Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/1291099.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester
  Additional Tags:
      Underage_-_Freeform, Incest, First_Time, Bottom!Sam, Wincest_-_Freeform,
      Weecest
  Collections:
      Sunday_Morning_Porn_Club
  Stats:
      Published: 2014-03-09 Words: 2245
****** For The First Time ******
by iluvkinkythings
Summary
     Sam's been waiting for Dean to fuck him for months but now that it's
     about to happen, he's getting really nervous. Thankfully Dean is an
     awesome big brother.
Notes
     beta by alezig and cappy712 on livejournal
Tonight's is the night, Sam is sure of it. Dean didn't say anything but he
didn't have to; Sam knows his brother, knows that Dean is all about gestures
and small attentions and the evening has been full of it, some of them kind
ridiculously obvious - the long blowjob and the fingering in the car comes to
his mind - and some of them a little bit more subtle.
Dean probably isn't aware of it but he totally was blushing each time Sam
caught him looking at him at the diner and he also bit his lower lip quite a
lot whenever he thought that Sam wasn't paying attention. It's kind of silly,
really, how nervous Dean is about the whole thing.
If anything, Sam should be the one to be nervous. He's the one who's about to
take it up the ass for the first time tonight, after all, and Sam knows for a
fact that Dean actually has fucked at least two guys before so it's not really
like he doesn't know what to do. Besides, Sam's been fucking him for quite some
time now and it's not exactly like it's rocket science so yeah, Sam doesn't
know what exactly got Dean so worked up.
Maybe Dean's afraid to hurt him but that's stupid because Sam takes Dean's
fingers - and his owns as well - on a regular basis and yeah, Dean's a big guy
down there, definitely bigger than Sam, but he's not thatbig.
Maybe Dean doesn't like to top, though it seems impossible to Sam because...
well, just because. Sam sure loves his ass to be played with but he could never
stop to be on top because there’s not a better thing in the whole world than to
fuck his way into his big brother’s tight, round, perfect ass. So yeah,
switching is definitely the way to go and Sam figures Dean must feel the same.
That leaves one possibility: maybe the problem comes from Sam. It seems like no
matter what he eats, no matter how much he works out, Sam just can’t put any
meat on his bones and his ass is kinda flat and skinny and maybe Dean doesn’t
like it very much.
Okay, so now Sam’s the one to get all keyed up. He’s doing his best not to
tense because Dean’s resting his right hand on his thigh while he’s driving
them back to the little apartment they’re renting for this month but he’s
obviously doing a shitty job because Dean turns his head to look at him with a
small, worried frown.
“You okay, Sam?”
“Yeah,” Sam says but it doesn’t sound very convincing, even to his own ears. “I
just... I mean, you’re going to fuck me tonight?” he asks. Never let it be said
that Sam can’t be a blunt guy from time to time.
Dean shoots him a knowing smile and start to stroke his thigh in a soothing
way. “Don’t worry about it, Sammy. I’ll go real slow. And if it’s too much it’s
okay, we’ll try it again later.”
“But you want to, right? I mean, I know I kind of harassed you and you said
we’d do it once I turn fifteen but if you don’t really want to it’s okay I get
it, I mean I’m not as pretty as the girls you like to fuck and errr...” Sam
starts to laugh nervously. “I do say ‘I mean’ a lot, uh?”
Dean stays silent but Sam notices that the car is slowing down and Dean’s
parking it on the side of the road. “What are you doing?” Sam asks.
“Shut up, Sam,” Dean says as he’s removing his seat belt before plastering
himself against Sam and taking his mouth in a slow kiss. “You’re prettier than
anyone I’ve ever met, Sam. You’re perfect and I don’t give a fuck about others,
I want you and only you. I can’t wait to be back home, you know, so I can take
my time to open you up with my tongue. And then when you’ll be ready for me,
I’ll take you real deep and slow and I’ll make you feel so fucking good that
your fingers will never be enough again and you’ll always crave for my cock.”
Sam’s dick is so hard in his jeans that it hurts and he can’t stop a moan from
leaving his mouth. “Can we... Can we go now?”
Dean smirks as he adjusts himself and starts the car. Dean drives so fast that
they make it back to their place is less than five minutes.
~.~.~
Dean’s tongue and three of his thick fingers stretching Sam’s ass isn’t exactly
something new but now that Sam knows that they’re not the main course but more
of a hors d’oeuvre he fucks back against them with all he’s got, can’t wait to
finally have what he’s been asking for about a year now.
“Dean,” he whines, “I’m ready. Come on man, fuck me now!”
Dean laughs but it’s not mocking or teasing. “Such a bossy bottom, Sammy.”
“Takes one to know one,” Sam shoots back.
“Touché,” Dean relents. “You want to put the condom on me?”
Sam nods eagerly and hisses when Dean pulls his fingers out of him and turns
around to take Dean in his mouth while Dean grabs a condom from the bedside.
He slides down on his brother’s cock until the head in lodged deep in his
throat then stays there for a few seconds, knowing that it’s the most effective
way to get Dean rock-hard in no time flat. It doesn’t fail as Dean hardens and
thickens even more, and Sam sucks hard as he pulls back until Dean’s cock pulls
out of his mouth with a loud pop.
“Fuck Sammy, love your mouth on me,” Dean praises, his hands stroking Sam’s
face and hair.
“I know,” Sam says. He takes to condom from his brother’s hand, carefully
unwraps it from the foil and slowly unroll it down Dean’s thick shaft and Sam
is incredibly aroused by the sight of the thin veil of latex stretched to the
maximum. He blindly reaches under the pillows until he finds the half empty
bottle of lube next to Dean’s gun then squeezes a large dollop in his hand,
warms it up a little bit before coating Dean’s dick with it. He starts to
stroke Dean in earnest but Dean stops him with a pained smile.
“Easy, Sammy. I’m this close to blow my load already and I really want to be
inside you when I do.”
“Oh,” Sam eloquently says. “Can I ride you?”
“Not for your first time. Maybe later. You can get on your hands and knees or
on your side, I’ll fuck you from behind.”
“Oh, okay,” Sam says, not sure of how he wants it for his first time. He kinda
wants to try it doggy style but finally decides against it. They’ll do this
later when Sam will be used to taking his brother’s cock, so Dean can fuck him
hard and fast.
Sam lies on his side and shivers when he feels Dean sliding behind him, Dean’s
cock like a branding iron against his ass. It’s a familiar and comforting
feeling because that’s how they wake up every single morning. Dean slides an
arm around him, his big hand resting on Sam’s stomach, and Dean kisses him on
the neck.
“You ready, Sammy?”
“Yes,” Sam whispers, a little bit scared now but still really willing to get
through it. Dean’s hand slides down Sam’s leg to the crook on his knee and Dean
pulls it up against Sam’s chest, leaving his hole exposed. Dean lines up and
his cockhead is now pressing against his entrance and wow, Dean feels even
bigger than he looks and it takes everything Sam has not to tense up.
“Love you Sammy,” Dean says as he pushes inside and while it isn’t exactly what
Sam would call pleasant, the pain is not nearly as bad as he feared it would
be. Dean’s not entirely inside though and it get a bit worse as he feeds Sam
the last few inches because Dean’s cock is at its largest at the base and Sam
can’t help but whimper when Dean bottoms out.
“You okay?”
“You’re... big,” Sam pants and fuck but he’s starting to get soft and he really
doesn’t want Dean to notice. Dean always stays hard and Sam feels like he’s
failing his brother right now.
“And you’re tight,” Dean answers. “So fucking tight, Sammy. Fuck, it’s
amazing.”
Sam wishes he could say the same, and feel even worse when Dean’s hand finds
his almost limp cock. “Sorry,” he immediately says.
“It’s alright,” Dean says as he slowly strokes him. “It’ll get better in a few
minutes, you’ll see.”
And Dean’s right, Sam gets used to Dean’s cock in about five minutes, and
Dean’s kisses and his stroking have Sam hard again real quick after that. Dean
moves a little bit, first rolling his hips to test the waters, then starts to
thrust in and out when he realizes that Sam can handle it. And holy shit,
Dean’s fucking him and Sam’s been wanting this for so long and it feels so
fucking good that it takes Sam a few to get that the loud moans he’s hearing
are actually coming from him.
“Dean,” he says, totally aware of how awed he sounds.
“I know,” Dean says and Sam can hear how smug Dean feels. He doesn’t have the
strength or the want to call Dean on it though. “Feels good uh? Now you get why
I love it so much when I have your cock inside me. Though I have to say that
your ass feels even better, Sammy.”
Sam does get it, and fuck but when Dean shifts a little bit behind him and
angles his hips differently on the next thrust, it feels even better. Dean
found his prostate and makes sure to brush it each way in. When Dean picks up
the pace, fucking Sam with deep, long thrusts, Sam’s moans turn into cries and
he’s aware of how loud he is but he just can’t help it.
“The neighbors, Sammy,” Dean reminds him but he doesn’t stop to fuck Sam so Sam
doesn’t stop either. It seems to turn Dean on even more as he starts to fuck
Sam in earnest, and Sam gets even louder, which makes Dean wilder. “Such a
noisy bottom,” Dean grunts into his ear and without pulling out of him, Dean
manhandles Sam so he’s on his stomach, his cock trapped against the mattress,
and Dean’s on top of him.
Dean’s heavy and it’s a bit hard to breathe but Sam loves it, loves to have his
big brother’s larger body covering him, owning and claiming him like this.
“Dean!” Sam yells at one impressively well angled thrust and Dean all but press
Sam’s head down into the pillow. When Sam tries to scream, he gets a mouthful
of fabric so he bites around it, hanging on for the ride. Dean’s not rough but
he’s not as gentle as he started anymore and he’s grunting like a beast and
fuck but Sam knew it. He fucking knew that it would be this great and they lost
so fucking much time that he’ll have Dean to fuck him at least three times a
day to make up for it.
Sam’s cock doesn’t get much friction but the slide of the sheets against his
sensitive head proves to be enough to send him over the edge. He clenches hard
around Dean as he sprays the bed but his release and that gets Dean to come as
well.
“Oh fuck,” Dean groans as he bottoms out inside Sam and stop moving for a
while, a long throaty moan wrenched out of him and Sam wishes Dean wasn’t
wearing a condom because he’d like to feel Dean’s load inside him. Dean says he
hates the way it feels, the mess it leaves in his underwear when Sam’s come
leaks out of his hole, but Sam thinks he’d like it, the mere idea of it enough
to make his cock twitch and try to get hard again.
Dean pulls out a minute later and gets up to remove the condom and wipe himself
clean. Sam doesn’t move, trying to get his heart and his breathe to come back
to normal. He’s feeling a bit light-headed and he realizes that the pillow
almost made him pass out.
“So?” Dean asks as he comes back on the bed, pulling Sam against him. “Was it
like you thought it’d be?”
“It was better,” Sam says and he’s not even lying. “I’m a bit sore but I like
it. I want you to fuck me bare next time though.”
“You serious?” Dean asks, incredulous.
“You’ve always been careful with others right?”
“Yeah but-”
“It’d be like you’re marking me. And I’d always have you inside me, you know?”
“Fuck Sammy that’s hot,” Dean moans and he’s getting hard again against Sam’s
leg. Sam’s hard too and ready to go again.
“Do you think the neighbors heard us?” Sam asks.
“I don’t know. I hope they didn’t. Why?”
“Because I hope they did.”
“You kinky fucker,” Dean says laughing. “You just want me to make you bite your
pillow again.”
Sam thinks about it for a second. Maybe he does.
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