Work Header

Favorite Bottom Boy

Work Text:

"Mr. Hale?" Erica knocked on his door, pushing it open with her hip, her head tilted and her ruby-red lips stretched into a shit-eating grin. "The Stilinski’s are here for your one o’clock."

Derek raised his head from where he had been studying the scotch in his glass tumbler. “Let them in,” he said coolly, though his calm demeanor was belied by the way his cheeks had flushed red and his hands began to sweat.


Stiles was the first one in, as usual, a tight-fitting tee underneath his signature plaid overshirt. His pale cheeks were flushed, his lips parted and shiny with spit, and he winked when he caught Derek looking.

Derek’s heartbeat stuttered and Stiles smirked. They did it on purpose, Derek knew.

When he had first hired them, Derek had no idea what he wanted, and he didn’t really think that getting fucked, by twin brothers, was really his thing, but when they showed up that first night, looking like one of them had just been sucked off on the way up to his apartment, Derek had gotten harder than he ever thought was possible.

He hadn’t looked back since.

The twins had always been adamant that while they’d be okay with fucking Derek together, incest was off the table, and Derek was okay with that. Really, he was.

But god, it was always so hot to think about.

Maybe Stiles had jerked Stuart off in the elevator on the way up, biting his lips as he muffled Stuart’s moans with the palm of his hand, because Stuart could get loud.

Derek’s dick twitched at the thought and Stiles chuckled, his eyes dropping to Derek’s crotch as he stepped aside to reveal Stuart walking in, tapping away on his phone, his glasses slightly askew.

"Yo, Derek," Stuart nodded, pushing his glasses back up his nose and messing around with his beanie until Stiles pulled it down over his eyes. "Hey!"

Stiles laughed, his fingers lingering on Stuart’s cheeks for a moment too long as he fixed the beanie back onto Stuart’s head. Each time they shared any kind of suggestive touches, it was for Derek’s benefit, though they drew the line at actually performing sexual acts to each other and Derek respected that, which was probably why he was their favorite client, though that could be something that they told him so he didn’t leave, not that he wanted to.

After the fire, it was just easier to clear his head when someone fucked him so hard he couldn’t think, much less focus on the way Laura’s hair used to look almost red in the sunlight, and how Cora would cry about not being as pretty as her to their mothe—

“You over thinking again Der?” Stiles murmured, and Derek looked up, nearly swallowing his tongue when he saw that both boys had stripped off their shirts, and Stuart had his claws out, studying them with a bored look on his face. Derek shook his head and Stiles grinned, bright and sunny. “How long have we got?”

“I’ll bet it’s not even close to being long enough,” Stuart cut Derek off before he could even open his mouth and he flushed, not even bothering to hide the way his breathing had sped up. There was absolutely no way a human could mask emotions from a werewolf, much less an Alpha. It was the first thing the girl on the line—Lydia—told him when he called. Stuart winked at Derek, before licking his lips, and jerking his head at Derek’s shirt. “Off, now.”

“What are we doing today?” Derek cleared his throat, loosening the tie from around his neck and getting to work on the cuffs of his shirt. That was another thing. They never really organized what they were doing beforehand, unless there was a serious time constraint, and even then, Derek was content to let them decide what they wanted to do.

“You’ll see,” Stiles murmured, his eyes dipping as he took in Derek undoing his shirt, his tie still around his neck. “C’mere,” he reached forward to grab both ends of the tie, tugging Derek closer towards him before slotting their mouths together easily, Derek’s hands trapped between their bodies. Stiles licked into Derek’s mouth and he opened up easily, his fingers forgetting about the buttons and instead slipping underneath the hem of Stiles’ shirt, fingertips ghosting over his too-warm skin.

Derek shuddered into Stiles when he felt Stuart begin to mouth at the back of his neck and his hips jerked forward helplessly when Stiles’ hands slid down from the ends of his tie to finish undressing him, his long fingers thumbing at Derek’s nipples. He pulled away, panting, already painfully hard, trapped in his dress pants, his hips twitching for some friction against Stiles’ warm body.

"Stop it," Stuart commanded and Derek could barely contain a whine and he reluctantly slid his hands from Stiles’ hair (when did they get up there?), forcing himself to take a step back. Stuart walked around him, his claws trailing lightly across his shoulders and his bare chest, eliciting goosebumps in their wake and Stuart brushed his lips against Derek’s ear. “Good boy,” he murmured, and this time, Derek couldn’t hold back a hoarse moan. Stuart’s mouth quirked up and he pressed a short, close-mouthed kiss on Derek’s slack lips.

“I think we’ll stick to the classics today,” Stuart said, unbuckling his jeans and nodding at Stiles to do the same. When they were both dressed in their boxers, Stuart jabbed his claws into the middle of Stiles’ back, and Derek looked away.

Watching them fuse was always a little less than comfortable, because even while Derek could see it happening, his brain just refused to rationalize it, and often he was left with a confused boner. They weren’t as big as Derek assumed they would be when they merged, but they were definitely bigger than they used to be, almost as big as Derek, with impossibly broad shoulders and all that bulk tapering down to slim hips and powerful legs.

It was their faces that really got to Derek, because even though they were identical, there were subtle differences and when they were sharing one body, they still looked like a Stilinski, but it was hard to place which part of whom was actually used. It was hard to describe, but if Stuart and Stiles had a twin, it would probably look like their merged form.

While the merging was what really made the twins as popular as they were, with Derek, they didn’t fuck him as one all the time. Sometimes they’d take turns, and on one memorable occasion, Stuart had decided to fuck his mouth while Stiles fucked him from behind.

Maybe it was unhealthy, craving to be used, but the twins had never exploited that, and Derek didn’t have the time to look for a real relationship that would be as fulfilling in bed while putting up with his admittedly surly personality.

"Spacing out, already? Must not be doing our jobs right."

Derek turned to the twins, shirtless, his thumbs hooked into the waistband of his pants. “Should I take these off?”

It was always a bit difficult when looking at them in their merged form. Stiles had tried to explain how it worked one time but it hadn’t cleared up anything. They were still two minds, just stuck in the one body, and Derek had gotten good at picking out who was talking.

Stuart grinned at him and cocked his head. “Well, you’ll probably need them afterwards, so…” he trailed off and Derek nodded, his throat going dry.

“Hey,” Stiles murmured, stepping closer and stilling Derek’s hands from where they were undoing his belt buckle. “Are you okay?”

Derek shook his head. “I just… Need to forget for a while.”

“Thank god we’re good at that, huh,” Stuart shrugged, a cocky smile stretching the mouth of their shared body.

“God, sharing a body with you is the worst,” Stiles complained and Derek couldn’t stop his lips from twitching in amusement. “Seriously though, Derek, you know the rules. Anytime you want us to stop, just let us know, okay?”

Derek nodded, stepping out of his pants and just like that, Stuart, who’d always been the most dominant of the two, took back control of the situation.

“Take your boxers off,” he ordered, pushing Derek backwards until his ass hit the table, his soft lips dragging across the stubble on Derek’s jaw, pulling back with a chuckle when Derek tried to get to his mouth. “Turn around, hands on the table.”

Derek didn’t hesitate, his dick hard and leaking, an anticipatory shiver running down his spine and without warning, Stuart pulled Derek’s cheeks apart and licked over his hole, his tongue wet and warm and so good. Derek mewled and Stuart chuckled, his mouth pressed against Derek’s hole and the sound vibrated through his whole body, making his toes curl.

One of Derek’s favorite things about the twins was how enthusiastic they were at what they did. He’s shameless now about asking for what he wants, shoving his ass back into Stuart’s face, and moaning out loud until Stuart pulled back just far enough to say,

“Shhh,” and Derek stuffed his shirt into his mouth almost immediately, shivering when Stuart blew softly over his hole, his hand sliding up his crack and thumbing at the rim. “You’re so good for me, Derek,” he murmured quietly, mouthing wetly at Derek’s hole before licking over it messily, getting it just wet enough for the tip of his thumb to slide in.

Derek mewled, his voice muffled through the fabric of his shirt, and spreads his legs further.

“Just hold on, I’m getting there babe,” Stuart murmured, pressing open-mouthed kisses across Derek’s cheeks and licking a wet stripe over him. “Where’s the lube?”

“Drawer,” Derek’s voice was husky, his breath coming out in harsh, wet pants. Stuart sucked a hickey right over his asscheek before he pulled away, reaching across the desk to shuffle through the papers to get to the lube, his erection rubbing against Derek’s ass, something Derek knew was done on purpose. “Please,” he moaned, fighting the urge to grind back against Stuart, if only because he knew that wouldn’t end well.

“Shhh,” one of them whispered, Stiles, Derek assumed, because Stiles just knew Derek, stilling Derek’s trembling shoulders and pressing gentle kisses across his jaw, until Derek turned enough for Stiles to access his mouth, and even then, Stiles refused to take. Instead, Stiles pressed his mouth against Derek’s gently, over and over again until Derek stopped feeling on edge, and his body relaxed. “There we go, that’s a good boy,” Stiles murmured, his hand slipping down to brush against Derek’s cock just to watch Derek’s eyes flutter closed. “What’s bothering you?”

Derek shook his head.

“Talk to me, Derek,” Stiles pulled Derek around to face him, his free hand instinctively digging into the meat of Derek’s hips when he refused to meet Stiles’ eyes.

“Nothing’s wrong,” Derek said, his voice hoarse, and his heartbeat blipping at the obvious lie. He sighed. “I don’t wanna talk about it.”

Stiles pursed his lips. “Okay,” he nodded, his fingers brushing Derek’s cheekbone. “We don’t have to. Just…let me, okay?” Derek nodded and Stiles hooked his hand around the back of Derek’s head, kissing him slow and sweet, his tongue licking into Derek’s mouth until Derek’s breath was coming out in harsh pants, and his hands were twitching at Stiles’ sides.

“We’ll go slow,” Stiles promised, pulling away, tracing a finger down Derek’s sternum, before pressing a kiss onto his collarbone.

Stiles stepped back and there was a moment of hesitation, an inward struggle between the twins, before Stiles seemed to win, and he dropped to his knees.

“You don’t have to,” Derek said weakly, his pupils dilating and his hands already threading through Stiles’ hair.

Stiles nipped the inside of Derek’s thigh, grinning when Derek’s hips jerked forward. Stiles looked up at Derek and winked, gripping the base of his cock with a firm hand before sinking down all the way, and Derek’s fingers tightened against his scalp. Stiles moaned, dropping his hand and letting Derek set the pace, slowly fucking his mouth as Stiles flicked the cap on the forgotten lube.

The first finger was easy, sliding in with barely any resistance and Stiles could feel Derek’s dick twitch in his mouth as Derek’s hips paused for a second, clenching down onto his finger. The second was a slight stretch, and Derek’s mouth dropped open when Stiles brushed against his prostate, his touch feather-light.

“More, Stiles, please,” Derek shut his eyes, and Stiles’ fingers stilled for a moment before pulling out and pushing back in with three fingers. Derek ground down onto the feeling, heat pooling low in his belly when Stiles pressed insistently against his prostate. “I’m—I’m gonna come.”

Stiles pulled back with a smirk. “So come.”

And it’s not like Derek really has any choice in the matter, especially since Stiles had taken Derek back down his throat and all Derek could think was hot, wet, perfect, Stiles, before he came.

Stiles pulled off with a wet pop, pressing soft kisses up Derek’s chest and nipping at his chin. “You said Stiles.”

"S’your name," Derek mumbled, his body soft and pliant, mouth parted and his eyes blinking open.

"You’ve never referred to us separately before," he shrugged, pressing his dick into the groove of Derek’s hips. "It’s nice."

Derek slid his hand down Stiles’ side and remained silent before curling a hand around Stiles’ leaking erection, feeling a thrill rush through his when he grunted and pushed up into his fist.

"I’m okay," Stiles murmured, and the corner of Derek’s mouth curled up as he looked pointedly at the way Stiles’ hips were continuously pumping up to his hand. "Shut up," he rolled his eyes.

"Fuck me," Derek murmured. "And I don’t want it slow."

"Fucking finally," Stuart muttered, batting Derek’s hands away. "That moment was too sappy for me. You guys need to sort your shit out," he rolled his eyes, turning Derek around before nudging at Derek’s entrance, chuckling when Derek pushed back encouragingly, his hands gripping the edge of the table.

"I’m good, I’m good, just do it already, serio—fuck,” Derek bit out when Stuart bottomed out in one thrust, barely giving Derek time to adjust before pulling out and slamming back in. “Jesus,” he breathed out and Stuart laughed.

"It’s Stuart, actually."

"You’re not funny," Derek rolled his eyes just as Stuart slid against his prostate and he let out a little choking noise. If Stuart and Stiles already had huge dicks, their merged form would make a size queen cry. "Right there."

Stuart pulled him up from where he was bent over the desk, until Derek’s back was flush against his chest, letting out a little rumbling growl when Derek tilted his neck in submission without hesitation. Stuart bit down and Derek cried out, his voice quickly muffled by the palm over his mouth.

"Don’t touch yourself," he commanded when Derek reached out to jerk himself off, his dick hard and leaking again, so close to coming. Derek whined against Stuart’s hand and Stuart retaliated with a grinding thrust that had Derek seeing sparks. "You’ll come untouched," he whispered, his face next to Derek’s ear and his breath washing over him. "I wanna feel you come on my knot."

Derek muffled moan had Stuart grinning, his fangs two pinpricks against Derek’s throat.

Stuart’s dick was already swelling at the base, tugging on the rim of Derek’s hole on every outstroke. Derek was panting against Stuart’s palm and he bit down on one particularly hard shove and Stuart let out a warning growl before reaching down to take Derek’s dick in his hand and jacking him off hard and fast.

"I can’t," Derek panted beneath Stiles’ hand, shaking his head even as his body started to tense. "I need to—"

Stuart swiped his thumb across the slit of Derek’s cock at the same time his thrusts had turned into slow grinds, his knot a constant source of pressure on Derek’s prostate, painting Derek’s vision a bright white as he arched his back and came, sticky white trails of come streaking his desk.

Derek clenched hard around Stuart and the latter had to muffle a roar as he came buried deep in the clasp of Derek’s body.


Derek was heaving in between breaths when he finally came to, and his first thought was that Stuart was no longer inside him.

He blinked groggily before squinting at the watch on his wrist.


He wasn’t out for long, then.

"How you feeling?" Stiles asked quietly and Derek jerked in surprise. "Sorry," he apologized, and Derek shook his head.

"Fine," he said shortly before looking down at himself. "Did you clean me up?"

Stiles nodded before letting out a little cough. “Stuart, uh, he left. But I wanted to make sure you were okay.”

Derek’s head snapped up from where he was pulling on his boxer-briefs. “You did?” he paused before looking around for the rest of his clothes, suddenly shy. “Thank you.”

Stiles shrugged. “No big deal.” Once Derek had his pants on, Stiles cleared his throat. “I’m going to head out, gotta go, uh…” he trailed off and rubbed the back of his head awkwardly as Derek stared at the flush spreading across Stiles’ ridiculous cheekbones in awe.

When Derek said nothing, Stiles nodded and turned to go.

"Wait," Derek’s gaze dropped to his hands when Stiles turned back around, an eyebrow raised questioningly. "When I make another appointment…" Derek paused and the edges of Stiles’ mouth began to curl up in a smile. "Could I maybe make one with just you next time? With dinner and everything."

Stiles walked towards him, picked a pen up off the floor before scribbling something on Derek’s chest, right above the hickey on his left pectoral. “That sounds great, call me whenever,” he grinned before leaning forward to taste Derek’s matching smile.