Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/976476.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Other(s), Dean_Winchester/Original_Male_Character(s)
  Character:
      Dean_Winchester, Sam_Winchester, OMCs, John_Winchester
  Additional Tags:
      Teen!Dean, doing_what_he_has_to_do, self_worth_issues, Prostitution, he's
      16, Angst, Shame, caretaker!Dean
  Series:
      Part 1 of to_hell_and_back
  Stats:
      Published: 2013-09-22 Words: 3496
****** a winter memory ******
by gillasue345
Summary
     They were broke. Broker than broke.
     Dad had left them only enough for two weeks and he was supposed to
     have been back a week and a half ago and Dean had been able to
     stretch it out. But Dad wasn't answering his phone. Dean had spent
     his last five bucks on bar cover, flashing his fake id at the bouncer
     who waved him in with a yawn.
Notes
     WARNING: TEEN!DEAN DOES THINGS HE SHOULDNT HAVE TO DO. tw: underage
     prostitution.
     Dean's self worth takes another hit. Dean is 16. Explicit sex. Don't
     read on if you're uncomfortable with this.
 
     Tommy walked up and said, "aren't you happy?" I said: "happy? why?"
                      ~Charles Bukowski~
 
===============================================================================
December, 1995
"Don't wait up Sammy," he said as he tossed his brother the last bag of Fritos
and a diet coke. "I'll be back in the morning, and lock the door behind me."
Dean said as he pulled the door shut.
"I know Dean, you don't have to tell me every f-fucking time!"
Dean barely rolled his eyes. Sam had begun swearing more in the past year, but
he still stumbled over the words. It was adorable. But as he pulled his jacket
tighter against him and walked down the street toward the local dive bar, he
heard the door lock behind him.
They were broke. Broker than broke.
Dad had left them only enough for two weeks and he was supposed to have been
back a week and a half ago and Dean had been able to stretch it out. But Dad
wasn't answering his phone. Dean had spent his last five bucks on bar cover,
flashing his fake id at the bouncer who waved him in with a yawn.
Unfortunately, the bar had no pool tables, and what the hell kind of dive bar
had no fucking pool tables? Sam was much better at darts than he was anyway;
there was no way he'd make enough to cover the room fee and groceries with
darts alone.
He took a seat at the bar, rubbing the back of his neck absently. A few seats
away a man dressed in a dark suit, woefully out of place in the rough and
tumble atmosphere of the bar, sat nursing a glass of whiskey.
"What'll it be, honey?" the bartender sidled up to him, leaning over far enough
that if Dean broke eye contact, which he totally isn't doing, he could see the
soft pink lace of her bra swell up beneath her ripped t-shirt.
Dean bit his lip. He couldn't afford a drink. But he watched as she took in his
appearance, the way her eyes widened just the tiniest bit, and smiled
crookedly, letting the barest hint of heat touch his eyes. He'd always been
good at getting what he wanted with his looks.
"What's your specialty?" he asked, intentionally lowering his voice, smirking
as her cheeks blossomed pink under her too-pale makeup. Her blue eyes sparkled.
"I make a mean Jack and Ginger," she whispered.
Dean reached over the bar, letting one finger trail from the crook of her elbow
down to her wrist, where he felt her pulse jump. "I guess we'll see," she said.
She pulled her hand away slowly, her lips curling up into a smile as she turned
away.
She brought him his drink, and Dean made the effort to pull out his wallet, but
she just shook her head, resting her hand on top of his.
"On the house, sugar."
Dean barely suppressed his smirk. Perfect.
"Thanks sweetheart," He felt the beginning tingle of desire crawl into his
belly. He could take her home, have some fun. Maybe find a stash of cash
somewhere once she was asleep.
He was just about to take his chance when she raised her left hand to brush
away her blonde bangs. And his stomach dropped. There, sitting on her left ring
finger, was a plain gold band. She caught his crestfallen expression and
smirked back.
"You didn't think I'd actually fall for your pretty boy routine did you?" Dean
shrugged.
"It was worth a shot," he downed the rest of his drink and winked at her. "You
have a good night, darlin'" He smirked in a 'your loss' kind of way before
turning away.
He made his way to the restroom, if you could call it that. The urinal was
cracked; it was slowly leaking, a puddle forming on the urinal mat. The toilet
in the stall looked as if it hadn't been flushed in a week. 
The acrid smell of puke and piss assaulted his senses and he took a moment to
splash his face with lukewarm water. How am I gonna get some cash now? He
couldn't afford the cover to another bar, and he sure as hell wasn't looking to
get shot at some random chick's husband.
The door to the restroom opened up and Dean whirled around as he heard the
sound of the door locking behind the new occupant. The man in the dark suit was
standing in his way, blocking the bathroom exit.
He nodded his way and tried to get past the new arrival, but the man just
maneuvered back in Dean's way; his arms crossed over his chest. The man was
thin and lanky, a few inches shorter than Dean. He wasn't a physical threat,
but unease began to rise within him anyway as he watched the man stare brazenly
back at him.
"Having a good night?" the man asked, his voice was high and reedy and Dean
winced. It didn't match his demeanor at all.
Dean shrugged, rubbing the back of his neck with the palm of his hand.
"Could be better," he hedged, avoiding eye contact unless his understanding of
the situation was wrong and he was about to get his ass kicked.
The man was advancing now, entering his personal space, his brown eyes were
dull and his dark hair looked greasy in the pale fluorescent light, but there
was something alluring about him. Something Dean couldn't put his finger on. He
definitely wasn't reading him wrong.
"Oh yeah, sugar,  how's that?" The guy brushed his finger along Dean's forearm,
in much the same way that he had done just a few minutes ago with the
bartender. But Dean paused. Did he dare? He could easily fight his way out of
this. All he'd have to do was get the guy in a headlock. It would be easy,
routine. Dad would probably be ashamed that Dean hadn't done it already, that
he was hesitating.
But.
They needed the money. Sam was a bottomless pit of hunger since he'd shot up
six inches in the past six months. And Dean had noticed that Sammy's boots had
become too small. He figured he could always hand down his own boots, but a
small, selfish part of him didn't want to; he had just gotten them broken in
and Sam always complained that their arches were too different to share shoes.
And it isn't like this is the first time. If he had to sell his body, so be it.
It was just another tool in his arsenal. 
So he took a chance. "It'd be a whole lot better with a couple dead presidents
in my pocket, that's for damn sure." He looked at the man through his eyelashes
and licked his lips. He swallowed thickly and the man's gaze was drawn to
Dean's Adam's apple. 
"Oh, and which presidents would those be?"
The man pressed closer. Dean could smell his expensive aftershave. He could
feel the soft material of his suit beneath his fingertips as he steeled his
resolve and placed his hands on the other man's shoulders. The man obviously
had money. What he was doing in a dive like this, Dean could only guess.
"Big Ben and a couple of his twin brothers, and I bet we can have loads of
fun." Dean figured he'd go big or go home. the guy seemed to know what that
amount of money entailed, and his eyes widened for a moment before they
crinkled at the corners.
The John nodded. He trailed his finger tips across Dean's cheeks, over his
freckles and his too full lips.
"Let's get out of here then," Dean said, as he followed the guy out of the bar.
He gestured to the shadows in the back alley, where they were less likely to be
seen or heard, but the man shook his head. 
He hesitated as they reached the dude's car, a prissy little Nissan with rims
that probably cost more than Dean's custom M1911. He knew he shouldn't get in
the guy's car, that it could spell trouble, but he palmed the knife he kept
hidden in his jacket pocket, and felt the cool touch of a blade against his
ankle and felt safe.
If it went sideways, he could handle himself in a fight. His father had made
sure of that.
And so when they pull up to the swanky apartment building with its rigid
doorman and fucking stone faced elevator attendant, Dean just goes along for
the ride. The doorman had referred to the creep as Mr. Johnson, and Dean had to
snort back a laugh, but if all else fails, at least he has a name to go with a
face now.
Not like the cops would actually do anything about it, except maybe arrest
him. 
They arrived at the man's apartment, and it's the ridiculously modern yuppy
monstrosity that Dean had fully expected it to be.
Mr. Johnson shut the door behind them, locking it tightly before turning back
to survey Dean in his living room.
He pulled off his tie deftly, letting it drop on the floor before he grabbed
Dean by the shoulders and crashed their lips together.
His lips were surprisingly soft, and Dean let out a small yelp of surprise at
the man's insistent tongue.
Dean pulled away, shaking his head as he did so. "No more kissing," he mumbled,
his heart pounding. The man seemed to take this in stride. He pulled Dean's
leather jacket off his shoulders, latching his mouth around the pressure point
behind Dean's ear that never failed to set his blood boiling.
Dean barely suppressed a whimper of want. He has to do this. But he sure has
hell shouldn't be enjoying it.
Of course, that doesn't stop the heat from pooling in the pit of his stomach or
the seam of his jeans to become uncomfortably tight.
"What do you want?" Dean forced out as the man's fingers slowly skimmed over
his belly beneath his t-shirt and up towards his nipples.
The man pulled away. His eyes were almost black with desire, his pupils blown
out so much that there was barely a hint of brown around the edges.
"I want you to fuck me, I want your mouth on me... in me." the man's voice
broke, and for moment Dean almost felt sorry for him. It certainly wasn't what
he was expecting. He raised his eyebrows. 
Usually, if Dean ever did... indulge... in this forbidden fruit, he was on the
receiving end. But it couldn't be much different than when he was with girls
could it?
He pulled the man to him, quickly undoing the buttons of his dress shirt and
placing a kiss over the man's collarbone.
He stopped when he reached the man's pants however, and just stared at him. He
was attractive in an older dude kind of way, Dean mused, but he ain't doing
this for free and Dean pulled back, holding out his hand, feeling the shame and
guilt well up in him until he was choking on it. But the man simply sighed and
reached into his back pocket.
He pulled out three bills and placed them gently in Dean's hand, but Dean
hadn't missed the wad of bills still waiting in the dude's wallet. He put the
bills in his wallet and replaced it in his pants. Then he took off his shirt,
allowing it to fall to the ground next to his jacket. He kicked off his boots
and let his jeans fall to the ground, but he left his socks on. 
The man tried to kiss him again and Dean just shook his head. He threaded his
fingers through the man's shaggy hair and pressed open mouthed kisses along
Johnson's throat, pausing to suck a bruise over his pulse point. 
Maybe I can get him to fall asleep-- an errant thought occurred to him and he
pushed it away. They weren't quite that desperate yet. And 300 dollars would
more than cover their debt until Dad came home.
Dean was a lot of things, but he hated stealing more than anything else, mostly
because of the disappointed look on Sam's face when he found out. 
He didn't like handouts and he would prefer to earn his money, even if the
means by which he earned it made his stomach roil. But he would steal if he had
to, or if this guy got out of line.
They made their way to the wide leather couch and Dean would be annoyed that it
was so fucking soft if they had been in any other situation.
He let his boxers fall to his ankles and then quickly, clinically, he stripped
Mr. Johnson of his remaining clothing.
Then the man did something that Dean did not expect. Slowly, with the reverence
of a man in church, he pulled Dean's fingers into his mouth. He swirled his
tongue around his digits, but then pulled away, reaching into the side table
and pulling out a condom. he tossed it at Dean and then brought Dean's hand
back up to his mouth.
Dean ripped open the condom with his teeth, rolling it on deftly, trying not to
be distracted by the man's mouth on his fingers.
Once his hand was spit slick, the man lay back, brushing Dean's fingers on his
hard cock, and jerking lightly at Dean's soft touch. Dean prepped him slowly,
blushing at the sounds Johnson was making at his touch.
Then suddenly, the man pushed his hand away. His eyes were dark, wild.
"I want your mouth in me, baby," he barely whispered, but Dean felt himself
flush from the roots of his hair to his chest. He'd never done that before. It
almost turned his stomach to think about even doing it. But the guy wasn't that
bad. He hadn't hurt him, and he'd asked for it upfront. And he'd paid extra, so
why the hell not? It was a beautiful and natural act, he just repeated to
himself.
Or not, he thought as he closed his mouth around the rim of the dude's ass and
nearly gagged. The overwhelming smell of musk and sweat and ass had him choking
up the Jack and Ginger from the bar, and he had to take a deep breath through
his mouth and out his nose to stop himself from throwing up.
But the sounds that the man above him were making were positively sinful, and
after a moment, the smell and taste faded into the background leaving him with
only sensation.
Eventually, Dean began to add fingers, watching as the man jumped every time
his fingertip brushed his prostate.
He pulled away, gasping and panting as the man groaned loudly. "What do you
want?" he whispered to the man writing beneath him.
"Fuck me, please, please fuck me," the man gasped, and Dean stroked his own
cock for a moment, before lining it up at the other man's entrance. He groaned
as he pushed in, the man was tight yet pliant against him, his body tensing
around the intrusion, then relaxing.
He pulled back incrementally, then thrust back in. Johnson gripped him at the
shoulders, lifting his legs to allow more access, and Dean couldn't help the
moan that rose to his lips. He watched shamelessly as the other man's cock
bounced in time to his thrusts, how the man's hand wrapped around his own cock,
fisting the head with his palm and squeezing he vein underneath with his thumb,
swiping once, twice, three times it over the slit.
And Dean pretended that it didn't turn him on. The man below him was a moaning
mess, thrashing down and against his cock, and that fact didn't make his
stomach clench in tight pleasure, bringing him closer and closer to his own
release.
"There," the man moaned. "Right there, oh fuck," Johnson panted, meeting Dean
thrust for thrust. He brought the hand that wasn't occupied with his cock up to
Dean's throat and his fingertips brushed the short hairs at the nape of his
neck and Dean had to bite back his own moan. 
And when the man came all over his own stomach, moaning loudly the name of
someone that Dean didn't know, Dean let go too, stilling inside this other man,
pressing him down with the aftershocks of orgasm. His knees nearly gave out
beneath him and it was all he could do to remain upright.
Dean pulled out then, his face burning bright with shame after coming down from
his high. The other man was lying boneless against the couch cushions, his face
flushed and a slight sheen of sweat on his brow. He reached over to the side
table and picked up a Kleenex from the waiting box and cleaned himself off
before offering the box to Dean. Dean pulled the condom off, wrapping it in
tissue before dropping it into the man's waiting hand.
The man then flipped Dean down, placing the softest of kisses to Dean's mouth
before he could pull away.
"Thank you," he mumbled quietly against Dean's chest.
Dean dressed quickly after that. He turned to look once more at the man who was
slowly drifting to sleep on the couch and then returned to him.
He let his fingers slide through the man's messy hair for one moment before he
pulled the throw blanket over the man's naked body.
"Goodnight, luv." The man whispered to someone who was most definitely not
Dean. And Dean felt a stab of envy for this man's lover. What must it feel like
to love someone so much that even when you're with another, you yell out their
name as you come.
The man fell asleep pretty quickly after that, and after a moment's hesitation,
Dean reached into his wallet and pulled another hundred.
He left then. Ignoring the smirk of the elevator attendant and the scowl of the
doorman as he made his way out of the apartment and began to walk the fifteen
blocks to his and Sam's motel room.
When he got back, he found Sam sprawled out on his bed, an ancient book about
werewolves lying open over his face.
Dean sighed, taking the book and placing it on the bedside table. He pulled the
covers up from the end of the bed until most of his brother was bundled up like
a burrito then he headed toward the bathroom.
Dean turned the water on full blast and stripped. He took the hottest shower of
his life, ignoring the sobs that racked through his chest. He brushed his teeth
twice, but still couldn't get the taste of the man off is tongue.
Once he was finished, he dressed fully and climbed into his bed. After tucking
the money away in a secret pocket of his jacket, he rested his hand around the
knife beneath his pillow and silently willed the tears to go away. Eventually
Dean drifted off into an uneasy sleep, the weight of the money in his pocket
causing him to have nightmares of all the ways it could have gone wrong. 
The next morning, Dean was awoken by the sound of the lock turning in their
doorway.
He was awake in a flash, his hand on his knife, but then he relaxed as he saw
the graying hair of his father in the doorway, followed quickly, like a punch
in the gut and then the balls, with the realization that Dad was home, and that
once again, his efforts were proven to be unnecessary and never, ever spoken
about.
John just tossed a few more hundred dollar bills onto Dean's bed, "Will that
cover you?" he asked, his tone was definitely annoyed. Annoyed that Dean had
run out of money, annoyed that he had had to come all the way back here because
Dean wasn't responsible enough to handle having a budget.
Dean just nodded; this shame was a thousand times worse than anything Mr.
Johnson ever could be. It welled up inside Dean, replacing his anger until that
had only been a memory. Shame was the only thing he could feel now. Shame
because his actions weren't even needed. That he could have just held on,
waited, given Sam his lunch money and gone hungry just another night and he
wouldn't have had to stoop so low. 
"Yes sir," he said and his voice broke. A single tear fell down his cheek.
"That should c-cover it."
John nodded and pulled his duffle back over his shoulder. "I'll be back in a
few more days. And, dammit Dean, make sure Sam gets to school on time. The damn
teacher keeps calling my cell."
Dean looked down again. "Yes, sir."
And with a nod, John was out the door.
When Sam woke up a few hours later, he didn't mention the redness of his
brother's eyes or the money still scattered across Dean's bed.
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