Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4607724.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      High_School, Sibling_Incest, Underage_Sex, Top_Dean, Bottom_Sam,
      Cheerleader_Sam, Roleplay, Oral_Sex, Anal_Sex, Dirty_Talk, Praise_Kink,
      Size_Kink, Crossdressing, Rough_Sex, PWP, Plot_What_Plot/Porn_Without
      Plot, Shameless_Smut
  Stats:
      Published: 2015-08-19 Words: 2761
****** Go, Dean... ******
by MothMeetsFlame
Summary
     Prompt: Teenage Dean joining the football team and Sammy cheering him
     in the stands, Dean calling him his little cheerleader and making him
     wear the outfit while he rides his big brother... How's that for
     enduring football?
     "'Thought you wanted to be my little cheerleader, Sammy,' Dean said,
     tossing the gathered supplies onto the bed and crawling back between
     Sam’s legs. His lips sealed themselves to Sam’s, and he kissed him
     breathlessly. 'Loved watching you bounce up and down out on the
     field, everyone watching you, wishing you were theirs.'”
Notes
     It's been forever and a half since I talked about writing this fic,
     but it's here now. A big thanks to the magnificent Imagf for
     inspiring me :)
     WARNING: contains underage sibling incest and some rough sex and
     stuff that I'm too tired to add in this warning, but it's all
     consensual, so I guess maybe that's it? I dunno. Check the tags.
     Enjoy ;)
See the end of the work for more notes
Sam shivered when Dean’s lips grazed his neck. His head fell back, angling
enough to give his brother better access, and he wasn’t disappointed as the
movement sent a pleasured tingle down his spine. He wound his arms around
Dean’s waist, slipping them into the back of his pants to grope Dean's ass,
grinning in victory at his brother’s moan.  
“Loved watchin’ you at the game,” Dean whispered into his ear. “Jumpin’ around.
Cheerin’ me on. Like my very own cheerleader.”
Sam groaned, the sound low in his throat.
“Mmmm… You like that? Like being my cheerleader, Sammy?”
“Yeah,” he gasped. Shivers crawled down his arms, pebbling his skin.
Dean ghosted his lips over Sam’s jaw. “Yeah what?”
“Like it.”
“Like what, Sammy?”
Sam’s head swam, fighting to focus on Dean’s words. “Like being your
cheerleader.”
Dean grinned and lifted Sam by the thighs, displacing his hands with the
movement. Sam’s legs wrapped instinctively around his brother’s waist, bringing
their groins together. Dean moaned at that slightest bit of friction, drowning
out the small noises Sam made as he shifted in Dean’s grip.
His hands clutched at Dean's shirt, and Dean thrust against him, pulling Sam in
as close as he could. Sam’s breath hitched in his throat, and his mind blanked
out for a moment before he came back to himself. Even after months of this with
his brother, he still wasn’t used to how good it could feel, how every press of
skin could make his breath stutter even as he warmed to the touch.
Dean's hands were rough on his thighs, lips soft against his neck as he led
them to the bed. Dean laid him down and crawled between his legs, not losing
even the slightest bit of contact until Sam unlinked his ankles from around
Dean’s waist.
His feet found the edge of the mattress, and he used he position as leverage to
buck his hips up. Dean moaned and mouthed his way down Sam’s neck, leaving a
trail of fire in his wake. Dean nipped at his collarbone, sucked a small bruise
onto the pale skin, before pulling himself back.
Sam let out a guttural protest at the loss of contact, but Dean pressed his
lips against Sam’s once more to silence him. Dean took a moment lift his shirt
over his head before he rid Sam of his as well. It was moments before Dean’s
lips were back on him.
Sam’s breath came in panting gasps, little whispers of air sucked rapidly into
his lungs. His cock was hard in his pants, leaking slightly, and Sam could feel
it twitch whenever Dean found a new spot on his torso to lick and suck, bite
and kiss.
Sam’s lids fell closed as Dean lavished affection on his navel, every thought
in his mind focused completely on his brother’s mouth. It wasn’t long before
his jeans were undone and pulled down the length of his legs until they were
gone, but Sam hardly noticed with Dean lips mouthing at the cotton over his
small but proud cock.
Dean pulled down Sam’s cotton briefs, letting his cock bob in the cool air of
the room. He took his brother in his hand and licked over his slit, Sam’s eyes
flying open in shock at the sensation. His hips bucked of their own accord, and
his gasp cut off as Dean licked again.
“Unh, Dean!”
“What was that?” Dean teased. “I couldn’t hear you.”
Dean pressed his tongue against Sam’s slit and rubbed gently, picking up the
little beads that dripped from his head. Sam clenched his eyes close, the
sensation overwhelming him, and sparks filled his vision.
“De… mo… ah… please…”
“Please, Sammy?” Dean asked curiously. He sucked the tip of Sam’s cock into his
mouth and thumbed the sensitive underside of his cockhead, Sam’s gasps fueling
him.
Sam moaned as Dean took in another inch, still only half of his cock sucked
into his brother’s mouth. Sam tried to thrust, tried for more of the wet
suction that Dean’s mouth provided, but even though his muscles strained,
Dean’s hand on his stomach held him down.
Dean sucked gently as he pulled off of his brother’s cock, and Sam’s eyes
rolled into the back of his head.
“Got you something special,” Dean teased him. He sucked gently once more, and
Sam mewled.
“Something...?”
“Something for my good little cheerleader.” Dean grinned.
“Go, Dean,” Sam cheered breathlessly.
Dean chuckled as he engulfed his brother’s cock. His lips trailed down the
shaft, even lower than he’d gone before, sucking the entirety of Sam’s cock
into his mouth as a reward.
Sam’s back arched off the bed, every nerve in his cock shooting pleasure up his
spine.
Dean’s lips pulled up into a grin, and he sucked one more time before he pulled
himself off. He kissed the leaking tip of Sam’s cock in parting and slid off of
his brother, leaving Sam panting on the bed while he retrieved his supplies.
Sam lifted himself onto his elbows, eyes lazily tracking Dean around the room.
A low blush colored his cheeks when he saw what Dean had for him.
“Really, Dean?”
Dean smirked. “Yep.”
“Do I have to?”
“Don’t you want to?”
Sam’s lips pursed, but he didn’t answer.
“Thought you wanted to be my little cheerleader, Sammy,” Dean said, tossing the
gathered supplies onto the bed and crawling back between Sam’s legs. His lips
sealed themselves to Sam’s, and he kissed him breathlessly. “Loved watching you
bounce up and down—” kiss “—out on the field—” kiss “—everyone watching you—”
kiss “—wishing you were theirs.”
Dean’s hand came between them to stroke over Sam’s shaft.
“Thought about what you’d look like on my cock.”
Dean loosely stroked up and down as he kissed his brother, the grip just enough
for Sam to want more.
“Bouncing up and down like on the field.”
Sam moaned into Dean’s mouth.
“Your lips all red and swollen.”
Dean nipped at them, and Sam gasped, lips parting to let his tongue slip in for
a moment before Dean pulled back again.
“And I wouldn’t be able to keep from kissing you.”
Sam felt Dean’s breath against him, and he couldn’t help but shiver as Dean’s
grip tightened around his cock.
“So fucking sexy, Sammy.”
Sam wrapped his arms around his brother’s shoulders and thrust his cock into
Dean’s fist, lust pooling inside of him. Dean grinned, capturing his mouth in a
kiss, twisting his wrist at the end of each pull so he could swallow Sam’s
moans. It wasn’t long before Sam was breathless, panting.
“My Sammy. My cheerleader.”
Dean released Sam’s cock with a quick kiss as an apology, pulling back to
gather the outfit he’d bought for his little brother. Sam made a noise of
disappointment at the loss of contact, but Dean hushed him with another kiss
before pulling away again, unable to keep himself from staring at Sam’s leaking
cock and pink skin, lidded eyes and swollen lips.
Sam squirmed under Dean's gaze, flushed at the predatory look in his brother's
eyes, but before he could rush him, Dean grinned, clothes in hand: one pair of
white cotton panties, one red and white pleated skirt, and a red halter top
that looked two sizes too small.
He held up the pair of pom poms last, and Sam’s cock twitched at the thought of
becoming Dean’s cheerleader, of cheering him on and bouncing on his cock.
“You ready, Sammy?”
A glob of precome spurt from his the tip of his cock, and he nodded eagerly.
He held still and allowed Dean to manipulate his arms and legs into the skimpy
cheerleader outfit.
Dean slipped the top over his head first, leaving it just under his collarbones
while he licked over his sensitive nipples. By the time he pulled the top down,
letting it rest just under his chest, Sam could feel the scrape of fabric with
every shift.
“So pretty…”
The skirt was next. Dean slid it up his legs until it rested just above Sam’s
thighs. Sam lifted his hips, and once it was in place, Dean wasted no time
sucking his brother’s cock into his mouth, teasing Sam’s cockhead until he was
a whimpering mess.
Last but not least, Dean trapped Sam’s swollen erection beneath tight cotton
panties. His lips ghosted over his trapped cock, and Sam arched into the touch,
closing his eyes and letting Dean play with him. He hardly noticed when Dean
slipped the pom poms into his hands, he was so hard, leaking into his new
panties. He loved it, loved every touch, even as he begged for more.
“Please… Dean, yes, please...”
Dean’s chuckle made Sam squirm, and he gasped as Dean’s mouth sealed on the
fabric of his shirt, soaking it through. Dean suckled his left nipple until it
was a hard nub of sensation before he bit down down on the abused flesh.
“Don’t you want it?”
Sam whimpered.
“Huh, Sammy?”
He bit down again, and Sam cried out.
“You want it?”
“Yeah, Dean, please.”
Wet fingers moved his panties to the side and a thick digit slipped inside of
him. Sam gasped, and he held the pom poms tight to keep from grabbing Dean’s
hair.
Sam canted his hips into the touch, trying to get more.
“Just gotta be patient,” Dean soothed.
The first finger just gave him a full feeling.
The second gave him a little burn.
By the time Dean had three fingers pumping in and out of him, stretching him
wide, Sam could feel every single one of them inside of him, working him open.
His inner walls stretched and his cock soaked his panties through with precome
as his brother prepared him.
Sam’s eyes flew open in shock.
“Found it.” Dean chuckled.
Sam gasped, hips thrusting up, wishing for friction on his cock.
“Dean…”
The burn dimmed, but the fingers inside of him still seemed impossibly big. He
was full, but it was nothing compared to what it would feel like to have Dean’s
cock inside of him. The stretch he was feeling now would end, and then every
inch of him would be filled up by Dean, the thick member thrusting into him,
making him clench with pleasure.
“Dean, please…” Sam panted. “Please.”
Dean removed his fingers and captured Sam’s lips, swallowing a breathless mewl.
Sam whined into Dean’s mouth, cock stimulated by Dean’s body grinding against
his own. Dean pulled back and bit at the juncture between Sam’s neck and
shoulder, leaving his mark.
“So pretty, Sammy,” he murmured.  
Before Sam could reply, Dean flipped them, rolled them over so Sam could
straddle him from above. He reached up and tweaked Sam’s nipples, making him
hiss.
“God, Sammy.”
“Unh…”  
“You ready for it?”
Sam nodded, head swimming.
Dean unzipped his pants and pulled out his hard cock. The tip glistened with
precome, the head a dark, shiny red. Sam’s mouth parted in awe, and he sucked
in a breath at the site. He reached a tentative hand out to touch his brother’s
cock, stroking it slowly so he could feel the the quick pulse of a heartbeat in
the thickness.
Dean couldn’t keep his eyes away. He watched Sam’s pupils dilate when a bead of
precome pearled at the tip, watched him swipe over it with his thumb to slick
the way as he pumped his small hands up and down Dean’s shaft.
Sam gripped the base, and Dean moaned. Tight, but not tight enough. No
friction. Just the grip of his hand. But Dean almost lost it right then and
there.
In one smooth motion, Sam pulled his panties to the side and lined up Dean’s
cock, the tuft of a pom pom ticking Dean’s shaft as he sank down onto the thick
member—down, down, until his thighs were flush against Dean’s, the entire
length of Dean’s cock inside of him.
Dean moaned as Sam's hole took him in. His little brother opened up for him,
swallowed every inch and whimpered for more. Dean lifted Sam's skirt and
lowered his panties, pulled his cock out so he could see the flush of his
little brother’s shaft, completely filled with blood and dripping onto Dean’s
stomach.
Sam's cheeks were the same bright red as his cock, the color growing deeper
when Dean reached out to stroke his aching cock. Sam ground his hips down,
wanting more, but it wasn’t until Sam's inner walls clenched around him, hole
fluttering to accustom itself to Dean’s girth, Sammy breathlessly chanting,
“Dean, Dean, please, Dean, move,” that he grabbed Sam's hips and thrust into
him.
“Unnnnnhh… Deeeannn…”
Dean canted his hips slowly, Sam’s muscles too loose to help while Dean took
his time with his brother’s hole. Dean angled his cock, rocked into him again,
and Sam twitched, his breath caught in a half-stutter at the stimulation of his
prostate.
“Come on,” Dean said, keeping the slow pace. “I know you can do it. Come on,
Sammy. Cheer for me.”
Sam whimpered, but he dropped the pom poms to brace his hands on Dean’s chest
and lifted himself up, off of his brother’s cock, muscles trembling as the cock
inside of him brushed against his prostate when he dropped his hips.
He bit his lip and moaned, small noises of pleasure escaping him with every
rise and fall, Dean’s cock filling him up, pressing against that spot that had
heat pooling in his stomach.
Dean’s hands followed the motion of Sam’s hips as he rode him, skimming up and
down his sides, touching wherever he could.
Sam’s cock peeked out from beneath his skirt, dripping wet and smacking precome
onto Dean's stomach with every bounce of his cock.
Dean’s cock speared him open, and Sam whimpered at the feel of being stretched
to his limit, pain and pleasure mingling until he was on fire, heat leaking out
of every pore.
“Such a good little cheerleader, Sammy.”
Sam moaned.
“Couldn’t stop thinking about you on the field. Kept wanting to see you like
this, riding me.”
Sam’s hips stuttered, but Dean’s hands were there to keep him from stopping
completely.
“So fucking sexy. My little cheerleader.”
“Yours…” He was so close.
“That’s right. Mine. Love cheerin’ me on, telling me to go bigger—” thrust “—go
faster—” thrust “go harder—” thrust.
Sam keened.
“Come on, Sammy. Cheer for me. Let me hear you.”
“B -bigger.”
“What, Sammy? I can’t hear you.”
“Go… bigger…”
“Hmmm?”
“Bigger,” Sam repeated. “Faster.”
Dean rolled Sam off of him and flipped him over onto his stomach, lifted his
hips up just enough to slam into him as deep as he could go. Sam cried out at
the change of position, moaning as Dean laid into him.
He thrust in quickly, cock barely sheathing itself in Sam’s hole before he took
it out to the tip and shoved again, any sign of gentleness completely gone with
Sam’s keens of pleasure.
Sam fisted the sheets, scrambling to keep himself steady as Dean took him from
behind.
“Harder,” he cried out. “Faster… harder…”
Dean pulled Sam’s hips back into every thrust, pounding into him as hard as he
could. Sam clenched his eyes shut and tried to meet Dean's thrusts as his cock
pistoned in and out of his clenching hole.
“Fuck, Sam!”
Come splashed inside of him. Sam could feel a spattering wetness fill him up,
even deeper than Dean’s cock could reach, and the slide inside was even
smoother than before, Dean’s hips still forcing his cock inside as fast as he
could, riding out his orgasm.
Sam reached between his legs and stroked his cock, cheek pressed against the
mattress while his brother fucked into him.
Sam’s shaft was sensitive, the head of his cock leaking onto the mattress while
he stroked himself to completion. With a cry, Sam came, and his cock painted
the sheets beneath him. He couldn’t help but sink against the mattress,
twitching in Dean’s grip, every thrust sending small waves of pleasure through
him.
Dean slowed, panting, and pulled out slowly.
Sam winced when the head of Dean’s cock passed through his rim, stretching it
one last time before there was nothing but come and lube inside him. Dean
molded himself to Sam’s back and nuzzled his neck.
Sam shivered pleasantly with every small kiss Dean left him.
“Next time, you get to be the cheerleader,” Sam murmured, eyelids heavy.
“Mmmmm… my little football star.”
Sam could feel Dean’s grin against his neck.
“Gonna show me how to play ball, Sammy?”
End Notes
     You wanna know who's awesome? You.
     You wanna know what else is awesome? Comments! Yay, comments!
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!