Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/5443883.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      Multi
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester, Castiel
  Additional Tags:
      De-Aged_Dean, Semi-Public_Sex, Blow_Jobs, Anal_Sex, Anal_Fingering,
      Spitroasting, Bottom_Dean, Top_Sam, Top_Castiel, Sex_in_the_Impala,
      Threesome_-_M/M/M, Size_Kink
  Stats:
      Published: 2015-12-17 Words: 4336
****** Meet Me Halfway ******
by DickBaggins
Summary
     Sam is fed up with Dean; cursed back into his fifteen year old body,
     his overactive teenage dick won't give them any peace so he calls in
     Castiel to help babysit. This backfires immediately as Dean strives
     to prove he can still handle the both of them.
Notes
     Based on this prompt: Wincestiel featuring deaged!dean. Sonsofbitches
     won't believe he still can take care of them. Immoral persuasion and
     proof of capabilities is are in need, and Dean will deliver.
     Hopefully, he didn't talk too big... (Thinking of car sex on a
     deserted parking lot and spitroasting and/or DP? Cause I surely am.)
This was the worst.
Dean squirmed in the front seat between Sam and Castiel, drenched in their
totally grown up body heat, in their very manly smells. Towering over him, even
sitting and Dean felt way smaller than his de-aged body. Couldn't cut himself
open and count the rings, so he was pegging it at around fifteen. When he was
actually fifteen and not just shrunk down, he hadn't seemed so small at all,
but the first time around he didn't have an overgrown brother and an angel on
either side of him.
God, they're hot.
They're always hot, but especially now, it's just the worst.
 Dean's been hard on and off since the new body kicked in. It's mostly
uncontrollable and really hair trigger and he doesn't remember  that  from
twenty odd years ago. In and of itself, not terrible. What's really shit is
that Sam refuses to deal with it. Dean tried everything, tried crooning dirty
talk in his brother's ear, but his voice broke and Sam laughed. He tried laying
his head in Sam's lap but apparently that was too 'unsafe' and 'distracting'
while Sam was driving. He even got his angry-hard dick out and started rubbing
it against his brother, and that's when he called in the angel to help.
“Like a fucking babysitter,” Dean grumbled, but the press of Cas next to him
really did nothing to check his behaviour. Dean shifted closer to him, wound
his arms around one of Cas's, let his head dip onto his shoulder. “You'll be
nice to me, right?”
“I...always try to be nice. I thought so, at least.”
“He means - “
“Don't tell me what I mean,” Dean bowled over Sam, shot him a glare before
nuzzling at Cas's stubblesome neck with his own baby-smooth cheek. Lovely odd
sensation that drew out a slightly embarrassing moan from Dean and his voice
cracked with it.
Cas was not reacting, Cas was stone-stiff and darting eyes and bobbing throat,
nervous gulp. Hands in his lap, clasped.
Sam cleared his throat. “We should be focusing on reversing this spell, not
grab-assing, Dean. Leave Cas alone.”
Undaunted, Dean slid his hand down Cas's arm, wrapped the angel's hand in his
fingers and shit, the size of them, the bigness, roughness, it wasn't even
fair. They were both so fucking huge now and all Dean wanted was to get railed
until he couldn't see straight.
“Cas, here,” Dean said quietly, so his voice didn't break again, tugging Cas's
hand towards him, guiding it to the hard jut in his pants, “Just touch me a
bit, it won't even take long.”
It wouldn't; five, ten seconds, Dean flew past embarrassment long ago, just
needed to get the fuck off. Cas squeezed and Dean's whole body bucked into it.
Cas kept going and all the air left Dean's lungs and his dick throbbed so hard
he saw stars.
“Get my pants off, c'mon,” Dean rushed out, didn't even wait for Cas to comply
before he was undoing them himself and shoving against Cas's hand.
“Oh my god, Dean, put it away,” Sam groaned, watching the intersection like a
tennis match, red light stopped and, “Someone's gonna see. Cas, someone is
going to see your hand down a kid's pants - “
“I'm not a kid, jesus,” Dean hissed, wished Sam would shut the fuck up so he
could enjoy this. Cas's concerned thoughtful face was priceless but his hand
knew what to do, and anyway, Dean was humping up at it more than waiting for
the strokes so that worked just fine.
“You look like a kid,” Sam reminded him, tires screeching at the green and a
sudden turn, sending them careening faster than he usually drove. “Like,
fifteen, maybe sixteen and not even an old sixteen, not like sixteen with a bad
moustache, and you're taking advantage of Cas - “
“He's not,” Cas chimed in, fast, and Dean resisted the urge to stick his tongue
out at his brother. “He said it would be quick, Sam.”
They kept on talking and Dean heard none of it. Nothing. Cas's big fingers
tugged at him just right, strong, even-tempo. Dean's pulse pounded in his ears
and his hands bunched up in the trench coat and he shouted, voice crackled and
hoarse and he came, no buildup, just clenching and heat flooding everywhere and
his soso red dick pulsing drumbeat hard under Cas's fist. It kinda hurt now,
oversensitive like he hadn't been in the longest time and god fuck, he wondered
if he could just keep going like, forever; Cas wasn't stopping and he was still
hard and -
“Dean, jesus,” Sam's voice floated in beside him, glancing at him and the road,
back again. “How long did that take? Like thirty seconds?”
“Shut up,” Dean muttered, hunched more towards Cas. His body relentlessly
twitched towards the angel, everything still so tight even though he'd
unloaded. “If you'd just done it when I asked, y'know.”
“Oh yeah, we might have pulled a full minute out of you.”
“Or if I had something else to do,” Dean said, low, considering it, drawing
himself up on his knees and burying himself in Cas's neck, half-straddling his
lap and wrapping his arms all around him.
“Like what?” Cas asked, hand slowing in the new position but not much, grip
still tight. Sticky too, slick and warm with Dean's jizz. “You're much too
small to accommodate us in the usual ways.”
“No 'm not,” Dean muttered, mouthing Cas's neck, trailing up to his lips. “I
can take whatever you got.”
Sam laughed.
And fuck that.
Dean turned and glared at him. “I can.”
He hadn't been paying attention but noticed the area Sam steered them to when
he looked past his incredulous brother out the window. Deserted something or
other, shells of old brick buildings. It should have been creepy but instead,
Dean felt a thrilling rush on top of the aching need to come again and never
stop since his dick wasn't done. Obviously Sam had plans in mind, if he'd
driven them out here. Obviously.
“Just physically speaking?” Sam unbuckled, cracked his window the tiniest bit
and turned towards the crammed up pair in the passenger seat. “Cas said it,
you're too small. Even your mouth. Maybe even your hands.”
Oh, those sons of bitches, telling him what he couldn't do. A wave of prickly
anger swept over Dean, leaving him hot, flush-faced and annoyed.
“Move the seat back,” he glared at Sam again, jamming his hands down Cas's
pants at the same time. Nice that they fit between his belt and his skin all
small like this, wriggling easily towards the angel's pants-trapped dick, at
least until Cas grabbed his wrists and pulled him back out again. One handed,
his fingers circling both of Dean's wrists. Shit. Dean tried twisting out of
it, squirming, huffing, pouting in his defeat. “I can do everything I normally
can, you guys are being dicks.”
Dean tracked the silent conversation between his brother and the angel; always
alarming how in tandem they were when it came to him, specifically in these
situations. And they were unreadable and dark and hot as hell, slow to come to
some kind of conclusion, way too slow for Dean.
“I can prove it, okay?” he blurted out, wriggling again in Cas's hard grasp,
looking between the two of them, tamping down the momentary doubt fairly
easily, since he was still aching hard, leaking.
Sam raised his eyebrows first and Cas fixed a stare at Dean that almost made
him shrink down, made him want to disappear into a goopy, sticky mess for a
second.
“How?” Sam stated more than asked. But he moved the seat back anyway, the
jarring thump letting Dean get free.
He was on the floor immediately, knelt in the space between Cas's legs, still
staring up at him because that stare, that fucking monster hungry gaze didn't
let him look away. He didn't bother answering the question, nuzzling up Cas's
thigh, mouthing at his dick through his pants which, yeah, it was hard and he
bet Sam would be too. Dean flung his arm out towards Sam, surprised when it
barely reached. Advantages and disadvantages. His too-small fingers scrabbled
uselessly against his jeans, against his thick thigh. When he looked over, Sam
still had his eyebrows raised.
“Just c'mere,” Dean mumbled, “I c'n take both of you, c'mon.”
They both laughed.
Dean flushed scarlet and molten hot. Those assholes. He'd show them, he'd show
them both.
He undid Cas's pants fast as he could, ignoring the nervous little tremble to
his fingers, trying to choke off his gasp when that big dick soared out, right
in his face. All that talk and Cas looked fucking huge in front of him, thick
and daunting and he puffed out his anxiety, wrapped his hand around the shaft;
his fingers didn't even touch all the way.
“I can take it,” he said, half to himself, moving in slow, angling Cas's dick
towards his face, still reaching out for Sam.
He'd intended to sink down all the way on the angel's dick, like usual, swallow
him whole and prove his mouth was still viable but his lips stretched tight
around Cas's head and he had to force himself to keep sinking. Felt like inches
and inches, miles of dick choking his mouth and still so much in his hand. He
came up coughing and drooling, wiping his mouth with the back of his fist but
going right back for more.
Sam's hand in his hair stopped him, pulled him up so he caught the amusement on
his brother's face. “And you think you can take bothof us?”
“I can,” Dean said, stubborn, still stroking at Cas, his other hand pressed
into Sam's crotch, desperate for it even while he back-peddled his skills.
“Maybe just not in my mouth, y'know? But...but, Sam get it out, I'll show you.”
“So you can choke on it?” Sam asked, low and pressing Dean's hand harder
against him, whole big paw engulfing Dean's like it hadn't, well, ever, and he
felt his dick flex against his stomach. They were wasting time and he just
wanted to be under them or between them or whatever.
“Doesn't matter if I choke, does it?” Dean asked, did his best to blink pretty,
lick at his swollen up lips. “Gets the job done.”
Sam took a second but shrugged and that was it, he let Dean get his dick out
one handed, pushed him back towards Cas. Over-eager, moving too fast, Dean
choked again, forced himself to relax but okay, maybe it wasn't exactly
physically possible to deepthroat right now, maybe they were right. But he
wasn't about to give up.
Cas fisted a hand in Dean's hair and flexed the other around his neck, thumbing
at the swell of his throat and Dean wanted to, so bad, wanted to break in this
slim little throat with a great big dick but it just wouldn't go. He looked a
mess when he finally came up for air, watery eyes streaming down his cheeks,
mouth dripping drool and he only got one breath in before he was magnet-drawn
to Sam's dick, not so thick but bigger, way too much for this mouth. He did
choke on it, felt the blunt head ram against the back of his mouth but he kept
going, kept trying, worth the suffocation to feel Sam's breath hitch ragged,
for all the gasps and groans from the both of them.
Dean swapped back and forth like that for a while until his mouth felt raw,
until he'd gagged so many times he'd lost count and his fingers were actually
sore from grasping at what he wasn't trying to jam down his throat. He hadn't
touched his own dick in what felt like hours but he knew it was sticky and he
felt it throbbing, sometimes catching against the seat and his stomach. He
could totally get off like that but he wanted to make it last this time, wanted
to show Sam and Cas.
“See, I can do it, easy,” he gloated, hoarse, a dick in each hand, blinking
between them. “Can you just fuck me now? Please?”
“Who?” Cas asked.
“Doesn't matter, there's no way you can take either of us. None.”
Dean shouldhave known better, known he was being taunted and fucking called out
but he was all teen hormones and diamond hard dick and he was already reaching
for the glove compartment lube before he really thought about it.
“You're such a jerk,” he mumbled, too much to do now, scrambling up on the seat
so he straddled both laps, sliding his pants down, off, letting them pool on
the floor. “You're both jerks and you're both gonna fucking cry with how tight
I am, so just shut the fuck up, okay?”
“Aw, he's cranky,” Sam crooned at Cas, “Maybe it's naptime, maybe - “
“Maybe you should just fuck me, Sam,” Dean said, and his voice cracked at the
end, right when he grabbed Sam's huge hand in both of his, guiding it to his
ass. Sam squeezed right away, hard enough that Dean yelped and reached
automatically for his dick. He might have come in like, two strokes if Cas
hadn't pulled him away again.
“You need to last,” he warned Dean, low and slightly scary, no room for
argument in his eyes.
“He can't,” Sam said simply, murdering Dean's attempt at protests with his long
fingers gently dipping into the crease of his ass, finding his hole to rub at
it. “He came in fifteen seconds with your hand on his dick and he's gonna blow
in, like, ten once we start working him open. Surprised he didn't shoot again
while he was blowing us.”
“I do have some control,” Dean said, betrayed with gasps. He shoved the lube at
Sam, totally doubting himself now. It was easier not to spill while he had
something to focus on but now...now it was just him draped across Sam and Cas
and this goddamned hot pit of his stomach feeling at how tiny he felt, how
beyond control.
“You think so?” Sam teased him, “Cause, I think I could just slide one finger
inside and...sploosh. Wanna find out?”
“Fuck, fuck yes,” Dean panted, whined. Cas grabbed his dick again with a looser
grip than before. Not that it mattered, the eager thing jumped against his
thick fingers and Sam's even thicker fingers pressed slick against his ass, a
little cold but that was okay. He couldn't relax no matter how hard he tried,
his whole body taut and twitchy.
“I should go slow,” Sam started, tone warning, tip of his index finger
pressing, twisting until Dean gasped again, “Because I'm pretty sure this thing
hasn't been broken in yet, hmm?”
“I can...I can still...”
“Optimistic,” Cas hummed.
It was all Dean could do to breathe. Just one finger and he couldn't stop
clenching on it while Sam pushed in further. This body was on fire and crazy
and already he felt heat rising in his gut and he couldn't stop it, just whined
and leaned into Sam splitting him open and Cas's loose, slow strokes. Anything
tighter, anything faster and he'd come again and lose everything.
“Well, you're right, I think I am gonna cry if I even manage to get my dick in
there,” Sam said, more teasing, so much teasing and this time Dean had nothing
to say back. Just noises, getting higher and higher, ragged panting, a few
swears, nothing intelligible.
He slumped forward against one or both of them or the seat or something
muffling his unfaithful mouth with that stupid baby voice that kept cracking.
How did one finger feel so big? Granted, Sam had some of the biggest hands he'd
ever seen but just...how? This was gonna take forever. They talked, muttering
things Dean didn't care about hearing and then there was more nudging him open
and he made, easily, the most embarrassing noise once he realized that was
Cas's finger too, that they were both fucking him open, sharing his ass
equally. He was past it hurting, at least; still some burn at the stretch,
uncomfortably comfortable and really quite full already.
And his goddamned traitor of a dick flexed crazy, dripping so much he could
feel it and shit, shit, he was gonna come.
But Cas, Cas knew, spared him, choked it off with a vice grip around his base
that had Dean – he swore – coming without really coming, sobbing against the
seat, fingers clutching at whatever was close, Cas's coat and Sam's hair and
maybe they didn't notice, maybe -
“Nice catch, Cas,” he heard Sam mutter, impressed, though whether at him or the
angel, Dean didn't know. Didn't care.
“Can someone pleasejust actually fuck me? Please?” Voice so high and he didn't
care, he was desperate and he didn't care who it was, didn't care what fucked
up rules they set down, he just wanted on someone's lap or to get shoved up
against the back of the seat and rammed until he cried.
“Just one of us?” Sam teased him again, and that had to be his long finger
wriggling inside, nudging, twisting. “Thought you could take us both?”
“I can,” Dean howled, stubborn but warming to the fact that he would not be
able to have both of them in his ass at once, not like when he had the usual
frame.
“How?” Cas demanded and yeah, that was his finger, a bit thicker than Sam's,
tugging at Dean's tight rim, opening him up even more for Sam to quickly push
another finger in.
“How?” Dean repeated. Thinking, he had to think. “One...one in my ass, and one
in my mouth?” he blurted out fast, really without thinking but that'd work.
God, yeah, that'd work.
A second later, all the fingers left him, still clenching even empty, and he
was getting manhandled, easier than when he was full-grown and even then Sam
didn't have any problems. But right now, they rag-dolled him around, stripped
him and turned him onto all fours on the bench seat, his ass towards Sam and
his chest draped across Cas's lap. They fit perfect like that. He took a second
to look back at Sam looming over him, so big, so big and staring at his ass,
running a hand down his back. Dean shivered into the touch, arching like a cat,
fisting his little hand around Cas's dick which was mouth level, right there,
waiting.
“C'mon,” Dean urged his brother, pressing back until one hand curled around his
hip and tugged his ass up. He never fit like this before, not in the front seat
but they crammed together so snug, so perfectly perfect that Dean felt this
soaring moment of calm, this crazy zen while he stretched his mouth down around
Cas's dick and reached under himself for his own, throbbing more than ever.
Didn't last.
Sam warned him and he only half-heard but totally, unmistakably felt the thick
head of his brother's dick pressing against his tight hole, pressing and
pressing until it finally popped in and Dean fucking choked on angel dick, came
up coughing.
“Shit – fuck – Sam? - shit,” he sputtered, Cas's dick still on his lips and
tried to turn his head but Cas didn't let him, pushing him back down. He
couldn't really focus on anything, on any one feeling and all he was was
feeling. But quickly, the ache of Sam pushing in soared above all else and Dean
shuddered, came up for air again and twisted back to look. “I don't
think...god, Sam, I don't think I can.”
Sam stilled his hips, stroking up Dean's back with both hands, back down, not
even halfway inside Dean's ass but he looked the picture of control. “Just
relax, Dean, you can. Wanted it so bad. Still do, don't you?”
Dean nodded, already felt himself melting under Sam's strong fingers, and then
Cas's once they joined his brother's on his back, rubbing away the tension in
his bunched up muscles.
“You can take it, Dean,” Cas said, quiet, whispery low, fingers skittering up
into his hair again. “Would it help if you had something else to focus on?”
Dean nodded into the tension that held his head, blinking up sweetly at the
angel.
“Good. Just concentrate on my cock in your mouth.”
Dean sucked in a breath, nodded again and parted his lips around it, let his
eyes drift shut.
“The weight of it, and how your mouth stretches. How it tastes.”
“Yeah,” Sam joined, his big hands still rubbing up and down Dean's back.
“That's a good plan. Work on his dick, Dean. Mouth's all warmed up, maybe you
can take more of it, huh? Angle's better. You keep taking him, much as you can.
I'm gonna go real slow, okay?”
He couldn't nod this time, but hoped the grunt around the angel's dick and the
little swivel of his hips answered. And it was a good plan, he felt more
relaxed, more determined. Yeah, Cas's dick in his mouth provided the perfect
distraction and already, he got more in, inching ever closer to his grown-up
skill set. Sam's dick still pushed in but it felt easier, less daunting. He
could do this, he was doing this, cramming two dicks into his cursed little
body.
They talked over him; maybe Sam swore while his dick dragged in slow. Maybe Cas
asked how it felt but Dean's world narrowed down and it all flew right over his
head. If he lasted another ten seconds, that'd be a miracle.
But ten seconds, another ten, more and more time lost while he gagged on Cas's
dick, memorized how stretched his lips were, how it felt so he could always
remember it.
Then Sam's hand in his hair, Dean knew because he tugged sharper than Cas.
“Hear me? How's it feel? Everything you wanted? Better now?”
Dean tried to nod again, couldn't, settled on a choked out, “Yes, yes,” until
Sam let his head drop back. He went right for Cas's dick again, licking up the
shaft to give his sore mouth a break. He felt Sam bottom out in like, five
different ways, felt his balls squishing and his dick throbbing inside of him
and, most strange, felt this gentle bulge in his stomach pressing against his
hand where it was fisted around his own dick. God, that was special and he
couldn't talk to tell Sam, just moaned against Cas's dick and pressed back
against his brother.
Everything felt so full, so tight and stretched and burning hot and Sam started
really, actually fucking him, taking no time at all to let him adjust and it
didn't matter anyway because that would take hours. The tiny crack in the
window did nothing to cool their swampy fuck sauna and Dean was lost, so lost
between them but it was good, it was everything he'd ever wanted, familiar and
not, rough and reverent at the same time.
He outlasted Cas, somehow, but only by maybe half a minute; the angel was quiet
as always when he pumped up into Dean's mouth, nudging at his throat but still
couldn't make it down, so Dean felt him spill in the back of his mouth, moaned
and choked around it and Sam picked up his pace like a fucking jackhammer, like
he was hellbent on ruining Dean's brand new teen ass.
The usual filth rang in Dean's ears, Sam's, “Swallow all Cas's load, Dean, I
don't wanna see any spilling out of your dirty whore mouth or I'll fucking
smack it back down your throat with my dick,” and, “Gonna shoot so far up in
you, Dean, you're gonna choke on that too,” and, choppier, when his thrusts got
erratic, when his hands got bruising tight on Dean's slim hips, “Fucking work
that eager little dick, Dean, c'mon, it's time,” and just before Sam came, he
moved up over Dean, pressed him down against the seat so his dick pulsed
trapped and his face jammed up against Cas's legs and Sam just pounded pounded
while Dean kept coming and clenching.
Sam growled, pumped in animal hard and Dean felt the hot twitch inside of him,
easily recognizable but totally new somehow, thicker and harder than usual.
Dean felt so trapped, so nicely pinned down under him and surrounded by both of
them and this was just what he wanted, the whole time.
He didn't move for a while, just listened, felt Sam's breathing on top of him,
then soft squishy kissing noises above him and he wanted to see, wanted to join
in but he was wrecked and ruined and happy and sticky, still squeezing with his
heartbeat around Sam's seated dick.
So this was fine; if he never got to move again, if this was his life. He could
get used to it.
But then Sam hauled him up, but not off his dick, just in his lap, back to
chest, mouth to neck, his huge hands running over Dean's chest, over the mess
on his stomach and the protruding ridge of his dick.
“Pretty,” Cas rasped, his fingers joining Sam's until Dean lost himself between
them again. “How does it feel?”
“Full?” Dean blurted, his head lolling back onto Sam's shoulder, eyes sinking
closed. “Like...never felt so full.”
“Hmm,” Cas hummed, low, happy, his mouth against the other side of Dean's neck
suddenly.
No air anywhere, no reprieve for his twitchy teenage dick either; still hard
through the mess, jerking up against his stomach.
“Want a turn, Cas?”
Dean gasped at Sam's question, snapped his eyes open to watch the two of them
grinning at each other, mouths meeting on Dean's neck and by now, he knew there
was no way out of it.
Not that he wanted one anyway.
 
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