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The first time Stiles does it, it’s only after he’s had a shower, double-checked to make sure his dad isn’t home, and done some very extensive research.
It’s not his fault that “research” in this case consists mostly of critically watching porn, but it’s not like spending weeks painstakingly combing multiple websites for all the best examples was easy. If there were any helpful how-to diagrams, he would have bookmarked those too, but the internet seems to be sorely lacking on that front. He did find a few decent step-by-step guides, at least, once he finally moved onto the shopping phase.
As far as Stiles is concerned, if he’s going to start screwing around with sex toys, he’s going to do it right.
The day the package arrives, he pounces on it so fast his dad asks if they need to call in a bomb squad. Stiles has to spin him a story about stockpiling top-secret birthday presents.
His dad’s birthday isn’t for another five months and he doesn’t exactly seem sold on that excuse, but he doesn’t ask any other questions either.
In the grand scheme of things, the plug isn’t that big. Stiles did a lot of slack-jawed staring at his laptop screen before settling on something that didn’t seem anatomically impossible. It’s smooth and glossy black and definitely wider than his own fingers, which is hands down the most important thing. There’s only so much Stiles can do with his fingers stretching and curling inside himself, only so many ways he can take jerking off to the next level since apparently he’s doomed to die a virgin in this supernaturalism-steeped town.
Once he’s made sure his dad is gone for the day--he might actually have triple-checked, but better safe than sorry--Stiles throws off his clothes and proceeds to have a staredown with the thing.
Which isn’t what he planned on, but this is most likely the closest he’s going to come to actually getting laid for the foreseeable future, however long or short that is. It’s kind of a big step. That deserves a moment.
When he finally finishes getting himself ready, slicks it up, and presses the blunt tip against his hole, he has to shove his face into a pillow to keep from moaning loud enough for the neighbors to hear. Stiles loves the feeling of being penetrated, has ever since the first time he learned he could get off without even touching his dick if he slid a finger or two into himself and rubbed a certain way. This, though--this is so much thicker than a pair of his own fingers, and it flares out at the base until he’s whining from the stretch of it, until his chest is heaving and his hips are arching and it’s almost too much and fuck it all, maybe he should have bought something a little more petite.
Then it slides the rest of the way in and his body eagerly swallows it up, slutty for it, until the base is nestled against the rim of his hole and Stiles is staring down at himself, not sure whether to feel proud or relieved.
It’s so weird at first, having something inside him that isn’t actually part of him, but his hands are free and that’s just plain amazing. Having two hands to jerk off with and something inside him is fucking magical. He can work his cock with one hand, pinch his nipples with the other, ride down onto the plug or press the base of it to make it nudge against his prostate a little harder and holy fuck, that...that is the greatest thing Stiles has felt in possibly ever. The plug doesn’t vibrate, all those were a little more expensive and Stiles figured he should start off with something relatively simple before he leveled up, but fuck, if it did...he chokes down a whine and spills over his hand.
It doesn’t occur to him until the fourth or fifth time he uses the plug, but when it does it hits him like an anvil: he could wear it under his clothes and no one would know.
It seems filthy, the kind of thing that happens in porn and not real life, but...why couldn’t it? For more than a year now, Stiles’s life has been filled to overflowing with things that aren’t supposed to happen; limiting himself is just silly. Maybe it’s not the best idea, but it makes him heat up, squirm, and come all over his belly in no time flat, his body still clenching and working around the toy.
And then he starts getting creative. He warms himself up, slips it in while he’s got the house to himself, and just...gets dressed and does his best to lose himself in World of Warcraft. He only lasts about ten minutes the first time before he has to rut out an orgasm against the edge of his mattress.
He gets better. Ten minutes becomes fifteen, becomes twenty, becomes half an hour. Stiles keeps his hands off himself. Watches TV. Tries to do homework without wriggling and gasping and grinding down against his desk chair. Video chats with Scott, who doesn’t seem to notice anything’s amiss. Stiles feels sort of smug about that; at least he has one secret not even werewolf senses have picked up on.
When he finally manages to keep it in for a full hour, he’s pretty sure he almost dies. But he doesn’t give the game away either--by this point, he’s trained himself not to touch or whimper or hump against the nearest surface just to get off in his jeans. The only thing he needs to do now is test his skills in the real world. It’s still a stupid plan, Stiles knows this, but he’s lost count of how many stupid plans he’s had a hand in over the past several months. At least this one is potentially fun.
Gym is his second-to-last class the next day. All he has to do is wait until the locker room is mostly empty, duck into the bathroom, and make it through calc.
It sounds a lot simpler in his head. Greenberg takes forever in the locker room since he can’t find his belt, and Stiles is already so on edge that he’s sweaty and shaky by the time he finally has the place to himself and gets to finger himself open. He almost mashes his face against the stall door when he finally slides in the plug. He’s actually doing this and it’s so dirty and he feels so full and no one has a clue and god, he just wants to come. He could come, right here, just jerk off and get to class a little late, but that’s not part of the plan. And Stiles breathes. Wills himself to calm down, shakily zips up his jeans, and splashes some water on his face until he looks slightly less like a tomato with hair.
He can’t stop smiling when he walks into calc, probably looking smug and antsy as hell, but Stiles is always a little antsy so he figures no one will notice a difference. It’s perfect, since there are no werewolves in this class to catch his scent and wonder what the hell is going on, and he needs something to liven up math a little.
Of course, he gets called to the board, which wasn’t something he ever considered, and almost has a heart attack. Since there’s nothing at all sexy about calculus or imminent humiliation, he doesn't get hard in front of the whole class, but he squeezes the chalk like his life depends on it because dropping it is just not an option. He's not sure if the outline of the plug would even be noticeable if he bent down, but just thinking about it is terrifying.
But once he makes it out of class intact, there are only two thoughts in his head: driving home as fast as possible so he can finally get off and fuck, this needs to happen again.
He's so proud of this new level of sexual depravity it never occurs to him not to try this again. Yeah, his ever-shrinking conscience occasionally reminds him it's kind of a risk doing it in public, but he doesn't do it often and besides, as risks go this is something nice and uncomplicated. Not, like, the kind of risk that ends up being a matter of life and death. It’s a nice change. And he’d be lying to himself if he said he didn’t relish the paradox of it; he likes feeling sort of crazy and wanton even though he still has no sex life whatsoever.
Then there’s a twist.
“It’s about Lydia,” Scott says to him in the hallway after Finstock’s class. “I need to know if you can do me a favor, okay?”
And Stiles nods vaguely, swears that whatever it is it shouldn’t be a problem as long as there’s no death or maiming involved, and then darts down the hall. He has gym next and the plug is tucked inside his backpack next to a half-empty tube of lube. He’s already giddy.
He doesn’t expect Scott to catch him in the parking lot, after he’s finished spending calc in a state of mild agony from both boredom and constant stimulation. “Dude,” Scott blurts out, “I need you to switch shifts with me, can you do that?”
“What,” says Stiles.
“Can you switch with me?” Scott repeats, earnest-eyed. “My mom’s not feeling well and I don’t want to leave her alone.”
A few days ago, they decided Lydia needed round-the-clock surveillance so one of them would always be at hand if another body showed up and Lydia unconsciously tried to seek it out on her own. So far, it’s worked surprisingly well even though Allison had to convince Lydia to see it as having an entourage and not as having a bunch of really inept stalkers.
“I’m supposed to do a shift later tonight, though,” Stiles blurts, like Scott doesn’t already know this. “With Isaac.”
“I know, man, but it’s just a few hours. Allison can’t get away from her dad right after school, but she said she can sneak out and watch with Isaac later, so you won’t have to go out twice. Please?”
A few hours. That’s a few hours longer than Stiles has ever worn his plug--the few times he’s worn it in public, he’s always gone straight home after school, treated himself to an amazing orgasm or two, then cleaned up and put it away.
He’s dizzy and dry-mouthed already, but Scott is so hard to say no to sometimes. And Stiles would be lying if he tried to tell himself he didn’t like a challenge.
Stiles gives up. “Fine, whatever. But you owe me,” he adds, poking Scott in the chest with one finger.
Scott grins. “Thanks.”
“Wait.” Stiles catches his arm before he disappears into the crowd. “Who are you on watch with?”
Scott jerks his head over his shoulder.
And this is how Stiles ends up sitting in his jeep, parked down the block from Lydia’s house and trying his best not to hyperventilate every time he shifts in his seat.
With Derek.
Of course it would be Derek. Derek with his stupid too-tight henleys and stupid searing green eyes and stupid powers of working his way into way too many of Stiles’s filthier thoughts. Derek who just had to go right ahead and make himself comfortable in the passenger seat before Stiles had a chance to even think about bolting back into the school and impatiently demanded, “Are you driving or am I?” when Stiles stared at him like a moron for what felt like about ten minutes.
They’re almost an hour into their watch and Stiles is ready to cry because that means there are still two whole hours left. Two hours before Boyd and Cora are on watch. Two hours before he can get any kind of relief.
Two. Hours.
When he can’t stand sitting still any longer, Stiles drives up and down the street a few times. He plays with the radio until Derek glances at him, eyebrows low, and turns it off. And that just means Stiles ends up staring at his long, thick fingers and trying to pass a whine off as a cough when his body grips around the plug even more tightly. This was never supposed to happen. He’s not supposed to be here, not supposed to be wondering if Derek would be ruthless with those fingers, stretching him open hard and fast, or if he’d draw it out and make Stiles beg for it.
He starts rambling just to fill the time and take his mind off the situation in his pants. “How come I have to be the getaway driver? I don’t really need my jeep getting written up for suspicious activity and, no offense, you’re kind of a poster boy for suspicious activity no matter what you’re doing.”
Derek gives him a vastly unimpressed look. “Cora has my car.”
“Can Cora even drive?” Stiles demands. Cora kind of came out of nowhere and no one ever really talks about it since Derek is so pleased to have a non-psychopathic family member around, but Stiles still doesn’t have a clue how much Cora actually exists on paper.
That makes Derek’s face cloud over. “Boyd does.”
Which tells Stiles absolutely nothing about Cora, but does make him kind of jealous Derek trusts Boyd with his car. And confirms that Derek still sucks abysmally at making conversation.
Inevitably, even though it makes his nerve endings scream every time the plug shifts inside him, Stiles starts fidgeting. He can't help it, but he always gets fidgety anyway; Derek probably won't even question it. Derek might be annoyed by it and then they can kill some time by arguing, and how sad is it that this is only silver lining Stiles can think of?
It’s not even hot in the jeep, but there’s sweat starting to prickle along his hairline and he ends up stripping off his hoodie. Derek, sitting there in long sleeves, watches but says nothing. Stiles bunches it into his lap, breathes in ragged gulps and wills himself to be calm. Even though it’s agony trying not to rub a palm against his cock, he’s sure Derek can tell how hard he is.
A few minutes tick by and Stiles starts sweating even more and cradling his head in his hands and there’s no way around it, Derek has to know something’s wrong. All Stiles can do is hope and pray he doesn’t figure out what.
“You’re not going to be sick, are you?” Derek asks, and Stiles jumps in his seat, then almost sobs out loud. He wonders if he should say yes, but Derek can tell when he lies and he can smell him and probably isn't picking up a whiff of sickness even though Stiles's face has been stained bright pink for the last half hour.
“N-no, I’m fine.”
“You’re stuttering,” Derek points out, so calmly Stiles wants to smack him even if it means losing a hand.
“Dude, it happens.”
“Not with you. If you’re good at anything, it's talking.”
Stiles snorts and takes extra care not to stutter again. “Thanks.” Fuck everything. This was just supposed to be a normal day. Unfortunately, he somehow forgot his life keeps sprinting far, far away from normal.
He likes to think he can usually talk his way out of anything, but he's never actually been stuck in a car with a ridiculously hot werewolf and a butt plug nudging at his prostate, so apparently this is the proverbial exception to the rule. And yeah, maybe he's had fantasies like this, but they were far less humiliating in his head.
Derek just looks over at him, eyes narrowed a little like he's ready to ask Stiles what the hell is wrong with him--which really shouldn't turn him on as much as it does--but all he says is, "We should just do this another night." And obviously he means sitting outside Lydia’s house like some bargain basement version of Holmes and Watson, but Stiles's brain helpfully supplies plenty of alternatives that are much more interesting and much, much dirtier. “Let’s get you home. I’ll call Boyd, he can take over early.”
Stiles can't even figure out how to form a response to that without babbling, so he just nods like an idiot and starts fumbling with his keys, sweaty-palmed and trying so hard to act like he can't feel Derek's eyes boring into him. He knows he's in no fit state to drive, but what the fuck is he going to do, tell Derek he's impaired and hand him the keys?
Maybe he can make it as far as the 7-11 by the hardware store and claim an uncontrollable need for a Slurpee, then lock himself in the bathroom. Sadly, that's probably the most feasible option there is, even though it'll only take Derek about point five seconds to put two and two together and realize Stiles is getting himself off in there, which means then he'll have to admit he was. That or they'll just never mention it at all and he'll never be able to look at Derek again without getting hard.
Which isn't too different from the norm, actually. How much does he really have left to lose?
“Yeah,” Stiles grits. “Yeah, okay, home is good.”
Unfortunately, he doesn’t take into account the bumps on the road and the fact that his jeep isn't exactly built for a smooth ride. Stiles finds this out the hard way when he almost has a prostate orgasm at a stop sign.
He taps the brakes a little too hard and the next thing he knows Derek is swearing, the jeep is jolting, and all the breath is being forced from his body like there’s a gigantic fist squeezing his ribs. And he can't move because if he moves he knows he'll come, and his hands are so slick on the wheel and thank fuck there's no one behind them at this intersection because he's going to need a minute to pull himself together. Maybe several minutes.
He wishes more than anything that Derek, ruiner of lives that he is, hadn't turned off the radio. That just means he can hear every last sob-edged inhale Stiles forces into his lungs and oh god, he really doesn't want to die like this, from mortification and extreme arousal and squirming down onto a fucking sex toy. He's so turned on Derek has to be able to smell it, even though he still hasn’t said a word. Those acute werewolf senses are merciless.
Derek, Stiles realizes, is probably trying to be polite. It’s kind of sweet, or it would be if Stiles wasn’t on the verge of death-by-butt-plug. Someday, when all this is a distant mortifying memory, Stiles is going to demand to know why he has to be so hot even when he’s ruining lives.
But that’s definitely going to have to wait because his plan of pulling over and hiding isn't really going to work at this point, unless he wants to come all over himself on the ground right next to the jeep, and there are way more important things Stiles has to say. "I need you to get out," he chokes.
Derek can manage, he can wolf out and lope home, easy as pie. Stiles would get out himself if he thought he could, just slam the gearstick into park and run far, far away from this whole mess.
But Derek is staring at him now like he’s actually concerned, not just irritated, which is somehow terrifying and sexy at the same time--so basically typical Derek with an extra helping of humiliation. “Jesus, Stiles, you’re bright red.” And then he reaches out to like he’s about to feel Stiles’s forehead.
Since he gave up on playing it cool a long time ago, Stiles yelps and flails out to keep him from touching him since who knows what might happen, but he hits the power button on the radio instead.
And that, right there, is how Derek Hale unwittingly gives Stiles his first orgasm from a second party, with Ke$ha blaring about looking for some trouble tonight and Stiles laughing hysterically and Derek's palm cupped gently against the sweat-tacky skin of his forehead.
Of course, by now there's a pickup truck behind them with the driver leaning on the horn since they're still at the same damn stop sign.
Stiles just demands, “You couldn’t fucking smell that?” and slumps against the steering wheel.
It turns out Derek can get pretty red too.
Then he yanks open his door, stomps outside, and proceeds to chew out the other driver for being a dick. It’s such a Derek thing to do and it has the added bonus of giving Stiles some time to...well, not compose himself, that point is long past, but at least convince himself he's capable of driving in a straight line despite the plug up his ass and the come in his underwear.
The funny thing is, it never once occurs to Stiles that he could just floor the gas and leave Derek in the dust along with his dignity. Derek has to be dying to know what exactly just happened, either that or convinced he’s some kind of sex wizard. Yeah, Stiles is as horny as the next teenage boy, but not even horny teenage boys come like that. If Derek were a normal human being, he’d be laughing his flawless ass off by now, but he’s not. He deserves to be enlightened at least a little.
Once they're back on the road, Stiles takes a deep breath at the next red light, mentally counts the number of streets before they're back at his house, and blurts out, "Please, please don’t tell anyone else this happened."
And Derek looks at him like he's lost his mind, which Stiles decides is a good sign “Right. Because I was gonna tell all my friends.”
“Um,” says Stiles, cringing internally yet again. Derek doesn’t exactly have friends, it’s just that Derek’s never really acknowledged that before. Creating thriving social circles is really not his forte. “You know what, go on. Just ask.”
It’s a clumsy way of changing the subject, but there’s literally nothing about Stiles that isn’t clumsy by this point. But Derek doesn’t answer, just glances at him with thinly veiled disbelief. And weirdly, that helps set him at ease. It's usually Derek making him all jittery, not the other way around. Derek doesn't let his nerves show very often at all.
He pulls into the driveway, a little crooked but without casualties, and just breathes for a minute or so. “Hey, we made it! Do you need bus fare? Or can you do your wolf thing and get home that way? Because I’m gonna need a little time before I can drive you back to the preserve, just saying.”
And then Derek finally seems to crack. “What were you thinking, Stiles? Are you actually insane?”
There it is. Stiles gives a snort, rolls his eyes, and undoes his seat belt with shaky hands. "Oh, like you never wore a butt plug to school."
The look on Derek's face is only there for a split-second, but worth Stiles's entire video game collection and possibly the external hard drive containing the bulk of his porn stash.
“What, are you gonna start lecturing me about how back in your day kids would never--”
“No,” Derek says slowly. “Even in your day, I don’t think anyone but you would ever.”
Stiles stalks towards the front door, legitimately impressed with himself for not falling over, “I don’t believe in writing things off until you've tried them at least once.” So what if he's already tried this thing like five times. And he knows this really isn’t what he should be getting out of the whole coming-in-his-pants thing, but now that it seems to have affected Derek even more than him, he might have to try it again anyway
“You never answered me,” Derek points out.
“Fine,” Stiles shoots back, as calmly as he can. “No, I’m not insane. Or at least no more insane than someone whose best friend is a werewolf. could possibly be. And you know what, this is probably about as depraved as I can get by myself, so I need to go as far as possible before I die, because let’s face it, at this point it’s definitely more of a when than an if.”
He doesn’t count on Derek actually following him up to the door, still looking sexily bewildered. “You’re not going to die.”
“I beg to differ,” Stiles mutters. He was kind of hoping Derek would learn how to take a hint and leave, but if he wants a ride home that badly he can just fucking wait outside.
When he finally makes it into the bathroom, he almost cries with relief. He definitely moans when he eases the plug out, but Derek’s still outside and the house is empty and Stiles figures he deserves a good moan or twelve after what he just put himself through.
He comes back down to earth be degrees while he washes it off and waits for his cheeks to fade to a less cartoonish shade of pink, and hey, maybe he’s taking so long Derek will get bored and disappear. Derek probably has a degree in creepily appearing and disappearing.
But when Stiles emerges from the bathroom, Derek is standing in the hall near the top of the stairs and all the color floods back into Stiles’s face with a vengeance. “Are you serious?”
“I was--you sounded like--” Now Derek is the one stuttering. He’s also staring at Stiles’s hand.
He doesn’t even bother trying to hide it behind his back. Fate accepted: yes, this is my butt plug. "Dude, if you're waiting for a witty remark, I'm all out. What are you even doing here?"
“I thought maybe--I heard--” Derek begins, and Stiles holds up his free hand because he really doesn’t need to know how much Derek heard or what conclusions he drew. Granted, Derek’s already seen him have an orgasm, so there really aren't too many barriers left between them, but enough is enough. He does sort of wonder if Derek can tell he took off his boxers and shoved them in the hamper, though.
"I have to know, the diminished conception of privacy and personal space, is that a wolf thing, or just a you thing?"
And Derek actually looks like he's thinking about the answer.
Stiles can sort of get it if he tilts his head. Derek lost almost everyone he cared about, so he lives his life trying to make connections even though he sucks at it. Like, really sucks at it. How dysfunctional is his pack again? “You know what, never mind. Next time, maybe just text me before you come charging in, okay?”
Derek’s eyebrows perform their own gymnastics routine. “Next time?”
It’s too perfect. Stiles grins and gives him a wink.
Derek actually goes crimson. This is going to be the highlight of Stiles’s probably very short life.
“I don’t understand you,” Derek says, and he’s doing something with his mouth, something that shows his canines. Stiles can’t tell if it’s more a grin or a grimace. Either way, it’s really attractive because it’s on Derek’s face. And here he’d been thinking that the only upside to this whole situation was that at least now he'd stop being distracted by how hot Derek is and just...be mortified every time he saw him. He’s going to develop a humiliation kink if he’s not careful.
“Pots and kettles, bro,” says Stiles. “See yourself out, okay? I swear I’ll chauffeur you anywhere you want to go, but not now.”
Derek doesn’t even eyeball him for laying a “bro” on him. “I’m touched.”
“I might even throw in a complimentary drive-thru run.”
Derek does that thing with his canines again, then disappears down the stairs.
Stiles holds his breath until he hears the front door click shut, then holds it even longer just to be sure Derek is really gone.
Technically, he should be really disappointed in his dick for not getting the message that Derek accidentally giving him an orgasm and then accidentally overhearing him moan like a slut is not actually hot, but what the hell. He needs to live it up while he can.
That and it’s way more interesting to wonder what the hell kind of orgasms Derek would be capable of delivering if he actually put his mind to it, forget accidental.
So it’s not technically Stiles’s fault he ends up back on the site where he ordered the plug. It’s not his fault he ends up creating a wishlist while he skims for for something new. Maybe something a little bigger. Maybe even something that vibrates. Why the fuck not. Nothing’s been the same since Derek stomped into his life.
And honestly, it’s not like his life can get any weirder.