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Dan has lost a bet. Because Clockwork was a fucking cheater. And the wager had been that the winner got absolute control over what they did in the bedroom that night.
So, there Dan was, buck naked and chained to the bed. To add insult to injury, Clockwork was making him wait.
Dan stared up at the ever-turning gear patterns on the ceiling. Whenever Clockwork made him wait like this, it usually meant they had something unusually fucked up in mind. Considering some of the shit they’d gotten up to before, he was a bit nervous to see what they had for him tonight. The chains were another bad sign; that usually meant Clockwork was tapping into their sadistic side.
All in all, Dan had a feeling he was going to be hurting tonight. And he was absolutely not getting hard just thinking about it. Absolutely not.
Finally, the door opened, and Dan heard the sounds of industrial wheels against the wooden floorboards.
“Took you long enough,” he griped.
“My apologies, I had to prepare my equipment,” Clockwork said,
They finally floated into view. They were wearing a white coat and a head mirror.
“Who the fuck are you supposed to be? Dr. Malpractice?” Dan asked scathingly.
Clockwork chuckled, flashing Dan a grin with far too many pointy teeth, as they pulled the cart up next to him.
Dan surveyed the tray of “tools” warily. The first things he laid eyes on was a selection of varied dildos and a harness, which were sitting among a bunch of metal tools that looked much more medical in use.
“Ugh, don’t tell me you’re planning to peg me while playing ‘doctor’.”
Clockwork smirked. “I don’t know what you’re talking about. These are specialized tools.”
“Okay, you’re in that mood. Care to enlighten me on what I’m in for Docwork?”
Clockwork picked up a pair of rubber gloves from the tray and pulled them on with a snap. Then they picked up a bottle of lube.
“You’re overdue for a prostate exam,” they said.
Dan snorted. “Thought you were supposed to be over fifty for those, and living. Guess what, chucklefuck, I don’t meet those criteria.”
“Your recent bloodwork showed cause for concern.”
“What fucking—? Never mind, let’s just get on with this.”
Clockwork snapped their fingers and the ecto-chains rearranged themselves, pulling Dan around so he was laying sideways across the narrow part of the bed, and his ass was sitting right at the edge with his legs hanging off the side.
Clockwork pulled up a pair of stirrups from under the bed, which definitely hadn’t been under there before they came in. So, Ancients only knew where they pulled them from.
“Feet in the stirrups, please,” they said, brusquely, as they grabbed a couple pillows from the head of the bed. One was tucked under Dan’s head, the other shoved under his hips. “Are we comfortable?”
“Pretty sure this isn’t how you conduct a prostate exam, Dr. Asshole,” Dan said. “But yeah, as comfortable as is possible when I’m fucking chained down and got my bare ass hanging out.”
“Understandable. I’m going to begin my exam now.”
“Get on with it then.”
Without further ado, Clockwork stuck a lubed finger into his rectum and placed a gloved hand on his abdomen. “Hmmm, I feel some possible abnormalities. I need to examine you a little more extensively. Please, hold still and try to relax.”
“What are you—holy shit!” Dan swore as Clockwork kneaded his prostate hard.
Suddenly, a second lubed finger was added in, stretching him slightly. Dan swore colorfully as the intruding fingers began massaging his prostate in the most delightful way. He moaned as Clockwork worked him up. The spring of pleasure in his gut winding up as his climax approached.
Then Clockwork withdrew their fingers.
Dan whined as the urge retreated.
“Such lewd sounds you’re making. This is a professional setting, you know. Have some decency.”
“Fuck you,” Dan snarled.
“Language,” Clockwork chided as they shed the gloves and walked around to the tray of “tools” again.
This time they picked up a thin, metal rod.
“What the fuck is that?” Dan asked.
“It’s a sounding tube.”
“And that is?”
“It’s a type of urethral dilator.”
“Oh fuck no, you are not sticking that thing in my dick,” Dan said, an edge of panic in his voice.
Clockwork hesitated for a moment then broke character. “Is that an actual no, Dan?”
“Yeah, that’s a hard fucking no.”
Clockwork immediately put the sounding tube down and slipped back into character. “Very well. We do have alternative options for this part of the exam.” They picked up a very normal looking cock ring and a small handheld vibrator that they had tormented him with many times before.
Dan swallowed down a moan of anticipation. “And what are those supposed to be for?”
“Testing penile function.”
Dan cackled. “You didn’t even try to come up with an actual medical purpose, did you?”
Clockwork smirked, breaking character slightly. “In my defense, this was the backup plan.”
“Well, get testing, Dr. Time.”
Clockwork grinned evilly, lubricated the ring, and slipped it onto his cock, which had softened slightly in the interim. Then they stroked it a couple times to bring it back to full harness. Dan groaned as the ring became constricting.
Clockwork clicked a remote and the ring started vibrating where it pressed against his balls. They then placed the handheld vibrator against the head of his dick and turned it on.
Dan closed his eyes, letting the delicious vibrations take him. If he hadn’t been so thoroughly chained down, he would have bucked into the sensation.
Then Dan was harshly reminded why he should never take his eyes off Clockwork when having sex, because they took advantage of Dan’s distraction to squeeze his balls. Hard.
Dan screamed, more from surprise than pain, but dammit, that did fucking hurt.
“Apologies for the discomfort—had to check for lumps,” Clockwork said, grinning mischievously.
“Yeah, sure. Definitely couldn’t warn me before you did that, Dr. Jackass,” Dan grumbled without any real heat.
“You might feel a slight squeeze.” Was all the warning Dan got before Clockwork slid what felt like two attached metal disks over his balls.
“Oh, fucking hell. You had to pull out the ball crusher. I knew you were feeling sadistic today,” Dan groaned. He would not admit that he felt a zing of heated arousal go straight to his dick at the idea of Clockwork crushing his balls while fucking him senseless with the strap-on.
Clockwork’s answering grin showed more than a few teeth as they began tightening the device.
Dan gritted his teeth. Between the uncomfortable—and knowing Clockwork, soon to be agonizing—pressure of the crusher, along with the continued vibrations from the ring and vibrator—Clockwork had switched to holding the latter in place with telekinesis—had him balanced deliciously on the brink. But Dan had the nagging suspicion that Clockwork was not going to let him cum yet.
As he suspected, just as the mix of pleasure and pain was becoming unbearable, the vibrations switched off.
Dan let out a pitiful moan, panting as he gathered his wits as much as he could with the vice-like pressure still on his balls.
Clockwork took away the hand held vibrator and turned the bolt on the crusher another full turn, bringing the pressure up to agonizing.
Dan growled, claws digging deep furrows into the mattress.
“You’re doing very well, Dan,” Clockwork said gently.
Dan snarled, even though his core warmed at the praise.
“Now,” they said, resuming their businesslike tone, ”your prostate exam earlier showed limited blood flow.” Both ghosts smirked at the little joke there; Dan’s smirk a little strained from pain. Clockwork continued, “My recommended course of treatment is intense direct stimulation to the affected area until the symptoms resolve.”
As they said this, Dan heard the clink of metal and the scrape of something being pulled off the tray. He looked over to see them fastening the strap-on harness around their hips. A hot pink dildo stood up proudly in front of them.
“Did you have to choose the pink one? Really?” Dan griped.
Clockwork smirked, stroking their fake cock. “It seemed the most efficient for the treatment plan.”
Dan swallowed as Clockwork clicked the remote to turn the cock ring’s vibrations back on.
Clockwork took up position between his still spread legs as they lubricate the dildo. “Are you ready?”
“Yes,” Dan said, looking up at the ceiling and forcing himself to relax as much as he could.
Clockwork went slowly when pushing themself in, for which Dan was grateful. The pink dildo wasn’t long, but it had a decent girth and a slight upward curve to it. It was very much meant for prostate stimulation. Though it had been a while since Clockwork had pulled it out, so, he had forgotten one important detail about that toy.
Clockwork ground their hips into him. Dan moaned, bucking up to meet them as much as he could while still restrained. Each delicious rock had him seeing stars. Then Dan heard a slight click, and suddenly the dildo was applying deep vibrations directly to his prostate from the tip grinding hard against it.
Dan gasped and inhaled deeply, grinding down into the toy. He could feel the metaphorical spring winding tighter in his gut.
“Having fun?” Clockwork asked gleefully.
Dan nodded breathlessly.
“Well, for your treatment, it’s time to increase the intensity.” There was another click and the vibrations intensified.
“Shit! Oh God! Fuck!” He cried as his partner ground the vibrating tip into his prostate unrelentingly. With a sharp cry, the spring snapped, and Dan orgasmed so hard blackness threatened the edges of his vision.
As his senses came back to him, so too did the feeling of the vibrations against his most sensitive parts. Clockwork hadn’t turned off either the cock ring or the dildo; in fact they’d turned them up.
“Ah! Fuck!” Dan gritted his teeth, fighting through the overstimulation. Already, his cock was back to full hardness.
Clockwork rubbed against a particularly sensitive spot inside him, and Dan’s eyes rolled back, losing himself in pleasure and pain. Clockwork grinned evilly, intensifying their grinding against that pleasurable spot, and Dan shouted as he climaxed a second time.
As he came down from that second high, Clockwork turned both vibrators up to their maximum setting.
Dan swore explosively, his eyes pricking with tears as Clockwork shifted to thrusting, pounding the dildo against his screaming prostate. The cock ring rattled against his equally tender balls. This abuse carried him through a third sharp climax that caused his tears to start falling.
At this point, cum was leaking weakly from the tip of his thoroughly overwrought cock. His parts were too overstimulated to produce any more than that.
All of a sudden, there was a shift in the air of the lair, and the little pink prostate tormentor wasn’t inside him anymore. Instead, Clockwork had stopped time and switched it out for a massive, ridged dildo and had manifested a cock of their own, both of which were spearing him open uncomfortably wide. The ridges on the dildo grated against his already tenderized prostate as Clockwork pulled both cocks back and slammed back into him. Dan sobbed as the two slick dicks slid in and out of his tender asshole, working him up to a fourth orgasm that had him sobbing and gasping for air he didn’t need.
As he came down from that release, Clockwork became almost gentle as they continued to fuck into him. When they tapped his hip to catch his attention, he saw why. Presumably also in the time stop, they’d switched out the cock ring for two thin aluminum loops around his cock with wires leading off of it to a little box on Clockwork’s hand.
“Oh fuck,” Dan groaned upon seeing the electrostim device.
“If it’s too much, we can stop,” Clockwork said, pausing in their rhythm.
Dan shook his head. “I-I can take it,” he gasped out. “Zap me.”
“I’ll start the voltage low,” Clockwork said gently.
The device let out a low buzz as it hummed to life. Clockwork slowly turned the twin dials and the electricity crackled lightly as light tingling sensations tickled his cock.
Dan moaned weakly, enjoying the sensation even despite being overstimulated and sore.
“I’m turning it up now,” Clockwork said.
They turned the dials up slowly, increasing the voltage and frequency until it was like bees stinging his tender cock every few seconds.
Dan swore, fresh tears leaking down his cheeks as Clockwork began thrusting again.
Between the electric stings on his straining cock, the dick and dildo roughly fucking his ass, and the ridges all but tearing his abused prostate to shreds, Dan’s fifth orgasm came quickly and had him sobbing and cursing as his dick spasmed but no cum came out.
Clockwork turned up the e-stim machine again, this time until the current became near constant and painful. And then, as they started fucking him again, their penis started moving in a way that was distinctly not human.
“What is it with you and the—aaah!—tentacles?!“ Dan forced out between sobs.
“It’s more effective for deep tissue stimulation.”
As they finished speaking, the tentacle dick shoved itself deep into Dan’s ass making the man scream as he forcefully came a sixth time.
Clockwork ran a gentle hand up his thigh. “You’re doing so well, Dan. Just a little more. Cum one more time for me.”
Dan nodded, still sobbing.
They reached down and turned up the e-stim one last time. The constant agonizing current coursing through his penis made Dan scream as Clockwork started pounding their dicks into him. Instead of the ridged dildo, the prostate tormentor was back and had the vibrations turned all the way up. Clockwork jackhammered his prostate like they intended to vaporize it. Their tentacle dick continued writhing around his insides like there was no tomorrow. All this intense stimulation sent him screaming over the edge into his seventh and final orgasm.
This proved to be too much for Dan. Blackness overwhelmed his vision and he knew no more.
***
Dan woke slowly to someone’s cool hand patting his cheek. He groaned and opened his eyes. He felt sluggish, like he had taken a twenty minute afternoon nap that lasted four hours.
Clockwork was looking down at him a little worriedly. They’d shed the doctor's getup and apparently removed all the toys and unbound him while he had been out.
Before he could even ask, Clockwork said, “You were out for less than a minute. I used a time stop to remove the equipment in hopes that you would be a bit more comfortable upon waking.”
Dan nodded then winced as all the genital abuse started to catch up with him. “I don’t think comfortable is the right word, Clocky.” Dan used a touch of flight to sit up without putting any pressure on his evicerated ass.
Clockwork clicked their tongue, expression sympathetic. They grabbed a blanket sitting folded near the end of their tail and tucked it around Dan’s shoulders. “You’ll want this, and I have ice water and some chocolate that I’d like you to eat.” They put three chocolates and a plastic cup half filled with ice water in his slightly trembling hands.
Dan was too sore and tired to put up his usual protests about not needing to be babied.
He took a couple small sips of the water then put it aside to unwrap one of the chocolates. He popped it in his mouth and chewed, then sighed blissfully. It was Hershey’s special dark, his favorite.
Clockwork rubbed his back gently. “You did really well, Dan. That was a lot to handle. I’m proud of you.”
Dan blushed, tucking his face down into the top of the blanket to hide his flushed cheeks. “Shut up,” he mumbled.
Clockwork smiled at him and ran their hand through his hair. Dan did not lean into it. Absolutely not. “When you’re done with those I have some chamomile tea for you, if you want it. Also,” An ice pack on a towel appeared in their hand. “You’ll probably want this.”
Yeah, Dan definitely wanted that. He took the ice pack from them and clumsily wrapped it in the towel in his eagerness to soothe his abused dick and balls. He winced.
Clockwork pressed a light kiss to his exposed shoulder. “Is there anything else you need right now?”
“Just you,” Dan said shyly.
Clockwork smiled and pressed into his side. “I’ll admit, I’m a little surprised we both got all the way through such an intense scene. You’re so strong, Dan.”
”It fucking hurt, still does.” He re-adjusted his grip on the ice pack. “But I know you know when to stop. You wouldn’t push that.”
“Never,” Clockwork said firmly.
Dan finished the second chocolate, and the water, holding back a yawn. Clockwork took the wrappers and cup from his hands and set them aside.
He could feel himself being guided into a more comfortable, prone position, even as he fumbled with the third chocolate. The soft pillow under his hips kept his tenderized meat from rubbing too much on the bed, and the firm pillows under his chest and packed around his ribs would keep him from pulling any other muscles. He finally freed the chocolate from its paper prison and popped it in his mouth, savoring the bittersweet flavor. One of the pillows was tugged away and replaced with a cool body that snuggled up close.
Clockwork grabbed his arm, draping it over their torso, and they settled in to share a nap with him. Dan turned his head away so Clockwork wouldn’t see his dopey smile as his eyelids drooped closed. Soon, the comforting ticking of Clockwork’s core lulled him into a deep, dreamless sleep.