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One for the Money, Two for the Show

Summary:

The job sounded simple enough to Derek. Some teen wanted to top, his Daddy wasn't too keen on bottoming. So they hire him, he lets the kid jackrabbit against his ass for ten minutes, takes his well-earned money, and leaves. Easy.

But let's be honest, when is his life ever easy?

Notes:

(See the end of the work for notes.)

Work Text:

Derek wasn’t sure what he thought this was going to be. Erica had given him the assignment and sent him out with a sly grin--which should have been his first warning. He read over the card, of course, it was always better to go in expecting something. Anything, really. Surprises were not fun in his line of business.

Pretty common, two guys looking to add in a third for the night. There was a F/S stamp on the lower corner, letting him know this was a father and son--which, fantastic, he’d have to deal with insecurity and jealousy. But family couples tended to be a little easier going, having been together so long they knew exactly what they wanted instead of hemming and hawing around the point.  

Derek didn’t have the patience or inclination to deal with that kind of stuff. If you were brave enough to pick up the phone and order a hooker, you ought to be brave enough to tell them straight out what you bought them for.

But this….this was more than he ever expected.

The meeting had gone easy enough, both of the men mouth-wateringly attractive--though why in the hell a guy named John decided to name his kid ‘Stiles’ was beyond Derek--and they’d been straight forward about what they wanted. Simple enough, John didn’t care to bottom and Stiles wanted to know what it was like to top. Derek had already known he was going to be bottoming so he’d stretched and plugged before even leaving the house. But he...he had almost expected John to join in--typically they wanted to--but when he settled in an armchair at the end of the bed, Derek knew his expectations were slowly escaping out the window.

 

.o.

 

“Get him sopping wet, baby boy. You want a slick slide for your cock.”

Stiles hummed against his hole before licking deep at John’s rumbled order, making Derek’s thighs shake and his cock twitch between them. He chanced a look over, biting his lip at the sight John made, sprawled out in the chair with one hand cupped lazily over his cock. Stiles sucking at his rim had him faceplanting back in the bed, moaning brokenly into the covers.

“He likes it.” Stiles crowed happily, John chuckling off to the side as Derek pressed his burning cheeks into the cool sheets.

“I bet he does. Bet he’d like your fingers even better, stretching that little hole open, getting him ready for your cock.”

“Looks ready now.” Stiles murmured--and he was right, Derek felt open and wet, completely ready to get fucked--but he slid two fingers in anyhow, scissoring them inside him.

“Where is the--how do I--aha!” Derek could hear Stiles’ grin as he pressed against his prostate, making Derek’s cock drool pre-come onto the bed.

“Be gentle with it.” John laughed, “you don’t want him coming before you slide in.”

“But look at how he shakes.” Stiles murmured, awe evident in his voice as Derek trembled under the gentle assault to his sensitive nerves.

“He is gorgeous. Pretty slut for you. Having fun, Derek?”

Derek nodded against the bed, twisting slightly to look at John through heavy-lidded eyes, rocking back against Stiles’ hand.

“Yeah. So good. Wanna feel him inside me.”

Normally the words were rote, stupid things murmured to make the clients happy, but these were real, torn from Derek’s chest. It felt so good, unlike anything he’d ever had before, and he couldn’t help but arch higher, shamelessly presenting himself.

“I wanna fuck him.” Stiles groaned, leaning over the press a kiss to Derek’s lower back, panting against the skin there. “Wanna wreck him on my cock, Daddy, please. I bet he begs so pretty when you fuck him.”

“Alright, alright.” There was exasperation to John’s tone, like Stiles was this eager every time they fucked. “Just be gentle. Be slow. You always moan like a slut when I slide in slow, bet he does too.”

There was a scramble behind Derek before the slick sound of someone smoothing lube on their cock hit his ears and his lower back tingled in anticipation. He honestly did love a slow slide, enjoyed it a hell of a lot more than he did when people just slammed inside him. He hadn’t gotten a very good look at Stiles’ cock, though, having been flipped onto his stomach and eaten out before Stiles had even pulled his own pants off.

But the kid couldn’t be more than 17, so it’s not like he was--

“Oh my god.” Derek groaned, fisting the sheets in his hands as Stiles pressed the thick head of his cock inside.

He was thick, thick enough that there was a slight edge of pain despite all the stretching, and every inch he sank in made Derek’s skin feel tighter and tighter. He couldn’t stop the soft whimpers and moans that slipped out, shuddering beneath Stiles once the boy’s slim hips pressed against his ass. He felt completely skewered, spread open and full, and Derek wondered how in the hell he was going to be able to hold off coming. His cock was already dripping like a faucet, creating a wet patch on the bed, and Derek felt the tingling at the tip that usually came with orgasm.

“Can I--can I fuck him now?” Derek took pride in how shredded Stiles’ voice was, hoarse and husky like he was barely getting the words out. “Daddy? I wanna fuck him so bad.”

“Go ahead. Just go slow. He’s already on the edge of coming, aren’t you, sweetheart?”

Derek nodded and opened his mouth to respond when Stiles started to pull back, the drag and zinging pleasure stealing the words from his throat. He was dazed for a moment, fuck-drunk on the slow thrusts, moaning into the pillow like a five dollar porn star. Only John clearing his throat had Derek re-focusing, pulling him from his thoughts, and then going blank once more at the sight the older man made.

If Stiles was big, he came by it honest. John had his cock out, shirt pushed up and pants opened, stroking up and down the thick length. He looked so good, wetness shining at the red tip, that Derek couldn’t help what was out of his mouth next.

“Let me blow you. Oh my god, please. Please let me suck your cock.”

“Awww, he wants you, Daddy.” Stiles teased, breath gushing hot over Derek’s nape as he leaned low, using the motion to drive forward just a bit harder.

But ‘just a bit harder’ was enough to catch Derek’s breath in his throat with every smack of their hips.

“That wasn’t exactly in the deal, son.” John rumbled, though his eyes were locked on Derek’s lips, brows drawing low when Derek’s tongue flickered out to wet them.

“Don’t care. Don’t--fuck--it’s free. S’free, so free. Just wanna suck your cock. Wanna swallow it down. Wanna--”

“Wanna gag on it, boy?” John rose, somehow managing to look smooth and cool as he strode over, despite the thick cock still hanging from his open pants.

Derek nodded furiously, swallowing thickly as John settled on the bed in front of him. He knew he should wait, should let John grab the condom he was reaching for, but he was a werewolf, and it’s not like John could give him anything. Which is why he didn’t wait, despite the little voice screaming at him to, leaning forward to catch the thick tip between his lips and suck it down.

John’s hands landed heavily in his hair just as Stiles moaned, hips stuttering, movement thrown by Derek’s own. God, he tasted so good, human and warm and clean and strong. Strong like something in nature to be respected. Strong like an icy winter wind that caught your breath in your chest. He tasted...he tasted like Alpha.

Derek moaned around John’s cock, sliding down until his throat caught on it, content to fuck himself with it until his muscles relaxed and he could bury his nose in the dark thatch of hair surrounding the base. Stiles started up again at his back, the rhythm different now, everything he expected of a younger man. Quick jackrabbit thrusts, each one barely grazing Derek’s prostate, somehow more tantalizing than the slow ones had been. He tilted his hips further, opening himself for Stiles, for John, to be used and taken and fucked by these two gorgeous men.

“He’s such a good boy, such a whore for your dick, Daddy. You like that?” Stiles fisted a hand in his hair and tugged--so gently it made Derek shudder and shiver and want to beg for more--until he was rolling his eyes up at John, staring into those dark eyes. “You like getting Daddy dick crammed down your throat? Love choking on it like a perfect little comeslut?”

“Yeah,” Derek slurred out around the flesh keeping his lips open, rubbing his tongue against the underside just to watch John’s eyes slam closed on a groan. “Yeah, love it. Wanna gag on him. Wanna get choked.”

He got a slight warning, John’s stern murmur of “Stiles”, before the pulling on his head turned to pushing. Derek went with a whine, letting Stiles shove his head down on John’s dick until he was gagging and jerking in the hold. Stiles did that for a long while, his thrusts barely even full rolls of his hips, more content to fuck Derek’s throat on his Daddy’s cock than to get off. It wasn’t until John muttered out a “gonna make me come, sweetheart” that Stiles changed it up yet again.

Derek nearly whined at the lack of pressure on his head when Stiles took his hand away, pulling back to mouth at the tip as he waited for what was happening next. The anticipation was making him shiver and he was beyond close, hanging onto orgasm by the tips of his claws. Only sheer control and force of will kept him from coming all over himself, as well as a burning desire to see what these two would come up with next.

He tensed when Stiles squeezed his hips, long fingers digging into his muscles while strong thumbs pressed hard into his tailbone. The weight kept him still, Stiles pinning him in place, but not for long. Stiles’ next thrust was hard, rocking Derek forwards and cramming John’s cock right back down his throat. He didn’t even have time to gag before Stiles was pulling back and taking Derek with him, rocking forwards again almost immediately. He was being used, used like the whore he was, and it made him shake within his skin. He’d never felt so well fucked, even after clients that left him boneless and sated, and it made him whine when John stopped it suddenly, hands landing on his shoulders to hold him still.

He pulled off his cock for a moment, twisting his head to look up, a broken sound punching out of his chest at the sight of Stiles and John kissing above him. Derek could see wet flashes of tongue, the two practically devouring each other’s mouths, and it made him want so badly he swallowed down John’s cock once more just so he didn’t beg for the same. He was just a tool, just an extra set of holes for them to fuck each other through, and that thought--despite his distaste for his job in general--had his cock pulsing between his thighs.

It didn’t last long, Stiles picking up his thrusts once more, Derek choking as his throat was brutally fucked. Stiles was whining, little sounds escaping with each pump of his hips. All of it, every thrust and groan, culminated in Derek’s chest until he was on the very edge, cock jerking like it wanted to spill without a hand on it.

“Gonna come? Gonna come without anyone touching you, come like a little slut, just from us fucking you? Come on. Wanna feel you clench down on my cock.”

Derek wanted to obey, wanted to so badly, but couldn’t. There was an edge he couldn’t cross, a gap between where he was and orgasm, and it nearly made him sob. He’d never wanted to come so bad, never wanted anything in his life more than he wanted to make these two happy.

Oddly enough, what made it happen was Stiles. There was a sob from behind him, a rough thrust of hips, and then Stiles broken voice was sobbing out “Daddy” and Derek was gone. He shook and shuddered, pulling off John’s cock just to breathe as he spilled onto the sheets. Stiles slumped over his back, a heavy weight, and it made Derek whine, tilting his head to bare his nape.

He was so blissed out, so come dumb, that it took him a moment to realize John was pumping his own cock. Derek didn’t have the energy left to lift his head, let alone go at it like he wanted to, so he merely opened his mouth and stared up at John, pleading with his eyes. The man groaned before those blue eyes went dark, wet warmth shooting across Derek’s cheek. He purposefully moved, stretching his tongue out to catch a spurt of it and swallowing with a grin at John’s filthy curse.

 

.o.

 

“Thanks for this.”

Derek quirked a brow at Stiles, suddenly shy and half-way behind John’s bulk, rubbing at his neck as his cheeks slowly colored. He tossed the towel he’d been using to dry himself off with down onto the bed, nodding with a grin.

“Anytime. And I, I mean that. You two are...pretty good fucks.”

The way Stiles’ eyes lit up at the praise made Derek think maybe this wouldn’t be a one time thing, and he warmed at the idea of maybe getting to fuck these two again.

“Here. S’all there, count it if you want, I won’t be offended.” John held out a stack of cash and Derek obediently flipped through it.

He’d gotten ripped off before. Whether it offended them or not, Derek always made sure to count his cash before they left. But when he counted to his price and beyond, he stopped short and looked up at the two who were shrugging into their jackets.

“This is more than what I quoted you.”

“Yeah, well, you did a little more.” John’s eyes were kind and soft, though his tone told Derek there was no way he was taking any of the money back. “If that rankles you, consider it a tip for fantastic service.”

Stiles’ laugh was low and slightly uncomfortable and Derek couldn’t help but grin, holding up the cash in a salute and waving as they strode from the room. He settled back on the bed gingerly, pulling his phone from his own jacket and calling Erica as he stared down at the cash in hand.

This would be more than enough to pay his rent and maybe indulge in a restaurant or two for dinner this month.

“Derek? Everything go okay?”

“It was fine.” Perfect, amazing, wonderful. “Do me a favor, if those two call back, tell me immediately.”

“That good, huh?” Erica’s grin was evident through the phone and Derek, for once, returned it, thinking of the pleasant ache in his throat and ass that would likely serve as reminders when he went home tonight and fucked himself to the memories.

“You have no idea.”

Notes:

Hope you guys liked this! I tagged it in the order of the pairings as they take place in the story but if you think I should re-arrange the pairings or add some tags, feel free to let me know!

If you wanna come scream with me about Teen Wolf DILFS or anything, I'm momomomma2 over on tumblr as well!