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Dressing in drag wasn’t something Stiles ever thought he would be into. Sure he’d been to a few drag shows at Jungle with Danny, especially since he finally accepted that he was bisexual and decided to try his luck with dudes. His first night actually trying to meet someone he left with four phone numbers and a hickey on the side of his neck from an overenthusiastic guy he met on the dance floor. Stiles hadn’t complained at the time, but he made sure to be more careful from there. The bruise had been a bitch to cover up, and if he never had to have that awkward conversation with his dad again it would be way too soon.
A few nights later he sat with his back against the bar and sipped at a rum and coke—fake IDs were the bomb—and watched one of the girls dancing along with “Super Bass” on the club’s stage. She was gorgeous, all long legs and perfect makeup. There were hundreds of people grinding against each other on the dance floor, but Stiles couldn’t take his eyes off Miss Sugar Snatch as she danced across the stage, black curls bouncing and legs like miles of smooth caramel in her dangerously short dress.
He didn’t know what he was doing the next day when he bought that first pair of panties, but from the moment he got home and slipped them on, his life was different. Better. A hole he hadn’t even realized existed was filled with silky panties, short plaid skirts, and buttery soft, white cotton thigh highs. Apparently his thing for Catholic school girls hadn’t so much been him wanting to date one as much as him wanting to be one. And his legs looked really fucking good in a skirt, if he did say so himself.
Miss Chievous was born, a fierce brunette school girl with a thing for pop music and bubble gum. According to Danny, the one person Stiles felt comfortable sharing his new alter ego, the crowd loved her perfect mixture of innocence and sex appeal, and when the owner of Jungle asked him back for a second paid performance the next week, Stiles couldn’t say no.
Which was why he was in his bedroom past midnight on a Tuesday, half in costume and painting his lips with hot pink lip gloss in a way that would make Lydia proud. His favorite thing about turning himself into Miss Chievous was her lip gloss. It wasn’t the fruity kind, but the tingly kind that made his lips all plump and shiny. It had come as a surprise the first time he borrowed it from Faye King backstage before a show, but he loved how cold it made his lips feel and the thrill of passing the tingle on to the cheek of whoever he kissed while in character.
Lips done, he smiled at his reflection and fixed his skirt so that it was perfectly centered between his knees and hips, pulling the tops of his thigh highs up so only an inch of skin showed between them and the hem of his skirt. After brushing some invisible dirt from his white button down, he finally decided that his outfit was perfect. He thought about finishing the look off with the brown wig that sat on his desk, but quickly decided it wasn’t needed for a trial run of his routine.
He crossed his room to his desk and clicked play in iTunes, the opening notes of the song filling his room. He got into position and closed his eyes, letting his body move itself to the music as he lipsynched along with the song. He threw his arms into the air and jumped up and down on the balls of his feet, moving his hips side to side and shaking his head as he belted out the words. He thought of how the long wig would look swirling around with his body and he made his moves more vigorous. The dance reeked of energy and freedom and the thrill of being young and stupid.
Four and a half minutes later the song ended and Stiles couldn’t stop himself from laughing in outright bliss. If the crowd had been wowed by him hoping and spinning across the stage to “Like a Prayer,” then this was going to leave them speechless. Even with his eyes closed he could tell that the routine was as close to perfect as it was going to get. There would be changes the next time he practiced, and the time after that, because that was typical with improvised performances, but he thought the unpredictable nature was what made it so perfect. Miss Chievous thrived on her youth and innocence, and Stiles was afraid that obsessing over a routine until every step was perfect would take away from the raw manic energy.
A quiet cough cut through the echoing silence and Stiles froze. He knew that cough, and considering he was facing the closed (and locked) door to his bedroom, there was only one guess as to who the other person could be.
Neither of them spoke for several minutes, Stiles too mortified to find words and he could only assume what was running through Derek’s mind. Fuck, fuck, fuck. Why hadn’t he thought to lock his window and pull his blinds? Derek had been dropping in unannounced like this for years now. He should have known better.
“Derek, I—”
“Shut up.”
Stiles closed his mouth with an audible click of teeth. He breathed heavily through his nose and clenched his hands into fists, doing his best to ward off the panic attack he could feel building in his chest. Derek Hale was in his room and Stiles was 99.9% sure he’d caught Stiles hopping around and singing along like a teenage girl. Which was exactly how he was dressed.
“Jesus fuck…” Stiles whispered, letting out a long exhale of breath. He was so screwed.
He heard Derek step toward him, the thumps of his boots against the floor mixing with the familiar rustle of leather, and he took a deep breath, forcing himself not to turn around. “Is there a reason you’re dressed like a Catholic school girl?”
“Haha, yeah about that…” Stiles closed his eyes and took a deep breath, willing himself to stop shaking. “As nice as it is to see you, or not see you because, you know, you’re behind me and all that, could you please leave? Like now? Because if you don’t I’m going to puke and this already life-scaring situation will be a million times worse.”
“Turn around.”
Stiles shook his head and squeezed his eyes closed even tighter. “Nope. I’d like to not do that very much, thanks.”
It was pitiful, he knew that, but he didn’t want to see the disgust on Derek’s face. He wasn’t deluding himself. He’d known from the beginning that Derek would never be attracted to him. After all, Derek was hot and buff and could have anybody he wanted, and Stiles was just… Stiles. There was no competition.
“Stiles…” The words were a growl, low and dangerous. “Turn. Around.”
“Yeah, okay.” Stiles knew better than to fight when Derek used that tone. He probably still had the scars on his back from being shoved against one too many walls for ignoring that warning in Derek’s voice. “But only because you asked so nicely.”
He pivoted on a heel so he was facing Derek, trying his hardest to hide how badly his shoulders were shaking, even though he knew Derek had known the moment the quivers started.
“Look at me, Stiles.”
Stiles cracked open one eye, only to see Derek standing there with his arms crossed and a blank expression on his face. Typical Derek, all things considered, so Stiles let his other eye open and let a sheepish grin spread across his face.
“So…yeah… You caught me, now what are you doing here?”
Derek’s brow furrowed and he cocked his head to the side. “You’re wearing makeup.”
“Very astute of you.” Stiles rolled his eyes and crossed his arms over his chest. “Could you not with the question avoiding thing for once? I know it’s your favorite but—”
“You’ve been skipping out on Pack meetings lately,” Derek stated, matter of fact. He let his eyes roam over Stiles from head to toe. “I’m guessing this has something to do with it.”
“Yes, obviously I’ve had some things going on the past few weeks. Months. Whatever. I’ve been busy, and I was tired of sitting around doing nothing while everyone else was given some big important thing to do. I’m sorry for not seeing the point in going to Pack meetings when it was obvious I didn’t belong there.”
Stiles didn’t mean to let his mouth run, but once he started he found it hard to stop. “I mean, it’s okay. I’m human and can’t really be ‘Pack’ like Scott and Isaac and the others. I get that. But Lydia and Danny are human too and you give them shit to do all the time. I’m justas smart as them, Derek, if not more so in certain places, and you still just let me sit there and feel completely worthless week after week, even though I’ve been there for Scott and—and for you, for God’s sakes, from the fucking beginning. I couldn’t do it anymore.”
Stiles would be lying if he said he wasn’t expecting it when Derek surged forward and slammed him against a wall, jaw clenched and nostrils flared.
“You are Pack,” Derek growled through gritted teeth. “And you will always be Pack.”
That was the last thing he expected Derek to say. If anything he kind of thought expected him to skip words and jump right to the throat ripping-outing. It was much more animalistic, just like Derek, unlike this “emotion feeling” creature in front of him. But instead of letting the words calm him, the urgency and sincerity in Derek’s declaration just pissed Stiles off even more.
“Then prove it!” he shouted. “I’m not your whipping boy, Derek, so stop treating me like one!”
Derek’s lips against his were even more unexpected. They were a little dry and chapped, but as surprised as he was, Stiles could help but reciprocate. Derek teased the seam of his lips with the tip of his tongue, and Stiles let his mouth fall open, lifting his arms to wrap around Derek’s neck and pull him even closer. A shiver raced down Stiles’ spine when Derek let the tip of his tongue brush against his palate, and he couldn’t hold back the desperate moan that bubbled up in his throat.
“You are Pack,” Derek whispered when the pulled apart for air. “You’re my Pack.”
Stiles surged forward and caught Derek’s lips again, groaning low in his throat when Derek’s hands gripped his thighs so tight he was sure there would be bruises later. In the moment, he was too turned on to care, wrapping his legs around Derek’s waist when he lifted him from the ground. When breath was necessary again, Stiles rested his head against the wall and took in the feeling of Derek rubbing his hands up and down his thighs, fingers sneaking below his skirt and gripping his ass, and Derek nipping at his neck, his stubble leaving behind a delicious burn. Stiles arched his back and ground against Derek’s groin, moaning when he felt the obvious bulge against Derek’s jeans against his own silk covered erection.
“Derek, Derek…” Stiles wiggled around and used both hands in Derek’s hair to pull him away from his neck. He bit back a gasp at the blissed out look on Derek’s face, eyes hooded and pupils blown, lips swollen and red. “Bed. My bed.”
That seemed to pull Derek back into reality a bit. He flexed his fingers against Stiles’ thighs and ducked his head so he could look into his eyes. Stiles tried to offer a reassuring smile, but he was pretty sure it came out more as an uncomfortable grimace than anything else. Regardless, Derek walked backwards and Stiles tightened his arms around his neck to keep from falling to the floor.
They tumbled backwards onto the bed in a tangle of limbs with Stiles on top of Derek. He took a moment to take in the view. Derek’s hair was a mess and his shirt had ridden up to show his stomach. Stiles couldn’t stop his fingers from pressing against the exposed flesh, watching as Derek’s muscles tensed in reaction to the teasing touches. He slid his hands up higher, pushing the shirt up to Derek’s armpits, and sank down so he could press an open mouthed kiss to Derek’s solar plexus. He couldn’t hide his smile when the kiss was met with a quiet gasp, the sound turning into a groan when Stiles toyed with Derek’s nipples.
“Sensitive?”
Derek growled low in his throat, and Stiles couldn’t help but laugh, putting his hands to better use by pulling Derek’s shirt over his head.
“How are you real?” he whispered, pulling back to sit on Derek’s thighs, eyes roaming over his chest and stomach with reverence. How is this real? He choked the words back. He had wanted this for so long and he wasn’t going to let his stupid mouth scare Derek away.
Derek’s hands slid from Stiles waist and under the fabric of his shirt, fingers skimming lightly across his back and leaving a trail of goosebumps in their wake. Stiles shivered and closed his eyes. He could only imagine how he looked, straddling Derek’s thighs, head tipped back and lip gloss smeared across his face from their kisses, like a whore. He bit his lip and thrust his hips down, moaning when his groin brushed against Derek’s. The friction was delicious, but he needed more.
Dipping back down, Stiles kissed Derek slowly, pulling away before they could get lost in it.
“I want you to fuck me,” he whispered against Derek’s lips, thrusting his hips down as he struggled to keep his voice even. “Please. I’ll make it so good, Derek. I promise.”
“Oh, yeah?” Derek buried his face in Stiles neck and pushed his hands under Stiles’ skirt, sliding his fingers beneath the waistband of his silky panties. “You’ll be a good boy for me, Stiles?”
Stiles nodded violently and whined as Derek slid the panties down his thighs, the combination of his calloused hands and the soft silk against his skin almost enough to unhinge him completely. He forced himself to take even breaths, pushing his orgasm away. He wasn’t under any delusion that this would mean anything, but that didn’t mean he was against it lasting as long as it could.
“I’ll be so good for you,” he hissed as Derek sank his teeth into the juncture of his neck and shoulder, hips canting forward at the resulting pleasure pain. “Just fuck me. Please.”
Derek left the panties at the bend of Stiles’ knees and sat up, arms wrapped around Stiles’ waist to keep him from falling backward. “Take off my pants,” he commanded, arm reaching out to Stiles’ bedside table to grab the bottle of lube he kept there for late night wank sessions.
Stiles put his fingers to work, undoing and pulling off Derek’s belt before popping the button and yanking down the zipper. He slid back and stood long enough to take off his panties and slide the jeans and black boxer briefs halfway down Derek’s thighs, the backs of his fingers running teasingly along his cock, before Derek was pulling him back in again, teeth latching onto Stiles’ bottom lip and pulling.
“Enough, enough,” Derek groaned, hands settling on Stiles’ hips to situate him so their cocks were flush against each other. “Do you have a condom?”
“Don’t worry about it. Wait!” Stiles jumped back and put a hand on Derek’s chest to keep him away, his face suddenly serious. “Unless your jizz is gonna make me wolf out. Will it? Because yeah… This here?” He gestured between himself and Derek. “Totally awesome. This turning me into a wolf? Totally not.”
Derek snorted and wrapped a hand around Stiles’ wrist, pulling him forward in a flurry of flailing limbs. “I’m positive it won’t turn you,” he muttered into Stiles’ hair, “but it’s still better to be safe than sorry.”
Stiles nodded and pushed himself back up so he could blindly sift through the mess of papers and old cell phone chargers in his bedside table drawer until his fingers found a small foil square.
“Just to be clear,” he said as he settled back on Derek’s thighs, dropping the condom off to the side, “no, um…knotting, okay? Do you even knot? I mean, it doesn’t sound too bad, but… Hey! Stop laughing, Dude! It’s not funny!”
Stiles tried to be pissed, really he did, because while knotting actually sounded kind of hot, it definitely wasn’t something he wanted to experience his first time with Derek. But Derek laughing was…beautiful. Stiles knew he was staring with his mouth hanging open like an idiot, but he couldn’t help it. Derek’s eyes crinkled at the corners when he laughed and his face was so open and free. In the three years that he’d known Derek, he’d never seen him so happy. Ever. It was strangely vulnerable.
Before he could talk himself out of it, Stiles dipped down and kissed Derek, slow and deep, unlike the passionate and messy kisses they’d started with. Derek groaned and let a hand rest on Stiles’ waist, the other coming up to cup the side of Stiles’ face. He kept the hand there when Stiles pulled away, his thumb brushing gently against his cheekbone.
“You don’t have to worry about a knot, Stiles,” he said with a smile. “I’m human.”
“Okay.”
“Okay?”
Stiles put a hand over Derek’s hand on his cheek, smiling softly. “Okay.”
Derek nodded and let his hand drop, reaching for the lube that lay forgotten beside them. The pop of the cap was loud enough to make Stiles jump, moaning as the movement brought their cocks together again.
“Bend over,” Derek whispered as he squeezed some of the lube into his palm.
Stiles fell forward and scattered open mouthed kisses across Derek’s neck, pausing to suck at his pulse point. He bit down when he felt a finger circling his hole, hissing quietly at the slight burn when two pressed inside him.
“Shh…” Derek brought his free hand up to run through Stiles’ hair. “I won’t hurt you. Relax for me, Stiles.”
Stiles squeezed his eyes closed and concentrated on taking deep, even breaths until he felt himself relax enough that Derek could push his fingers in all the way.
“That’s a good boy,” Derek whispered.
Stiles moaned and pushed back against Derek’s hand, rotating his hips slightly before pulling forward and slamming back again. He fucked himself open on Derek’s fingers, movements getting more and more erratic as he found the perfect angle for Derek to hit his prostate. Derek’s hand slid from his hair and down his body, stopping to grip one of his thighs.
“Fuck, okay.” Derek tightened his hand around Stiles’ thigh until he stopped. “Where’s the condom?”
Stiles grabbed the foil wrapper where he’d dropped it and ripped it open with his teeth. Derek groaned and grabbed it from him, letting his fingers slide out of Stiles’ ass. Stiles whined, squirming impatiently while Derek blindly rolled on the condom. He hissed “yesss” when he was finished, grabbing to the lube to squirt a bit in his hand and slick himself properly.
“Come on,” Stiles groaned, taking himself in his hand, but Derek batted his fingers away after only a few short strokes. “Derek.”
“Now,” he groaned.
Stiles let out a blissful laugh and let Derek guide himself as Stiles sank back. He moved slowly, almost painfully slow, pushing himself up until he was sitting and Derek was seated fully inside of him. Derek’s hands rubbed soothing circles into Stiles’ quivering thighs.
He took a few seconds to adjust to the feeling of being so full, wiggling his hips and watching Derek’s face closely. He could tell from the tension in his jaw and his quick, shallow breaths that it was taking every ounce of Derek’s control for him to not fuck up into him with reckless abandon. Stiles lifted up a couple inches and slammed back, smiling when Derek’s fingers squeezed his thighs.
Finally, Stiles settled his hands on Derek’s chest for leverage and lifted himself up almost all the way. He dropped back down and groaned when Derek thrust upwards, his cock sliding deeper than before and hitting right where Stiles needed it to.
“Fuck, yes,” he moaned, head thrown back as he bounced himself up and down. “Right there.”
“Jesus, Stiles,” Derek groaned, hands sliding up and down Stiles’ thighs reverently. “You ride cock like you were born for it.”
“Fuck! Only for you.”
Stiles whined at the sound of Derek’s growl, his thrusts stuttering when Derek wrapped a hand around his erection and started pumping, fast and almost too tight, just the way Stiles liked it.
“God, Derek, I’m not… I’m close.”
“Look at me, Stiles.” Derek lifted one of his hands from Stiles’ thigh to grip the side of his face and tilt it back downwards. “It want to see you.”
Stiles shook his head and tried to look away, but Derek tightened his hold. He panted breathlessly and looked Derek in the eye, whining when he saw how wide and wild his eyes were, the usual sea green overtaken by black. He kept the eye contact and thrust four more times before he came with a shout of Derek’s name, white streaks covering Derek’s hand and the white fabric of his shirt. He collapsed forward as all the strength left his legs.
“I’m sorry,” Stiles sobbed. “I can’t…”
Derek dug his fingers into Stiles’ hips and flipped them over as he continued his thrusts. Stiles whimpered at the movement, too oversensitive and exhausted. A handful of pushes later, Derek buried himself inside Stiles and dug his fingers painfully into his hips, coming with a roar. He stayed there for several seconds, his breathing erratic and fingers flexing, until he pulled out and moved away. Stiles closed his eyes and choked back a quiet moan.
He didn’t remember hearing Derek leave, but a few minutes later the bed dipped beside Stiles and deft fingers unbuttoned his shirt and pulled it off his limp body. His skirt and thigh highs followed quickly. A brief flash of embarrassment at being completely naked overcame Stiles, but he was too tired to cover himself. He hissed when a wash cloth swiped across his stomach a few seconds later, flinching away from the sudden chill.
“You couldn’t have used warm water?” he groaned.
Derek smirked, but otherwise ignored Stiles’ complaints as he cleaned up their mess, even going so far as to drag the wash cloth over Stiles oversensitive cock. He moaned and slapped Derek’s hands away, rolling onto his side and curling into a ball. Doubts rolled unbidden through his mind.
“Stiles…”
“Nope, sorry. I just had, like, the best orgasm ever, and I’m too exhausted to talk to you right now. You know the way out.”
Derek sighed and Stiles could hear him moving around his room. He expected him to get dressed and leave, nothing more said between them, but after a few minutes of silence, an arm slipped under Stiles’ body and lifted him from the bed.
“What the…” Stiles flailed and wrapped his arms around Derek’s neck so he wouldn’t fall. “What are you doing?”
“Fixing your blankets, idiot.” He dropped Stiles back onto the bed and climbed in behind him, pulling the sheet and comforter up to cover them. “It’s too cold to sleep on top of them.”
“Derek, what mmph—”
“Nope, you’re tired, remember? We’ll talk about it in the morning.”
Stiles bit the fingers over his mouth and turned so he could glare over his shoulder. Derek lifted an eyebrow and smiled his most innocent smile, but Stiles could still see the hesitation in his eyes.
“In the morning?” Derek nodded. “You’ll still be here? And we’ll talk?” Derek nodded again and Stiles nodded in return, rolling back onto his side. “Okay.”
Stiles nestled into his pillow and sighed quietly when Derek wrapped an arm around his waist from behind, pulling him flush against his chest. He smiled when he felt him press a kiss against the top of his head.
“Goodnight,” Derek muttered into Stiles’ hair.
Stiles snorted and snuggled back into Derek’s hold. “Goodnight, Derek.”
Stiles let his eyes fall closed and lost himself in the quiet sound of Derek’s breathing, in the blissful feeling of falling asleep curled around another body. He hadn’t let himself get carried away in the beginning, but now that Derek stayed, Stiles desperately wanted more of this. Not necessarily the sex, just him and Derek, tangled together in bed every night. And as he fell asleep to the steady beat of Derek’s heart and his arm tight around his waist, he couldn’t help but hope that Derek wanted it too.