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"You've never done this before, have you?" Theo smiled, a faint hint of condescension in his tone as he buckled the clasps on the leather restraints binding Stiles' arms together behind his back. The cuffs held his arms bent, forearms bound together, elbow to wrist. Other than the leather restraints, Stiles was naked.

"Of course I have, tons of times," Stiles shot back glibly, shifting about on his knees and wiggling his fingers. His heart was pounding rapidly in his chest and he probably thought that would hide the lie. It didn't, but Theo pretended it did.

"Oh, so you're an old hand at this," Theo's said pleasantly, infusing just enough challenging skepticism into his tone to intentionally put Stiles' back up. "Get your ass spanked all the time, do you?"

Stiles' ears flushed an attractive shade of pink and Theo could smell his arousal spike along with his embarrassment. Stiles shifted about on his knees, clearly hyper aware of his nakedness and vulnerability and just as clearly deeply turned on by it.

"Yeah, sure," Stiles replied in heavily snarky and sarcastic tones. "I'm a bad, bad boy," he added, intentionally putting heat into the sardonic words.

Theo's smile widened, a warm little shiver going through his gut. The way Stiles liked to push back was already exciting him, this was going to be a lot of fun.

"Well then," Theo crouched and ran his hand teasingly across the curve of Stiles' butt, massaging the pale skin. "I guess you can take a full course, huh?" It was proving wonderfully easy to push Stiles' buttons and maneuver him exactly where he wanted him.

"Of course," Stiles scoffed predictably, then hesitated a moment as he realized he had no idea what he was agreeing to.

Theo's smile took on a predatory gleam as his hand glided around Stiles' hip and closed around his already semi-erect cock. He pumped him slowly, making the other boy inhale sharply. He doubted Stiles really knew what he was getting into when he came to him for a good time, but he'd learn.

"Yeah..." Theo breathed, steadying Stiles with a hand against his lower back as he pumped his fist more rapidly. "Yeah, I can tell you like this. Just look how ready you are," he murmured, rubbing his thumb across the head of Stiles' erection, smearing around a bead of precum. Stiles was already fully erect. "This is going to be amazing."

Stiles whined in his throat, body rocking eagerly into Theo's grip. Unsurprisingly he did not object, too caught up in pleasure and probably not wishing to seem less experienced or capable than he'd purported to be. Stiles didn't strike Theo as the type to back down from a challenge; he was too stubborn and willful. Which meant that with the proper handling, Theo was going to get to make his first spanking a truly memorable experience.

"You ready?" Theo asked, still playing with Stiles' dick. Stiles nodded instantly, breathing hard. "Okay, come on then."  Theo helped Stiles up to his feet and guided him over to the bed. He bent Stiles over the foot of the bed and tied his ankles to the legs, keeping them spread wide and ensuring that Stiles couldn't move.

Stiles' pulse rocketed up into a new bracket, his scent an appealing jumble of arousal, apprehension and excitement. He was incredibly turned on by all this, and that was good. Theo was aching to push the other boy's limits, but he wanted him to enjoy it too.

Stiles obviously expected something to start right away, but Theo made him wait and anticipate for a few minutes as he got out his toys and laid them on the bed beside Stiles. He laid out a sturdy wooden paddle and then paused a moment to consider between a thick leather strop and a thin, springy switch he'd prepped the day before.

Stiles squirmed impatiently, a bundle of anxious, aroused nerves. He twisted his head, trying to see what Theo was doing, then gulped a little when he saw what Theo was doing. "Y-you gonna use all those?" he asked, trying hard to sound casual.

Theo beamed at him. "You're right, that's the best answer," he agreed, laying both the strop and the switch down beside Stiles. "I was trying to decide which one, but we might as well just do both. I mean, I don't want this to be boring for you, right? Sounds like I've got a lot to live up to," he teased cheerfully. "I'd hate to let you down," he added more earnestly, touching Stiles' shoulder and caressing his cheek tenderly.

Stiles' eyes were adorably wide with alarm, but his scent was pure arousal. "Uh, y-yeah," he gulped, his eyes going lidded and hazy with want as he nuzzled his face into Theo's touch. "I don't ... I don't think that's gonna be a problem," he mumbled.

Theo patted Stiles' cheek and moved away again, getting out one last toy. He held the large dildo out where Stiles could see it. "Do you like to be filled while you're getting spanked?" he asked.

Stiles blinked, staring wide-eyed at the dildo. His mouth formed a small "o" and his pale, expressive skin flushed a little more hotly. The idea had obviously not fully occurred to him before but it looked as if it was doing good things for him.

"Is that a yes?" Theo asked, smiling with genuine fondness. There was something incredibly delicious in Stiles' enthusiastic lack of guile. He could like this kid. He could like him a lot.

Stiles nodded fervently against the bedspread. "Yes," his voice cracked slightly and he coughed. "Um, yeah, yes please."

Warmth running through his veins, Theo snagged a bottle of lube and squirted some onto the toy. "Okay." He slicked up the dildo and then his fingers, moving behind Stiles. He teased Stiles' hole for a minute with his thumb, then slipped two fingers into him at once.

Stiles hissed and squirmed, but his position and his bonds meant he really couldn't move around much at all as Theo carefully but methodically pumped the fingers in and out. He curled them just so and was rewarded by a little groan from Stiles. "Not too much, right?" He asked as he added a third finger.

Stiles hissed through his teeth again, but shook his head wordlessly against the mattress.

"Good." Theo patted Stiles' upturned bum with his free hand as he scissored his fingers, stretching the other boy out. After a minute he removed his fingers. Anchoring Stiles with a hand at the small of his back, he placed the head of the large plastic phallus at his entry and pushed it in. He kept the movement slow, but steady and unceasing. He hadn't prepped Stiles very much and this would probably burn a bit, but not more than Stiles could handle.

++

Stiles gasped sharply, pressing into the bed as the hard, cool shape of the dildo was forced into his body. The stretch was harsh and the toy unyielding. He squirmed, but sprawled across the bed like this with his legs immobilized and spread as wide there wasn't anywhere for him to go.

He could do nothing but take it as Theo pinned his hips down and thrust the hard, slick object deep into him with steady, inexorable force. He could do nothing, and he loved that. His gut flip-flopped and his blood burned, arousal sparking powerfully through his body and making him gasp for breath through parted lips. He was a little apprehensive about what he'd gotten himself into, but that only fed his arousal. Surrendering control was a huge turn on, but add in a hint of fear or danger and he was practically ready to cum right now. That was half of what attracted him to Theo if he were honest, the sense that there was something just a little dark and just a little fucked up under the surface.

He bit out a sharp little groan, bound hands fisting when Theo bottomed out, the long, thick length of the toy settled deeply inside him. He thought that would be it, but Theo had other plans. Before he realized what Theo was up to, Theo jerked the dildo back and thrust it in again. The abrupt motion burned and the head of the hard plastic cock rammed forcefully into Stiles' prostate, making his body spark with fire and sensation. His head jerked up and he cried out, but even as he did, Theo was doing it again.

Theo fucked him with the dildo, incredibly hard and incredibly fast. It hurt and it felt amazing. Stiles' head tossed and twisted against the bed, his back and neck arching and straining as Theo nailed his prostate over and over, leaving the area raw and throbbing and pushing Stiles to the gasping, shuddering brink of nearly coming untouched.

As abruptly as it started, it was over. Theo pushed the dildo in deep and left it there, the hard tip pressed into Stiles' now over sensitized pleasure area whilst his raw passage pulsed around the thick intrusion.

Stiles' hips stuttered and jerked as he rubbed his dick urgently against the mattress edge. He was so fucking close he couldn't stand it.

Theo's hand connected sharply with his backside, startling him and making him yelp from the suddenness and the sting. "Stop that," Theo warned, and Stiles tried, but he couldn't. He needed to cum so bad he could taste it.

Theo lifted his hips, pulling him up and back a little and getting his hands under Stiles. The brush of his fingers against Stiles' erection were electric and Stiles almost sobbed, writhing and trying to get more contact. He winced, yelping again when something supple but unyielding synched around the base of his cock, the pressure intense enough to be painful in his current state. It took his foggy mind a moment to realize what Theo had done, and by then Theo was already pushing him back flat against the mattress, his cock throbbing agonizingly between his stomach and the bed.

"No, no, no!" he whined in frustration, not caring how pathetic he sounded. "Theo! Take it off..." he chafed his body urgently against the bedspread.

++

Theo grinned wryly at the writhing boy. Stiles really had no self control or self discipline at all, he was clearly a novice at this kind of play, but Theo kind of liked that. His desperation was adorable. He slapped Stiles' other butt cheek, adding a pink hand print to it to match the other.

"You don't get to cum until the spanking is over, Stiles," he said, patient, but his tone making it clear that that should be obvious. "If I take it off, are you going to be able to manage that on your own?" He knew there was no way Stiles wouldn't be climaxing in under a minute if he took the cock ring off, but he'd let his partner figure that out on his own.

Stiles made a garbled, frustrated sound but finally stilled. "No," he muttered sullenly. 

"Okay then." Theo patted his ass appreciatively.  "We good to go?"

Stiles nodded into the mattress, still looking sulky.

Theo smiled. He'd take care of that. He warmed Stiles up with his hand, concentrating on first one cheek and then the other, slapping fast and business-like and drawing forth a faint, rosy blush. He wasn't exactly easing Stiles into it, but the young man stayed quiet and relatively relaxed. He pressed his face into the bedspread and breathed through his teeth, accepting the spanking in a way that made Theo very hot for him.

After a couple minutes Theo stopped and took a moment to massage Stiles' warming ass cheeks. "You're pretty good at this," he murmured approvingly, running his warm hands up Stiles' back and caressing circles against his sides. He meant that, he was pleasantly surprised with how well Stiles had taken the warm-up. He'd expected a lot more squirming and yelping from a first timer, especially from someone as prone to run his mouth as Stiles was.

Theo noted a distinct spike in Stiles' aroused scent at the verbal approval and leaned down to press a light kiss against his spine, making a mental note that Stiles responded well to praise. Theo didn't know him terribly well yet, but he had a good sense about people and their needs and motivations. He had an impression that Stiles needed someone to tell him he was good. Theo pressed another kiss between his shoulder blades. He could do that. Especially if Stiles was ready to be as good for him as he suspected he'd be.

"S-so are you," Stiles mumbled, voice more blissed-out than pained. "Nngh, fuck," he groaned appreciatively, rolling his body under Theo.

Theo pressed against his back and twisted his head around so he could steal a kiss from the young man's parted, eager lips. He hadn't expected Stiles to respond this well and he was thoroughly enchanted. He rocked his jean-clad hips down against Stiles' naked ones, pressing against the dildo in his ass and grinding it into him. Theo was already so hard that it kind of hurt. He wanted to lose his pants in the worst way, but not yet. Not yet.

Stiles whimpered and pushed back into him, chasing his mouth when Theo pulled away. "Fuck me, Theo," he pleaded breathlessly. "Need you inside me. God, just fuck me." He squirmed, body fairly oozing arousal and want.

Theo shuddered against his back, responding strongly to Stiles' need. He chuckled, suddenly a little breathless himself. "Trust me, I will, Stiles. But not yet. You are not nearly done with your spanking, and you're not getting out of it that easy," he teased.

Stiles groaned. "Then get fucking on with it!" he demanded. "Fuck, Theo, I'm dying here."

"What a greedy and demanding little thing you are," Theo said with a grin, deeply enjoying Stiles' unique mix of submission and aggression. "Ready for the paddle, then?" Theo asked against his skin, enjoying the little shiver that ran through his partner's body at the words.

"Yeah," Stiles breathed huskily. "Fuck, yeah."

"Hang onto that enthusiasm," Theo warned with a playful grin as he pushed back upright and picked up the paddle. "You're probably going to need it."

He swatted Stiles good and hard, enjoying the audible crack of wood on flesh. Stiles did yelp this time, reacting to the unexpected increase in sting and sensation that the paddle brought. He struggled with it the first few blows, stifling little cries into the mattress, his body tense and unconsciously trying to wriggle away from the pain.

Theo touched the small of his back again, seeking to ground him through the contact. "Breathe slower, Stiles. Don't clench, that will make it worse. Relax into it. Accept the sting, don't fight it," Theo instructed, soothing, gentle voice at odds with how ruthlessly he was smacking Stiles with the paddle.  

"F-fuck," Stiles groaned, pain definitely evident in his voice this time as he struggled to breathe deep and slow. "Easy for you to say," he muttered, although he was actually clearly attempting to follow Theo's advice. "That fucking smarts, dude."

"It's only a paddle, Stiles," Theo teased. "Been a while since your last time, has it?"

Stiles clammed up, stubbornly and predictably refusing to acknowledge that he was full of shit. "You hit hard," he mumbled defensively. His body was stiller now, though. Not relaxed exactly, but starting to accept and roll with the rhythm Theo was setting.

"I do," Theo acknowledged unapologetically. "But I think you can handle it. You're doing really good, Stiles, really good," he praised, feeling Stiles' body became slowly less ridged under his hand. He angled the paddle lower, catching Stiles across his sit spots and whacking the base of the dildo in Stiles' ass, forcing it forward in a sharp little motion.

Stiles cried out in surprise and sensation rather than pain and Theo did it again, making him pant and gasp. He kept it up, spanking Stiles everywhere, but returning regularly to jolt against the toy until Stiles was a gasping, almost sobbing wreck of stimulation, arousal and pain.

++

Stiles' ass was on fire. This was so much more than he'd expected when he'd imagined getting spanked. It hurt a hell of a lot more than he'd thought, but it also felt much more incredible.

Stiles clamped his lips together, rubbing his head feverishly against the bedspread and whimpering in his throat as Theo moved down to paddle his thighs. Ow, ow, ow, ow!!!! He wanted to cry out and whine but tried to keep quiet. Theo acted like this should be no big deal and he didn't want to come across as a big whiner baby loser. He had very literally asked for this, after all.

He'd been interested in trying something a little edgier for a while, but hadn't been sure where to start. Then he'd seen Theo a night club when he was out with friends. He'd been instantly attracted, but when Danny (who seemed to know everything about everybody) saw who he was eyeing and made a casual remark about the kind of stuff Theo was purported to be into, Stiles' had made it his absolute mission to try to hook up with the hot stranger.

Honestly, he'd been surprised Theo had given him the time of day. Stiles did not usually have great luck with guys, but Theo had been receptive to his fumbling attempts at flirtation and after a few dances and a few more drinks, they'd ended up having deliriously rough, urgent sex in the club's bathroom. Afterwards, afraid that this was just club sex for Theo and he wasn't going to see him again, Stiles had blurted out in the most awkward way possible that he wanted Theo to "spank him and stuff". In his defense, he had been rather drunk at the time and that had been the only thing that came to mind.

Theo had not laughed at him, thank god. Instead he'd taken Stiles' phone and entered in his number, telling Stiles that if he still wanted it when he was sober, to give him a ring. Stiles had, and they'd ended up here, with Stiles trussed up and bent over Theo's bed, his ass flaming and his dick so hard and hot he almost couldn't stand it. 

Theo just kept paddling him and paddling him and the mind bending mix of pleasure and pain became increasingly intense. Stiles didn't know how this worked. He didn't know how long this was going to go on, or how he was going to take it as the burn grew, and grew. The uncertainty tied his stomach in pleasurable, agonizing knots.

He did know he could tap out if he really needed to; Theo had made sure he picked a safe word and all that, but Stiles had promised himself he wasn't going to use it. How pathetic would that be? Asking for this and then wimping out? Nope. He was not humiliating himself like that in front of Theo. They hadn't really discussed anything beyond this exchange, maybe this was all Theo was going to want, but Stiles hoped not. He was crazy attracted to the other boy and he kind of really wanted to keep seeing him. He wanted to have a chance with Theo and not make a bad impression or prove himself unworthy of interest. He had the vague hope that if he did good tonight, Theo might want more.

So Stiles bit down on the bedspread and surrendered himself to Theo, freely taking anything he chose to give him. He breathed shaky but deep, struggling to relax and accept the overwhelming dual sensations throbbing through him. He groaned, almost sobbing every time a blow made him clench around the hard plug inside him, or sent it jabbing forward, digging into his raw prostate.

He scrubbed himself in needy, agonized little jerks against the mattress, moving in time with the spanking. He was so aroused he could barely think straight. He felt like he would have cum a dozen times over if the cock ring weren't keeping him from being able to find that release. Constantly riding the edge like this with no relief in sight was a horrible, blissful kind of torture.

The more fully Stiles submitted and accepted the punishing rhythm, the better it felt. Not that it didn't still hurt, it did, but it was in some way like violently scratching a bad bug bite. It hurt, but in the moment you were doing it, something about it also felt unbelievably good and you just wanted to scratch it harder and harder and never stop.

"Theo," he gasped, almost sobbing into the mattress, just needing to say something and that seeming to be the only sensible thing he could manage. "Oh, God, Theo...!"

++

Theo's heart pounded deliciously, his insides tightening and churning hotly as Stiles groaned his name like a plea, but not a plea for reprieve. He caressed Stiles' back, paddling as hard as he could and focusing on turning every inch of Stiles' butt and thighs as deeply red as possible.

"So good, Stiles. Doing so good, fucking amazing," he murmured, the praise genuine rather than calculated this time. He'd meant to push Stiles, to show the cute, awkwardly eager young man the good time he'd come looking for and then some, but he'd never expected him to take it this well or be so receptive. He'd pegged Stiles as a stubborn one, certainly, but having high endurance was one thing, falling so beautifully and readily into something akin to subspace was another.  

He was paddling Stiles a lot worse than he'd intended, probably a lot worse than he should on his first time, but Stiles took it so beautifully and was so intensely, almost mindlessly aroused, it kind of took Theo's breath away and made him want to just wreck him. He usually stayed a little more detached than this when he was playing, but something about Stiles sucked him in like a black hole.

He finally forced himself to stop, taking his own advice and drawing deep, slow breaths to clear his head. Stiles was squirming and groaning on the bed, desperately aroused and seeming almost distressed by the cessation of contact as he had been by the blistering application of the paddle.

"Theo!" he practically sobbed. "Theo, please..."

Fuck it. Theo tugged his shirt off over his head. He needed to be naked, now. He needed to feel that amazingly flushed, desperately twitching skin beneath him. Stripping, Theo slid between Stiles legs, bending across his back and molding their bodies together. He inhaled, savoring the heat radiating off of Stiles' abused ass and thighs and the way the other boy whimpered and tried press back into him.

"Fuck me, fuck me, fuck me," Stiles begged breathlessly, his voice horse and shaky from tears Theo hadn't noticed before. "Please, Theo, please," he sobbed.

Theo rocked against his hips, his erect cock sliding and dragging deliciously against Stiles' hot ass. "Shh," he soothed, kissing Stiles' shoulders and neck. He reached around and wiped tears from Stiles' flushed cheeks. Pulling Stiles' head up and around gently, he leaned down and kissed his mouth tenderly. Stiles' lips were flushed and swollen from how hard he'd been biting them and Theo sucked them lightly. "Shh, not until we're done," he murmured.

Stiles sobbed a little harder.

"You need a break, Stiles?" Theo murmured. Stiles vehemently shook his head. Theo kissed his ear. "I kind of think you do. I worked you pretty hard, babe. Let's give it a chance to settle. Shh, no, it's okay, trust me, all right?" he soothed, sliding back off of Stiles' body. He manipulated the exposed plug of the dildo inside Stiles until he found the flat press button he was looking for.

Stiles keened, body jolting when Theo turned the vibrator function on. Theo kept it on low, knowing Stiles was already fairly over stimulated and wanting it to be pleasant, not painful.  Well, okay, not too painful.

Theo crawled up on the bed by Stiles' head. He caressed his hair and then lifted his head and shoulders, propping him up a little. Stiles' flushed, tear streaked face was slack, almost looking drugged with pleasure, but his eyes were animated with urgent need. He looked wild and Theo thought he was absolutely gorgeous like that.

He caressed Stiles' cheek adoringly and then nudged his very aroused dick towards Stiles' flushed lips. "How about you suck me off while I let you cool down, then we can continue?" he coaxed.

Stiles licked his lips, mouthing Theo's cock eagerly enough, but he frowned a little. "Want you to fuck me," he mumbled somewhat petulantly.

Theo grinned and bent down to kiss his forehead. "You have a one-track mind, and I'm not complaining. Don't worry, Stiles, I intend to fill your mouth and your ass with my cum, and I've plenty to go around, trust me."

Stiles shivered in response, his eyes glazing a little more. He was really gone and Theo was beyond enchanted. He steadied Stiles' head, guiding his dick into the wonderfully hot, wet mouth.

Stiles went down on him hesitantly but willingly, bobbing his head as much as the awkward position allowed and eventually letting Theo hold him and just fuck into his mouth. He choked and spluttered a little, gagging when Theo pushed down his throat, but did an admirable job of swallowing around him and rolling with it. Theo had let himself get so worked up that it wasn't long before he was spilling down the boy's throat, sighing in relief and contentedly watching jizz dribble from the corners of Stiles' mouth as he gulped and gasped for air.

"Okay?" Theo asked, caressing Stiles' hair again as he leaned back, allowing himself a minute to enjoy the afterglow as he regarded the lovely body sprawled in front of him. Stiles was quite the picture of perfection: cum smearing his lips, his hair wildly mussed, his arms and legs bound, ass spanked red, trembling body squirming about on the bed as the vibrator buzzed away inside him.

Stiles nodded vaguely although he still looked near tears.

"You're beautiful," Theo murmured, feeling an strong, unexpected desire to keep the human forever. Or at least for a while.

Stiles blinked at him, clearly surprised and more pleased than he wanted to let on. That mustn't be something he heard much, which was a shame because really, it was true. Theo found him especially beautiful like this, all wrecked and spread out for his pleasure, but Stiles was objectively quite attractive under any circumstance.

"I had no idea you'd be so good," Theo murmured, still petting and caressing Stiles' head and shoulders. "If I had, I would have dragged you home from the club that night and had my way with you then..." he teased before sighing and sliding off the bed. "Well, shall we move on to the strop now, Stiles?" he asked pleasantly. Now that he'd taken the edge off his own need, he'd be able to devote proper attention to punishing Stiles' cute red ass like it deserved.

Stiles groaned, his voice even hoarser now, although his body had calmed a little during the break. "Theo, it ... it really kind of hurts," he mumbled.

"I know," Theo commiserated, touching his ass soothingly. "I'll leave the vibrator on, okay? That'll feel nice." Stiles knew how to safe word out if he wanted to. Admittedly, Theo suspected that by this point Stiles was too gone to do so ... but that wasn’t exactly his problem, was it? It was all right, he'd make it good for him; he liked Stiles, after all.  

++

Stiles wailed, all notions of staying quiet flying out the window when the strop cut down across his already raw backside. He clenched around the vibrating object inside him, conflicting sensations making his head spin. The thick leather strap stung like mad, drawing ribbons of fire across his skin as Theo strapped him. He started at the top of Stiles' butt and then worked his way slowly and relentlessly all the way down to just above the back of his knees.

The way Stiles' legs were spread meant Theo had to take each leg individually. The strop's short tail bit into the inside of his thighs as it landed, making his breath explode over and over in sobbing cries. Stiles' knees would have buckled if he wasn't already flopped helplessly across the bed.  The buzzing of the vibrator inside him was almost painful in its own right by now, his passage oversensitive and raw, his need to find orgasm a crazy, burning craving that felt like it was going to drive him totally mad.

He was half out of his mind with pleasure, but the pain was blinding and unbearable. He wanted to take it, but he couldn't. When Theo started over again at the top of his butt, he broke.

"No, Theo, Theo, I can't! It hurts, I can't!" he sobbed. It took his addled mind a minute to remember that that wasn't the right thing to say to make Theo stop. He didn't want to disappoint Theo, but he was hitting his limits and was sorely tempted to break his promise to himself to not safeword out.

"Shh, it's okay, I know, you're doing great," Theo encouraged, still whipping him. "One more pass, Stiles, last one, promise," he coaxed. "You can take it. You're so good at this, Stiles. I know you can."

Stiles pressed his face into the mattress and screamed into the bedspread, his throat ached from the recent fucking and all the yelling was doing him no favors, but he couldn't help it. He clenched his eyes shut, tears leaking down his face and told himself he could do this. One more pass wasn't so bad. He could handle that. He could. It helped a lot knowing when the end would be and exactly how much he had to take to get there.

He was shaking and sobbing harshly by the time Theo finished. God, he was never going to be able to sit again! Stiles collapsed limply on the bed, struggling to breathe and by now fervently hating the vibrator in his ass. He was so damn raw and yet it wasn't enough. He felt like one giant, exposed nerve.

The brush of something cool and thin against the back of his throbbing thigh made Stiles stiffen. He struggled to look over his shoulder and saw Theo standing behind him with the switch. He shook his head urgently, his gut flipping agonizingly as he realized they weren't actually done yet. He really, truly didn't think he could take any more.

"N-no, Theo, no more..." he pleaded plaintively, his whole body tensing and starting to struggle in his bonds.

"It's okay," Theo soothed. "Almost done, Stiles. You're super red, babe, I know you've got to be sore. We'll just do five and call it enough, huh?" He rubbed Stiles' back gently. "Five with the switch, and then I'll fuck you. How's that sound?" he murmured with a smile.

Stiles whined in his throat, but ... it was only five. How bad could that be? He was too close to the end to give up now. "O-okay," he mumbled, voice hoarse. "And then we're done, and you'll fuck me and I get to cum," he stipulated in a shaky rush. "Promise?"

Theo chuckled fondly and squeezed his incredibly sore butt. "Yes, Stiles, I promise," he agreed. "You've been so good, and good boys get rewarded."

Stiles didn't necessarily want to feel so affected by Theo's praise, especially when he knew he was sort of teasing, but he was so raw and vulnerable right now, it was like warm water on sore muscles and it soothed him a little.

"Count them this time, all right?" Theo said, putting his hand at the small of Stiles' back again, grounding him for the last set. That proved to be a good thing, because as it turned out, five could be very bad.

Stiles screamed, totally unprepared for the blistering cut of the switch across his abused skin. He didn't think getting stuck with a hot poker or maybe even getting shot could possibly hurt that bad. He lay there gasping and in shock for a moment afterwards, stunned by the way the burn just kept going, arms twisting in their bindings with the desperate need to rub the sting away. It took him a minute to process the fact that Theo was speaking to him, reminding him to count.

"O-one," he stuttered, still gasping.

Two made him scream just as hard, by four he was sobbing almost hysterically and he barely managed to choke out something that sounded vaguely like a number. He counted five very clearly though. "Five!  Five! Fucking five, Theo, five!" he said urgently, really wanting to make sure that Theo was aware of the number. There was a shaky triumph in his tone too. Hey, he was pretty damn proud of himself for making it through that.

"Got it, Stiles," Theo said, the smile evident in his voice. He tossed the switch aside and yanked the dildo out of Stiles' ass.

Stiles whimpered, glad to have the damn thing gone, but now feeling horribly empty. He'd never needed to cum so damn bad in his life. "Done?" he asked, voice still shaking with sobs.

"Yes, all done," Theo reassured, caressing his body hungrily as he pressed up against his back. His body actually felt cool against Stiles' blazing rear, but the hard shape of Theo's dick digging into his thigh was hot and heavy. "It's over. Gonna fuck you now. Gonna fuck you until you scream for me," he promised. "Gonna make you cum until you can't anymore."

Stiles panted, messy with tears and snot, his confused body still trying to stop sobbing even as his insides trembled with hungry fire. "Yes," he groaned, sniffing. "Yes, yes, yes..."

Theo thrust into him and Stiles curled against the bed, giving a muffled cry at the sensation. He was incredibly tender inside from the vibrator and his ass throbbed painfully every time Theo pressed into him. It seemed like every nerve ending he possessed was inflamed, alive, and sparking with sensation. It made everything a hundred times more intense as Theo firmly and demandingly fucked him into the mattress.

Stiles was still tied down and he could do little more than pant for breath and cry out as he was fucked hard. Theo grabbed onto his bound arms, using them as leverage to pull Stiles back onto him even more forcefully as he rabbited his hips into him.

Stiles wailed, begging for more, shaking with ecstasy that seemed too big and too explosive for his body to contain. Pleasure shocked through him in trembling spasms and jerks. Theo hadn't taken the cock ring off him yet, but the sensations rocked through his gut like a dry orgasm, or some kind of orgasmic precursor that he'd not experienced before, shocking him.

A few seconds later, Theo groped under him, tugging the ring off and holding him in his fist as he came inside Stiles' body. That was all Stiles needed to prompt him to immediately come a second time, or perhaps complete what had already started, he wasn't quite sure at that point. Everything was just sensation and ecstasy and exhilaration. He was sure that all hyperbole aside, was the most intense orgasm he'd ever experienced. He came hard all over the bedspread, body shaking and twisting in Theo's arms as waves and shocks of sensation burned and jolted through him.

He wasn't really aware that Theo had also climaxed until his own started to fade and he became aware that Theo was laying against his back and there was moisture trickling down the inside of his thigh. Theo was still inside him and still hard, stamina that Stiles appreciated at this moment because the fullness felt good as his body fluttered and pulsed with flickering aftershocks, the gentle little thrusting motions of Theo's hips feeling almost soothing and drawing out his pleasure deliciously.

They stayed like that for several long minutes, Theo kissing Stiles' back gently and rocking inside his shuddering body until Stiles' wild, ragged breathing finally calmed and his tears dried. It felt incredibly intimate, even though he couldn't touch Theo back. The intensity of what he'd given Theo just now left him feeling very vulnerable but also deeply connected to the other boy.

Theo was all gentle touches and soft, praising words and Stiles relaxed into him, savoring the strangely floaty and surreal sensations. "That was... that was really good," Stiles mumbled blearily, his voice wrecked. He hummed softly in his throat, groaning a little as Theo's soft touch and the gentle pressure of his body kicked up new fingers of pleasure inside his quaking frame.

"It was," Theo agreed, finally withdrawing so he could untie Stiles.

Stiles frowned at the loss, feeling suddenly very empty and alone without Theo's body against his. He shivered, feeling cold as Theo freed his legs and carefully unbuckled his arms. His backside was starting to remind him how very badly it hurt and he hissed, biting his lip as Theo guided him up onto the bed.

Theo carefully rubbed circulation back into his arms and got him to drink a bottle of water and eat some chocolate, which made him feel a little better, but he was still cold and empty and not emotionally ready for this to be over.

Thankfully, it wasn't. After giving him the chocolate, Theo crawled onto the bed with Stiles and curled around him. Stiles wrapped his arms around him and tangled their legs together, settled into the other boy's embrace with an embarrassing amount of relief. He wasn't used to these sensations and he needed to be held.

Theo seemed to get that. He cuddled Stiles contentedly, gently rubbing his sore ass, trading long, deep kisses and stroking their cocks together in slow, unhurried motions that kept the fires burning in Stiles' gut. By the time Stiles realized he would rather like there to be a round two, Theo seemed to have already reached the same conclusion.

He rolled Stiles over onto his back, but that was a rather problematic position for Stiles right now. His ass felt burned and putting pressure on it was like sitting on a live griddle.

"Ow, ow, fuck," he groaned, pushing Theo off him and quickly rolling onto his side again. "Fuck it, Theo, I'm not gonna be able to sit tomorrow," he complained hoarsely.  "How the hell am I gonna make it through class?" This had only just now occurred to him and it was not a pleasant thought.

"We'll ice it tonight and it won't be quite as bad tomorrow," Theo reassured, pulling Stiles back to him and rolling them over so that he was on his back instead with Stiles straddling him. "Tell me when and where your classes are, and I'll bring you fresh ice packs and rub it out for you when you're on break, if you want," he offered, his gaze lidded.

Stiles shuddered against him. He liked the sound of that. A lot. He also liked the intimation that Theo was interested in continued contact.

Moving stiffly because his abused muscles were shaking and his whole body felt exhausted, Stiles guided himself carefully down onto Theo's dick. He hummed in his throat, forehead falling to Theo's shoulder. He ached fiercely inside, but Theo felt good there, like scratching an itch, and it distracted him from the throbbing mass of pain that was his butt.

"Yeah, I think I'd like that," he responded hoarsely. He was almost too tired to effectively ride Theo's dick, but Theo took hold of his hips and helped guide him through the motions, their mouths and tongues dancing and tangling as they fucked more slowly this time.

"Maybe later we could grab dinner or something," Stiles suggested, speaking quickly before he talked himself out of it.

Theo smiled up at him, cocking an eyebrow. "Like a date?" he queried with a touch of amusement.

Stiles flushed a little more and worked himself harder against Theo's dick, his own digging hungrily into Theo's stomach. He didn't want to be that person that tried to force more out of a causal hookup than was supposed to be there. "I mean, like food because even total jerks have to eat, right?" he mumbled, retreating into sarcasm.

Theo chuckled and caught Stiles' face between his hands. He kissed him lightly on the lips. "Dinner sounds good, Stiles. Let's do it. We can order in, watch the game and ... maybe some other stuff?" he suggested, eyes twinkling.

Stiles relaxed and smiled back. "Yeah, okay, that sounds good," he agreed.  His thighs were shaking and his muscles burning. He groaned and rolled off Theo. Going to his elbows and knees, he rested his head on his arms and spread his legs invitingly. "Now quit making me do all the work and just fuck me, would you? I'm tired, you wore me out."

Theo smiled and very readily obliged. "I think I could get used to you, Stiles," he mused contentedly as he sank back into the proffered body, tenderly stroking Stiles' reddened, welted thighs.

"I grow on people," Stiles agreed with self-satisfied contentment, settling down with a happy sigh as Theo took over fucking him and stroking his dick. "Like ..." his soggy mind looked for and failed to find a suitable comparison. "Like awesome mold," he finished contentedly.

++

Theo laughed. "Well, I'll buy the awesome part," he agreed, caressing Stiles' flesh and savoring the sensations as he pressed in and out of his gripping heat.  He hadn't been looking for anything more than a distraction, but he was willing to consider changing his mind about that for Stiles. It seemed, they might both have found a little more than they expected tonight.

 

FIN