Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/227478.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      Incest, Sibling_Incest, Wincest_-_Freeform, Angst
  Stats:
      Published: 2011-07-23 Words: 2727
****** Five Times ******
by WhisperElmwood
Summary
     Five times Dean and Sam sought physical comfort with each other.
Notes
     The first and only time I tried out Wincest.
i.
The first time it happened, it came as a shock to the both of them.
Dean was just verging on nineteen, Sammy fifteen. Dad was away hunting and the
boys were in a paltry motel room. There was one bed to share, even if it was a
double, and there were two of everything. Dean insisted in the quiet of his own
mind, later on, that it was the bed sharing that did it.
The room wouldn’t have been half as bad if it hadn’t been half as cold. As it
was, the boys slept close together for warmth, the thin duvet wrapped tightly
around their bodies.
Dean dreamed. Hot and wet, writhing and moaning. He woke with his arms around
his brother, his face a breath away from Sammy’s. It took him far too long to
realise that he’d been dreaming, and even longer to realise that Sammy was
awake.
It took him no time at all to realise that they were both hard, their cocks
pressed firmly together.
Before he could say anything, Sammy moved closer and pressed their lips
together in an awkward, childish kiss. A small hand moved over his hip and the
cock pressed against his own rubbed urgently.
He gasped, “Sammy, I...”
But Sammy shook his head and simply kissed him again. Damn them both, but his
body responded before his brain could work out what was going on. His hand
slipped down, between them. Holding Sammy closely, his right arm looped around
his brother’s shoulders as his left hand pulled them both free and wrapped
tightly around their cocks.
Sammy arched into the touch, keening gently, almost silently and Dean knew he
was the first to touch his brother this way. He knew he was the first and the
knowledge bled guilt heavily into his chest, even as he began to slide his hand
over their aching erections.
“D-Dean!” Sammy’s lips parted on a gasp, his eyes wide and Dean couldn’t take
it anymore. He leaned forward again and began to kiss his brother. As he jerked
them off, he slowly coaxed those lips further apart with his tongue and set
about teaching him how to kiss.
It didn’t take long. It was almost frenzied. The hand on his hip gripped
tighter and tighter, Sammy’s torso contorted; his breath stilled and his lips
stopped. He came with a wordless cry of pleasure, come shooting over Dean’s
hand and both their stomachs.
Dean pressed his forehead to Sammy’s shoulder and kept his hand moving. The
going was slicker now and Sammy’s breath ghosting over his ear. The little
pants and gasps as he regained his breath, made it all the hotter, though he
hated himself for it.
One small hand rested against his head and the other moved from his hip.
“Dean?”
He ignored Sammy until that hand wrapped around his own and suddenly they were
both jerking at his cock. He looked up again, eyes locking to Sammy’s and they
stared at one another. Dean groaned, the sound of mixed pleasure and pain as
the orgasm tore through his body.
Sammy never looked away. He watched Dean as he came and continued as he slowly
calmed down again. He pulled his hand away and smiled. “Thanks, Dean.” 
A discarded t-shirt cleaned them up and soon Dean was lying in the silence,
watching his brother sleeping and feeling as if the guilt would eat him alive.
---
ii.
The second time, they were less shocked and a little older.
Sam and Dad were arguing a lot. This time though, seemed worse than all the
other times. Dean had the feeling Sammy had made a decision and the knowledge
of it was fuelling him.
After a pause, Dean allowed his eyes to travel back to his brother.
Sammy wasn’t small anymore. He was eighteen and going on at least six and a
quarter feet by now, and Dean was sure he’d not stopped growing yet. With that
thought came a low wash of guilt and the remembered feeling of small hands. He
swigged his beer to wash the memories away.
Picking out a fresh can, he padded to his brother and handed it over. They
didn’t say anything, simply sat in silence; Dean tried to drink away his unease
and his fear, his upset. Sam appeared to drink away whatever it was that was
fuelling him these days.
Dean is still hazy on how it happened, but he thinks it started with a whisper.
“Dean...”
And Sammy was straddling him, crushing their mouths together in a harsh,
fierce, angry kiss. They were drunk; he knew it, Sam knew it, but apparently
only drunk enough to get them here, not to hamper the proceedings. He could
feel his brother’s cock pressing hard against his own.
Dean ignored the new and quickly rising levels of guilt and let his hands
scrabble at Sam’s fly, as Sam’s long fingers worked at his. Far too quickly,
Sam’s jeans and boxers were around his ankles and Dean’s pushed down his thighs
and they writhed, rutting almost, against each other.
Sam used his weight to push Dean into the sofa, forcing him to stay and Dean
let him. He gripped Sam’s hips in shaking hands and let his little brother do
whatever he wanted. When Sam’s large, square hand wrapped around both their
cocks, he whimpered into the bruising kiss.
Sam’s lips left Dean’s and a moment later, he felt teeth at his shoulder. Dean
threw his head back, bucking his hips up as Sam’s teeth bit deeply into his
flesh. They both knew it would bruise, like a brand. Dean thought maybe Sammy
got off on that.
“S-Sammy!” Dean’s hands gripped tighter as he forced himself not to move, but
Sam ignored him in favour of kissing and biting his way around Dean’s neck and
shoulders; always low enough that he could hide the bruising later.
When they came together, Dean at a growled word from Sammy, they continued to
move against one another slowly, both panting and gasping. Until Dean whispered
into the silence; “You’re leaving, aren’t you?”
Sam then stood quickly, pulling his jeans and boxers back up, tucking himself
away without a word. A moment later he was gone and Dean sat alone, feeling
dirty and worse than he had before Sam straddled him.
---
iii.
The third time was a plea for help and Dean gave it willingly.
Jess had been dead less than a week and Sammy was slowly splintering around the
edges. Dean could see it, even though his brother tried to hide it. He was
never good at emotions, worse at talking about them, but he could tell Sammy
was broken, in need of something he could probably never give him.
When Sam slid into bed with him in a dingy motel, Dean said nothing. He simply
opened his arms and pressed a chaste kiss to his brother’s forehead.
It was Sam who spoke, whispering into Dean’s neck. “Please... please,” repeated
softly, as large hands caressed Dean’s body. He couldn’t say no, couldn’t say
anything at all really. So he simply let Sam take the lead, again.
He coaxed Sam to full hardness, before doing the same for himself. As Sam
removed their underwear, he pressed his lips to Dean’s body, murmuring
incoherently; words Dean was sure were not meant for him. Once they were naked,
he pushed long fingers into Dean’s mouth. It was then Dean realised Sam needed
this, his brother needed to feel something different. He only hoped he could
provide.
Sam slicked himself, prepared himself, rolled onto his side pulling Dean in
close behind him. Dean didn’t ask if he was sure, he knew he was. He slicked
himself and wrapped his arms around his brother’s body, pressing in.
They moved together, slow and steady, letting the physical sensations grow and
grow, sweat soaked bodies sliding and thrusting. The silence was punctuated
only by soft grunts, thready gasps and the wet sounds of hips and groin meeting
backside. Dean didn’t want this to feel good, didn’t want to enjoy what he was
doing. But he did, and the familiar guilt pooled in his stomach alongside the
building orgasm.
He came first, arms clenching as if for dear life around Sam’s chest, hips
pressed firm to his brother’s ass, pushing himself as deep inside as he could
reach, spilling into him pulse after pulse of bitter-sweet pleasure, his hips
jerking with each. Dean resisted the urge to press a kiss to the back of Sam’s
neck and concentrated on regaining his composure.
When he could move again, he snaked a hand round and wrapped it around Sam’s
still hard cock. Sam was breathing deeply, harshly, making the soft keening
sounds Dean remembered from the first time. It made his stomach clench to hear
it. He said nothing, kept jerking his brother’s cock, until Sam came with a
broken cry.
Still buried inside him, hand still wet from his orgasm, Dean held Sammy as he
finally broke down and wept. He held him in silence all that night, even after
he’d cried himself to sleep.
---
iv.
The fourth time it was goodbye.
They had tried everything; every avenue, every witch-doctor and hoodoo-priest,
every loophole or legal blunder. But they had found nothing and so Dean was
going to die. Probably horribly.
He planned to go down hunting, though. He planned to go down hurting Lilith,
killing her if he could, dragging her screaming and kicking down with him, if
at all possible. Out with a bang. Live hard, die pretty.
His due-date was a week from now. The planned Lilith-hunt set for the same
date. Tonight was his; Theirs. Their last night of relative freedom, no matter
how much Sammy had fought or hoped, planned or schemed. He planned to watch
sports, drink too much and maybe wank himself to sleep. A normal evening with
his brother, doing nothing but relaxing. An evening to savour.
Sensing what was going on, Sammy changed the plans somewhat. When Dean sat down
and handed over a beer with a grin, Sam put it almost immediately down.
“Sammy?”
Dean watched as his brother shook his head, a sad gleam to his eyes. He watched
as Sam stood and took Dean’s can, placing it on the table beside his own. He
watched as, completely sober, Sammy straddled his lap and kissed him softly.
“I don’t want to say it...”
It was only later that Dean realised he meant “Goodbye”.
They went slow, taking their time, memorising each other. They were naked and
had bruised lips by the time Sam pushed Dean back onto one of the beds. This
time there was real lube at hand. Sam straddled him again, sinking down onto
Dean’s cock with a sigh. His eyes never left Dean’s, their gazes locked.
Sam rode him slowly, drawing it out and out and out. Dean’s toes curled with
pleasure-pain and he pushed himself up to sitting, wrapping his arms around his
brother’s torso, holding him tightly as they moved together. Sam’s hands cupped
his head, smoothed through his hair and caressed his neck and shoulders. He
buried his face in Sam’s neck, panting gently.
Dean may have cried a little, but if he did, the tears were lost in the sweat
coating their bodies and never mentioned.
Sam came first, streaking their stomachs and chests with come as he cried out,
his voice once more broken and painful. He kept moving, holding Dean tightly,
rocking and grinding until Dean tensed beneath him, gripping him bruisingly
hard as he thrust up into him, pulsing come deep inside him with each upward
motion.
They stayed that way for a long time, holding each other in silence. They moved
only when Dean was sure his emotions were held in check and he could safely
look into his brother’s eyes without breaking.
---
v.
The fifth time it was cathartic and the last time.
A year. A year Dean had thought Sammy gone, lost to him, trapped in Hell. No-
one, not even Bobby had seen fit to tell him. And Sammy was different. Dean
didn’t know why, couldn’t put his finger on it, but it was there, hanging
between them.
A year spent off and on with Lisa. A year wishing he had it all back again. A
year mourning his brother for dead, or if not dead, then alive and in Hell.
He’d been there, he remembered it so well. He still woke up with the screams
ringing through his mind. But this past year, his brother’s voice had been
added, his brother’s body and soul writhing in pain. Under his knife.
Seeing him again, alive and well, even if he was changed, it was... he could
barely take it.
After that first hunt together, after meeting his relatives, after everything,
after the Djinn, even after he offered the Impala and Sam refused, Dean
couldn’t stay. Not anymore.
They were on the road again. Together. Something Dean had thought would never
happen ever again. And when Sam approached him one night, out of the blue, no
possible catalyst in sight, Dean didn’t turn him away. Couldn’t turn him away.
He didn’t understand this thing they had between them. Never had and never
would. He just accepted it for what it was, accepted it and let Sam do what he
wanted. This time, they were in another motel in the middle of nowhere. Dean
had argued with their grandfather, again and he was simply enjoying a beer and
the peace.
The first he knew of Sam’s presence was a touch to his shoulder, atop the scar
Castiel had given him, fingertips brushing against flesh he didn’t let anyone
else touch. He shivered and looked up and Sam caught his lips in a kiss. They
hadn’t kissed often, but he felt the difference. But his brother moved over
him, pushed him down flat along the sofa and he stopped thinking, just ran with
it.
“Dean...”
Sam almost tore Dean’s clothing from his body and before he knew it, they were
both naked and pressed together, his brother’s frame almost too large for the
sofa they were crammed into. He wasn’t sure he minded, though, when Sam’s lips
found his throat and a slicked hand wrapped around his cock.
But, it was almost perfunctory. Before Dean could even begin to enjoy what Sam
was doing to him, Sam slid down his cock, impaling himself in an almost too
swift, too smooth and practiced a move. Dean’s hands found Sam’s hips and he
gripped tightly. Sam only smirked down at him and began to move, one large hand
splayed over Dean’s chest, the other wrapped around his own cock.
Dean shut his brain off and went with the physical, went with the fact that
this was Sam, Sammy, his brother. His brother whom he’d thought lost to him. He
gripped Sam’s hips tight, locked his eyes on Sam’s face, focused his attention
on Sam’s weight on his hips, the powerful grip around his cock and let himself
learn that Sam was here, he was back and they were together again.
Sam came with a deep groan and a curling of his torso that looked almost
painful, spilling himself over Dean’s chest and stomach. The sight brought Dean
ever closer and he looked into Sam’s eyes when he sat back up again, still
rocking and shifting. There was nothing in his eyes. There was pleasure, of
course, but nothing else. He had the feeling Sam was still moving over him
because it was the polite thing to do.
Before he could say anything, Sam leaned down and began to kiss him. Lips and
then teeth trailed over his jaw-line, down his throat, over his shoulders. A
hand wrapped over the scar on his shoulder and gripped tight. The build up of
sensations pushed Dean over the edge and he arched, gripping Sam tightly,
thrusting into him as he came.
When he was done, Sam kissed him one more time and pulled away. Within moments,
Sam was dressed and leaving, an empty “thanks, Dean,” his only words before the
door closed behind him.
Dean pulled himself up and slowly, methodically cleaned himself off and
dressed. He finally allowed himself to think.
Sammy hadn’t only changed, he’d changed drastically. And Dean was terrified.
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