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Dress You Up

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After the business with Gerard and the kanima, Stiles decides to take a step back from the werewolf drama. He needs to figure out where he fits in this new world, and he can’t do it while he’s neck deep in it. He spends a lot of time thinking about his options and his choices and trying to fix his relationship with his father. And things do get better, but he knows his father is never going to completely trust him again, and it kind of breaks his heart a little, no matter how much it’s his own fault. He still hangs out with Scott, when Scott isn’t busy with Isaac, but they avoid talking supernatural crap as much as possible, and just play video games and practice lacrosse plays.

The problem is, when all of your friends are either werewolves or werewolf adjacent, and you’re avoiding werewolves and their shit, you end up spending a lot of time alone. Stiles is a social creature by nature and by the middle of the summer, he has just about reached his limit for isolation. He is bored and lonely. So, one Friday night, Stiles decides to do something about it. He grabs his fake ID (slightly better than the last one, but still crappy), hops into his Jeep, and goes to The Jungle.

It’s an hour after opening, so there isn’t a line up to get in, which Stiles is grateful for – he hates standing in line – it just makes him twitchy. Okay, fine, twitchier, if he’s being honest with himself. He’d rather burn off his extra energy dancing. He heads for the door and figures he’s got smooth sailing, right up until the bouncer steps in front of him.

“I don’t think so, junior,” the wall of muscle intones with a little smirk as he crosses his arms over his massive chest.

“Hey!” Stiles exclaims as he fumbles for his wallet. “I’m older than I look, man. See?” Stiles holds up his ID.

The bouncer makes an exaggerated effort to look between the ID and Stiles before rolling his eyes and making a shooing motion with his hand. “Off you go, jailbait. The owner doesn’t need to lose his license just because you want to get l -”

“Stiles!” A loud, slightly deeper than female, voice cries out. “Is that you, baby?”

“Oh my god! Of course it’s him, Bunny. Who else would wear a hoodie to go clubbing?” Replies a second voice. Stiles can practically hear the eyeroll.

“Someone needs to teach that boy how to dress,” a third voice despairs.

Stiles looks over his shoulder at the commotion, and spots the queens bustling their way across the parking lot. He grins and waves at them. “Hey, ladies, how’s tricks?”

“Oh, you know, darling, same as always,” replies Bunny, smoothing down her tight red dress. “A little tuck here, a little tape there, and voila!”

Stiles laughs as he’s surrounded by a wall of sequins and glitter. The next several minutes are filled with a flurry of hugs and air kisses and an actual kiss that results in a thumb wiping lipstick off his face.

“What are you doing out here, sweetie? All the action is inside,” says Fanny.

Stiles tilts his head at the bouncer. “He won’t let me in.”

Sandy rolls her eyes, tuts, and flicks her perfect nails at the bouncer dismissing his opinion on the matter, before curling her arm around Stiles’ and walking him through the door. The last thing Stiles hears before the music drowns everything else out is Fanny saying, “Don’t worry, Mike. We’ll look out for him.”

After that, Stiles starts going out with the girls whenever his father works the night shift on Fridays. Fanny likes to mother him, and has made it her job to keep the creepers away. She’s also the one who will sneak him a drink every now and again, but never more than one a night, no matter how many sad puppy faces he makes at her. Bunny tells him all of their secrets, much to his own delight and horror, and gives him advice on how to dress. Some of it he follows – he loses a layer, and buys a couple of pairs of close-fitting jeans, but he refuses to give up the graphic tees. Bunny just rolls her eyes at him and calls him hopeless. Sandy usually has him nearly peeing himself laughing at the scathing running commentary she provides on the cruising going on around them.

Stiles dances and laughs and forgets everything for a few hours every week. He gets to feel like a regular teenager, just out to have some fun. He even gets groped on the dance floor a few times, answering his never-entirely-rhetorical question about whether or not he’s attractive to gay guys. And one night, he gets pressed into a dark corner and thoroughly kissed. Stiles still can’t believe he cock-blocked himself by telling the guy that he was sorry, but he was kind of hung up on someone.

Because, apparently, he is the poster child for hopeless crushes. After Lydia and Jackson declared their undying, magical healing love for each other, Stiles was finally able to move on. Unfortunately, this meant that his subconscious immediately opened the door to all of the little bits and pieces of data it had been collecting on Derek Hale behind Stiles’ back. Like his big, broad shoulders, his sculpted, wet-dream of a body, and the way his shirts just clung to all that ridiculous muscle, not to mention his amazing, multi-coloured eyes, and, oh my god, his ass in those jeans. The worst part, though, is that it isn’t just the physical. If it were just that, Stiles is pretty sure he’d be able to hook up with some stranger in a bar.

It’s everything about Derek. Yes, his default setting is angry asshole, but now that he’s had time to step back and really think about everything that’s happened, Stiles realizes that no matter how shitty he’s been at it, Derek has been trying to do the right thing, and that he really is a decent guy. That whenever they’re together, and the shit hits the fan, Derek puts himself between Stiles and danger. It’s not his fault Stiles is too stubborn to run. So, in addition to all the other shit he’s dealing with, Stiles realizes that he might actually be more than a little infatuated with Derek.

And it’s different than the crush he had on Lydia. He put Lydia on a pedestal. For him, she was the perfect girl – a smart, beautiful, untouchable porcelain doll that he was painfully in love with for most of his life. Yes, he fantasized about her, but only in a PG-13 kind of way – hand holding and kissing and maybe a little heavy petting, but it always felt wrong, even in his fantasies, to go further. With Derek, on the other hand, Stiles nearly jerks himself raw thinking of all the ways he could touch and be touched by Derek, and how it would feel to have all that intensity focussed on him.

The girls notice pretty quickly that Stiles is pining for someone, and they tease him mercilessly until he tells them about his epic, life-ruining crush without naming names. He just tells them he’s older, probably straight, and emotionally constipated. They coo over him and pat him in sympathy, while telling him about some of their more spectacular relationship failures.

After the school year starts up again, Stiles keeps going out with the girls. Midway through October, Fanny says, “You should come out with us on Halloween.”

Normally, Lydia throws a big Halloween bash, but this year her parents are in town, so it’s been cancelled. He doesn’t have any plans beyond handing out candy, so he shrugs and says, “Sure, why not. I’ll have to come up with a cool costume, though.”

“No, sweetie, I mean you should come out as one of us,” Fanny replies, waving her hand elegantly towards herself and Sandy and Bunny. “With those big eyes and killer cheekbones you would look fabulous all dolled up. Let’s not even talk about that mouth. I’m so jealous.”

“Um,” Stiles says, for lack of anything better to say as his brain kind of stutters at the thought.

“Oh, please say yes,” Bunny begs. “I’ve been wanting to dress you up for ages. Please?”

Stiles thinks about it for a few minutes. He’s never really thought about going out in drag before, but it does look like it might be fun, and he doesn’t really have any good ideas for this year. Besides it would make the girls so happy – even Sandy, in all her cynical glory, looks interested in his answer.

Stiles shrugs and grins. “Sure, why not?”

“Yay!” Bunny exclaims, clapping her hands before giving him a big hug. “This is going to be so awesome!”

It takes a couple of weeks to put the look together, but by Halloween, they’ve got Stiles’ outfit pinned down. Stiles finds the perfect dress in Bunny’s impressive collection. He can’t help himself when he sees it – a gothic themed dress in a deep red with some touches of black here and there, with puffed sleeves to hide his shoulders and a lace-up corset built in. The body of the dress is form-fitting, but the skirt flares out at just the right point so that Stiles doesn’t have to go through the horror of learning how to tuck. That’s just way too much for his first time.

Sandy lets him go through her wig collection and they pick out one in black – long and sleek, with straight cut bangs, that she weaves red extensions into to give it little pops of colour. They park him in front of a computer and help him pick out his undergarments from a specialty shop. He finds a matching set in red satin that meets with everyone’s approval, so he puts those in the basket along with a set of black stay up tights. He finds a pair of three inch full platform Mary Janes on another website. They’re not the sexiest shoes in the world, but at least he won’t have to learn how to walk in real heels.

They can’t convince him to shave his legs, but Stiles lets Fanny wax his arms on Halloween after he sees how ridiculous they look in contrast to the rest of the outfit, once he has it all on. He even agrees to a little eyebrow shaping when the sit him down to do his make-up. Half an hour goes by with instructions of look up, look down, blot, blot again, close your eyes, open your eyes being fired at him by three different people, while brushes and sponges and pencils stroke over his face.

When they finally let him look, Stiles’ jaw drops. He barely recognizes the person in the mirror. Somehow, his face has been completely redefined. His eyes are dusted with dark eye shadow and lined with black pencil, making them look huge and the honey-gold colour pop. His lashes look twice their normal length, giving him a sultry look. His mouth is painted a deep, deep red, covered in a shiny gloss, just begging to be smeared.

“Holy fuck,” Stiles whispers, when he can finally speak. “I’m hot.”

“I told you so, baby,” Bunny says, grinning at him. Stiles grins back.

“All right, ladies, let’s roll,” Sandy says, “Let’s dazzle them.” The girls have gone all out tonight, with brightly coloured wigs, feather boas, and sequins flashing everywhere. Sandy’s in neon blue, Bunny’s in hot pink, and Fanny’s in a deep, emerald green. Stiles takes a picture of all four of them for posterity.

When they arrive at The Jungle, Mike, who’s dressed like a cowboy, complete with leather chaps and a whip, gives Stiles a low whistle. “Looking good, jailbait. Stick close to Fanny or someone’s going to eat you right up.” Stiles grins and laughs as he easily avoids Mike’s hand as he fakes a slap at Stiles’ ass.

Halloween at The Jungle is wild. The music is loud and pulsing, the bass line throbbing through Stiles’ body as soon as he enters. Everyone is in costume and inhibitions are low. Stiles is pretty sure there’s some action happening on the dance floor that is usually reserved for dark corners or the men’s room. Stiles waves farewell to the girls and heads to the floor. It takes him a while to figure out how to dance without stumbling or tripping, but he soon gets the hang of it. About an hour later, Stiles is back with the girls, taking a break from dancing, sipping water through a straw so that he doesn’t smear his lipstick too badly.


Stiles coughs and nearly chokes on a mouthful of water. He groans inwardly. He would know that voice anywhere, especially now that it’s been haunting his dreams on a regular basis. He gives a resigned sigh as he is faced with the reality that there is no way he can run away in these shoes. Taking a deep breath, Stiles hands Sandy his drink. Killing a bit more time, he smoothes his hands down the front of his dress, making sure it’s hanging properly, and then squares his shoulders and turns.

He hasn’t seen Derek in months and Stiles was hoping that he’d built him up in his mind, but he’s every bit as breathtakingly gorgeous in his usual ensemble of a tight black t-shirt, jeans, and bad-boy leather jacket as Stiles remembers. It’s almost like a physical blow. Stiles can feel his heart pounding and he’s sure Derek can hear it, even over the music. He just hopes the pheromones filling the club are strong enough to drown out the desperate scent of arousal that Stiles is sure is pouring off him right now.

“Hey, Derek. Happy Halloween,” Stiles says, giving Derek a weak smile. The queens are eyeballing Derek and whispering behind their hands. Derek quiets them with a glare before turning his attention back to Stiles. His jaw is hanging open a bit. Stiles crosses his arms around his body and looks down at Derek – which totally blows his mind, because he’s so used to Derek looming over him somehow, despite them being approximately the same height. Derek sniffs, blinks slowly a couple of times, and then he grabs Stiles by the arm, drags him into the men’s room, and into the nearest stall. Which he locks behind them.

Stiles thinks he knows what’s going to happen next, but he’s still completely stunned when Derek presses him up against the door and kisses him. Derek’s lips are softer than Stiles imagined them being, and his stubble is rougher, but the kiss is just as hot and demanding as he’d always hoped it would be. Stiles melts into it, melts into Derek, and returns the kiss just as passionately. And he is so grateful that this isn’t his first kiss, that he actually has some clue what to do and how to do it. And yet, it doesn’t stop kissing Derek from being completely new and utterly intoxicating. Stiles’ clutches Derek, not just because he wants Derek closer, but because he’s trembling so hard with desire that he needs the support.

Mouths open, tongues touch and slide, hot and wet, and teasing, lip-gloss smudging and going everywhere. Derek’s hands work their way into Stiles’ hair and the wig comes off and ends up flipped over the wall of the stall. Stiles shoves Derek’s leather jacket off and slides his hands under his shirt, needing to get his hands on Derek’s skin. And it’s every bit as awesome as Stiles hoped it would be – smooth skin pulled tight over hard muscle, Derek arching into his touch, gasping out a soft breath against his lips when Stiles drags his fingernails down Derek’s back.

Stiles is getting a crick in his neck so he pulls away from Derek’s mouth to say, “Wait, wait, let me get the shoes off.” As soon as Stiles is flat-footed on the floor, Derek crowds him up against the door again, his body one long hard line of heat and muscle against Stiles’. Derek’s hip is pressed against Stiles’ erection and Stiles moans desperately and tries to move closer. He’s already impossibly hard, uncomfortably compressed in his satin panties, and all he wants to do is rub himself all over Derek until he comes. Derek’s hands start to wander all over his body – light, teasing touches alternating with firm pressure that make Stiles crazy. Stiles whimpers at the slow, sensuous slide of Derek’s fingertips as they make their way up his leg and under the edge of his dress, to the lace at the top of his tights. When Derek’s fingers brush the skin of his inner thigh, Stiles lets out a whimpery gasp that he’d be completely mortified about if he actually gave a shit about anything other than Derek’s hands on him.

Derek’s voice is deep and rough when he whispers, “Fuck,” against Stiles’ kiss-swollen lips.

“Yes,” Stiles replies through a haze of lust, spreading his legs a bit to give Derek room.

“Hmm?” Derek murmurs, fingers still sliding back and forth along the edge of his tights, driving Stiles to distraction as they drift closer and closer to his dick.

“Yes,” Stiles repeats, breathlessly. “Yes to fucking. Yes, you can fuck me. As in, oh my god, why aren’t you fucking me now?”

Derek’s hands tighten on him and, suddenly, Stiles is turned away from the door and Derek is behind him, pressed against his back. Derek runs his hands down Stiles’ body and back under the dress to cup the curve of his ass. He squeezes firmly before sliding his hands to the waistband of Stiles’ panties. Derek trails kisses along Stiles’ neck as he pulls the material down just under the edge of Stiles’ ass. He runs a hand slowly over Stiles’ hip, and then rubs one knuckle teasingly up the length of Stiles’ dick, making Stiles bite back a very loud moan and grind his ass against Derek.

Derek’s hands leave him briefly, only to return a few moments later, one of them slick and slipping down the crack of Stiles’ ass. Stiles tries really hard not to think about why Derek would have lube in his pocket and is just grateful that he does. Derek wraps his free arm around Stiles’ body, holding him close and tight. There’s a gentle tease against his opening that makes Stiles catch his breath, and then Derek’s teeth are biting his earlobe and the finger is pressing in. Stiles gasps sharply and squirms, caught between pleasure and pain and the desire to move away from or into the sensation.

“Fuck, you’re tight,” Derek rumbles in his ear as he tries to push his finger deeper into Stiles.

“I – I – I’ve never – ” Stiles stutters, his breath catching, his body clenching.

Derek goes completely still. Stiles isn’t even sure he’s still breathing until Derek exhales softly against his neck.

“Jesus Christ, Stiles,” Derek says quietly, his voice full of exasperation and sadness. “Your first time should be special. Not in a bathroom stall in the back of a bar.”. The arm around Stiles body loosens and Derek shifts as though he’s going to pull away. Stiles clutches Derek’s arm and uses it to drag Derek more tightly against him.

“Don’t you dare stop.”

“Stiles. You don’t want this, not here,” Derek says patiently.

“Yes, I do. I want this, I want you. It’s the right person that makes it special, not the place. You’re the right person.” Stiles can feel his face heat up as he says the words, but he realizes in that moment, that he really means them. That this isn’t just desperation to finally get laid talking. “Please,” he whispers so softly that he’s pretty sure that only Derek’s werewolf hearing allows him to hear it.

“Christ, Stiles,” Derek replies. He moves his free hand up to cup the side of Stiles’ face as he curves around Stiles’ shoulder to kiss him softly. “I’ll make this good for you,” he promises. Derek lets go of Stiles’ face and curls his arm around him once again. Derek trails more soft kisses down Stiles’ neck and shoulder, and slowly, gently starts to slip his finger deeper into Stiles’ body. “Tell me if you want to stop. At any point. Do you understand?”

“Yes,” Stiles replies, leaning into Derek’s touch.

Derek takes his time, fingering Stiles open at a maddeningly slow pace that has Stiles whining and begging breathlessly by the time Derek is sliding three fingers smoothly into him. Stiles tries to touch himself a few times, but after Derek actually growls at him, while restraining his hand, he finally stops trying. Derek finger-fucks him until he’s a trembling wreck, hips moving rhythmically in time with Derek’s hand. Stiles feels the grin against his skin before Derek licks a slow path up the side of his neck to the sensitive spot just behind his ear that seems to have a direct connection to his dick. As Derek slowly grazes his teeth over the spot, he rubs a slow circle over Stiles’ prostate, and it’s like every nerve ending in Stiles’ body lights up simultaneously.

The high-pitched noise Stiles makes is frankly embarrassing, and possibly only audible to canines, and Derek chuckles against his neck. “Asshole,” Stiles gasps out, his whole body trembling with sensory overload. Everything just feels so good, and he’s achingly hard, the satin clinging to him where he’s leaked all over himself. Stiles is vaguely aware of the clink of Derek’s belt and the sound of a zipper opening over the throb of his own heart beating in his ears, but he is suddenly very aware of the hot, hard cock rubbing against his ass.

“Condom?” Stiles has the presence of mind to ask.

Derek nips at his ear. “Werewolf, remember?”

“Oh, god,” Stiles moans, as a thrill of excitement goes through him, at the idea of Derek fucking him bareback. He knows that Derek is fully aware of his reaction from the way his arm tightens even more firmly around him, and the quiet rumble he feels vibrating against his back as Derek sub-vocalizes a growl.

Derek aligns himself and starts to push in slowly. At the first stretch, Stiles’ breath catches and his body tightens instinctively – Derek’s dick feels massive; way bigger than his fingers. Stiles starts to freak out, just the tiniest little bit. Derek stops when Stiles tenses up.

“Shh,” Derek murmurs, and Stiles realizes he must have squeaked or something equally embarrassing. “Just breathe, Stiles, and try to relax.” Derek rubs his face slowly up and down Stiles’ neck, dropping soft kisses every now and again, and runs soothing hands up and down Stiles’ body. Stiles takes a deep, shuddering breath and lets it go. And Derek’s cock slips further into him. Stiles turns to steal a slow, wet kiss. As their tongues touch and entwine, Derek pushes in the rest of the way. Stiles gasps softly and arches back. Derek starts to move – slow, gentle undulations of his hips that have Stiles sighing his enjoyment against Derek’s mouth. It feels amazing, but it’s not enough. He wants Derek to take him apart. He starts rocking into the motion, pressing back into Derek, trying to get more.

Derek takes the hint and picks up the pace. His breath hot and heavy against Stiles’ neck, his arms curled around Stiles’ body, he starts pulling him firmly back into each thrust. Stiles tries to bite back the soft cries of pleasure that bubble up as Derek’s cock moves inside him until Derek whispers rough and broken in his ear, “Let me hear you, I want to hear your voice, Stiles. The music is loud enough to cover. Please.”

It’s like Derek has opened the floodgates, and Stiles just starts to babble a non-stop stream of ‘Oh god, don’t stop, it feels so good, fuck me, harder, oh my god more, your dick is amazing,’ combined with whimpers and moans and gasps that seem to spur Derek on to hold him tighter and fuck him harder, gasping and grunting into Stiles’ ear until suddenly, Derek moans his name as he thrusts in deep, so deep, and stills, making quiet, broken off gasping sounds against Stiles’ neck as he comes. Derek stays pressed against his back, face pressed against Stiles’ neck for several minutes before he pulls out slowly and tucks himself away. He slides Stiles’ panties back up into place, running his hands firmly over Stiles’ ass, giving it one last squeeze as he flips Stiles’ dress back down. His lips linger on Stiles’ neck and shoulder, and Stiles knows he’s going to have some wicked beard-burn to cover up in the morning.

“Derek, not to ruin your afterglow, but I’m dying here,” Stiles whines, reaching for his cock. Derek stops him again. Stiles whimpers as gentle hands turn him around. Derek gives him a fierce, biting kiss, that leaves him breathless and lightheaded, and then he drops to his knees. He looks up at Stiles and runs his hands slowly up Stiles’ legs, slipping under the dress, to curve around his hips. With a wicked grin, Derek ducks his head under the skirt and mouths his erection, sucking at the profoundly damp spot over the head of his dick.

“Oh, god,” Stiles moans, clenching his hands, not sure what to do with them. He really wants to bury them in Derek’s hair, but he’s pretty sure that’s bad blow job etiquette, no matter what the porn industry has taught him. Derek’s fingers slide under the waistband, and brush lightly along the length of Stiles’ cock as he lowers the material slowly. Derek’s mouth is hot and wet and way too fucking much after being on edge for what seems like forever, and Stiles is coming before he even gets a chance to warn Derek.

“Oh god, oh god, I’m so sorry,” Stiles blurts out, and then moans and shakes through incredibly intense aftershocks as Derek milks his cock for every last drop, licking and sucking until Stiles is whimpering from overstimulation. Derek tucks him away and kisses his way across to Stiles’ hip, where he stops, giving Stiles a hard, biting kiss that Stiles knows will leave a mark. Derek swipes his tongue over the hickey, and then sits back and straightens Stiles’ dress. Looking up at Stiles, Derek runs his hands slowly down Stiles’ legs. He applies light pressure to the back of Stiles’ knees, and Stiles collapses onto his lap, legs sprawled on either side of Derek’s.

“Hey,” Stiles says, softly.

“Hey,” Derek replies, just as softly. Derek cups his face gently with both hands and just looks at him, rubbing his thumbs slowly back and forth across Stiles’ cheekbones. Stiles starts to fidget under Derek’s calm gaze. Derek leans in gives him a devastatingly slow, tender kiss, that makes Stiles tremble with the intensity of it. When it finally breaks, Stiles lets out a nervous giggle and Derek drops his hands to rest loosely around Stiles’ waist.

“You know, if all it took to get your attention was to put on a dress, I would have done it ages ago,” Stiles says, with a small, lopsided grin.

“You always had my attention, Stiles,” Derek replies, hands tightening on Stiles’ waist.

“Then why now?” Stiles asks, genuinely curious. He’s had no hint whatsoever that a) Derek was into guys and b) that he was into him in any way shape or form.

Derek grins at him, showing a fair bit of fang as his eyes flash red. “Because the Big Bad Wolf never could resist Little Red Riding Hood.”

Stiles laughs. And Derek snaps his teeth at him and then pulls him into another kiss, one that threatens to get very heated, very quickly.

“Boys? You about done in there?” Sandy’s voice interrupts. “The natives are getting restless. A girl can only block the door to the men’s room for so long, you know.”

Stiles and Derek startle apart, and then crack up. “Well, that explains why we weren’t interrupted,” Stiles says as he tries to figure out how to make his legs work again. Derek helps him back into his shoes and helps fix the pleats on his dress. Stiles puts his wig back on while Derek slips into his jacket. They leave the stall and are about to leave the bathroom when Stiles catches a look at himself in the mirror.

“Holy shit. Wait. I’ve got to fix this. Bunny will kill me.” Stiles reaches into the bodice of his dress and pulls out a tube of lipstick and lip gloss. Derek gapes at him. “What? Girls keep all kinds of shit in their bras, and I don’t even have real boobs to fill mine, so there’s even more room. I have my phone in here.” Stiles looks at Derek in the mirror. “Uh, you might want to freshen up a bit yourself – you’ve got lipstick all over your face.”

Derek stands next to Stiles and wipes his face. He gives Stiles a glance, and then reaches into the pocket of his leather jacket and pulls out a pair of wolf ears that he sets on his head at a rakish angle. He grins at Stiles when Stiles’ jaw drops.

“What? It’s Halloween. Fix your make-up, Stiles.”

Stiles finishes up and Derek takes his hand as he follows him to the exit. Stiles pauses and raises an eyebrow. Derek squeezes Stiles’ hand gently and shrugs. Stiles smiles at him. They endure the cat calls and whistles as they exit. Stiles thanks Sandy and promises Bunny he’ll dry clean the dress. She tells him to keep it, as it is obviously good luck. Fanny gives him a hug and Derek the stink-eye until Stiles pulls her aside and tells her that Derek’s the guy. Then she gives Derek the ‘hurt him and I’ll gut you’ lecture, much to Derek’s chagrin and Stiles’ amusement.

Derek takes him home with him and Stiles makes him keep the wolf ears the rest of the night.