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Summary:

It started off as dirty talk. Stiles had three fingers in Derek's ass, stretching him nice and good, taking his own pleasure from the whimpers that Derek let out every time Stiles' long fingers slipped over his prostate. He wondered aloud what it'd be like to watch Derek fall apart just from that. He told Derek he'd get him a vibrating plug, make him wear it one day. But Stiles would be in control of the remote. Would turn it on whenever he felt like it. It could be when Derek was getting groceries, or at work in a meeting, Stiles didn't care. With the werewolf refractory period, he could turn it on every half hour if he wanted to until Derek's stomach cramped from coming so much.

That's about as far as that conversation got before Derek flipped Stiles on his back and rode himself to two orgasms before Stiles reached his first.

Notes:

This is because from three things.

1) A desire to write and finish something.
2) This post on Tumblr that I found.
3) And most importantly, talking with Brii on Twitter about uncut dicks and Stiles salivating over it.

Mash all three of those together and you get this!

I've also added this as a series 'cause there's the potential that I could expand on this. I have like, three other bottom!Derek ideas that I'll probably submerse myself in over the next few weeks.

(See the end of the work for more notes.)

Work Text:

It started off as dirty talk. Stiles had three fingers in Derek's ass, stretching him nice and good, taking his own pleasure from the whimpers that Derek let out every time Stiles' long fingers slipped over his prostate. He wondered aloud what it'd be like to watch Derek fall apart just from that. He told Derek he'd get him a vibrating plug, make him wear it one day. But Stiles would be in control of the remote. Would turn it on whenever he felt like it. It could be when Derek was getting groceries, or at work in a meeting, Stiles didn't care. With the werewolf refractory period, he could turn it on every half hour if he wanted to until Derek's stomach cramped from coming so much.

That's about as far as that conversation got before Derek flipped Stiles on his back and rode himself to two orgasms before Stiles reached his first.

He forgot about it for a couple of weeks until Stiles showed up at the loft with a package. They went through their usual banter about why Derek still lived in the loft six years later ("Because, Stiles, the closest neighbor is four stories down. They can't hear any screaming from in here; any."). That usually led to mutual handjobs against the closest surface to take the edge off and test the sound barrier.

That day, instead of heading to the couch or bed like normal, Stiles went back over to grab the package where he'd dropped it. It was unassuming, standard brown box with a white shipping label, but the smile on Stiles' face was the opposite of unassuming. Especially when he let Derek know that it was a present for him. His smile was pleased with an edge of predatory.

Long since over the days of fear that it was a wolfsbane bomb or some sort of ill thought through prank, Derek just popped out a claw to rip into the box. There was bubble wrap, a packing slip, an instruction sheet, and then a little silk pouch.

It was inside.

"What's this?" Derek questioned, his pulse thrumming hard. He knew exactly what it was.

"A vibrating butt plug." Stiles smirked, fingers curling into the waistband of Derek's jeans. "For you."

Derek's dick filled quickly between the open zipper of his jeans. "Let's go try it."

Stiles made a protesting sound. "This," he snatched the remote control from Derek's hand, "is mine. And the plug is yours, but for tomorrow."

"I have to work tomorrow, we won't have time in the morning." Derek protested, even as snippets of the conversation from weeks prior started to drift back.

"We'll have time to put it in in the morning." Stiles sucked a soft kiss into his jaw, hand slowly starting to play with the foreskin on Derek's cock, "Then you're going to wear it all day tomorrow and I'm going to turn it on whenever I want to. Do you want to do that?"

"Fuck." Derek hissed. He had errands to run, work, a meeting possibly. Stiles having control of the remote meant he very well might have a vibrating plug up his ass, pressing against his prostate, milking him to orgasm at Stiles' whim, while talking to his boss about the plans for the new apartment buildings downtown, or at lunch with Kyle. "Yes."

So that found him the next morning with Stiles painstakingly preparing him. Fingering lube into him while his lips pulled and played with his foreskin, tongue dipping in to lap at the precome leaking from the slit.

"Your first orgasm is mine." Stiles commanded, jacking the base of Derek, "Down my throat. I'm not going to turn on the plug yet, though. That's for when you least expect it."

Derek whimpered, fists clutched the sheets when Stiles took him into his mouth. Stiles claimed his biggest kink was Derek's dick. Uncut, long, thick, copious amounts of come to paint him with; perfect he claimed. But Derek knew better. It was this. Control. Control he took from Derek readily as he swallowed with a moan, his eyes rolling into his head while Derek splashed in his mouth the same time the plug slid itself home.

Now, he's five hours into his day with the plug in his ass, and not so much as a hum from it. Stiles has been uncharacteristically quiet. It feels good, though. A soft thrum of pleasure steady throughout his body. He's permanently at half mast, aching to rock his hips for a little more stimulation from the plug. It's been distracting him all morning.

Nearly lunch now, he just wants to go into the bathroom and stroke one out. But he knows that's not the point of this. If he takes the pleasure himself, it'll be selfish. Stiles is trusting him to wait, trusting Derek to trust him to bring Derek pleasure. That's always important to Stiles; Derek's pleasure, Derek's satisfaction.

"You okay, Hale? You look a little clammy." His co-worker pokes his head in. Derek wonders what he'd think to know that the man he's talking to has a plug shoved up his ass while his partner holds the key to him potentially shooting off in the middle of their conversation.

"Fine. Just heading to lunch with a friend." Derek stands gingerly, inhaling slowly as the plug adjusts within him. Fucking God, he just wants to rut against something. He makes sure his leather jacket casually covers his groin. Thank God for casual Fridays.

The co-worker reminds him of some inane shit, things that Derek's tuning out because fucking hell the plug feels so much more pleasurable than he remembers it being as he made his journey from his house to the office. Standing tall makes it fit snugger inside, his ass clenching down around it. He has to swallow the whimpers he so desperately wants to release from the sensation.

When he's alone in the elevator, he allows himself to though. Allows himself to flatten up against the back of the elevator and roll his hips. He rolls his neck and shoulders too for the camera's sake, to make it seem like he's just loosening tight limbs.

He hasn't been tight in hours, though.

He's been loose and pliable around the plug, wishing for just a little more friction. Maybe next time, he can shop with Stiles and get a ribbed one.

He has no idea how he's supposed to make it through lunch with Kyle. Even though he's not a werewolf, Kyle Parrish had been let in on it during Stiles' senior year of high school after the umpteenth incident at the department. Luckily, the man won't be able to smell how fucking turned on Derek is, but he probably won't be happy with the company either seeing as Derek doesn't think he could hold a conversation without becoming a whimpering mess at some point.

He's halfway to the diner when it finally happens.

And it's not gradual. Or even a slow setting.

It's full. Fucking. Blast.

He jerks his car off the side of the road suddenly, the person behind him honking angrily. He doesn't even hear it though, 'cause he's too busy moaning.

Derek has enough sense to put the car in drive, undo his seat belt, and slide his seat back as far as it'll go so he can stretch his legs out. He's reaching for his zipper when his phone rings and the car's bluetooth tells him that it's Stiles.

With a shaky finger, he presses this screen to pick up the phone.

"Fuck," is his groaned hello.

"This isn't even the highest setting." Stiles responds with, like they're already in the middle of a conversation. It almost feels like they are, like this has been one long conversation all day.

"God, Stiles, please." If Stiles wants him to beg, he will. Because it's fucking amazing. It's a live wire and he can feel his dick leaking in his pants, smell himself through the materials that he's soaking. He drags his fingers across his nipples, catching on his shirt, throws his head back and shamelessly moans.

"You wanna come?" Stiles asks casually, voice filling the car.

Derek can hear the hitch in his breath though, can hear the slide of skin through the connection. "Are you jerking off?" The thought of Stiles getting off solely because Derek's in so much pleasure sends his hips into the air, ass clenching around the vibrations to make sure it doesn't pop out. It's unlikely, but he'll probably cry if it did. But his dick his pressing against the wet material encasing him, feels the slightest bit of friction and chafing, but it's something and it feels so fucking good.

"Of course. I can just imagine you, sitting somewhere, sweating, fucking the air 'cause you won't touch yourself. I know you won't, 'cause you want to see it too, don't you?"

"See what?"

"How hard you can come untouched." Stiles' moan is lewd, vibrates through the bones of the car and deep into Derek's own. "I wonder how wet you are."

"Oh, God. It feels so good." Suddenly, the vibration pattern changes. Instead of one continuous buzz, it starts to pulse, drumming against his prostate. "Fuck!" His hips jack into the air again, dick edging against the steering wheel. He wants to grab hold of it and mount it, fuck into the horn just for something.

Stiles whines softly, a shuddering gasp followed by a soft groan. Derek can see him in his mind, splayed out naked somewhere, come splashing his chest. "Fuck, yes. God, Derek. Next time I plug you, I'll do it with my come still fresh inside you. Keep it in there to keep you nice and wet for when I fuck you again."

Derek shouts, coming in his pants untouched. His dick pulses and twitches, emptying in over half a dozen shots while the vibrations taper off.

"Shit."

"There are extra clothes in the back seat. Have fun at lunch with Kyle." Derek both loves and hates him for how unaffected Stiles sounds as he disconnects the call while he's still shaking.

The next few hours were spent sensitive after an orgasm and with the plug still in him, but tolerable. Lunch was a little uncomfortable so soon after, and he was sweating through his meeting, but Stiles knew what time that was, knew how important it was, so he didn't fuck with Derek then.

There was an instance where he'd turn it on low for a few minutes and then turn it off. Derek would get a text a few seconds afterwards telling him it was just a reminder. Like he could fucking forget. He knew that when he took the plug out, he'd be gaping and ready for Stiles to fuck him, come in him, that's what he wanted most from all of this. It's one of his favorite things. To have Stiles' come marking him, inside and out as it drips, reach around and shove it back in with his fingers, clench around it so it stayed.

With a plug now, it'll be so much easier. He's not sure why they never got one before now. They've been together for two years, after all.

He got a little complacent though, thinking that perhaps Stiles was only going to milk a singular orgasm from him until they were together. It was a disappointing thought, but being around the pack, he felt relief.

Weekly dinners were a thing Scott enforced. Derek was last to arrive; Stiles was already there, along with Isaac, Lydia, Allison, and Kira. Danny was away at a conference, Kyle had the late shift so that the Sheriff could go on a date with Lydia's mother, Susan.

He should've known from the moment that Stiles insisted they play some music that he wasn't going to get a reprieve in this situation.

Small talk was being had, each talking about their careers--Allison put her tracking and hunting to good use and became a cop; Scott shocked absolutely nobody when he went into veterinary medicine; Isaac got his tough guy act together and became a social worker; Kira opened and ran the only comic book store within a seventy mile radius which made it pretty popular, she also was the sole stocker of a comic book series about werewolves, kanimas, banshees, and kitsunes that Stiles wrote and Kyle drew under assumed aliases; and Lydia did whatever the hell she felt like doing at any given time, which last he heard was overhauling Beacon Hills' education system for fun--when the first thrum went through him.

When he regains his posture, Derek chances a glance at Stiles. He's laughing and smiling with Kira, talking about the next issue of the comic, looking completely innocent. But his hand is idle in his pocket and Derek knows that's where the control is.

"Are you alright, Derek?"

"I'm fine." He grits out at Scott, feeling guilty instantly because, for all intents and purposes despite getting Alpha status back several years prior, Scott's still like an Alpha to him. "I just had a questionable lunch. I think I need to use the bathroom."

He's barely shut the door when the volume jacks up again and he thanks fuck that Scott, like all the werewolves, has soundproofed certain rooms in this house; including the bathroom. Because the moan he releases, his hand knocking personal items around as it scrabbles for purchase on the counter, is sure to bring attention otherwise.

God, he wants to touch himself. Wants to get his hand around his cock and squeeze, strip himself hard and fast until he shoots all over himself. Wants to go back out and drag Stiles in, shove him to his knees and tug himself off over those lips, paint his face until he's covered.

He just wants Stiles. The thought's barely through his head when the plug slows itself to a stop, leaving him panting and unsatisfied. At first, he's thinking it's another reminder, but then the doorknob jiggles and there's a quick succession of knocks that he and Stiles came up with when they would sneak off for quickies early in their relationship.

He nearly takes the door off its hinges in order to yank it open, drag Stiles in, and shut it one more time.

"You son of a bitch." Derek growls, before messily slotting his mouth over Stiles'. He gets more teeth and hot breath than mouth due to Stiles laughing. "You think this is funny?" He bites meanly at Stiles' mouth, "I've been fucking leaking for you all day."

Stiles moans happily, "You have two options. No more plug 'til we get home or I turn it back on and you come down my throat. Option two has the bonus of no one knowing when we go back down for dinner, charades, and then we can go home and I'll fuck you through the mattress until you're a sobbing, soaking wet mess."

It's takes less than three seconds for Derek to simultaneously shove Stiles to his knees and pull out his dick. When he looks, Stiles has the control in one hand and his mouth open and ready. His head brushes over red lips, just a tease for both of them.

Derek pauses for a moment, taking in the picture Stiles paints. Eyes blown, cheeks flushes, mouth wet with a string of precome clinging to it. Even though he has the control in many ways, he still looks so eager to please. He's perfect.

He's anticipating the plug amping up, abusing his prostate once more, as soon as the head of his cock passes through Stiles' lips. He swirls his tongue around the head, wiggling under the foreskin to soak him in and out. The double stimulation has him sagging forward into this wall, forehead resting on it while he looks down at Stiles who decides to twist the plug at the same time he deep throats Derek.

The vibrations, the sudden push and pull of the plug fucking into him, the head of his cock pushing into Stiles' throat. That's it. He's done. The orgasm rips from him, his shout loud and stuttering like his hips while he fucks himself into Stiles' mouth and through the waves of pleasure. Stiles moans around it, holding himself stationary as Derek uses his mouth, floods it.

He's not sure how much more he can take. He's just edging into oversensitive when Stiles abruptly shuts off the plug and pulls off of him. He feels a bit weak from that orgasm and lets himself just sink to his knees around Stiles.

Derek knows Stiles didn't come, can't smell anything from him and he hates it. He wants to strip Stiles clean of clothes, eat his ass until he's begging, fuck him through a orgasm to hold them over 'til they get home and Stiles can repay the favor. But everyone will smell it. They're probably already suspicious with how long Stiles has been up there.

"You ate something bad at lunch, we're going home so you can sleep it off." Stiles tells him softly, stroking Derek's jaw and peppering kisses here and there. "I need to come and I want to be inside you when I do. I've been fucking edging myself all day waiting for this."

"Shit." This time, the kiss hits the mark. And all it does is leave him wanting more of Stiles. He's fucking addicted to the way Stiles touches him like he's everything he ever wanted in the world, looks at him like he's the only person, loves him like he needs to to breathe. He turns the bruising kiss into something tender; soft, sucking kisses as he talks himself into pulling away. He needs to tuck himself away, fix his clothes before they go downstairs. "I love you."

Stiles looks surprised, but smiles happily. Derek, despite his progress, still has some issues saying it. Stiles can say it so freely, and Derek admires him for that, but it's hard for him. Yet, Stiles makes it easy, too.

"I love you, too." Stiles responds, pressing one more solid kiss to Derek's mouth. "Now let's go home."

The lie, though met with some knowing smirks, goes over and they're on their way home before Derek can really register it. He's tense on the car ride, glancing over at Stiles. "Let's put a pause on this 'til we get home. I don't feel like killing either of us because you decide to test the highest setting."

"I know. It's only a ten minute drive, I can control myself." He smirks at the word choice.

Just barely. They manage to make it into the elevator before Stiles is rutting against his ass, bumping the plug in further. Derek's hands splay out on the elevator wall, pushing back into Stiles. There's a low pulse from the plug as Stiles puts it on a steady low setting.

"I feel like we should try to break the record tonight." Stiles breathes into Derek's ear, grasping the heft of full cock through Derek's pants. He chuckles lowly when Derek whimpers.

The "record" is how quickly Derek can come a second time. Being a werewolf has perks. Coupling the right stimulation with his healing factor, Derek can have multiple orgasms. His record is four minutes and twenty two seconds between first and second orgasm. (Stiles still hasn't worked out the science of that, and probably never will, but he enjoys testing it.)

Though, Derek's already worked three out in a twelve hour period. Hitting five would be ambitious.

"I want to come inside of you, but this is about you. Is that where you want me to come? Do you want me to come on your stomach after you've already painted it? Or your back? Maybe across your hole and then work it into you before I go soft? Your mouth? Where do you want me, Der?"

"Inside me." He groans, grabbing Stiles and dragging him to the loft doors when the elevator finally fucking stops. "Need you to come inside of me. I've needed it all day."

They don't even make it the extra ten feet to the bed. Stiles has Derek bent over the couch, pants around his ankles, plug on a steady medium speed.

"You look so fucking good like this. You've been so good all day; taking what I gave you like such a good boy." His hands skirt across Derek's back, stroking him while he praises.

Derek feels his dick twitch, looks down to see the precome dripping to the floor. There's a small puddle there the size of a half dollar. He's so fucking turned on but it still doesn't feel like enough. He needs the plug out of him, needs Stiles in him; real, warm, solid.

"Please, Stiles."

"Please, what?" Stiles questions, even though he knows what Derek wants.

"Fuck me. Take the plug out and fuck me."

"As you wish." Stiles breathes, pressing a kiss into the small of Derek's back, crouching down to slowly begin retracting the plug.

As Derek moans loud and deep from the sensation, he feels Stiles' teeth nips along the flesh of his ass, his tongue soothing around his hole, fingers of his free hand pressing in four quickly along side his tongue after the plug pops out. "Don't worry, I'm not going to leave you empty. Good boys don't deserve to be empty. They deserve to be full."

Derek claws at the couch cushions when Stiles' fingers skirt his prostate, wants to protest when his tongue retreats but hears Stiles spit followed by the sound of skin slicking. Then it's right back in his hole, slicking him more,

"You're so wet, still. Going to be so easy to just slip inside you." Stiles sighs, "I've been wanting to get my mouth on you because you're so loose. I bet I could keep my fingers in you and still manage to slip my dick right in. Is that something you'd like?"

Derek whimpers but manages a weak nod. Wants every part of Stiles in him, mind, body, soul, everything.

"Next time, Der. Next time," he promises. "I'm going to pull my fingers out now, give you a moment, and then fuck you, okay?"

"Just fucking do it."

"Needy bottom, aren't you?"

Derek doesn't feel embarrassed because Stiles is just as bad, if not worse, when Derek teases him within an inch of begging before he finally fucks him.

Stiles doesn't give him the moment. He just takes his fingers out, lets Derek's hole try to clench around something for a second, and then sinks in all the way.

If he did have neighbors, their moans would have the cops called on them in a heartbeat.

Stiles is stationary for a moment too long for Derek's taste, so he begins to fuck himself back on Stiles' cock. Feels him hot and heavy inside his ass, filling him in ways the plug couldn't.

"You just gonna take your pleasure from me, then?" Stiles asks, hands leaving their bruising purchase on Derek's hips to flatten against his ass instead. "Okay then, fuck yourself on me."

The first few thrusts he manages are sloppy, but the stroke of Stiles within him is so good.

He braces himself better against the couch by lifting one knee onto the seat, before rolling his hips, fucking himself back onto Stiles until he can feel the weight of Stiles' balls against him. He holds him deep for a moment, grinding himself there.

"You look so perfect, fuck, Derek." Stiles is breathless, hips twitching forward. He tenses like it was involuntary, holding himself perfectly still because he handed the reigns to Derek. "You have a cock in your ass and you're not doing anything with it, Derek. Should I show you what to do?"

Derek doesn't breathe a word, can't, but he stills himself, arching his ass as much as he can so that he's displaying himself to Stiles.

"Fuck." His thumb brushes over their connection, "I should film us one day, so you can see how gorgeous you look on my cock." Stiles grips Derek's hands and starts thrusting into him slowly, "Maybe get some mirrors and put them above the bed, next the bed, so you can watch." His thrusts get short when he stays deep, pulling out just enough for him to stimulate Derek's prostate and have him near keening, "Maybe we'll get neighbors across the way and they can watch, see how prettily you take me."

Derek pants, head hanging low. He can feel the fourth building already; feels it everywhere in his body. By all means, he should be oversensitive, should be dry, but he's harder than he's been all day, because he finally has Stiles inside of him.

"You almost there?" All Derek can manage is a nod, "Good." And then the tip of the plug is vibrating against his perineum and he's shooting rope after rope of come onto the couch cushion. The broken sounds that come out of his mouth sound like Stiles' name mashed with curses riding on a sob as wave after wave of pleasure shakes through Derek.

And Stiles is still milking him with short, stabbing thrusts of his hips. "So good." He murmurs, pulling Derek up so that his back is flat against Stiles' chest. "Walk with me." He whispers, guiding Derek with gentle presses of his hands as cues.

They make it to the bed, Derek falling bonelessly onto it and ripping the breath from Stiles when he's forced to slip out of Derek at the movement.

"Want to see you." Stiles says, rolling Derek onto his back. "Need to watch you. Know why?" His fingers lace with Derek's, trapping his hands on either side of his head. "Because you're fucking gorgeous. You are all the time, but like this, you're just a masterpiece."

Derek arches into him when Stiles breaches again. The slow drag over his prostate is like sweet torture.

"You're sweating and blissed out, almost glowing. All because you took my cock so nicely that you came from it without even touching yourself. That's amazing." Stiles presses a chaste kiss to Derek's mouth, "You're perfect."

It takes Derek a moment to realize the whine's from him. Stiles' words always punch all the right buttons. He never believed shit like that before Stiles worked on telling him every day. And since he first started doing it while they were fucking, it was a whole new world that opened up for Derek. He'd never known he had a praise and dirty talk kink before Stiles. He didn't know he had a lot of kinks before Stiles.

"Fuck, Der." He can feel Stiles' rhythm become erratic, feel the head of his cock slipping over every nerve ending inside him like a match striking. "Gonna plug you up again," he promises, the low growl to his voice making Derek wrap a hand around his dick, "Keep my come inside of you 'til I'm ready," he's panting, teeth grazing across collarbone and available muscle between words, "Then I'll turn the plug on and mix my come up inside you, like I knotted you," he pulls back, staring down as Derek jerks himself, "While I ride your dick until I shoot all over you."

"Fuck!" Derek shoots up his chest, come landing on his cheek, splashing out on Stiles' chest as he ruts in a few more thrusts before emptying himself in Derek.

"Shit." Stiles pants, arms shaking from exertion as he tries to keep some of his weight off of Derek. "That was definitely shorter than four and a half minutes. New record!"

Derek doesn't care though; just wraps an arm around Stiles and pulls him down, rolling them until Stiles is on his back.

Stiles is still hard inside him, always stays hard for a minute after he's come. Derek grinds back, enjoying the feel, the sharp gasp that Stiles releases, the whimper as Stiles involuntarily fucks up into Derek. Derek can feel Stiles' come slick inside his ass, circles his hips to feel it squish around Stiles' softening cock.

Fucking loves it.

"Ass up, don't let my come out." Stiles commands, tapping Derek on the ass.

Derek obliges, clenching down while Stiles slips off the bed. His stomach clenches when he sees Stiles picking up the plug again. Watches as Stiles purposely locks eyes with him, wipes the plug down with one of their shirts before putting it in his mouth. It's shining wet with saliva when it's pushed back into Derek's hole.

Stiles crawls back into bed, sliding underneath Derek--who's still on his hands and knees--and levels him with a tender look. They stare for a moment before meeting in the middle to kiss. It's an I love you, a thank you, a praise, a promise. It's everything for them. There's a sigh as they settle against one another, entangling limbs and snuggling close.

"Rest up. You have an hour 'til I make good on that last promise."

Notes:

Soundtrack for this was Talk Dirty by Jason Derulo and Gorilla by Bruno Mars (hence the awful series name, I suck at titling things).

Thanks for reading!

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