Chapter Text
Atonement. As a religious man, this was a concept that Rollo Flamme was intimately familiar with. Sins must always be paid for‒ he understood that much‒ and what he saw as a righteous act had instead branded him a sinner in the eyes of the students from Night Raven College. They were the only ones who knew the truth behind the firelotus outbreak and, therefore, the only ones who could ensure that he paid for his transgressions.
Yet they had no plans to enact any sort of punishment upon him. They were content to let Rollo stew in his own guilt until he confessed or took the truth of his crime to the grave.
At least, that’s the way it had seemed.
He should’ve known better than to think that the great mage Malleus Draconia would be satisfied with simply allowing Rollo’s own conscience to torment him. Rather, Malleus had conjured up a unique form of penance that could only be conceived of in a mind as lascivious as his: something that would more than make up for all of the merriment that the Night Raven boys had been deprived of during their struggle against the firelotuses, and that would come at Rollo’s expense.
Rollo Flamme, Student Council President of Noble Bell College, was to spend the evening having sexual relations with each of the Night Raven students in turn, servicing them in whatever way they desired. The thought made Rollo shudder. Such sins of the flesh were beneath him. He couldn’t fathom why he’d agreed to these terms in the first place. Surely Malleus had placed some sort of spell on him to charm him into agreeing, to draw Rollo’s attention to the way his emerald eyes shone in the moonlight, to tempt Rollo to fantasize‒
No, he hadn’t the time to be pondering such debauchery! The first of the Night Raven boys would be here at any moment, and Rollo needed to be ready for whoever it would turn out to be.
Thankfully, there had been a spare room in Noble Bell’s dormitories in which they could conduct their… rendezvous. Rollo would’ve been mortified had they been forced to use his own personal chambers; he would’ve had no choice but to burn his bedsheets afterward to rid them of the stench of sex and sin.
It had taken quite a bit of effort for Rollo to sneak away to the spare bedroom in the midst of all the festivities. Once there, he’d been disgusted to find that the Night Raven students had wasted no time in filling it with all manner of sexual gadgets and paraphernalia. He didn’t know if they’d been conjured with magic, bought somewhere in town, or simply happened to have been packed alongside the other boys’ luggage. He wasn’t sure he wanted to know, as all three options were equally depraved.
Still, Rollo supposed that would save them some time at the very least. The faster he could please his gentleman callers, the sooner he could return to the ball downstairs‒ hopefully before anyone else even noticed he was gone.
Rollo settled himself at the edge of the mattress and waited, willing his heart to stop racing. He couldn’t let these boys see through him. He had to maintain his composure no matter what; there would be no hiding behind his handkerchief tonight.
It took all of Rollo’s self-control not to jerk his head toward the entrance when he heard the heavy wooden door creak open. Instead, he turned his gaze slowly toward the sound, his expression carefully neutral as he waited for his first visitor of the night to reveal himself.
When the other boy stepped into the room, Rollo immediately recognized him by his vibrant red hair: Riddle Rosehearts.
“Good evening, Rollo.” The Heartslabyul housewarden’s greeting was far too polite, in Rollo’s opinion, for their current situation. He felt his entire body tense as Riddle turned to shut and lock the door behind him. There was no changing his mind now that the bedroom’s only exit had been effectively blocked off.
“Spare me your formalities,” Rollo snapped, the knuckles on his tightly clasped hands slowly turning white. Despite his apprehension, he did not falter, his gaze locked on Riddle’s face to watch for any sign of a threat. “We both know you’re only here to sleep with me, as per the arrangement. To pretend otherwise would be foolish.”
“I suppose you do have a point. I had intended to be gentlemanly about it,” Riddle replied, a wicked glint in his steely blue eyes, “but if you’d rather I forgo propriety, I would be more than happy to indulge you.”
“I didn’t intend‒”
“SILENCE!”
Rollo was shocked by the sheer force behind the command that came from Riddle’s mouth. Despite his short stature, the redhead’s presence was imposing in a way that made the back of Rollo’s neck sweat. There was no doubt in his mind that Riddle could easily overpower him with magic, so Rollo stayed quiet, sitting perfectly still on the bed as Riddle approached him. The heels of Riddle’s polished boots clicked on the stone floor with every step he took.
“During our time together, you are not to speak unless you are spoken to. Otherwise, you will be punished. Understood?” Riddle made his way to the wardrobe on the other side of the room, not even sparing Rollo a glance as he passed the bed where he was seated.
Rollo glared over his shoulder at Riddle, who had busied himself with rummaging through the wardrobe, presumably gathering whatever tools he planned to use during their encounter. It was utterly degrading to be spoken to in such a way, as if he were some sort of pet to be ordered around at will. Rollo felt his cheeks heat at the thought.
This was swiftly followed by the hot sting of a smack across his face.
Rollo looked up to see Riddle standing over him with a riding crop in his hand, tapping it impatiently against his palm.
“I believe I asked you a question.” Riddle raised an expectant eyebrow at Rollo. When he received no response, he raised the crop once more, landing an even harder smack on Rollo’s other cheek. He propped one boot-clad foot against the side of the mattress, looming menacingly over Rollo as he spoke. “Do. You. Understand. Me?”
Intimidated by the unexpected display, Rollo dropped his head in defeat, not daring to meet Riddle’s gaze. Defiance would be met with more pain and humiliation, only prolonging their encounter. It was in Rollo’s best interests to submit to the mage before him, as much as he was loath to admit it. “Yes, I understand.”
Riddle placed the tip of the riding crop under Rollo’s chin, tilting his head up to face him. “That’s ‘Yes, sir,’” he corrected with a cruel smirk. He slowly dragged the soft leather tip of the riding crop up the side of Rollo’s face before pulling it back to land another blow to Rollo’s already-abused cheek.
Rollo hissed in pain, bringing a hand up to rub at the tender flesh the crop left behind. His mouth had gone dry but still, he managed to force the words out. “Yes, sir.” His cheeks were red from both embarrassment and abuse. He hoped this would be over quickly.
“Good boy.” There was a subtle purr in Riddle’s voice as he spoke, and Rollo was appalled by the effect it had on him. Riddle took a step backward. For a moment, Rollo feared Riddle could somehow sense his cock twitch from underneath his robes, but he simply gestured for Rollo to stand. “Strip for me.”
Riddle’s gaze was intense as he watched Rollo remove his intricate uniform piece by piece. Rollo cursed himself for being unable to keep his hands from shaking as he slid his robes from his shoulders, undoing the intricate clasps as delicately as possible. He felt vulnerable enough being forced to strip naked; any additional signs of weakness were unacceptable.
When the last of his robes had fallen to the floor in a puddle of fine fabric, Rollo stood before Riddle in nothing but his briefs and stockings. As exposed as he felt, he refused to cover himself, determined to mask his insecurity even as Riddle looked him up and down hungrily. Being studied like this made him feel as though he were a prime cut of meat on display at the butcher’s shop. He most certainly did not enjoy the feeling, despite the insistence of certain… intimate parts of him.
Rollo quickly grew impatient with being ogled, his mind drifting back to the ball. He couldn’t afford for all of these sessions to drag on this way, not if he wanted to avoid being asked about his extended absence later. Despite his better judgment, he opened his mouth. “Could we please get on with it already?”
Riddle lashed out with the crop again in an instant, this time striking the inside of Rollo’s newly exposed thigh. The pain made Rollo whimper and stoop forward, angling his lower body away from Riddle in an effort to protect his more sensitive parts. He wouldn’t put it past a mage like him to strike below the belt.
“I believe I instructed you to stay silent,” Riddle sneered, turning his nose up disapprovingly. His gaze was cold and calculating, and he looked Rollo up and down as if deciding what exactly to do with him. “Perhaps you need more discipline than I thought. Off With Your Head!”
Rollo felt something cold and metallic fasten itself around his neck in an instant‒ a collar of some sort, he realized, as his hands shot up to grab at it in surprise. This must've been Riddle's unique magic. Rollo could feel that the connection between himself and his magic reserves had been blocked. While Rollo was decidedly anti-magic, this only made him feel even more powerless at the hands of a skilled mage like Riddle.
Decidedly more baffling, however, was the sudden presence of a similar metallic sensation at the base of his cock, just above his testicles. Rollo tried to peek down the front of his briefs to see what exactly had happened, but the large heart-shaped piece of metal around his neck effectively blocked his view.
Rollo’s glance downward wasn’t lost on Riddle. The redhead stepped forward to take Rollo’s chin in his hand, stroking his thumb down the other boy’s cheek. The tenderness of the gesture caught Rollo completely off-guard.
“Don’t worry about it,” Riddle said, his voice equal parts soothing and commanding. “Go and get on the bed. I shall join you shortly.”
Rollo did as he was told, returning to his place on the mattress and rolling onto his side, facing away from Riddle and the wardrobe of iniquity. Behind him, Rollo heard a rustle of fabric that he assumed must’ve been Riddle removing his trousers. This was followed by the sound of leather and metal, which was far less easily attributed. Rollo was sure whatever instrument of sexual depravity Riddle was setting up was far beyond his own imagination.
Suddenly, Riddle’s hands were on Rollo’s waist, his skin soft but his grip firm. He slowly tugged Rollo’s briefs down his legs, pulling them off and tossing them aside, exposing Rollo’s shamefully half-hard cock to the cold air of the room. He then flipped Rollo onto his back with surprising ease, forcing him to take in the scene before him.
Riddle stood at the foot of the bed, still mostly clothed. His trousers, boots, and hat had all been neatly set aside on the armchair in the corner of the room. Instead of briefs or boxers as Rollo had been expecting, Riddle wore some sort of red leather contraption, straps and buckles holding it in place between his legs. Protruding from the metal ring in the center was something Rollo could only describe as a prosthetic phallus. It looked somewhat realistic, its color and size making it seem as if it could truly belong to Riddle, but Rollo could tell even at this distance that it was made from rubber or silicone rather than flesh and bone.
“Mm, do you like it?” Riddle purred, crawling his way up onto the foot of the mattress. “I thought it might be best to use one of my smaller toys on you since I expect you’ll be rather… tight .” This statement was punctuated with a click as Riddle opened the small bottle in his hands, pouring some of the clear liquid contained inside onto his fingers.
Rollo watched warily as Riddle massaged the liquid between his fingers, using his free hand to lift one of Rollo’s legs, revealing his puckered entrance. A mortified blush quickly rose up Rollo’s chest and face. He somehow felt even more vulnerable than before, his most sensitive areas exposed for Riddle to touch and ogle as he pleased. He had half a mind to snap his legs shut but knew another strike from Riddle’s crop likely awaited him if he did, so he begrudgingly allowed the mage to manhandle him.
“Do try to relax,” Riddle advised, rubbing soothing circles into the flesh of Rollo’s thigh, the kindest he had been thus far. “It will be much easier for you that way.”
Rollo felt Riddle’s slick fingers prodding between his legs and immediately stiffened up, despite Riddle’s instructions otherwise. “Hold on, what do you think you’re‒”
Rollo was immediately silenced with a resounding smack to the underside of his thigh, from Riddle’s bare hand this time rather than the riding crop. “Hush. Let yourself enjoy it.” He fondled the tender, reddened flesh under his hand as he slowly slid a finger in past the tight ring of muscle between Rollo’s cheeks, moving it in and out to get him accustomed to the feeling.
It was an odd sensation, to say the least, having his body breached this way. The pain quickly subsided following the initial penetration, lessening with each thrust of Riddle’s finger. He felt his body start to relax as the mage massaged his thigh with one hand and worked him open with the other. Rollo knew he shouldn’t have given in so easily, but the feeling wasn’t unpleasant, just… unfamiliar, and quite wet.
The painful stretch returned when Riddle slipped a second finger inside Rollo, causing a soft gasp to escape Rollo’s lips. He glanced down, tipping his head to peer past the bulky collar. The sight that awaited him made Rollo wish he hadn’t looked: Riddle was spreading his fingers apart little by little, coaxing Rollo’s entrance ever wider. It was vulgar! It was shameful! It was‒
“Ooh!” Rollo threw his head back, an almost pornographic moan torn from his throat as stars exploded in his vision. For a fleeting moment, he was afraid he’d given himself a concussion against the headboard before he realized that the collar around his neck would’ve prevented that. What was happening to him? Was this Riddle’s doing?
“It seems I’ve found your sweet spot,” Riddle chuckled, nudging his fingers around inside Rollo’s hole until he let out another moan, writhing underneath Riddle’s hands. The sensation was almost overwhelming. Shocks of intense pleasure coursed through Rollo’s body, the likes of which he had never felt before, causing his cock to stiffen and whatever Riddle had put around it to feel tighter.
Rollo simply didn’t understand how something so obscene could feel this good.
A third finger slipped inside him with little resistance, all three digits pressing up against his sensitive insides until Rollo was so overwhelmed that he could hardly breathe. It was a mercy when Riddle finally removed them, giving Rollo a chance to recover.
But why did Rollo suddenly feel so empty and, dare he say, disappointed by the loss? It was patently absurd, but he felt some small part of himself begging to be filled once more. He elected to ignore it. He refused to give credence to thoughts from such a primal, debased corner of his mind.
Despite Rollo’s refusal to vocalize his impure thoughts, Riddle still smirked as though he could hear them. He reached out a hand to stroke Rollo’s flushed cock, fully erect now from the attention his prostate had received. Rollo’s half-lidded gaze followed Riddle’s hand down to his shaft, finally catching a glimpse of the thing fastened around it: a miniature version of the metal collar around his neck, identical down to the shape and color.
“It’s a cock ring,” Riddle finally explained, sensing the question on Rollo’s lips. “It will keep you erect for longer and delay your orgasm.”
Rollo didn’t understand how that could possibly be pleasurable, but he swallowed his words when he felt Riddle press a finger against his lips‒ one of the dry ones, thankfully.
“Surely you didn’t think we were going to let you get off before we were satisfied,” Riddle purred, dragging his finger down Rollo’s chin, neck, and chest before stopping right above his cock.
Rollo shivered. Riddle’s use of the word “we” concerned him. Surely the Night Raven boys didn’t plan to leave this contraption on him while eleven different men had their way with him… did they?
Rollo didn’t have long to ponder the implications of Riddle’s statement as he was quickly snapped out of his thoughts by a strange buzzing sound and a soft moan that certainly hadn’t been his own.
Rollo looked up to see Riddle kneeling on the mattress in front of him, moaning softly as he stroked the prosthetic mounted on the front of his harness. His hand was still slick from where he had opened Rollo up on his fingers, and he now seemed to be spreading the leftover lubricant onto his silicone cock. The way Riddle was moving his hand paired with the expression on his face as he moaned with pleasure, it almost looked as if he were‒
Rollo quickly looked away, trying to hide his flushed face in the pillows only to find his efforts thwarted by the bulky collar still fastened around his neck.
In an instant, Riddle grabbed the collar around Rollo's neck with his free hand, wrenching his face back toward him. “Don’t you dare hide your face from me.” Riddle’s face was red, his breath coming out in gasps. He was close enough that Rollo could feel it hot and damp on his own cheeks. “I want to watch your expression while I finally fuck you.”
Such vulgar terminology sent a thrill down Rollo’s spine and straight to his cock for reasons he didn’t quite understand. He was so focused on the latest in his series of new and confusing feelings that it didn’t even occur to him that said fucking would be taking place that very second until he felt the head of Riddle’s cock nudge against his entrance.
“Wait, I‒ ooh!” The moment Riddle entered Rollo, it became obvious what exactly that odd buzzing sound had been: the toy inside of him was vibrating. If Rollo thought the pleasure before had been overwhelming, then this brand-new sensation bordered on incapacitating. Riddle wasn’t even halfway inside of him yet and Rollo was already lost in the feeling, moaning and panting despite his efforts to maintain his composure. He could feel himself drooling; it was just too much!
Rollo didn’t even think to ask him to stop.
Riddle continued to push further into him, stopping every so often to allow Rollo to adjust before thrusting forward once more. The stretch didn’t hurt this time; Rollo’s mind was completely occupied by primal, animal lust, pain turning into white-hot pleasure. He only noticed that Riddle had bottomed out when the redhead’s hips collided with his thighs, the vulgar smack of skin against skin filling the bedroom.
Riddle waited for only a moment before announcing, “I’m going to start moving now,” unable to rid himself entirely of his manners, despite his earlier threat. In contrast, however, he didn’t wait for Rollo to respond before grabbing him roughly by the waist and pulling out.
Rollo’s head swam when Riddle drove back into him. The vibrations only made it even more intense as Riddle’s cock rammed into his prostate with every thrust. The pace started slow but quickly grew fast and rough as Riddle began to chase his own pleasure, grinding against the base of the toy each time he buried himself inside Rollo.
Rollo could practically feel the bruises forming on his skin where Riddle was gripping his waist, moving him up and down on his cock as if Rollo were nothing more than a toy himself. He felt his erection twitch again, a stream of low moans he no longer tried to hold back pouring from his throat as Riddle pounded into him.
Rollo’s sense of time was quickly lost in his lust-addled brain. He couldn’t tell if it was mere moments or hours later when he felt Riddle go still inside him, letting out a loud moan that echoed throughout the room. His grip on Rollo’s waist tightened and his hips twitched, forcing the toy even deeper as Riddle rode out what Rollo presumed to be his orgasm. The continued pressure and vibration against Rollo’s prostate forced an animalistic, guttural sound out of Rollo that he hadn’t even known his body was capable of producing, his voice mixing with Riddle’s. Rollo might’ve even reached his own climax if it hadn’t been for the accursed ring fixed snugly around his cock.
Rollo sighed with equal parts relief and disappointment when Riddle finally pulled out of him, switching the toy off with a snap of his fingers. The mage took a moment to catch his breath, his face just as red as Rollo’s still-hard cock.
“That was incredible,” Riddle panted between breaths, using the back of his hand to wipe the sweat from his brow. “I’m lucky to have gotten to you first. I expect the rest of them will be leaving you well and truly wrecked.”
Rollo swallowed hard. If this wasn’t “well and truly wrecked” by the Night Raven boys’ standards, he had no idea what exactly he was in for. He was so thoroughly exhausted that he couldn’t do much more than watch while Riddle got up from the bed, unfastening the complicated mess of straps around his waist and thighs.
Riddle gathered up all of his toys and set them aside, storing them away from the ones that had yet to be used. Rollo assumed that this was to avoid contamination. He respected that, if nothing else.
Riddle then began to redress himself, pulling his trousers back on and adjusting his clothes in the full-length mirror by the wardrobe. With a quick wave of his hand, the collar around Rollo’s throat vanished; the cock ring, however, stayed in place, as did the barrier between Rollo and his magic reserves.
Riddle didn’t even seem to notice, tugging the brim of his hat into place before turning toward the door.
Rollo cleared his throat. He presumed that he was permitted to speak now that their tryst was over. “Aren’t you forgetting something, Rosehearts?” He rolled over to face the redhead directly, raising an accusatory eyebrow. Rollo could not allow Riddle, or anyone else, to know how much this little meeting had affected him.
Riddle paused to glance back at Rollo, his steely gaze raking over the other boy’s naked form. His eyes landed on the heart-shaped ring still firmly fastened around the base of Rollo’s cock, causing his expression to shift into a smug smirk‒ a far cry from the apologetic realization Rollo had expected.
Rather than responding to Rollo’s question verbally, Riddle simply snatched his riding crop off of the bedside table and gave Rollo’s bare ass one final smack, hard enough to make him yelp. Seemingly satisfied, Riddle continued his path toward the exit, the crop still in his hands easily passed off as a costume prop. He didn’t look back once, closing the door decisively behind him as he left.
Rollo had nothing to do now but sit and wait for his next guest to arrive.