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Five days. It had been five days since Cory had been locked into his chastity cage. Five horny days in which he was still expected to suck off and get fucked by both of his dominants whenever they requested. Cory wasn’t sure if he was in heaven or being tortured. His dick wasn’t sure either.
When Cory wasn’t horny (however rare that was), things weren’t as much of an issue. In fact he had gotten so used to the cage that a couple of times he had totally spaced and attempted to use a urinal, only to remember that due to his current predicament, sitting down to pee was his only option. While this had led to a couple of awkward bathroom interactions, for the most part Cory was in the clear.
But the rest of the time, when Cory was horny, he thought he might lose it. He wasn’t able to get hard in the cage, but that didn’t stop his dick from trying. It wasn’t painful, but it was a discomfort Cory was forced to learn dealing with on a daily basis. The fact that he found the cage itself hot enough to induce an erection was beside the point.
Not that he was ever alone with his thoughts enough for it to matter. Despite both boys now being in semi-regular relationships, their need for almost daily blowjobs did not abate. Cory frequently found himself on his knees with a mouth full of cock, his own straining in its cage between his legs. At least when they fucked him there was a chance he would still get off, but the boys also seemed to be making a point of using only his mouth, denying him of any orgasm at all.
He soon learned that whining about his predicament would be no good either. He was fine the first couple of days, but during and after what felt like a long weekend without sex, Derek and Nic found themselves fielding many frustrated pleas and complaints. After several repeat warnings, Cory was soon on the receiving end of a dubiously helpful “reminder spanking” and had a few more days added on to his punishment. His new unlock date would be next weekend, and he decided it was best to keep his mouth shut. Except when he was ordered to open it.
“Three more days.” Derek’s voice pulled Cory from his thoughts. “Think you’re gonna make it?”
“I hardly even notice it’s there anymore.” Cory looked around to make sure none of the other students having lunch were listening. “...unless of course, sir, you wanted to let me out early because I’ve-”
“Nope.” Cory knew that was a longshot.
“I think that's the closest you’ve come to begging since the weekend though, so congrats on that,” Nic spoke without looking up from his phone as he texted, probably with Amy.
“Yeah, you have been pretty good this week, boy,” Derek agree with Nic’s assessment. “The two of us are hanging out after school today, so let’s make sure you keep that up. Not that I wouldn’t be happy to assist if you need a little more correcting later.” He was just teasing. Right?
“No, sir,” Cory shook his head. “All good here.”
Derek turned to look at Nic who was still giving most of his attention to his phone. Things had been going well with him and Tricia, but Nic and Amy we’re almost inseparable. Derek and Cory were still hanging out with him, but there were more and more nights lately where he was ducking out early or showing up late because he was squeezing in some time with Amy. Nic had plans with her tonight, but apparently they still had a lot to talk about beforehand.
“You still hooking up with Amy tonight?” Derek deadpanned.
“Hell yeah dude,” Nic once again answered without looking up. “Gonna be fuckin’ awesome...”
Derek shook his head and looked at his watch. Lunch was almost over. “We’ll just head out after fifth period since Don Juan here has plans.”
“Yessir, Sounds good,” Cory nodded, then grabbed his bag as the bell rang. “Have a good night, sir.” Cory directed his final comment to Nic as he left. He meant it. He wanted to mean it at least.
Derek gathered his own things and stood up, waiting a moment to see if Nic would follow. He didn’t even seem to have noticed the bell, furiously texting - or more likely sexting - something to Amy. He weighed doing the right thing for a moment, but then decided it would be funnier to let him be late for class, so he left without saying a word.
“Strip!” Cory had barely closed the door behind him when he heard Derek give the order. He stared blankly for a moment before registering what he needed to do, dropping his backpack to begin disrobing. He had just put his shirt in his bag and was removing his jeans when Derek pulled a jockstrap from his own bag and tossed it to him.
“Wore those a few days,” Derek had removed his own shirt and belt, but stopped short of getting naked. “Feel free to give it a whiff before you put it on.”
Cory examined the jockstrap for a moment before giving it a sniff. Oh yeah, that’s the good stuff. He finished taking off his clothes and slipped the jockstrap on.
“Go put my bag in my room, put my shirt away, and then meet me back out here,” Derek spoke as he moved to sit on the couch.
“Yes sir,” Cory picked up Derek’s things and took them to his room, putting them where they belonged. When he re-entered the living room Derek was on the couch with his pants removed, legs spread wide.
“Good boy. Now get over here and get to work on my cock,” Derek pointed to the spot in front of him as he spoke. Cory silently moved into position as Derek continued speaking. “From now on, whenever you are home alone with me or Nic, you strip down to your underwear or a jock. Think of it like your uniform. I like your ass being easy access, and it’ll help remind you of who wears the pants around here.” Derek guided Cory’s head towards his dick as he finished his explanation.
Cory accepted Derek into his mouth without protest - complaining about the terrible pants joke wouldn't get his cage off any sooner. Besides, it’s not like he didn’t enjoy doing this. He just wanted this attention elsewhere. Maybe if he did a good enough job Derek would fuck him later.
Eyes closed, Cory moved his mouth down Derek’s length, taking it about three-quarters of the way before moving back up. This was practically an old trick to him by now, he knew this dick like the back of his own hand. Probably better, seeing as he couldn't really think of what the back of his hand looked like right now. But Derek's cock was a different story. He had mapped this thing out with his tongue so frequently he could probably describe it to a police sketch artist if he needed to.
As he bobbed his head up and down, he ran his tongue along the underside. He could feel Derek’s heart pulsing as he mapped out the skin with his mouth. He tightened his lips as he pulled back, leaving only the head in his mouth before swallowing back down the next 5 or 6 inches. He felt Derek’s thighs spread a little wider as he relaxed into the back of the couch, the hand that previously guided his head long gone.
*click*
The sound of a camera shutter, or at least an electronic one, froze Cory in his tracks. He opened his eyes and saw that Derek had his phone out, aimed at him.
*click*
Cory’s brow furrowed as Derek took another picture, this time with him looking into camera. He tried to protest, but a hand on his head kept the cock lodged firmly in his mouth, garbling any attempt at talking.
“Don’t worry, boy,” Derek encouraged Cory to continue sucking as he spoke. “No one is going to see these except you, me, and Nic.”
Cory made no attempt to resume sucking, attempting to give Derek a stern look which was probably betrayed by the fact that his lips were still stretched around a dick.
Raising an eyebrow at his sub’s display of defiance, Derek continued his explanation. “I thought it might be fun to tease Nic a little. Show him what he’s missing,” Derek reasoned, leveraging some of Cory’s jealousy to make his point. “Besides, you telling me you don’t wanna jerk off to this when you get that cage off?” He turned his phone around to show the screen to Cory.
Fuck. That was hot. Cory was looking at the first pic Derek had taken, his eyes closed, most of Derek’s cock in his mouth. You could see the last few inches between his mouth and groin, disappearing in the forest of pubic hair at its’ base. Derek flipped to the second picture, with Cory’s eyes open, and even that pic was hot. Cory decided he was very much okay with their activities being recorded, as long as they remained private. He resumed giving Derek his blowjob, silently consenting to any further pictures.
Derek smiled. He figured Cory would fight him at first on the pictures, but the chance to make Nic jealous would be enough to get him into it. Speaking of... Derek looked at the clock - Nic was still in class for another 20 minutes. He opened his texting app while Cory continued sucking. Tapping Nic’s name, he sent him the first photo he had taken, adding the words “wish you were here” to the image.
A few moments later, Nic replied with a solitary middle finger emoji. Followed by a request to `send more.’
Derek snickered to himself. He happily took a few more shots, each varying slightly by the amount of cock visible/swallowed. Then he used his hand to encourage Cory to take him even deeper into his throat, snapping a few more photos once he had swallowed him down to the base. He allowed Cory to pull back once he started to gag, taking the chance to send the new images to Nic.
`Fuck his face bro,’ was the reply this time.
“Well well well...” Derek spoke as he turned his phone to show the response from Nic. “We wouldn’t want to disappoint him, now would we?”
“No, thir,” Cory mumbled, mouth still full of meat.
“Good boy,” Derek spoke as he stood up with his hand still in Cory’s hair, moving Cory’s mouth with him. “Let’s help him make it through the rest of class.”
One hand holding his phone, and the other on Cory’s head, Derek began to pump his cock in and out of Cory’s mouth. At the same time he was also snapping photos with his phone, using his hand to position Cory how he wanted. He started fucking in and out of Cory’s mouth at a leisurely pace, making sure to capture the moment he held Cory’s head all the way down.
As he picked up speed, photos became more difficult to take without being blurry. So after settling into a good rhythm, Derek did the sensible thing and switched to taking video. Doing his best to watch the angle from the corner of his eye, Derek took the opportunity to show of some of his “skills” for the camera. Of course, Cory was doing most of the work, but that was just semantics.
Derek began fucking Cory’s mouth and throat with the full length of his cock. Cory, though gagging on occasion, did his best to take every inch without complaint. His hands grabbed onto Derek’s thighs, but made no attempt to slow or push him away, he merely needed some balance. Each time Cory would reach the base of Derek’s cock, Derek would hold him there for a few moments, before releasing him and allowing him to come up for air. Cory would cough or sputter on occasion, but Derek continued to thrust through it all.
After capturing a few minutes of their fun on film, Derek was getting close to cumming. Holding the camera directly over Cory, he looked down and renewed the grip he had on his hair. As he fucked Cory’s face with purpose, Cory could only look up into the camera as he accepted the oral onslaught. As he felt his orgasm approach, Derek reluctantly tore his cock from Cory, and began to swiftly stroke.
Aimed at Cory’s face and still open mouth, Derek fired off the first jettison of cum, which landed directly over Cory’s lips and the bridge of his nose. The following shots of cum continued to paint his face, splattering him like an abstract painting. Swallowing whatever cum had landed in his mouth, Cory leaned forward to take Derek’s cock back into his mouth for cleaning, sucking out any remaining cum he could find. All the while, Derek continued filming, not stopping until Cory released his now-cleaned cock with an audible *pop!*
“Fuck, boy, that was great,” Derek flopped back onto the couch behind him. “Hold still a second.” Derek took a few more photos of Cory’s cum covered face, his lips red and swollen from use. “Alright, go clean yourself up.”
Cory stood and walked to the bathroom, returning a minute later with a freshly washed face. He took a seat on the floor in front of Derek without being told. As he did, Derek leaned forward, once again showing him the screen of his phone.
“What do ya think?” Derek swiped through the photos before landing on the video. “Pretty hot right?”
“Yes, sir. Very hot,” Cory responded, mesmerized by the images of himself on the screen. “We should definitely do more of that. If you wanted to. Sir.”
Derek smiled as he pulled his phone back, once again sending a few things to Nic. A few photos, a clip of the video, and finally a shot of Cory’s messy face at the end. Class would be getting out soon, and Derek snickered at the thought of him having to walk out while trying to cover up the tent he was pitching.
“Now then, boy,” Derek turned his attention to Cory. “What should we do next?”
Nic adjusted himself in his pants at dinner. He probably shouldn’t have used Amy’s trip to the bathroom to look through the stuff Derek had sent him earlier but... oh well. At least he wasn’t in the middle of class this time. Asshole.
They were hot though. And that bothered him more then he wanted to think about right now. Should he really be getting turned on looking at two guys like that? He wasn’t gay. He was on a date with a girl right now, a girl he was going to take home and have very hot sex with. It just didn’t make sense.
Besides, Derek was only doing it to fuck with him. He shouldn’t worry about being so deep. He’d need to think of some way to get him back, though. He wondered if Amy would be up for recording anything...
“Hey,” Amy had returned to their booth and smiled at him from across the table.
“Hey,” Nic smiled back, the thoughts of his friends all but abandoning his mind. “Hope you’re having a fun night.”
“It’s been okay, I guess,” she teased him. “I think I’m ready to get out of here though.”
“Yeah? You got big plans later?” He teased back.
“Well, I just had this bottle of wine and a pair of handcuffs at home waiting...” She looked serious for a moment. “But, if you wanna keep hanging out in some old italian restaurant instead...”
“CAN I GET THE CHECK?” Nic looked around for their waiter, shouting his request. Come on man, he had places to go, tits to see...
This is not how Cory thought his Wednesday night would be going. He wasn’t complaining, he just really wasn’t expecting...this. Currently, Cory was on his back in the center of Derek’s bed. He was alone, which normally wouldn’t be a problem, but he was also currently tied to the bed. Maybe not tied, just...hooked? Is that what you’d say a carabiner does? Whatever. He was cuffed to the bed by his arms, both stretched above his head towards either corner of the bed.
When Derek had first had him sit on the bed and help him put his cuffs on, he figured he was about to spend some time being restrained. But then when Derek had him lie back and showed him the new bondage straps hidden under his mattress... Cory pulled on his restraints, testing them. Fuck, this was hot.
His ankles also had cuffs on, but Derek hadn’t attached them before he left the room a minute ago. He said he had to use the bathroom...it had only been a minute or two. Right? This wasn’t a prank...or part of his punishment. He didn’t think... He could probably unhook the cuffs if he needed to-
“How are your wrists?” Cory jumped, he hadn’t heard Derek walk back in the room. “Do they hurt at all?”
“No, sir,” Cory reflexively pulled on his wrists, testing the bonds. “They feel fine.”
“Good,” Cory watched Derek move to the foot of the bed as he spoke. At some point, he had put his cockring on. “Let’s get the rest of you strapped in then.”
Taking a hold of Cory’s right foot. He stretched it to the corner of the bed, attaching it to a strap that came up from under the mattress. He then did the same with the left.
“How’s that?” He tested the bonds on Cory’s ankle before allowing him to do the same.
“Seems fine, sir.” Cory wiggled his toes. “No problems so far.”
“Great,” Derek moved back up towards the head of the bed. “I’d ask what else you thought about it but you look like you’re enjoying yourself plenty.”
At the center of the bed, Cory’s cock was straining in its cage, a steady stream of precum leaking from the opening at the tip and leaving a wet spot on the front of his jock. Derek needed to make sure he checked the cage for washing later, something Carl had told him to look out for. He and the older man had kept in touch since meeting at the sex shop, Carl offering advice whenever Derek had a question about something involving Cory and his training. Derek had started look to him as a sort of mentor when it came to kink.
“You can thank Daddy Carl for the bondage straps,” he tugged at Cory’s bound wrist. “He showed me a few place online that I could find very specific types of toys.”
“Not bad for a test run,” Derek tweaked one of Cory’s nipples, causing the boy to jump. “And when we aren’t using them, the straps just fold under the mattress, hidden from anyone else.”
“They’re very...practical, sir,” though Cory was still pretty sure he couldn’t get away with hiding them at his house.
Derek pulled out his phone. “We should see what Nic thinks, right boy?”
“Yes. Yes we should, sir.” For... science?
As he was taking a few shots of Cory on the bed, Derek groped and squeezed his cock. He was starting to get hard again, thinking about the rest of his plans for the night. He kneeled up onto the mattress on Cory’s side, hardening cock still in hand. Then he was straddling Cory’s chest, his weight pressing Cory down into the mattress. He waited a moment, making sure Cory’s breathing wasn’t labored, before moving up towards his face.
Cory looked up as Derek towered over him. His dick, now once again fully hard, looked gigantic from this angle. Derek gripped it in his hand and brought it down, slapping him in the face a few times, each time leaving a smear of pre. Phone still out, Derek snapped a few more photos. Almost instinctively, Cory opened his mouth, chasing Derek as best he could in an attempt to capture him.
Derek teased him, his cock always just out of reach, tapping or stroking it against him where he couldn’t reach, streaks of precum dotting Cory’s face. Eventually, he acquiesced and allowed Cory to engulf him. At first only suckling on the head, Cory swallowed as much of Derek as he could from this angle.
Derek allowed him to bob awkwardly on the first few inches of his cock for a few minutes, enjoying the look of determination on Cory’s face as he dutifully attended to his dom. And capturing it on film, of course. Taking pity on the poor boy, he used his free hand to grab a handful of Cory’s brown hair. Pulling his head forward allowed Cory to swallow another few inches.
Derek pulled his cock from Cory’s mouth. Rather then release Cory’s head, he pulled it back towards the mattress. Kneeling up and forward, Derek reinserted himself, pressing his cock downwards into Cory’s throat. He still wouldn’t be able to seat himself fully at this angle, but this way he could still get most of his dick wet. Besides, Carl had showed him other positions that were perfect for face fucking, and he had other ideas for tonight.
Cory was doing his best to take everything he was being given. As Derek fucked down into his mouth and into his throat, he focused on keeping his throat relaxed and making sure to breath when he was able. He could feel the head of his dick scraping against his tongue, each time rebasting Cory’s tastebuds with his fluids. Cory moaned as he felt the grip of Derek’s hand in his hair tighten, only reinforcing his feeling of being restrained.
Derek slowed the pumping of his hips into Cory’s face, removing his cock. He wasn’t sure how Cory was going to react to what he was about to go, but he was pretty sure he’d be fine. Derek unstraddled Cory’s chest for a only a moment, turned around and re-straddled him in reverse. Then he moved backwards, hooked his feet over Cory’s arms, and lowered his ass to his face.
“Eat my ass, boy,” with one hand, Derek gripped Cory’s hair and pulled him upwards towards his ass. He sensed only a moment of hesitation before he suddenly felt a wet tongue against his hole.
“Holy shit does that feel good,” Derek groaned as he spoke, still holding Cory’s face against his ass.
For his part, Cory was also enjoying himself. He hadn’t ever done this before, of course, but he’d thought about it, and thought about having it done to him. When Derek first turned around he wasn’t sure what he was doing, knew even less when he started backing up. But he caught on pretty quickly once, you know, his face was shoved into an ass. That first lick was very, very tentative, but all Cory tasted was skin and... soap, maybe? That must have been what Derek was doing in the bathroom.
`Thank you, sir’ Cory thought to himself as he continued to lick across Derek’s hole.
“Fuck boy, seriously, should have had you doing this a long time ago,” Derek continued holding Cory by the hair as his ass was eaten, but his wrist was loose enough to allow Cory to move how he wanted for now. “Bet Nic will be too chickenshit to try this.”
`Yeah, probably.’ Cory thought about how Nic would freak out over anything being near his ass. Whatever.
Derek stroked his cock as he was rimmed, slow sliding his hand up and down as he ground his ass backwards into Cory’s face. This seriously felt amazing, I absolutely understood why people did this. Fuck, he could probably cum just from jerking off while he was doing this, if he wanted. But the plan wasn’t to cum yet, so he kept his stroking slow and steady, working himself up but not pushing himself close to the edge.
“Fuck, boy, get your tongue in there, fucking eat that ass,” Derek became forceful again with the grip on his hair, and Cory did his best to appease his sir.
Prodding gently at Derek’s hole, he pushed his tongue, again tasting only skin, soap, and maybe a little musk. He could only smell sweat and well, Derek, a scent he had become all to familiar with. A groaned a little as he pushed his tongue further in before pulling back a little, attempting to fuck his tongue in and out as he had seen done in porn. He heard an appreciative moan from Derek above him, so he figured he must have succeeded.
Derek continued pressing his ass back, wanting to feel more of Cory’s tongue. He was becoming more and more tempted to just say fuck it and stroke his cock until he came, but he still restrained himself. Allowing himself a few more minutes to enjoy Cory’s tongue on his hole, Derek lifted himself up and off of Cory, hearing the boy taking deep breath he probably hadn't even realized he was holding.
“Well,” he turned to look at Cory, his cock still hard and leaking in his hand. “What did you think about that?
Cory was still catching his breath. His face felt like it was covered in his own spit, his lips and tongue were sore from so much use. But he was so turned on, his hard cock still straining in chastity. He loved it.
“That was great, sir,” Cory spoke, his voice hoarse from disuse. “I didn’t think that would be something you’d be into.”
“I heard it on good authority that it would feel great.” Tricia, for one, seemed to love it. Carl also recommended it to him in passing. “They were right.”
Cory pulled at his bonds without thinking. He wasn’t sure what was next - Derek hadn’t cum, so he knew they weren’t `done’ yet. He watched as Derek moved back to the foot of the bed. He unattached each ankle from the bed straps, tucking them under the mattress when he was done.
“Just gonna try another position, boy,” Derek grabbed both of his ankles and pushed his legs back, getting on the bed between them as if he were going to fuck him. He could feel Derek’s hard cock slide against his jock-clad and caged one.
But Derek kept pushing his legs back, to the point of lifting his ass up off the bed partially. He then reached for additional straps from the head of the bed, attaching each ankle and adjusting the length so that both of Cory’s legs were pulled up over his head, his ass raised in the air. Derek slid a few pillows under his ass to help support his back, checking all of the restraints once more to make sure they were even and holding steady.
“How’s that feel boy?”
“Uh...okay, I guess, sir. Strange?”
“Good. Let me know if anything starts to hurt. You remember your safeword?”
“Yes sir, `bacon.’”
“Good boy.” Derek gave him a small slap on his ass and upper thigh before climbing off the bed once more.
From this angle, Cory couldn't easily see what he was doing, but it sounded like he was getting something from his closet. When he returned a moment later, in one hand he held a bottle of lube. So he was getting fucked tonight. Yay!
“Well don’t you look excited,” Derek teased. “But first...” He held his phone in his other hand, again taking pictures of Cory in his current predicament. Climbing on the bed again, He slapped his hard cock against Cory’s hole, the jockstrap allowing for only his furred hole to be on display. Derek snapped a few more photos of this, even teasing Cory’s hole, pressing his cock head against him and once again leaving a trail of precum in its wake.
It was this photo that greeted Nic as he exited Amy’s bathroom. Taking a moment to relieve himself, he had left her with he wrists cuffed together on the bed for a few minutes. He thought she would enjoy the suspense - she certainly loved the bondage.
But, fuck, when did D even get that shit for his bed? He watched a short clip Derek sent, slapping his cock against Cory’s hole and causing the boy to jump each time. D was definitely going to have to show him how to use that thing. And maybe where he got one. Would it fit under Amy’s bed...?
Fuck, Amy, right. He squeezed his cock in his hand, looking once more at his phone before turning of the screen. Nothing wrong with comparing notes with a bro, right?
Setting his phone to the side, Derek reached back behind him for something Cory hadn’t seen him put down. It was...a dildo. Huh? It was black, and not too big - about the same size as the one Cory had at home.
“Don’t worry boy, you’ll still get the real thing. You’ve just been pretty good these last few days and I thought you earned a little something.” As he spoke, he popped open the lid on the lube as he spoke. He applied the lube to the dildo, wiping his slick fingers across Cory’s hole when he was done.
Derek positioned the head of the toy at Cory’s hole. He looked up to Cory’s face, meeting his eyes as he pushed the toy forward, popping the head inside and causing Cory to groan. The two continued locking eyes and Derek continued to push the toy into Cory. Inch by inch, Cory squirmed against his bonds, whimpering as he felt himself stretched open for the first time in a few days on the toy.
Once it was fully inside, Derek held the toy still for a moment, jostling it only slightly against Cory’s walls. Then he tapped on the base.
“AAaaaaAAHhhhhhHHHh,” was Cory’s response as he felt the toy begin to vibrate within him, squirming even more then before. The toy continued to vibrate as Derek slowly pulled it back out, leaving only a few inches, and then pushing it back in.
Derek smirked as he slowly fucked Cory with the vibrator. Taking care to make sure he was aimed at the boy’s prostate, he kept his movements slow at first, letting him get used to the feeling. He’d used a toy on himself, but no one else ever had, and definitely not one that vibrated.
As Cory’s noises of shock died down, Derek started to fuck him faster with the toy. The shrieks of surprise had given away to the more steady low moans and groans Derek had gotten used to hearing from him. He meant what he said - Cory had earned this. He had talked to Carl about ways he could `reward’ Cory for good behavior, something that he would feel was just for him and not just incidental to something Nic or Derek wanted. This was one of the more simple ideas they’d come up with.
Cory watched Derek’s face as he fucked him with the toy. When his eyes weren’t rolling in the back of his head at least. He looked determined. His cock was still hard, and he looked like he would gladly replace the toy with himself any moment now. Cory hoped he would. He was smiling just a little, his eyes going from Cory’s face to his hole as he watched his own handiwork in action.
Derek was determined. He was going to push Cory over the edge, make him cum at least once, with only this toy. He watched as Cory’s breathing became more laboured, his moans louder. He made sure to angle the toy up and towards his prostate, his thrusts not too fast or too slow, scraping over it just right on every pass.
Cory began to pant, giving high-pitched, almost breathless moans. He could feel something building up in him, he could feel the pressure inside. He was going to cum if this kept up. Oh. That’s what Derek meant. This is what he earned. Cory relaxed for the toy as best he could, not that there was much of anything he could do at this point - Derek had it under control.
Derek could see that Cory was getting close and so he kept his thrusts steady, the moans growing louder and louder. Finally, Derek heard Cory’s whisper `fuck’ under his breath, and felt his hole squeeze around the toy tightly. Derek continued to push the toy against the straining muscles, fucking Cory as the prostate orgasm rolled over him. The wet spot on his jockstrap had grown even larger, and there was now a stream of precum dripping down from the fabric. Cory’s eyes again rolled into the back of his head before closing, his head falling to the side as he caught his breath. Once he felt his body relaxing, Derek gently removed the toy, setting it to the side.
Cory was just about to thank Derek when he felt him shift, and suddenly felt something else at his hole. Opening his eyes, he saw Derek was now once again kneeling over him, his cock pressed at his well-opened hole. His eyes went wide as he realized what was about to happen only moments before Derek pressed forward.
“Ooooooohhh fuuuuccckk,” was all he could get out as Derek pushed his cock into him, deep. He had already been opened up and lubed well by the toy, which combined with the fantastic orgasm he just had meant there was very little resistance for Derek. He eased in the last few inches, stretching Cory just a little deeper than the toy had earlier.
“Fuck, boy,” Derek spoke as though he had been holding back the floodgates. “Sorry, but I needed that.” He slapped Cory’s thigh to punctuate things, making Cory jump.
Placing one hand on the back of each thigh, Derek used his weight to press Cory’s legs even further back, using the leverage to begin sliding his cock in and out of Cory’s ass. Cory could only groan, not having had a moment to form a coherent thought since his orgasm. It was not unlike when Derek and Nic would both take a turn with him, never a moment between cocks to gather his wits.
Cory was okay with this, though. Derek wasn’t hurting him. Hell, maybe he’d even get to cum again - he still had 3 more days of chastity after all. He warmed to his second fucking of the night quickly, throwing his head back and moaning as he enjoyed the sensations.
See Cory relax fully was all the signal Derek needed to begin fucking in earnest. He pulled his hips back until only an inch or two remained within, then allowed his weight to carry him back down, slapping his thighs against Cory’s. Each slap of skin would be punctuated by a groan from Cory, a combination of the pressure over his prostate and some of the wind being knocked out of him. With Cory’s legs held up the way they were, neither boy had to worry about holding them up or that Cory’s muscle would get tired. He’d probably still be a little sore once they were done, but at the moment he couldn’t tell.
Derek dropped his upper body, holding himself up on his hands as his hips continued to thrust down into Cory’s hole. His face hovered inches above as they fucked, breathing heavily, faces red. Sweat dripped from Derek’s face, down his nose until it dripped onto Cory’s cheek. Both were silent other then the animalistic grunts and groans they couldn’t help but making.
A feeling of possession suddenly washed over Derek, thoughts of owning this tied boy below him permeating his mind. Cursing, he gripped Cory with one hand by the throat. He didn’t squeeze, didn’t make to cut off his airflow, simply held it there, held him in place. Cory whimpered as he felt the fingers tighten around his neck, reveling in the moment of ownership.
“Who do you belong to, boy?” Derek growled out between clenched teeth.
“YoOUu, sir,” Cory managed to get out between moans.
Growling again, Derek spit onto Cory’s face, making Cory moan as the spray of saliva hit him. Eyes closed, he could once again only take what his dom was giving him, and take it he did.
“Fuck, boy, I’m gonna cum,” Derek breathed into his ear, his body dropping further to cover Cory’s as he started. “Gonna fucking breed this hole.”
Derek continuously ground his hips forward, hips shaking with each shot of cum being unloaded inside of Cory’s hole. The hand around his neck had migrated to one of his wrists, and Derek’s body had collapsed on top of his, his head right next to Cory’s left ear. He could feel Derek’s breath on his cheek as his hips finally slowed and eventually stopped, the two boys now still.
After a minute, Derek lifted himself up slightly, hovering just above Cory’s face. For a moment he looked like he was going to say something... maybe even do something... but a moment later it was gone, and Derek was back on his knees, gently easing his cock out of Cory’s hole. He carefully undid both of the cuffs on his ankles, setting his legs down gently and allowing Cory to stretch them while he did the same for his wrists.
“So, what did you think, boy?” Derek was tucking away the straps under the mattress. “Good investment?”
“Great investment, sir,” Cory stretched his arms above his head. “And thank you, for the reward.”
“Like I said boy, you earned it. Keep up the good work and there will be more rewards in your future.” Cory made to get up on his own but quickly fell back to the bed, his legs feeling like jelly. Derek laughed and helped him up, allowing him to lean against him while his bambi-legs got back to normal on the way to the bathroom.
As the two cleaned up, Cory watched Derek silently. Something about him was different. Not bad. But something between them had changed. Something that meant they were becoming more than just best friends who fuck. Cory was starting to wonder if this was just about the sex anymore.
For any of them.
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