
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/4949683.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester, Sam_Winchester/Original_Male_Character(s)
  Character:
      Dean_Winchester, Sam_Winchester, John_Winchester, Original_Characters
  Additional Tags:
      Companion_Piece, Fluff, Memories, Childhood_Memories, Pool_&_Billiards,
      Pre-Series, The_Coldest_Circle_of_Hell
  Series:
      Part 2 of The_Devil's_Kiss_Sequence
  Stats:
      Published: 2015-10-15 Chapters: 2/? Words: 2619
****** The Best of Times ******
by OmniscientPhoenix
Summary
     On the first night in hell Lucifer offers Sam a deal: stop fighting
     and Sam will get to relive his best and brightest memories once a
     year.
     This is not the story of the bad days.
     This is the story of all good ones, the light in the shadows.
     This is the story of how the boy with the demon blood survives Hell.
     Companion fic to the Coldest Circle of Hell. Can be read as stand-
     alone.
Notes
See the end of the work for notes
***** Prequel *****
Chapter Summary
     Sam makes a deal.
The first night in hell Lucifer offers him a deal. 
Submit, play nice, earn a reward.  
See, the Cage is a sandbox of nightmares and torture and fear.  But if you know
how to work the system the same magic that fuels the horrors of the cage can be
redirected to create something so much better.   
Submit, play nice, and live out the best and brightest memories one day a year.
   
Sam knows better than to make deals with the devil.  
But, it can never be said Lucifer isn't persuasive.  And boy does he persuade,
with glimpses of the Fourth of July and the brother he thought he'd lost
forever.  
Seal the deal with a kiss, just the way the demon's do.
The devil's kiss brings bad days, horrible days.  And Sam knows if he had a
choice, he'd take the deal all over again.    
This is not the story of the bad days.
This is the story of all good ones, the light in the shadows.
This is the story of how the boy with the demon blood survives Hell.    
 
***** Blue Chalk Fingers and Felted Tabletops *****
He knows it's a good day, a memory because he wakes up to a scene so far
removed from the Cage it's not really on the same plane of existence.  
Which it's not the same plane, not really.  It's a seedy dive bar that's seen
better days, dimly lit and worn around the edges much like it's patrons.
There's a figure at the bar flirting with the pretty, brunette bartender and
Sam smiles.  It's Dean, impossibly young, only twenty or so and he turns toward
Sam with a grin and a beer in one hand.  He walks over, pulling a drag from the
glass and Sam realizes not for the first time that the sight of his brother's
lips wrapped around something shouldn't make him shiver like that.
"Heya, Sammy.  You ready?"  
Dean’s breath smells like the $2 beer on special, bitter and hoppy.
"Ugh, your breath already smells like a brewery, dude.  How's that even
possible?" 
In reality, Sam doesn’t really mind the smell.  Cheap beer mingles with Old
Spice and aftershave and motor oil, a smell so entirely Dean that Sam feels
himself unconsciously relax as he breathes it in.  He remembers a random fact
from freshman bio, remembers that scent was the first sense to develop in their
ancient ancestors.  They used it as a form of identification and he supposes
his response to the mere smell of his brother makes sense.  Ancient evolution
transformed into modern recognition.  Not that the science of the thing really
matters.  It's the smell of home and that's something no scientist will ever be
able to describe. Maybe art could come close, but even then it falls short of
the real thing, musky and so very real.  Even in the form of a memory.  
Sam remembers this particular day well and it's one of his favorites.   
Dean had dragged him here to teach him how to hustle pool.  John'd been gone
for a solid three weeks, something about tracking a vamp nest and while that's
par for the course, the absence's not doing Dean’s wallet any favors.
“Gotta keep my Sammy in Lucky Charms and Spaghettios,” Dean chuckles when he
suggests it and while Sam prefers more legal means of income, he's more than
willing to help out.  He’s not a kid anymore, notices when Dean mumbles
“Already ate” more often than not and even with Dean giving up his share of the
food Sam’s stomach still grumbles when he lays in bed at night.  It’s not
enough food for one of them, let alone both, but they share as best as they
can. That is when Dean's willing to take what Sam offers him.
So, they're standing in the middle of some dive called O’Leary’s.  Of course,
Sam’s not old enough to be in here, won’t be for another five years but it’s
not the kind of establishment that would care.  It's not as if he's drinking
and he’s tall enough for the bartender to claim ignorance should anyone
official come asking. 
“Alright little brother, let’s practice," Dean announces gesturing to an
unoccupied table.  
Sam's played this game before, not that Dean knows that.  In fact, he's a
pretty good at it.  After all, it's a game based on things he understands,
geometry and physics, forces and angles.  Dean thinks Sam's never so much as
touched a cue, but he's more than willing to clear up that misconception.  Dean
gets off on big brother superiority way too often for his taste.  
Dean’s at his side, glass of cheap beer in hand and he smiles, lips pressed
against it as condensation drips down the side. 
“You ready, Sammich?  We’re gonna teach you a real life skill, kid.” 
He rolls his eyes and snatches a cue.  “Whatever you say, Dean.” 
“I’m serious, Sammy.  You’ve gotta learn how to play the game.  Requisite
Winchester skill.” 
He doesn’t even bother replying, plucking balls from the pockets and rolling
them towards the right end of the table.  He orders them deftly, knows the
rules of eight ball even if it's been a while.  He remembers helping Dean
memorize the rules when his brother turned fourteen, quizzing him on various
games from a beat up paperback lifted from the local library. 
He presses them tight inside the wooden triangle, making sure he doesn’t leave
space between the balls as he lifts the rack and sets it aside. 
“Nice rack there, Sammy,” Dean says and Sam glares up at him, flushing pink. 
“Keeping it nice and tight,” he wiggles his eyebrows and Sam can’t help but
snort. 
“Shut up, jerk.”
“Bitch.” 
He crosses over to Dean’s end of the table where he’s chalking the tip of his
cue, fingertips stained blue with chalk.  He elbows his brother, snatching the
blue square to chalk his own cue liberally.  He’ll be damned if he miscues
first try. 
“Alright, Sammich.  Ladies first,” his older brother gestures and Sam takes
that as the signal to break.
A shitty break means a shitty game and he knows his big brother's just setting
him up for failure.   
So when he lines up his cue and sends the white ball into the assortment of
solids and stripes with a resounding crack he can’t help the proud smirk he
shoots Dean, as one, two balls drop in the pockets. 
He lines up a shot and sinks another, before he sends a ball wild. 
“Stripes,” he announces smugly and Dean stares at him, incredulously. Not the
best start but as far as Dean knows Sam hasn’t had any practice at this. 
Doesn’t know Sam’s friend Luke (boyfriend, if he’s being completely honest) had
a pool table in his basement.
Sam blushes at the memory.  They used to play, out of ear and eye shot from
Luke's parents.  They'd get a few games in before Luke would press into his
back as he made a shot, press kisses into the nape of his neck.  Distracting
until Sam would give up, dropping the cue to the ground and pulling him in for
a kiss.  Sliding his tongue into the other boy's mouth, licking and biting
until they were both hard and heavy in their jeans.  He'd spread Sam over the
felt surface, yanking his jeans until they pooled at his ankles.  Press soft
kisses into his inner thigh until he sucked him down.  Sam learned a lot more
than pool in that basement and he shifts as he blood pools in his crotch at the
memory.
He's pulled back to the memory when Dean speaks again.    
“Nice, Sam,” he murmurs and he leans over, squinting one eye shut as he lines
up his shot.  “Left corner,” he announces, pointing with the cue.  That's how
the game's played, the Winchesters don’t play slop.  You hit the right pocket
or you might as well have missed the ball.  Crack, and an expert shot sends the
ball into the corner.  “Center,” another gesture, another ball.  He misses,
scratching with a grimace as Sam snickers and plucks the cue ball from the
pocket.
“At least you sank one,” he teases and Dean shoots him a glare. 
“Whatever, Samantha.  Beginner’s luck,” he grumbles and Sam lines up the shot
in the kitchen with a smirk.  He sends another two balls into their pockets.
They snark back and forth over the blue felt until the eight ball’s the only
one left and Sam’s left in a terrible position to sink the damn thing.
It’s a bank shot and he knows, just knows that he’s going to scratch because
that’s what he does every single fucking time.  Luke used to make fun of him
for it, he couldn’t master the elusive bank shot no matter how hard he tried.
“Basic skill, Sam.  No great pool player’s repertoire is complete without the
bank shot," Luke would laugh.
Of course, Sam would just grumble and kiss him until the other boy fell to his
knees.  The sloppy, sweet blowjobs were a lot more fun than the frustration of
sending the damn cue ball into the pocket right alongside the eight ball,
losing him the game.
That way they both won, he thought.  And he was right, Luke was enthusiastic
and Sam was more than willing to return the favor.  With a bit more skill he
thought, but he wasn’t going to complain.  Wet and enthusiastic was better than
a frustrated shower and conditioner slick hand.   
So of course he’s standing in that bar with Dean and he wants desperately to
win for reasons he’d rather not think about.  He knows he wants to impress Dean
and the more he thinks about Luke’s pool table, the harder he’s getting and it
doesn’t help when Dean crosses over to press into Sam’s side. 
“Need some help, baby brother?”He whispers and he’s too close, Sam can feel his
cock twitch in his jeans as a dark red flush travels from his chest to his
neck. 
“No- no,” his voice cracks and he shifts uncomfortably.  “No, I’ve got it.” 
Dean chuckles, a low rumble and Sam chooses to ignore the way the sound seems
to be directly connected to his cock.  “I’m here to teach you baby boy.  Teach
you things your little friend Luke never even dreamed of.” 
Sam chokes, knows his face flushes even darker and if Dean didn’t know Luke was
more than a friend before he certainly knows now. 
“That’s okay, Sammy,” he whispers in his ear, moist breath carrying the scent
of hops brushing over his ear.  “I don’t care who you sleep with.  Cute kid.” 
He chokes again and, fuck, his cock is reacting to the sound of Dean’s voice
and he needs a long, private shower.  Now. 
“I don’t know what you’re talking about,” he mumbles, tongue tripping over the
lie and Dean laughs again. 
“Like I said I don’t care, Sammy.  But if you wanted to hide something like
that you shouldn’t have come home reeking of sex with your mouth all swollen
like that,” he presses a little closer and Sam can’t breath, can’t breath with
the smell of Old Spice and that rumble in his ear.  “I thought maybe you were
lying about going over to Luke’s to play pool, maybe you had a girlfriend or
something.  So I followed you one time and you know what?  Someone was sucking
your dick and it wasn’t some girl.  Just your little friend Luke.”   
Dean’s hand goes to his waist then, “I don’t care that you like boys, Sammy. 
Don’t care if you like girls.  Just wish you would’ve told me about it,”
there’s something tender in his brother’s voice and acceptance threads the
hunger there.  Unconditional love and Sam thinks that for all the teasing
there, Dean really does want him to know he doesn’t care that his little
brother likes boys or girls or both.  He accepts him and loves him and suddenly
the flush fades.  Sam nods silently, clears his throat.
“Okay, Dean.  Teach me.” 
He knows that he should be referring to the bank shot but something in him
desperately wants to drag Dean into the bathroom and get down on his knees. 
Wants to show Dean what he learned in that basement that doesn't involve cues
and chalk.  He imagines sprawling out on this pool table in front of all these
people, fuck the consequences, as long as he gets to see those pink, lush lips
wrapped around his cock. 
Dean looks a little pink himself as he adjusts himself so he's a long, hot line
pressing against Sam’s back. 
“It’s not that hard, little brother,” he murmurs, air brushing past the shell
of Sam’s ear.  “Just looks intimidating.” 
Gentle callused hands guide the cue so it’s lined up properly, pointing the
ball so it will hit the wall and bounce back into it’s proper pocket. 
“Don’t hit it too hard.  You’ll scratch.  Just the right amount of force,” Sam
presses back against his brother and in that moment he swears he feels the hard
line of his cock pressing into his ass, one that matches the tent in his own
jeans, barely concealed by the pool table.  He lines up his shot, expecting
Dean to step back but he doesn’t.  “Not too hard, baby brother.”
“Left pocket," and with a slow exhale Sam hits the ball, not quite as hard as
all those other times.  It sails into the pocket and with that Sam’s won, beat
his brother at his own game and Dean whoops, pride in his voice. 
“That’s it, Sammy.  Just like that,” and he’s peeling himself off of Sam’s
back, putting space between them now that the moment's over.  “Just like that.”
“Thanks,” a pleased blush spreads across his cheeks and he should be excited
that he finally managed the shot, but he's hard in his jeans and it's
incredibly distracting.
It's a little awkward, now that the moment's over and Dean clears his throat
nervously.     
“Wanna mess with those suckers over there,” his brother says, pointing to two
men that just walked through the door and Sam smiles. 
“Yeah, Dean.  After I win I’m taking you out for burgers.”
The men buy Dean’s story about teaching his little brother pool and they don't
need to agree to lose the first two games.  One hundred dollars later, Dean's
running towards the Impala, yelling at Sam to hurry up before he has to spend
the night stitching up his pretty-boy face. 
They escape, just barely, and at an all night diner Sam keeps his promise and
buys two burgers and an entire apple pie. 
It’s their first real meal in a week and nothing's ever tasted better. 
“Cheers to me for being the best teacher ever,” Dean announces, holding out his
Coke for a toast and Sam rolls his eyes, as he clinks his glass with his older
brother’s.
“Yeah.  Thanks, man,” he says quietly and it’s genuine.
Dean flushes a little at the tone of his voice. “Well you already knew.  I just
taught you how to take advantage of some shitheads with too much money in their
pockets.” 
Sam shrugs and smiles again, “Yeah.  And I’m gonna make sure those shitheads
are gonna keep you in burgers and pie.” 
After that night they play pool when funds run low and it keeps their stomachs
full.  As time goes on Sam gets better than his brother, hustling pool as
easily as Dean cheats at cards.   
Sam never admits the memories of Dean pressing him against the pool table fuel
his long, conditioner slick showers for weeks.
The memories that stick with him at hell stay with him for a reason.  
End Notes
     As mentioned before this work is a companion piece to my other fic
     "The Coldest Circle of Hell".
     If you enjoyed this fic and would like to check out the main story
     you can find it below at:
     http://archiveofourown.org/works/4820024/chapters/11036540
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!
