Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/572455.
  Rating:
      Explicit
  Archive Warning:
      Choose_Not_To_Use_Archive_Warnings, Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Additional Tags:
      robo!sam, Underage!Dean, Prostitution, The_90s, Time_Travel, Alternate
      Universe, Robo!Sam_is_a_scary_fucker, Dean_was_a_twink, Dean_still_is,
      Why_does_Cas_do_the_things_he_does?, Wincest_-_Freeform, Plot_What_Plot/
      Porn_Without_Plot, Top!Sam, Oh_Dean, Prostitute_Dean, Underage_-_Freeform
  Stats:
      Published: 2012-11-24 Words: 3727
****** That One Time in Delaware ******
by antarshakes
Summary
     Cas hides Robo!Sam in the 90's, where he meets the younger version of
     Dean, sixteen years old and hooking to be able to survive the next
     day.
Notes
     written for the blindfold_spn kink meme, where anon asked for:
     RoboSam goes time travelling for some reason and ends up back in the
     ‘90s. Either intentionally or accidentally, he finds a younger Dean
     (no younger than 16 please) selling himself on the street to get
     money for he and ‘90s Sam’s survival. RoboSam figures ‘why not’ and
     takes Dean back to a motel room to fuck him.
     p.s.
     Even though this was looked over by the amazing Maichan, I tinkered
     around with it A LOT, so all remaining mistakes are mine (and feel
     free to point them out to me! I appreciate that shit)
See the end of the work for more notes
*-*-*
With one tap against his noggin, Sam is dropped unceremoniously into a random
bathroom stall in a random mall in the middle of Bumfuck, Nowhere.
He kicks open the stall door, scaring the one guy into pissing on his own shoes
as he gives Sam a frightened look.
Sam first notes the man’s tracksuit and a Walkman hanging off his belt, before
he pins the guy with another look. “Hey guy, where the hell am I?”
The guy stutters out a “Dover,” and hurriedly zips up his pants.
“Dover, Delaware?” Sam asks. The guy nods, wipes his hands off on his pants and
speed walks out of the bathroom. Sam calmly saunters out after him, listening
to the guy's swish-swish, suspecting he’s in the 90s, in fucking Delaware.
He makes his way through the throng of people to the nearest exit, looking left
and right, before opting for right.
Sam, of course, remembers Dover. They spent some time here. Might have even
been a few months. Cas has apparently dropped him off in the 90's, with no
explanation whatsoever. And if it weren’t for the inconvenience of not having
his gear at hand, Sam wouldn’t give two shits about getting the fuck out of
here.
He stalks his way to the outskirts of town, where the people aren’t so much in
a hurry, judging from the folks leaning against lampposts and lurking in
doorways. Sam thinks he might remember this neighborhood and when he spots a
familiar old motel, he’s sure: this is where they were staying.
Sam’s about to make his way over, when he spots a kid stumbling out of a car in
front of the entrance. The kid smirks while he straightens his jacket and wipes
a hand across his mouth. When he turns his head, Sam gets a good look at his
face. A grin involuntarily breaks out over his own features. That’s his brother
right there. Dean can’t be older than sixteen and his younger self can’t be too
far away. The memories come flooding back now. They were stashed in that seedy
motel for two months while their Dad was supposed to do a two-week job. Just
him and Dean stinking up the room like crazy. Sam remembers spending hours in
their room, reading books that Dean would bring in and take away as soon as he
was done with them.
Sam looks on, bemused, and lets out a “huh,” when Dean doesn’t immediately
return to the motel, but instead crosses the street and chooses a spot near
some mailboxes across from a convenience store. Sam looks on as Dean cocks one
hip and keeps his hand resting lightly on his pocket, no doubt keeping his
earnings safe. It doesn’t take long for someone to step up to Dean, exchange a
few words, and lead him into a dark alleyway.
Sam, out of boredom or curiosity, whatever you want to call it, crosses the
street and follows the path Dean had taken. He makes sure to stay in the
shadows as he watches how Dean drops to his knees and takes a random cock in
his mouth, going to town like there’s no tomorrow. The guy he’s blowing is a
middle-aged man, pudgy, and Sam finds it miraculous that Dean was even able to
find his cock. The guy keeps blabbing about how Dean’s a “good little bitch,
ain’t ya?”. It’s frankly pathetic to watch how he loses it in less than five
minutes. Dean spits out the man’s come onto the ground, stands up again, and
tucks the guy in. The john tries to catch his breath, while digging around for
some bills. He stuffs them in Dean’s pocket and slaps Dean’s ass as he walks
away. With one last grin thrown over his shoulder, Dean makes his way out of
the alley.
Sam remembers Dean being gone for hours on end, but he’d be home every evening,
making sure Sam would get to bed on time. Sam also remembers waking up in the
middle of night to see Dean’s bed empty, or hear the shower running, or the
sounds of retching coming from the bathroom. Well, Sam thinks, guess this is
what old Dean-o was doing. He should’ve known that Dad didn’t think to leave
them more money than the two weeks he was supposed to be gone required. If only
John Winchester knew what his son was really up to.
Sam makes his way to their motel, remembers the floor they were on, and
requests the same. He figures he might as well stick around something he knows.
Sam and the old them are the only ones on that floor. 
That same night Sam hears arguing and recognizes his own childish voice,
telling Dean that he’s, ‘not Dad’ and why does he leave Sam alone all the
time. Why doesn’t Dean want to spend time with him?
Dean’s weary voice cuts through, telling younger Sam that he needs space to
himself from time to time and doesn’t like being cooped up, especially since he
doesn’t have the patience to finish books like Sam does.
By then Sam has stepped out of his motel room, leaning against the wall near
his door. He can make out their words perfectly from here. Not too long after
the voices have died down, does Dean himself step outside, closing the door
behind him softly. As if he senses Sam, he looks up sharply.
Sam used to think Dean was bigger than life back then. Nothing could hurt his
loudmouth brother and Dean was king of the world. All Sam wanted to do back
then was wipe that fucking permanent smirk off of Dean’s face, make a dent in
his bravado. Looking at his sixteen-year-old brother now, Sam sees no traces of
that. He sees a scared, clueless kid and instead of feeling remorse about
treating his brother like that back then, he wants to explore this kid further.
Sam licks his lips and Dean seems frozen on the spot. He recovers quickly
though, glancing back towards the door as if silently willing younger Sam to
lock the bolt. He looks back towards Sam and Sam can tell that he slipped his
game-face on in that split second.
“Can I help you?” he asks in a voice that’s a few octaves lower than his usual.
When Sam just raises an eyebrow, Dean walks past him towards the elevator.
From the elevator, Dean cuts him another puzzled look. Sam wonders if Dean
recognizes him and sees the vestiges of pudgy little Sam in his face. He stares
Dean down, until Dean turns away with a high blush on his cheeks, shoulders
visibly tense.  Sam enjoys toying with Dean like this… as much as he can enjoy
anything, that is.

“Hey, kid,” he calls out.
When Dean looks back, he jerks his head towards his own door. That seems to be
the last straw for Dean and he stalks over. “Look man, I don’t know what you
take me for but–” Before he can get the rest of the sentence out, Sam grabs
Dean in a move that he knows Dean hasn’t learned to block yet and has him right
against the wall. 
“You’re selling,” Sam breathes into Dean’s shocked face, “I’m buying.”
Dean struggles momentarily, but seems to give up when he can’t get out of it.
He chances another glance at his own room door and back to Sam. “Fine. But no
kinky shit.”
With that, Sam releases him and pushes Dean inside his room.
“What’s the going rate, kid?”
“Fifty for a blowjob, a hundred for fucking. I don’t spend the night and I’m
not calling you Daddy,” Dean delivers with a smirk.
Sam has to laugh at that, because the humor in this situation is not lost on
him. Dean has a small smile playing on his lips when Sam stops laughing.
“You sure we haven’t met, man? You look awful familiar.”
Sam smirks at that. “Nah, kiddo. I’m sure you would’ve remembered me.”
Dean stares at him for a few beats longer and gives a small nod. “So what’s it
gonna be?”
Sam takes his time settling on the bed. “What’s the rush?” he asks. “How about,
you take your clothes off first, and then let me decide how to use you before I
pay you double’s worth, hm?”
Dean sucks in a breath and nods, keeping an eye on Sam as he undresses. The
first thing he takes off is the pendant Sam gave him all those years ago, the
same way Sam has seen him do ever since he got that little trinket. Dean stuffs
it in his pocket, before he removes his jacket followed by his shirt. Dean’s
body is pale and freckled, he’s still soft and boyish with a hint of a six pack
trying to show. He’s going to get bulkier in ten/fifteen years, but for now,
he’s still a twink with features just this side of feminine and way too pretty
for a boy his age. Dean starts on his boots next, then socks, pants, and
finally his briefs. His body is smooth, not a hair in sight.
“What’s your name kid?” Sam asks, wanting to know what alias Dean would use for
his Pretty Woman persona.
“Dean,” he answers after a few beats, and then, “yours?”
Sam contemplates lying, but for some reason he wants to mess with Dean’s mind.
 “Sam.”
Dean looks him up and down in appraisal. “You look like a Sam.”
“You look like Julia Roberts, now undress me.”
Dean visibly bristles at that, but like the true, little prostitute he is, he
doesn’t say anything about it. He saunters over to where Sam’s sitting on the
bed and straddles Sam’s lap. The weight of him on Sam is nothing, just a small,
skinny thing adding some pressure. If he wanted to, he could fling him across
the room with no effort at all. He should find this funny, because as much as
Dean loves to use his looks, he has desperately tried to get away from them
too. He knows Dean started to eat more and exercise more rigorously when Sam
started to outbulk him. If only he could see the stark difference between his
twinky self and what Sam has grown in to.
Dean’s still-soft hands start unbuttoning Sam’s shirt from bottom to top,
nothing like the coarseness Dean has now, fingers crooked and calloused from
years in the life.
 Dean wiggles on Sam’s lap as he slides the shirt off Sam’s shoulders,
caressing his hands over Sam’s muscles. Sam feels himself start to harden from
the stimulation, but it’s nowhere close to getting where he’s planning on
going. Once his shirt is fully vested, Sam lifts Dean off his lap and drops him
unceremoniously on the bed. That all-too-familiar indignant look comes back to
Dean’s face, but he doesn’t say a word.
“Take my cock out,” Sam orders, “and get me hard.”
Dean complies immediately and starts unbuttoning Sam’s pants, lowering Sam’s
underwear just enough so he can get Sam’s dick free. Dean’s eyes widen at the
sight, no doubt wondering how he’s going to take it, but again, he remains
quiet. He starts by jacking Sam slowly, putting his mouth on Sam’s half-hard
dick, until he’s so stiff Dean can’t swallow his entire length.
“You can take it all, can’t you Dean-o?” Dean’s head perks up slightly at his
childhood nickname, but he just nods, relaxing his throat to let Sam all the
way in. His tongue works slowly up and down the ridges and the vein. Sam
wonders how many cocks Dean has had in his mouth to be able to take him like
this. He shoves forward a little bit to see if he can get a reaction out of
Dean. Dean chokes a little bit, but he doesn’t let anything on, just keeps
bobbing his head up and down, jacking Sam faster.
If Dean thinks this is all there’s going to be, he has another thing coming.
Sam forcefully lifts Dean’s mouth from his cock, making a string of saliva
stick to Dean’s puffed up lips. He rubs his dick over Dean’s lips for good
measure and then pushes him backwards.
“Ass up in the air, kid.”  When Dean just looks at him, Sam rolls his eyes. “I
got condoms, boy scout. Don’t worry about it.”
Dean licks his lips and turns over, head leaning on his hands as he raises his
ass up as high as it can go. His balls hang heavy between his legs and Sam idly
admires that his brother is such a good cockslut. Noticing his smooth hole, Sam
rubs the pad of his thumb over it, easily slipping it inside.
“Still so loose, boy scout,” Sam notes absently. “How many cocks did you take
today?”
“Enough to take you,” he hears Dean mutter.
“Oh really?” Sam asks. “Enough to take a fist as well?” Dean’s asshole clenches
hard at that, prompting Sam to laugh and bend over to lick at his rim. When he
pushes his whole thumb inside, Dean just shudders. He reaches out his other
hand, seeking out Dean’s mouth with three fingers.

“Get ‘em good and wet, Dean. It’s all you’re going to get.” At that, Dean
starts sucking on Sam’s fingers with more vigor. Keeping his right hand in
Dean’s mouth, he licks around Dean’s hole, fucking his left thumb in and out.
No matter what, dry fucking is fun for no one. On the moan around his fingers,
Sam pulls out and slowly stuffs the three wet digits into Dean’s glistening
hole, one by one. There’s still some resistance, but Dean’s pushing back, and
Sam doesn’t really care either way.
“Fuck yourself loose on them,” Sam orders. His jeans are still mid-thigh on
him, but not really restricting him, so he doesn’t bother taking them all the
way off. He roots around in his pocket for a stray condom and rips the packet
open with his teeth. Sam pulls his fingers out just as Dean seems to be getting
really into it. Dean watches him with dark eyes from beneath his lashes,
watching and making sure the condom is on right and is secured. Sam just gives
him a bemused look back as he tugs at the tip of the condom, spits on his hand,
lubes up his cock and sits down on the edge of the bed. With another look
thrown over at Dean behind him, he gestures at his dick: “Ride it, kid.”
Dean’s arms are shaking when he moves off the bed and plants his knees on both
sides of Sam’s hips, slowly lowering himself onto Sam. The head of Sam’s dick
breaches Dean’s hole easily, but it’s the girth that Dean seems to have trouble
with taking. So Sam wraps a steadying arm around Dean’s narrow waist and
shallowly fucks in and out of him before thrusting all the way in with a grunt.
Dean matches him with a loud groan, muttering “shit, shit, shit,” as Sam orders
him to move. On trembling legs, Dean lifts himself up and on the downward
stroke, Sam thrusts upwards, making Dean cry out.
“Christ, Dean-o. Makes me think you’ve never had a real cock up there.”
Sam takes a good look at Dean’s face: sweat beading on his brow, eyes shut
tight, lips gnawed puffy, and body fully flush. Sam stills his movements,
causing Dean to open his eyes and hold Sam’s gaze.
Then Dean lurches forward and catches Sam’s mouth using those same lips Sam has
seen on countless of chicks. Too startled to protest, Sam lets him play with
his tongue for a bit, before resuming his thrusting. Dean groans around his
tongue as he starts pushing back, trying to bounce up and down, but unable to
settle on a rhythm.
The push and pull gets tiresome pretty quick and Sam pulls out, manhandling him
onto the bed again.
“I think you’re worth more ass up, kid.”

He slaps Dean’s ass to get him scrambling quickly into position. When Sam
enters him again, he just drops his head on the bed, fisting the sheets. Sam
takes a moment to look at the way he has Dean lithe body speared on his cock;
his flushed red cock stands out starkly against the pale skin of Dean’s ass
cheeks, asshole spread obscenely wide. Sam shoves forward a bit to see Dean’s
hole widen further. He does that a couple of times, pulling out just to see
Dean’s hole taking him over and over again, opening up so easily for him.
A groan from Dean pulls Sam from his reverie and with a snap of his hips,
begins to fuck Dean in earnest. He knows Dean is loving it when on every stroke
of his prostate, Dean bites into the cheap sheets. The slapping of skin on
skin, balls on balls, resonates in the room along with Sam’s heavy breathing
and Dean’s muffled, hoarse moans. It doesn’t take long before Dean is clamping
down hard on Sam’s cock and spurting helplessly onto the sheets, his cock
untouched.
Sam drags his hand through the mess on Dean’s stomach and pulls his cock out to
cover it with come, before he pushes back in. The glide is ridiculously smooth,
and with every thrust Dean’s hole gets more and more wet. He starts ruthlessly
fucking into Dean, while Dean tries his best to fuck back. When Sam reaches for
Dean’s spent cock, squeezing it, Dean lets out a high keen, clamping down hard
on Sam. As he feels his balls draw up, he pulls out, ripping the condom off,
and flipping Dean over on his back with the other.
“Open up, Dean-o,” he orders and Dean obligingly opens his mouth. Just a few
pulls and Sam is spurting onto Dean’s neck, mouth and cheeks.
Dean licks up everything he can reach and lies there spent, chest heaving
quickly. Wringing the last drops out his cock, Sam stands up and locks gazes
with Dean. His moistened eyelashes are clumped together, and the green of his
eyes have never been more vibrant. His hair sticks up in all kinds of ways and
he looks truly like the whore he is.
Sam breaks the staring contest to bend down and reach for the pockets of the
jeans still pooled around his ankles. He takes out every bill in there and
tosses them onto the bed next to Dean, smirking when some of it lands in come.
Dean’s eyes widen when he takes in the amount strewn around him. With that sum,
he knows that Dean and his younger self can make it well to next month with
some extra to spare.
“This earns you another round, y’know,” Dean adds quietly, voice shot.
“This is all I’m buying, now get dressed and gone, kid.” He knows Dean wants to
take a shower, but Sam’s not giving him that, knowing that Dean will have to go
back to his room, to younger Sam who will still be up, and Dean will have to
explain himself. He doesn’t care
He takes off his shoes and pants as he waits for Dean to gather his stuff and
get going. When Dean’s all ready, pocket bulging with the cash Sam gave him,
Sam lets Dean have a good look at him. He smiles at Dean, baring his teeth as
he points to himself and to the room around them, “be sure to remember this,
Dean-o.”
Dean gives him a puzzled look before he disappears, softly closing the door
behind him.
Sam stands in the room a bit longer, eyeing the dirty sheets. He scratches idly
at his pubes and kicks his shoes away, making his way to the shower. He cleans
himself, perfunctory, and returns to his room, absently wondering how he’s
going to get back to the future, when there’s a knock on the door. Not
bothering with anything to cover himself with, he opens the door to find his
younger self standing on the other side – short and soft, with big eyes and too
much hair.
Young Sam is blushing beet red under the scrutiny, but Sam can see the
determination on the boy’s face.
Holding out a small fist with a wad of cash in it, he blurts out, “we ain’t
taking your money, mister.”
Sam laughs scoffingly in his face. “Of course you’re not.”
He’s about to shut the door, but his younger self worms his way in to the room,
throwing the money on the ground.
“Like I said,” Young Sam continues, thrusting his pointy chin up in defiance,
"we ain’t taking this kinda money.”
“Oh, Sammy,” he replies, relishing how his younger self physically recoils. Sam
kicks the money on the floor out the door as his younger self watches on with
wide eyes.
“I don’t care if you take the money or not. Dean earned it being a good whore.”
Anger and hurt war with one another on Sammy’s face with every word he hears.
“You can either let the money go to some lowlife in this motel, or you can take
it, pretend you don’t know where it comes from so Dean doesn’t have to whore
himself every night to feed you for the next month. You choose.”
Sam watches as the pride in his younger self disappears with every word Sam
tosses out. When he’s done, the boy bends down in resignation and slowly
gathers every single bill. When he’s finished, he stands up again and looks at
Sam, studying him. He is still stark naked, and Sammy eyes him from head to
toe.
Winking at his younger self, he adds: “It’s okay to look, Sammy. This is your
future in say… fifteen years anyway.” When the boy just gapes at him in
astonishment, Sam growls out a, “now scram.”
Sammy hurries away while Sam closes the door. Dragging his hand through his wet
hair, he turns around preparing for a night of nothing when he spots Cas.
Before he can get a word in, Cas grabs his arm with brute strength and he’s
back to the present. He must be, because his older brother is there, color high
on his cheeks as he draws his arm back and knocks Sam out.
---
End
End Notes
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