Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/8025403.
  Rating:
      Explicit
  Archive Warning:
      No_Archive_Warnings_Apply, Underage
  Category:
      M/M
  Fandom:
      Teen_Wolf_(TV)
  Relationship:
      Derek_Hale/Peter_Hale/Scott_McCall/Stiles_Stilinski
  Character:
      Derek_Hale, Peter_Hale, Stiles_Stilinski, Scott_McCall
  Additional Tags:
      Boypussy, Sex_Toys, Anal_Sex, Mental_Chastity, Cunnilingus, Blow_Jobs,
      Knotting, Alpha_Derek, Alpha_Peter, Competitive_Behaviour, brief_sciles
  Stats:
      Published: 2016-09-13 Words: 2777
****** Nothing Like a Little Sex Competition ******
by Ookamisan
Summary
     Stiles and Scott being sexually competetive bottoms.
Notes
     I'm not even gonna pretend like I beta'd this. I hardly read through
     it myself. Have fun and may the grammar gods be with you.
Stiles and Scott sat dutifully in the middle of the carpet as Peter made his
way to the couch, followed by a man darker than him and nearly as big.
"Pups, this is my nephew, Derek. I hope you show him respect and how
accomodating we can be." Peter made a pointed look towards Stiles.
Stiles had zero problems with "accomodating" this fellow. Of all the guests
Peter had brought home, Derek was certainly the best looking with his beard,
scowl and grumpy red eyes. Stiles was going to make it his duty to break that
stare.
"Stiles you will tend to Derek first. Now come here."
Stiles and Scott immediately darted forward to their suitors, Scott unbuttoning
Peter's jeans while Stiles tackled Derek's massive, black leather belt.
Peter smirked at their exuberance. "Let's make this a contest yeah? Whoever can
take the most gets a new toy."
Derek side eyed Peter.
Scott and Stiles glanced at each other and nodded.
"Good. Continue."
Scott dug his hand into Peter's pants and pulled out his cock, immediately
taking the tip into his mouth. Peter was stupidly thick. His cock was a handful
as well as a mouthful when limp.
When Stiles finally got his hand around Derek and pulled his cock out, he
gulped. He wasn't as thick as Peter, but he was already half hard, the head was
more flared than Peter's and Stiles knew he was going to have a challenge
getting that down his throat.
Stiles took the tip into his mouth, sucking hungrily and licking along the
underside. Derek filled quickly, relaxing into the back of the couch.
After a moment Stiles heard a wet choking sound and turned to see Scott already
have Peter half way down his throat.
Peter moaned appreciatively and gripped Scott's curls, thrusting minutely a few
times before letting him up.
Stiles turned his attention back to Derek and tried taking him further. As soon
as Derek's flared head reached the back of his throat he gagged and had to pull
off. He tried to keep Derek interested by stroking him and glanced up
nervously.
To his horror Derek was looking disappointed; watching him with disdain, head
resting on his palm like he was bored.
Stiles saw out of the corner of his eye, Scott's head bobbing a large portion
of Peter's cock. He tried again to take Derek down his throat but failed.
Whimpering in desperation, he licked and sucked around the head, stripping
Derek's cock with firm, twisting strokes.
Derek's expression didn't change much.
"Jesus, slow down Scott." Peter growled, digging his claws into the couch in an
attempt to not grab Scott's head.
When Scott didn't waver, Peter growled again and firmly pulled him off by the
locks. "Switch me, Derek. You'll get a good time out of Scott. I need a
breather."
Stiles pouted and took Peter's sloppy cock into his mouth. Peter was still
massive but the tip of his dick wasn't as flared nearly as drastically as
Derek's. Stiles at least got a little more than a quarter of Peter down his
throat.
Derek let out a moan as Scott managed to swallow the tip of his cock, and
Stiles accidentally dug his nails into Peter's thigh.
"Yikes!" Peter pried the nails out from his thigh. "Is someone jealous? Worried
Scott is going to be the favorite?"
Stiles tried to force more down his throat in a rush, gagging viciously.
Suddenly he heard Derek groan loudly, and Stiles looked to see Derek holding
Scott's head by his chin and the back of his head. Derek's balls drawn up tight
as he pumped Scott full.
Stiles stared as Scott slowly pulled off, mouth full with a smirk on his face;
a thick string of cum attached from his chin to Derek's wilting cock.
"Scott wins." Peter pats Stiles on the head somewhat patronizing. "Looks like
you'll have to up your game."
Stiles nipped him on the tip and earned himself a month of chastity.
---
It was a few days later that Peter brought Derek back again, and reintroduced
the idea of making it a contest.
Scott puffed his chest out with pride and Stiles huffed before making their way
to Peter and Derek's lap.
"Try and make it up to Derek, Stiles." Stiles mimicked Peter silently. Myeh
myeh myeh.
Derek swiped him on the back of the head with his large hand. "Don't push it
pup." Undoing his trousers himself and pulling Stiles to his cock.
Stiles stared with wide eyes as the flared head was shoved into his mouth. That
was the first time he had heard Derek speak, and his voice gave Stiles chills.
Stiles did his best to tune out Scott and Peter. This wasn't a race. He just
had to focus on taking Derek down his throat. It was very hard to ignore them
however when Scott was making loud slurping noises followed by Peter's praise
while Derek was completely silent.
Stiles shoved his hands into the confines of Derek's pants, and cupped Derek's
balls, one in each hand.
That got a response from Derek; a small chuff of surprise. When Stiles looked
up, he saw Derek staring down at him, a small blush in his cheeks, mouth
parted.
The image made Stiles's clit pulse and he whimpered because while he didn't
have an actual chastity on, he knew Peter would bruise his ass if he tried to
pleasure himself, let alone sit on Derek's dick.
He continued fondling Derek's balls, rolling them in the loose skin as he
managed to take Derek a little further down his throat before popping off to
take in air.
Derek groaned and his cock a deep red and twitching in the cold air. Stiles
beemed.
"Oh fuck yes, Scott." Peter growled, and Stiles turned to see Scott straddling
Peter's lap, back to chest as he sunk himself down onto Peter, taking him
almost all of the way in.
Stiles slammed his fists on the couch.
You cheater! I can't do that!
Scott rolled his hips as he fucked himself on Peter's cock, quickly bringing
them both to climax.
"Looks like Scott wins again." Peter said hoarsely.
---
This wasn't fair. Scott knew Stiles was on chastity. He'd have to figure out
how to beat him.
Then he realized. Scott wasn't able to take Peter all the way even in his cunt.
His body was just too small. His ass however? Peter never said his ass was on
chastity. They had dabbled in anal before, what could the worst be?
Ow ow ow owww! Stiles thought, clapping his hands over his hole when he tried
to take in a large werewolf dildo later that night that was always kept in a
cupboard, complete with knot. Peter had said it was something they could work
up to in the future. Stiles had managed to part his rim about an inch before
feeling a burning, stabbing pain and having to pull off.
This was going to take some work. He thought as he stifled sniffles into the
carpet.
Stiles took any time that he could while Peter was away to try and work onto
the dildo. Locking himself away from Scott. He claimed to need a bath, and was
currently running the bathtub while he kneeled on the tiled floor. He had
coated the dildo in lube and managed to awkwardly finger his hole open with two
of his own fingers. He kneeled over the tip, and slowly sunk down onto it. He
was surprised when the head popped past, and he had to stop for a moment,
taking deep breaths.
After a moment he let gravity take him a couple inches further down, and
grimaced at the burn as well as the alien feeling of pressure in his pussy
while nothing was in it. He slowly worked the few inches of the toy that he
could comfortable fit for several minutes. Soon the ache was too much and he
had to quit, standing up and trying to ignore the burn as well as the low-key
arousal in his pussy as he made use of the full bath tub.
It was about a week before Stiles was capable of taking the dildo the way he
wished. Peter brought Derek around a couple times during that but laid off the
competition spectacle for simple pleasures while they endulged in alcohol and
television.
Stiles was shocked when he felt his rim touch the knot, pressing his fingers to
his abdomen to feel the tension and pressure. His pussy was drooling, clit
swollen and red. Stiles had to bite his fists to hold back from touching
himself.
He braced himself on his hands and knees, rocking his hips up and down, biting
back his moans as the tip of the dildo pressed deep and manages to stimulate
his cervix. It felt like he was getting fucked in both holes, and he was
desperate to feel something in his pussy.
His face burned red as his pussy continued to drool onto the tile, his clit
pulsing painfully the deeper he went.
After several minutes, Stiles was grinding down on the knot, trying to work it
in as pressure in his abdomen built.
Panting, sweaty and shaking, he opened his mouth on a silent moan as his rim
spread wide over the knot, enveloping it half way down. The burn made his clit
pulse, pussy clench and suddenly he was cumming, hard.
Stiles had to hide his face in the tiled floor as his ass and pussy milked
viciously on the dildo. A faint sound of liquid spurting could be heard with
every clench, and when Stiles finally caught his breath and the ringing in his
ears passed, he lifted himself up to see that he had apparently squirted a
small mess.
All too quickly the burning became too much and his ass urgently bore down and
he was forced up and off the dildo, a loud schworp sound following, as well as
a small, unintentional trickle of pee.
Stiles collapsed to the side, ass burning, pussy aching and he felt utterly
smug.
A couple days layer, Stiles found himself once again at Derek's feet, feeling
confident in himself. He held eye contact with Scott when he took Derek's
cockhead in his mouth. Clearly making a challenge.
Scott squinted at him as Peter snickered, then nodded.
They began their usual blowjob routine, Stiles focusing on bobbing his head and
taking it as deeply as possible. He was getting better if Derek's deep exhales
through his nose meant anything.
Derek was getting close, Stiles could tell as his cock swelled, skin at the
base going tight and thin as his knot began to inflate.
Scott pulled off of Peter sloppily, pulling up his nightgown to quickly seat
himself on Peter's cock, taking it until Peter's knot bumped against him. He
seemed pleased with himself, sure on his win.
Stiles slowly and torturously pulled off of Derek's cock, who flinched at the
stimulation. When he lifted his own gown, turning away from Derek, Derek's eyes
grew wide and Peter snapped his fingers.
"You're on chastity, Stiles!"
Stiles ignored him, which was a big risk, and backed up until he was sitting on
Derek's lap, cock pinned under his cheeks.
This whole act of using his ass was a risk. He knew Peter would probably punish
him heavily. He grabbed Derek's soaked cock and pressed the head to his already
stretched and wet rim. When he sunk down, both he and Derek groaned. Derek
throwing his head back into the couch, clutching at his hips.
Scott stared, dumbfounded as Stiles sat on Derek's lap, having taken his entire
cock into hiss ass. Deeper than what was possible in his pussy.
Peter let out a laugh and ruffled Scott's hair, "Looks like you've been
outdone, Scott." And proceeded to shock him out of his stare by wrapping his
arms around his waist and fucking up viciously.
Stiles was already aroused during the blowjob, imagining that he would get to
take Derek inside him. His pussy was drooling excessively, clit hard and
protruding from his mound as Derek rolled Stiles's hips in his large hands,
growling and grunting from the heat and constriction of Stiles's ass.
Stiles's eyes rolled back in his head. Derek's cock was longer than the dildo,
and was thoroughly stimulating his vagina from his ass. He whimpered and shook
as Derek's knot swelled, locking them together.
"Fuck, you dirty brat." Derek growled in Stiles's ear, grabbing him by the chin
and pulling him to press against Derek's chest. He began rolling his hips up,
stimulating Stiles by the pressure of the pull and push even though he wasn't
really moving.
It seemed to be plenty for Stiles, however, who was already in tears and red-
faced as the knot bulged so much that Stiles's pussy was inflamed, flashing
it's dark pink interior.
"You gonna cum from your ass, Stiles? Cum on my knot like a good brat?"
Stiles nodded desperately, quivering and crying.
Derek reached down and wiped his fingers along Stiles's pissy, gathering the
lubricant. Stiles flexed his toes at the stimulation on his sensitive skin, and
cried out, throwing his head back on Derek's shoulder as Derek began rubbing
and massaging Stiles's clit.
"Fuck, yes, Stiles. Cum on me." He grunted as Stiles immediately began to
clench on his knot. The clenching quickly turned rhythmic as Stiles sobbed
openly, and then turned into a mean beat as Stiles screamed through his orgasm,
pulling Derek through his orgasm as well.
Stiles thinks he has blacked out, because when he opens his eyes, Peter is
standing above him and Derek, Scott discarded with a pussy full of cum beside
them on the couch.
Peter kneels down between Derek's legs, staring at the obscene mess they've
made. "You're right, Derek. Stiles is very, very naughty. I wasn't planning on
teaching him anything to do with anal for a long time, and yet here we are. And
look at this desperate cunt." He slips two fingers into Stiles's pussy, making
him whimper. When he crooks his fingers, both Derek and Stiles gasp.
"Ow, quit moving!" Derek growls as Stiles begins to desperately hump into
Peter's hand.
Peter stands back up, taking his still hard cock in hand, and slides as far as
he can into Stiles's pussy with a pained growl.
Derek can't believe the heavy pressure on his cock, and his cock gives another
pulse, still hard and locked inside Stiles.
Stiles yells at the feeling. It's like his ass and vagina have now become one
and he can't tell what's what. He feels like he is going to burst and the
pressure from every angle is intense.
Peter begins fucking into Stiles sloppily, balls slapping against Derek's.
Stiles is beyond crying and goes straight into mindless moaning, eyes rolling
as it feels like he is already cumming, but instead of contractions, it's one
long burn that builds and builds in a non-stop ascend that leaves him
breathless and tight as a drawstring. Right when he thinks he may actually die,
Peter presses his thumb on his clit, viciously rubbing and pressing and Stiles
goes limp as all the tension shoots into his abdomen. His orgasm is painful and
he hears a rhythmic psshh psshh psshh as he squirts in currants that deluge and
spray off Peter's hips.
Both Peter and Derek roar, eyes going red and faces shifting as Peter pulls out
enough for his knot to form, preventing him from knotting Stiles and then slam
home.
Stiles was barely conscious for a good hour while Derek and Peter eventually
worked their way out of him and cleaned him up, putting him to bed.
When Stiles woke up this time, it was because there was a new tingling
sensation in his clit and he was worried he was going to wet the bed.
When he opened his eyes, it was dark in the room, and he became aware that he
must have been well and truly exhausted.
The unmistakable sensation of a mouth and tongue massaging his clit had him
shakily lifting up the comforter, to see Scott between his legs. His mouth
enclosed over Stiles's mound, furiously milking and suckling him into a sloppy
mess.
"S-Scott?" Stiles whispered.
Scott pulled up with a deadly glint in his eye despite there being no light in
the room. "Teach me how to do that, and I will do this for you every night
while you're on chastity."
Stiles moaned, dropping the comforter and spreading his legs as Scott hauled
his hips closer to his face.
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