balls being dwarfed in comparison only serving to make him harder. 

He looked up at his mistress, who was smiling salaciously as she pumped her cock down his throat. Seeing him looking up at her, she spat on his face.

 "Yeah. You like that you pathetic little man-slut? I bet you do. You're my bitch do you understand?" She practically roared.

Raine struggled to nod around a mouthful of cock, but Mistress Tazamoth got the message. He felt like he was going to cum right now and he hadn't even touched his penis. Perhaps he should, he thought, one hand reaching down to furiously tug at his diminutive cock. Before long he felt his hips twitching, and he came hard, cock still in his mouth. His semen spurted out, landing on the bed before his mistress.

[A [succubus] has brought you to orgasm! Body Sensitivity has increased in level. Level 8 ===> Level 9]

"God's how pathetic, the little man-thing can't even stop himself from cumming just whilst having his face-fucked." His mistress spat out.

Even though he was no longer hard, Raine kept stroking his cock, as though it were an obsession. Then he felt his mistress's movements become less controlled, more jerky and he braced himself. She grabbed his head and pulled him hard into her crotch, he felt thick spurts of semen coat the back of his throat and he gagged around the still shooting she-cock. Finally his mistress's pulled back, and he could breathe.

[You have brought your Mistress to orgasm. +10XP]

[You swallowed Demon Semen! +1XP]

[You have reached Level 1!]

[You have ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] has leveled up. Level 29 ===> Level 30 (cap)]

His mistress's cock went flaccid, shrinking down to 5 inches in length, which hung proudly between her legs. Even limp she was bigger than him and he loved how that made him feel.

[[Entranced] increased in level. Level 3 ===> Level 4]

[[Heightened Submission] increased in level. Level 3 ===> Level 4]

-----------

Tazamoth's POV:

Having given her Raine a good throat-fucking, Tazamoth felt deeply satisfied - watching his cute pointy ears twitch as she released her load in him was adorable, she was tempted to do it again. Unfortunately, there were other matters for her to attend to.

[Your covenanter, Raine, has reached level 1.]
[Select a class change for your covenanter: [Covenant Warrior], [Covenant Thief], [Covenant Mage]]

How exciting. She got to choose ascensions for her little Raine? Sadly there really wasn't much choice in this one - Raine had been a mage previously, and she doubted he'd enjoy being a warrior or a thief, and he probably wouldn't be any good at them either.

"You were a good boy Little Raine." She soothed the spent Half-Elf. "Well done on levelling up. It says here I can choose your class. You want to remain a mage right, rather than a warrior or a thief?"

The male nodded weakly.

[You have selected [Covenant Mage]]
[Applying changes]
[Raine gained 1 HP and 3 MP!]

[Select a new trait for your covenanter based on their prior experiences: [No Gag Reflex], [Swallower], [Submissive], [Weak to Aphrodisiacs], [Virile]]

[[No Gag Reflex] - The covenanter has lost their Gag Reflex, they will be able to deepthroat most things without worry of choking, allowing them to suck dick faster.]
[[Swallower] - The covenanter gains double XP for consuming Semen]
[[Submissive] - The covenanter becomes more submissive. The Effect [Heightened Submission] doubles in strength.]
[[Weak to Aphrodisiacs] - The covenanter has become weak to Aphrodisiacs. The Effect [Aphrodisiac Affected] doubles in strength. Once a week, levels of [Aphrodisiac Affected](temporary) will be converted to [Aphrodisiac Affected](permament) at a ratio of 20:1. A maximum of 100 levels of [Aphrodisiac Affected](temporary) may be converted at any one time.]
[[Virile] - The covenanter's penis and testicles enlarge by 50%. The covenanter becomes 50% more fertile.]

Tazamoth stopped and read through the available traits. She'd heard off of other demonesses that covenanter level 1 traits were generally pretty bad, but she hadn't realised how bad it really was. [No Gag Reflex] had no effect and basically just acted as a skip for something she was planning to train into him anyway. [Swallower] wasn't too bad, if a bit basic. [Submissive] was much the same. [Weak to Aphrodisiacs] seemed to be an alright option, it would help her to build up her Raine's arousal levels much quicker. Then there was [Virile] which was an utterly useless trait in her opinion, no covenanter of hers would have a large penis, small cocks were much cuter and befitting of a male. Besides as a Half-Elf, Raine was sterile, the increased fertility would mean nothing to him. Decision made, she selected [Weak to Aphrodisiacs].

[You have selected [Weak to Aphrodisiacs]]
[Applying changes]
[Raine gained [Weak to Aphrodisiacs]!]

"Now little Raine, I'm sure we'd both love to continue, but Mistress has to go shopping to buy you some things okay? You can keep yourself entertained for a few hours can't you?" She asked.

-----------

Raine's POV:

"Now little Raine, I'm sure we'd both love to continue, but Mistress has to go shopping to buy you some things okay? You can keep yourself entertained for a few hours can't you?"

Raine nodded, still cum-drunk from the monstrous load his Mistress had shot inside him. He watched as she got dressed and moved across the room to the door. She spun the handle and the door creaked open.

"Goodbye Raine." she cheered.

Raine was left sitting on bed. He opened his notifications again.

[Class Changed: Covenanter ===> Covenant Mage]

[You gained 1d3 HP and 1d3 MP]
[Rolling]
[Rolled: 1]
[You gained 1 HP!]
[Rolling]
[Rolled: 3]
[You gained 3 MP!]

[You gained a new trait! [Weak to Aphrodisiacs]].

Raine focused on the new trait, wondering what exactly it meant.

[[Weak to Aphrodisiacs] - You have become weak to Aphrodisiacs. The Effect [Aphrodisiac Affected] doubles in strength. Once a week, levels of [Aphrodisiac Affected](temporary) will be converted to [Aphrodisiac Affected](permament) at a ratio of 20:1. A maximum of 100 levels of [Aphrodisiac Affected](temporary) may be converted at any one time.]

Raine started to feel the increased heat in his loins as he recovered from his prior orgasm. Now he was experiencing a 64% increased level of arousal and it was honestly getting a bit difficult to think. Without thinking, his hand reached down to his shaft, which he found to be rock hard again. He began to stroke vigorously, the pleasure becoming overwhelming very quickly.

[[Weak to Aphrodisiacs] conversion affect applied]
[Effect Diminished: Aphrodisiac Affected (Temporary): Level 30 ===> Level 10]
[[Aphrodisiac Affected](Permanent) has increased in level. Level 2 ===> Level 3]

Raine felt the strength of the effects diminish somewhat, returning to a level similar to what it had been prior to gaining his new trait. He was still masturbating, [Aphrodisiac Affected] and [Body Sensitivity] still strong enough to make him incredibly horny. After a couple minutes, he found himself cumming for a second time that day. Semen dripped from his cock once more as Raine kept rubbing, trying to extract more and more pleasure from his cock. A few minutes later, his penis was erect once more and he was masturbating once again, his shaft slick with semen and precum.  As the day drew on, with nothing else to do, Raine continued to lie there and did nothing but stroke his increasingly abused penis. About 2 hours into this he received a notification.

[Permanent Effect Gained: Ejaculation Addiction.]

Continuing to rub his dick, Raine read the description of the new effect.

[[Ejaculation Addiction](Permanent) - You have become addicted to ejaculating. From now on, your penis will be 1% more sensitive per level. Failing to ejaculate for 24 hours may have side effects]

His penis did feel slightly more sensitive, he decided to keep stroking it. His moans filled the room as he pleasured himself. Then, he orgasmed, by now only the smallest drop of semen lazily emerged from his tip - but the pleasure was no less intense for it. Exhausted, he finally stopped masturbating, and his penis flopped limply against his pubic region.

[[Ejactulation Addiction] has increased in level. Level 1 ===> Level 2].

'Oh' Raine thought, 'will that increase every time I cum now?' He found himself quite liking the idea.

Then there came a creak as the door opened. His mistress entered the room, carrying a bag. She looked down at Raine, lying in her bed covered in and surrounded by semen.

"My, you have been a busy little male haven't you?" She said.

-----------

Changes in this Chapter:

[Class Change: Covenanter ===> Covenant Mage]

[Level up: Level 0 ===> Level 1]

[Gained Trait: [Weak to Aphrodisiacs]]

[Gained Permanent Effect: Ejaculation Addiction: Level 2]

[Permanent Effect Increased: Aphrodisiac Affected: Level 2 ===> Level 3]

[Effect Increased: Entranced: Level 3 ===> Level 4]

[Effect Increased: Heightened Submission: Level 3 ===> Level 4]

[Effect Diminished: Aphrodisiac Affected: Level 26 ===> Level 10]

Chapter Text

Raine sat up. His mistress came up to him, placing the bag down beside the bed. She reached over and grabbed Raine by his chin, pulling him in gently for a kiss.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[You have ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] has increased in level. Level 10 ===> Level 13. Cumulative Level: 16]

His mistress's familiar tongue spent a little while longer in his mouth, before she chose to withdraw it back into her own. She brushed a stray hair from out of Raine's face.

"How many times did you cum while I was out, little Raine?" She inquired

"11, Mistress" Raine answered. To which she smiled wickedly.

"And with me not there? Well, I think I should get to cum 11 times before you do next, just to make things even." She proposed.

Raine thought about it. Chances were 24 hours would pass before he had the chance to make Mistress Tazamoth cum 11 times - and the side effects mentioned in the description of [Ejactulation Addiction] would kick in. Since Mistress had made an order, he couldn't even bring himself to orgasm until he'd completed his assigned task. It was starting to look like he'd have to suffer the unknown consequences of his new effect. Still, there was a slim chance at success and besides, even if he failed he'd still be pleasuring his Mistress, and that'd be enjoyable all by itself.

"Oh, and Raine? I know about that new effect you have, I saw the notification on my way home. So I'd suggest you get started now." She said as her eyes flashed green and her shorts began to bulge.

Raine clambered forward, getting off the bed. He knelt before his mistress and undid the buttons on the front of her shorts. Soon a thick member flopped out in front of him, which he grasped with gusto. he licked his mistress's massive tip, coaxing out a dribble of precum, which he happily sucked up into his mouth. He continued to lick down her shaft, arriving at the base of her penis before pulling back and opening his mouth to begin sucking on the cock properly. Raine felt every vein along his Mistress's perfect dick as he descended towards her base. 5 inches down he gagged, pausing slightly before continuing on down towards his mistress's smooth crotch. Mistress's let out a soft moan as his lips retreated back to the tip of her massive cock. Rain stopped for a second before diving back down to half way down her penis again.

"Oh, you are eager. I wonder if you really will make me cum 11 times before the time's up" His Mistress exclaimed.

Up and down her cock he went again and again.

"Good boy... keep going."

The taste of his mistress overwhelmed his senses.

"Nearly there Little Raine."

Saliva and precum flowed past his lips onto his bare thighs and erect penis as he upped the pace. Then his mistress grabbed him by his hair and pulled him off her cock. 

'My hair's long enough to be pulled?' Raine thought to himself, 'I suppose that it's been a little over 2 months since my the academy was destroyed, and I hadn't had a haircut in over a month when that happened.'

Raine's hands grabbed onto his Mistress's she-cock and started stroking, pointing her penis at his face and opened his mouth. His mistress came and her thick semen splattered all over his face, her large balls emptying out an inhuman load all over Raine as she moaned. Several globs of cum entered Raine's mouth, and he guided the remaining cum on his face into his slutty mouth and swallowed.

[You have brought your Mistress to orgasm! +10XP]

[You have swallowed Demon Semen. +1XP]

[You have ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] has increased in level. Level 13 ===> Level 16]

[[Entranced] increased in level. Level 4 ===> Level 5]

[[Heightened Submission] increased in level. Level 4 ===> Level 5]

Raine felt the arousal wash over him as [Aphrodisiac Affected] leveled up. Warmth bloomed over his body.

"Good boy Little Raine. Now, before we continue, why don't I show around your new home, I know you've only been in this room so far. First though, I'd like to give you your first present from my shopping spree today." His mistress said, reaching into her bag.

She withdrew a large hinged loop made of the same dark metal that she seemed to own many items of. [Dangersense] pinged, warning him that the object, dubbed a 'Blacksteel collar', was definitely cursed - pretty powerfully too. Mistress Tazamoth presented it to him, and he accepted it into his hands. His mind conjured up several erotic effects it could have. He was excited at the prospect of finding out what it did. Looking it over, it was made of two half loops joined by a hinge, which clearly was the 'rear' of the collar. He saw that the front had a small spherical red gem attached to it on a smaller loop, almost like how a bell was fitted on a cat's collar.

"Go on, Little Raine. Put it on for mistress." 

Raine, ever obedient, complied and lifted it up to his neck. He closed the hinge and moved to secure whatever latching mechanism held it in place, only to find it had become completely smooth. Now there was a solid ring of blacksteel around his neck, that he wouldn't be able to take off. Notifications flooded in.

[[Cursed Blacksteel Collar] Equipped!]
[[Cursed Blacksteel Collar] Primary Curse Activated: Strong Binding Curse!]
[[Cursed Blacksteel Collar] Secondary Curse Activated: Lust Curse!]
[[Cursed Blacksteel Collar] Tertiary Curse Activated: Feminisation Curse!]
[[Cursed Blacksteel Collar] can no longer be removed!]
[[Body Sensitivity] has increased in level! Level 8 ===> Level 9!]
[[Aphrodisiac Affected](Temporary) has increased in level. Level 16 ===> Level 17]
[[Aphrodisiac Affected](Permanent) has increased in level. Level 3 ===> Level 4]
[Special Trait Gained: [Feminisation] Current Percentage: 0% Feminised!]

Raine gasped audibly at the list of notifications. A triple cursed item was pretty serious, even if one of the curses was entirely focused on Binding it to him. He went to look at the items description.

[[Cursed Blacksteel Collar] - A collar made from the hellish material known as Blacksteel by a skilled craftsman. It carries 3 curses - a [Strong Binding Curse], a [Lust Curse] and a [Feminisation Curse].]

Raine focused on the curse effects to find out what they would do.

[Strong Binding Curse: Collar Cannot be removed unless physically destroyed or is hit with Unbinding spell with 1,500 MP cost.]

[Lust Curse: Every 24 hours, gain 1 level of [Body Sensitivity] up to level 100. Every 24 hours, gain 1 level of [Aphrodisiac Affected] up to level 125. On first equip, add 1 level to [Aphrodisiac Affected](permanent).]

[Feminisation Curse: Gain Special Trait: [Feminisation], which will increase from 0% towards 100% under certain conditions. +0.1% progress: whenever you ejaculate hands-free, whenever you swallow semen. Secret Conditions may also increase progress.]

Next he focused on the Special Trait [Feminisation]

[[Feminisation] - You are being feminised. As progress increases towards 100%, you will see increasingly feminine features. Features include: Softer skin, Loss of body hair, widening of hips, decrease in height, decrease in penis size, and decrease in testicle size. Upon reaching 100% trait will undergo evolution. Additionally, when wearing women's clothing, arousal will increase by 5% per item of clothing to a maximum of 25%.]

Raine was surprised by how powerful that trait was. 

"What do you think Little Raine?" His Mistress asked him.

Raine stared at himself in the mirror. He did look pretty good with it on.

"I love it, thank you mistress" He replied enthusiastically.

"I'm glad, now let me show you around the rest of your new home." She said, standing up.

She lead him to the door, opening it with ease, her arms flexing with subtle muscle as she pushed the heavy metal door open. They went through revealing a short hallway as his mistress spoke.

"The door opposite us is the casting room, you are not to enter there without my presence." She ordered

"Yes mistress"

"The next door down to the right is the Kitchen." She explained

Raine looked inside and saw a fairly regular kitchen, albeit with a much more gothic theme.

"And on the left is the Library. Once again, you are not to go in there without my presence." she said as they walked on.

"Next on the right is the Dining Room, where I host my guests. It's connected to the kitchen. On the left are the servant quarters - I have a few lesser demons working as servants, you'll probably run into them eventually, but I've warned them that only I'm allowed to touch you, so they will leave you be." She continued.

"Now, lastly, here on the right are the guest bedrooms, and on the left is the living room." She said

The hallway from then on, only had a door on the left, with the right side having windows. Raine could just about make out a city on the horizon through them.

"This door on the left here is to the Bathrooms." She said. "Speaking of, we probably ought to get cleaned huh?"

Raine followed his mistress into the Bathrooms. The room was huge and mostly square, except for the two corners near the door. On the left sat a small Sauna, and on the right was a room featuring a toilet. The rest of the room was taken up by heated bath so large it was practically a small pool. Steam wafted off the water, which was constantly drained in the centre and refilled by a waterfall coming from the wall. It was less of a Bathroom and more of a spa.

Mistress Tazamoth stripped, tossing her clothes aside and waded into the water, beckoning Raine to follow. He stood as he watched her massive flaccid cock sway in as she got deeper into the water. The water was warm but soothing, he felt the grime from the past few days wash off of him. His mistress reached the far side of the bath, sitting on the seats along the edge. Raine joined her, the hot waters leaving him feeling tired. He leant against her, submerged from the shoulders down. The exhaustion from all the sex and masturbation finally caught up to him, and he drifted off to sleep against his Mistress.

"Good boy Raine."

-----------

Changes in this Chapter:

[Cursed Equipment Gained: Cursed Blacksteel Collar]

[Special Trait Gained: [Feminisation] 0%]

[Permanent Effect Increased: Aphrodisiac Affected: Level 3 ===> Level 4]

[Permanent Effect Increased: Body Sensitivity: Level 8 ===> Level 9]

[Effect Increased: Aphrodisiac Affected: Level 10 ===> Level 17]

[Effect Increased: Entranced: Level 4 ===> Level 5]

[Effect Increased: Heightened Submission: Level 4 ===> Level 5]

Chapter Text

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolls failed: Already at full HP and MP!]

[Effect Decreased: Entranced: Level 5 ===> Level 4]

[Effect Decreased: Heightened Submission: Level 5 ===> Level 4]

Raine jerked awake. He had been leaning against his mistress in the baths and he must've fallen asleep. Clearly he'd been moved, as he was now lying on his mistress's bed. Across from him was his nude Mistress, who was reading from a book containing what looked like Enochian letters - Raine had never gotten far enough in his studies to be allowed to take lessons in the language. He shifted slightly and Mistress Tazamoth took notice.

"Awake darling?" she asked.

"Yes Mistress."

"Just to let you know by the way, you were out for 13 hours then, from my understanding of it, you've got about 9 hours to make me cum 10 times." She stated plainly.

'Fuck, I'm so screwed, I'm definitely not going to be able to avoid the side effects' Raine thought to himself.

"Can we start then Mistress?" he asked

"Tt. So presumptuous... I was going to show you another gift I got you first." Mistress Tazamoth said, slowly putting her book down. "But now... I think I'll show you one of my toys first."

His mistress's eyes turned green, as a greenish length of rope appeared in her hands.

"Behold, my enchanted mandrake rope, made from real mandrake fibres. Now, stay." She said

His body practically locked up at the command. His mistress paced over to him, grabbing his arms and pressing them behind his back. He felt the rope brush against his skin as his Mistress tied his hands together behind his back.

[You have been Restrained!]
[Enchanted Mandrake Rope applied an affect on you!]
[Gained Effect: Mandrake-Drunk]

Raine looked at the new effect's description.

[[Mandrake-Drunk](temporary)(increasing) - +5% Arousal per level, +2% Body Sensitivity per level, all mental compulsions increased in strength by 2% per level, Disadvantage on all saving throws. Fertility increased by 50% per level.]

Damn, that was pretty strong stuff.

"I love Mandrake rope, some idiot always summons me for a good fucking in return for me being set loose on Middleplane and then half-way through they agree to let me tie them up with this. The next thing they know, they've sold their soul to Ioketara and I'm free to go level up." His mistress supplied helpfully. "Of course, you were already so keen to give your soul to me personally, so I just had to see your cute reaction to it."

She flicked his ear and he moaned.

"Now, let's get your debt paid off." His mistress said hypnotically

[[Entranced] increased in level. Level 4 ===> Level 5]

[[Heightened Submission] increased in level. Level 4 ===> Level 5]

Raine opened his mouth, and his mistress's cock plunged in. Her girthy cock charged past his tongue and into his gullet, cutting off his airways slightly and causing him to gag. With his hands unable to steady him, he toppled over onto his side from where he was kneeling on the bed. His mistress followed him down, showing him no mercy as she ruthlessly and animalistically fucked his throat. Soon Raine found himself pinned on his back, his mistress kneeling over his face, rhythmically thrusting in and out. Raine felt utterly defeated and emasculated, which only made his throbbing hard dicklet throb harder. He wished he could stroke it, but his mistress's orders and the mandrake rope tying his hands behind his back meant all he could do was uselessly jiggle as his mistress mouthfucked him utterly senseless.

[[Mandrake-Drunk] increased in level. Level 1 ===> Level 2]

Gods, he felt even more sensitive. He needed release. He needed to make his mistress cum. Raine tried to use his tongue to pleasure Mistress Tazamoth's cock as it was thrust in and out of his mouth. Eventually, his mistress started to moan louder and louder, orgasming and release a flood of semen down Raine's gullet. He lapped it up with gusto and great pleasure. Licking his mistress's urethra as the last of the load dribbled out.

[You have brought your Mistress to orgasm. +10XP]

[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress].

[You have ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 17 ===> Level 20]

Yet his Mistress didn't stop. Her flaccid member immediately engorged once again and within 20 seconds she was back drilling his mouth. Raine hummed out a moan around her fat cock. He hoped his mistress never stopped fucking him in the mouth.

-----------

8 hours of brutal throat-fucking later

-----------

Over the next few hours, Mistress Tazamoth came another 9 times, meaning he only had to make her cum once more before she would let him cum. Raine was exhausted again, Mistress Tazamoth had finally relented and given him a few minutes to collect himself. He finally looked at all the notifications he'd been ignoring during the harsh mouthfucking, the system had taken the liberty of highlighting the most important notifications.

[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 20 ===> Level 23]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 23 ===> Level 26]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You have reached Level 2!]
[You gained 1d3 HP and 1d3 MP]
[Rolling]
[Rolled: 2]
[You gained 2 HP!]
[Rolling]
[Rolled: 1]
[You have gained 1 MP!]
[You have 1 Unassigned Skill Point]
[You ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 26 ===> Level 29]
[[Mandrake Drunk] increased in level. Level 2 ===> Level 3]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 29 ===> Level 30 (Cap)]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[You have reached Level 3!]
[You gained 1d3 HP, 1d3 MP and 1 Intelligence]
[Rolling]
[Rolled: 2]
[You gained 2 HP!]
[Rolling]
[Rolled: 2]
[You have gained 2 MP!]
[You have 2 Unassigned Skill Points]
[You brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +1XP, +0.1% [Feminisation] Progress]
[[Mandrake Drunk] increased in level. Level 3 ===> Level 4]
[Permanent Effect Gained: Semen Addiction]
[Permanent Effect Gained: Oral Addiction]

Raine understood most of these notifications. The Majority were just XP and Level up notifications or were effects he was well familiar with. He - or his mistress - would assign his skill points later, such things needed time taken to think about them. Instead he decided to look at the descriptions of [Semen Addiction] and [Oral Addiction].

[[Semen Addiction] - You have become addicted to Swallowing Semen. Swallowing Semen has a 33% chance of awarding an additional +1XP. Failing to come into contact with another sapients semen for 24 hours may have side effects.]

[[Oral Addiction] - You have become addicted to Oral Sex. Failing to perform Oral Sex on another sapient or receive Oral Sex from another sapient for 24 hours may have side effects]

Great. He'd gone and gotten another Trait with potential side effects, this one seemed even harder to control than his [Ejaculation Addiction]. He looked over at his Mistress, who only smirked at him.

"A new addiction huh Little Raine?" she said as if she didn't already know.

"Perhaps I should've swapped out my cock for my pussy earlier. Oh well! You live and you learn I suppose." She continued.

Her eyes flashed green and her penis slowly shrank and disappeared, revealing her vagina once more. She moved over to sit by Raine again.

"Shall we continue sweetheart?" She asked

"Yes Mistress."

She grabbed him, guiding him to her pussy. Raine ran his tongue across it with urgency, he probably had less than 30 minutes until [Ejaculation Addiction]'s side effects kicked in. He lapped and licked at his mistress's wet cunt as though it were a life or death scenario. Mistress slowly ran her fingers through his black hair, massaging his scalp soothingly. Occasionally, she would let out a moan as he went about his work, and these through these moans were interspersed various words of encouragement.

"Ahhn... Good work my little Raine, keep going."

"Good boy."

"Yes! Continue. Ah."

After pleasuring his mistress for about 15 minutes, the giant demoness finally came. Fingers running through his hair turned into a strong grip, making sure he couldn't pull back. Her thighs tightened around his head as she bucked. Raine was pressed so hard against her pussy that he could hardly breathe, but he continued to pleasure her even still. Then she let go, her death-grip on his hair releasing and her thighs moving back out, letting him retreat from her crushing pelvic embrace.

[You have brought your Mistress to orgasm. +10XP]

"Good job Little Raine" she whispered

"I think I'll let you cum now" she continued, "but first, lets get those ropes off you."

"Yes Mistress." Raine said as he stood up. His knees were bruised from kneeling for hours. He found the dull throb of pain almost pleasant.

Mistress Tazamoth walked around behind him. She knelt down, and began untying whatever complex knotwork she had used to bind his hands together. The whole thing was agonisingly slow, Raine thought she'd be able to do it faster, but then again Raine didn't know the first thing about bondage, so who was he to judge? Still, after a couple minutes, his mistress had untied him. She gestured to the bed. 

"On." she commanded

Raine moved sat in the middle of the bed. His Mistress got on the bed behind him. Then, she pulled him down so that he was lying atop of her, head nestled between her large breasts. He stared up at the ceiling as his Mistress's legs intertwined with his, restraining them. His short member stood to attention and his mistress planted a strong hand around it. Then she shifted him up slightly, so that his neck was now in line with her head. She began to stroke his cock and Raine let out a whimper.

"Good boy Raine, whimper for your Mistress." She whispered into his ear.

Mistress Tazamoth continued her slow, methodical stroking as she kissed his neck. Her saliva feeling warm against his bare skin.

"Such a pretty little thing" she said after withdrawing from the kiss.

She moved back in, instead of kissing his neck however, her teeth sank into the flesh, causing him to moan in pain and pleasure.

[Your Mistress, Tazamoth, has used [Foolish Bite] against you.]
[Hit!]
[You took 1d8 piercing damage!]
[Rolling]
[Rolled: 6]
[You lost 6 HP!]

[Beginning Hard Wisdom Save with Disadvantage (Entranced)]
[Minimum Saving roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling]
[Rolled: 17, 1!]
[Critical Failure! Doubling effects!]
[You have gained 4 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity](Permanent) increased in Level. Level 9 ===> Level 13]

Raine moaned even harder as the sensations of his cock got even stronger. He was getting close already, and his mistress took notice, slowing down slightly so he could enjoy this for longer. Precum dribbled from his dicklet as she pumped her hand up and down, giving the thing a watery sheen. He let out a gasp of pleasure.

"You like that huh Raine?" His mistress asked rhetorically

"Yes Mistress" he said, too aroused to notice the rhetorical question

His mistress chuckled as she continued to stroke, edging him ever closer to cumming.

[24 hours have passed since you last ejaculated! Side effects will be applied shortly!]

'Shit', thought Raine.

-----------

Changes this chapter:

[Special Trait Progress Increased: Feminisation: 0% ===> 1.0%]

[Gained Permanent Effect: Semen Addiction: Level 1]

[Gained Permanent Effect: Oral Addiction: Level 1]

[Permanent Effect Increased: Body Sensitivity: Level 9 ===> Level 13]

[Gained Effect: Mandrake Drunk: Level 4]

Chapter Text

Raine's POV:

Raine's worry about the impending consequences of failure was quickly replaced by a mindless arousal as he neared orgasm. His mistress sped up her stroking to a ferocious pace as he whimpered and moaned, planting another kiss against his neck. Raine experienced full body shudders as he came, flexing in his Mistress's grip. 

[A [Succubus] has brought you to orgasm! Body Sensitivity has increased in level. Level 13 ===> Level 14]

[[Feminisation] Progress increased by 0.1%. Current Progress: 1.1%]

His mistress let go of him, letting him roll off of her onto the bed. He moaned slightly, and turned to face his mistress.

"Were you too slow, Little Raine?" she teased.

"Y-Yes Mistress" Raine said defeated.

"Oh cheer up, I think you'll enjoy the consequences." She whispered conspiratorially. "I've been told that they can be rather fitting"

Raine nodded, mollified slightly. A Notification came through.

[Subject deemed inactive. Beginning Application of Side Effects!]

Raine flinched in surprise.

[Gained Effect: Sexual Frustration]
[Rolling Random Side Effects (1d20)]

Raine looked at both of their descriptions.

[[Sexual Frustration](Temporary) - You have become Sexually Frustrated. +1% Arousal and +1% Sensitivity to all physical stimuli per level. Disadvantage on all Wisdom Saving Throws. Can only be decreased by orgasm.]

[Random Side Effects (Ejaculation Addiction): A 20-sided die will be rolled to determine additional side effects. Side effects are as follows:

20 - No additional Side Effects
19 - 1 Level of [Sexual Frustration]
18 - 2 Levels of [Sexual Frustration]
17 - 3 Levels of [Sexual Frustration]
16 - 4 Levels of [Sexual Frustration]
15 - 5 Levels of [Sexual Frustration]
14 - 2 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent)
13 - 4 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent), 2 Levels of [Aphrodisiac Affected](Permanent)
12 - 5 Levels of [Sexual Frustration], 3 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
11 - 10 Levels of [Sexual Frustration], 1 Level of [Ejaculation Addiction]
10 - 10 Levels of [Sexual Frustration], 2 Levels of [Ejaculation Addiction], 1 Level of [Body Sensitivity](Permanent)
9 - 10 Levels of [Sexual Frustration], 3 Levels of [Ejaculation Addiction], 1 Level of [Body Sensitivity](Permanent), 1 Level of [Aphrodisiac Affected](Permanent)
8 - 10 Levels of [Sexual Frustration], 5 Levels of [Ejaculation Addiction], 3 Levels of [Body Sensitivity](Permament), 1 Level of [Aphrodisiac Affected](Permanent)
7 - 10 Levels of [Sexual Frustration], 10 Levels of [Ejaculation Addiction], 5 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
6 - 10 Levels of [Sexual Frustration], 10 Levels of [Ejaculation Addiction], 10 Levels of [Body Sensitivity](Permanent), 5 Levels of [Aphrodisiac Affected](Permanent)
5 - 10 Levels of [Sexual Frustration], 1 Level of [Erectile Dysfunction](Temporary)
4 - 10 Levels of [Sexual Frustration], 2 Levels of [Erectile Dysfunction](Temporary)
3* - 10 Levels of [Sexual Frustration], Gain Trait [Supersensitivity], 3 Levels of [Erectile Dysfunction](Temporary)
2* - 10 Levels of [Sexual Frustration], Gain Trait [Strengthened Orgasm], 4 Levels of [Erectile Dysfunction](Temporary)
1** - 10 Levels of [Sexual Frustration], Penis shrinks by 0.25 Inches, 5 Levels of [Erectile Dysfunction]

*Traits only applied once, subsequent rolls will only add Levels of [Sexual Frustration] and [Erectile Dysfunction]
**Shrinkage only occurs once, subsequent rolls will only add Levels of [Sexual Frustration] and [Erectile Dysfunction]]

Raine gulped audibly, some of these consequences seemed... pretty intense. As much of a pervert as he was, he wanted to slowly accrue these things, he hoped he didn't roll too low.

[Rolling]
[Rolled: 4]
[Gained: 10 Levels of [Sexual Frustration]]
[Gained: 2 Levels of [Erectile Dysfuncton]]

Raine felt the increase in arousal wash over him. Yet despite the increase, his dick didn't get hard, just stayed its flaccid length of 3 inches. He looked at the description for [Erectile Dysfunction].

[[Erectile Dysfunction](Temporary) - Prevents erections and makes ejaculation much harder. Decays 1 level every [Long Rest].]

Looks like he was going to be rolling the wheel of random side effects again soon. 

His mistress looked at him for a second, probably opening his character info to look at what he'd rolled. She evidently dismissed the info, as she turned to Raine.

"Aww, does Little Raine's pathetic man-penis not work right now?" She said with fake sympathy masking a real hunger.

Raine blushed and nodded.

"Well, I wasn't going to introduce you to this quite yet, but now is a good time to give you another of the items I got for you." She said.

His mistress got off of the bed, bending down to reach into the bag she'd brought back a couple days ago now. She fiddled around a bit, looking for whatever item she was going to pull out. Finally, she pulled out a set of 3 items. A darksteel ring a couple inches across with a strange protrusion at the top, a small dark steel cylinder that rounded off at one end except for a small hole in the middle, and then finally a key with part of a lock wrapped around it. Raine struggled to identify what exactly he was looking at for a while before it hit him. He was looking at a chastity cage. The thought of being forced to wear it made his cock twitch and engorge ever so slightly.

"I got my precious Little Raine a chastity cage. This chastity cage is a little larger than I'd like, but we need to train you more before we downsize. You'll be wearing this for the next couple days, and whenever we go out in public." His Mistress said. 

Raine's [Dangersense] alerted him, the 'Blacksteel Chastity Cage' was cursed, like his collar. It didn't ping as strongly though, so perhaps it was only a dual cursed artefact? Or maybe the curses were weaker? It could also be that his [Dangersense] was getting less sensitive to things his Mistress did though. Regardless, he was soon commanded to stand before his Mistress. She knelt down, grabbing Raine's cock and balls, slowly tugging his balls through the loop. His penis soon followed and the ring sat at the base of his shaft, cupping his balls slightly. Mistress Tazamoth then took the cage itself, slipping it over Raine's penis, pushing it back to the protrusion at the top of the ring, which combined together to form most of a lock. Finally, the key was inserted into the lock and turned, sealing the cage shut.

[[Cursed Blacksteel Chastity Cage] Equipped!]
[[Cursed Blacksteel Chastity Cage] Primary Curse Activated: Regulated Binding Curse!]
[[Cursed Blacksteel Chastity Cage] Secondary Curse Activated: Weak Lust Curse!]
[[Cursed Blacksteel Chastity Cage] Tertiary Curse Activated: Anal Sensitivity Curse!]
[[Cursed Blacksteel Chastity Cage] can no longer be removed by you!]
[Permanent Effect Gained: Anal Sensitivity!]
[[Feminisation Curse] Secret Condition met: Equipped Chastity Cage: +0.1% [Feminisation] Progress. Current Progress: 1.2%]

Raine could feel the slight pressure that came from the chastity cage, he imagined that if he were capable of getting an erection right now that that pressure would increase to mind-bogglingly erotic levels. He read through the item description for his new cursed cage, as well as the descriptions of the effects.

[[Cursed Blacksteel Chastity Cage] - A chastity cage made of a hellish material known as Blacksteel by a skilled craftsman. It carries 3 curses - a [Regulated Binding Curse], a [Weak Lust Curse] and, an [Anal Sensitivity Curse]. This cage has a length of 2.5 inches.]

[Regulated Binding Curse: Chastity Cage can only be removed by one person (Tazamoth Homophagos) unless physically destroyed or hit with an unbinding spell with 500 MP cost. Removal by others may have side effects.]

[Weak Lust Curse: Every 24 hours, gain 1 Level of [Body Sensitivity] up to Level 50. Every Week, gain 1 Level of [Aphrodisiac Affected] up to Level 100.]

[Anal Sensitivity Curse: Every time you reach orgasm through anal sex, gain 1 Level of [Anal Sensitivity] up to Level 100.]

Raine's second guess seemed right, these curses were a fair bit weaker than the ones on the collar - though they were still powerful enough to be seriously worrying, if he weren't his mistress's covenanter. In any other context, being stuck with 6 Demonic Curses would be a death sentence. He wondered if he'd get more anytime soon. He decided to read the description of the [Anal Sensitivity] effect.

[[Anal Sensitivity](Permanent) - Your ass, anus and prostate become 1% more sensitive per level].

That was pretty simple, and about what he'd expected. His mistress stepped back, admiring her work. She licked her lips.

"Now that your shameful little man-dick has been locked away, why don't I introduce you to a new form of stimulation." She said salaciously.

"O-okay mistress, what do you uh. Have in mind?" Raine stammered out, flustered by the cool sensation of his new cage.

"Anal." She said.

She walked over to one of the cabinets, opening a drawer, she pulled out a small flask, presumably of Lube. She stalked back over to where Raine stood.

"Lie down on the bed" She commanded.

Raine moved instinctively, lying down on his back on the bed. His Mistress knelt on the bed, unscrewing the flask and pouring some lube onto her hand.

"Uh... Mistress? Doesn't this sort of thing generally require a bit more prep?" He asked nervously

His mistress laughed "Silly little Man-thing. Hell works very differently to the Middleplane. Here, little things like biological aging, hunger or necessary biological functions don't really apply. Did you not think it was weird that you've been here for almost 3 days now and yet you haven't eaten, drank or even had to use the toilet?" She asked.

"Wait so I only age in Middleplane?" Raine asked, shocked.

"Actually you don't age there anymore either. Denizens of Hell such as myself don't age at all - for complicated soul reasons that basically boil down to our bodies being projections of our souls. Since your soul is bound to mine through our bond, you get included in that too. It's the same thing that makes it nearly impossible to truly kill a Demon in the middleplane - our souls in Hell just form a new projected body. I'm told that Heaven Denizens get the same deal too." Mistress Tazamoth explained casually, as if she hadn't just dropped the bombshell on Raine that he was now functionally immortal.

"I. Uhhh. I- Wow." Raine managed

"Now shut up and let me finger your ass." His mistress said, ruining the moment.

"I. Yes M-mistress." Raine stuttered.

-----------

Tazamoth's POV

"Lift your legs up, and hold them out of the way." Tazamoth demanded.

Raine obliged, lifting his legs into the air, holding them out of the way with one of his arms which wrapped around the back of his thighs. Only his ass and his caged dick were visible to Tazamoth as his upper body was obscured by his legs. Raine craned his neck to look around his legs at his beloved mistress. She rubbed her hands together, coating both of them in a thin layer of lube. She reached for the flask again, grabbing it and pouring out a little more onto her right hand. She massaged it into his ass, his hole now having a wet gleam to it. She marvelled at its smoothness - Half-elves (and elves) ordinarily had very little body hair, and between Raine's blossoming [Feminisation] and original lack of manliness, he had even less hair than the average, plus it was lighter and shorter. Of course, less didn't mean none, something that Tazamoth intended to remedy very soon.

Carefully, she poked her middle finger at his tight asshole. Raine whimpered slightly as her finger slowly entered. Tazamoth reached the first knuckle on her middle finger. Despite being a total perv, it was clear that her Little Raine had not ever tried anal, he exuded a certain nervousness that told Tazamoth that her little Covenanter had never gotten adventurous enough to try.

"Good boy Raine, you're so brave." she placated him

Her finger slid in deeper, sliding past the knuckle, eliciting a sharp gasp from her Little Man-thing. The gasp soon changed to a high-pitched moan as she eased her second knuckle in. Pretty soon, she was at the base of her finger and she felt Raine shiver. She gave his encased cock a playful little wiggle with her left hand, eliciting another cute little moan from the Half-Elf, her Half-Elf. She pulled her finger out slowly, stopping at the first knuckle before driving it back in, slightly faster this time. She repeated the action a couple times, speeding up slightly with each pass. Lustful boy moans filled the air as she carried on. Then, she slowed once more, drawing her finger back until it was almost out. She took her ring finger and placed it against Raine's entrance.

"How about two fingers? Do you think you can do that for Mistress?" She asked.

"Yes Mistress, I can do that for you." Raine responded, voice wavering.

"Good boy Raine. I'll be able to properly take your anal virginity in no time." She said as she smiled.

She slid her ring finger in alongside her middle finger, meeting great resistance from Raine's untrained hole. Once more, she slowly slipped further inwards, past the first knuckle, then the second, then reaching the base of her fingers. Raine let out a particularly loud moan at that, and a droplet of watery precum passed through the small hole at the tip of his chastity cage. She then repeated her process before, plunging in and out of his ass slowly building up speed. Raine squealed as her fingering intensified, the Half-Elf left shaking from the pleasure. She slowed down again and Raine began to yawn - clearly he'd become quite tired over the day. She herself was pretty tired, even though she was a Succubus, cumming 11 times back to back was a lot. She withdrew her fingers entirely.

"I think it's time for bed Raine." she said

"If you say so Mistress" he replied.

"But first, one last gift before you sleep."

She grabbed the bag from beside the bed, sitting it on her lap and rumaging through to find a small black box. Opening it, she selected the left-most object.

-----------

Raine's POV

His mistress pulled out a small black box and took the lid off of it, careful not to show Raine what was within. She picked an item out of the left side of the box. She placed the box back in the bag, and let Raine see it. Instantly he recognised it as a Butt Plug made of Darksteel, he wondered if she got the plug, cage and collar as a set. [Dangersense] instantly recognised it as a cursed object, though only weakly - weaker than his cage at least. His mistress grabbed the flask of lube again, pouring out a little onto the plug. Raine was still in the same position that she'd been fingering him in, so she leaned in closer and slowly pushed the plug into his tight ass. The pleasure was immense, the plugs diameter being just less than his Mistress's two fingers, but much harder. It finally slipped in up to the base, and he suddenly realised how exhausted he was. 

"You can go to sleep now Raine." His mistress said, as notifications suddenly flooded his mind.

[[Cursed Blacksteel Butt Plug] Equipped!]
[[Cursed Blacksteel Butt Plug] Primary Curse Activated: Increasing Sensitivity Curse!]
[[Cursed Blacksteel Butt Plug] Secondary Curse Activated: Very Weak Arousal Curse!]
[[Feminisation Curse] Secret Condition met: Equipped Butt Plug. +0.1% [Feminisation] Progress. Current Progress: 1.3%]

No binding curse, clearly this was not meant to be worn for a long time. Raine looked at the descriptions of the plug and its curses.

[[Cursed Blacksteel Butt Plug] - A Butt Plug made from a hellish material known as Blacksteel by a skilled craftsman. It carries 2 curses - an [Increasing Sensitivity Curse] and a [Very Weak Arousal Curse].]

[Increasing Sensitivity Curse: If the Plug is equipped for the entire duration of a Long Rest, gain 1 Level of [Anal Sensitivity](Permanent) up to a maximum of 100.]

[Very Weak Arousal Curse: When the plug is equipped, arousal is increased by 10%.]

The curses seemed pretty weak, and pretty simple. With nothing else to do, Raine curled up next to his mistress, getting spooned by the taller woman as he drifted off to sleep.

-----------

Changes this chapter:

[Gained Cursed Equipment: Cursed Blacksteel Chastity Cage]

[Gained Cursed Equipment: Cursed Blacksteel Butt Plug]

[Special Trait Progress Increased: Feminisation: 1.0% ===> 1.3%]

[Gained Permanent Effect: Anal Sensitivity: Level 1]

[Permanent Effect Increased: Body Sensitivity: Level 13 ===> Level 14]

[Gained Effect: Sexual Frustration: Level 11]

[Gained Effect: Erectile Dysfunction: Level 2]

Chapter Text

4 Days since Covenant Formed

-----------

Raine's POV

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolls Failed: Already at full HP and MP]

[Permanent Effect Increased: Body Sensitivity: Level 14 ===> Level 16]

[Permanent Effect Increased: Anal Sensitivity: Level 1 ===> Level 2]

[Effect Decreased: Entranced: Level 5 ===> Level 4]

[Effect Decreased: Heightened Submission: Level 5 ===> Level 4]

[Effect Decreased: Erectile Dysfunction: Level 2 ===> Level 1]

Raine woke up to his mistress nudging him lightly.

"Wake up Raine, we've got a big day ahead of us. It's going to be your first time leaving the house - We're going into the city to get you acquainted to life in hell, as well as to pick up an order I made back when we first got home." she explained to the half-awake half-elf.

"Okay Mistress."

"Still, we've got some time to fit in a little training though if we're quick." She said, eyes flashing green as her dick emerged, "So you'd best get sucking."

Raine sat up and crawled over to his Mistress's stiff shaft. He immediately opened his mouth to suck and blow on her immense girth. He used his tongue to tease her wide head, stroking the cock with his right hand as he did so. His Mistress's precum mixed with his saliva to create an arousing cocktail in his mouth. Mistress Tazamoth groaned appreciatively as he worked his way down her cock. Slowly Raine's lips descended to the base of her shaft. Here she held him, preventing him from drawing back to breathe. He choked violently on her giantess dick as she held him there. His eyes watered and soon a couple tears ran down his face. Only then did his mistress relent, letting him pull back, her spit-coated cock leaving his mouth as he used both hands to stroke it.

"I love your cock Mistress" Raine professed

"Oh? What do you love about it my Little Raine?"

"I love its girth and its length. I love how much cum it shoots into my mouth. And I love that it makes mine look pathetic."

"Thank you Raine, your little man penis is very pathetic, that's why it's locked up right now and it's why you're choking on my fat She-cock right now. It's good that my little boy knows his place as a pathetic man-thing." She replied.

Raine felt his dick twitch in its cage at the verbal degradation. His penis seemed to be waking up a little bit now that [Erectile Dysfunction] had decreased to level 1 - though it still wasn't going to be hardening beyond a semi even if he didn't have his cage on. The pressure was arousing to say the least. He went back to sucking his Mistress's off, licking her slick tip.

"You know Raine, I can't wait to see you in an even smaller cage, with an even bigger plug as well. I want to make you as pathetic and pitiable as possible, my little cumslut. Maybe I should get you gag while we're out huh? Make it so all you can do is drool and give out little moans. Hmmm, but then I wouldn't hear your cute little voice. What do you think Raine?"

Raine pulled his lips off her cock for a second, "I'm yours to use Mistress, whatever you decide is best."

"Wow, you're a total little perv huh? You don't even care about being able to talk if it pleases your Mistress. How cute! How perverse. How... Pathetic" she said.

"I'm a pathetic little pervert Mistress" Raine said.

[[Entranced] increased in level. Level 4 ===> Level 5]

[[Heightened Submission] increased in level. Level 4 ===> Level 5]

"You're my pathetic little pervert" his mistress stressed before continuing, "Hmm. Maybe I should get you some nipple piercings to match my own as well. Hmm, maybe I should get some new jewelery for my tits. Hell, maybe I should get some entirely new piercings. I've not gotten any in ages, my only ones were only a few weeks after leaving imphood. Yeah I'll have to see if I can't get a booking soon. I can't believe I don't have any ear or nose piercings at the grand level of 74."

She looked down at Raine, who was still diligently slurping at her cock.

"Maybe I could get you some genital piercings? Maybe I should wait until you've shrunk a bit first though. Yeah, we'll table that one for later discussio-Ahhgn" She said with a moan, getting closer to climax.

"Perhaps I'll get some magic tattoos as well. I saw a demoness three - ah - days ago with some amazing tattoos on her, and the effects she said they had on Middleplaners, it - ah - simply sounds too alluring to not at least give it a try. Apparently she had one that just applied 12 levels of [Aphrodisiac Affected] permanently to those who saw it - ahn. Imagine that Raine!" She said between moans.

"Oh I can't wait to give you a tour of Gomhisseg, that's - ahhh - the city - oh - nearest where we live, my Little Raine." She said, as Raine blew her.

His mistress stopped talking, transitioning to only letting out moans as she got closer and closer to climax. Suddenly, she grabbed Raine's head, shoving him all the way down to the hilt of her shaft and then came, depositing semen directly down the Half-Elfs throat as he gagged and choked.

[You have brought your Mistress to orgasm. +10XP]

[You swallowed Demon Semen. +1XP, +0.1% Feminisation]

"Fuck that was good." Mistress Tazamoth exclaimed "I'm going to need morning blowjobs more often."

For his part, Raine coughed up some semen that had gone down the wrong way.

"Uh. Thank you for blessing me with your semen Mistress." He said as the last of the thick, virile liquid was coughed up.

"Now then Raine, why don't I get dressed then show you your new clothes?" Mistress Tazamoth suggested, her eyes glowing green as her penis shrank to nothing.

Mistress Tazamoth got off the bed and walked over to one of the wardrobes. Opening it, she selected a few hangers from inside, then grabbed a couple items off the wardrobe floor and a shelf on the left side of the wardrobe's interior. She returned to the bed, and laid it all out for Raine to see. She'd selected a sleeveless leather crop top and tight leather short shorts like she'd been wearing when they first met, but unlike last time, her boots were Thigh-High and had moderate heels - though like last time they were made of the same black leather. She had also retrieved a black thong (not made of leather), a pair of black tights and a pair of black Opera gloves made of a thinner version of the Leather that made up her other clothes. She quickly put it all on in front of Raine. He thought it made her look stunning, even more like a dominatrix than her prior outfit. Raine found himself particularly drawn to the fact that her thong was just barely visible above her shorts.

"Now Little Raine, let's get you dressed." She said.

She reached into the back, pulling out clothing that looked a lot like her own. Laying it out on the bed, she went through it with Raine.

"So I've got you a thong, some cute little shorts, a crop top similar to mine, enchanted latex thigh highs and long gloves, and some Leather Boots." She explained.

"Put the Thong on first." She commanded.

Raine picked up the thong, there really wasn't much material there at all. He put his legs through and pulled it up. The thin underwear did little to hide his chastity cage at all, but it did sit nicely against his butt plug.

[[Thong] Equipped. +5% arousal (Feminisation)]
[[Feminisation Curse] Secret Condition met: Wear women's underwear: +0.5% [Feminisation progress].]

"Now put the shorts on."

Like with the thong, Raine stuck his legs through and pulled the shorts up. He did up the button and zipper in the front. The shorts were very tight, and pretty obviously displayed his caged cock for all the world to see the impression of. Raine found that the idea of strangers seeing him like this turned him on. He didn't get an arousal increase, so he assumed that meant the shorts were unisex.

[[Hell-Leather Shorts] Equipped.]

"Now the top".

Raine lifted it over his head and stuck his arms in. It came to sit tightly against his chest, in a way that felt quite comforting.

[[Hell-Leather Crop Top] Equipped. +5% arousal (Feminisation)]

Huh, so the top did count.

"Lets put on that latex now darling, it's got some magic to help it stay on without creasing, you don't need to do anything but put it on."

[Dangersense] pinged as he picked up the thigh highs. Chances were there was some sort of curse on them that his Mistress was neglecting to mention, but Raine didn't care, the shiny material called to him, demanding he put it on. Raine sank his foot into one, feeling it stick to his skin once it was in place. Then, he put on the next one. Notifications started to come through.

[[Cursed Latex Thigh-Highs] Equipped! +5% arousal (Feminisation)]
[[Cursed Latex Thigh-Highs] Primary Curse Activated: Very Weak Binding Curse!]
[[Cursed Latex Thigh-Highs] Secondary Curse Activated: Weak Feminising Curse!]
[[Cursed Latex Thigh-Highs] Primary Enchantment Activated: Very weak Improved Grip]

A pair of curses and an enchantments was pretty impressive, even if they were all weak. He looked at their descriptions.

[[Cursed Latex Thigh-Highs] - Thigh-High socks made from Latex and subsequently Enchanted by an apprentice. It carries 2 curses - a [Very Weak Binding Curse] and a [Weak Feminising Curse]. It also carries a [Very Weak Improved Grip] Enchantment.]

[Very Weak Binding Curse: Latex Thigh-Highs cannot be removed unless physically destroyed or hit with an unbinding spell with 100 MP cost.]

[Weak Feminising Curse: Reduces body hair growth rate by 50%, and removes body hair in contact with it entirely. Every 24 hours, [Feminisation] Progress increases by +0.05%]

[Very Weak Improved Grip Enchantment: Any Agility Saving Throws involving your feet will receive a +1 to rolls.]

'Neat' thought Raine 'that Feminising Curse will make me more palatable to Mistress. Nice to have a +1 to Agility Saving Throws as well, even if I've recently become invested in failing saving throws. I wond-'

"Raine. Gloves now." His mistress said, cutting his thoughts short. 

Raine complied, picking up the gloves laid out for him. He sunk his arm into one, feeling the cool sensation of it sticking to his arm as it moved up it. His fingers reached the end of each finger of the glove, and he found that the glove extended half way up his bicep. Then he grabbed the other and put that one on, getting this one on a bit quicker, once again it fit snug to his arm.

[[Cursed Latex Opera Gloves] Equipped! +5% arousal (Feminisation)]
[[Cursed Latex Opera Gloves] Primary Curse Activated: Weak Complex Binding Curse!]
[[Cursed Latex Opera Gloves] Secondary Curse Activated: Weak Feminising Curse!]
[[Cursed Latex Opera Gloves] Primary Enchantment Activated: Aroused Spellcasting Enchantment!]

Raine was expecting the same as the Thigh-Highs, but this seemed a bit stronger. He looked at the descriptions once again.

[[Cursed Latex Opera Gloves] - Opera Gloves made from Latex and subsequently enchanted by a master. It carries 2 curses - a [Weak Complex Binding Curse] and a [Weak Feminising Curse]. It also carries an [Aroused Spell Casting Enchantment].]

[Weak Complex Binding Curse: Latex Opera Gloves cannot be removed unless physically destroyed or hit with an unbinding spell with 250 MP cost. Dispelling the curse will cause the wearer to gain 4d6 levels of [Body Sensitivity], and the caster will gain 2d6 levels [Aphrodisiac Affected](Permanent) if they fail a Hard Wisdom Saving Throw. Physically destroying the object will cause the wearer to gain 5d6 levels of [Body Sensitivity] and 3d6 levels of [Aphrodisiac Affected](Permanent), and whomever destroyed it shall gain 3d6 levels of [Aphrodisiac Affected].]

[Weak Feminising Curse: Reduces body hair growth rate by 50%, and removes body hair in contact with it entirely. Every 24 hours, [Feminisation] Progress increases by +0.05%]

[Aroused Spellcasting Enchantment: Drawing on the sex magics of succubi and incubi, increased arousal results in a discount on mana cost of demonic spells. Every 100% above baseline arousal will reduce spell cost by 1 MP, spells cannot be discounted entirely and will have a minimum cost of 1 MP. Current Arousal: +124%]

Gods damn, that was a powerful set of enchants, no wonder it was made by a master. The binding curse alone was more complex than any curse he'd seen before even if it wasn't actually that powerful of an effect. He also noted that the pair of feminising curses effectively removed all body hair growth - that was good, his mistress wanted him smooth and this would allow him to not have to worry about constantly shaving in the future. As a Half-Elf he had substantially less body hair than a human, but still more than an actual elf, who would have almost no body hair at all. At least he'd inherited a lack of facial hair from his father, whoever he was. Then there was the [Aroused Spellcasting Enchantment] - that seemed like it could be pretty insane, turning fairly powerful spells into almost free casts if he were horny enough. He wondered what spells he'd learn as a [Covenant Mage].

"Raine!" His mistress said

"Sorry Mistress, I was lost in thought there."

"Put your shoes on and then follow me."

Raine grabbed his new boots, slipping them on and tying the laces.

[[Hell-Leather Boots] Equipped]

He followed her out of the bedroom, down the hallway and to the front door. There she opened the large iron vault door, and pulled it open, revealing a small vestibule of sorts. Inside the small vestibule was a hat stand, a mirror and some hooks on the wall, one of which had a leash on it. There was also a shelf with a few odds and ends on it - rope, a brush, a trowel and some other things. Leant against the wall was a large shovel. His Mistress stopped then, grabbing the leash, which was made of the black leather that she seemed to love, on one end was a loop and on the other was a carabiner.

"I'm putting you on a leash Raine." Mistress Tazamoth stated plainly. "Letting you run free when we're in Gomhisseg would probably get you in trouble, and would reflect on me very poorly. It's generally considered impolite for a middleplaner not to be on a leash if they're not fully trained yet. So you will be leashed and you will be on your best behaviour."

Raine nodded, "Understood Mistress" he said, presenting his neck to her so she could fasten the carabiner around the small loop attached to his collar.

Now successfully leashed by his mistress, he was led out of the vestibule into the outdoors. It was warmer outside than it had been in his Mistress's house, it was like a baking summer day - probably something like 30°C-35°C. A hot wind blew over the ashy landscape, blowing small particles around Raine. The sun - or maybe a sun - shone down on the landscape, yet instead of the standard blue skies, the skies were a light grey, presumably because of all the ash in the air. Ashy soil crunched slightly underfoot as he walked along, each step kicking up a small amount of grey dust. They walked pretty much directly towards the faint outline of a city, which was presumably Gomhisseg. Raine wondered what the architecture there would be like. He realised that he'd never actually been to a city in his life, as an apprentice student at the academy, he hadn't the opportunity to travel much at all for his studies, so he had only visited a few small towns that were only a little bigger than the academy's campus. Of course, he'd heard from a few fellow students about what cities were like, some of them were from such cities.

He had to keep a slightly faster than normal pace in order to keep up with his Mistress's long strides. They walked in silence for a little while, Raine taking in the scenery as they went. Eventually though, his curiosity got the better of him and he started asking his Mistress questions.

"Mistress?" he began

"Yes Little Raine?"

"You said before that in hell, eating is unnecessary. If that's the case why do you have a kitchen and a Dining Room?" He asked

His Mistress actually looked a little nervous at that, "Just because Demons don't have to eat doesn't mean we don't enjoy it. It's a matter of prestige to be able to serve guests fresh food in a plane where nothing grows and no animals live, even if it disappears the second it enters their stomach. The dining room also acts as a good social space and meeting room."

"You regularly bring food from Middleplane to Hell Mistress?" Raine asked in disbelief, on Middleplane even nobles struggled to get extraplanar items frequently, and whilst Raine knew his Mistress was a fairly powerful Demoness, she wasn't a noble by Hell's standards - that title being reserved to those over level 100 - this Raine knew from his study of Demonology.

"No..." His Mistress trailed off slightly. 

"I don't understand Mistress." Raine said.

His Mistress sighed, "I suppose I might as well tell you now and get it out of the way. Raine... I eat people."

"Huh? I was taught that was a myth in the academy." Raine felt confused.

"It is, in Middleplane. We have no reason to there, since farms actually work. In hell, we often eat sapients who have been rejected from heaven and condemned to suffer for all eternity down here. I mean, it's our job to torment them and we don't even get any XP for it. Plus, all the bodies of the respawning condemned have to go somewhere, might as well make it more comfortable for us whilst we torture them. Unlike what some religions up in Middleplane will tell you, it takes a lot to get sent to hell. Every deity has to unanimously reject you and most of them are at least somewhat benevolent, so pretty much everyone sent to hell is an unrepentant Serial Murderer or Rapist or some other horrid individual."

"Oh right, I suppose when you put it like that it's not too bad" Raine said "some in the Middleplane say you abduct and eat live babies".

"You're not upset about the fact that I literally eat other sapients?" His Mistress asked incredulously.

"I mean they got sent to hell to suffer eternally." He responded.

"Raine I can literally tell you what Half-Elf tastes like." She said, sounding exasperated.

"Do you want me to be upset about you eating people?" he asked. By now, the pair had stopped walking and were just stood facing each other.

"No... I guess I was just worried that you'd hate me after that and I'd lose the loyal covenanter I cared about..." She confessed, sounding very human and vulnerable in that moment.

"You care about me?" Raine asked surprised.

"I- Yeah." She said.

"Oh, I care about you as well... Sorry for asking about the food then, Mistress." He said.

'Mistress cares about me! And beyond just my worth as a plaything.' he thought to himself with elation.

"Don't be Raine, you aren't stupid and would've figured it out eventually. Besides, I couldn't have guests over for dinner and not show off my new covenanter, it just isn't done. You'd definitely figure it out by then." She paused. "I suppose I should also tell you that Hell-Leather is made from people's skin, and that the Latex you're wearing is made from Dryads. Hell, even Blacksteel is made from Iron extracted from blood."

"Oh cool, I see. Can I ask another question Mistress?"

"You may, my Little Raine." His mistress said, back to her confident and domineering self.

"If residents of hell don't need to use the toilet, why do you have one in the Bathing room?" He asked.

"Oh, that one's simple. The bathroom there is for doing drugs in." She said.

"What?"

"I'm being serious. Sometimes guests want to take illicit substances and I'd rather them do it somewhere where I know to clean rather than find leftovers of it in my vestibule. This is hell, Demons are all chaos-aligned and we can't die from an overdose, recreational drug use is pretty strong here. Myalenphor - my head maid that is, I'll introduce you to her eventually - says it also adds a certain je ne sais quoi to the Baths as well. Though she's a hypocrite because she's definitely been hooking up with one of my business partners in there." Mistress Tazamoth rambled on.

"Oh" was all Raine could muster at the explanation.

"Do not tell her that I know what she's been doing in there. I think it's cute that she's in love and they do seem to get along well. She's nearing Greater Demonhood, so she'll be leaving my service soon and I don't want our last few months together in the household to be awkward, stilted and mistrustful." She commanded.

Raine nodded.

"Let's go Raine. We can continue talking whilst on our way to the city. We really shouldn't be late." Mistress Tazamoth said.

"Okay Mistress." Raine said as he felt her yank on his leash.

"Do you have any more questions for me Little Raine?" She asked

"Yes Mistress. When does [Mandrake-Drunk] wear off?" Raine questioned.

"Oh, it takes about a day and half for it to wear off, it'll probably happen tonight while you're sleeping."

"Right thank you mistress." Raine said. "Could you tell me where we're going that you're so concerned about being late to arrive to?"

"I'll tell you what Raine, since you were such a good boy about the food reveal I'll tell you a little." She said teasingly. Raine squirmed under her praise, flustered by it.

"I may have booked some appointments in Gomhisseg when I was out a couple days ago. There's some stuff I want to get you that requires you physically be there. The first appointment is one at a piercing place, we're going to get you some piercings. The other appointments are surprises though, I want to see your reaction to them." Mistress Tazamoth explained. "Unfortunately, tomorrow I'm required to partake in some summonings. Sadly even as a Greater Demon I can't escape doing some work. I'll probably be back that night but if I'm not you have full permission to keep yourself busy within the house."

"Thank you Mistress." Raine responded.

"No problem... Oh! And, Raine? Not a word of our earlier conversation to anyone." She commanded.

"Yes Mistress."

They carried on walking through the ashen wastelands in a comfortable silence. Raine's Mistress occasionally tugged on the leash to get him to hurry up as they went. Eventually, they came to an actual paved road of a reddish stone which they continued along. Soon, they came to the edge of a fenced-in brick facility. The acrid smell of sulphur hit Raine and stuck to the back of his throat. He turned to his Mistress, who seemed entirely unbothered, throwing her a questioning glance.

"Oh, that's one of the places we punish the condemned. This one specifically is a pool of liquid sulphur, its for those who took great pleasure in promoting others to suicide. Honestly these ones aren't much use in terms of resources. So we just erect a wall around the pool and have a few lesser demons on stand-by to kill anyone that looks like they're actually going to successfully get out - usually though they actually drag each other back in trying to escape the pool. Crab Bucket Mentality I suppose." She shrugged.

"You aren't bothered by the sulphur Mistress?"

"No, Demons don't have the aversion to sulphur that most Middleplaners do. Anyway, we're almost at Gomhisseg now, so remember what I said about behaviour." She said.

It was true, Raine could start to pick out individual buildings in the city behind its walls. He estimated they only had about 5 minutes before they reached it. They carried on walking. When they arrived, the gate was open, so his mistress led him in on his leash. He blushed as he saw another succubus look at him with barely concealed hunger, she was a lot smaller than Mistress Tazamoth though, probably a Lesser Demoness.

[You have entered an area of concentrated Lust!]
[[Body Sensitivity] increased in Level. Level 16 ===> Level 17]
[[Aphrodisiac Affected](Permanent) increased in Level. Level 4 ===> Level 5]

Raine was pulled through bustling streets by his Mistress. There must've been hundreds, maybe even thousands of demons along the way. Amongst them were a few dozen different middleplaners, Raine recognised what looked to be several humans, albeit of a subspecies he didn't recognise, there was also a few elves he saw, once more of subspecies he didn't recognise - except for one, a nervous-looking Wood Elf who made eye contact with him and flinched when Raine smiled at her, like him she was also on a leash, being held by a olive-skinned succubus with black hair and very little clothing. His mistress carried on, the crowds subtly parted to let her through, it seemed most of the Demons here were Lesser Demons, and his mistress represented a substantially powerful individual here. Raine looked up at he thought was a sign for a tavern or maybe a brothel and realised that he couldn't speak or read Enochian, the language of demons. Sure he recognised the script - the academy had taught him that much at least, but the Enochian language classes were Journeyman-students only, so he'd never had the chance to take them. He'd have to rectify that at some point he thought as they continued walking. Soon, they came up to a street that lead to a second wall that seemed to form a barrier between the centre and the outer section of the city they were in now.

"That's the Middle City. Unfortunately, partially trained middleplaners aren't allowed in there, and mostly Greater Demons live there. Otherwise I'd take you to a couple places there for some more things. Thankfully, the piercing place we're going to is built right up against the wall though, it's just around the corner." Mistress Tazamoth said.

They turned the corner, and his mistress guided him to the third building along the street. It had a wide glass window covering much of the front of the first floor, laid out in several cases were all manner of jewelery - mostly for piercings, but there was also a couple necklaces and rings most curiously. Several chairs were lined up in the building, and several lesser Demonesses stood around them - clearly the piercers. Behind these was what looked like a staircase with a railing leading down into a basement. Mistress Tazamoth pushed the door open and a bell ringed as she pulled Raine in using his leash. A Green-haired Demoness emerged from the basement, like his mistress she was very tall, standing at least 6'7 without her horns, maybe reaching 7 foot with them. She smiled at them both revealing shark-like triangular teeth very much unlike his Mistress's vampiric style teeth. She wore very little, a small black bikini top that did little to hide her tits or the large barbells pierced into her nipples and, black denim shorts, her legs were clad in fishnets but were otherwise bare. She was also adorned in just about every piercing imaginable, Raine counted 7 on one ear before she turned towards his Mistress and he could no longer see that ear. She started speaking very very quickly to his Mistress and Raine was once more reminded of the Enochian language lessons he never got to attend.

-----------

Tazamoth's POV

Tazamoth pulled Raine into the small building that made up Azzadzime's Premium Piercings, the bell on the door ringing. In no time at all, her fellow Greater Succubus came up the stairs. Azzadzime had done her nipple piercings some 70 odd years ago now, and Tazamoth was only now considering getting some more.

"Ah Tazamoth, you little hellion, you're back. You know when you came into my shop asking for some covenanter piercings as quickly as possible, I nearly didn't believe it! I mean, after not seeing you for 70 years seeing you in front of me as a Greater Demon was quite the shock. In my mind you'd gotten subsequent piercings at one of my rivals but it turns out you'd never gotten another piercing after you came to me. I still tell my apprentices about how you came in as a level 12 Succubus just barely out of imphood with your first paycheck for soul-collection and literally threw the money at me, a Greater Demon and demanded nipple piercings and enchanted barbells only to realise that you did not have enough money for even my cheapest enchantments after the piercing. I still laugh about that now but you're only like 10 levels away from reaching my own level now. That's why I, like, agreed to open shop 30 minutes earlier today for you. I don't suppose you're throwing my payment at me today?" Azzadzime spouted, not even pausing to take breaths.

"You remember that?!" Tazamoth exclaimed horrified at the idea of someone remembering her embarassing prior behaviour.

"Of course I remember that darling! Why I was just telling my newest apprentice Kharatooyi about it last week! Now look at you splurging on a new covenanter. Is he your first? If not, how many others do you have? Also how did you get the sort of money to throw around on a new covenanter like that? I'd hesitate to spend that much on any new covenanter of mine, and I'm amongst the richer of the Greater Demons in this city. But you've got him in a bunch of multi-curse equipment!" Azzadzime bombarded her with questions.

"Not much to say really, I was just lucky and managed to get summoned by a greater immortal a while back and managed to convince her to sell her own soul and got her to convince most of her several hundred employed servants to sell their souls to me as well. I have no idea what she was thinking but apparently she'd narrowly defeated a Demon Lord a couple days before summoning me, he laid some sort of curse on her which must've been affecting her judgement. That's all their is too it Azzadzime." Tazamoth answered.

"That's some great luck, but don't downplay your own skill. Still, you didn't answer my questions about your leashed man. Is he an elf? What's his name? How'd you convince him to put on a cursed chastity cage when he's such a low level? Sorry, I know I shouldn't really use [Identify] on other people's covenanters because it's rude but I was really curious, like really really curious, you know? And a butt plug too, I thought most middleplane males were scared of anal? One of my friends had a male covenanter who told her he'd rather die than let her even touch his ass, she had to let him fuck her whenever he liked for a full week before he even let her put a finger in there. Of course, he's a total buttslut now I heard but that's beside the point because he's like level 89. Also, please just call me Az, we're peers now, and you, like, aren't throwing coin purses anymore, so you get to call me Az now. But yeah, what've you done to him that's got him looking at you like you hung the stars and letting you just put stuff in his ass and stuff." The excitable woman spewed out in a barely coherent speech.

Tazamoth sighed. Clearly Azzadzime was not going to be slowing down today.

"Thanks Az. No, My Little Raine here is a Half-elf and my first covenanter. He wanted the cage on, didn't even say a peep about it going on. Same with the butt plug. He's just like that I guess, just really pathetic and he gets off on it, I really love that about him. I don't know what I did to deserve such a lovely little covenanter, but I'm glad he's mine now. Honestly it worries me a little how accepting of it all he is, he was a demonology apprentice so he knows a fair bit more than most new covenanters do. He literally let me bite his neck before our covenant even formed." She said, answering her questions.

"Half-Elves are like sterile right? I am correct right? I really need to read up on Middleplane half-folk because like, I'm considering getting a new covenanter myself, my only one, an elf woman named Lucky is like Level 34 now. I told her about the whole 'Actually demons do eat people' thing a few years ago and like she wasn't even angry, just a bit scared that I was preparing to eat her. I explained we only ate the condemned and she forgave me after like 2 hours. But yeah she's definitely ready for a new covenanter to be introduced and like, not freak out about being replaced or something. Honestly, I don't get why so many Middleplanar cultures are so obsessed with monogamy. Like if you cant lay pipe on 2 bitches thats a fucking skill issue. Are you thinking of getting another covenanter?" The older demoness rambled.

"Yeah, all male half-elves and most female half-elves are sterile. I might get another covenanter eventually I guess, but I'm not actively looking for one currently, and probably wont for some time, I'mreally enjoying it just being me and Raine right now. And it's funny you should mention the eating people thing..." Tazamoth trailed off.

"You told him?!" Az practically shrieked. "But he's only level 3! How's he not cowering away from us or trying to kill us or something?"

"I dunno. I was really nervous about it though, because he's smart and I was worried he'd like hate me when he found out." Tazamoth said, trying to act casual.

Something must've betrayed her to Azzadzime though because she turned unusually serious.

"Say Tazamoth, why don't we go to my office downstairs to go over your payment." She said, her tone leaving no room for argument.

Tazamoth followed Az down the stairs to her office. She sat down in her chair, Tazamoth stayed standing.

"You love him don't you?" Az asked.

"What?! No! I don't love... oh my gods I love him."

"You didn't realise?!" Az spat out.

"No!? I love him romantically Az, what do I do? I told him I care about him earlier today." Tazamoth said worried.

"Uh, just make him your [Concubine] when he's a high enough level, dumbass. That's what any other Demoness who falls in love with a covenanter does. He would obviously say yes. He's clearly head over heels for you." The older demoness said, fiddling with one of her lip piercings.

"Right, yeah." Tazamoth said.

"You desperately need to spend more time with your peers casually Tazamoth, you're a social disaster." Az advised

"I'm not." she replied, indignant.

"Girl you're like having a fucking breakdown in an almost-total-stranger's office because you like the guy you have sex with, you're a mess and you need friends. Like do you even have a nickname instead of your long ass full name?" The woman asked

Tazamoth shook her head in response.

"Tell you what then Moth, why don't you come over to my house some time, Lucky and Raine can have a playdate and we can get to know each other." Az proposed.

"I... Sure, thanks Az, that sounds great. Moth, huh, I like it." Tazamoth replied. "Also, I was going to ask while I was here, could I buy some new barbells and book another appointment, for myself this time? I really do need to rectify the lack of piercings."

"Sure, Moth, I'll show you what we have in stock in a bit. As for the appointment, I can get you in for a 30 minute appointment at either 8pm or 8:30pm in 6 days time. Since I close at 9, you could bring Raine and we could have our hangout when I'm done piercing you." Az said

"Yeah that sounds great. I don't suppose I could book both slots. There's a lot of piercings I want to get."

"Sure. I'm assuming you can like, easily afford it?" Az asked.

"Yeah" Tazamoth responded.  

"Right, we should probably head back up so we can get started on the piercings you wanted for Raine. Three Helixes, a septum piercing and 2 Lobe piercings right? The right ear is getting 2 helixes whilst the left is getting one, yes?

"Yeah." Tazamoth repeated.

The pair walked back upstairs to start the piercings.

-----------

Raine's POV

His mistress returned from downstairs with the demoness who he presumed was the owner. He was soon maneuvered into a chair. By his Mistress and the other large succubus.

"Mistress Azzadzime will start piercing your ears now, little Raine. You're getting 2 in the left ear and 3 in the right." His mistress said.

Rained nodded in understanding as the tall succubus, Azzadzime, returned with a rather wicked looking set of needles. She grabbed his left ear and Raine felt a sharp pain as she drove one of the needles through his ear lobe.

[A [Succubus] has stabbed you! -1 HP]

She placed a small metal bar in the wound, which Raine assumed was temporary. She moved up slightly, grabbing the top of his ear before that sharp pain returned.

[A [Succubus] has stabbed you! -1 HP]

The woman moved around behind him, now on his right side, she grabbed his other ear.

"You're being such a good boy Raine." His mistress said.

[A [Succubus] has stabbed you! -1 HP]

[A [Succubus] has stabbed you! -1 HP]

[A [Succubus] has stabbed you! -1 HP]

"Just one more now Raine." His mistress said

The other Demoness grabbed his face now, maneuvering her needle towards his nose. Rained felt the needle pass through his septum.

[A [Succubus] has stabbed you! -1 HP]

"All done Raine." His Mistress said.

Azzadzime cast a spell.

[A [Succubus] has cast [Heal Piercings] on you.]

Rained felt each of piercings close up, and then Azzadzime began removing the little metal bars, leaving behind well-formed piercings.

"Now little Raine, why don't we put some jewelry on for you." said Mistress Tazamoth, being handed a small box by Azzadzime.

She opened the box, revealing several earrings and a nose ring. She grabbed the first one, a simple stud made of blacksteel and put it in his left earlobe.

[[Cursed Blacksteel Earring (Stud)] Equipped!]
[[Cursed Blacksteel Earring (Stud)] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Earring (Stud)] Secondary Curse Activated: Increased Consequence Curse!]

Before he could even look at the description, his Mistress inserted a second stud into his other earlobe.

[[Cursed Blacksteel Earring (Stud)] Equipped!]
[[Cursed Blacksteel Earring (Stud)] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Earring (Stud)] Secondary Curse Activated: Cock Sensitivity Curse!]
[Permanent Effect Gained: Cock Sensitivity]

Next came 3 rings, inserted into his new helix piercings.

[[Cursed Blacksteel Earring (Ring)] Equipped!]
[[Cursed Blacksteel Earring (Ring)] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Earring (Ring)] Secondary Curse Activated: Aphrodisiac Addiction Curse!]

[[Cursed Blacksteel Earring (Ring)] Equipped!]
[[Cursed Blacksteel Earring (Ring)] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Earring (Ring)] Secondary Curse Activated: Frustration Curse!]

[[Cursed Blacksteel Earring (Ring)] Equipped!]
[[Cursed Blacksteel Earring (Ring)] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Earring (Ring)] Secondary Curse Activated: Aural Weakness Curse!]

Raine wondered what each curse did. He resolved himself to look at each curse's description later. Finally, his Mistress inserted a nose ring into his septum piercing.

[[Cursed Blacksteel Nose Ring] Equipped!]
[[Cursed Blacksteel Nose Ring] Primary Curse Activated: Binding Curse!]
[[Cursed Blacksteel Nose Ring] Secondary Curse Activated: Mental Weakness Curse!]

That last curse looked pretty strong. He wondered what its effects were. Presumably it made him weaker to a Succubus' mind altering effects, but how exactly?

"Good boy Raine." His Mistress said. "I'm just going to buy myself some new enchanted barbells, then we'll be off."

"Okay Mistress."

Mistress Tazamoth started speaking to the tall Demoness again in Enochian.

-----------

Tazamoth's POV

"It was 17 Groats, 2 Pennies and a Half-penny I owed you right?" she asked Az.

"Yes, plus the cost of whatever new barbells you decide on getting." Az affirmed.

"Well I'll hand over that now, then pay for those once I've decided." Tazamoth, no, Moth responded.

"Sounds good 'Moth. I assume you want something from our Domme line? Oh, theres these new ones I made that forces any Middleplaner with smaller tits to gain [Sexual Frustration] when they look at yours and fail a wisdom check. Wait, that one only like, works on females, nevermind. Ooh! There's these real cute ones that are attached together with a chain and you can like, put a ton of little enchanted items on them. And then there's one that makes your tits bigger. I mean like, you've already got some pretty massive ones but imagine if those fuckers were enormous or whatever? Like, I tried them out on Lucky and her tits got gigantic. I've also got some more basic ones that like increase sensitivity and stuff." Az rambled on.

"I think I'll just take a look and see what I fancy, Az." Moth said, as Az continued on her deranged and horny rant.

She scanned her eyes across a row of piercings labelled 'Enchanted Barbells (breasts)', reading the small descriptions of each one until she found one that she liked. Her eyes fell on one labelled 'Breast Obsession Enchantment', this one sounded pretty interesting at least. She read the description.

Breast Obsession Enchanted Barbells: These Barbells inflict 1 level of [Entranced] on observers every minute up to a maximum level of 50. Observers will become unusually obsessed with your breasts. 5 Pence.

Perfect. Raine was yet to show much appreciation to her tits, being much more focused on her pussy and cock. Clearly, this would help him to appreciate all of his mistress.

"I'll take these ones Az" she said, pointing out the Breast Obsession barbells.

"Ah, good choice, I hope you and Raine enjoy them. By the way, do you have anything else planned for today? Have you considered getting him other forms of body modification. I know pretty much every body modifier in this city, I'm sure I could like, find something for your Raine if you'd like, you know? Oh and by the way Moth, do you plan on teaching him any Enochian? I don't speak any Inglese and I don't pick up languages like you do, and the same is true for a lot of Demonesses. Him being able to speak Enochian would probably be pretty useful for him. But yeah also I can't wait to hang out with you later girl. It'll be great fun. We could drink if you like?" Az said with such speed that Tazamoth could barely understand her.

"Yeah, I've got to go take him down to the registry so I can get some time off summonings to train him. Sadly I've got to attend some tomorrow, but I'm hoping to get the next 2 or 3 weeks off so I can get him to the point where I can start bringing him with me to the Middleplane. After he's registered I'm taking him to get a proper womb crest tattoo. I do plan on teaching him Enochian eventually, but I want him a bit more physically developed before we move onto cultural stuff. As for the drinks, sounds good to me, I'll bring some bloodwine." 'Moth said.

"Oh, sounds good. Don't let me keep you though. Go take your pet-man-thing to his other appointments as well then." Az finished, turning around to talk to a lesser succubus that was cleaning her tools.

Tazamoth gave Raine's leash a quick tug and they left the piercing shop.

-----------

Changes this chapter:

[Special Trait Progress Increased: Feminisation: 1.3% ===> 1.9%]

[Permanent Effect Gained: Cock Sensitivity: Level 1]

[Permanent Effect Increased: Body Sensitivity: Level 14 ===> Level 17]

[Permanent Effect Increased: Aphrodisiac Affected: Level 4 ===> Level 5]

[Permanent Effect Increased: Anal Sensitivity: Level 1 ===> Level 2]

[Effect Decreased: Erectile Dysfunction: Level 2 ===> Level 1]

Chapter Text

Raine's POV

Raine let his mistress pull him through the streets once more, leading him towards an official looking building a couple blocks away. By now the Butt Plug in his ass was making each step rather erotic and most certainly pleasurable. His mistress walked him inside the building, stopping by the wall in the foyer to tie his leash to a metal ring on the wall with a small placard above it that Raine was pretty sure said 'Covenanters' on it.

"Raine, I'm just going to register you as a covenanter, so I can take some time off of being summoned to train you fully. Be a good little man-thing for me okay?"

"Okay Mistress." Raine responded.

With that, his mistress left him and started talking to the receptionist at the front desk. With nothing else to do, Raine decided to start reading through the curses of his new jewelery which now sat snugly in his still slightly sore piercings. First, he looked at the curses on the studs.

[Increased Consequence Curse: Any time you gain levels of an effect from a Consequence, gain an additional level of the effect.]

[Cock Sensitivity Curse: Every time you reach orgasm through use of your cock, gain 1 Level of [Cock Sensitivity] up to Level 100.]

[[Cock Sensitivity](Permanent) - Your penis becomes 1% more sensitive per level.]

The [Increased Consequence Curse] looked like it could lead to some pretty large increases in the levels of his effects. Honestly Raine felt quite excited about the prospect of failing again and facing even more consequences. The [Cock Sensitivity Curse] and it's accompanying trait seemed to mirror the [Anal Sensitivity Curse] his butt plug had, which was cool but he was hoping for a more unique curse. Onto the Helixes then.

[Aphrodisiac Addiction Curse: Failing to have aphrodisiacs applied to you for 24 hours will cause you to gain 1 level of [Sexual Frustration] and may have side effects.]

[Frustration Curse: Failing to orgasm or induce an orgasm for 24 hours will cause you to gain 1 level of [Sexual Frustration].]

[Aural Weakness Curse: You are substantially more susceptible to Aural attacks. All effect caps of auras are doubled when affecting you.] 

Oh wow, these were pretty unique, the [Aphrodisiac Addiction Curse] and [Frustration Curse] practically meant that he'd gain 2 levels of [Sexual Frustration] every day he wasn't with his Mistress. The idea turned him on greatly. He still had the nose ring's curse to look at as well.

[Mental Weakness Curse: Gain disadvantage on all Wisdom and Intelligence Saving Throws made against a faction member.]

This was a pretty simple curse but Raine was careful not to underrate it, combined with his [Entranced] effect, he'd now pretty much always fail Wisdom and Intelligence Saves against his Mistress, meaning she could turn him into a proper slut even quicker. Raine couldn't wait until they got home, he hoped his Mistress would finger him again, he'd try his best to cum this time. He looked over at his Mistress, her back turned to him as she filled out some sort of paperwork that she had been handed by the receptionist. Raine stared at her ass, despite it feeling a little crude to do so, her black leather shorts did little to hide the form of her figure, a figure that had Raine day-dreaming of all sorts of naughty things she might do to him tonight. A slightly sticky feeling in his shorts alerted him to the fact his small caged cock was leaking as he thought up all these lewd thoughts. Images of His Mistress's amazonian dick entering his tight little asshole flashed through his mind, keeping him entertained as his Mistress worked through forms and disclaimers.

[[Entranced] increased in level. Level 5 ===> Level 6]

[[Heightened Submission] increased in level. Level 5 ===> Level 6]

After 15 minutes, his Mistress returned, untying his leash and leading him outside once more. His ass erupted in pleasure once more as the movement jostled the butt plug in him. She lead him back out onto the street, down towards the city gate they had entered through before turning left into a side street. There a slightly dodgy looking stood bathed in a strange pink light. Bold lettering and a large pen-like device were displayed on a sign on the front of the building. Raine guessed this was his next appointment. When his mistress opened the door and pulled him inside with her, his suspicions were confirmed.

Unlike the outside of the building, the interior was well lit with white light. Several reclining chairs and cabinets dotted the room they entered into. Another Greater Demon welcomed them, speaking to his Mistress in Enochian. She was about the same size as his Mistress, but was much leaner and had extremely long white hair. Most noticeably however, she was entirely nude showing off her entire body. Her skin from the neck down was covered in all kinds of tattoos that [Dangersense] warned him about. He watched as his Mistress conversed with the other Demoness.

"Ah, Tazamoth was it? Yes, I'm ready to start tattooing Raine now." She said.

"Thank you Miphiette, that would be preferable Raine here has had a long day and is probably quite aroused right now, I'm sorry if he cums during the tattoo." Tazamoth said.

"Oh don't worry about that, it happens all the time with new sissies that come to get a tattoo, so long as he's not actively trying to fuck me as I'm tattooing him it'll be fine." the Demoness Miphiette answered.

"Raine's a good boy, rest assured he'll leave you alone."

"Awesome, just tell him to take his shorts off and sit in this chair." Miphiette replied.

Raine saw his mistress turn towards him, leaning in close to his face.

"Ok Raine, Miphiette here is going to give you a tattoo that'll mark you as mine and it'll have some nice effects on you. Now be a good boy and take off those shorts and your thong for mistress." She said.

Raine complied, pulling down his shorts to reveal a sticky mess of precum smeared over his caged dick, thong and pubic region. He carried on, removing his thong.

"Oh, did my little man-thing make a mess in his slutty pants?" Tazamoth said. "Well why doesn't my soon-to-be-sissy go sit in that chair so Miphiette here can start on that tattoo then?"

Raine moved onto the black leather reclining chair, feeling surprised as the nude Demoness strapped him in by his ankles and wrists. His academy had a zero tolerance policy on tattoos, but he'd heard they could be quite painful. If the restraints were indicative of anything, this was likely going to be a very painful experience. Still, he'd go through it for his Mistress. Mistress Tazamoth stood behind him, leaning forward against the back of the chair. He felt Miphiette apply some sort of stencil just above his waistline, Raine couldn't see exactly what the stencil looked like because of the chair's reclined position.

Miphiette picked up her tattoo machine, and it sprung to life, Raine detected magic and [Dangersense] went utterly wild - whatever it was exactly was apparently dangerous. She brought the machine down, making contact with Raine's skin and several needles pierced Raine's skin. Pain hit Raine near-immediately, and the Half-Elf found his eyes watering just seconds into the process. It hadn't occured to him before that [Body Sensitivity] would also increase his sensitivity to pain, but now that he was getting this tattoo, it was made pretty clear that it did in fact include pain into it's increased sensitivity. Fortunately, Miphiette seemed to be a pretty fast worker, moving the machine quickly across his waist as she went about completing an outline of whatever design his Mistress had chosen for him.

"By the way Tazamoth, if you want him developing more masochistic tendencies, you should talk dirty to him and maybe toy with his cage a little whilst you're at it. A lot of Mistresses have found that toying with their covenanters whilst I tattoo them is a good way to get them started into masochism and more extreme kinks." Miphiette said, halfway done with the outline of the womb tattoo.

"Good idea, thanks Miphiette." Tazamoth said.

Between the language barrier and the stinging pain of his waist, Raine had no idea what the two Succubi were saying. His Mistress moved to his side, running her right hand through his hair, and patting his caged cocklet with her left.

"It hurts Mistress." Raine said.

"I know Little Raine, but this crest will make you more feminine. That's why you need it, because you're a dirty little Man-thing who needs to be trained into a proper femboy for his Mistress."

"I know Mistress, I'm sorry Mistress" Raine said as he scrunched his eyes shut through the pain.

"Good boy Raine... Do you know what Good Boys get Raine?"

"No Mistress."

"Good Boys get kisses from their Mistresses Raine." His Mistress said. She leant in, grabbing his head and kissed him, her long slimy tongue forcing its way down his throat.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level! Level 17 ===> Level 18]
[You ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] could not increase in level! (Cap)]

Raine felt the pain of the tattoo increase slightly as [Body Sensitivity] increased in level. He let out a moan, though he wasn't quite sure if it was of arousal or of pain. His mistress smiled hungrily. She moved her left hand back to his crotch, this time cupping his balls, squeezing them gently. Slowly, she started squeezing them harder and harder, causing Raine to go from feeling pleasure to discomfort to pain. A couple tears streaked down his face by now.

"Mistress please." Raine begged.

Mistress Tazamoth stopped squeezing his balls in her hand, giving Raine a brief sense of relief from some of the pain. He sighed out a shaky breath.

"Not even a 'Thank you Mistress'? How rude Raine. Men-things like you should be polite to their Mistress. Will I have to punish you as a reminder?" She degraded Raine.

"No Mistress, I'll be a good boy." Raine pleaded

"Hmm... I'm not sure I believe that one." She said sadistically. Sensing what was coming, Miphiette lifted her Tattoo Machine, now nearly done with the outline. She took her hand off his balls, pulling it back and smacking his genitals hard. Raine cried out in pain and pleasure, more watery precum leaked out of his abused little penis. Raine felt something in him snap as he got a notification.

[Permanent Effect Gained: Pain into Pleasure] 

He looked at its description, desperate to take his mind off the pain of the tattoo and his battered dick and balls.

[[Pain into Pleasure] - 1% of pain per level is also felt as sexual pleasure. Current Level: 1]

Oh wow, that was pretty good, whilst it didn't look like it decreased his pain, it did at least give him another way to take his mind off of the pain. His mistress was back to squeezing his balls now, and he could feel the slightest tinges of pleasure to each slightly painful squeeze. Miphiette returned her Tattoo Machine to its position and returned to completing the tattoo. The pain was immense but it now carried the barest aftertaste of pleasure, and Raine found himself whimpering in pleasure in between sobs of pain. After another couple minutes, Miphiette had completed the outline and moved onto filling the tattoo out.

[Gained Special Trait: Succubus Covenant Crest (Incomplete): Current Effect(s): None]

Raine though he could make out the the feeling of letters being written onto him through the pain of the process. He felt himself retreating into himself as the pain increased as the tattoo started to get filled out. He felt his Mistress stop squeezing his poor nuts, but he felt himself beginning to pass out from the pain of it all.

"-aine. Raine!" his Mistress shouted at him

"Huh? What?" he asked dazed

His Mistress slapped him across the face hard. Raine's cheek stung as he turned to look at her.

"Not 'Huh? What?', it's 'Yes Mistress?', are you so soft that a little pain makes you forget all your manners?" She questioned him imperiously. 

"Yes Mistress, s-sorry Mistress. Please p-punish me for... for being a bad boy M-Mistress." Raine cried.

"Good boy, now hold still." she warned him. Miphiette stopped tattooing him.

She grabbed his balls and squeezed hard, Raine felt like his balls were going to be crushed. A wave of pleasure hit him and his cock dribbled out precum onto the chair.

[[Pain into Pleasure] increased in level. Level 1 ===> Level 2.]

[[Entranced] increased in level. Level 6 ===> Level 7]

[[Heightened Submission] increased in level. Level 6 ===> Level 7]

Raine started crying properly then. Miphiette, unphased, returned to tattooing him, finishing off filling out the section she had been working on. She moved down, to just below the waist line, starting to fill out a new shape.

[Special Trait Modified: Succubus Covenant Crest (Incomplete): Current Effects: Levelling, Loyalty.]

Raine read the description through teary eyes.

[Succubus Covenant Crest (Incomplete): Gains a level every time your Mistress makes you cum. You are 1% more loyal and obedient to Mistress Tazamoth per level. Current Level: 0] 

Raine struggled to come to much of an opinion on it through the pain, especially since it was mostly incomplete at the moment. The pain was making it hard to think.

[[Pain into Pleasure] increased in level. Level 2 ===> Level 3]

More precum pathetically dripped down from Raine's ensnared cock, leaving behind sticky trails of shiny fluid on his thighs, which were soon spread across his thighs as he twitched in arousal, giving them a general slimy sheen. His mistress started running her gloved hands through his long dark hair again, whispering praise into his ear. She reached down once again, this time simply jiggling his cage, and with it his abused balls. Lust started creeping through nauseating pain and he let out a little moan, which got his mistress's predatory smile focused back on his face. She slapped him again, lighter this time, eliciting a small mewl from the beaten Half-Elf. At this point, Miphiette finished filling in whatever small section of design she'd been working on as Raine got a notification.

[Special Trait Modified: Succubus Covenant Crest (Incomplete): Current Effects: Levelling, Loyalty, Arousal Amplification.]

[Succubus Covenant Crest (Incomplete): Gains a level every time your Mistress makes you cum. You are 1% more loyal and obedient to Mistress Tazamoth per level. Arousal increases by 1% each level. Current Level: 0]

His mistress spoke up. "I think we're done here for now. Raine's on the verge of passing out and I don't want him damaged. Could I book a time to return and get the crest finished?"

"Oh yeah totally. I was going to suggest stopping here or after the next heart anyway. He's a lower level than most of my clients, so it makes sense he couldn't handle the tattoo machine for very long, since it's designed to promote masochism in level 20 covenanters, never mind whatever low level he is. I've got a slot open in 5 days time, it'll cost 3 pence to book again. In the mean time, try and get him to level masochistic effects. That way he can last a bit longer."

"Of course, he gained 3 levels of [Pain into Pleasure] in this session, I'm sure I can get him to a much higher level by then. Thanks for putting up with the impromptu Sadomasochist torture session." Tazamoth said.

"No worries, I'm not one to shy away from public displays of sex. I've got to admit it was pretty hot to watch. Besides I've seen some pretty kinky shit occur while tattooing covenanters. A bit of Cock and Ball Torture and some precum is barely worth writing home about at this point." Miphiette admitted.

"Really, what's the craziest shit you've seen then?" Tazamoth asked.

"Some Demoness came in and had me tattoo some gagged, bound and blindfolded gnome woman whilst she repeatedly hit her clit with a whip." Miphiette said seriously.

"Damn, well I'd best get Raine back home now. Here's the 3 pence for the next session." Tazamoth said, handing over 3 silver coins that materialised in her hand.

"Come on Raine, let's go. Put your clothes back on." She commanded.

"Mistress? Did I do something wrong? I'm sorry I cried like a little bitch. I'm sorry I'm pathetic Mistress." Raine said, working himself up towards another sobbing episode.

"Shhhh Raine, you did good darling. That Tattoo Machine is supposed to hurt even level 20 covenanters, I didn't expect you to sit through the entirety of the tattoo getting done in one sitting. You were a good boy and obeyed Mistress to the best of your abilities today. That's all I can ask for. Next time you'll do better and maybe get the Tattoo finished. How about we go to one last shop and buy you a present huh? For being a good boy for Mistress?" She coddled him.

Raine felt his mood improve as his Mistress sweet-talked him while he got dressed. "Okay Mistress. Wh-Where are we going shopping?"

His mistress giggled as she lead him out of the door, "A sex shop of course, my Little Raine. I'll let you chose out a new toy for us to use tonight."

"Thank you Mistress."

The pair walked in comfortable silence, Mistress Tazamoth holding a tight grip on his leash. Raine was pretty obviously aroused, precum trailed from underneath his shorts out down his thighs and then over the latex of his bound thigh-highs. After 5 minutes of immensely erotic walking thanks to the pain of his tattoo and the butt plug in his ass, Raine and his Mistress finally reached the sex shop - Syolhotep's Sadomasochistic Supplies. They walked inside and Raine was confronted with a massive collection of sex toys. Across the walls were rows and rows of dildos, some of which were frankly ridiculous, surely no one could fit that 2 foot equine dildo inside them? Then there was a shelf full of different hand cuffs, a shelf for butt plugs, two shelves for lube. But what drew his eye was a retail bin full of whips. He pointed it out to his Mistress.

"Mistress, can we get a whip? I... I uh- I liked it earlier when you were hurting me. Especially now that I have [Pain into Pleasure], I can level that and next time we get my tattoo done, I'll be much better." He asked.

"Are you sure Raine?" Mistress Tazamoth asked.

"Yes Mistress. I want you to hurt me Mistress, I want you to abuse my little penis and balls with a whip real bad." Raine affirmed

"Very well then, let's get that one there, it matches our aesthetic best." Mistress said.

His mistress approached the cashier, buying the whip whilst Raine blushed behind her. They left the shop and Raine gave out a little yawn.

"Sorry Mistress." He apologised.

"Just a little further Raine, when we're out the city I'll carry you home."

The two passed through the city gates a couple minutes later. His Mistress reached down and grabbed him, carrying him in a princess carry as he finally passed out, exhausted.

-----------

Changes in this chapter:

[Special Trait Gained: Succubus Covenant Crest (Incomplete): Level 0]

[Permanent Effect Gained: Pain into Pleasure: Level 3]

[Permanent Effect Increased: Body Sensitivity: Level 17 ===> Level 18]

[Effect Increased: Entranced: Level 5 ===> Level 7]

[Effect Increased: Heightened Submission: Level 5 ===> Level 7]

Chapter Text

4 days since covenant formed

-----------

Raine's POV

[Short Rest: Healing 1d4 HP and 1d2 MP]
[Rolling]
[Rolls failed: Already at full HP and MP!]

Raine woke up as Mistress started putting him down gently onto the floor in front of her house.

"Mistress?"

"Sleep well my Little Raine?"

"Yes Mistress. Sorry for falling asleep Mistress."

"That's ok Raine, I suppose you'll just have to make it up to me, else I might have to punish you for it."

Raine felt his loins stir at that. His Mistress opened the door to the vestibule, and the walked inside, leaving Raine to follow. She detached the leash from his collar, hanging it back up on one of the hooks on the wall. She turned and closed the door behind them, before turning to and opening the door to the hallway. She walked through and Raine followed obediently, as though he were still on his leash.

"I know you're probably quite tired Raine, but there's a couple things we have to do before you can sleep. First, You've got to remove what little body hair you have, we've left that far too long to be honest. Then, I want to introduce you to my servants since I'll be gone most of tomorrow, possibly longer, and you might run into them while I'm out. After that, we've got to try out the whip. Now let's get you to the Baths." Mistress Tazamoth said.

His Mistress grabbed his hand and lead him to the bathroom. There they stripped, wading into the water, getting up to Tazamoth's knees before she stopped for a second. A razor materialised in Mistress Tazamoth's hand. She handed it to Raine, then leant down and fiddled with his cage. His cage came off, finally freeing his penis. Raine looked down at the flaccid shaft that dangled just above the water in front of him, he felt disappointed somehow that it wasn't smaller. It seemed [Feminisation] had yet to have a noticeable effect on his cock, at least whilst flaccid. He sighed, and started to run the razor across his thighs, watching as small pale hairs fell off his body. His mistress waded in deeper, sitting on the ledge around the deeper edge of the bath, watching him approvingly. Raine soon completed the parts of his thighs left uncovered by latex. He moved onto his ass then, bending awkwardly trying to get every last little hair. His mistress licked her lips as he moved onto his pubic region, shaving away the fine hairs there. Within 10 minutes, all his hair below the waist had been removed. He moved onto his upper body, here there was even less hair and after just 5 minutes he was done. He looked over at his mistress, who had apparently been masturbating while he removed yet another vestige of masculinity, one hand rubbing her crotch and the other gripping one of her breasts.

[[Entranced] increased in level. Level 7 ===> Level 8]

[[Heightened Submission] increased in level. Level 7 ===> Level 8]

"Done Raine?" she asked

"Yes Mistress, I think so Mistress." He responded in the affirmative.

"Good boy, let's get you introduced to my servants then. Not all of them speak Inglese, so I'll be speaking to them in Enochian. I'll start teaching you it when I get back from my summonings tomorrow, that way you can talk to them." She said.

"Okay Mistress. How many of them are there?"

"I keep 9 servants currently." She answered

"Oh wow." Raine said.

The two got out of the pool, his Mistress pulled him, naked out into the hallway. There, a stone-faced, white-haired succubus in a proper-looking maid outfit stood to attention. Like her hair, her skin was very pale, making her look almost doll-like, she had pink irises that flicked over on occasion to look at him. She was only slightly taller than Raine, not breaching 6 foot even with her horns but held a silent grace to her that honestly kind of scared Raine, as though she was plotting his downfall in her mind. His Mistress began speaking to her in Enochian.

-----------

Tazamoth's POV

"Ah, Myalenphor, perfect timing as always. Would you round up the rest of the maids please? I'd like to finally make introductions between my new Covenanter and you all." Tazamoth said.

"Certainly Mistress, I can have them all ready and lined up out here in 5 minutes. I've held a couple back from starting their shifts in preparation for an introduction, since I figured you'd be conducting that today. Is there anything else?" The lesser Demoness asked.

"Please tell Komianchi to try not to scare my covenanter too much." She asked.

"I'll see what I can do Mistress, but she's been a foul mood today, apparently her most recent summoning was 'boring'." Myalenphor said, sounding apologetic.

"I see. Let her know that if she acts up, I will not be pleased." Tazamoth stressed.

"As you wish Mistress." Myalenphor said, spinning on her heel and marching over to the Servant's quarters.

Sure enough, 5 minutes later, 9 Demonesses were lined up in the hallway.

She spoke to Raine, who suddenly seemed quite cognisant of his lack of clothing as another 9 beautiful Succubi stood in front of him.

"These are my servants, Raine." She began, pointing to Myalenphor, "This is Myalenphor, my Head Maid. She is in charge of the other servants. When I am out, should you require anything you are to go to her. Similarly, when I am out, you are to take orders from her as though she were me, unless they conflict with previous orders I have given you."

"A pleasssure to meet you." Myalenphor said with a slightly accented Inglese.

Next, she pointed at the demoness to the right of Myalenphor, a very tall redheaded Demoness in a scruffy and creased maid outfit. Her shoulders and arms were armoured, and it looked as though several metal plates had been stitched sloppily into her outfit herself. If looks could kill, Tazamoth was pretty sure Raine would be dead several times over by now, as the succubus wore perhaps the deadliest expression Tazamoth had ever seen. "This here is Komianchi, the Deputy Head Maid and Head of Security. She mostly makes sure random imps don't break into the building, since they're attracted to some of the magic items I have in the casting room."

Komianchi didn't say anything, just giving the covenanter a withering death glare

"Komianchi, I know you speak Inglese, speak." Tazamoth spat in Enochian

"Hmph. Hello, half-breed." the smaller demoness spat at her covenanter.

"I suppose that's better than nothing." Tazamoth sighed to herself. 

Tazamoth pointed at the next 2 demonesses, like Komianchi, they both wore armour, but were a lot more presentable. Both had pale green hair and olive coloured skin. "These are the twins Ilenthal and Ilaphie. They also work security under Komianchi. They don't speak Inglese." she explained.

The two demonesses gave Raine a curt nod, eerily in sync. 

"Then we have Kurpfanalen, my head cook and her two assistant cooks, Giraniflel and Tamiantiyen." She said pointing to three maids who each wore a large apron and cook's outfits as opposed to maid outfits. Kurpfanalen was a dark-skinned woman with black hair and an impressive set of horns - rivalling Tazamoth's own in spite of her lesser succubus status, whilst Giraniflel had a stony grey skin and black hair. Tamiantiyen had a slight blue hue to her pale skin and blue-black hair that looked like ink.

Each nodded at Raine as Tazamoth called their names out.

"Finally, we have my newest servants, Luwienphil and Amirzara. They're responsible for basic cleaning duties and report directly to Myalenphor."

Her two newest hires gave nervous waves as she spoke their names aloud. It was understandable, they were only level 13 and level 11 respectively, having been hired straight out of Imphood after Komianchi found them wandering around aimlessly outside. Tazamoth wasn't sure exactly what Komianchi had done to them when she first found them walking around together, but they immediately got busy whenever her head of security entered the room, so Tazamoth reasoned she must've done something pretty memorable to the freshly-minted succubi.

"Now then you lot, I'm sure you have questions about how you are to treat my new Covenanter. Raine here, is to be allowed free roam of the house, though you are not to let him leave it under normal circumstances. I know a lot of other Demoness' let their servants fuck their covenanters, but I have some restrictions on what you are allowed to do to Raine. You may not fuck him in the ass, or allow him to fuck you. He will be caged whenever I leave and I expect you not to attempt to remove cages, so him not fucking you should be a relatively simple matter. Additionally, I do not want any of you leaving permanent marks on Raine while I am not present. I don't want to return to find my covenanter has been damaged in my absence." She declared, pausing slightly for emphasis.

"That being said, you are free to fuck him in the mouth so long as you are not on shift and we are not entertaining visitors. Similarly, you are completely free to do anything that will leave non-lasting marks on Raine. I expect those of you who know Inglese to truthfully answer any questions he has to the best of your abilities. He already knows about what gets cooked in the kitchen. In the unlikely event he requests food, I expect you to deny him until I return Kurpfanalen." She continued. Her head cook nodded in acknowledgement.

"Some of these restrictions will be lifted down the line, but I will be relaying these restrictions to him later. So no trying to circumvent my orders or find loopholes in them. I hope this can be a learning experience in how to treat covenanters for you all, after all, I imagine some of you will be getting covenanters somewhere down the line." She concluded, her eyes falling on Myalenphor and Komianchi, who were level 48 and 46 respectively. She hoped whoever might become a covenanter for Komianchi was a hardcore Masochist, the words 'tender' and 'gentle' did not come to mind when she thought of her rebellious maid.

"Now, I will be retiring to my chambers with Raine, I expect not to be disturbed. You are dismissed." She said, the maids returning to their quarters.

She turned to her little covenanter "Come on Raine, I think it's time we do a little bit of training."

"Yes Mistress" he said, following behind her as she walked over to her room.

-----------

Raine's POV

Raine followed his mistress back into the master bedroom. His mind went back to the rather mean looking black whip - a riding crop specifically - that his Mistress had bought him for being a good boy whilst getting his tattoo. Speaking of his Tattoo, he finally looked in front of a mirror at the design. The design was a heart within a heart inside a triangle inside a circle, where the circle had two protrusions, one on either side, that looked like mix between thorned wings and fallopian tubes. Above the circle was written a single word in Enochian, Raine was pretty sure it was his Mistress's name. Most of the tattoo was only an outline, with only the innermost heart and his Mistress's name. He presumed that these were the only parts applying effects to Raine so far - which meant that soon the tattoo was going to be getting a lot stronger in its effects.

"Raine." His mistress called him over, in her hand materialised the crop she'd bought earlier, "Time to train your pain tolerance, my precious little man-thing."

Raine felt his penis rise ever so slightly, [Erectile Dysfunction] clearly was beginning to wear off now. He stood before his Mistress, bear except for the latex covering his limbs. She slapped him in the face, the move causing a stinging sensation followed by a slight feeling of pleasure.

"How was that Raine? Shall I begin with the whip now?"

"Yes Mistress, please Mistress." Raine said.

She gently slapped his cock with her crop, causing barely any pain, Raine couldn't even feel any pleasure from it.

"A demoness' purpose is to hurt begging middleplaners. That didn't seem like begging to me Raine" She said.

"Please Mistress, I want you to whip me so bad. I want you to put me in my place Mistress." Raine pleaded.

"Much better, Raine. Let's see if we can't make that lesson stick?" She said coolly.

His Mistress pulled her arm back, lining up for a powerful strike. The crop descended, striking the head of Raine's dick. Raine cried out in agony, falling to his onto his back. The cool floor doing little to stop the pain of his red-marked phallus. Tears welled up in his eyes.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 3, 2]
[You lost 5 HP!]

Raine was then hit with a wave of intense pleasure. Precum dribbled from his abused little cock onto the floor. He let out a moan as he squirmed.

[[Pain into Pleasure] increased in level. Level 3 ===> Level 4]

[[Entranced] increased in level. Level 8 ===> Level 9]

[[Heightened Submission] increased in level. Level 8 ===> Level 9]

His Mistress stalked up to him, giving Raine the sudden feeling as though he was being hunted as prey. She kicked him in the hip, flipping him over onto his front, he let out a pained groan as his cock flopped against the floor. She pulled back again, this time striking him hard in the ass, causing him to thrust into the bedroom floor, sending a wave of pain through his cock again. The pleasure came to him quicker this time, and he blushed as his cock leaked more clear fluids onto the floor.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 2, 2]
[You lost 4 HP!]
[[Pain into Pleasure] increased in level. Level 4 ===> Level 5]

Through pained whimpers, Raine managed out a soft "Thank y-you Mistress. Please K-keep... keep punishing me for being a disgusting male. Please fix me Mistress."

His Mistress struck his ass again.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 1, 2]
[You lost 3 HP!]

Pain and then pleasure jolted through his other ass cheek this time. His cock twitched slightly as pleasure slowly made its way through its abused head. He felt his mistress's strong hand on his shoulder, and was soon lifted to his feet, he was stood in front of her now, looking up between her fat tits at her face that was twisted in a sadistic smile. He felt so pathetic being restrained just by his Mistress's left hand on his shoulder. The tip of the crop now rested under his chin, forcing him to look up at her, and not anywhere else. He found himself remembering that in many ways, Demons were a human's natural predator.

"I'm going to break you Raine, leave you a sobbing little mess for me to rebuild, over and over, until you're the exact sissy slut I want. I will relish hurting you my loyal follower, my little fucktoy." she declared.

His mistress grabbed him by the neck, strong fingers pressing into his neck and underneath his jaw. She leaned in and bit him once more, over the barely healed scar of where she had first bitten him. Pained tears rolled down his cheeks as he felt her fangs sink deep into his neck but he didn't cry - why should he? His Mistress was fixing him, making him better. 

[Your Mistress, Tazamoth, used [Foolish Bite] Against you!]
[You took 1d8 Piercing Damage]
[Rolling]
[Rolled: 6]
[You lost 6 HP!]

[Beginning Hard Wisdom Save with Quadruple Disadvantage (Entranced, Sexual Frustration, Mandrake Drunk, Mental Weakness Curse)]
[Minimum Saving Roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling: 12, 14, 5, 1!, 9]
[Hard Wisdom Save Critical Failed!]
[Effects doubled!]
[You have gained 4 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity] increased in level. Level 18 ===> Level 22]

[[Plain into Pleasure] increased in level. Level 5 ===> Level 6]

Raine shook as suddenly his wounds became even more sensitive and even more satisfying, another little spurt of precum dripped out of his cock, falling on his Mistress's knee.

"Oh does my Little Raine like it when I mark him as my property? I'll have to keep that in mind for the future." She said, looking down at his sad excuse for a cock, "I really ought to put that back in its cage now, I'd love to continue this Raine, but sadly I don't think you have the HP for it, so I think it's time for bed."

"Sorry I couldn't last very long Mistress." Raine apologised.

His Mistress knelt down next to him, "You did okay, Raine. It would've been nice to hit you some more, but you're still only level 3. Besides, look at your effect gains, 3 levels of [Pain into Pleasure] and 4 levels of [Body Sensitivity] is good progress to make in just a few minutes. Now, let's put that cage of yours back on, since I'll have to be going immediately tomorrow morning, and I don't want the maids getting any ideas. They're under strict orders not to fuck you in the ass, or leave any permanent marks on you, those are things only I'll be allowed to do for now." She explained.

She summoned his chastity cage and started putting it on, the process sending more pain through his shaft. Now secured on his cock firmly, she locked the cage again. The pressure now stung sweetly, the compression on his penis hurting slightly. She snapped her fingers and the lights magically turned off. Mistress Tazamoth guided him to the bed, and he laid down to go to sleep. He felt her massive figure embrace his body, pulling him in almost like he were a teddy bear. His face just inches away from her huge tits, he fell asleep.

-----------

Changes this chapter:

[Permanent Effect Increased: Body Sensitivity: Level 18 ===> Level 22]

[Permanent Effect Increased: Pain into Pleasure: Level 3 ===> Level 6]

[Effect Increased: Entranced: Level 7 ===> Level 9]

[Effect Increased: Heightened Submission: Level 7 ===> Level 9]

Chapter Text

5 Days since Covenant Formed:

-----------

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 7]
[HP Increased: 7/25 HP ===> 14/25 HP]
[Rolling]
[Roll Failed: Already at full MP]

[Special Trait Progress Increased: Feminisation: 1.9% ===> 2.0%]
[You may now view effects of [Feminisation] on your body]

[Permanent Effect Increased: Body Sensitivity: Level 22 ===> Level 24]

[Permanent Effect Increased: Anal Sensitivity: Level 1 ===> Level 2]

[24 hours have passed since you last ejaculated! Side effects will be applied shortly!]

[[Mandrake Drunk](Level 4) became [Mandrake Hangover](Level 4)]

[Effect Decreased: Entranced: Level 9 ===> Level 8]

[Effect Decreased: Heightened Submission: Level 9 ===> Level 8]

Raine woke up sore. His neck, ass and cock all stung from where they'd been whipped or bitten. Additionally he felt utterly drained and his mind felt really hazy, which might be something to do with the fact that [Mandrake Drunk] had finally worn off and been replaced by [Mandrake Hangover]. Groaning, he looked at the description.

[[Mandrake Hangover](Temporary) - Gain disadvantage on Strength, Vitality, Agility and Intelligence checks. Sperm count decreased by 10% per level up to 100%. Additional levels have no effect, decreases one level every Long Rest. Current Level: 4]

Yeah, no wonder he felt drained and hazy, all his most physical stats and his intelligence were struck with disadvantage because of [Mandrake Hangover], pointing it out as the most probable culprit. He looked over at the notifications on [Feminisation], apparently he could now read out how the progress was affecting him. Raine was pretty pleased by this turn of events, just yesterday he hadn't been sure how much of an effect feminisation was really having. He focused on [Feminisation], bringing up the list of effects.

[Feminisation Progress: 2.0%

Effects of Progress:

-Skin softness: 102%

-Body Hair Growth Rate: 98%

-Width of Hips: 2mm increase

-Height: 2mm decrease

-Penis Length: 1% decrease (1.14mm Decrease Hard)

-Penis Girth: 0.5% decrease (0.45mm Decrease Hard)

-Testicle Size: 2% decrease [Capped at 90% decrease]

-Sperm Production: 2% decrease]

Nice. So if he was reading this correctly, then by the time it hit 100%, his skin would be twice as soft, his body hair wouldn't grow at all (not that it did anymore, thanks to his curses), his Hips would be 10cm wider, he would be 5'2 rather than 5'6, his cock would shrink to being just 2.25 inches long and 2.25 inches in circumference or girth when hard, and his balls would become tiny and stop producing cum altogether. Also, if Raine rolled badly, he could lose a quarter inch from his length if he rolled badly on [Ejaculation Addiction]'s Side Effects. Given enough time, it would happen, and Raine imagined his Mistress would refuse to let him ejaculate in hopes of encouraging shrinkage at some point. The thought of having a useless micropenis was incredibly erotic to Raine. He wondered if there was a permanent version of [Erectile Dysfunction] he could get.

[Subject deemed inactive. Beginning Application of Side Effects.]

Here it came, Raine was honestly kind of excited, his previous fear of the side effects laid to rest after seeing the roll table, he hoped he scored low.

[[Sexual Frustration] increased in level. Level 11 ===> Level 12].
[Rolling Random Side Effects]
[Rolling]
[Rolled: 13]
[Gained: 4 Levels of Sexual Frustration]
[Gained: 2 Levels of Body Sensitivity]
[Gained: 2 Levels of Aphrodisiac Affected (Permanent)]

A wave of arousal crashed over Raine. He felt the pressure in his cage increase immensely, he realised this was the first time he was in the cage without being otherwise incapable of getting hard. Now all that stopped him was the hard metal encasing his cock. The pressure was causing the pain in his cock to flare up again, turning to it into pleasure. He let out a small moan as he began to sit up. He quickly noticed the absence of his mistress, clearly she'd already left for the summoning. He ought to ask her how it went when she got back - maybe after she fucked him though, to help her vent her frustrations if it didn't go so well. He wondered when she'd be back.

Raine decided to get out of bed. His latex-clad feet gripped against the wooden floor as he padded towards the door. On it was a note, held on by some magical adhesive or something - clearly his mistress's doing. He took the note off the metal door, and read aloud.

"Had to leave without saying goodbye. Do some anal training by yourself for a while, I've left a flask of lube at the end of the bed and I'm sure you can figure out how to finger yourself - make sure to put your plug back in when you're done. I've asked Myalenphor to check in on you around noon-ish. She won't mind if you're still training, go to her if you need help with anything." He read out.

The note crumbled into dust and disappeared. With nothing else to do, Raine decided to follow his Mistress' orders. He walked over to the flask, picking it up in his hands. He gave it a quick shake, hearing lube slosh about in it. He got back on the bed, lying on his back, knees up, and pulled out his buttplug, moaning slightly as it slipped out. He then opened the flask, pouring some lube out onto his right hand. To his shock unlike the other lube his mistress had used two days ago, which had been clear, this new lube was a translucent white, mimicking cum. Honestly, the thought of his asshole looking like it'd just been creampied was hot, so Raine welcomed the change. He rubbed his hands together, smearing the lube all over them, then rubbed his ass, lubricating his rear entrance. Gingerly, he took his middle finger and teased it into the entrance. The pleasure was immediate and he quickly shoved his whole finger in. Deciding that wasn't enough, he also tried to slip his ring finger in. It was met with more resistance, his asshole not quite willing to accommodate it immediately. Sure enough though, after maybe 20 seconds of wiggling and desperate moans, he felt his ring finger enter properly, taking its place beside his middle finger. He plunged them in and out, fingering his ass properly, increasing in speed as he felt the pressure on his cock increase. He let out a few girly wails of lust as he did so. The lube made wet sticking sounds as his palm impacted against his ass. His [Body Sensitivity], [Sexual Frustration] and [Anal Sensitivity] worked in tandem to make the pleasure utterly amazing. Yet he found himself struggling to cum still. He wasn't able to touch his cock at all really, and the thing sat there uselessly spewing precum that ran down, coating his scrotum, his inner thighs and Mistress's bed. Minutes passed, and he wished his mistress was here to make him cum, or at least to cum in him. Hell, he'd take being came on at this point. Imagining the lube being his Mistress's cum helped motivate him to continue, as he moved towards half an hour of manic anal fingering. Raine felt like he was going mad, where the hell was his orgasm? He decided to slip another finger into his ass, this time his index finger. His asshole protested immensely to the treatment, but Raine didn't care, any pain felt would be partially refunded as pleasure, and if a third finger was necessary for him to cum, then he'd stick a third finger in his ass happily.

Another 5 minutes revealed that the third finger was just barely helping. He could feel himself getting a bit closer to cumming, though it still felt minutes away. Raine pressed on, solely focused on cumming now. He needed to cum, so desperately. He moaned loudly, without regard as to who might hear. By this point, his asshole was starting to get sore, but that only made it feel better. Raine was starting to drive himself crazy from the consistent pleasure. He watched as his caged manhood jiggled slightly in sync with his fingers violating his asshole, the way that it bounced around while he pleasured himself like he was a girl was pleasantly degrading. Another 5 minutes passed, and he finally felt himself reach the verge of orgasm, he felt relief wash over him, picking up the speed again. 

Suddenly, the dam burst, and Raine felt himself cumming, cumming harder than he ever had. Some rather thin-looking semen spurted out of his cock, landing on his thighs as he let out a surprisingly girly series of moans. Shivers racked his body as the orgasm continued. The pleasure was so intense he felt as though he might pass out.

[You have came from anal: +0.1% [Feminisation] Progress]
[You have came in chastity: +0.1% [Feminisation] Progress]
[You have came hands-free: +0.1% [Feminisation] Progress]
[[Anal Sensitivity] increased in level: Level 2 ===> Level 3]
[[Sexual Frustration] decreased in level: Level 16 ===> Level 15]

Raine sighed, lying there in post-orgasmic bliss. He felt amazing. At some point, he'd removed his hand from his ass he realised. He sunk his middle and ring fingers back into his ass, slowly and rhythmically fingering his ass. He laid there for who knows how long, slowly fingering himself again. He felt pride in having his first anal orgasm, and having increased his feminisation by 0.3% in one go. He hoped his mistress would praise him for it, perhaps even reward him for it. If she did, Raine hoped it was with more anal orgasms, or at least a bigger plug. It was then he saw his notifications.

[24 hours past since last receiving or performing oral sex! Side effects will be applied shortly]

[24 hours past since last coming into contact with other sapients' semen! Side effects will be applied shortly]

Oh, this was going to be good.

[[Sexual Frustration] increased in level. Level 15 ===> Level 16]
[Rolling Random Side Effects (1d20)]

Raine read the description for these random side effects.

[Random Side Effects (Oral Addiction): A 20-sided die will be rolled to determine additional side effects. Side effects are as follows:

20 - No additional Side Effects
19 - 1 Level of [Sexual Frustration]
18 - 2 Levels of [Sexual Frustration]
17 - 3 Levels of [Sexual Frustration]
16 - 4 Levels of [Sexual Frustration]
15 - 5 Levels of [Sexual Frustration]
14 - 2 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent)
13 - 4 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent), 2 Levels of [Aphrodisiac Affected](Permanent)
12 - 5 Levels of [Sexual Frustration], 3 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
11 - 10 Levels of [Sexual Frustration], 1 Level of [Oral Addiction]
10 - 10 Levels of [Sexual Frustration], 2 Levels of [Oral Addiction], 1 Level of [Body Sensitivity](Permanent)
9 - 10 Levels of [Sexual Frustration], 3 Levels of [Oral Addiction], 1 Level of [Body Sensitivity](Permanent), 1 Level of [Aphrodisiac Affected](Permanent)
8 - 10 Levels of [Sexual Frustration], 5 Levels of [Oral Addiction], 3 Levels of [Body Sensitivity](Permanent), 1 Level of [Aphrodisiac Affected](Permanent)
7 - 10 Levels of [Sexual Frustration], 10 Levels of [Oral Addiction], 5 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
6 - 10 Levels of [Sexual Frustration], 10 Levels of [Oral Addiction], 10 Levels of [Body Sensitivity](Permanent), 5 Levels of [Aphrodisiac Affected](Permanent)
5 - 10 Levels of [Sexual Frustration], Gain 1 Level of [Oral Sensitivity]
4 - 10 Levels of [Sexual Frustration], Gain 2 Levels of [Oral Sensitivity]
3* - 10 Levels of [Sexual Frustration], Gain Trait [Long-Tongued], Gain 3 Levels of [Oral Sensitivity]
2* - 10 Levels of [Sexual Frustration], Gain Trait [Cock Hungry], Gain 4 Levels of [Oral Sensitivity]
1** - 10 Levels of [Sexual Frustration], Lose your gag reflex, Gain 5 Levels of [Oral Sensitivity]

*Traits only applied once, subsequent rolls will only add levels of [Sexual Frustration] and [Oral Sensitivity].
**Gag reflex only lost once, subsequent rolls will only add levels of [Sexual Frustration] and [Oral Sensitivity].]

[Rolling]
[Rolled: 17]
[[Sexual Frustration] increased in level. Level 16 ===> Level 19]

Then came the next roll

[[Sexual Frustration] increased in level. Level 19 ===> Level 20]
[Rolling Random Side Effects (1d20)]

[Random Side Effects (Semen Addiction): A 20-sided die will be rolled to determine additional side effects. Side effects are as follows:

20 - No additional Side Effects
19 - 1 Level of [Sexual Frustration]
18 - 2 Levels of [Sexual Frustration]
17 - 3 Levels of [Sexual Frustration]
16 - 4 Levels of [Sexual Frustration]
15 - 5 Levels of [Sexual Frustration]
14 - 2 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent)
13 - 4 Levels of [Sexual Frustration], 2 Levels of [Body Sensitivity](Permanent), 2 Levels of [Aphrodisiac Affected](Permanent)
12 - 5 Levels of [Sexual Frustration], 3 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
11 - 10 Levels of [Sexual Frustration], 1 Level of [Semen Addiction]
10 - 10 Levels of [Sexual Frustration], 2 Levels of [Semen Addiction], 1 Level of [Body Sensitivity](Permanent)
9 - 10 Levels of [Sexual Frustration], 3 Levels of [Semen Addiction], 1 Level of [Body Sensitivity](Permanent), 1 Level of [Aphrodisiac Affected](Permanent)
8 - 10 Levels of [Sexual Frustration], 5 Levels of [Semen Addiction], 3 Levels of [Body Sensitivity](Permanent), 1 Level of [Aphrodisiac Affected](Permanent)
7 - 10 Levels of [Sexual Frustration], 10 Levels of [Semen Addiction], 5 Levels of [Body Sensitivity](Permanent), 3 Levels of [Aphrodisiac Affected](Permanent)
6 - 10 Levels of [Sexual Frustration], 10 Levels of [Semen Addiction], 10 Levels of [Body Sensitivity](Permanent), 5 Levels of [Aphrodisiac Affected](Permanent)
5 - 10 Levels of [Sexual Frustration], Gain 1 Level of [Cum Crazy]
4 - 10 Levels of [Sexual Frustration], Gain 2 Levels of [Cum Crazy]
3* - 10 Levels of [Sexual Frustration], Gain Trait [Cum Connoisseur], Gain 3 Levels of [Cum Crazy]
2* - 10 Levels of [Sexual Frustration], Gain Trait [Cum Diet], Gain 4 Levels of [Cum Crazy]
1** - 10 Levels of [Sexual Frustration], Your cock will constantly leak precum, Gain 5 Levels of [Cum Crazy]

*Traits only applied once, subsequent rolls will only add levels of [Sexual Frustration] and [Cum Crazy].
**Precum leakage only applied once, subsequent rolls will only add levels of [Sexual Frustration] and [Cum Crazy].]

[Rolling]
[Rolled: 3]
[[Sexual Frustration] increased in level. Level 20 ===> Level 30]
[Gained Permanent Effect: Cum Crazy]
[Gained Trait: Cum Connoisseur]

Raine quickly looked at the descriptions as he felt heat flush through his body.

[[Cum Crazy] - Whenever in contact with semen, gain +1% arousal per level. Current Level: 3]

[[Cum Connoisseur] - +1 XP from swallowing Demon Semen, you now feel a need to drink any semen you find.]

Raine barely acknowledged the new traits, having become occupied with methodically fucking his ass with his own fingers, a steady shlick, shlick, shlick sounded out as his hand impacted his ass and the lube spread further. He wasn't sure how long he lay there, slowly fingering his ass. But he was removed from his stupor by the sound of the door opening. In came Myalenphor carrying what appeared to be his and his mistress's clothes from yesterday, the white-haired demoness shrivelling her nose in disgust as she saw Raine lying on the bed covered in a mixture of lube, precum and semen, slowly pressing his fingers into his ass.

"How basal" She said, disapprovingly, her accent thick with disgust.

Raine stopped pleasuring himself and turned to face her.

"I suppose at the very least that the man-pet has its cock locked up. Hurray for small mercies." she spoke to herself tonelessly.

She then addressed Raine directly, "Listen up, Man-thing I have had a stressful day and you will be helping to relieve my stress. You will eat me out until I cum. You will not move or speak until I have done so. You will not be allowed to touch me whilst you do this nor will you be allowed to pleasure yourself. You will bring me to orgasm and then I will leave." the doll-like demoness said dully.

Raine felt the command tug at his being, whilst not as strong as his mistress's commands, he still felt the compulsion to do exactly as she said. He lay there as the quiet demoness made her way over to him. She climbed on top of the bed, lifting her almost ankle-length maid outfit so that she could straddle Raine's face. All that Raine could see was her demonic vagina and all he could do was lick. Raine's tongue flicked back and forth over her cunt, eliciting a slight shake from Myalenphor as he ran his tongue over her clit. For her part, the demoness was practically silent aside from the occasional sharp inhale and practically stock still on top of Raine's face. This continued for another couple minutes, the silence only being interrupted by the odd shaky breath and the ruffle of the Maid outfit on the bed. Raine felt his cock drool slightly as the demoness continued to ride his face, her detached cruelty turning him on. Soon, the occasional twitch of the pale demoness became more common and her slight intonations shifted into quiet moans. She came, grinding on Raine's face as she did so.

[You brought a [Succubus] to orgasm. +5XP]

It seemed like demons that weren't his Mistress rewarded him with less XP. Myalenphor stood up, getting off the bed and then walked off, closing the door behind her, not even deigning to look at Raine after she'd came. A small part of Raine's mind thought that was rude, whilst other parts thought that was hot and that that was what he deserved as a living fucktoy. He shrugged to himself, not really caring that he was just used as a sex toy. It was then that the door opened again, revealing a tall red-headed demoness. Komianchi was scowling slightly as she entered the room, spotting Raine lying there utterly soaked in all sorts of fluids.

"Alright, slut, I have had a terrible summoning, and I need to blow off some steam. I don't suppose you'd mind helping me out? Actually I don't really care whether you mind or not, you're sucking me off. Now." She said, strutting over to the bed.

"Yes Miss" Raine said, getting off the bed and onto his knees before the tall Demoness, her cock pitching a tent under her maid outfit.

"Good to see that you know your place slut. The man that summoned me earlier certainly didn't. You know he demanded just boring ordinary sex? He only lasted a minute as well, after which I was free to leave, but the dumbass summoned me in the middle of a city, so I took one step outside and got swarmed by guardsmen, who killed me after like 5 minutes of fighting. Absolute Bullshit!" The demoness said raising her voice to the point of shouting by the end of her rant.

"I'm sorry to hear that Miss." Raine said earnestly.

"Then get sucking slut." Komianchi ordered, pulling back her dress to reveal a 7 inch long and 1.5 inch wide cock, almost as big as his Mistress's own massive shaft.

Raine dived greedily onto the cock, enveloping it in his mouth. His lips locked around the shaft and his tongue danced along the Demoness' head. His hands worked the huge cock at its base. Komianchi groaned appreciatively as Raine serviced her member. Soon her hips gyrated slightly as Raine continued to blow her, her cock hitting the back of his mouth, causing him to gag and splutter. She grinned at the sight of Raine sucking her cock, looking up at her fearfully.

"Yeah bitch, suck my superior cock." She insulted him

Raine slurped on her shaft harder, his cock dribbling out precum onto the floor.

"Fuck yeah, take my dick you failed male."

Raine moaned around her penis at the degradation. He was pretty sure he'd started making a puddle on the floor with how much his caged cocklet had been dribbling precum. But he wouldn't check, as that meant taking his eyes off Komianchi's shaft, a much more important matter than whatever his pathetic little thing was doing. Komianchi grabbed his hair in one hand, assisting him in diving down her length. She began thrusting properly, the huge cock hitting the back of his mouth and slipping into his throat before pulling back so only the head remained inside his mouth. Now his hands had fallen to the wayside, and he let her brutally fuck his throat without complaint. Saliva ran down the shaft, dripping onto the floor with each vigorous thrust. Her gargantuan balls slapped against his chin as she went.

"How'd you like that huh? I bet you like that you sissy!" She shouted at him.

Raine nodded ever so slightly, eliciting an evil cackle from the Demoness.

"I see why Mistress Tazamoth brought you back here. She and I have always been of the same mind when it came to how to treat males. Honestly, I'm jealous. I'm going to have to hunt down a proper cock-sucking bitch of my own when I become a Greater Demon." She said, fucking Raine's throat silly.

"Anyway, lets see how you take my semen little bitch." She said after a moment.

Raine felt the demoness's cock pull out of his mouth, leaving him to gasp for air as saliva dripped down his chin and onto his thighs and the floor. Komianchi stood over him, violently stroking her shaft. Raine regained his composure and opened his mouth, sticking out his tongue and trying to seem like the best receptacle for the Demoness's jizz. She jerked violently, and Raine was subjected to thick ropes of cum, which landed on his face, in his mouth and down his front. The amount of cum was insane, impossible for any middleplaner of Komianchi's size. He presumed his Mistress produced even more, but she seemed to like ensuring it all entered him, rather than the sudden coating Komianchi had given him. Raine reached up, guiding the cum on his face into his mouth and swallowing.

[You brought a [Succubus] to orgasm. +5XP]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]

Cum dripped from Komianchi's cock and onto the floor, Raine felt the sudden need to clean her shaft. He leant forward, grabbing Komianchi's deflating cock, and sucking it clean. Then he looked down at the floor, the wooden floorboards were splattered with semen. A strange compulsion lead Raine to get down on all floors and begin licking the floor clean, lapping up the cum feverishly.

"Oh wow. You're a total cumslut." Komianchi said, surprised.

Raine hummed in the affirmative as he knelt at her feet licking up drops of cum from the floor, and scooping up stray cum from across his body with his hands, which he promptly sucked clean.

"You know what, I've had an idea. Wait here for 20 minutes Raine. I happened to see a few newly-minted succubi pass the house a couple minutes ago, and I feel like I could be onto something that'll really help your training." She explained.

With that, she rushed off, leaving Raine to sit there with nothing to do. Instead of playing with his ass, this time his hands reached down to play with his caged cock. His mind went back to when he was fingering himself earlier that day, his arm had bumped into his cage, which had elicited a shock of pleasure as his sore tip felt even more pain. Maybe, he could mess with his cage enough to bring himself to cum? With his massively increased arousal, Raine did feel kind of close from having his throat fucked and being degraded. Fuck it, he decided, might as well try. His left hand fondled his balls, while his right hand grabbed his imprisoned cock and started wiggling the device. Pleasure started to seep into Raine through his genitals, but it wasn't enough for him - he wanted more. Instead of fondling his balls, he decided to start lightly slapping them. Soon, they became sore and pleasure radiated through them with each slap - this he could work with. He kept it up, slowly increasing the pain in his balls as he continued smacking the pointless things. A feeling of nausea started creeping up into him, but he carried on, he felt so close. The speed of the little slaps increased, and the nausea from the pain became stronger still. He drew his hand back and slapped his balls hard this time, and he was sent over the edge. Small thin spurts of watery cum shot out of his cage as Raine sighed in relief.

[You have came in chastity. +0.1% [Feminisation] Progress]
[[Sexual Frustration] decreased in level. Level 30 ===> Level 29]
[[Pain into Pleasure] increased in level. Level 6 ===> Level 7]

Raine was pleased to have increased his [Feminisation] again, it'd gone up 0.6% today now, he wondered if he could get it even higher before his Mistress came back. Judging by the light level outside, he still had a few hours to do so - perhaps he should aim for 1% progress today? He imagined managing that daily, quickly morphing into a proper sissy, the thought was exciting - Raine couldn't wait. Honestly he wished he could do it faster, even if he did appreciate how fun it was to slowly sink further into lust and depravity. He wondered how utterly fucked he'd be soon, already he struggled to think about things that weren't lewd in nature and his covenant hadn't even lasted a week yet - hell his crest hadn't been finished.

The door opened and Komianchi walked back in, in one hand she held a bunch of used condoms of various sizes each absolutely brimming with cum.

"Hey Raine, me and the twins tracked down those new succubi we saw earlier, made a deal that if we got to collect their sperm we'd give them each a penny." She explained, lifting the bunch of heavy condoms.

"You, are going to entertain me and train at the same time by drinking each of these things." She commanded.

"Yes Miss" Raine said, drooling somewhat at the sight of what must've been a dozen semen-filled condoms.

"The small ones are from the new Succubi, the two medium ones are from the twins, and the big one is another of my loads. We'll be saving that one for last." She explained, handing Raine a 'small' condom, which looked like it'd be a bit large on Raine's 4 and a half inch cock, and had been filled with enough cum to compare to 4 of Raine's own ejaculations, before [Mandrake Drunk] and [Feminisation] had decreased his load size.

Raine took the condom, placing the opening in his mouth, and raised it above his head whilst suckling on it. Semen poured out of it and into his mouth, he gulped it down greedily. Once most of it had come out, he strained it, running his fingers from the tip to the opening so as to get one last mouthful of the intoxicating stuff.

[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]

Yeah, it looked like he was going to be making it past 1% progress today. Komianchi laughed at him as she handed him another condom to drain.

"Oh, this is great stuff! Man, I should try this on the next guy that summons me." She laughed.

[You swallowed Demon Semen. +3 XP, +0.1% [Feminisation] Progress]

[Semen Addiction] kicked in, granting him another +1 XP. Raine giggled around a mouth of cum as Komianchi handed him another condom, stroking her own cock as she did so. 

[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]

"Fucking hell slut, you love cum huh?" Komianchi asked as he drained another condom

"Yes Miss. Please give me more cum Miss." Raine begged, receiving a 6th condom full of Demonic spunk.

[You swallowed Demon Semen. +3 XP, +0.1% [Feminisation] Progress]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]

Raine coughed, feeling incredibly full, his throat felt tacky and slimy as gulped down the cum in the last small condom.

"Good slut, now bitch, let's move onto the medium two. Ilenthal and Ilaphie worked very hard to make these for you, so you'd better not spill a drop half-breed."

Raine looked at the swollen condoms, mouth salivating, his cock also drooling. He took the first one from the Demoness, and began to drink from it. The thick seed slid down his throat as he gulped down the load, taking care to ensure not even a drop was spilled. Drinking it felt like it took ages, yet Raine wanted it to last even longer, he wanted to be stuck permanently drinking cum.

[You swallowed Demon Semen. +3 XP, +0.1% [Feminisation] Progress]
[[Semen Addiction] increased in level. Level 1 ===> Level 2]

Raine felt even thirstier for cum as [Semen Addiction] levelled up, combining with the effects of [Cum Connoisseur] to drive him half-mad from the thirst. Komianchi didn't even bother handing him the next one, just putting the end up to his mouth, letting him suck on it as she tilted the condom up, flooding his mouth with the sweet, addictive nectar. Raine felt his ass clench around his buttplug, and the pressure of his cage increased, he felt like he would come soon. 

[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[[Semen Addiction] increased in level. Level 2 ===> Level 3]

"Hell yeah slut, drink all that cum. One last one to go before you can have some from the tap, this one's mine" Komianchi said, offering him a ludicrously stretched condom full of semen.

Raine put the end in his mouth, the salty taste assaulting his taste buds once more. Komianchi tipped the condom straight up, pouring a wave of cum into Raine's mouth. Raine swallowed as quickly as he could, yet he was still overwhelmed and cum dribbled out of his mouth, dripping down his front, soaking him. Still more cum flowed into his mouth and Raine began to worry about drowning in the stuff. Finally, the endless tide relented and Raine moaned slightly, feeling utterly bloated. Komianchi did not look impressed

[You swallowed Demon Semen. +2 XP, +0.1% [Feminisation] Progress]
[[Semen Addiction] increased in level. Level 3 ===> Level 4]

"You stupid fucking bitch! How dare you spill my glorious seed that I so generously gave you." She shouted at him.

Raine flinched back "S-sorry Miss, it wasn't on purpose I swear!"

She slapped him, pain and a touch of pleasure exploded from his cheek.

"You think I care slut? You spilled it, so now you've got to make it up to me. Get sucking before I stomp on your worthless, little Manhood!" She said.

"Y-yes Miss." Raine stuttered, grasping the cock in front of him.

"Actually you know what, I don't care if you suck it properly, I'm just going to fuck the shit out of your throat." Komianchi growled impatiently, grabbing Raine with the hand that wasn't keeping up the front of her dress and forcing him down on her cock.

The Demoness began to brutally fuck him in the mouth without a care for his comfort or ability to breathe. It honestly started to hurt, which only made it hotter and got the cum-drunk Raine closely to climax. Komianchi grew frustrated with the maid dress's constant need to be held up and with a growl briefly stopped throatfucking Raine to take the thing off. Stripped down to just her crotchless tights and her bra, Komianchi grabbed Raine's head in both her hands and restarted the violent oral sex, her large balls slapping against the Half-elf's chin and throat as she rammed her cock in and out of his mouth. Raine let out a muffled groan, and felt himself climax, cum spurting weakly out of the cage and onto the floor in front of the tall maid.

[A [Succubus] has brought you to orgasm! Body Sensitivity increased in level. Level 24 ===> Level 25]
[You came in chastity. +0.1% [Feminisation] Progress]
[You came hands-free. +0.1% [Feminisation] Progress]

"Oh, you like that pathetic little bitch? You came from a rough throatfucking? What a slutty little half-breed!" Komianchi roared. "Take my seed sissy!"

Raine felt the maid cum, her hands pulled him to the bottom of her shaft with a great amount of force, holding him there as she came. Huge ropes of cum made their way down into his stomach as Raine felt his mind go foggy from the pleasure and the lack of oxygen.

[You brought a [Succubus] to orgasm! +5 XP]
[You swallowed Demon Semen! +3 XP, +0.1% [Feminisation Progress]]

"Fuck yeah. That was great." Komianchi said. "You're not so bad you sissy slut. We'll have to do this again some time."

The admission made the frankly exhausted Raine smile. It was good that his value as a fucktoy was being recognised. Komianchi walked off, leaving Raine alone in his Mistress's bedroom. He looked down at himself, half-soaked in cum, saliva and sweat. His thirst seemed to have finally abated, having been pumped full of semen for the past however long. Yawning, he decided to go to the baths and then sleep, as it seemed his Mistress was running a bit late.

He padded out into the corridor, leaving a slimy trail as he went - Myalenphor probably wouldn't be too happy, but she didn't really seem like one for happiness anyway. He walked into the Baths, making a beeline for the warm pool. Once in, the fluids seemed to melt off of him, leaving him feeling much cleaner. He stood in the water for a while, just taking in the blissful feeling of warmth on his skin. He could feel himself nodding off however, and so he decided to get out of the baths before he drowned. He dried himself off on a towel, and walked back to his Mistress' bedroom. He got into his Mistress's bed, the thing feeling utterly massive without his Mistress's reassuring presence. Checking his cage and his plug one last time, he soon fell asleep, dreaming of his Mistress.

-----------

Changes this Chapter:

[Special Trait Progress Increased: Feminisation: 1.9% ===> 4.0%]

[Trait Gained: Cum Connoisseur]

[Permanent Effect Gained: Cum Crazy: Level 3]

[Permanent Effect Increased: Body Sensitivity: Level 22 ===> Level 25]

[Permanent Effect Increased: Pain into Pleasure: Level 6 ===> Level 7]

[Permanent Effect Increased: Aphrodisiac Affected: Level 5 ===> Level 7]

[Permanent Effect Increased: Anal Sensitivity: Level 1 ===> Level 3]

[Permanent Effect Increased: Semen Addiction: Level 1 ===> Level 4]

[Effect Gained: Mandrake Hangover: Level 4]

[Effect Increased: Sexual Frustration: Level 11 ===> Level 29]

[Effect Decreased: Entranced: Level 9 ===> Level 8]

[Effect Decreased: Heightened Submission: Level 9 ===> Level 8]

[Effect Lost: Mandrake Drunk: Level 4]

Chapter Text

6 Days since Covenant Formed:

-----------

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 4]
[HP Increased: 14/25 HP ===> 18/25 HP]
[Rolling]
[Roll Failed: Already at full MP]

[Special Trait Progress Increased: Feminisation: 4.0% ===> 4.1%]

[Permanent Effect Increased: Body Sensitivity: Level 25 ===> Level 27]

[Permanent Effect Increased: Anal Sensitivity: Level 3 ===> Level 4]

[Effect Decreased: Mandrake Hangover: Level 4 ===> Level 3]

[Effect Decreased: Entranced: Level 8 ===> Level 7]

[Effect Decreased: Heightened Submission: Level 8 ===> Level 7]

Raine awoke feeling less sore than he did the day before. He felt a warmth pressed up behind him, he rolled over to see his Mistress, the giant demoness still asleep. She must've gotten back after he'd fallen asleep. He was careful not to wake her, simply staring at her beautiful figure, it seemed as though she'd taken her barbells out before falling asleep, perhaps she was going to show him whatever new ones she'd gotten. He decided to check up on his [Feminisation] progress whilst she still slept.

[Feminisation Progress: 4.1%

Effects of Progress:

-Skin softness: 104.1%

-Body Hair Growth Rate: 95.9%

-Width of Hips: 4.1mm increase

-Height: 4.1mm decrease

-Penis Length: 2.05% decrease (2.34mm Decrease Hard)

-Penis Girth: 1.025% decrease (0.91mm Decrease Hard)

-Testicle Size: 4.1% decrease [Capped at 90% decrease]

-Sperm Production: 4.1% decrease]

Not bad at all. The shrinkage of his penis would probably be noticeable if it weren't for his cage. He hoped that his feminisation increased in speed, he could hardly wait. His cocklet twitched in its cage as he thought about it. He also wondered what'd happen when [Feminisation] inevitably hit 100% - obviously he'd be sterile twice over at that point, and he'd be much more effeminate but the description said that once it hit 100%, the trait would undergo an evolution. Raine hoped that whatever the evolution was, it made him even smaller and weaker than he'd be once fully feminised. 

His Mistress stirred slightly, opening her eyes and waking up.

"Good morning Little Raine, I was a little late home last night, my summoning ended up taking a little longer than first expected, but it was more successful than I had hoped." She said.

"Good morning Mistress." Raine said, smiling.

"Komianchi told me she made good progress on you yesterday. I read your stats and I must say I do agree. I think you're in for a little reward, Raine."

"Thank you Mistress! If I might ask, what's the reward?" Raine asked cheerily.

"We're going to be upsizing your plug, Raine. Then I think we'll enjoy a day of training. How does that sound my Little Raine?" Mistress Tazamoth asked.

"That sounds amazing, thank you Mistress." Raine responded.

"Well, let's not hesitate then my little slut." His Mistress said, getting out of bed and circling round to Raine's side.

Raine got out of bed and bent over, resting against the bed, ready for his mistress to swap out the butt plug. He looked over his shoulder, his Mistress had summoned a substantially larger plug than he one in him, and was currently working to coat it in lube. Where his current butt plug was about 1 inch in length and 0.75 inches in width, the new one seemed to be 2 inches in length and an inch wide. Raine found himself wondering if the enchants were stronger. Of course, his wondering was soon cut short by his Mistress yanking the plug out of his ass. Raine squealed like a girl at the sudden sensation. Then, his Mistress started to push the new butt plug in, moving slowly. Raine felt his asshole stretch to accommodate the increased girth of the new plug and then tighten as it fully accepted the toy, only the flared base sticking out. Raine let out another moan at that.

[[Cursed Blacksteel Butt Plug] Equipped!]
[[Cursed Blacksteel Butt Plug] Primary Curse Activated: Increasing Sensitivity Curse!]
[[Cursed Blacksteel Butt Plug] Secondary Curse Activated: Very Weak Arousal Curse!]
[[Cursed Blacksteel Butt Plug] Tertiary Curse Activated: Feminising Curse!]
[[Feminisation Curse] Secret Condition met: Increase the size of your butt plug: +0.1% [Feminisation] Progress. Current Progress: 4.2%]

A quick check of the descriptions confirmed that the first two curses were identical to those on his previous plug. The third one was new though, he gave its description a more in depth read through than the cursory glances he gave the other two curses.

[Feminising Curse: If the plug is equipped for the entire duration of a Long Rest, gain +0.1% [Feminisation] Progress.]

'What a great curse.' Raine thought. This would in fact make his feminisation just that bit quicker.

"Thank you Mistress." Raine said.

"Now, let's get to training you some more, my Raine." His Mistress said seductively.

"Wh-what training are we doing today M-Mistress?" Raine asked.

"Let's start with some more pain training okay?" She proposed.

"Okay Mistress." Raine said.

"Oh, but first, you should give your Mistress a kiss." She ordered.

Raine stood up and walked over to his Mistress, looking up at her. She bent over slightly, and Raine accepted her embrace, opening his mouth wide for her tongue to slide in, before transitioning into a more normal seeming kiss.

[Your Mistress, Tazamoth, has used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level. Level 27 ===> Level 28]

His Mistress' eyes flashed green as she withdrew.

[Your Mistress, Tazamoth, has cast [Black Passion] on you!]
[[Aphrodisiac Affected](permanent) increased in level. Level 5 ===> Level 6]

Raine let out a shaky breath after the passionate kiss. His Mistress seemed to remember something.

"Oh I almost forgot Raine, I should show you my new barbells." She said.

She summoned a small box from nowhere, opening it up and turning around. A few seconds of fiddling later and Mistress Tazamoth had put on the new barbells. She turned around and Raine stared at his Mistress's large tits. The new barbells were very similar to her old ones, being made of blacksteel like them, but being slightly longer.

[Your mind is affected by a nearby enchanted item!] 

Raine dismissed the notification, he knew what it meant and didn't care. If Mistress wanted to play with his mind, then she could - besides the effect wasn't actually that strong, he just happened to be in complete agreement with its goal of making him obsessed with his Mistress, making it feel a lot stronger than it actually was. Soon, he was busy looking at his Mistress's amazing tits. He could feel himself drooling slightly.

[[Entranced] increased in level. Level 7 ===> Level 9]

[[Heightened Submission] increased in level. Level 7 ===> Level 8]

Raine felt his cocklet stir slightly while he stared at his Mistress' tits. One hand moved down there, touching the cage futilely. His Mistress smiled at him as he stared at her perfect breasts.

'Gods,' Raine thought, 'My Mistress's tits are perfect.'

"Raine? How do you like my new barbells?" His Mistress asked.

"...so pretty. They look perfect Mistress." Raine said, feeling dazed, he could hardly take his mind off her chest.

"Is that so? How about we sit back down on the bed so you can get a closer look?" She asked.

"Please Mistress." Raine begged, not taking his eyes off her boobs.

The pair sat down on the side of the bed. Raine stared almost unblinkingly at her tits.

"Would you like to touch them Raine?" His Mistress asked him.

"More than anything Mistress. Please I'd do anything." Raine confessed

"How about you look at them just a little longer, Raine? Can you be a good boy for me and wait just a little longer for me?" His mistress asked.

"Yes Mistress. I-I can do that... I'll do that Mistress." Raine said, tripping over his words as he leant in closer to her breasts.

[[Entranced] increased in level. Level 9 ===> Level 11]

[[Heightened Submission] increased in level. Level 8 ===> Level 9].

"Good boy Raine." She praised him

"Thank you Mistress." Raine said absently

"You can fondle my tits now Raine, since you're such a good boy." She permitted.

"Thank you Mistress." Raine said distractedly as he lifted a hand to touch his Mistress's perfect giantess tits.

"Mmm... Good Boy Raine." She said as the femboy began to knead her breasts.

"The barbells are hypnotic, right Mistress?" Raine asked.

"I had a feeling you'd notice the effect but not even try to resist Raine. You're a good little slut like that. But to answer your question, they're not actually quite truly hypnotic, merely Entrancing. Would you like to try Hypnosis some time, Raine?" His Mistress said.

"Yes Mistress, I'd really like that. To have my mind conquered by you would be amazing." Raine confessed.

"Mmm. We'll have to give it a try then Raine, but do know that I appreciate your lack of will even without any Hypnotism."

"Thank you Mistress, I live to serve you now." Raine said, drooling slightly.

[[Entranced] increased in level. Level 11 ===> Level 12]

[[Heightened Submission] increased in level. Level 9 ===> Level 10]

The two moved back into the bed properly, previous discussion about training forgotten, Raine staring at his Mistress's breasts the entire time. Once lying back down, Mistress Tazamoth embraced Raine, drawing him in against her huge body, his face being pressed against her tits. The Half-Elf used his new position to lick his Mistress's breasts, before transitioning to sucking at one of her nipples. Raine felt himself get more and more aroused as the effects of [Entranced] increased in level.

[[Entranced] increased in level. Level 12 ===> Level 13]

His suckling increased in speed and desperation, whilst his Mistress ran her fingers through his hair and whispered praise in his ear.

"You're a good boy Raine, keep sucking Mistress's tits."

"My Raine's such a good little slut, sucking my tits like that without even needing me to ask."

"Gods it's so hot to see you so focused on me."

"Mmm... Good boy..."

Raine felt his cage getting slick with precum as the words of encouragement came from his Mistress. He continued to suck at her breasts, treating them like they were the only things in the entire world. He felt his Mistress's own cock start to rise, pressing hard against him caged genitalia, dwarfing his worthless cock.

[[Entranced] increased in level. Level 13 ===> Level 14]

He carried on sucking.

[[Entranced] increased in level. Level 14 ===> Level 15]

-----------

Tazamoth's POV

Tazamoth looked down at her little covenanter as he sucked on her tits with such desperation, as though he expected her to start lactating and nourish him. The prospect was unlikely given that Demonesses had tits to arouse and draw in Middleplaners rather than feed demon young - which generally spawned in from the manifestation of middleplanar emotions rather than being born conventionally. In fact, only certain powerful demons had the ability to actually reproduce conventionally, and Tazamoth was not nearly powerful enough to be counted amongst them. She'd had to explain all that to the nun that'd summoned her yesterday, she'd been deathly afraid of pregnancy which had hindered her corruption until she'd given her a half-hour long lecture on Demon biology. Of course, that delay had lead her to being discovered by another nun. She'd only barely convinced that second nun to become corrupted as well - but with 2 nuns in that nunnery serving Ioketara, it'd soon fall within their hands.

She looked back down at Raine, even if her breasts were non-functional in some ways, Raine deserved some kind of reward for his devotion, preferably one that'd make him even more devoted to her. Tazamoth had been saving up skill points, having earned a 5th one when she'd levelled up yesterday for converting those two nuns. Originally she'd been planning to save up to upgrade her Aphrodisiac Fluids, with the upgrade costing 10 skill points - but that had been before Raine had become her covenanter. With her new Half-Elf, she should really consider what other possible traits or skills she could buy with those 5 skill points. She opened up the skill point shop in her menu.

[Unspent Skill Points: 5]
[Available Skills]

[Very Weak Necrotoxic Bite - 1 SP]
[Very Weak Neurotoxic Bite - 1 SP]
[Very Weak Myotoxic Bite - 1 SP]
[Very Weak Cytotoxic Bite - 1 SP]
[Very Weak Paralytic Bite - 1 SP]

While developing a venomous bite was alluring, it clashed with her skill [Foolish Bite], so as always she dismissed these.

[Tough Skin - 2 SP]
[Increased Strength - 2 SP]
[Very Weak Fire Affinity - 3 SP]
[Very Weak Blood Affinity - 3 SP]

While physical traits were nice, she was a succubus and her strengths lay in things other than physical fights. She dismissed the two currently available affinities as well, she'd yet to dedicate too much time to magic beyond her own innate abilities, and she didn't think she was ready to decide on any affinities, plus neither of these would help train Raine. She narrowed her viewable skills down to sexual Traits and skills.

[Increased Semen Production - 2 SP]
[Cock Nodules - 2 SP]
[Addictive Cum - 2 SP]
[Increased Penis Length - 2 SP]
[Increased Breast Size - 2 SP]
[Penis Jealousy - 3 SP]
[Keyholder Queen - 3 SP]
[Degrading Strike - 4 SP]
[Very Weakly Entrancing Breasts - 5 SP]
[Hypnotic Gaze - 5 SP]

These were much more like it. Still, there were some that Tazamoth wrote off immediately, [Increased Semen Production] wouldn't help train Raine, she already produced enough as is to satisfy the femboy's thirst. [Cock Nodules] and [Increased Penis Length] would both make training Raine harder - he was already working to be able to accommodate his Mistress's current cock in his ass, extra inches or a large bumps would only make anal sex more difficult. [Increased Breast Size] was nice, especially since they were large already, a feature that Az seemed to appreciate when she took Raine for some piercings but it wasn't actually that useful. [Very Weakly Entrancing Breasts] just seemed to do what her piercings did but worse, so no point in getting that. She discarded all of them, leaving behind a shorter list.

[Addictive Cum - 2 SP]
[Penis Jealousy - 3 SP]
[Keyholder Queen - 3 SP]
[Degrading Strike - 4 SP]
[Hypnotic Gaze - 5 SP]

She decided to read through the descriptions of these five traits or skills. She quickly checked on Raine, who was still sucking obediently on her tits, before bringing up the descriptions.

[Addictive Cum (Trait) - 2 SP - Any middleplanar sapient who consumes your semen gains a level of [Semen Addiction] on each occasion.]

Certainly not terrible, ordinarily it'd take ten consumptions in one day to increase [Semen Addiction] in level. She'd definitely get it if she also selected one of the 3 skill point traits or skills. She moved onto [Penis Jealousy]

[Penis Jealousy (Trait) - 3 SP - Any sapient with a smaller penis than you who sees your penis must make a Hard Wisdom Saving Throw, and upon failure will gain 1 level of [Sexual Frustration]. Resets every 24 hours]

Once again, not terrible by any means, but Raine's sexual addictions already served to increase his [Sexual Frustration] rapidly. Still, could be good against males on the middleplane. She decided to move onto [Keyholder Queen].

[Keyholder Queen (Trait)] - 3 SP - Any Sapient in chastity to which you hold a key immediately gains +10% arousal, and disadvantage on all saving throws made against your faction members. If they have a penis, failing a saving throw against you whilst in chastity will inflict 1 level of [Erectile Dysfunction].

Now this was more like it. This would practically break her Little Raine's Penis, which'd make him much hotter. Oh she'd almost certainly get this one. Plus it'd help with possible future covenanters as well. Still, she should at least check the other two traits or skills.

[[Degrading Strike (Skill)] - 4 SP - When you hit an opponent, your strike will magically imbued to inflict 1 Level of [Heightened Submission] in them, costs 5 MP]

[[Hypnotic Gaze (Trait)] - 5 SP - Your very gaze is hypnotic. Staring into your eyes will apply the effect [Hypnotised] onto any Middleplaner. Additional staring will increase this effect's level at a rate of once per minute]

Neither were bad per se, but both definitely seemed worse than a combination of [Keyholder Queen] and [Addictive Cum]. Not to mention that Raine was already pretty much perfectly obedient and submissive, and she could always take the time to learn Hypnosis spells if she ever really needed to Hypnotise anyone. She locked in [Keyholder Queen] and [Addictive Cum].

[Trait Gained: Keyholder Queen]
[Trait Gained: Addictive Cum]

Marvellous. She heard Raine give a soft gasp, detaching himself from her tit as he felt the increased arousal. Tazamoth really ought to have a look what traits were available for Raine to purchase, since he had a few skill points saved up by now. Still, first she'd like to finally get around to the pain training she promised Raine.

-----------

Raine's POV

[[Entranced] increased in level. Level 15 ===> Level 16]
[[Entranced] increased in level. Level 16 ===> Level 17]
[[Entranced] increased in level. Level 17 ===> Level 18]
[[Entranced] increased in level. Level 18 ===> Level 19]
[[Entranced] increased in level. Level 19 ===> Level 20]
[[Entranced] increased in level. Level 20 ===> Level 21]
[[Entranced] increased in level. Level 21 ===> Level 22]

[Your Mistress, Tazamoth, gained Trait [Keyholder Queen], causing the following effects on you: [Keyheld] - +10% arousal, disadvantage on saving throws against her faction members, all failed saving throws add 1 level of [Erectile Dysfunction]. This has occurred because: You are in a chastity cage]

Raine gasped as he felt the increase in arousal, pressure on his cage increasing. He felt his mistress shift slightly and he stopped focusing so much on her tits to listen to whatever she was about to say, pulling back from them now that he had other priorities beyond just worshipping his Mistress's body. His Mistress sat up and spoke to him.

"It's good to see you enjoying my tits Raine, but we were going to do some pain training. Get out of bed for me." She said

"Yes Mistress, sorry Mistress." Raine apologised.

His Mistress got out of bed as well, looming over him, reaching down and grabbing his chin. She held it aside, exposing his neck. Raine let out a moan as she bit into him, his [Pain into Pleasure] effect turning the sharp pain of Tazamoth's fangs into a sudden burst of pleasure.

[Your Mistress, Tazamoth, used [Foolish Bite] against you!]
[Hit!]
[You took 1d8 Piercing Damage]
[Rolling]
[Rolled: 2]
[You lost 2 HP!]
[HP Decreased: 18/25 HP ===> 16/25 HP]

[Beginning Hard Wisdom Save with Quadruple Disadvantage (Entranced, Sexual Frustration, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling: 12, 11, 6, 3, 18]
[Hard Wisdom Save Failed!]
[You have gained 2 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity] increased in level. Level 28 ===> Level 30]

[You failed a Saving Throw against your Mistress!]
[Gained Effect: Erectile Dysfunction]

[[Pain into Pleasure] increased in level. Level 7 ===> Level 8]

Raine felt the pressure of his cage decrease as his cock lost the ability to get hard once more. He let out a needy whine as his Mistress withdrew from the painful display of love. He saw her summon her new riding crop, the black staff held forebodingly in her hands. She looked incredibly intimidating and Raine felt a drop of precum fall to the floor as he stared up at her tall form and large boobs.

[[Entranced] increased in level. Level 22 ===> Level 23]

His mistress pulled the riding crop back to strike him, and Raine flinched. The crop struck his balls, causing a dizzying pain and a wave of pleasure as he lost his balance and sank to the floor, soon sprawled on his back.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 1, 2]
[You lost 3 HP!]

Raine saw his Mistress step over him, a psychotic grin etched on her face. The riding crop rose again, striking his prone form as once more a nauseating level of pain radiated from his abused balls. Following this was an immense wave of pleasure, Raine felt like he was about to cum.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 2, 2]
[You lost 4 HP!]

[[Pain into Pleasure] increased in level. Level 8 ===> Level 9]

Then came another strike, once again his sore balls were hit with the crop, causing him to cry from the pain. Yet, more pleasure came from the pain, pushing Raine over the edge and making him cum hard. Cum spewed out his cage painfully as Raine cried.

[Your Mistress, Tazamoth, struck you with [Black Riding Crop]!]
[Critical hit!]
[You took 2d3 Blunt damage!]
[Rolling]
[Rolled: 1, 3]
[Doubling effects]
[You lost 8 HP!]

[You have came in chastity: +0.1% [Feminisation] Progress]
[You have came hands-free: +0.1% [Feminisation] Progress]
[Sexual Frustration decreased in level. Level 29 ===> Level 28]

[A [Succubus] brought you to orgasm! Body sensitivity increased in level. Level 30 ===> Level 31]

[[Succubus Covenant Crest] increased in level. Level 0 ===> Level 1]

[[Pain into Pleasure] increased in level. Level 9 ===> Level 10]

[HP dropped below 10%. Make a Normal Vitality Saving Throw to remain conscious against your Mistress, Tazamoth!]
[Beginning Normal Vitality Save with Disadvantage (Keyheld)]
[Minimum Saving Roll: 12]
[Current Bonus to Vitality: +0]
[Rolling: 10, 7]
[Normal Vitality Save Failed!]
[You are falling unconscious!]
[[Erectile Dysfunction] increased in level. Level 1 ===> Level 2]

Raine saw his Mistress stand over him as his vision faded to black... His last thought before he lost consciousness was that he'd failed his training again.

-----------

Tazamoth's POV

After her Raine passed out when she struck him for the third time, Tazamoth moved over to her Half-Elf. Picking up the abused femboy, she carried him back over to the bed, placing him back down on it. Given that Raine was unlikely to wake up until after a [Short Rest], she decided she'd go to her casting room and make a healing tonic of some sort for her covenanter, so they could continue the training when he woke up.

She first got dressed, whilst she wasn't expecting any visitors, it'd undermine her authority with the maids to just walk around naked all the time. On went her boots, shorts and top. In no time at all, she was out of her room, walking across the hallway and into her casting room. There, she walked past the casting circle towards the alchemy corner. Initially when she'd built the house, she figured she probably wouldn't use it much, but it'd become her second most-used magical station, after the casting circle. While she was no prodigy, she did have a bit of natural talent for the craft, and knew how to make relatively powerful healing potions without resorting to exotic ingredients (by hell's terms at least). Raine's small HP pool meant he didn't need a particularly strong healing potion, so she kept it simple. Opening her cupboard, she retrieved a small bottle of distilled Silver Lustella sap. She'd harvested it herself from the small Silver Lustella (a small bush with pitcher plant like cups dotted across it, it fed on semen and could be quite proactive in obtaining it) that sat on a shelf on the other side of the room. Next, she reached down and took out a ratkin finger bone, placing it in a pestle and mortar and grinding it into dust to create ratkin bonemeal. Finally, she grabbed a small vial of entblood.  She placed them together in a new bottle, and added about 100ml of boiling water before placing a cork in the bottle and shaking it thoroughly. She reached out with magic and teased out the essence of growth in the distilled sap, the super-immunity of the ratkin marrow in the bonemeal and the coagulant properties of the entblood. The impurities started to attack each other, purging themselves from the final product, and the few that didn't were swept away by Tazamoth's mana. She released her hold on the selected essences, letting them settle back into the liquid, causing it to bubble ever so slightly. The final product had taken on a light pinkish hue and was see-through. Tazamoth smiled at her success.

[Created Potion of Demonic Healing: This potion heals 3d6+2 HP, anyone that consumes it who is not a demon will gain 2 levels of [Aphrodisiac Affected](Temporary).] 
[+6 XP]

Not bad at all, sometimes she made this recipe well enough to get 3d6+3 HP out of it, but 3d6+2 HP was already pretty decent compared to the ones you'd find at market. She hoped Raine appreciated it. Given that she'd likely be pain training him more often, perhaps she ought to keep a few of these potions ready at a moments notice, to make their sessions last longer.

She left the casting room, carrying the fresh potion with her back to her bedroom. Raine was still asleep, so she sat down on the bed next to him and placed the potion down next to her. Now, what book should she read until Raine woke up...

-----------

Changes this chapter:

[Special Trait Increased: Feminisation: 4.0% ===> 4.4%]

[Special Trait Increased: Succubus Covenant Crest: Level 0 ===> Level 1]

[Permanent Effect Increase: Pain into Pleasure: Level 7 ===> Level 10]

[Permanent Effect Increase: Body Sensitivity: Level 25 ===> Level 31]

[Permanent Effect Increase: Anal Sensitivity: Level 3 ===> Level 4]

[Effect Gained: Erectile Dysfunction: Level 2]

[Effect Increased: Entranced: Level 8 ===> Level 23]

[Effect Increased: Heightened Submission: Level 8 ===> Level 10]

[Effect Decreased: Mandrake Hangover: Level 4 ===> Level 3]

[Effect Decreased: Sexual Frustration: Level 29 ===> Level 28]

Chapter Text

6 Days since Covenant Formed:

-----------

Raine's POV

[Short Rest: Healing 1d4 HP and 1d3 MP]
[Rolling]
[Rolled: 2]
[HP Increased: 1/25 ===> 3/25]
[Rolling]
[Roll Failed: Already at full MP]

Raine woke up in pain, his balls were in immense pain. He looked down at the abused genitals and saw that large purple-black bruises were forming on them. As the pain of them was felt, so too was the pleasure from [Pain into Pleasure] and Raine let out a whispered moan. Precum lubricated his chastity cage already and he felt incredibly aroused just seconds after waking up. His Mistress heard his quiet noises of sexual gratification and put down her book. The Enochian lettering was unreadable to Raine.

"Welcome back to the world of the waking, Little Raine" his Mistress said, licking her lips with her long tongue.

"S-sorry for p-p-passing out Mistress." Raine apologised profusely.

"Little Raine, I like hurting you. You passing out was very hot my little slut." She consoled him, grabbing something by her thigh.

"Still... I'm sorry I came before you did Mistress."

"Why don't you be a good boy and drink this, my Little Raine?" She said, handing him a small bottle of fizzing pink fluid.

Raine took the bottle, uncorking it. [Dangersense] flared up, but at this point it seemed mostly to alert him to things that would please his Mistress and make him a better plaything, so he paid it no mind. He drank from it, surprised by the taste, which reminded him of the scent of pine resin.

[You drank [Potion of Demonic Healing]]
[Healing 3d6+2 HP]
[Rolling]
[Rolled: 5, 2, 3]
[HP increased: 3/25 HP ===> 15/25 HP]
[[Aphrodisiac Affected](Temporary) increased in level. Level 30 ===> Level 32]

Raine gasped as he finished the bottle. Already he could feel the its effects. The bruises on his nuts shrank somewhat, and the pain decreased slightly. He handed the bottle back to his Mistress who watched him like a hawk.

"Now then Raine, what do you think about continuing our pain training?" She asked.

"Please Mistress, I'd love to continue it. I want to feel your teeth in my neck again." He said.

"Oh, well that can most certainly be arranged, my desperate slut." She said, leaning in closer to Raine.

Her large body pinned his down as she turned his head with her powerful hands, revealing his still scarred neck. Raine felt her fangs sink in around his jugular and pleasure burst through him as his blood spilled.

[Your Mistress, Tazamoth, used [Foolish Bite] on you!]
[Hit!]
[You took 1d8 Piercing damage]
[Rolling]
[Rolled: 5]
[You lost 5 HP!]
[HP Decreased: 15/25 HP ===> 10/25 HP]

[Beginning Hard Wisdom Save with Quadruple Disadvantage (Entranced, Sexual Frustration, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling: 19, 16, 16, 9, 12]
[Hard Wisdom Save Failed!]
[You have gained 2 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity] increased in level. Level 31 ===> Level 33]

[You failed a Saving Throw against your Mistress!]
[[Erectile Dysfunction] increased in level. Level 2 ===> Level 3]

[[Pain into Pleasure] increased in level. Level 10 ===> Level 11]

Raine let out a strangled moan as his Mistress stopped biting him, taking her time to lick the blood up that spilled from the wound.

"Mmmmm. Raine, your pain is delicious." She complimented him

"Thank you Mistress." Raine said as he watched a large bulge strain against his Mistress's shorts.

"I think I'll make you suck my cock now, slut." She said enticingly.

"Please let me service your superior cock Mistress" Raine plead.

With that his Mistress pulled down her shorts, releasing the monstrous cock that'd been straining to break through the legwear. Raine quickly got to sucking at it. He needed more Cum, he hadn't had any in the better part of a day now, and [Semen Addiction] was really starting to take effect. His lips slid down Mistress Tazamoth's pole as he pushed for the base of her shaft. He gagged, the sensation of her huge lady cock hitting the back of his throat slightly painful, yet only bringing more pleasure to him. His tongue swirled around the penis in his mouth as he went down, only stopping as she pushed past his tongue. He stared up at her taking in her perfect Amazonian form and her massive titties.

[[Entranced] increased in level. Level 23 ===> Level 24.]

He continued sucking, drawing his head up and down the demoness's thick, meaty cock with pleasure. Passion flooded his mind as he thought about just how perfect his Mistress was. She let out a moan of appreciation, indicating he was getting her closer to cumming. He picked up the pace, he needed her semen, more than anything. She began to thrust her hips, pumping her cock further into him and stopping him from even so much as slightly pulling back off her cock. She let out more moans, and Raine responded with one of his own, letting out a barely audible moan around his mouthful of powerful demoness dick. Precum dripped onto the bed from his barely-functional penis. Then, his Mistress let out more moans, and grabbed his hair, which was now a good 4 or 5 inches long, almost approaching shoulder-length actually. She pulled him down her cock and let out a victorious roar. Thick, heavy semen flooded into Raine's mouth and down his gullet. He greedily swallowed up his Mistress's seed, licking the glans of her penis after she let go of him.

[You have brought your Mistress to orgasm! +10 XP]
[You swallowed Demon Semen! +2 XP, +0.1% Feminisation]
[[Semen Addiction] increased in level. Level 2 ===> Level 3]
[[Succubus Covenant Crest] increased in level. Level 1 ===> Level 2]

[You have reached Level 4!]
[You gained 1d3 HP, 1d3 MP and 1 Wisdom]
[Rolling]
[Rolled: 3]
[You gained 3 HP!]
[Rolling]
[Rolled: 3]
[You have gained 3 MP!]
[You have 4 Unassigned Skill Points]

"Mistress, I levelled up!" He said excitedly.

"Good job Raine. How about I reward my little Covenanter then." Mistress Tazamoth said.

"Please Mistress." Raine asked.

His Mistress pinned him down on his back, his head against the pillows. She reached one hand down to his caged dick, reaching down and slapping his balls lightly. Raine let out a moan, he couldn't tell if it was from pleasure or pain. His Mistress positioned herself so that her tits were right in Raine's face, forcing him to look at them - not that he needed forcing to gaze upon his Mistress's cleavage. He started sucking on her right tit, desperate to show it the worship it deserved. At the same time, his mistress started slapping his balls, light enough to cause only a moderate amount of pain, and with it only a small amount of pleasure.

[[Entranced] increased in level. Level 24 ===> Level 25]

[[Pain into Pleasure] increased in level. Level 11 ===> Level 12]

Her spanking increased, causing Raine to moan with half a tit in his mouth. Precum dribbled out, coating his pained balls in runny liquid, causing a slight wet slap whenever his mistress struck him. Her pace had increased to 2 small spanks a second by now. Raine couldn't tell if he was about to cry from the pain or the pleasure, and he wasn't sure which he or his mistress would prefer. Tears welled up as each slap brought a jolt of pain to him, followed by the fuzzy warm afterglow of pleasure.

"You like that Raine?" Mistress Tazamoth said

Raine nodded

"I bet you do, you masochistic little slut. I bet you love me turning your worthless little cock and puny, sterile balls into completely redundant features, huh? I bet you love being made into a little sissy for your Mistress."

Raine spoke, "I do Mistress! I love all of it, please keep turning me into a brainless little fuckdoll Mistress."

"Good boy... Why don't you just sink deeper and focus on your Mistress's perfect tits. Fuckdolls don't need to speak unless told to." She whispered seductively.

Raine went back to suckling at his Mistress's tits.

"Mmm... I can't wait until you can't cum anymore Raine, no more dirty man-seed being spilled in my bed, only lovely watery precum wetting your micropenis."

Raine hummed around her tit, feeling more precum spurting out of his cock at the idea as his balls started stinging from the constant slapping.

[[Entranced] increased in level. Level 25 ===> Level 26]

"Cum for me, Raine. Cum and shrink that dick for me." She said

His mistress suddenly slapped his balls hard, causing him to wail out in pain and lust. She grabbed his balls and squeezed, steadily increasing pressure, as well as pain. Soon, Raine found his head overwhelmed with pain and lust. He came hard, thin white spurts of cum leaving his dick, hitting his Mistress's wrist.

[A [Succubus] has brought you to orgasm! Body Sensitivity increased in level. Level 33 ===> Level 34]

[You have came in chastity: +0.1% Feminisation]
[You have came hands-free: +0.1% Feminisation]

[[Pain into Pleasure] increased in level. Level 12 ===> Level 13]
[[Sexual Frustration] decreased in level. Level 28 ===> Level 27]

His Mistress didn't let up though, she just kept slapping his balls. Raine whimpered and whined at the abuse, having thought his Mistress would stop when he came.

"Oh, did my little Raine think I'd stop torturing his balls when he came? How silly, he's my slut and I'm not finished yet, so he isn't either." She said cruelly.

Raine could imagine the sadistic smile plastered on her face right now. Gods, he loved how his Mistress simply took from him what she wanted, it was so hot and Raine would give her everything, anything to sate her hunger. He got back to sucking her nipples, tongue teasing nipples for milk that would never come, the metal barbell dancing in his mouth as he sucked.

[[Entranced] increased in level. Level 26 ===> 27]

"Good boy Raine, sink deeper into that trance for Mistress." She said.

Raine sucked harder, pausing occasionally to let out a pained gasp as his Mistress hit him in the crotch. His thoughts started to go hazy, the pain, arousal and [Entranced] working to make it difficult to think at all.

[[Pain into Pleasure] increased in level. Level 13 ===> Level 14]

"Go on Raine, cum again for Mistress. I know you want nothing more than to be my slutty little failed male. How does it feel to be conquered by a Demoness? Does it feel good? I bet it does Raine, you little whore." His mistress whispered dirtily whilst he sucked futilely on her tits.

"In fact, why don't you kiss your Mistress, as a thank you for turning you into the pathetic little femboy you are now? Can you do that for Mistress?"

Raine stopped sucking on her tits, and his Mistress leant down, her lips pressing against his in a kiss. Her slimy tongue forced its way into his mouth. Soon, her long tongue had entered Raine's throat, and despite him gagging and choking, he continued to kiss his Mistress as she demanded. She started squeezing his balls again, the grip getting stronger much quicker this time. Raine felt himself cum, his eyes rolled back in his head as he lost all thought to the pleasure and pain. He twitched and moaned around his Mistress's tongue, his small penis releasing a few globs of cum once more.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level. Level 34 ===> Level 35]

[A [Succubus] has brought you to orgasm! Body Sensitivity increased in level. Level 35 ===> Level 36]

[You have came in chastity: +0.1% Feminisation]
[You have came hands-free: +0.1% Feminisation]

[[Pain into Pleasure] increased in level. Level 14 ===> Level 15]
[[Sexual Frustration] decreased in level. Level 27 ===> Level 26]

Yet his Mistress didn't let up, maintaining the pressure with which she squeezed his balls in her vice-like grip. Raine cried out again, before tears started pouring down his face as the pain and pleasure started to get to much for him.

"Cum for Mistress again Raine... I want you to experience back-to-back orgasms." she said, still gripping his testicles in her hand.

"Mistress!" Raine cried out, already feeling immensely aroused again.

"Show me what a good feminised boy you are and cum for me again." She demanded.

Raine could feel the arousal building up again. His whole body began to shiver and he let out girlish lust-wails as he came again. This time, only a drop of cum came out, dripping sadly down the tip of his cage and onto his balls.

[A [Succubus] has brought you to orgasm! Body Sensitivity increased in level. Level 36 ===> Level 37]

[You have came in chastity: +0.1% Feminisation]
[You have came hands-free: +0.1% Feminisation]

[[Pain into Pleasure] increased in level. Level 15 ===> Level 16]
[[Sexual Frustration] decreased in level. Level 26 ===> Level 25]

"Good boy Raine. Why don't you rest a bit, whilst Mistress attends to other things?" She asked rhetorically.

Raine could only whimper and nod. It felt like he could barely move. Gods, what his Mistress had done to him was so hot. He lay there panting for a decent while. Finally, a coherent thought came to him. He should check his [Feminisation]. He pulled up its Menu.

[Feminisation Progress: 5.1%

Effects of Progress:

-Skin softness: 105.1%

-Body Hair Growth Rate: 94.9%

-Width of Hips: 5.1mm increase

-Height: 5.1mm decrease

-Penis Length: 2.55% decrease (2.91mm Decrease Hard)

-Penis Girth: 1.275% decrease (0.97mm Decrease Hard)

-Testicle Size: 5.1% decrease [Capped at 90% decrease]

-Sperm Production: 5.1% decrease]

Raine felt a surge of pride in his chest, 0.7% progress in only like half an hour's time was good work. He hoped his Mistress would do more things to him today that feminised him. At some point his Mistress had left the room, to do whatever it was she had mentioned earlier. Raine continued to lie there for a while, he thought about masturbating until Mistress Tazamoth got back, but with his cock caged and his plug in, there wasn't much he could really do. He supposed he could take out his plug, there was no binding curse after all, but he was worried it would upset his Mistress. She'd been training him to take here cock for a while now, but he still hadn't progressed far enough yet - if he interrupted that to cum a little more, he didn't think his mistress would be best pleased.

Then he realised he could just masturbate by hitting his balls like his Mistress had done to him, that way he could increase his [Pain into Pleasure] as well. He moved his hand from his side, lightly tapping his balls, pain ran through him but so did a perverse pleasure. It was harder to do than enjoy the pleasure from his Mistress's gentle slaps, as he remained hesitant to cause himself pain. Still, he began patting his damaged balls, stopping every now and then to let out a moan. Fuck, this was so hot. He kept slapping, determined to bring himself to a climax.

[[Pain into Pleasure] increased in level. Level 16 ===> Level 17]

Raine smacked the red and sore balls a little harder now. He could feel himself getting close now, he pressed on. With a smack he came, useless seed spilling onto the bed as he let out an orgasmic sigh.

[You came in chastity. +0.1% Feminisation]
[[Pain into Pleasure] increased in level. Level 17 ===> Level 18]
[[Sexual Frustration] decreased in level. Level 25 ===> Level 24]

Raine smiled happily to himself, feeling a little light-headed. He hoped his Mistress returned soon. His mind once again wondered back to what he'd look like when feminisation reached 100%. Could he even really be called a He anymore by that point? Would he even care about his cock being played with, currently the cage weighed on his mind slightly, its weight a constant reminder of his inability to get hard. Honestly, he was getting excited at the prospect of downsizing eventually, apparently his cock had already shrank by about 3mm, which'd definitely be noticeable were the thing to come off now. [Ejaculation Addiction]'s side effects included a chance of his penis shrinking, perhaps he could ask his Mistress if there was a way to decrease the roll on side effects. If not, he could always just ask her not to let him cum until he rolled a one - but that would make him lose out on [Feminisation] progress, which would also shrink his cock, so maybe his mistress would say no to that idea. He wondered what else his Mistress might have planned for him - he hoped it included more restraints like that mandrake rope she'd used on him.

The door swung open and his Mistress returned, in one hand she held her cock, the massive thing bulging out of her unzipped shorts that she still wore. She took her top off again, exposing Raine to her breasts once again. 

"Raine, I just got finished casting a spell and it has left me painfully aroused, attend to your Mistress at once." she said as she crashed onto the bed, her large cock swaying as she did so.

Ever the obedient slut, Raine immediately moved between her legs. On all fours he began blowing his Mistress as she lay on the bed, hands behind her head. His slobber soon coated her large shaft and trickled down onto her balls. Raine stroked her cock's base with one hand whilst his mouth serviced the head of the penis. His mistress let out a relieved sigh as he sucked.

"Good boy Raine, you've been getting better at sucking cock recently." She praised him

Raine pulled off her cock briefly, bringing his hand up to stroke her soaked tip, "Thank you Mistress." he said cheerfully.

He dived back down on her cock. This time, he went beyond the head, to about the half-way mark before pulling back up to the head and restarting the motion. His mistress groaned appreciatively. Raine felt precum ooze out of the massive she-cock into his mouth. At the same time, he felt his own precum drip out of his cock and grease his cage. He carried on sucking, soon his Mistress was moaning and nearing climax. He glanced up at her, watching the way her tits rose and fell with each breath, his lips matching the tempo of his Mistress's breathing, up and down, up and down.

[[Entranced] increased in level. Level 27 ===> Level 28]

"Oh fuck! Keep sucking Raine."

"Ahhgn... Good boy Raine."

"Ah! Mmm... Keep going my little slut." She encouraged him on.

All of a sudden, Raine felt his mouth flood with semen. He eagerly gulped it down, the thick stuff leaving a slimy trail down his throat. He relished its salty flavour and its viscous goopy texture.

[You have brought your Mistress to orgasm! +10 XP]
[You swallowed Demon Semen! +3 XP, +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 2 ===> Level 3]
[[Semen Addiction] increased in level. Level 3 ===> Level 4]

"Hahhh... Good job Raine." Mistress Tazamoth complimented him.

"Thank you Mistress. What now Mistress?" Raine asked.

"I was thinking you could suck on my tits for a while Raine." His Mistress proposed.

"Awesome, thank you Mistress!" Raine responded, crawling to lie next to her.

"It's getting quite late actually, why don't we get in bed properly and I'll tell you about what I was doing yesterday and whilst you were out?" Mistress Tazamoth suggested.

"Ok Mistress." Raine said, slipping underneath the covers.

His Mistress followed suit and he was soon embraced in a hug by her and squashed into her tits, his mouth practically forced open to accept the teat by the strength of the embrace. Soon his tongue was swirling around her nipple interspersed with sucking.

"Mmm... I'm going to need another covenanter just to suck my other nipple at the same time... I'm sure I could find another bitch, even if they aren't as obedient and easy to train as you are Raine. Would you like that Raine?" She asked.

Raine briefly relinquished his grip on her tit.

"Yes Mistress, a friend to help service you would be nice." He said.

"Good Boy Raine, unfortunately it'll have to wait a while, it's generally frowned upon to get another covenanter if any of your current ones are below level 10."

"Oh, sorry Mistress." He said.

"We'll work on fixing that tomorrow Raine. Once you're at level 5 I can start bringing you to the Middleplane with me. I might have gotten out of mandatory weekly summonings for 2 weeks, but that doesn't mean I can't bring you on a couple voluntary ones to help you level. Speaking of friends though, do you remember Mistress Azzadzime, who did your piercings? She invited me over for a get-together in 4 days time. She has her own Covenanter, an Elf called Lucky. I said I would bring you and you two could have a play-date whilst we talk. Does that sound good?" She explained.

"Yes Mistress... I-if I may ask th-though, what s-s-sort of elf is Lucky?" Raine said, nervously.

"I'm not sure what her subspecies is, but I have my suspicions. Why do you ask?" His Mistress asked.

"Sun Elves and Moon Elves tend not to be very favourable to Half-elves like me. They hate us almost as much as they hate each other. When I was in the academy they wouldn't let me near them, and they were practically the only other elves there, since Inglia, the nation you took me from, is majority human and they all hated us Elves and Half-Elves... My friends consisted of the only other Half-Elf there, and a couple of Wood Elves. I saw the Wood Elves die when we were attacked by those bandits a-and, Willow - the Half-elf - she must've died before they even got to us. She was in the gardens when we were attacked..." Raine confessed, tearing up at the reminder of his friends deaths.

"I'm sorry to hear that Raine..." His Mistress said, genuinely saddened, her own elf-like ears drooping slightly, "I'm sure your friends would be glad to know you survived at least. You won't have to worry about prejudice from Lucky though, Ioketara doesn't believe in the sorts of discrimination common in the Middleplane. If she does say anything that upsets you though, we'll leave. I'm not going to associate with a Demoness who lets her covenanters hold onto such ideas."

"I- Thank you Mistress... You don't have to d-do that on my behalf..." Raine said between tears.

"Shh sh sh... It's okay Raine, I want to do that for you." His Mistress admitted.

Raine sniffled, calming down slightly.

"How about I tell you what I've been doing recently then, to take your mind away from all that? All you have to do is listen darling..." 

"Yes please Mistress... Thinking about Willow and the others, it hurts sometimes." Raine said.

"Well, do you know of the Duchy of Larjenne?" His Mistress asked as a start.

"Yeah, they're an island nation off the coast of Inglia Mistress. Apparently they have a large elven minority there."

"Well, I was summoned there by a nun. Turns out her parents had shipped her to a convent because she was caught kissing a girl. Larjenne is apparently very homophobic by the way. Anyway, she wanted to have sex with a woman and was willing to pledge her allegiance to Ioketara for it. So I spent about an hour corrupting her, before showing her my penis - she was kind of freaked out about that one, but was more than willing to let me fuck her with it after I explained that Demons aren't fertile until at least level 100 despite reaching maturity at level 10." She said, pausing for a second to look down at Raine, who looked up at her with one tit in his mouth, clearly listening despite his suckling.

[[Entranced] increased in level. Level 28 ===> Level 29]

"Anyway, this took like half an hour to explain, and so while I was balls deep in her, another nun walked in to the prayer room. Fortunately, I was able to convince her as well, turns out pretty much all the nuns there are at least bisexual, the convent's apparently where 'troublemakers' are sent. So then I spent another 5 hours shagging the two of them. I got about 10,000 XP from that, since they lost their classes and levels thanks to them breaking their vows of chastity. That's why holy folk are such good sources of XP by the way." She said.

[[Entranced] increased in level. Level 29 ===> Level 30]

"Now, Ioketara has two more agents within the church of Larjenne. They'll be working to corrupt the rest of the convent. When I went to the casting room earlier, it was to cast a spell on the convent to increase their arousal and make it easier for them to corrupt their brethren." His Mistress said, stopping to take a breath as Raine's mouth brought her pleasure.

"Anyway, the whole plan right now in Ioketara is for us to corrupt Larjenne from the inside and then invade it. Honestly, we're getting pretty close. Even one of the Duke's daughters is on the plot now. If we capture Larjenne, we'll finally have a place in Middleplane of our own. I'm sure you've heard of great demon empires forming in the Middleplane before, right Raine? This is how it generally happens. Ioketara is a bit late to the game really." His Mistress revealed.

"Like how Demons took over the Republic of Tsenisara a few centuries ago?" Raine asked, having stopped sucking for a moment.

"Yeah, they're from the layer of fraud though, they basically managed to buy the country out from underneath the president" Tazamoth said. "Since Ioketara is a lust-layer nation we'll be fucking it out from under them. Matriarch Ioketoth herself has apparently taken the Duke's corrupted daughter as a concubine. I might even take you up during the invasion, it's like a month away now, since we have to move before the Duke's daughter selene is shipped off to marry a suitor. We can't delay any longer, since she's already 20 and the Duke will no longer let her refuse marriage to a foreign prince. I'm sure you can tell that Larjenne is not a nation where males are subservient as they should be."

"Wow, that sounds wonderful Mistress. I'd love to help you in the invasion." Raine said.

"We've been working on using Hypnosis through public Magic Mirrors to help teach males their place. They've been broadcasting all sorts of messages here in hell for covenanters as a trial. I could put on some feminisation hypnosis for you tomorrow to try if you'd like."

"Yes please Mistress. That'd be great Mistress." Raine said, before getting back to sucking at her large tits.

[[Entranced] increased in level. Level 30 ===> Level 31]

The pair of them settled into a comfortable silence, only broken by the occasional moans and the constant suckling of Raine on his Mistress's luxurious teat.

[[Entranced] increased in level. Level 31 ===> Level 32]

[[Entranced] increased in level. Level 32 ===> Level 33]

[[Entranced] increased in level. Level 33 ===> Level 34]

"Mmm... That's it Raine, sink deeper for Mistress..."

[[Entranced] increased in level. Level 34 ===> Level 35]

"Let go of all your thoughts and focus on your Mistress. Femboy Fucktoys don't need thoughts beyond their Mistress... Focus only on your Mistress and her massive tits... Forget about anything else... Good boy Raine..."

[[Entranced] increased in level. Level 35 ===> Level 36]

"Good boys don't need to think hard Raine... Be a good boy and focus on Mistress..." Mistress Tazamoth whispered gently, running a hand through his hair

[[Entranced] increased in level. Level 36 ===> Level 37]

"Ssshhhh... Good boy..." She said, as Raine felt his eyelids grow heavy.

'I'm a good boy' Raine thought as he began to drift off.

[[Entranced] increased in level. Level 37 ===> Level 38]

"Let all those worries slide off you, Little Raine..."

[[Entranced] increased in level. Level 38 ===> Level 39]

[[Entranced] increased in level. Level 39 ===> Level 40]

[[Entranced] increased in level. Level 40 ===> Level 41]

Raine was asleep before he finished reading the notification.

-----------

Changes this chapter:

[Level up: Level 3 ===> Level 4]

[Special Trait Increased: Feminisation: 4.4% ===> 5.3%]

[Special Trait Increased: Succubus Covenant Crest: Level 1 ===> Level 3]

[Permanent Effect Increased: Body Sensitivity: Level 31 ===> Level 37]

[Permanent Effect Increased: Pain into Pleasure: Level 10 ===> Level 18]

[Permanent Effect Increased: Semen Addiction: Level 2 ===> Level 4]

[Effect Increased: Entranced: Level 23 ===> Level 41]

[Effect Increased: Aphrodisiac Affected: Level 30 ===> Level 32]

[Effect Increased: Erectile Dysfunction: Level 2 ===> Level 3]

[Effect Decreased: Sexual Frustration: Level 28 ===> Level 24]

Chapter Text

7 Days since Covenant Formed

-----------

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 7]
[HP Increased: 10/28 HP ===> 17/28 HP]
[Rolling]
[Roll Failed: Already at full MP]

[Special Trait Progress Increased: Feminisation: 5.3% ===> 5.4%]

[Permanent Effect Increased: Body Sensitivity: Level 37 ===> Level 39]

[Permanent Effect Increased: Anal Sensitivity: Level 4 ===> Level 5]

[Effect Decreased: Mandrake Hangover: Level 3 ===> Level 2]

[Effect Decreased: Entranced: Level 41 ===> Level 40]

[Effect Decreased: Heightened Submission: Level 10 ===> Level 9]

Raine woke up with a start, waking up his Mistress as well. He hadn't even realised he fell asleep last night, and had jolted awake whilst smothered in her tits, worried he'd offended her by drifting off for a second. As he read through his notifications, the notion was quickly dispelled. As nice as it would be, Raine could not get a [Long Rest] from just a couple seconds of sleep.

"Sorry Mistress, I didn't realise I was sleeping until I woke up." He apologised.

"No worries, I suppose we can get you started on that Hypnotism now." His Mistress said cheerily, "If we both like what it does to you, we can try some 1-on-1 hypnotism eventually."

"O-ok Mistress." Raine stuttered, relieved he hadn't offended his Mistress by waking her up.

"Now, be a good boy and lie down in the centre of the bed, arms and legs spread out." She said, getting out of the bed.

Raine did as he was told, utterly obedient for his Mistress. He watched as she summoned 4 coils of mandrake rope, her eyes flashing green. She grabbed one of his wrists, tying the rope around it. She tied the other end to one of the bed posts. Then she moved down, tying a similar knot around his ankle before attaching that rope to the nearest bed post. She walked around the other side, tying his other ankle first, securing it once more. Raine found the Ropes were tight enough to force his legs apart somewhat. By now, he was thoroughly aroused and precum greased his chastity cage. His Mistress began tying his other wrist up.

[[Heightened Submission] increased in level. Level 9 ===> Level 10]

"Mistress, when can I downsize my cage?" Raine asked.

"Eager to reduce it even further are we?" Mistress Tazamoth asked

"Yes Mistress."

"Well, the next size I have for you is 2 inches in length, which is still a bit small you I think right now. We're taming your manhood, not crushing it entirely. You still want it to work right?" She explained.

"I mean, I already have [Erectile Dysfunction] and [Feminisation] to stop me from getting hard and producing semen Mistress. I don't think it'll be working much longer anyway. I didn't think you wanted working and that's all I care about Mistress" Raine admitted.

"I suppose you're right Raine, it is already sort of broken and I do like that, I want your little cock breaking properly. In that case, we'll downsize your cage after you watch the hypnotism. Besides, on Half-Elves, a cock is mostly for decorative purposes anyway, it wasn't like you were going to be able to do anything with it anyway." His Mistress said in realisation as she finished tying the last of the ropes.

"Thank you Mistress. I just want to be your perfect femboy." Raine said, "Also, are these mandrake ropes Mistress?"

"Yes Little Raine, did my little slut enjoy them last time?" She asked him

"Yes Mistress, I enjoyed being [Mandrake Drunk], and I enjoy how weak and pitiful the hangover makes me..."

"Well my Little Raine, you'll be glad to know that you'll be in these restraints a lot longer than last time. I intend to leave you here until I come back to bed." She revealed

Raine's caged cock twitched at the reveal. That meant he'd fail his addictions and gain even more [Sexual Frustration], he couldn't wait.

"Now little Raine, they unfortunately don't have any Half-Elf specific Hypnotism available, so I'll put on the Elf specific stuff okay? I assume you'd prefer that over the human stuff at least." She said.

"Yes Mistress, I'd prefer Elven stuff over Human stuff most of the time." He answered.

"Hmm. I'll make note of that for the future." Mistress Tazamoth said.

With a snap of her fingers and a green flash, the mirror floated off of the wall, drifting over to the bed, where it planted itself in the roof of the canopy. Raine was left staring up at his reflection. He looked utterly pathetic, squirming pointlessly in restraints on a Demoness's bed. Suddenly, the mirror turned pink. Raine felt a psychic tendril press at his mind. He let it in without any restrictions. A spiral of pink and purple shifted onto the screen, he felt as though he couldn't look away.

"Now be a good boy and watch the spiral for Mistress, Raine." His Mistress said, and he heard the door close.

[Gained Effect: Mandrake Drunk]

[Unrestricted Hypnotic Link Formed between [Ioketaran Hypnotic Broadcast] and your Mind!]

[Beginning Impossible Wisdom Save with Quintuple Disadvantage (Entranced, Sexual Frustration, Mandrake Drunk, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: >20]
[Current Bonus to Wisdom: +0]
[Rolling: 14, 12, 3, 5, 1!, 9]
[Impossible Wisdom Save Critically Failed!]
[All subsequent Hypnotic Effects during this Hypnotic Link Doubled!]
[You will receive a -1 bonus to Saves against all subsequent Hypnotic Links with [Ioketaran Hypnotic Broadcast]!]

An amazing start, god his Mistress was going to be so proud of him. He focused on the swirl as it began. Words soon began to flash in front of the spiral.

Beginning Feminisation Hypnotic Spell One

Elf 'Male' Detected!

Correction beginning...

Erase your Masculinity.

Accept your new lifestyle.

Become Feminine.

[[Entranced] increased in level. Level 40 ===> Level 42]

Bow before Demonesses.

Worship Demonesses.

Service Demonesses.

[[Entranced] increased in level. Level 42 ===> Level 44]

Demons are superior to Elves.

Demons are stronger than Elves.

Demons are smarter than Elves.

Demons have bigger cocks than Elves.

[[Entranced] increased in level. Level 44 ===> Level 46]

Elves have small penises.

Elf women want more.

Elf women want Demonesses.

[[Entranced] increased in level. Level 46 ===> Level 48]

Elf women will forget you.

So why bother with Elf women?

[[Entranced] increased in level. Level 48 ===> Level 50]

The screen returned back to just the spiral for a while. Raine focused on it, his eyes glazing over.

'Why would I bother with Elf Women... I have Mistress...' he thought.

Words started flashing onto the mirror again.

Elven 'masculinity'? hah!

Elves are naturally feminine.

Elves are naturally submissive.

[[Entranced] increased in level. Level 50 ===> Level 52]

Elf women don't want submissive partners.

Elf women don't want small penises.

Elf women don't want Elf men.

Elf women want Demonesses.

Elf women want Demoness Cock.

[[Entranced] increased in level. Level 52 ===> Level 54]

Elf women want Big, Hard, Throbbing Demoness Cock.

Elf women were made for Big, Hard, Throbbing Demoness Cock.

Elf women need Big, Hard, Throbbing Demoness Cock.

[[Entranced] increased in level. Level 54 ===> Level 56]

Elf women don't need submissive partners.

Elf women don't need small penises.

Elf women don't need Elf men.

Elf women need Demoness Cock.

[[Entranced] increased in level. Level 56 ===> Level 58]

Elf women need Demoness Semen.

Elf women need Demoness Sex.

Elf women need Demoness Owners...

[[Entranced] increased in level. Level 58 ===> Level 60]

The text stopped for a second. Raine let out a moan and shook in his restraints slightly. He could feel the Hypnosis really beginning to set in, [Entranced] was levelling super fast, and he could barely pay attention to the notifications.

'Elves need Demonesses...' he thought. 'Elf women belong to Demonesses. Elf women don't want my small cock...' he thought, drooling slightly.

The words began again, drilling themselves into his mind.

Elves are a failed species.

Elves need the guidance of others.

Elves need the guidance of Demonesses.

[[Entranced] increased in level. Level 60 ===> Level 62]

Elves are a defeated species.

You are a defeated Elf.

You need guidance.

[[Entranced] increased in level. Level 62 ===> Level 64]

Elf men don't know what's best for them.

Elf men are too obsessed with being 'Masculine'.

Elf men can't be 'Masculine'.

[[Entranced] increased in level. Level 64 ===> Level 66]

Elf men are lost.

Elf men need guidance.

Elf men need Demonesses to guide them.

[[Entranced] increased in level. Level 66 ===> Level 68]

Elf men are defeated

Elf men are pathetic

Elf men are pitiful

[[Entranced] increased in level. Level 68 ===> Level 70]

You are defeated.

You are pathetic.

You are pitiful.

You are Conquered...

[[Entranced] increased in level. Level 70 ===> Level 72]

You should embrace your femininity.

You should embrace your defeat

You should embrace your overlords.

[[Entranced] increased in level. Level 72 ===> Level 74]

You need femininity.

You need defeat.

You need your overlords.

[[Entranced] increased in level. Level 74 ===> Level 76]

"...I need defeat..." Raine spoke absently. Saliva ran down his cheek onto the bed, forming a growing wet patch.

You want femininity.

You want defeat.

You want your overlords.

[[Entranced] increased in level. Level 76 ===> Level 78]

You should embrace Demonesses.

You need Demonesses.

You want Demonesses.

[[Entranced] increased in level. Level 78 ===> Level 80]

You want Demoness Pussy.

You want Demoness Tits.

You want Demoness Ass.

[[Entranced] increased in level. Level 80 ===> Level 82]

You can have Demoness Pussy.

You can have Demoness Tits.

You can have Demoness Ass.

[[Entranced] increased in level. Level 82 ===> Level 84]

You only have to SUBMIT.

[[Entranced] increased in level. Level 84 ===> Level 86]

"I should... Ah. Submit..." Raine said, moaning slightly. The pink spiral had him so turned on, yet his restraints and his cage stopped him from doing anything about it. He could feel himself going kind of crazy.

Become feminine.

Become weak.

Become a Femboy.

[[Entranced] increased in level. Level 86 ===> Level 88]

"Mmmm... Femboy... weak..." Raine said happily to himself. He could do that, especially if it were for his Mistress.

Let a Demoness control you.

Let a Demoness own you.

Let a Demoness fuck you.

[[Entranced] increased in level. Level 88 ===> Level 90]

Let a Demoness become your Mistress.

Only Demonesses want pathetic feminine elf men.

Only Demonesses want you.

[[Entranced] increased in level. Level 90 ===> Level 92]

"Uhhh.... Mistress. Mmm... Want me..."

Raine's cage jiggled as he flexed his cocklet within it. The whole device moving as the useless member twitched. Raine stayed focused on the spiral. He could feel [Dangersense] pinging in the back of his mind. [Dangersense] always went off when he was making his Mistress happy. Raine giggled.

Don't breed with Elf women.

Breed with a Demoness.

Breed with your Mistress.

[[Entranced] increased in level. Level 92 ===> Level 94]

Elf women have forgotten about Elf men.

It's time for Elf men to forget about Elf women.

It's time for you to forget about Elf women.

[[Entranced] increased in level. Level 94 ===> Level 96]

Let the Elf Species decline.

Let the Elf Species take it's rightful place.

Let the Elf Species become Demoness property.

[[Entranced] increased in level. Level 96 ===> Level 98]

Elves let themselves be fucked

Repeat aloud

'Elves are for sex'

"Elves...are for... sex. hehehahe." Raine giggled. Saliva was starting to pool by his head, and precum soaked into the bed around his crotch.

[[Entranced] increased in level. Level 98 ===> Level 100!]

"Elves. Are for sex" Raine said absently.

Repeat.

'I am an elf'

'Elves are for sex'

"I am an elf... Elves are for sex... ehehe" Raine said again, letting out a little giggle. He was for sex.

[[Entranced] evolved!]

[Gained Permanent Effect: Hypnotised]

[[Hypnotised] - Ideas and commands have been implanted in your mind in a practically irreversible manner. You gain double disadvantage on Wisdom and Intelligence Saving Throws. +100% Arousal. +1% arousal per level if a sapient you've had sex with is within Line of Sight or is within 100 feet of you. Depending on what hypnotised you, your behaviour may change!]

[Feminisation Curse: Secret Condition Met: Become Hypnotised: +0.2% Feminisation]

Good Boy…

Elf Feminisation Initial Hypnosis completed

Running status checks…

Several hastening factors detected (willing, chastity, plug, feminisation progress, restrained, covenant)

Running femboy through fast-track hypnosis path…  

Running Elf Sissy Hypnosis Spell One

The spiral morphed, revealing a video of an elf woman. She was sucking a huge demoness’s foot-long cock. Words once more flashed onto the screen.

You want to be like her.

You want to suck like her.

You want to fuck like her.

The video morphed, showing the elf riding the girthy shaft she’d been slurping on before. Raine could hear her moans as the elf and demoness slapped their crotches together.

You want to be her…

[[Hypnotised] increased in level. Level 2 ===> Level 4]

But you’re a man…

Are you?

It’s ok to give in.

It’s ok to be a femboy

It’s ok to be a sissy

[[Hypnotised] increased in level. Level 4 ===> Level 6]

“Mmmmmm… femboy… sissy.” Raine said, his tongue feeling heavy.

It’s ok to crave cock.

It’s ok to want to be fucked.

It’s ok to devote yourself to a Mistress.

The image morphed to a side by side comparison of an elf’s penis and a demoness’s penis. The elven one was barely 2 inches long, whilst the demoness’s looked to be at least 13 inches.

Afterall, it’s only natural.

Isn’t it?

Elves are for sex.

[[Hypnotised] increased in level. Level 8 ===> Level 10]

The mirror morphed, showing Raine a range of different Elven femboys being fucked brutally by demonesses.

Become addicted to sex.

Become addicted to sucking dick.

Become addicted to anal.

Become bisexual.

Become a femboy.

Become a sissy.

It’s only natural.

Elves are for sex.

“Elf… Sex. Natural” Raine managed. He could barely feel or see anything other than the mirror now.

Wear girls clothes

Wear make-up

Wear a chastity cage

It’s only natural.

Elves are for sex.

[[Hypnotism] increased in level. Level 10 ===> Level 12]

Be a good boy for your Mistress.

Good boys don’t think except for sex.

Good boys let their Mistress think for them

You’re a good boy right?

"Yes... Please, I- I need... Good boy." Raine stuttered out. By now, precum was oozing out of his cage. He bucked his hips subconsciously - grinding on something that wasn't there.

[[Hypnotism] increased in level. Level 12 ===> Level 14]

Good Elf boys lock their cocks away.

Good Elf boys do anal.

Good Elf boys cum to hypno.

It's only natural

Elves are for sex.

CUM.

Raine suddenly found himself enjoying a ruined orgasm. Semen dripped from his cage, dribbling down his balls and dripping onto the bed. He let out orgasmic grunts and groans, hands instinctively trying to reach his cock, but barely budging thanks to the ropes.

[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came while being Hypnotised. +0.2% Feminisation]

[[Hypnotised] increased in level. Level 14 ===> Level 16]

[[Mandrake Drunk] increased in level. Level 1 ===> Level 2]

[[Sexual Frustration] decreased in level. Level 24 ===> Level 23]

Good boy...

With those final words, the video ended, returning to the simple pink spiral that had transfixed Raine earlier. Raine found himself giggling uncontrollably and whispering to himself about elves and sex. He wasn't at all sure why that was so funny. Soon however, Notifications came in.

[[Ioketaran Hypnotic Broadcast]'s hypnotism is attempting to apply various additional effects on you!]
[Beginning Very Hard Wisdom Save against [Ioketaran Hypnotic Broadcast] with Sextuple Disadvantage (Hypnotised(2), Sexual Frustration, Mandrake Drunk, Mental Weakness Curse, Keyheld)]
Minimum Saving Roll: 18]
[Current Bonus to Wisdom: -1]
[Rolling: 4, 7, 13, 19, 15, 4, 10]
[Very Hard Wisdom Save Failed!]
[+1% Feminisation]
[[Hypnotised] increased in level. Level 16 ===> Level 21]
[[Sexual Frustration] increased in level. Level 23 ===> Level 24]
[[Semen Addiction] increased in level. Level 4 ===> Level 5]

Elf Sissy Hypnotism Spell One completed

Running status checks...

Extremely rapid hypnotism has lead to temporary mental destabilisation...

Inducing unconsciousness to prevent destabilisation and allow for healing...

Raine felt the slightest twinge of worry at reading that. However, his consciousness left him before it could become anything more, everything faded to black as he passed out, feeling exhausted.

-----------

Tazamoth's POV

Mistress Tazamoth sighed as she finished another glass of Dwarven Bloodwine. She'd left Raine to marinate in the hypnotism for a couple hours now and after attending to a couple chores had been enjoying a large selection of different wines she had in her cellar - she hadn't drank in ages. Alcohol always made her horny, and now was no exception, she was finding it hard to resist the idea of returning to the bedroom and fucking Raine's ass silly, regardless of how much anal training he'd received. Hells, he'd probably thank her if it hurt. Her femboy's anal virginity was something that definitely needed correction, and one that she would relish in correcting. She wondered how he was doing now. Hmm, she guess she'd find out later, she poured another glass and began drinking. Maybe she would fuck his ass tonight, depending on how the hypnotism turned out.

[[Drunk] increased in level. Level 3 ===> Level 4]

-----------

Raine's POV

[Short Rest: Healing 1d4 HP and 1d3 MP]
[Rolling]
[Rolled: 3]
[HP Increased: 17/28 HP ===> 20/28 HP]
[Rolling]
[Roll Failed: already at full MP!]

[[Mandrake Drunk] increased in level. Level 2 ===> Level 5]

Raine came too, feeling incredibly horny, eyes closed. Freshly conscious he realised how out of it he'd been when staring at the mirror. The whole thing had been incredibly hot, especially now that he knew that elves were supposed to be Demonesses' fucktoys. Something about that felt so right to him, almost religiously so. He supposed that was the hypnotism speaking - he probably wouldn't have disagreed with the idea beforehand, but after the hypnotism it felt somehow more, like his understanding of the concept had deepened. He giggled lightly.

Open your eyes

A voice in his head spoke, he found himself complying, blinking away the tiredness. Once again, he was confronted with the pink spiral in the mirror.

Running status checks...

Mental signs returned to normal, caution advised to avoid further destabilisation events for the time being...

Modifying spell list...

Elf Cultural Corrections Spell One Selected.

Beginning Cultural Corrections Spell One...

Raine frowned, this seemed like it'd cause less change than the previous two. Had he done something wrong? He thought he was a good boy... Was he not a good boy? Panic gripped Raine at the idea. He needed to be a good boy for his Mistress.

Elf detected, beginning cultural corrections...

Ioketara, unlike the vast majority of Elven societies, is a matriarchy. This is the natural order of things, unlike the gross perversion of nature that is the patriarchal clan system most elves adhere to. To successfully integrate into Ioketara and be a good boy, you must abandon these ideas. Good boys assimilate into Ioketaran Matriarchy. Good boys report males who deny the superiority of Demonesses.

Raine could do that. Raine could be a good boy. He nodded enthusiastically.

Let's begin by explaining the system of Hierarchy within the Matriarchate of Ioketara. The ruler of our glorious nation is Ioketoth, a daughter of Lilith herself! She rules through her position as Matriarch and High Queen of Ioketara. Ioketoth is assisted by her most mightiest of vassals, and only peers, the Queens of Ioketara. Unlike in many places in the Middleplane, a Queen of Ioketara is not a sovereign ruler, just the mightiest of Vassals. A Queen merely denotes a Demoness of the level 1,000 or higher. Many of the Queens of Ioketara are the children of Ioketoth, though others are unrelated to her Great Majesty.

Below the Queens of Ioketara are the various nobles. Within Ioketara, there are 6 ranks of nobility. Ordered from highest to lowest these are: Duchesses, Marquises, Countesses, Viscountesses, Baronesses and Ladies. A Demoness is considered a noblewoman when she reaches Level 100 and undergoes a transformation. Subsequent transformations occur with each increase in noble rank. A Lady is a Demoness between the levels of 100 and 149. A Baroness is a Demoness between the levels of 150 and 199. A Viscountess is a Demoness between the levels of 200 and 299. A Countess is a Demoness between the levels of 300 and 399. A Marquise is a Demoness between the Levels of 400 and 499. Lastly, a Duchess is a Demoness between the levels of 500 and 999. Although they undergo no transformation, a Duchess of level 750 or greater is entitled to call themselves a Grand Duchess. The highest level Duchess in a Queendom is entitled to refer to themselves as an Archduchess.

Raine imagined how powerful a Duchess would be. His Mistress wasn't even a noble yet and she was still so powerful that Raine knew she could easily kill him if she really wanted. Imagining his Mistress at such a powerful level cause a tear of precum to drip down his cock.

[[Hypnotised] increased in level. Level 20 ===> Level 22].

Noble Demonesses are far more powerful than elves such as you. If you have encountered Demonesses in the Middleplane before Ioketara took over, it is highly unlikely that they were nobles, most summonings aren't strong enough to summon them. You were so weak that almost all the trouble caused to you before Ioketara conquered you was done by common demonesses. For this reason, resistance is futile. How could you ever hope to stand up against a Demoness-Queen? Give in...

Common Demonesses are split into 3 separate grades - Greater Demonesses, Lesser Demonesses and Imps. Greater Demonesses are those between the levels of 50 and 99, they are larger and stronger than all but the most powerful races on the Middleplane. Greater Demonesses make up about 15% of the Ioketaran population. Lesser Demonesses are those between the levels of 10 and 49. At level 50, they undergo a physical transformation that makes them much more powerful. Lesser Demonesses make up 84% of the Ioketaran population. Imps are the larval form of Demonesses, and exist between level 0 and level 9. Imps are generally not counted as part of the population, as their only purpose is to fight, kill and fuck other Imps until they reach level 10. Imps are rarely born, instead being formed from excess emotions from the Middleplane.

Every dirty thought in your mind goes towards creating more of us. We are undying, unwavering and unstoppable... Give in...

[[Hypnotised] increased in level. Level 22 ===> Level 24]

So, where do you fit in, Middleplaner? Well, that depends on many things... Firstly, all non-demonesses are inferior to all demonesses. This is a biological fact. Secondly, if you are a woman, you are now superior to any males in your life. Males will face extensive legal restrictions. Legal restrictions on males will include: inability to own property, preference for women in inheritance, and curfews in some areas. Sadly, since Middleplanar women generally cannot become Futanari (this term will be explained later, middleplaner), Males will unfortunately be required for maintaining your population. Thirdly, all religions except for demon worship shall be banned.

You are encouraged to form a covenant bond with any Demoness you come across. In exchange for access to the Demoness's immortality, you will be required to serve your new Mistress in any way she may require. It is likely that your Mistress will be a Greater Demoness. Covenanters will be considered superior to all other middleplaners with the exception of concubines. Concubines are a special form of covenanter required to love their Mistress, promotion to Concubinage is a complex topic that will not be covered in this spell, but there are level requirements.

Most Demonesses are Futanari. A Futanari is a Demoness that possesses both a penis and a vagina, and may switch between either at will. Futanari are the most supreme beings, better than other females and entirely superior to the failed specimens known as males.

Moving onto cultural norms. As you know, most elves wear relatively light clothing that reveals a lot of skin and or is very skin tight. This is an admirable cultural trait that Ioketara encourages. Moreover, it is further evidence that Elves are made for sex.

"ehe, elves are for sex, hehehe-ehe." Raine giggled to himself. He wasn't sure what about it exactly was so funny, but perhaps it was the fact that he took so well to the training his Mistress had put him through so far. Or maybe the fact that he'd never realised the purpose of elves and half-elves like him before, despite it being obvious now.

[[Hypnotised] increased in level. Level 24 ===> Level 26]

However, elf culture is not perfect. Not yet, at least. One cultural taboo found in almost all elf groups is ear piercings. Many elves hold that having unpierced ears is a sign of moral superiority and cleanliness. This is untrue. The whole reason why elves have long ears is for them to be pierced many times. Elves are especially mouldable physically and piercings can be enchanted to perfect your elven forms. If you are a covenanter, your Mistress will likely take you to get your ears pierced. You are not to complain, you are to comply. You should abandon these silly superstitions and beliefs and adopt Ioketaran culture. You want to assimilate. A lack of piercings is not a sign of moral superiority. Elves are superior in only one role - as fucktoys. Other issues such as an aversion to polygamy and interspecies relationships are common in elf populations. This will not be permitted or allowed to continue.

Elves speak many languages. Demonesses speak only one. All will have to learn the language of Demons - Enochian. It is Ioketara's right as your conquerors to impose this language on you. You will assimilate.

Repeat, 'I will assimilate.'

"I will assimilate" Raine said, moaning as he leaked fluids onto the bed again. His eyes were glazed over, he felt the pink spiral beaming each word into his head. It was impossible to resist speaking them aloud. Raine didn't want to resist speaking them aloud.

Repeat, 'Elves are inferior to Demonesses'

"Elves are inferior to Demonesses" Raine said. He felt the spiral provide him with a bit of pleasure in response to the co-operation.

Repeat, 'I am inferior to Demonesses'

"I am... mnph... inferior to Demonesses" Raine managed around a moan, his eyes rolled back in his head slightly. He was an inferior little Half-Elf who needed a mistress to guide him, to fix him, to make him a good boy.

Repeat, 'I will be a good elf.'

"I will... ah! be a good half-elf" Raine said, feeling huge waves of pleasure wash across him. He was once again on the verge of climax, the spiral rewarding him for his obedience. 

Good Elf. CUM...

Raine moaned, his whole body lit up with lust as the spiral bombarded his weak mind with pleasure. Ropes of cum spurted from his cage, painting his tummy in the sticky white fluid.

[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came while being hypnotised. +0.2% Feminisation]

[[Hypnotised] increased in level. Level 26 ===> Level 28]

[[Sexual Frustration] decreased in level. Level 24 ===> Level 23]

Raine felt light-headed again. He was probably going to pass out again but that didn't matter because he was a good boy. He was going to make his Mistress so proud with how much he loved hypnotism. Slowly his eyes closed involuntarily, if he had any say, they'd remain watching the spiral like a good boy's eyes would. Sadly, his body betrayed him and he sank back into unconsciousness.

-----------

Tazamoth's POV

Tazamoth massaged the erection in her shorts. She was just going to finish drinking this next bottle of bloodwine. This one was a Gnome-Human blend, a strange pairing for certain but she couldn't say she disliked the combination of herbal and metallic undertones. This was her fourth bottle now, and although she had a much higher tolerance for alcohol than a human would, it was safe to say she was pretty smashed. She emptied her glass, drinking the alcohol quickly and without the decorum she had given the first two bottles.

[[Drunk] increased in level. Level 14 ===> Level 15]

Fuck, she needed to plough Raine. She wondered how he'd look when she slid her fat cock into his ass. Actually, she wondered what he'd look like drunk as well. She really ought to get some Middleplane alcohol to give to Raine. 'Moth would bet anything that her Half-Elf was a total slut after alcohol passed his lips. To be fair, he was already quite the slut when sober. He was a good boy and Tazamoth couldn't wait to fuck him. Rather than pour herself another glass she just grabbed the bottle and pressed it to her lips, gulping down the red liquid. She finished it with a satisfied sigh, wiping a loose dribble off of her chin.

[[Drunk] increased in level. Level 15 ===> Level 16]

Now, time to finally fuck Raine properly.

-----------

Raine's POV

[Short Rest: Healing 1d4 HP and 1d3 MP]
[Rolling]
[Rolled: 4]
[HP Increased: 20/28 HP ===> 24/28 HP]
[Rolling]
[Roll Failed: already at full MP!]

[[Mandrake Drunk] increased in level. Level 5 ===> Level 10]

Raine woke up to the sound of the heavy bedroom door opening. His Mistress walked in and her eyes flashed green. The spiral on the mirror disappeared, letting Raine catch his reflection - strangely his irises now seemed a shade of pink, rather than the greyish-green colour they had been before. Was this a side effect of his hypnosis? Then, the mirror floated away, returning to its place on the wall, leaving Raine unable to judge his reflection any further.

[24 hours past since last receiving or performing oral sex! Side effects will be applied shortly]

[24 hours past since last coming into contact with other sapients' semen! Side effects will be applied shortly]

"Oh, did I return to my Little Raine at the exact right time?" Mistress Tazamoth asked smugly.

"I- yes. Yes Mistress." Raine said, still a bit dazed from the hypnotism.

"Well I do enjoy watching my little femboy fuckmeat squirm. Let's hope you roll low..." She said seductively.

[Subject deemed inactive. Beginning Application of Side Effects.]

[[Sexual Frustration] increased in level. Level 23 ===> Level 25].
[Rolling Random Side Effects (Oral Addiction)(1d20)]
[Rolling]
[Rolled: 18]
[[Sexual Frustration] increased in level. Level 25 ===> Level 28]

'Damn it' Raine thought.

[[Sexual Frustration] increased in level. Level 28 ===> Level 30].
[Rolling Random Side Effects (Semen Addiction)(1d20)]
[Rolling]
[Rolled: 7]
[[Sexual Frustration] increased in level. Level 30 ===> Level 41]
[[Semen Addiction] increased in level. Level 5 ===> Level 16]
[[Body Sensitivity] increased in level. Level 39 ===> Level 45]
[[Aphrodisiac Affected](Permanent)] increased in level. Level 7 ===> Level 11. Cumulative Level: 43]

Raine shuddered as a wave of pleasure rolled over him. Now even the slightest of sensations from the ropes around his wrists and ankles made him flush with heat. He felt utterly desperate, he needed to cum.

"My, my... Did my little Raine roll poorly on one of them? I felt your arousal spike through our bond little slut..." Mistress Tazamoth said, now stood beside the bed. Raine's nose was hit with the scent of alcohol. His Mistress was drunk.

"Yes Mistress, I rolled a 7. But on the other one I rolled an 18" He said, upset colouring his voice.

"Now now my Little Raine. Why don't we cheer you up by shrinking that cage of yours. I've got a 2-incher that'd look soooo cute on you. Much better than the 2 and half inch one at least." His Mistress offered, already pulling a similar looking solid blacksteel cage and the key from her inventory.

"Yes please Mistress." Raine begged.

She climbed onto the bed and began unlocking Raine's cock. Soon, the lock came off with the key, and then his Mistress pulled off the cage proper, revealing Raine's little penis. It was soaked in precum and flopped helplessly to the side. Something about that filled Raine with pride.

"Obviously I'm doing this while you're still tied up so you don't get the chance to touch your uncaged little man-dick. Good boys don't touch themselves there."

"Of course Mistress, I want to be a good boy. I need to be a good boy, please make me a good boy!" Raine begged desperately.

"Oh wow, Hypnotism has taught you well, Raine. We'll definitely have to subject you to some again. I might have to learn some hypnosis to cast on you myself. Fuck that was hot." She said.

Her hands guided the new, smaller cage over his cock and then into place around the ring. The key slid back in, locking the cage shut once more. The pressure was stronger, almost painful. This was good, this was progress. Raine needed to progress.

[[Cursed Blacksteel Chastity Cage] Equipped!]
[[Feminisation]: Secret Condition Met: Downsized Chastity Cage: +0.5% Feminisation]

"Don't worry Raine, all the curses on this one are the same as the previous one." Mistress Tazamoth said, "Why don't you tell me what you learned from your hypno session?"

"Elves are for sex!" Raine exclaimed, proudly.

His Mistress laughed, "Good boy Raine. You are for sex, especially since humans are also for sex. Now, let me untie you."

Raine felt each of the ropes around his wrists and ankles come loose, falling off him as his Mistress untied each one. She then stripped, pulling off the shorts that had barely concealed her gigantic erection, and taking her top off to unveil her tits. Her eyes flashed green and Raine recognised a flask of lube that had been summoned to her hand.

"Now then Raine, on all fours and take out your plug. Your Mistress is going to break you in." She said, a sadistic hunger in her voice.

"What do you mean Mistress?"

"Raine you stupid slut, I'm going to fuck you in the ass." She answered, pouring a generous amount of lube onto her shaft.

"I'm done training for it?" He asked her.

"No, your anal training's only just beginning." She answered.

She got onto the bed, kneeling behind Raine. He felt a meaty slap against his ass, as his Mistress rutted against him, spreading lube all across his ass. She pulled back, and Raine felt her cock at his entrance, he really wasn't sure it'd even fit. His asshole refused to let her dick just slip in, despite his Mistress trying to guide the head in with one hand. Frustrated, she pressed it up at his entrance, the head just barely beginning to enter. Raine felt his cock squirt out some precum in its new cage in response to the anal teasing. His Mistress's cock slipped in a little further, making it just half-way up the head. She snarled, evidently fed up, grabbed Raine's hips with both hands and then rammed forward, pulling his waist back equally as fast. Raine felt an electrifying pain as his Mistress's cock buried itself in his ass almost entirely. Raine let out a girly scream, as his Mistress let out a grunt of victory. Tears welled up in Raine's eyes - it felt so good.

[[Pain into Pleasure] increased in level. Level 18 ===> Level 19]

[You lost your anal virginity. +1% Feminisation]

"O-Oh fuck!" Raine cried out.

"Yeah, you fucking like that you whore?" His Mistress said, pulling back halfway and thrusting into him again

"Ahhgn. I- Yeah, oh! fuck..." Raine responded.

Mistress Tazamoth slapped his ass hard. A wave of pleasure emanated from his right ass cheek chasing the pain.

"I didn't hear a Mistress in that, Raine!" She shouted at him.

"I- Sorry M-Mistress. Ah! Ooh... fuck!" Raine managed out between moans and lustful curses.

His Mistress slapped his ass again, hitting the same spot, causing another wave of pleasure to cross his body. His ass was left red, a dull pleasure and pain emanating from it.

[[Pain into Pleasure] increased in level. Level 19 ===> Level 20]

His Mistress's grasp on his hips tightened to a painful level. Clearly she was barely holding back her strength. Raine felt enamoured by the passion of her rough fucking of his asshole. His arms shook, the pleasure so intense that he was struggling to keep himself up. His Mistress's amazing fat cock plumbed his depths, it kind of hurt but at the same time it was so pleasurable that Raine began to lose his mind with lust.

"Ah, ah... Mistress, I'm ahhn gonna cum!" He screamed.

"Yeah, cum for me Raine, cum from anal like the little femboy bitch you are."

His precum-smeared cage soon spurted out small ropes of hot semen, the cum landing on the bed beneath him.

[A Succubus has brought you to orgasm! Body Sensitivity increased in level. Level 45 ===> Level 46]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 3 ===> Level 4]
[[Anal Sensitivity] increased in level. Level 5 ===> Level 6]
[[Sexual Frustration] decreased in level. Level 41 ===> Level 40]

Raine literally couldn't hold himself up anymore, the femboy's weak arms fell from under him and his face hit the bed. His Mistress didn't let up however, and continued fucking his ass hard. Raine let out a moan as his ass took the abuse. Not content to let her Half-Elf melt from the pleasure however, his Mistress grabbed his shoulder, righting him, pulling him up so he now knelt. Her arm slid around his neck, transitioning to a tight headlock. She pulled him against her chest as she kept fucking him.

"Yeah, take my thick cock you failed male..." She whispered harshly in his ear.

"Mistress!" Raine cried out, already feeling like he was going to cum again

"Mmm... Raine your ass is so tight." she said.

Raine suddenly felt her teeth sink into his shoulder. He gasped out in pain. Soon however, that pain was followed by waves of sharp pleasure that assaulted his senses and left him feeling utterly confused.

[You Mistress, Tazamoth, has used [Foolish Bite] against you!]
[Hit]
[You took 1d8 Piercing damage]
[Rolling]
[Rolled: 4]
[You lost 4 HP!]
[HP Decreased: 24/28 HP ===> 20/28 HP]

[Beginning Hard Wisdom Save with Sextuple Disadvantage (Hypnotised (2), Sexual Frustration, Mandrake Drunk, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling: 7, 10, 15, 4, 9, 18, 3]
[Hard Wisdom Save Failed!]
[You have gained 2 levels of [Body Sensitivity](Permanent)!]
[[Body Sensitivity] increased in level. Level 46 ===> Level 48]
[[Erectile Dysfunction] increased in level. Level 3 ===> Level 4]

"Fuck yeah, take my markings Raine." His Mistress said, snapping him out of his daze.

"Oooh fuck! I'm gonna cum again! Mistress, p-please fuck me-ee! harder!" he cried out.

His Mistress's thrusts sped up to a ridiculous speed. Raine felt a dam inside him break and soon, more cum lazily spurted out of him, this time being shot a little further than before because of his new position stretched against his Mistress's chest. His arms flailed uselessly before eventually grabbing on to the arm his Mistress had wrapped around his neck.

[A Succubus has brought you to orgasm! Body Sensitivity increased in level. Level 48 ===> Level 49]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 4 ===> Level 5]
[[Anal Sensitivity] increased in level. Level 6 ===> Level 7]
[[Sexual Frustration] decreased in level. Level 40 ===> Level 39]

The entwined pair toppled forward, his Mistress landing on top of him, still embracing him tightly. Now, her legs pinned his down, preventing him from even moving slightly as she pounded his ass hard and fast. Raine let out muffled moans, silenced by his mistress's hand, which had moved from her death-grip on his hip to cover his mouth, now that his waist was stuck between her massive cock and powerful hips and the bed. His Mistress's long tongue stuck out, licking his face hungrily. Raine felt himself get coated in his Mistress's thick and slimy saliva. He hadn't realised just how long Mistress Tazamoth's tongue really was though as he felt it creep down and circle around his neck, making it almost around it twice. The speed of his ass fucking only continued to increase, reaching levels that were unbearably pleasurable. Raine felt his mind really go blank. All he could think about was the pleasure, the pain and the fact that as a half-elf, his purpose was sex. Soon though, a familiar hotness ran through his body and he felt himself nearing orgasm for a third time. 

"Fuck Raine, you're so tight, I'm gonna cum in your ass right now!" His Mistress growled

"Ah! M-Me too M-m-mistress! Oh! Oh fuck!" Raine responded.

Raine felt his Mistress shove her shaft in all the way, straining to get even a single millimetre deeper in Raine's virginal hole. Raine felt a huge load of demonic cum wash into his innards, and he suddenly felt very full. At the same time, he felt himself cum, his back arching, driving him further onto his Mistress's cock. A small bit of cum slowly dribbled out of his cock and onto the bed, his balls beginning to run out of the functionless liquid now.

[A Succubus has brought you to orgasm! Body Sensitivity increased in level. Level 49 ===> Level 50]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 5 ===> Level 6]
[[Anal Sensitivity] increased in level. Level 7 ===> Level 8]
[[Sexual Frustration] decreased in level. Level 39 ===> Level 38]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon! +1 XP, +0.5% Feminisation]

Raine felt so tired. He shuddered in post-orgasmic bliss and couldn't even move. Demoness cum started leaking from his ass, pouring down him and dripping off his balls. He felt his Mistress put his plug back in, trapping what was left back inside him. She pulled the bed cover over him, and then pulled him into a hug.

"Good boy, Raine." She whispered to him

Then he was out like a light.

-----------

Changes this chapter:

[Special Trait Increased: Feminisation: 5.3% ===> 10.3%]

[Special Trait Increased: Succubus Covenant Crest: Level 3 ===> Level 6]

[Permanent Effect Increased: Body Sensitivity: Level 37 ===> Level 50]

[Permanent Effect Increased: Pain into Pleasure: Level 18 ===> Level 20]

[Permanent Effect Increased: Semen Addiction: Level 4 ===> Level 16]

[Permanent Effect Increased: Aphrodisiac Affected: Level 7 ===> Level 10]

[Permanent Effect Increased: Anal Sensitivity: Level 4 ===> Level 8]

[Effect Evolved: Entranced (Level 41) ===> Hypnotised (Level 28)]

[Effect Gained: Mandrake Drunk: Level 10]

[Effect Increased: Sexual Frustration: Level 24 ===> Level 38]

[Effect Increased: Erectile Dysfunction: Level 3 ===> Level 4]

[Effect Decreased: Mandrake Hangover: Level 3 ===> Level 2]

Chapter Text

8 Days since Covenant Formed:

-----------

Raine's POV

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 5]
[HP Increased: 20/28 HP ===> 25/28 HP]
[Rolling]
[Roll Failed: Already at full MP]

[Special Trait Progress Increased: Feminisation: 10.3% ===> 10.4%]

[Permanent Effect Increased: Body Sensitivity: Level 50 ===> Level 51]

[Permanent Effect Increased: Anal Sensitivity: Level 8 ===> Level 9]

[Effect Decreased: Mandrake Hangover: Level 2 ===> Level 1]

[Effect Decreased: Heightened Submission: Level 10 ===> Level 9]

[Effect Decreased: Erectile Dysfunction: Level 4 ===> Level 3]

[A new week dawns in your new life!]

[Effect Increased: Aphrodisiac Affected: Level 32 ===> Level 33]

[Effect Converted: 20 levels of [Aphrodisiac Affected](temporary) ===> 1 Level of [Aphrodisiac Affected](Permanent)]

[Effect Decreased: Aphrodisiac Affected: Level 33 ===> Level 13]

[Permanent Effect Increased: Aphrodisiac Affected: Level 10 ===> Level 11. Cumulative level: 24]

Raine woke up once more, having fallen asleep quickly after the brutal fucking his Mistress gave him last night. He felt himself blush as he recalled their actions. She was still asleep it seemed, probably sleeping off whatever alcohol she'd drank. Raine tried not to disturb his Mistress, instead choosing to go through his notifications. It looked like he'd hit the cap for how far the [Weak Lust Curse] on his chastity cage could increase his [Body Sensitivity]. He hoped that his next cage had stronger curses on it - he really liked how now even a small bit of skin on skin contact made him start to feel aroused. It felt right to be that sensitive, natural even.

He hoped he got to experience more hypnotism today, yesterday's session had made the day go so fast and levelled him up really quickly. He glanced back over at the mirror, wishing that the spiral on it would return, even though he knew it wouldn't without his Mistress's intervention. That reminded him, yesterday after his hypnotism, he caught his reflection in the deactivated mirror and his irises looked slightly pink instead of their usual greenish-grey. He decided he had to check if that was still the case. Silently he crept out of bed, trying not to wake his Mistress. He stalked over to the mirror, cringing slightly as one of the floorboards squeaked as his latex-clad foot stepped on it. His Mistress still seemed to be asleep though, so he carried on. Reaching the mirror he stared at his reflection. Sure enough, his eyes had changed from a muted green to a slightly pink colour which reminded him of dilute Rose Water. 

-----------

Tazamoth's POV

[Long Rest: Healing 7d8 HP and 7d6 MP]
[Rolling]
[Roll Failed: Already at full HP]
[Rolling]
[Rolled: 4, 4, 5, 2, 1, 3, 5]
[MP increased: 105/126 MP ===> 126/126 MP]

[Effect Converted: 16 Levels of [Drunk] ===> 6 Levels of [Hangover]]

[Effect Lost: Drunk]

[Effect Gained: [Hangover]]

'Hells' Tazamoth thought, 'this is a nasty headache.'

She cracked an eye open, only to find no sight of Raine. Worry grasped her, did he not like the sex they'd had last night? Had he run off? She rolled over, only to realise Raine had only gotten out of bed. He stood in front of the mirror and for a second Moth couldn't figure out what he exactly he was doing.

'His eyes!' She realised, 'does he not like that the hypnotism changed his eye colour?'

She sat up, slinking out of bed. She hoped he wasn't upset with her for not warning him about that. She padded over to her Half-Elf, placing a hand on his shoulder. He flinched, not having heard her approach.

"Mistress!" Raine exclaimed

"Sorry, Raine did I scare you?" She asked

"...Yeah" He admitted

"Do... you not like your new eye colour? We can change it back if you want." She ventured cautiously.

"No, I do... It was just a surprise Mistress... That's all. Would you really let me change my eye colour, if I wanted?" Raine said.

"Of course Raine, you're my covenanter and... I l- I care about you. If the pink irises make you unhappy you should be allowed to say so. I want you to be happy with me." Tazamoth confessed.

"Oh. Thank you Mistress. I do really like the new colour though, but... C-could you, in the future, let me know if my body's going to change before it does?" Raine asked.

"Of course Raine, I can do that for my little femboy. How about I go through what I have planned for you in the future?" Tazamoth offered.

"Yes please Mistress."

"So, [Feminisation] is obviously going to run its course on you, I'm sure you already know that's going to shrink your height, and your genitals, whilst also making your hips wider?" She started

"Yes Mistress. I look forward to it." Raine answered

"I'm glad to hear Raine. Now, when [Feminisation] hits 100% and it evolves into [Feminised], you might experience slight breast growth. Nothing too large, but it might be noticeable. I take it you don't want it to go any further than that, Little Raine?" She asked.

Raine paused for a second, obviously picturing himself with small tits.

"That sounds nice Mistress, I bet it'll look good on me. But what do mean go further than that?" He asked her.

"I mean, I could eventually turn you into a girl, if you wanted that Raine..." She said.

"Oh... I-I don't want that M-mistress, sorry..." Raine confessed worriedly.

"That's fine Raine. Don't be sorry for being yourself. I won't do that to you if it's not what you want." Tazamoth consoled him.

"Th-thank you Mistress. I'm really allowed to chose how I look?" Raine said incredulously.

Tazamoth cringed, had he not realised she would let him make his own choices as to his exact appearance?

"Of course Raine, is there something you want to change?" She asked him.

Raine gulped, "I er... I want to crossdress more, Mistress... Like, wear s-slutty dresses and stuff..." Raine said nervously.

"Oh of course Raine! You can do that for sure. I'm certain you'll look amazing in a nice tight dress that's just a touch too short. You'd be the cutest little covenanter in all of Ioketara." She gushed.

Tazamoth could already picture a blushing Raine in a cute little dress. With longer hair, maybe with some ribbons, oh her boy would be so cute and irresistible!

"I- Thanks, Mistress." Raine said.

"Say actually, you're currently about the same size as I was when I left imphood and bought my first clothes. I bet I have an old dress somewhere that'd fit you now." She said, turning to go through her wardrobes on the other side of the room.

After a couple minutes of searching, Tazamoth grinned. Behind some of her current more formal dresses, was an old black dress from a century ago. It'd fit Raine almost perfectly. She turned around, holding up to show to Raine, who looked like Christmas had come early. It was only then that she realised the door was open and Komianchi was stood there, watching the two of them... Had she seen all of that?

"Komianchi?"

"Mistress, can we talk? Myalenphor told me to deliver you a message privately, your ears only..." The smaller Demoness said.

"Uh, sure. Just leave me to get dressed and sort Raine out for a second, if you would." Tazamoth said.

"Of course, Mistress." Komianchi said, leaving the room and closing the door.

That was... Concerning. Tazamoth knew that Komianchi wouldn't ever stoop so low as to deliver a plain old message, and Myalenphor would never trust the wild Demoness with any message that came in and was actually important. Either this message was of such immense importance that Myalenphor felt no choice but to give it to the strongest Demoness within the maid team, or Komianchi was lying and this was something else. Chances were that she'd spend a considerable amount of time on it as well - damn it. She handed the dress to Raine, and quickly slipped on her shorts, top and shoes.

"Put that on Little Raine, I'll be back in a bit. If I take longer than a couple minutes, you can watch the mirror for a bit." She said.

She approached the Mirror and activated it with her mana. She spoke in Enochian to it, "Keep to shorter spells."

With that, she stepped out into the hallway, where Komianchi was pacing nervously. Further down the hall, one of the junior maids, Luwienphil was sweeping stray ash off of the floor that Komianchi must've tracked in. She'd only been back from her latest summoning for a few minutes it seemed, ordinarily Lesser Succubi only did one summoning a weak, but Komianchi had been pushing for Greater Demonhood for some time, so Tazamoth had relented and allowed her a second summoning every week. It was very strange that she'd already have something to discuss.

"I take it you don't want to discuss the matter at hand in the hallway. Shall we have this discussion in the Dining room, since it'll be empty." She said to the antsy demoness.

"Yes Mistress, that'd be preferable." Komianchi said.

The pair walked down the hall and entered the dining room, closing the door behind themselves.

"So, what was this message?" Tazamoth asked.

"Sorry Mistress, forgive me for lying but there was no message." The Lesser Demoness admitted.

"I figured. Myalenphor wouldn't trust you to inform me the sky was blue. What do you really want to talk about Komianchi?" Tazamoth asked.

"Yeah, Myalenphor dislikes me quite a lot. I don't want her to know this because she hates being second fiddle, hence the secrecy, but my most recent summoning was very successful. I levelled up a bit and I'm now only 120 xp from hitting Level 50. I want to inform you that I'll be leaving your service soon Mistress. Thank you for everything, I know I haven't been the most diligent maid unlike Myalenphor, but I've enjoyed working for you Mistress." Komianchi said.

Tazamoth suddenly felt quite bad about being upset about and suspicious with the interruption.

"Komianchi that's amazing news! Congratulations are in order. Please do keep in touch after your ascension, Komianchi. Don't worry about any 'lack of diligence' during your service, I enjoyed having you as part of my maid team." Tazamoth said, genuinely proud of the younger Demoness.

"I- Thank you Mistress. I will keep in touch... To be honest I thought you were sick of my antics like Myalenphor is." Komianchi said.

"You don't need to call me 'Mistress' anymore Komianchi, I'm your peer now, or will be soon enough, not your employer. Just 'Moth is fine, if you'd like to be friends that is." Tazamoth said.

"Okay Moth... Wow that feels weird." Komianchi said, trying out the nickname.

"Honestly, it feels weird for me too, having a nickname. I only got it from a new friend a few days ago..." Tazamoth admitted.

"Since getting Raine you've seemed way more sociable Moth, I don't think you made many new connections before a week or so ago." Komianchi stated.

"Yeah, I have been. I guess I'm finally focusing on things other than business and money." She agreed.

"Sooo... Will I be hearing about you getting a concubine soon?" Komianchi said smugly.

"Seriously, you as well? Is it that obvious?" Moth asked.

"I mean kinda, you were pretty serious about the whole 'Take care of Raine while I'm out' thing. You bought him a bunch of expensive stuff as well. Plus you seem genuinely much happier since getting him as a covenanter. And I saw you talking to Raine about his appearance and stuff, the way you treat him is a lot more befitting of a concubine than a mere covenanter." Komianchi noted.

"Az was right, I'm a social disaster." Tazamoth said defeatedly.

"Sorry. Oh also, since I'm calling you Moth now, you can call me Komi." The red-haired demoness said.

"Thanks, Komi. Still, I ought to congratulate you. I'll go grab a bottle of Bloodwine from the cellar in the kitchen for us to share." Tazamoth said.

"Really? Thanks Moth." Komi responded incredulously.

"Oh, and Komi, with the invasion of Larjenne coming soon, I'll be pushing to reach level 100 myself. When I do become a Lady, I'll be forming my own Parvorder as would be right. It'd be an honour to have you join it as a my first fellow order-sister."

Komianchi was stunned, "I would- it'd be an honour, Mi- Moth, to be considered part of your Parvorder. Of course I'd join. To be honest, I didn't think you'd invite someone like me into your Parvorder. I'd have thought Myalenphor would be the first."

"No, I think we're much more alike than you think, it's just as a Greater Demoness, I have an image to maintain to Lesser Demonesses, especially ones in my employ. Since you're about to leave my employ and about to become my peer, it's not like I have to do that anymore. As for Myalenphor, I'm pretty sure she's received an invite to Lady Deminaios's Parvorder, since she's been fucking my business partner in the bathroom every single time I've hosted a dinner for the past year. She might be the head maid, but it's still my house and I do, in fact, know what happens in it. To be fair I think they're a good match, and watching her try not to squirm whenever I mention Lady Deminaios will be visiting is funny, so I'm not mad about it. Anyway, I'd best quit monologuing and get us some bloodwine, else you'll forever be sober." Moth said, before going through the door into the kitchen.

-----------

Raine's POV

Raine spent a minute struggling to get the dress on. He'd never put one on before, even though he'd wanted to before becoming Mistress's fucktoy. Another example of the Academy's draconian rules for its students - no crossdressing allowed. Still, eventually, he got the skin tight sleeveless dress on. It wasn't a terrible fit, the dress hugged his ass and waist nicely, reaching about 1/3rd the way down his thigh, ending an inch or two short of where his latex thigh highs began. No, the problem was with the front of the dress. Firstly it had not been designed with penises in mind - Raine's cage pressed against the front of the dress, leaving an extremely lewd bulge that wasn't subtle at all. That at least was kind of hot though, the second issue was that the dress had definitely been designed with tits in mind, as their was considerable space for cleavage that Raine simply didn't possess. Evidently his Mistress had had massive tits even from the start. Still, the dress did more or less fit, leaving Raine with only one thing on his mind - the Mirror.

[[Tight Black Dress] Equipped. +5% arousal (Feminisation)]

Raine felt his lust increase slightly. A small dribble of precum left his cock, sticking to the front of his dress, leaving it wet and sticky. He walked over to the mirror, and the spiral sprung to life.

[Unrestricted Hypnotic Link Formed between [Ioketaran Hypnotic Broadcast] and your Mind!]

[Beginning Impossible Wisdom Save with Sextuple Disadvantage (Hypnotised (2), Sexual Frustration, Mandrake Drunk, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: >20]
[Current Bonus to Wisdom: -1]
[Rolling: 9, 17, 12, 18, 4, 14, 6]
[Impossible Wisdom Save Failed!]

Now familiar with what the spiral felt like, he felt its influence stretch over him, prodding invasively at his mind. He felt something snap mentally as it forced its way back in.

Recognised Returning Subject:

Welcome back, Femboy!

Running Elf Sissy Hypnosis Spell Two

The spiral morphed, revealing a simply huge demoness cock. It hung flaccid, being held back by a ridiculously undersized thong. The Demoness started to get hard, and the tiny thong snapped, falling off and allowing the monstrous cock to rise freely, reaching a length of one foot. The video cut to an elf wearing the same thong. His cock was barely visible beneath the thong. He got hard, tenting the thong slightly. Words flashed on the screen.

Is that it?

And elves will tell you they're the superior species?

Do you agree with that, sissy?

"No." Raine said, staring hungrily.

Didn't think so...

Good elves are sissies who acknowledge Demoness supremacy.

Good elves are sissies who celebrate Demoness supremacy.

Good elves are sissies who reinforce Demoness supremacy.

You will be a Good Elf...

[[Hypnotised] increased in level. Level 28 ===> Level 29]

"I'm good elf... sissy." Raine muttered, feeling his cock twitch. The image morphed once more, an elf woman appeared, being fucked brutally in the mouth, pussy and ass by a trio of Demonesses. The sounds of her muffled lust-addled moans entered Raine's ears. She was absolutely coated in cum, the thick Demoness batter dripped from all three of her holes, even as the Demons pumped more in.

Elf women have already become whores.

Elf women have already become corrupted.

Elf women have already become Demoness fucktoys.

Elf women have already become Demoness breeding stock.

The image morphed to the same elf woman being fucked by a singular demoness, much larger than the previous three. This one must've been a Demoness Lady. Raine watched as she came in the mewling elf woman's abused cunt. Semen flooded out of her vagina after the demoness pulled out. The video cut, showing the same elf now looking visibly pregnant. Then the video cut back to the second video of the elf being brutally fucked by the giant demoness.

You want to be a whore.

You want to be corrupted.

You want to be a Demoness's fucktoy.

You want to be bred by a Demoness.

The spiral returned once more, as words flashed over it.

It's your nature to be these things.

Would you deny your nature?

[[Hypnotised] increased in level. Level 29 ===> Level 30]

Raine felt more precum soak into his dress. He fell to the floor, transitioning to a sitting position. He hadn't even realised he'd still been standing. He felt the need to be his Mistress's whore be reinforced in his mind. The spiral told him it was right, and he agreed. His eyes glazed over, letting the spiral tell him what was right and wrong, what was true and false, what was fun.

It is in elves nature to be used for sex.

Elves are for sex.

Raine giggled at that line again. He needed to be used for sex, and that was okay because elves were meant for relieving Demonesses sexually. It was his calling and purpose.

"Elves are for sex. ehehe-haha-eehehehahe" He giggled madly to himself.

The spiral spoke once more into his mind.

Ask your Mistress to put you in chastity.

Ask your Mistress for a butt plug.

Ask your Mistress to restrain you.

Ask your Mistress to conquer you.

Ask your Mistress to hurt you.

Good boy...

Ask your Mistress to downsize your chastity

Ask your Mistress to increase your plug size.

Ask your Mistress to restrain you even more.

Ask your Mistress to break you.

Ask your Mistress to fix you.

Good boy...

Become addicted to hypnosis.

Become addicted to sex.

Become addicted to anal.

Become addicted to cum.

Become addicted to your Mistress.

Good boy...

Each 'good boy' sent a wave of pleasure crashing over Raine. He could feel himself getting close now. Precum dripped from the hem of his dress onto the floor now and saliva ran out of his mouth and down his chin. There was nothing but the spiral and its undulating pink and purple light.

[[Hypnotised] increased in level. Level 30 ===> Level 31]

You exist to be fucked.

You exist to be tamed.

You exist to be our property.

Repeat, 'I exist to be Demoness Property' 

"I- ah! I e-exist t-to mmm.... Be Demoness p-property..." Raine stuttered out. The pleasure was getting too much.

Repeat, 'I exist to be feminised'

"I exist mmnph... to be feminised." Raine said suppressing a moan.

Repeat, 'Without feminisation I'm a bad boy'

"Wi-without fem... inisation. I'm a bad boy." Raine said, reaching up his dress to touch his cage. He began to rub at the base of his cock, his subconscious desperate to do anything it could to increase the pleasure being felt. He was so very close now.

Good boy.

CUM...

Suddenly, Raine felt electric pleasure run through him, he began mindlessly grinding against the floor. Semen spurted out of his cock, soaking the front of his dress even more. Globs of cum dripped down the front of his dress and onto the floor. He didn't take his eyes off of the spiral. He couldn't, the idea antithetical to his very existence. He let out several girly moans as he came in his Mistress's dress.

[You came in chastity. +0.1% Feminisation]
[You came while being Hypnotised. +0.2% Feminisation]

[[Hypnotised] increased in level. Level 31 ===> Level 32]

[[Sexual Frustration] decreased in level. Level 38 ===> Level 37]

[[Ioketaran Hypnotic Broadcast]'s hypnotism is attempting to apply various additional effects on you!]
[Beginning Very Hard Wisdom Save against [Ioketaran Hypnotic Broadcast] with Sextuple Disadvantage (Hypnotised(2), Sexual Frustration, Mandrake Drunk, Mental Weakness Curse, Keyheld)]
Minimum Saving Roll: 18]
[Current Bonus to Wisdom: -1]
[Rolling: 3, 8, 10, 12, 16, 2!, 9]
[Very Hard Wisdom Critically Failed!]
[Effects of failure doubled!]
[+2% Feminisation]
[[Sexual Frustration] increased in level. Level 37 ===> Level 39]
[[Erectile Dysfunction] increased in level. Level 3 ===> Level 5]

Raine shuddered as he felt the consequences of his failed save take effect. He giggled to himself.

Elf Sissy Hypnotism Spell Two completed

Running status checks...

All appears normal...

Continuing...

Running Elf-Demoness Biology Lesson Spell 1

Raine stared into the spiral as it started up once more. He felt it cradle his mind as he watched it.

In order to properly service your Mistress, you must understand her body. The body of a Demoness, as it is much superior to an elf's, is substantially different to that of an elf's. Firstly, Demonesses are all, to some extent shapeshifters. Most Demonesses may only be able to slightly change physical characteristics such as height, weight, hair colour, skin tone, etc. However, some may have the ability to change these things quite substantially. Almost all Demonesses are futanari, that is to say capable of possessing a penis or a vagina. Some may possess both at the same time or display other variations such as having multiple penises. As your Mistress levels, it is likely that her genitalia will change with her. When undergoing a transformation, it is certain that a Demoness's Genitalia will undergo some changes as well, generally a Demoness's penis will get longer and girthier with each transformation, and her vagina deeper, to help her accommodate her peers cocks. For these reasons, in order to properly satisfy your Mistress's sexual needs you will require a great deal of adaptability.

"Satisfy... Mistress..." Raine drooled.

Additionally, although all Demonesses have breasts, unlike in elven women their purpose is not for the feeding of young, their purpose is only to attract middleplaners. For this reason, most Demonesses do not have the ability to lactate. Some may choose to invest skill points into developing the ability to do so, but it is still not for the purpose of feeding young, but instead further ensnaring middleplaners - Demoness breasts may secrete many different fluids with differing effects that generally help make you obedient covenanters.

Let us now review the differences between the bodies of the different types of common demons. Imps are the larval forms of demons, simple beings of pure emotion. If Demons were butterflies it would not be incorrect to view Imps as caterpillars. Although some cultures may depict imps as simply smaller demons, in truth Imps are more like worms than humanoids. Generally, Imps are hermaphroditic, possessing both male and female genitalia at the same time. Their bodies range from about 1 foot in length to about 5 feet in length, depending on their level, with higher level imps being longer. They posess horns and a circular, jawless mouth with hooked teeth. They are not hostile to any creature other than other imps, which they will attempt to kill or fuck. They possess no eyes but detect the world through mana, and will be drawn to areas of high mana or magical items. Imps form from excess middleplanar emotions or when a high level demoness has sex with a middleplaner. You will almost never encounter one in the middleplane unless it is birthed naturally. About 1% of Demonesses are fertile in Ioketara. If your Mistress is fertile, it is your duty to take her spawn if you are able to. This will be done via the implanting of eggs within you.

[[Hypnotised] increased in level. Level 32 ===> Level 33]

Raine could feel his cage getting slick again. The idea of his Mistress impregnating him was exciting. He felt heat reach his face as he stared at the spiral that held his mind like a vice.

At level 10, an Imp will transform into a Lesser Demoness. Lesser Demonesses are the most elf-like of any demoness. They range in height from about 5 feet tall to about 7 feet tall, generally getting taller as they increase in level, with the average height being about 5'10. You are probably familiar with depictions of Lesser Demonesses as being Elf-like in build and having pointed ears similar to elves, but having red skin, horns and black hair. Whilst it is true that many Lesser Demonesses do have red skin and black hair, only horns are a universal feature across demonesses. Lesser Demonesses have a range of skin colours, many have human or wood elf-like skin colour, whilst many others have skin that is a shade of red, purple, light blue or grey. Lesser Demonesses do not have tails but do have short, vampire like fangs. Lesser Demonesses are generally about 20% stronger than elves or humans of equivalent size, proof of Demoness superiority.

Moving onto the most pertinent part for elves - the genitalia. It is here once again that the supremacy of Demonesses is displayed, The average penis length of a Lesser Demoness is 6.23 inches, compared to the measly human 5.16 inches or the pathetic elven 4.84 inches. In girth too, Lesser Demonesses surpass comparable middleplaners, having an average girth of 4.67 inches, whereas humans have an average girth of 4.59 inches and elves have an average girth of 4.41 inches. This clearly cements Demonesses as more suitable breeders than Elves. Lesser Demonesses, of course, display a great range in penis sizes, with penis size ranging generally between 5.50 inches and 7.25 inches in length and 4.25 and 5.25 inches in girth. For this reason, you may require some anal training before attempting to engage in anal intercourse with a Lesser Demoness.

In terms of female genitalia, Lesser Demonesses more or less match humans and elves.

When it comes to breasts, Lesser Demonesses also beat humans. The average Lesser Demoness cup size is the low end of a D, whereas the average Human Cup size is a B and the average Elf cup size is an A.

[[Hypnotised] increased in level. Level 33 ===> Level 34]

At level 50, a Lesser Demoness will transform into a Greater Demonesses. Greater Demonesses are not too dissimilar to Lesser Demonesses. The primary difference being that Greater Demonesses are larger and more powerful. It is also at Greater Demonhood that more esoteric features may begin to develop - variant fangs being the most common. Greater Demoness range in height from about 6.25 feet and 8 feet tall, with the average height being about 6.5 feet. Greater Demonesses are generally about 50% stronger than elves or humans of equivalent size, not that there are many of such impressive heights.

Genitalia-wise, the trend of Greater Demonesses being larger and more powerful than their lesser counterparts continues. The average penis length of a Greater Demoness is 7.12 inches, with a general range of between 6.25 inches and 8.5 inches. The average penis girth is 5.25 inches, with a general range of between 4.75 inches and 6 inches. Of course, outliers do exist, and more outliers exist within Greater Demonesses than in Lesser Demonesses. It is within the higher levels of Greater Demons that sexual traits such as [Diphallia] and [Hyperspermia] appear which affect calculations of averages. Unlike in Middleplaners, [Diphallia] in Demonesses does not affect the function of either penis, which both work perfectly but are generally towards the lower end of the averages in terms of length and girth. Greater Demonesses also have larger vaginas and wombs than humans and elves, in order to accommodate their peers penises, generally they are between 20 to 30% larger in most dimensions than in Lesser Demonesses, humans and elves. Greater Demonesses have an average cup size at the high end of a D - far greater than any human or elf.

Raine thought about his own Mistress's tits, they were a lot bigger than most other Demonesses he had seen, so perhaps he was wrong in his initial guess that she had E cups and instead she might have F cups? He supposed he could always ask her.

Finally, we will move onto Noble Demonesses - specifically Ladies, as by the point of Baronesses, their is so much variation that averages are pretty meaningless. At level 100, Greater Demonesses transform into Lady-Demonesses, this transformation is substantially more dramatic than the transformation from Lesser Demoness to Greater Demoness, and this trend continues as the rank of nobility increases. It is at Noble Demonhood that Demonesses gain a tail, as well as the ability to produce offspring with each other and with Middleplaners. A demoness's tail may have many purposes, most are prehensile, allowing them to be used to carry things. Some develop stingers on their tail, allowing them to be used for the injection of venom - whether that be deadly or aphrodisiac. A few even develop Ovipositors within their tails, allowing them to be used to breed. Within Noble Demonesses, virtually all have at least one rare variation to their body plan, whether that be abnormal teeth, extra horns, modified genitalia or something else entirely. Lady-Demonesses range from about 7.5 feet tall to about 10 feet tall. They are generally about twice as strong as humans or elves of the equivalent height if they actually got that tall. Lady-Demonesses are in all ways superior to any human, elf or other equivalent.

Genitalia-wise, Lady-Demonesses are once more substantially larger than their juniors. The average penis length is 9.34 inches, with a general range between 8 inches and 10.75 inches in length. The average penis girth is 6.41 inches, with a general range between 5.75 inches and 7.50 inches. Outliers are common, and atypical penile traits are abundant, ranging from things like [Cock Nodules] - small pleasure-making bumps on the shaft - to things such as having a 3rd set of genitalia to switch out with their penis and vagina - generally this is an atypical penis. Likewise, their vaginas are generally very long to allow for peer-peer mating, generally being 60-80% larger than humans or elves are. Lady-Demonesses have an average cup size of an F, but by the time they reach level 140 this has usually increased to a G.

[[Hypnotised] increased in level. Level 34 ===> Level 35]

Raine felt himself getting closer to orgasm, images of his Mistress as an even larger Noble Demoness filled his head, taking up more space. His hand reached down to jostle his cage once more. The intense arousal from [Hypnotised] clouded his mind as he struggled to this time lift up his dress. He lay down in front of the mirror to make it easier to play with his dick and balls whilst still watching the spiral.

Elf-Demoness Biology Lesson Spell One completed

Running status checks...

All appears normal...

Continuing...

Running Elf Sissy Hypnosis Spell Three...

Raine watched as the spell started up again, he played with his cage as it started. Yet, before any words could be spoken into his mind, the spiral flickered out.

Spell cancelled by Magic Mirror owner.

Raine turned his head, seeing that the door had opened to reveal his Mistress, who was now fawning over his prone cum-soaked form. She knelt down before him.

"Hells, Raine, you're so cute when you're being [Hypnotised], I'm definitely going to have to learn some Hypnosis now." She said to him.

"Th-thank-ss-s Misshtress" Raine got out, desperate to cum, sat right at the edge of orgasm.

Then his Mistress leaned in further, narrowing the distance between their faces, her tongue came out and unthinkingly, Raine obediently opened his mouth to let it in. It slithered down into his throat as his Mistress's lips met his own.

[Your Mistress, Tazamoth, has used [Succubus Kiss] against you!]
[[Body Sensitivity] increased in level. Level 51 ===> Level 52]

[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 13 ===> Level 16]

Raine came. Cum spurted out of his cage and onto his thighs, which sloughed off and onto the floor, leaving behind glossy trails on his legs. He let out a high-pitched whine.

[A [Succubus] brought you to orgasm! [Body Sensitivity] increased in level. Level 52 ===> Level 53]
[You came in chastity. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 6 ===> Level 7]
[[Sexual Frustration] decreased in level. 39 ===> Level 38]

"Cumming with just a kiss? Wow Raine, you're totally ruined." Mistress Tazamoth whispered.

Raine giggled, he was and he loved it.

-----------

Changes this chapter:

[Special Trait Increased: Feminisation: 10.3% ===> 12.8%]

[Special Trait increased: Succubus Covenant Crest: Level 6 ===> Level 7]

[Permanent Effect Increased: Body Sensitivity: Level 50 ===> Level 53]

[Permanent Effect Increased: Hypnotised: Level 28 ===> Level 35]

[Permanent Effect Increased: Aphrodisiac Affected: Level 10 ===> Level 11.]

[Permanent Effect Increased: Anal Sensitivity: Level 8 ===> Level 9]

[Effect Increased: Erectile Dysfunction: Level 3 ===> Level 5]

[Effect Decreased: Mandrake Hangover: Level 2 ===> Level 1]

[Effect Decreased: Heightened Submission: Level 10 ===> Level 9]

[Effect Decreased: Aphrodisiac Affected: Level 33 ===> Level 16]

Chapter Text

8 Days since Covenant Formed:

-----------

Raine's POV:

As the post-orgasmic bliss began to clear, so too did Raine's mind. The hypnotism had ended, meaning that Raine's brain had full access to its own bandwidth, rather than having his own thoughts shoved aside by the intrusive spiral. Of course, the changes made to his mind were still there, but they were locked in now, allowing Raine to finally think his corrupted thoughts rather than merely being made to think them.

He realised that his Mistress had picked him up now, and was taking him to her bed. He decided to check up on his [Feminisation] progress, as he hadn't in quite some time.

[Feminisation Progress: 12.8%

Effects of Progress:

-Skin softness: 112.8%

-Body Hair Growth Rate: 87.2%

-Width of Hips: 12.8mm increase

-Height: 12.8mm decrease

-Penis Length: 6.4% decrease (7.32mm Decrease Hard)

-Penis Girth: 3.2% decrease (2.44mm Decrease Hard)

-Testicle Size: 12.8% decrease [Capped at 90% decrease]

-Sperm Production: 12.8% decrease]

Wow, he'd lost half an inch in height already. Plus, his cock was nearing 1cm shorter than it had been before he was Mistress Tazamoth's property. If he squinted, he could sort of make out how his hips had gotten wider as well. His Mistress placed him down on the bed.

"Now Raine, how do you feel about spending the rest of the day in bed?" She said seductively as she got undressed, revealing her hard cock.

"That sounds amazing Mistress." Raine answered truthfully.

"Good, of course, since it's only just gotten into the afternoon, I'm sure you know what we'll be doing rather than sleeping." She teased him.

"What'll we be doing Mistress?" Raine asked, shaking in excitement.

"How about I show you instead Raine?"

"Of course Mistress!" Raine said cheerily.

He saw his Mistress summon a bottle of lube from her inventory space as he got under the covers. It seemed like now that his Mistress had broken him in, that she intended to fuck him in the ass often now. Raine licked his lips in anticipation. Mistress Tazamoth got into bed alongside him, having smothered her giant shaft in the shiny fluid. He rolled over, presenting his backside to his Mistress. He felt the large cock press against his ass as his Mistress scooted over closer to him.

[[Heightened Submission] increased in level. Level 9 ===> Level 10]

Her engorged head pressed against his asshole, the wet tip slowly slipping into him. Strong arms reached out, one reaching out to grab his neck, while the other worked around Raine's waist, letting her pull him in closer, slowly sinking him down the length of her impressive cock. Raine let out a sharp gasp which transformed into a faint moan as the cock entered and pushed into him. His ass already felt uncomfortable, and he eagerly awaited the coming pain that would heighten the pleasure of his Mistress's thick member even further. With a strong thrust, his Mistress sank her cock into him, her pelvis smacking into Raine's ass. Raine let out a strained moan as he felt his ass fill with her dick. He then felt a firm slap on his ass, his mistress having taken her hand off his waist.

"Good boy Raine..." His Mistress said

He whined as she slowly worked her cock in and out, stretching him out as she did so. As pain began to roll in so too did pleasure, Raine's sore ass making him flush in arousal. He let out a little moan as he lay on his side.

"You're taking your Mistress's cock so well Raine."

Raine let out another moan in response.

"That's it baby, let Mistress slowly pleasure you."

"Ahh. Mistress..." Raine moaned out.

"Shhhh shh shh shhhhh... Just let Mistress work you." She shushed him, whispering into his ear.

He could feel his ass's protestations against her immense girth, followed by his pain-addicted brain's conversion of those feelings into sexual gratification.

[[Pain into Pleasure] increased in level. Level 20 ===> Level 21]

Precum dripped out of his cage and onto the bed. He could feel the sheets behind him getting soaked with lube and his Mistress's own precum as well. 

"Mmm... Your ass is so tight Little Raine... It feels heavenly on my dick..." His Mistress said, starting to breathe heavily.

"Ahh! Thank you. Mnph! Mistress..." Raine said between moans.

"Let's increase the speed Little Raine, I'm eager to reward you with my demonic jizz, and I'm sure you're eager to receive it. I'm not going to stop until we've levelled you up Raine."

Raine felt himself turn red at the idea, the thought of being fucked until he levelled up was definitely arousing when he was only at 20/100 XP required for level up. A sliver of doubt about his own ability to withstand 8 sessions of anal sex with his Mistress did creep into his mind, but he dismissed it - Mistress would ensure she came in him 8 times if that was really what she wanted. He'd probably cum a lot more than 8 times though, if his performance last night and his current feelings of intense pleasure were anything to go by. He let out another girlish moan as he felt Mistress increase her speed.

His Mistress kept thrusting into his sore ass, absolutely pounding his behind. Soon, he felt himself cumming, sticky fluid shooting onto the quilt as he moaned loudly.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 53 ===> Level 54]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 7 ===> Level 8]
[[Anal Sensitivity] increased in level. Level 9 ===> Level 10]
[[Sexual Frustration] decreased in level. Level 38 ===> Level 37]

Raine went limp, the pleasure having overwhelmed him. His Mistress carried on ploughing him though, she must've been getting close herself. His Mistress's crotch continued to slap against Raine's ass. Soon, she too was cumming, injecting Raine with her thick and fertile semen. Raine let out more moans as his Mistress unloaded in him. She growled victoriously as she continued to pump cum into Raine, her heavy nuts slapping against Raine's asscheeks.

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

Raine could feel the demoness's potent cum leak out of his ass even as his Mistress's cock remained within him. She briefly paused thrusting, letting out a contented sigh before continuing on. Raine squealed as his Mistress returned to fucking his ass. The pleasure started to drive him crazy, and remembering what the spiral said about boys thinking, he sank into the pleasure, focusing on nothing else. He paid attention only to smacking together of his and his Mistress's hips, and her sultry whispers of praise. He found himself cumming again and again, bringing his beloved mistress to orgasm a couple times as well. Notifications flickered across his mind. 

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 54 ===> Level 55]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 8 ===> Level 9]
[[Anal Sensitivity] increased in level. Level 10 ===> Level 11]
[[Sexual Frustration] decreased in level. Level 37 ===> Level 36]

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 55 ===> Level 56]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 9 ===> Level 10]
[[Anal Sensitivity] increased in level. Level 11 ===> Level 12]
[[Sexual Frustration] decreased in level. Level 36 ===> Level 35]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 56 ===> Level 57]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 10 ===> Level 11]
[[Anal Sensitivity] increased in level. Level 12 ===> Level 13]
[[Sexual Frustration] decreased in level. Level 35 ===> Level 34]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 57 ===> Level 58]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 11 ===> Level 12]
[[Anal Sensitivity] increased in level. Level 13 ===> Level 14]
[[Sexual Frustration] decreased in level. Level 34 ===> Level 33]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 58 ===> Level 59]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 12 ===> Level 13]
[[Anal Sensitivity] increased in level. Level 14 ===> Level 15]
[[Sexual Frustration] decreased in level. Level 33 ===> Level 32]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

Each time he came, Raine found the subsequent ejaculation took longer and longer to achieve, and less and less semen came out - clearly he was running out of the stuff. By now his ass was very sore, both the hole itself and his cheeks, which had endured several hours of abuse from a lustful succubus and her bitch-breaking cock. Raine felt his eyes roll up into his head as another orgasm approached. Soon the orgasm hit him and he shuddered and then spasmed, impaled as he was on his Mistress's cock. Yet, nothing joined the by now utterly soaked sheets of the bed. Nothing came out of the cage that had at this point become completely drenched in sex fluids. Still, Raine moaned and pressed his ass against his Mistress's hips, trying to gain even another millimetre of her inside of him.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 59 ===> Level 60]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[Feminisation Curse: Secret Condition Met: Have your first dry orgasm: +0.5% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 13 ===> Level 14]
[[Anal Sensitivity] increased in level. Level 15 ===> Level 16]
[[Sexual Frustration] decreased in level. Level 32 ===> Level 31]

Before he could even comprehend what had happened, his Mistress's frantic pumping stopped and she came in him one last time, emptying her large bollocks inside Raine for an 8th time. She let out a victorious growl once more and finally stopped fucking him.

[You have brought your Mistress to orgasm! +10 XP]
[You've been creampied by a Demon. +1 XP, +0.5% Feminisation]

[You have reached Level 5!]
[You have 5 unassigned skill points]
[You gained 1d3 HP and 1d3 MP]
[Rolling]
[Rolled: 1]
[You gained 1 HP!]
[Rolling]
[Rolled: 3]
[You gained 3 MP!]

Crazy, he'd reached Level 5 in just over a week, such speed and ease was practically unheard of in the Middleplane, yet it didn't seem to be the case for covenanters here in Hell - He'd be back above level 20 in a matter of months if this kept on. His Mistress also said something about accompanying her to the Middleplane now, so perhaps he'd level even quicker? Questions for tomorrow really, he was exhausted, and even his Mistress seemed pretty tired. He rolled over onto his back, absolutely soaked in demon cum. It was probably a bit early to go to sleep, but given the anal pounding he just received, Raine didn't much care if he did fall asleep earlier than normal.

"Good boy Raine, you took me so well... Tomorrow we'll get you cleaned up and have a look at your available skills. With 5 points now you can probably get something pretty nice..." His Mistress said, fatigue creeping into her voice.

"Mmmph... Thank you Mistress."

"Let's go to sleep, we'll have a lot of things to do tomorrow to prepare for your playdate the day after... But first, a good night kiss from Mistress..." She said, sitting up slightly.

She descended on Raine, locking their lips together. As usual, her long slick tongue slithered down his throat, causing him to gag slightly. Her abnormally thick saliva coated the inside of his mouth and dripped down his throat. He felt the heat of the aphrodisiac within it start to affect him.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] has increased in level. Level 60 ===> Level 61]

[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 16 ===> Level 19]

Mistress Tazamoth's tongue withdrew, and Raine settled down, putting his plug back in like a good boy. After a few minutes he felt himself drift off into a deep sleep.

-----------

Changes this Chapter:

[Special Trait Increased: Feminisation: 12.8% ===> 19.9%]

[Special Trait Increased: Succubus Covenant Crest: Level 7 ===> Level 14]

[Permanent Effect Increased: Body Sensitivity: Level 53 ===> Level 61]

[Permanent Effect Increased: Pain into Pleasure: Level 20 ===> Level 21]

[Permanent Effect Increased: Anal Sensitivity: Level 9 ===> Level 16]

[Effect Increased: Aphrodisiac Affected: Level 16 ===> Level 19]

[Effect Increased: Heightened Submission: Level 9 ===> Level 10]

[Effect Decreased: Sexual Frustration: Level 38 ===> Level 31]

Chapter Text

9 Days since Covenant Formed:

-----------

Raine's POV:

[Long Rest: Healing 1d8 HP and 1d6 MP]
[Rolling]
[Rolled: 7]
[HP Increased: 25/29 HP ===> 29/29 HP]
[Rolling]
[Roll Failed: Already at full MP]

[Special Trait Progress Increased: Feminisation: 19.9% ===> 20.0%]

[Feminisation Progress has revealed additional information!]

[Permanent Effect Increased: Body Sensitivity: Level 61 ===> Level 62]

[Permanent Effect Increased: Anal Sensitivity: Level 16 ===> Level 17]

[Effect Decreased: Mandrake Hangover: Level 2 ===> Level 1]

[Effect Decreased: Heightened Submission: Level 10 ===> Level 9]

[Effect Decreased: Erectile Dysfunction: Level 3 ===> Level 2]

[[Mandrake Drunk](Level 10) became [Mandrake Hangover], increasing it to Level 11]

[24 hours past since last receiving or performing oral sex! Side effects will be applied shortly]

Raine groaned as he woke up, his butt was sore, and his body from the neck down was extremely sticky. Last night had been wild, and he could scarcely believe he'd been able to withstand so many rounds of anal sex. Clearly he'd become much more of a slut than he was when he first summoned his Mistress. Then again, he kind of was a slut back then, just a repressed one. He saw that his Feminisation had hit 20% now, and decided to look at its effects so far, especially since he apparently had access to new information.

[Feminisation Progress: 20.0%

Effects of Progress:

-Skin softness: 120.0%

-Body Hair Growth Rate: 80.0%

-Width of Hips: 20mm increase

-Height: 20mm decrease

-Penis Length: 10.0% decrease (11.43mm Decrease Hard)(7.62mm Decrease Soft)

-Penis Girth: 5.0% decrease (3.81mm Decrease Hard)(3.49mm Decrease Soft)

-Testicle Size: 20.0% decrease [Capped at 90% decrease]

-Sperm Production: 20.0% decrease

-Sperm Quality: 20.0% decrease]

Raine appreciated being able to see how much smaller his cock was getting whilst soft - before Mistress Tazamoth started feminising him, he was 3 inches long and 2.75 inches in girth when flaccid, which'd mean by the end of it all he'd be 1.5 inches long and 2.06 inches in girth - which'd mean his cock would be only about two-thirds of an inch wide when he was done, a tantalising prospect. Sperm Quality was a little less straight forward to understand, but Raine soon realised it meant that what sperm he could still produce would be weaker and weaker, fewer and fewer sperm cells being able to even make it to an egg. Of course, as a half-elf it didn't even matter if they did reach it in the first place, but the idea of him being sterilised in another way was erotic.

[Subject deemed inactive. Beginning Application of Side Effects.]

[[Sexual Frustration] increased in level. Level 31 ===> Level 33].
[Rolling Random Side Effects (Oral Addiction)(1d20)]
[Rolling]
[Rolled: 17]
[[Sexual Frustration] increased in level. Level 33 ===> Level 37]

Raine found himself kind of disappointed, he'd gotten off with just a light punishment of a few levels of sexual frustration. He'd have to wait until the evening to get his next side effects, and that was assuming his Mistress didn't make him cum between now and then. Speaking of his Mistress, she was already awake, flipping through a book that Raine couldn't read - he was reminded of his inability to so much as speak Enochian. She turned to look at him.

"Good morning Little Raine." She said giddily.

"Good morning Mistress." Raine replied.

"How about we go over some potential skills we could get you, now that you have 5 unassigned skill points, we can probably get you a pretty powerful skill. At the very least we can look to see if what there is. If there's no 5 point skills there that are worthwhile, we can always get you a few weaker skills to improve you." She explained.

"Of course Mistress."

"How about I read them out to you as I go through them? Would my little Raine like that?" She cooed.

"Yes Mistress." Raine replied eagerly.

-----------

Tazamoth's POV

She brought up Raine's skill shop Menu, and began reading through the listed skills and traits available to her covenanter.

[Unspent Skill Points: 5]
[Available Skills]

[Self-Lubrication - 1 SP]
[Pain addiction - 1 SP]
[Masturbation addiction - 1 SP]
[Body Writing Fetish - 1 SP]
[Latex Fetish - 1 SP]
[Spanking Fetish - 1 SP]
[Very Weak Mana recycling - 2 SP]
[Feminine Beauty - 2 SP]
[Tough Skin - 2 SP]
[Fire Resistance - 3 SP]
[Very Weak Fire Affinity - 3 SP]
[Very Weak Ice Affinity - 3 SP]
[Very Weak Blood Affinity - 3 SP]
[Trojan Mind - 4 SP]
[Novice Heal Slut - 4 SP]
[Psychically Open - 5 SP]
[Very Weak Anal Womb - 5 SP]

She read each of them out to Raine.

"Well, Little Raine, which ones are you interested in?" She asked him.

"Uhm... Honestly, all the sex-related ones... They all sound really hot..." Raine said, blushing with embarassment.

"I agree, your job as a covenanter is sex, affinities and higher defence are secondary." Tazamoth agreed

"Maybe not the Anal Womb though, since I'm not sure how I feel about that, and it wouldn't be useful for you until you're a higher level, Mistress." Raine said.

"Hmm, yes. Something to think about later on then." Tazamoth conceded.

She looked at the new list.

[Self-Lubrication - 1 SP]
[Pain addiction - 1 SP]
[Masturbation addiction - 1 SP]
[Body Writing Fetish - 1 SP]
[Latex Fetish - 1 SP]
[Spanking Fetish - 1 SP]
[Feminine Beauty - 2 SP]
[Trojan Mind - 4 SP]
[Novice Heal Slut - 4 SP]
[Psychically Open - 5 SP]

"Would you like me to start reading out the descriptions of them Raine?" She asked him

"Yes please Mistress." Raine responded in the affirmative.

[Self Lubrication (Trait) - Your anus starts to produce its own lubrication, reducing or eliminating the need for lubricants when having anal sex, improving the experience for the top and requiring less preparation.]

[Pain Addiction (Effect) - You have become addicted to pain and will actively seek out painful sexual experiences. 1% of pain will be converted into pleasure per level, above level 100, pain will be converted into pleasure at a greater than 1:1 ratio, increasing 1% per level. Failure to lose at least 1 HP in 24 hours may have side effects.]

[Masturbation Addiction (Effect) - You have become addicted to Masturbation and will attempt to Masturbate whenever possible. 1 XP will be rewarded if you orgasm from masturbating. Failure to induce orgasm via masturbation for 24 hours may have side effects.]

[Body Writing Fetish (Trait) - You are obsessed with having words written on your skin. +1% arousal for each word written on your skin. +1% body sensitivity for each word written on your skin. Gain disadvantage to wisdom saving throws when words are written on your skin. Certain words may have additional effects on first application. All effects tripled when words are tattooed on your skin. Removal of words will increase the level of [Sexual Frustration] by 1 for each word removed.]

[Latex Fetish (Trait) - You are obsessed with covering your body in Latex. All areas of the body with latex on them will experience +100% Sensitivity. Each piece of Latex clothing worn will increase arousal by 5%.]

[Spanking Fetish (Trait) - You are obsessed with being physically punished. Being hit by a dominant faction member will increase arousal, body sensitivity and (if applicable) fertility by 10% until the next long rest.]

[Feminine Beauty (Trait) - Your facial structure changes every so slightly to make you look more feminine, as do a few other physical features such as your shoulders and buttocks. +5% charisma.]

[Trojan Mind (Skill) - Once every long rest, if you are being hypnotised alongside others who have a positive opinion of you, you may apply all disadvantages you have to them on their saving throws for resisting hypnosis.]

[Novice Heal Slut (Trait) - When you bring a faction member to orgasm, heal them by 1 HP.]

[Psychically Open (Trait) - Receive disadvantage on all wisdom saving throws against hypnosis. All effects applied by Hypnosis doubled.]

"Wow" said Raine, "some of these seem very powerful Mistress."

"Indeed, so what are you interested in getting Raine?" She replied.

"Well... If I'm going to be a proper sissy slut, then I should get [Feminine Beauty], which leaves me with 3 Skill Points left... I should also probably get [Self-Lubrication] to make fucking me easier as well. Then with the last two points, I'm not sure Mistress ,the options all look really good."

"I see... How about [Body Writing Fetish]? I'm curious about what additional effects there might be and I'm sure you are as well, plus I think it'd be really hot to claim you as mine for all the world to see by writing all over you. I know how much you like the side effects of addictions, so how about [Pain Addiction]? You've got to finish having your tattoo done, and that'll make that more enjoyable for you." She proposed.

"[Body Writing Fetish] sounds really hot when you put it like that Mistress. Same with [Pain Addiction], I'd like both of those please. Also, c-can you start writing on me today Mistress?" Raine asked, flustered.

"Of course I can start writing on my Little Raine! You only have to ask, since you're such a good boy." She praised him. "Now, lets get these new traits and effects on you."

-----------

Raine's POV

[Gained Trait: Feminine Beauty]

[Gained Trait: Self-Lubrication]

[Gained Trait: Body Writing Fetish]

[Gained Permanent Effect: Pain Addiction]

Raine felt odd shifts in the bones of his face, as well as his shoulders shrinking ever so slightly, whilst his ass increased in size a bit as well. It was somewhat jarring, it wasn't painful but it was most certainly unnerving. He got out of bed and looked at himself in the mirror. His face did look a bit more feminine - he'd never looked masculine, but now he looked downright girly. His shoulders were a little thinner as well. He turned, and his ass did look a fair bit bigger. On the whole, it looked like he'd gone from the moderate androgyny that most male elves and half-elves possessed to a much more feminine figure - though it was still pretty clearly male. He still looked like himself as well, which was nice.

He also noted that he was still utterly drenched in cum, which had started to dry on him now. As much as he loved his Mistress and her semen, it was a little grim being half-soaked in congealing and in places, drying cum. His Mistress too, was soaked, she had gotten out of bed too. He stared at her mighty figure.

[[Heightened Submission] increased in level. Level 9 ===> Level 10]

"I think, Raine, that we need to bathe." She said.

She walked towards the door, running a finger over his ear as she passed him. She opened it, and walked out into the hallway, with Raine following behind obediently. Soon, the two were in the bathroom, and Raine was pulled into the warm water by his Mistress. He let out a little gasp at the casual use of his Mistress's strength. The cum soon started to slough off of him, the more stubborn bits he washed off with a generous amount of soap.

"I was thinking Raine, that since you enjoyed crossdressing yesterday so much, that we ought to go into Gomhisseg today and buy you your own dress, one that fits you properly, for your playdate tomorrow, and maybe get you some equipment for when you accompany me into the Middleplane, whenever that is. Whilst we're going there I can teach you more about Ioketara and you can tell me more about your life before you became mine if you'd like." Mistress Tazamoth said.

"Thank you Mistress! O-of course I can tell y-you more about my time a-at the academy." Raine said, stuttering slightly with excitement.

"Now then Raine, lets finish getting cleaned up, and then we'll start getting you ready for a day out shall we?" His Mistress said.

A little bit of scrubbing later, and then him and his Mistress were drying themselves on towels and heading back to Mistress's bedroom. Once dry, the two sat down on a section of the bed that wasn't smeared with love juices.

"I was thinking Raine, since we want your little cock breaking and your body feminising as soon as possible, why don't we downsize your cage again? Since you can take Mistress's cock as well now, we could upsize your plug as well."

"R-really Mistress? W-we could d-do that?" Raine asked excitedly

"Of course Raine. I have a 1.25 inch cage ready that I think we could just about squeeze you into! And the next plug is really quite large. The curses are both the same, though eventually we'll get to a cage with much stronger curses. I think you'll enjoy that one..." She said seductively, a predatory smile crossing her lips.

Raine gulped, 1.25 inches was tiny. He wasn't even sure he'd fit. Maybe his Mistress would actually break his cock just trying to get it in. Raine felt precum drip out of his cage at the thought of such a thing. His Mistress's eyes flashed green and soon, a smaller cage, a leather strap and a large plug appeared in her hands. The plug must've been 3 inches long and 1.25 inches wide. She placed them on the side of the bed, and summoned the key for his cage as well. She placed it in the lock, turning it and pulling out the locking mechanism. The cage came off, leaving behind only the ring that it mounted too. She ran the leather strap - which Raine now noticed had snap fasteners on it - through the ring at the base of his cock, securing it with the snap fasteners before running it around him and fastening it to the opposite side of the ring as well. Raine only now realised how much more comfortable this was, and let out an appreciative gasp, his flaccid cock twitching slightly.

"Oh, did my little toy like that?" His Mistress asked.

"Y-yes Mistress" Raine answered.

"Then you'll love this." She said, grabbing the tiny cage, like the others before it it was one solid piece of metal with only a small hole in the end to let out precum and semen.

She pressed it onto Raine's cock, slowly pushing it back towards the ring. Pressure started increasing, and Raine let out a little moan - with how sensitive his body was becoming, the pressure alone was arousing. With a slight click, the cage met the ring, putting Raine's poor cock under immense pressure. It felt as though it was being pushed inside him. Then his Mistress locked it, and withdrew, leaving him a blushing mess.

[[Cursed Blacksteel Chastity Cage] Equipped!]
[[Feminisation]: Secret Condition Met: Downsized Chastity Cage: +0.5% Feminisation]

"Let's get that Plug changed shall we?" She said.

Raine rolled over, presenting his ass to his Mistress. She grabbed the base of his plug and pulled it out slowly, Raine's asshole reluctantly sliding off of the metal toy. She picked up the larger one from her bed. Raine's ass started dripping from arousal, his new [Self-Lubrication] trait coming into effect. Methodically, his Mistress teased his asshole, slowly introducing the tip of the long and thick plug to his entrance. Raine let out a whorish moan as it entered, precum drooling from his tightly caged cock as it slid in. Then, all of a sudden, his asshole closed around the end of the plug's head, leaving only the flared base out of his innards. 

[[Cursed Blacksteel Butt Plug] Equipped!]
[[Cursed Blacksteel Butt Plug] Primary Curse Activated: Increasing Sensitivity Curse!]
[[Cursed Blacksteel Butt Plug] Secondary Curse Activated: Very Weak Arousal Curse!]
[[Cursed Blacksteel Butt Plug] Tertiary Curse Activated: Feminising Curse!]
[[Feminisation Curse] Secret Condition Met: Increase the size of your butt plug: +0.1% [Feminisation] Progress]

Raine let out another high-pitched moan as his Mistress withdrew and he sat up. Now, it was impossible to even move without bringing himself pleasure. He was beginning to thing that he might actually cum on the way to Gomhisseg. His Mistress disappeared the old cage and plug in a flash of green. When the flash ended, Raine saw that she held a strange metal pen in her hands. He cast her a confused glance.

"Well, I figured we'd get started with writing on you right now, and through that, start teaching you some words in Enochian. I'm going to write in eyeliner, since it's waterproof. Wouldn't want a little water to remove all my marks on my favourite fucktoy now?" She explained

"O-oh, of course Mistress."

"Now stand up and hold still Raine." She ordered him.

Raine complied, stood stock still, unable to even think of moving. His Mistress soon began painting letters onto his crotch, just below his crest tattoo, followed up by an arrow pointing to his cage.

"That, is Enochian for 'Useless'." She said, as Raine stared at the glyphs, memorising them as his face flushed.

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Useless' (cock) - Effect: -5% semen production (permanent), gain 3 levels of [Erectile Dysfunction]!]
[[Erectile Dysfunction] increased in level. Level 2 ===> Level 5.]

"Oh wow, that is a strong effect! We'll have to write a lot more on you Raine." Mistress Tazamoth said gleefully.

She moved up to his stomach and began writing on him once again, this time the black lettering obviously formed two words, one atop the other.

"This is Enochian for 'Demoness Fuckmeat', let me teach you how to pronounce it Raine." His Mistress said as he flushed bright red.

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Fuckmeat' - Effect: gain 2 levels of [Body Sensitivity]!]
[[Body Sensitivity] increased in level. Level 62 ===> Level 64.]

Raine felt himself begin to sweat. The concept of being merely a living fucktoy for Demonesses was incredibly hot and had him thinking back to the times his Mistress had railed him. The writing continued on his stomach.

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Hit me' - Effect: gain 2 levels of [Pain into Pleasure]!]
[[Pain into Pleasure] increased in level. Level 21 ===> Level 23]

She then transitioned into writing on his thighs, writing on his left, and then his right.

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Demoness Only' - Effect: gain 3 levels of [Aphrodisiac Affected](permanent), gain 1 level of [Body Sensitivity]]
[[Aphrodisiac Affected](permanent) increased in level. Level 11 ===> Level 14]
[[Body Sensitivity] increased in level. Level 64 ===> Level 65.]

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Conquered' - Effect: gain 2 levels of [Submissive]!]
[Permanent Effect Gained: Submissive]

[Submissive - You naturally desire to serve those that are stronger than you. Disadvantage on all saving throws against faction members of a higher level. +1% arousal per level if you are owned by another being.]

Raine read the new effect's description with glee. He felt the need to serve and please his Mistress increase even higher - he felt more devoted to her than he ever had to any deity. His Mistress moved back up and started writing across his chest.

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Failed Male' - Effect: gain 3 levels of [Erectile Dysfunction]]
[[Erectile Dysfunction](permanent) increased in level. Level 5 ===> Level 8]

[[Body Writing Fetish] Activated]
[No special phrase detected!]

Raine soon found a pentacle had been drawn around his left nipple, whilst 'Failed Male' had been written across his chest. He felt his cage leak at the description, he really was a 'failed male'. His Mistress turned him around, writing on his back now. He could make out an two words being written, followed by another arrow pointing towards his asshole. 

[[Body Writing Fetish] Activated]
[Secret phrase unlocked! 'Cum here' (ass) - Effect: gain 2 levels of [Anal Sensitivity]]
[[Anal Sensitivity] increased in level. Level 17 ===> Level 19]

"I think that'll do for now Raine, now turn around and give your Mistress a kiss." Mistress Tazamoth said.

Raine obliged, turning around and opening his mouth as his Mistress bent down and plunged her tongue into his mouth, her lips closing against his. Raine's eyes watered slightly at the invasive tongue's probing of his throat.

[Your Mistress, Tazamoth, used [Succubus Kiss] against you!]
[[Body Sensitivity] has increased in level. Level 65 ===> Level 66]

[Ingested Aphrodisiac Fluids (Saliva). [Aphrodisiac Affected] increased in level. Level 19 ===> Level 22. Cumulative Level: 36]

Raine felt her tongue retract back into her own mouth and their lips soon parted. Yet she didn't bend back up, instead, she spoke.

"Hmm... perhaps one more mark on my little Raine for today" she said contemplatively.

She bent even lower, delivering a painful bite to Raine's left shoulder.

[Your Mistress, Tazamoth, used [Foolish Bite] against you!]
[Hit]
[You took 1d8 Piercing damage]
[Rolling]
[Rolled: 3]
[You lost 3 HP!]
[HP Decreased: 29/29 HP ===> 26/29 HP]

[Beginning Hard Wisdom Save with Sextuple Disadvantage (Hypnotised (2), Sexual Frustration, Submissive, Mental Weakness Curse, Keyheld)]
[Minimum Saving Roll: 15]
[Current Bonus to Wisdom: +0]
[Rolling: 3, 1!, 19, 18, 8, 14, 12]
[Hard Wisdom Save Critically Failed!]
[Unable to increase level of [Body Sensitivity] due to reaching cap!]

[You failed a Saving Throw against your Mistress!]
[[Erectile Dysfunction] increased in level. Level 8 ===> Level 9]

[[Pain into Pleasure] increased in level. Level 23 ===> Level 24]

Raine let out a moan as the pleasure from the sharp pain washed over him. He felt his cock twitch slightly within its cramped cage as [Erectile Dysfunction] levelled up, it was looking more and more likely that he was not ever going to be getting an erection again.

"Right then Raine, why don't we go out to Gomhisseg and get you a new dress then?" His Mistress said, getting dressed into her usual shorts, top and boots and walking towards the door.

"Uh... Mistress? What a-am I going to be wearing?"

"Oh my Little Raine, do you not get it? You won't be wearing anything. Afterall, we want to show everyone what a good boy you are. How could they see all the words of praise I wrote on you if you wore anything?" She said seductively.

"O-oh... right. Of c-course Mistress." Raine flushed, remembering the various hungry looks he'd gotten last time he went to Gomhisseg with his Mistress, he could only imagine there being so many more this time.

"Now do come along, Raine. It's a long walk after all and we've got to get you on your leash." His Mistress said, turning around and opening the door, beckoning Raine to follow her.

-----------

Changes this chapter:

[Special Trait Increased: Feminisation: 19.9% ===> 20.6%]

[Trait Gained: Feminine Beauty]

[Trait Gained: Self-Lubrication]

[Trait Gained: Body Writing Fetish]

[Permanent Effect Gained: Submissive: Level 2]

[Permanent Effect Gained: Pain Addiction: Level 1]

[Permanent Effect Increased: Body Sensitivity: Level 61 ===> Level 66]

[Permanent Effect Increased: Aphrodisiac Affected: Level 11 ===> Level 14]

[Permanent Effect Increased: Anal Sensitivity: Level 16 ===> Level 19]

[Effect Increased: Sexual Frustration: Level 31 ===> Level 37]

[Effect Increased: Aphrodisiac Affected: Level 19 ===> Level 22]

[Effect Increased: Mandrake Hangover: Level 2 ===> Level 11]

[Effect Increased: Erectile Dysfunction: Level 3 ===> Level 9]

[Effect Lost: Mandrake Drunk]

Chapter Text

9 Days since Covenant Formed:

-----------

Raine's POV

Raine felt the carabiner of his leash click shut, securing it to his collar. Raine felt trepidation towards the journey ahead - just walking down the corridor to the front door had left him sweating with arousal, the plug stirring his insides while the pressure in his stifled cock frustrated him. His Mistress lead him out of the door and into the wilds of Ioketara. As far as the eye could see, grey ash stretched interspersed by the odd red boulder dotted around the landscape. In the very distance, the city of Gomhisseg loomed. It was a long walk and Raine wasn't sure he'd be able to make it without cumming at least a couple times.

Mistress Tazamoth started walking along, her long legs setting a fast pace, forcing Raine to speedwalk, further agitating him.

"So Raine, tell me more about what your life was like before we met. What age did you start at that academy?" His Mistress prompted.

"Well, to be honest Mistress, I was abandoned there as an infant by my mother. She was a human apparently, meaning my father must've been an elf. Not sure what kind, but he was probably a wood elf, since they're the most common subspecies in Inglia, and I don't have any of the physical traits associated with either sun or moon elves. I'm not sure there are any other kind of elves in Inglia. Not being wanted hurt for a long time. It wasn't until I was 13 that other students my age started being introduced, that's when I met my f-friends." Raine said, expression turning sorrowful as he remembered his friends.

"Oh. I'm sorry Raine... Would you like to talk about your friends? I'm sorry for bringing that up if you aren't ready for it." Mistress Tazamoth asked with concern.

"N-no it's fine. I should... talking about them will help, I think." Raine stuttered out.

"Ok Raine, tell me about them." His Mistress said as she stopped and crouched to look into his eyes.

"Their names were Willow, Heather and Clover. I mentioned Willow before, she was the only other Half-Elf there, and the same age as me roughly. Then Heather and Clover were identical twins. They were some of the only Wood Elves there and were about a year older than me. We were all rejects, since the humans hated us, and the more common 'high' elf subspecies hated us 'low elves' more than they hated each other." Raine said.

"...I'm sorry to hear that, Raine..." Tazamoth said after a pause, seemingly uncertain about what to say, it was odd for Raine to see his normally so confident Mistress seem unsure.

"I... Mistress, can we talk about something else? I-I-I know it'll be good for me to talk about them b-but I'm not sure now is the best t-time for it." Raine said, voice beginning to waver.

"Of course Raine... Do you have any you'd like to ask me?" Mistress Tazamoth prompted him mercifully.

"I... Can I have a minute to think of some, Mistress?" Raine asked, feeling a little brighter now that the topic had changed.

"Of course my Little Raine..." His Mistress answered.

They walked in silence for a minute, broken only by the occasional gasp from Raine as his steps brought him small shocks of pleasure.

"M-mistress?" Raine began

"Yes Raine?" She answered

"Y-you seem very rich compared to other Greater Demonesses. Is that true? How did you get rich if that was the case?" He asked her.

"Yes Raine, I am much more wealthy compared to most Greater Demonesses. See, when I was about level 40, about 15 years ago now, I was lucky enough to be summoned by a Greater Immortal, some human woman who'd recently reached level 200. She'd apparently narrowly defeated a Demon Lord a few days prior but had been afflicted with a powerful lust curse in return. It took her very little convincing to give up her soul to Ioketara, and become a Seedbed for some Demoness Lady. Then I managed to convince most of her female servants to join her in selling their souls by fucking her in front of them. Apparently, she'd demanded chastity of all of them, so seeing me fuck her silly made their repression come to the surface. I got a good commission on that, Ioketara pays 500 Marks for a Greater Immortal's soul. Of course, I then invested that in a couple businesses here to guarantee an income, mostly into Lady Deminaios's Iron Mines. She's one of my business associates, you'll probably meet her soon enough." His Mistress explained as they continued walking.

"Mistress, what is a mark?" Raine asked next.

"Ah, of course, I should explain. The Mark is a coin of Ioketara. It is divided into 256 Pennies, with each penny being just over a gram of silver. I do believe in Inglia, the pennies are about 9/10ths of a gram of silver. There's also Groats, which are 4 pennies, Sixpence which are 6 pennies, and Shillings which are 12 pennies. There's also half-pennies, farthings and half-farthings. Each of those is worth half of the previous coin."

"Oh, thank you for explaining Mistress." Raine said.

In his head he did the maths, in Inglia a labourer would typically earn 1 penny a day, and Journeyman Mages would earn 5 or 6 pence a day, and a Master Mage would earn 10 to 15. His Mistress had earned 500 Marks, which would be 128,000 pennies, except even higher because Inglese pennies were smaller, but even 128,000 Inglese pennies were the equivalent of centuries of manual labour. His head spun at the idea of so much money.

They walked on in silence for a bit, Raine steadily getting more flustered as his Mistress pulled on his leash, and the buttplug stirred in his ass. After perhaps another 10 minutes, Raine began to slow down slightly, his legs quivering as he began to moan from the pleasure. His Mistress yanked on his leash hard, forcing him to stagger towards her, the buttplug making the movement incredibly pleasurable. He whimpered slightly, and he felt himself near orgasm, precum dripping out from his cage, forming a thin line of clear liquid that hung between his legs, occasionally dripping into the ash beneath his feet, where it seeped into the dry ground. His Mistress pulled him again as he slowed once more. This time, the pleasure was too much to bear and Raine began whimpering pathetically as he came. No cum came out, and Raine felt barely able to stand, legs shaking underneath him as the force of the orgasm hit him.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 66 ===> Level 67]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 14 ===> Level 15]
[[Sexual Frustration] decreased in level. Level 37 ===> Level 36]

His Mistress turned around and looked at him as he came. A predatory smile adorned her face as she enjoyed her Half-Elf's effeminate moans and whimpers. As soon as Raine had finished, she carried on walking, barely giving him time to breathe, pulling the femboy behind her as she continued on. 

They carried on in silence for a while, Raine too caught up in his post-orgasmic weariness to formulate any questions. Soon, the city of Gomhisseg drew closer, starting to loom over them. Raine was once more quite aroused, having recovered from his prior orgasm.

"Mistress, you mentioned before that most Demonesses are not born, does that include you?" He asked.

"Yes Raine, I was not born, though it's becoming more common nowadays for Demonesses to be birthed from covenanters." She explained.

Buy now they had reached the open gates of the city, and the pair entered Gomhisseg.

[You have entered an area of concentrated Lust!]
[[Body Sensitivity] increased in Level. Level 67 ===> Level 68]
[[Aphrodisiac Affected](Permanent) increased in Level. Level 14 ===> Level 15]

Raine felt the eyes of several succubi fall upon him as they passed through the gate. A purple succubus licked her lips as her gaze followed his mostly nude form down the street. He could see several other demonesses reading the words scrawled across his body. It felt dangerously exciting to be clad only in latex and his cage, for all the world to see. His cock drooled as they continued into the town. His Mistress led them through the streets towards what looked like a large hall, which must've been the clothes shop. Yet, as they neared the door, another Demoness strode out from it. She was massive, easily 9 feet tall when including her horns. She had deep red skin and crimson hair, and wore only a regal looking cloak, and metal gauntlets and boots. This allowed her to display a frankly intimidating cock - a bit over a foot long and probably about 11 inches in girth or nearly 4 inches in diameter, across its length were a large number of fleshy nodules evidently designed to cause either immense discomfort or immense pleasure in whatever poor soul ended up impaled on the terrifying organ. From behind her swished a large tail, the end of which was tipped with a chitinous blade almost a foot long which dripped a strange red-purple liquid. Evidently, this was no common Demoness.

[You are in the presence of a Strong Being of Lust!]
[[Aphrodisiac Affected](Temporary) increased in level. Level 22 ===> Level 23]
[[Sexual Frustration] increased in level. Level 36 ===> Level 37]

Raine's eyes widened slightly as he felt the sheer weight of being around such a powerful lifeform, previously he had only felt anything like this around the Archmage of Whitcrest academy, and even that hadn't felt so... directed. He looked back up at her, and saw she was holding a leash of her own, and that walking alongside her was a beastfolk woman, judging by the ears and tail - a Catwoman. The woman was obscenely pregnant, her gravid stomach bulging out in a way that seemed biologically impossible. She was also entirely nude, wearing nothing but a vacant smile, a permanent blush and her own vaginal juices, which seemed to constantly stream out down her legs. Her tongue lolled out of her mouth slightly, and her large distended tits settled on her bloated belly. Her irises were pink like Raine's own as well, marking her out as hypnotised - deeply so if the richness of the colour was anything to go by. Her figure was alluring, and Raine could feel his attitude towards being impregnated himself shift from uncertainty to mild curiosity. His Mistress began speaking in Enochian to the Demoness, sounding slightly apologetic. Raine continued to focus on the catgirl across from him, he knew that Beastfolk typically birthed twins, and sometimes even triplets, but she looked as though she were pregnant with octuplets or something. She waved at him, trying to speak to him in Enochian, and then what sounded like Lemnish, the language spoken in the Kingdom of Lemnia, which was not too far from Inglia. After realising Raine spoke neither, she simply went back to smiling at him, this time groping her breasts in one hand while the other rubbed at her pussy. Raine felt himself blush at the obscene act of public masturbation.

-----------

Tazamoth's POV

To say that nearly walking straight into a Noble Demoness was a little mortifying was to put it lightly. Tazamoth began to apologise to the taller Demoness who was at least nominally her superior.

"Oh! Sorry! I didn't see you there!" She began.

"Don't worry about it, it's fine, honest mistakes happen." The Noblewoman said

"Thank you."

"Aww... What a cute covenanter you have! Can I use my skill [Inspection] on him?" The Noblewoman asked her.

"I- Of course! This little one's name is Raine and I've had him for about a week and a half now." Tazamoth explained.

"Oh wow! You've done a good job with him in that time. My name's Lady Philitreshosh by the way, lovely to make your acquaintance. This here is Arla, she's my newest covenanter and I've had her for about 2 months now." She said, holding out her hand for Tazamoth to shake.

"A pleasure to meet you Lady Philitreshosh, My name is Tazamoth." She responded, shaking the outstretched hand.

"Is Raine your first Covenanter? You seem pretty good at training from what my [Inspection] can pick up." The Lady asked.

"Yes, Raine's my first, though to be honest, he was very eager to be trained, more than me being good at training at least." Tazamoth said.

"Well, either way, you're doing a good job with him. Anyway, I've got to go now, I'm running late for an appointment as it is. I hope to see you again Tazamoth." The lady said, tugging the catgirl behind her as she began to walk off.

"Yes, it was nice to meet you as well, My Lady." Tazamoth said, before pulling Raine into the shop with her.

-----------

Changes in this chapter:

[Special Trait Increased: Feminisation: 20.6% ===> 21.3%]

[Special Trait Increased: Succubus Covenant Crest: Level 14 ===> Level 15]

[Permanent Effect Increased: Body Sensitivity: Level 66 ===> Level 68]

[Permanent Effect Increased: Aphrodisiac Affected: Level 14 ===> Level 15]

[Effect Increased: Aphrodisiac Affected: Level 22 ===> Level 23]

Chapter Text

9 Days since Covenant Formed:

-----------

Raine's POV

Raine stumbled into the shop as his Mistress tugged his leash. He tore his eyes away from the beastfolk woman and instead looked around the store. Despite its unassuming exterior appearance, inside it looked quite fancy. Whilst this wasn't some luxury tailors, it also wasn't the average run-of-the-mill store either. Across the open room was a whole host of different clothes on racks, shelves and tables. Most seemed to be of good quality, and Raine's [Dangersense] picked out several cursed pieces in the room, and that most seemed enchanted at least. Throughout the maze of clothing were several uniformed lesser demonesses, who flitted about between rows, adding clothes to shelves or talking to customers. After a short while, one of them came over to His Mistress and began conversing in Enochian.

Raine wasn't sure what they said, but soon the store attendant left them. His Mistress turned to him and spoke.

"We're going to be getting you 3 different dresses to try on Raine, then we'll see which one you like best okay?"

"Okay Mistress, thank you Mistress" Raine said.

The pair stood in silence for a short while before the staff member returned. In her arms were a series of 3 different dresses. All were mostly black, but one appeared accented with whites. It was this one that was handed to him, and Raine soon realised it was some sort of maid dress. He struggled into it, still unfamiliar with putting dresses on. It actually did a pretty good job of covering him, and he looked somewhat professional even, rather than the exhibitionist slut he'd seemed just seconds before.

[Maid Dress Equipped. +5% arousal (Feminisation)]

Raine spun around in front of his Mistress for her to appraise. She hummed slightly.

"I think, Raine, that this dress might be a bit too conservative for you." She said

"I agree Mistress, this is too dignified for a slut such as myself." Raine concurred.

"Hmm... Let's try the next one on then." she said, gesturing to the attendant to hand her the next dress as Raine undressed.

This next one was much sluttier, a simple but tight black dress made of some sort of fabric. It ended just barely covering Raine's ass. It wasn't dissimilar to Mistress's dress that he'd tried on before, but it actually seemed to fit him. Like that prior dress, his cage was clearly visible under the dress, pressing against the fabric as though it were trying to escape.

[Short Dress Equipped! +5% arousal (Feminisation)]

"I like this one much more Mistress!" Raine said cheerily, as he spun around once more to show her it in full.

"Yes, this one much better fits your purpose I think." Mistress Tazamoth agreed.

"Thank you Mistress!" Raine responded.

"Let's try this last one as well, then we can go home" His Mistress said.

Raine took off the dress, and was handed a new one, it looked to be the same shape as the one he had just tried on, but this dress was made of Latex, [Dangersense] pinged, informing him that there was an enchantment on it. Uncaring, he slipped it on quicker than he had the other two, despite the nature of latex making it harder, he had grown a little more familiar by now with wearing dresses. The cool sensation of latex on his skin soon affected more of his body, beyond just his arms and legs. He was starting to grow to like the feeling, the way it numbed his non-sexual senses slightly and the way it clung to him as though it were a desperate lover. The latex felt especially nice on his caged cock and shrunken balls, the black fabric eliciting a small spurt of precum that soon dripped down onto his thigh.

[Enchanted Latex Dress Equipped! +5% arousal (Feminisation)]
[Primary Enchantment Activated! Skin tight Enchantment!]

Raine read the enchantment's description.

[Skin tight Enchantment: This article of clothing will conform tightly to your skin, preventing creases. It will accommodate minor changes to your body shape over time as well.]

'Oh that's good, it'll keep up with my [Feminisation]' Raine thought.

"Mistress, can we get this one please? I like it best!" Raine plead to his beloved Mistress.

"Of course Raine, why don't you let me pay for it and then we can go back home, ok?" Mistress Tazamoth said, before turning and talking to the Demoness attendant once more. Soon after, she handed the Lesser Demoness a few coins and then turned back to Raine, strutting past and leading him out of the building with an authoritative tug on his leash. As he stumbled to keep up, he was once more reminded of the large butt plug buried in his ass as it began to bring him more and more pleasure just as he kept up with Mistress. He let out a whimper as his cock drooled its watery thin precum onto the street. His Mistress seemed either not to notice or not care for her covenanter's plight as they passed through the bustling streets, despite his increasingly loud whimpers and poorly stifled moans. Finally, they came to the gate, walking down the street to it however, sent Raine over the edge. Orgasm hit him and he twitched and quivered as he came, no ejaculate escaping but plenty of precum pooling on his shaking thighs and falling onto the floor as he came in public. A few Demonesses and even other covenanters around them gave him appreciative glances as his Mistress finally turned around.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 68 ===> Level 69]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[You came in public. +1% Feminisation]
[[Sexual Frustration] decreased in level. Level 37 ===> Level 36]

Raine began to read the notifications but his attention soon turned to his Mistress.

"Oh? Did my Little Raine cum in public? What a little slut he is huh? How pathetic is that?" She teased.

"Mmmph... Y-yes Mistress. I did cum in public like a pathetic slut." Raine said meekly.

"Well, my Little Raine will have to be treated at home, if he is able to cum like that in front of a crowd." Mistress Tazamoth said, hinting at some later sexual adventure, "For now though, he'll just have to try not to cum anymore on his way back home."

An impossibility. Raine was certain that he'd probably cum again before they got back. Still he resolved to at least try not to, if that was what his Mistress wanted of him. The two soon left the city, and Raine could already feel his body heating up, the lust within him rising once more, preparing him to cum once more. They'd barely made it 10 minutes of the journey before Raine sank shakily to his knees, cumming himself silly.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 69 ===> Level 70]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[[Sexual Frustration] decreased in level. Level 36 ===> Level 35]

"Hmm... It seems my Raine failed his little challenge. What a weak-willed little male." His Mistress mused.

"S-sorry Mistress. I'm... just a pathetic and sensitive little failed male." Raine apologised.

"Good boy Raine, that Hypnotism is really good at helping you express your understanding of your place in the world." Mistress Tazamoth said.

"I- Thank you Mistress? I-I really enjoy... watching the spiral. It makes me a good boy." Raine said as he stood up.

The two carried on towards their home. Raine only came one more time, just 15 minutes out from the house. 

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 70 ===> Level 71]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[[Sexual Frustration] decreased in level. Level 35 ===> Level 34]

The door was opened, and the leash was removed from his collar. Raine was glad the collar's heavy weight didn't come off, and that it stayed as a reminder of what he was - a failed male relegated to being Demoness fuckmeat. He followed his Mistress into her bedroom, trailing behind her as she walked through the hall. After he entered, his Mistress closed the door behind him. Now a familiar predatory grin rose to her face, as she stared at Raine lustfully. She stripped, freeing her hard and thick shaft and unleashing her large tits. Raine found his eyes drawn to his Mistress's large breasts as the enchantment on her piercings grasped at his mind.

"On your knees Raine." She commanded.

Raine obeyed, unthinkingly. He knew what was coming now, and he waited eagerly. His Mistress soon walked over and presented her throbbing cock to him.

"Suck."

"Yes Mistress" Raine said, grasping the engorged member, massaging it before licking the tip. Precum spilled out of the head onto his tongue. He licked his Mistress's cock again, before placing his lips around the head of her shaft. Slowly and methodically he worked his way down the shaft, getting about three-quarters of the way down before gagging and attempting to pull back. His Mistress's strong hands reached down, forcing him back down the cock, pressing his nose into her pubic fat, even as he choked, coughed and spluttered on her massive cock. Soon she began roughly fucking his throat, the harsh treatment bringing him pain but also pleasure as she used him as her fucktoy. Saliva spilled out of his mouth, down his front, all over his new latex dress. At the same time, precum spilled out his wet cage, soaking his thighs in the thin watery liquid. After a few minutes of oral brutalisation, Mistress Tazamoth finally drew him down her shaft one last time, pressing him into her crotch as she shot ropes of thick, virile semen down his throat.

[You have brought your Mistress to orgasm. +10XP]
[You swallowed Demon Semen. +2XP, +0.1% [Feminisation] Progress].
[You have ingested Aphrodisiac Fluids (Semen). [Aphrodisiac Affected] increased in level. Level 23 ===> Level 26]

Finally, his Mistress drew back, letting Raine breathe. He gasped desperately for air, as a mixture of cum and spit ran out of the corners of his mouth and tears welled up in his eyes.

"My my Raine, you look so cute like that!" Mistress Tazamoth cooed, "Why don't we move to the bed and do some anal now?"

"Y-yes please M-m-Mistress" Raine said as he came down from the orgasmic high.

The pair got onto the bed, His Mistress soon pulled the butt plug out of his wet asshole, and he felt her own shaft probing at his entrance. It slid in, stretching out his ass once more. Pain from the stretching turned into more pleasure and he soon found himself squealing and moaning like a girl. Each powerful, painful thrust driving his poor little brain wild with pleasure. Then, his Mistress reached a hand around to grab his caged genitalia. She adjusted her grip, hand now firmly grasped around his small balls. Her other held him in a headlock, pinning him to her. Her hand clenched, and pain bloomed as he felt his balls being crushed by her powerful vice-like grip. He almost passed out between the initial wave of pain and the aroused wave of pleasure that followed it. All the while, she kept pounding his femboy ass.

[[Pain Into Pleasure] increased in level. Level 24 ===> Level 25]

The pleasure increased slightly, and Raine could hardly think. His Mistress continued squeezing his sensitive, shrinking sack, slightly gentler than the initial one, but still enough to torture the useless things and drive Raine crazy. Soon, he felt himself cumming, Mistress Tazamoth didn't stop the fierce assfucking or ball torture for him though.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 71 ===> Level 72]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 15 ===> Level 16]
[[Anal Sensitivity] increased in level. Level 19 ===> Level 20]
[[Sexual Frustration] decreased in level. Level 34 ===> Level 33]

His Mistress continued on, obliterating his weak ass. Soon, he found himself cumming again, this time however, his Mistress came with him, and came in him.

[A [Succubus] has brought you to orgasm. [Body Sensitivity] has increased in level. Level 72 ===> Level 73]
[You came in chastity. +0.1% Feminisation]
[You came hands-free. +0.1% Feminisation]
[You came from anal. +0.1% Feminisation]
[You experienced a dry orgasm. +0.5% Feminisation]
[[Succubus Covenant Crest] increased in level. Level 16 ===> Level 17]
[[Anal Sensitivity] increased in level. Level 20 ===> Level 21]
[[Sexual Frustration] decreased in level. Level 33 ===> Level 32]

[You have brought your Mistress to orgasm. +10XP]

Raine felt massively tired, barely flinching as his Mistress slipped out of him and replaced the butt plug. Already he felt himself falling asleep, even though he had no idea what time it was. His Mistress too seemed tired, rolling onto her back and lying still, as far as he could hear. He eagerly awaited tomorrow's 'playdate' as he fell asleep.

-----------

Changes this chapter:

[Special Trait Increased: Feminisation: 21.3% ===> 26.1%]

[Special Trait Increased: Succubus Covenant Crest: Level 15 ===> Level 17]

[Permanent Effect Increased: Body Sensitivity: Level 68 ===> Level 73]

[Permanent Effect Increased: Pain into Pleasure: Level 24 ===> Level 25]

[Permanent Effect Increased: Anal Sensitivity: Level 19 ===> Level 21]

[Effect Decreased: Sexual Frustration: Level 37 ===> Level 32]