Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/2545202.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/John_Winchester/Sam_Winchester, Dean_Winchester/Sam
      Winchester, Dean_Winchester/John_Winchester, John_Winchester/Sam
      Winchester
  Character:
      Dean_Winchester, Sam_Winchester, John_Winchester
  Additional Tags:
      Crossdressing_Dean, Halloween, Spitroasting, Oral_Sex, Anal_Sex, Riding,
      cockslut!Dean, schoolgirl!Dean, Anal_Fingering, Teasing, Edgeplay,
      Sibling_Incest, Parent/Child_Incest, Underage_Sex, probably_some_other
      tags, I_don't_know, it's_sexy, just_saying, oh_yeah, i_forgot, Daddy
      Kink, and, Dirty_Talk, that's_it_for_now, i_think
  Series:
      Part 14 of Holidays_with_the_Wincesters
  Stats:
      Published: 2014-11-01 Words: 1970
****** Trick or Treat (A Wincest Halloween) ******
by callmeb, MothMeetsFlame
Summary
     Dean's a schoolgirl for Halloween. Sam and John are making it
     naughty.
Notes
     This, my friends, is the final installment of Holidays with the
     Wincesters. I know... sad to see it go *wipes away tear* But! There's
     still this lovely little fic to enjoy. And everyone give a big ol'
     thank-you kiss to my collab partner, B. She's awesome, just saying.
     Enjoy ;)
See the end of the work for more notes
Dean bit his lip and moaned. His pleated skirt flew out with every drop onto
the thick cock inside of him, tickling his head while he rode his little
brother.
Just these last few months, Sammy’s cock got huge, bigger than John’s even, and
Dean couldn’t even deny how much he loved getting stretched open on it. If
there was anyone who came even close to being the cockslut Sammy was, it was
Dean.
He loved getting fucked open on John’s monster cock, but he always loved it
more when Sammy was the one fucking himself back on their daddy’s rigid shaft,
the cock disappearing inside of him while his little ass just swallowed it up.
Sammy was all lithe muscles and whimpering pleas while he took it every way
imaginable, and as much as Dean loved having their daddy’s cock in his ass, it
didn’t even compare to watching his little brother ride him.
But then, his little brother wasn’t so little anymore. His cock grew, fucking
thick and long and uncut, into a masterpiece. It became a compulsion trying to
take his not-so-little brother into his throat, wanting to feel it thrust deep
inside of him, to feel it split him open while he writhed beneath his little
brother, payback for all the times he'd done the same to Sammy.
And Sammy loved to make his big brother ride him too, loved making Dean show
how badly he wanted it, watching Dean put all his weight on Sam's lap,
grinding, rutting, especially dressed as pretty as he was.
One look at Dean’s schoolgirl outfit—white Oxford shirt tucked into his plaid
skirt, black stockings leading them to what Sam could only describe as the
tallest hooker shoes he’d seen—and both him and John took hold of him to share
him between them instead of trick-or-treating with the rest of the town.
Sam pulled Dean in roughly, and Dean practically fell on his little brother,
straddling his hips while John fed the tip of his cock into Dean’s mouth.
Sam’s view was amazing, and he relished in having Dean ride him, mostly because
his big brother whimpered pleas around their daddy’s cock while he did it,
unable to make his muscles work well enough to fuck himself on Sammy’s rigid
shaft like he wanted to. 
Dean moaned, the vibrations making John gasp and thrust deeper into Dean’s
throat. Dean nearly gagged before he controlled himself and took his daddy
deeper. He loved it when he lost control and fucked his throat, precome and
spit making his mouth sloppy wet. But he also loved to be fucked hard and fast,
to be held down and pounded into.
Sam enjoyed it, too. He loved watching Dean struggle to take his cock, loved
how his eyes squeezed closed as he seated himself in his little brother’s lap,
panting because Sammy’s cock was always hard to take no matter how much they
prepped his little hole. And when Dean began the slow rise and fall to accustom
himself to his brother’s size, his thighs trembled with the movement, and Sam
knew that Dean wouldn’t be able to keep it up for long, that he’d need his
little brother to fuck roughly into him.
The assault of his brother's cock against his prostate was too much for Dean to
take, leaving it up to Sam to move, to grab Dean's hips and thrust into him
from below, but not before he made his big brother beg for it.
Dean braced himself on Sam's chest, shaky but still whimpering with every
twitch of the cock inside of him, trying to push himself back to take more. He
tried not to beg, but Sam’s thrusts were too slow, too shallow, because Sammy
wouldn’t give it to him completely until Dean begged for it.
Dean pulled the cock out of his mouth, much to John’s dismay, and pumped it
loosely while he whined. "Please Sammy—unh— Just fuck me. Sammy, please. I need
it—fuck."
And Sammy couldn’t help but tease him. He slipped his hand under Dean’s skirt
and thrust a finger into Dean's ass right next to his cock, not doing anything
to give in to Dean's pleas, still keeping his thrusts shallow and teasing. He
couldn’t help but gawk when his brother was like this, half fucked-out and
whimpering with need.
"God, Dean, you really need it don't you? Need your little brother's cock, love
how it feels inside you. How much do you want it, Dee? How bad do you want me
to fuck you?"
Dean begged so pretty for his little brother. Back arching, hips trying to push
Sammy's cock even deeper. John’s cock slipped out of Dean’s grip when he moved
to stop boy's hips from taking Sam's cock fully inside him. "I think Sammy
asked you a question, Dean."
"C'mon Sammy please just..." He cut himself off and bit his tongue. He wasn’t
going to beg for it, could hold out a while longer before it came to that. He
was sure of it.
John’s hands held tighter to Dean’s hips, not letting him move even an inch,
though Dean was trying his hardest.
"No, Dean. Not until you answer your brother."
Dean shook his head no. He grinded his hips down harder trying to force more of
his brother's thick cock inside of him, but John's hands held steady.
"Answer the question, Dean." Sammy smirked and continued teasing Dean’s hole,
thrusting in so slowly that it could hardly be considered movement.
Dean moaned when the head of Sammy's cock rubbed against his prostate. The
quick brush was all it took to tear down his will. "Fuck, yes, love it, Sammy,
please. Need it. Want it all the time, so much. Mmmm… Want you to fuck me so
bad, Sammy, please."
"Mmm, can't hear you loud enough, Dee. Say it again."
Dean moaned and held himself up over his brother, half out of his mind with a
need he'd no doubt deny later. "Love it, Sammy. Fuck, love your cock. Want it
in me all the time. Please, fuck, please more. God I need it so much, Sammy.
More. Harder. Want it so bad."
"There's a good boy,” John praised. Wet lips touched themselves to the back of
his neck for a moment. “Go on Sammy, give your big brother what he needs."
And Sammy may not have always done what he was told, but he had no intention of
disobeying the order. He thrust deep into Dean's slick hole, making him keen.
Dean collapsed onto Sam's chest, whimpering with every deep thrust. His cock
leaked hard between them, the friction against Sam's stomach increasing with
every piston of his hips.
He was so close to bursting that he couldn’t help but pant. His mouth moved to
form words that wouldn’t make it past his lips. So close, Sammy, he mouthed.
Please, more, please, more, pleasemoremoremoremore.
And Sammy fucked in harder, faster. John held Dean's hips tight and made him
meet every thrust, practically bouncing his boy up and down on Sammy’s cock.
"Ohgodohgodfuckfucksammyplease"
"That's it Dean. Take it. Fuck, Dean, want you to come with me. Want you to
come when I fill you up."
Dean whimpered and moaned into his brother's neck as his ass was pounded into.
John moaned from behind them. "Can you do that, baby boy?” he asked. “Can you
come from your little brother's cock? C'mon, Dean. We know you love how
stretched open you are."
"Fuck, Dean!" With Dean’s whimper, Sam came inside of him, stuffing him full of
come that he promised to clean out of his brother's sloppy hole later. His cock
pulsed while he fucked himself through his orgasm, and spurt after spurt shot
inside of him.
Sam's muscles tensed, and his stomach once again brushed Dean's cock, this time
keeping steady pressure as Dean impulsively writhed. Come shot into Dean’s
skirt, coating the plaid with white tendrils of his release, and his back
arched with the force of it. He collapsed against his little brother, come
leaking through the fabric to soak Sam’s stomach, as both of them panted with
exertion.
John soothed his hands down Dean's back and reached down between loose limbs to
rub Sammy's tired sac. "Shhh boys. You did so good. But Daddy can't wait any
longer. I think Dean deserves some more. What do you think? You want another
fat cock in you?"
Both his boys whimpered as John lifted Dean's hips up again. Sammy's softening
cock slid out, followed by a small trail of come. Dean hissed, but he still
pushed back when John lined the head of his cock up with his sloppy hole.
Dean couldn’t move, couldn’t speak to tell his daddy that, yes, he craved his
cock like he craved Sammy's, that he wanted it inside of him, filling him up
with more come. Instead, he moaned, low and deep, and John knew just what he
wanted.
"Don't worry, baby boy," John soothed. "I know what you want."
John pushed in until the head of his cock was nestled inside, and he moved as
gentle as possible, Dean crying out in a mixture of pleasure and pain.
"Shhh. That's it. That's so good Dee. Let Daddy take you. I'll give you what
you need, baby. Just want you to beg for me one last time. Beg for me and I’ll
pound your sweet ass so good. You want that, don't you?"
But still, Dean could hardly speak. He groaned into Sammy's neck, arched his
back to take more of his father.
"He wants it, Daddy. He wants it so damn bad."
Dean worked up the strength to nod his head, and that seemed to be good enough
for John. He thrust in quickly, fucking his son with abandon, feeling how slick
he is from the mix of spit, lube, and come. It fueled him to drive in deeper,
drilling Dean's ass as his son involuntarily cried out, his over sensitive
prostate completely abused.
Dean's fingers clawed at the bedding around Sam's shoulders. Small, whimpers
and sobs tore from his throat as his ass was pounded. "Please" he rasped out in
to his little brother's sweat-soaked skin.
And Sammy knew his brother's pleas like he knew his daddy's cock. He reached
between them and thumbed over Dean’s head. His cock was flaccid between them,
over-sensitive since he’d just come, but Sam knew that his brother loved it,
loved being forced to take whatever they gave him.
Dean's hips twitched and he cried out, his brother's hand torturous on his cock
while his daddy pounded into him from behind.
He begged again, voice wrecked and shaky, "Please, da-daddy. Sammy, please!"
His son's voice was thick and hoarse, and it had its desire effect. John pulled
Dean roughly onto his cock and came with a shout inside of him.
Dean cried out as he was filled up again, so full. His ass clenched around
John’s cock, and his body shook. Sam played with Dean’s shaft, rolling the
empty sack with his fingers when Dean tried to pull away from him. It was so
much, too much. But it felt so good.
Sam wet his lips at the sight his brother made. His own cock was hard again,
teenage hormones bringing him back up quickly. It was his favorite thing, to
watch his brother pass out from being fucked over and over and over again,
watching him walk gingerly the next day because he'd taken his little brother
and his daddy into his ass so many times, practically fucking begged for it.
Sammy loved it even more knowing that he’d have no choice but to walk around
like this when they went trick-or-treating later. Nothing said naughty
schoolgirl like being stuffed with come. 
End Notes
     Aaaaaaaaaand that's all, folks. Let me know what you think :) And
     thanks-times-a-million to my friend, B. I hope everyone enjoyed the
     ride ;)
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!