Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4119610.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester, Dean_Winchester_&_Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester, John_Winchester
  Additional Tags:
      Wincest_-_Freeform, First_Time, Anal_Sex, Sex, Explicit_Sexual_Content,
      Top_Dean, Bottom_Sam, Top_Dean_Winchester, Bottom_Sam_Winchester,
      Masturbation, Mutual_Masturbation, Teenchesters, Weecest, Teenagers, Teen
      Dean, Teen_Sam, Teen_Dean_Winchester, Teen_Sam_Winchester, Plot_What
      Plot/Porn_Without_Plot, Porn, Porn_With_Plot, Porn_with_Feelings, Smut,
      Fluff_and_Smut, Inspired_by_GIFs, contains_nsfw_gif
  Series:
      Part 13 of Wincest_Drabbles_&_Ficlets_insprired_by_pics/gifs, Part 7 of
      Wincest_(teen_years), Part 11 of Wincest_Firsts
  Stats:
      Published: 2015-06-11 Words: 7314
****** Dean, Interrupted ******
by Destiel_Cockles
Summary
     When Sam catches Dean in the act Sam admits he has never successfully
     jerked off so being the awesome big brother he is, Dean decides to
     teach him a thing or two.
It’s after midnight when John finally pulls up to the house he has rented dirt
cheap for next three weeks. Not only do Sam and Dean have actual bedrooms but
for the first time ever they have their own rooms. They have been dealing with
several vengeful spirits and it has been hell tracking down what is anchoring
them here. John had gotten Dean up at five a.m., they got their weapons
together and left by six-thirty. It was a long hellish day and all Dean wants
to do is go to bed, unless of course Sam is still up. Most of the time he waits
up, worrying until Dean and their father get back.
Dean opens the door and as he’s getting out John hands him the key to the room.
He doesn’t have to tell Dean what he was doing, he does the same thing every
night. He doesn’t need to tell Dean his responsibilities either but always
gives Dean orders every time he leaves.
“Goin’ to the Roadhouse. Make sure all the salt lines are still intact, make
sure your brother is asleep and watch out for him. You know the rules. No
sneaking out…or sneaking girls into your room. Got it?”
Dean nods and John clears his throat. Dean lets out a deep breath and mutters,
“Yessir.”
John shoots him a warning look but surprisingly doesn’t tell him to lose the
attitude. Dean is also surprised that he barely gave him any orders. Normally
he would tell Dean what to do or not do while he was gone and it always took
him at least ten minutes. He must be desperate to get drunk…or get something
else but Dean didn’t want to think about that. His dad only stressed the ‘not
sneaking out or sneaking girls into his room’ because last week he had caught
Dean sneaking out a few times so Dean started sneaking girls into his room and
thought his dad had no idea until he woke him up that morning at five and told
him he would be hunting all day since he had enough energy to mess around all
night every night with a different girl. Having a room to himself for the first
time ever Dean had gone a little wild but John reamed his ass so he figured he
would just either wait until his dad got back and passed out for the night or
jerk off, most likely the later because Dean was tired as hell, especially
after being tossed around by a group of vengeful spirits.
John takes off and Dean unlocks the door, quietly opening it then closing it.
Sam is on the couch, the TV is on and he’s asleep. Dean takes his jacket off
and tosses it on a chair then carefully slides his arms under Sam’s neck and
knees then slowly lifts him up. Most nights Sam passes out while he waits for
them to get home. Dean had called about an hour earlier telling Sam they would
be home soon to just go to bed but Sam never went to bed until Dean made it
home and he knew everything was okay. He had done this since Dean went on his
first hunt and Sam had to stay at Bobby’s, he waited up until three in the
morning when Dean got back. It got worse several months earlier when Dean had
gotten caught stealing food and was sent to Sonny’s for a month. He hated that
John told him he got lost on a hunt the entire time he was gone because ever
since then Sam had nightmares about losing his brother.
As soon as Dean starts walking, Sam moves around. Dean shifts him so his head
is lying on his shoulder and continues down the hall to his brother’s room. He
can feel Sam breathing against his neck and when Sam shifts Dean can feel his
lips brush against him, sending a rush of heat through his entire body. Sam’s
arm moves up and wraps tightly around Dean’s neck when Dean stops in front of
his bed.
“Dean,” Sam mutters sleepily, slowly opening his eyes. “You’re okay.”
Dean pushes the covers down and gently sets Sam on the bed. “Of course I am.
Nothin’ bad is ever gonna happen to us, Sammy.”
Dean thinks about how much he wishes that were true and how much he hates the
fact that his brother will someday see the evil things he has seen as he gently
runs his fingers through Sam’s hair until his eyes flutter shut. The room is
dark except for the moonlight seeping through the curtains and Dean can barely
see him but he still watches him for a few seconds. Dean pulls the covers up
and quietly whispers his brother’s name. When Sam doesn’t answer and Dean can
hear his light even breaths he bends over and kisses Sam’s forehead then softly
whispers, “I’ll always be here for you, Sammy.”
As Dean turns to go, Sam whispers, “Promise?”
Dean isn’t sure if Sam heard what he said or was responding to what he said to
him before he fell asleep. He turns around and looks at him, Dean wants to
climb in bed with his brother even if they never get to the point he wishes
they could be at, he just wants to hold him in his arms because he never wants
Sam to know how bad things can be, he never wants him to hunt and see the
things he has seen since he was eight years old. He wants to protect him, make
him forget about every worry until he falls asleep lying against him.
“You know I do. You okay?”
Sam bites his lip and nods. His eyes slowly droop closed but he tries to keep
them open. Dean walks back over to his brother and slowly cards his fingers
through his longish brown hair.
“Get some sleep, Sammy. Dad’s goin’ somewhere tomorrow…it’ll just be us and we
can do whatever you want, ‘k?”
“Really?”
“Yeah…just go to sleep. If he comes home and you’re still up he’s gonna get
pissed.”
Sam is already falling asleep so Dean walks out of the room. He stands in the
doorway, making sure Sam falls asleep with no problem. Watching his brother
always makes Dean horny, and as soon as he is sure Sam is asleep he goes to his
room and shuts the door. There’s no way in hell he can sleep now, when he had
carried Sam to his room just feeling the warmth of his body and holding Sam had
him hard.
Dean pulls his shirt off and tosses it on the floor. He plops down on the bed
and reaches under his pillow for the magazine he put there earlier. He quickly
flips through the worn down pages to the girl he’s jerked off to more than any
of the other busty beauties.
As he stares at the hazel eyed girl with brown hair, pouty lips and tits bigger
than any in the hundred or so issues he’s seen Dean can feel his cock
thickening, straining against his jeans. The next page has her spread out but
Dean doesn’t really care about it, in fact most of the time he isn’t thinking
of this girl, or any girl for that matter but he’s trained his body to get
turned on by the naked women because the one thing he wants to really think
about he knows he can’t have, but each and every time Dean is jerking off he
can only think about his brother, even during sex Dean is comparing the girls
to him then picturing himself deep inside of Sam rather than anyone else
because there is no one else that turns Dean on, he can’t stop fantasizing
about his brother.
Dean unbuttons his jeans and moans softly as he unzips them, finally freeing
his erection that has been throbbing for hours while he thought about his
brother the entire day, especially on the ride home. When he was talking to Sam
on the phone he had gotten so hard the only thing he could think about besides
fucking Sam was getting to his room and jerking off. He shoves the jeans and
his boxers down and kicks them off onto the floor. He shifts to get more
comfortable and wraps his hand around his cock, groaning as he finally gets the
stimulation he has been dying for.
The magazine falls to his side then onto the floor as Dean gets into it right
away. He’s waited much too long to mess around with anything, he has enough
images in the spank bank to go without porn, especially because he’s with the
object of his deepest fantasies 24/7. Just the thought of Sam makes Dean’s cock
twitch hard. He runs his thumb over the head, spreading the precome oozing out
down his shaft.
Dean starts thrusting his hips up, imagining he is in the tight heat of his
brother’s ass. Dean feels pleasure coursing through his body as he pictures Sam
riding his cock. Dean’s eyes slam shut and his mouth falls open as a wave of
pleasure overtakes him. He grunts and bites down on his lip, panting and
moaning as he feels a fire deep in his stomach burning. He’s so close, on the
brink of orgasm when he hears it. His door opens slowly and he knows that Sam
probably had another nightmare, he should have locked his door but he was in
too big of a hurry to get off and wasn’t thinking clearly.
Sam flips the light on and whispers, “Dean?”
“Fuck,” Dean mutters under his breath, he needs release so damn bad but isn’t
about to in front of Sam. Not yet. He shifts around and struggles to pull the
covers he’s been lying on over his still very erect cock. There is a blatantly
obvious bulge, even when Dean nonchalantly puts his leg up. Sam is standing at
the edge of the bed, Dean thought he was asleep in his own bed but lately Sam
has been having more and more nightmares and usually ends up sleeping in Dean’s
room.
“What were you doing?”
Dean chuckles, Sam is thirteen and the exact opposite of him at that age. When
he was thirteen Dean started the partying, getting drunk and having constant
sex that he still does to this day. He knew all about sex since he started
grade school. Although Sam didn’t bang girls all the time and most likely had
never even been with a girl, Dean was sure he jerked off…he had to, there was
no way in hell he didn’t know what masturbating was. Hell, at thirteen Dean
jerked off so much he really did almost go blind.
“C’mon, you know what I was doing.”
Sam’s eyebrows knit together as he chews his lip. His expression is blank but
Dean can see his eyes flicker down to where the thin sheet is tented up,
strained from his huge erect dick. Dean can’t stop himself from slowly stroking
his cock, he had been seconds away from coming and now that Sam is right there
only a few feet away when Dean was just picturing the kid riding him, he is
astronomically horny.
“Are you fucking with me? What do you think I was doing naked, jerking my fist
up my cock?”
Sam blushes a deep red, his eyes suddenly huge as they focus on the movement of
Dean’s hand. Dean wants to stop but can’t especially now that Sam’s eyes are on
him because it is making him so damn horny he is about to explode, he’s
surprised he isn’t coming. Dean wonders why Sam seems so surprised he is doing
it, he knows damn well Dean does it because when they are stuck at motels Dean
does it in the same room and even though he is asleep he has to know it’s the
reason Dean takes so long in the shower every morning.
“Don’t act like you don’t do the same damn thing.”
When Sam looks up at Dean he can see it in his eyes that he doesn’t and Dean is
shocked, he honestly thought Sam did, didn’t all teenage boys do it? Sam was
almost fourteen and he has to have constant boners like Dean does, he can’t
imagine ignoring them all the time.
“You seriously never jerked off? Not even once?”
Sam bites down hard on his lip and looks at the ground as he just barely shakes
his head and whispers, “Not really.”
“Why not? There’s nothin’ wrong with doing it…it’s like, bad if you keep
holding back.”
Sam’s eyes water as he peeks up at his brother. His voice quivers as he asks,
“R-really?”
“Yeah, you should uh, get release when you get a boner…You have had one before,
haven’t you?”
Dean knows damn well he has because half the time that is what causes Dean to
have one. A quick glance to Sam’s pajama pants tells him he’s right. He wonders
if maybe Sam has trouble getting off but is too embarrassed to say anything. He
can’t just let his brother suffer though masturbating or getting blue balls
whenever he gets hard. Dean can only think of one way to help Sam but he knows
it is a terrible idea but he’s Sam’s big brother which means he has to help him
with things no matter what.
“Um…all you gotta do is…I mean, you know how right?”
Sam shrugs and looks at the ground. Dean stops moving his hand up and down his
cock because as always no matter what, Sam comes beforeeverything, even Dean
getting off when he is so close—on the brink of insanity close—because it’s Sam
and that’s what Dean does, it’s his job to look out for his brother and show
him things…even if it happens to be things like this because Dean would do
anything for his brother no matter what.
“I mean, you’ve gotta know a little about it. You’re so fucking smart you get
all A’s in school and…”
Dean trails off, he knows it’s no time to joke around because Sam is obviously
embarrassed. Dean doesn’t really understand why but knows that’s just how his
brother is.
Sam sniffs and mutters, “I know how…I guess…it just…”
Dean waits for Sam to finish and tries to guess what his problem is…he can only
really think of one thing. “You do use like…lotion or something…right?”
Sam’s eyebrows scrunch together and out of the corner of his eye Dean notices
Sam’s hand rub the front of his pants , so he obviously knows the mechanics of
it just not everything and he obviously also is turned on by something…and Dean
can’t help but think that he wasn’t turned on until he knew what Dean was
doing. There’s no way Sam doesn’t know about it so either he just is…dry or
wants Dean and this is his way of trying to get Dean to make a move.
Dean isn’t stupid, he knows his brother worships him, he sees Sam checking him
out and blush when Dean notices but Dean beat himself up mentally for months
for even thinking about them being together once Sam started doing it, telling
himself no matter what he couldn’t have Sam no matter how bad he wanted him but
now all he can think is if Sam admits he wants it or makes a move, he’s not
going to stop him. Dean prays he does but knows Sam is way too shy to ever hit
on him or say anything about it.
Sam’s face is flushed a deep red as he stutters, “I-I…no…it hurts when…I
can’t…”
Dean closes his eyes and takes a deep breath. He can’t miss the pain in his
brother’s eyes or the lust. Knowing he is never going to be able to go back
once they open this door, and also that he will never be able to stop himself
once it happens. Dean decides to say fuck it and let whatever happens happen.
He shifts over and pats the bed.
“C’mon, get in.”
Sam sits down on the edge of the bed and peeks up at Dean through his bangs.
“You’re really gonna help me?”
Dean mouth suddenly goes dry as reality sets in, this is finally happening. He
nods and Sam smiles. Dean slides his tongue across his lips and bites down on
them. “Um, as long as you’re sure…and um, if you decide you don’t want
to…you’ll tell me.”
“I want to…” Sam is still stiffly sitting on the bed, even shyer than he
normally is when it comes to things like this and Dean knows for sure he does
want it because if Sam doesn’t want to do something he complains until Dean
knows what he wants and with Dean he is rarely shy unless it comes to sex. Sam
glances down at the ground and adds, “I’d never change my mind.”
Dean wants to just pounce on his brother, if he was hard and horny before that
was nothing compared to how horny he is now, and his dick is so hard he can
barely stand it but there is no way in hell he is going to do anything until he
is sure Sam is ready. He wonders if he should have Sam turn the light off,
maybe if he can’t see his brother he will be less tempted but knows that just
the thought of them lying next to each other doing what they are about to be
doing will make it even more difficult to control himself, then there will be
any noises and shit, maybe he should just back out. He still has time, he could
just give Sam some lube and Kleenex and send him back to his room but Dean knew
this day would come and it was pointless to continue avoiding the feelings he
knew they both had for each other.
Dean notices that Sam is wearing his hoodie he had worn the day before, he
hadn’t realized it before. Sam never said he had a bad dream and Dean knows Sam
never wears sweatshirts to bed because he gets hot easily…he wonders if Sam was
wearing the hoodie while he thought about him and tried jerking off but
couldn’t get off. Dean feels his achingly hard cock start throbbing at the
thought.
Sam looks over at Dean, waiting for instructions. Dean clears his throat and
takes a deep breath. “You should um,” Dean pauses, he never gets nervous but
suddenly his heart is racing and his voice is shaky.
He tries to remember that maybe Sam is only here because he needs help with
this, he has to quit thinking that maybe his fantasy is finally coming true—he
has to put Sam first then if he wants more Dean will happily give him anything
he wants.
Dean takes another deep breath then continues, “Get comfortable, you’re
supposed to enjoy it. Quit acting like you’re in detention or something.”
“Y-you’re really gonna show m-me?” Sam asks skeptically.
Dean would be more than happy to do a hell of a lot more than just show him how
to jerk off but he should probably take things slower since Sam is obviously
nervous and if he hasn’t even successfully jerked off it’s safe to say he has
also not had any kind of sexual contact, probably never even kissed anyone.
“Uh yeah…just um…get under the covers and I’ll tell you what to do.” Dean bites
on his lip then quietly adds, ”Whatever happens after that…guess it’s up to
you.”
Dean hopes Sam will make a move once he’s relaxed and horny because Dean has
always sworn to himself he would never touch Sam until Sam either made a move
or begged him to. He had to at least be comfortable enough to ask because he
figures if he cannot even say it then he isn’t ready.
Sam chews on his lip, eyeing the narrow bed. He pushes the covers down enough
to climb under them and settles in then glances at Dean for direction.
“So um…you kinda gotta…you know…it’s easier if you’re um,” Dean sucks in a
breath, not sure why he is suddenly so nervous. He has never in his life been
shy about anything related to sex but then again he has never attempted
something with someone he is actually not only attracted to but in love with.
“Um…naked...”
Sam’s blush deepens and creeps all the way down his chest as he looks up at his
brother. “Everything?”
Sam has always been self-conscious about his body, unlike Dean, and since Sam
gets embarrassed just taking his shirt off in front of anyone Dean adds,  “Do
whatever you’re comfortable with…you can leave it all on but it’s easier to um,
have room…it’s up to you if you want to take anything off.”
Sam slowly nods and takes a deep breath. Dean can feel him shift as he pushes
his hips up then slides his pajama pants down and to Dean’s surprise he takes
them completely off. When Sam’s hips come back down his thigh brushes up
against Dean’s and he can feel his brother’s muscle flex in response to their
proximity. Dean can’t take it anymore he starts stoking his cock again, just
the thought of them jerking off together turns him on a hell of a lot more than
it should.
Dean tosses the bottle of lube he was using at Sam and he picks it up. When he
reads what it is his eyes widen as he glances up at him. “Isn’t this…for like,
um…s-sex?”
Dean nods then grins. Sam knows a hell of a lot more than he lets on. Dean knew
he did because Dean is always talking about sex.
“Yeah but you can use it for jerking off and…other things.” Dean decides not to
get into fingering yet since Sam hasn’t even experienced an orgasm. “So you um,
you know…use some lube. You can use lotion or um, spit too. Put some on your
hand and let it get warm.”
“Dean I-I don’t think I can…”
“Sure you can, just grip it and move your hand. You’ll get into it and…”
“I mean…” Sam blushes again and looks down at the bottle of lube. “…can’t you
do it for me?”
Dean’s hand freezes and he sucks in a breath. The thought that this actually
happening creeps into his mind again and every drop of blood rushes to his cock
because Sam wants him to do it for him but Dean quickly counters that Sam
didn’t exactly say he wanted to do things, but figures he would never ask Dean
to jerk him off unless he wanted this to go somewhere. He realizes Sam is
waiting for an answer, nervously biting at his lips, obviously praying Dean
says yes.
Dean nods and picks up the lube, his hand visibly shaking as he pours some out
and rubs his fingers through it to warm it up. Sam peeks back at him then
quickly looks away.
“If…if you don’t want to…”
“I do,” Dean answers a little too eagerly. He bites down on his lip and takes a
deep breath, his cock is so damn hard from just the thought of this, he’s never
come untouched but today might be a first for him too. Dean realizes Sam is on
his left and is about to shift to his side but it would be easier if Sam was on
his right. “Um, we gotta switch sides though because I gotta use my right
hand.”
Sam nods and sits up then kneels. As he begins to put his knee over Dean he
freezes when he realizes there is nowhere for him to go. Dean catches on and is
about to shift when Sam nudges his legs apart and sits down in front of Dean
between his splayed open legs, deciding he would be less nervous without having
to look at his gorgeous brother as he gives him a hand job, otherwise it would
most likely be over before it even starts.
“Is this okay?”
“Yeah,” Dean chokes out, trying to figure out if he should sit up and wrap his
arm around his brother or have him lay back. He is sitting too far away so Dean
puts an arm around Sam and pulls him closer. Sam thinks Dean wants him to lie
down so he leans back against Dean. Dean sucks in a breath as Sam backs his ass
completely up against him, trapping his erection between them. He can feel his
balls and the base of his cock pressing against Sam’s ass and it is so fucking
tempting to just thrust against him but then remembers this is about showing
Sam how to jerk off, not about getting himself off but feeling the heat of
Sam’s body against him makes it so damn hard to focus.
Dean figures since it’s going to be Sam’s first orgasm he’s going to not just
give him a quick handjob, he’s going give him the best orgasm he can. Dean
slowly runs his non-lubed hand up Sam’s inner thigh, caressing the soft
sensitive skin then ghosts his fingers up and down. Sam moans softly and Dean
can feel him slowly relax. Sam shifts and his sweatshirt rides up enough to
cause Sam’s soft skin to rub up against Dean’s cock, his hips involuntarily
thrust and he lets out a soft moan.
Dean tries to focus but his cock is pulsing, desperate for more stimulation and
feeling Sam against him is like being teased, slowly driving him crazy. He
focuses instead on the fact that he is actually touching Sam and savors the
feeling of finally being so close to him. Dean runs his hand slowly up the
sweatshirt Sam still has on then gently slides his fingers across Sam’s chest,
caressing the soft skin, digging his fingers lightly into the developing
muscles. He slowly teases his finger across his nipples and Sam sucks in a
breath.
“Sometimes if you take it slow…it um, makes it even better,” Dean says in a low
voice as his fingers gradually start rolling Sam’s nipples. He runs his other
hand up Sam’s thigh, getting a gasp then Sam grinds against Dean and he can’t
stop the moan from flying out of his mouth. Sam seems to like teasing his ass
across Dean’s cock and it is driving him insane. Dean holds his breath and
bites down on his lip when Sam slowly moves up and down, from the base of his
cock until he pushes himself up all the way and brushes against the head.
“Shit, Sammy,” Dean whispers, unable to stop himself from lightly thrusting
against Sam as he repeats the motion. Dean wraps his arms around Sam and softly
kisses his neck, running his hands up and down Sam’s abdomen and chest,
trailing them down his legs then back up. Sam stretches his neck out as Dean
works his way up and down. He sucks down where Sam’s neck meets his shoulder
and Sam stops moving and groans.
“Dean,” Sam’s breathing quickens even more then he starts pushing against Dean
harder. Sam loves feeling Dean’s big thick cock pressed tightly against him and
judging from the noises he is trying not to make Dean is enjoying this just as
much as he is, maybe even more.
Sam pushes his hips up when Dean’s fingers trace over his hipbones, avoiding
his dick. Sam whimpers and presses tight against Dean, feeling him squirm and
suck in a breath. Dean’s fingers move down Sam’s erection, tracing down to his
balls.
“Dean, please…”
Dean rolls Sam’s balls in his hand lightly, Sam’s breathing quickens and he
turns his head, resting it against Dean’s shoulder so he is now completely
pressed against him. Dean has to fight another urge to roll his hips, the
burning of Sam’s skin against him has instantly made him ten times hornier.
Sam gasps as Dean’s fingers slowly tease across the head of his cock down to
the base. Dean makes a tight fist. He doesn’t grip him as tight as he normally
would himself, not sure if it would be too much. He has never done anything
with another guy and even though Dean has done nearly everything else sexually
with girls this is all new to him so he just goes with what he likes figuring
Sam will like it too.
“Dean,” Sam moans softly as Dean starts to slowly pump his fist up and down,
twisting it and brushing his fingers across the head on the upstroke. Sam
shifts and Dean bites down on his lip when it causes Sam to press against his
throbbing erection even tighter.
Sam turns his head to look at his brother, causing their lips to brush against
each other. Sam tentatively presses his lips against Dean’s. Dean turns his
head for a better angle and kisses Sam gently several times then slides his
tongue across his brother’s lips until Sam finally opens his mouth. Sam moans
as Dean’s tongue slowly glides around his mouth exploring every inch as he
continues pumping his fist up and down Sam’s cock, gradually moving faster and
tightening his grip.
Dean is kissing Sam with so much passion and pent up lust Sam feels light
headed. He starts moving his hips into Dean’s fist which causes him to press
down hard on Dean’s cock. Dean speeds up, kissing Sam harder, Sam pushes back
against Dean and grinds against his brother’s hardness causing Dean’s mouth to
fall open in silent ecstasy. He jerks the sweatshirt up and Sam sits up enough
to rip it over his head and throws it on the floor. When Sam lies back against
his brother and feels his skin burn against him Sam groans and starts circling
his hips as he feels his brother’s cock twitching and sweating out precome
against his back. Sam sucks down on his brother’s plump lower lip, sinking his
teeth in when Dean’s grip tightens and he starts jerking his fist up and down
his dick faster.
“Dean! Oh god…”
Sam arches his back as pleasure rocks through his entire body. When he settles
back down his ass lands against Dean’s cock hard and it is now pressed firmly
between his ass cheeks. Dean groans when he feels Sam’s muscles tighten around
his cock.
“Fuck,” Dean groans as Sam starts slowly squeezing his muscles together and
moving up and down faster when he realizes how much it is getting to his
brother. “Sammy…”
Dean puts a hand on Sam’s hips and thrusts against him, cursing under his
breath as he imagines how incredible being inside of his brother would feel.
Sam wraps his hand around Dean’s and pulls it off of his cock.
“You wanna stop?”
“No! I-I want to feel you inside of me, De. Please.”
“Sammy, you’re too-”
“Don’t you dare say I’m too young, I’m almost fourteen and I know you had sex
before you were fourteen.”
Sam tightens around Dean’s cock, grinding against Dean harder. When he hears
Dean curse under his breath and start grunting he moves faster. Dean puts a
hand firmly on his hip to stop him before he comes.
“Sammy, I just don’t think that…”
Sam jerks Dean’s face to his, crushing their lips together and turns so he is
lying over his brother. Dean slowly feels himself giving in as his brother’s
inexperienced tongue explores the inside of his mouth then intertwines with his
tongue. Dean takes over the kiss, quickly turning it up as he fumbles for the
lube and pours more onto his fingers as he continues to kiss his brother
heatedly.
Dean slowly teases a finger across Sam’s rim, tracing over the tight muscle
until he is able to ease his middle finger in. He inches it in as Sam shifts
then starts thrusting so their erections are pressed tightly together. Dean
slowly works his finger in, when Sam starts moaning and pushing back for more
Dean works another finger in.
Dean brushes his fingers across Sam’s prostate, getting a loud groan out of
him. He gently massages his fingers against the bundle of nerves as he thrusts
against Sam, rubbing his hardness roughly against his brother’s erection.
“Feel good Sammy?”
Sam nods hard, putting his hands on Dean’s chest as he pushes himself back then
bites down on his lip and starts panting and moaning as Dean scissors his
fingers. “Oh God, Dean…so fucking good.”
Dean kisses Sam then pulls back and leans his forehead against his brother’s.
He looks into his eyes then asks, “You sure you wanna do this?”
“I’ve never wanted anything more than this. You’ll…do it again, right?”
“If you like it we can do it as much as you want.”
“Really? I’m going to love it.”
Dean rolls them around so Sam is underneath him and kisses him as he puts more
lube on his fingers and slides them back in Sam. He wants to make sure he is
stretched as far as he can get him but Sam is too horny to wait, impatiently
pushing down on Dean’s fingers.
“C’mon De, I’m ready.”
“I’m not exactly small.”
“I know and I wanna feel your big thick cock in me before dad gets home.”
Dean suddenly realizes it has been well over an hour and that his brother is
right. He starts teasing the head of his cock against his brother’s rim,
watching him carefully to see if he is hurting him. Sam bites down on his lip
and sucks in a breath as Dean starts easing in and he immediately pulls out.
“You okay?”
“Yes, fuck. Please stop asking me that and just fuck me already. You do this
with girls too?”
“Fuck no.” When Sam looks up at Dean he kisses him and grins. “You’re the first
person I’ve fucked that I actually care about and…”
Dean trails off, not wanting to sound girly but Sam knew what he meant. He
smiles and wants to ask Dean if he loves him but decides it might piss him off
and shuts his mouth.
“I can take it…just do it.”
Dean meets resistance and thrusts in harder, wincing at how unbelievably tight
his brother’s ass is. It feels incredible as soon as he circles his hips and it
is getting more difficult to hold back. Dean slowly thrusts in a little more,
pushing past the tight ring of muscle that was holding him back. He eases back
then thrusts all the way in and pauses, relishing the incredible tight heat of
Sam’s inner walls hugging his cock tight.
“Oh fuck,” Dean mutters, rolling his hips as he groans. “Shit…so damn tight…”
Sam glances at his brother, he is biting his lips and his eyes are squeezed
shut, he lets out a long breath then opens them, his eyes meeting Sam’s.
“Too tight?”
Dean slides his tongue across his lips and grins then leans forward and kisses
Sam, cradling his face in his hand as his thumb caresses his face.
“Fuck no…it’s goddamn perfect…fucking incredible. You okay?”
Sam nods as Dean traces his finger down his jaw and tilts his head up and
kisses him softly on the lips. He gradually starts kissing him harder as he
begins to rock his hips, thrusting in and out a little faster each time. Sam
grabs a fistful of Dean’s hair and leans his forehead against his brother’s.
His mouth falls open and he moans as Dean slowly pulls out then hits his
prostate with a hard powerful thrust. His fingers tighten in Dean’s hair and he
starts making hot pleased noises that go right through Dean, straight to his
cock. He wants to make Sam feel pleasure unlike he as ever felt and wants to
have him moaning and screaming with pleasure.
“Feel good?” Dean asks as his hand slides down Sam’s chest and starts tweaking
his nipples.
“So good…fucking incredible.”
“Shit, you think this feels good?” Dean thrusts into Sam a few more times then
eases out. Sam opens his mouth to protest but Dean catches his lips in a kiss
then mutters against them, “Get on your knees and I’ll fuck you into the
mattress.”
Sam doesn’t need to be told twice, he jumps up and nudges Dean until he moves
out of the way. Dean licks his lips and grins. “Damn.”
“What?”
“I love that you’re already a slut for my cock.”
Sam blushes and wraps his fist around his brother’s dick. He hadn’t gotten a
good look at it earlier, he knew it felt big as hell, it’s so long and thick he
slides his hand up and down, gradually picking up speed. Dean bites down on his
lip and moans. He makes a tight fist around Sam’s cock and they both start
trying to jerk the other off harder.
“Fuck Sammy…thought you didn’t know how to do this…shit!”
Sam opens his mouth to answer just as Dean’s fingers tease across the head of
his cock and instead lets out a loud moan.
Dean stops moving his hand and pulls Sam’s off of him. He leans closer to his
brother and kisses him. “That was fucking good…your hand was about to be
covered in jizz.”
“Really?”
Dean nods and kisses Sam again, pulling him onto his lap and he wraps his arms
around him and kisses him with so much intensity Sam feels like he is sucking
all of the air out of his lungs he pulls back and Dean grins.
“Fuck yeah…you worry about things too much, you over think everything…you just
do it and it feels fucking incredible.”
Sam climbs off of Dean’s lap and kneels on the bed. He glances over his
shoulder at Dean and responds, “Then show me how fucking incredible fucking me
into the mattress is.”
“Shit,” Dean moves so he is lined up with his brother and puts his hands on his
hips. “You sure you can handle my big fat cock pounding into you?”
Sam nods. “No holding back…promise?”
Dean bites his lip and grins then kisses up Sam’s spine. He starts sucking down
on his neck as he teases his cock just barely inside of his brother. “Only if
you promise not to hold back…I wanna hear how much you love feeling your big
brother’s cock buried deep in your tight little ass.”
Dean slowly thrusts into Sam, sucking in a breath when he feels how much deeper
he can get. “Fuck Sammy…goddamn you feel fucking incredible.”
Sam pushes back against Dean to get him to start thrusting hard but he is
relishing the feeling of being balls deep. Dean slowly starts thrusting into
Sam faster, rocking his hips as he sucks down harder on Sam’s neck. Sam is
gasping and moaning, the sharp drag of his brother’s cock against his inner
walls is indescribably perfect.
Dean wraps his arms around Sam, he makes a tight fist around his cock and
starts jerking it up and down in rhythm with his thrusts as his other hand
caresses his abdomen and chest. Dean starts tweaking his nipples and Sam starts
swearing and groaning, grinding into him and pushing back harder meeting every
thrust until they are in perfect rhythm. Dean is slamming into his prostate and
the feeling is pure ecstasy. Dean shifts and suddenly Sam feels a burst of
white hot pleasure.
“Dean!” Sam shouts between moans, “Oh my fucking God it’s so fucking good. Love
feeling your big fat cock in me.”
Dean loves hearing his brother come apart, he knows it has to be feeling
incredible to get Sam to be so vocal. Dean jerks Sam’s head over and kisses him
heatedly then pulls back and kneels up. He puts his hands on Sam’s hips and
starts pulling him into every thrust.
“Son of a fucking bitch, you’re getting so goddamn tight…shit, Sammy…hittin’
your sweet spot just right, huh?”
“Fuck Dean, yes. Holy shit…”
Sam’s voice cuts out and he starts shuddering, Dean feels him spasm around him
then clench down so hard it takes his breath away.
“Fuck!” Dean shouts, his teeth tearing into his lips.
Dean starts pummeling into Sam as hard as he can, he reaches down between Sam’s
legs and starts pumping his fist up and down, tightening his grip when Sam
starts moaning incoherently. Sam starts coming, his entire body shaking, his
vision goes white and he suddenly feels completely boneless. Dean feels Sam
start sinking down so he digs his fingers into his hips and starts thrusting
into him harder.
“Dean! Shit!” Sam yells his brother’s name as he climaxes hard, ecstasy washing
over him as his orgasm rocks through his frame.
Dean’s thrusts become more frantic and Sam can tell he is close. He clenches
down on him then feels Dean’s hot come shoot spurt after spurt deep inside of
him. He hears Dean grunting and groaning between pants. Dean mutters a string
of curses as he thrusts into Sam and rides out his orgasm. He leans down and
kisses his brother then carefully pulls out and collapses on the bed next to
Sam.
They both struggle to breathe as they lie in post orgasmic bliss. Sam closes
his eyes, his entire body is pulsing from the pleasure. He feels Dean wrap his
muscular arm around him and pull him over his chest. Sam lays his head on
Dean’s shoulder and wraps his arm around his brother’s abdomen. Dean leans down
and kisses Sam’s forehead. Sam leans up and kisses his full plump lips and they
start kissing with more intensity. Dean turns the kiss up until Sam is pulling
back breathless.
“Bet you would’ve jerked off a long time ago if you knew it felt that good,
huh?”
Dean smirks as Sam rolls his eyes. “I’m sure jerking off is nothing compared to
getting fucked by you…now that I know how good it is I don’t think I could ever
settle for anything other than your big thick cock giving me an orgasm.”
Dean can hardly believe this is the same kid who couldn’t even say the work sex
without blushing and stuttering an hour earlier. He slides his tongue across
his lips and grins. “Next time you’re horny…you can ride me.”
Sam sits up and straddles Dean’s hips. Dean raises an eyebrow. “Already?”
“Why, you don’t want to?”
“Fuck yeah…so I guess since dad’s gonna be gone a couple weeks I’m gonna have
to teach you all kinds of sex positions.”
“You mean…there’s more?”
Dean chuckles. “Shit, there are entire books full of positions.”
“You gotta teach me everything. I wanna do it all with you. You gotta teach me
how to do blowjobs, rimming, everything you know.”
Dean can already feel himself getting hard. He can’t wait to do everything with
his brother. “So were you playing dumb earlier?”
Sam bites his lip and blushes. “Maybe a little…I’ve never um, had an orgasm
before now.”
“Well shit, we got a lot of catching up to do. How ‘bout after you ride me we
take a shower together then after dad leaves tomorrow I’ll show you everything
you wanna know.”
“Dean? What is rimming anyway?”
Dean grins as he puts his hand on Sam’s hips and pulls him forward. “I’ll show
you.”
 
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