Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/9893795.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Castiel/Dean_Winchester
  Character:
      Dean_Winchester, Castiel
  Additional Tags:
      First_Kiss, First_Blowjob, First_Time_Bottoming, First_Time_Topping,
      First_Time_Falling_In_Love
  Stats:
      Published: 2017-03-03 Chapters: 6/6 Words: 3858
****** All Your Firsts, All My Bests - Abandoned Project* ******
by coplins
Summary
     This is a Destiel fic I started a long time ago. It looks like I'll
     never end up finishing it. I was hoping someone might get inspired
     and maybe feel like co-write it so it gets finished? It's mostly smut
     though. Two chapters are done, third chapter partly done, for those
     who wish to read. Remaining chapters are writer's notes. Basically,
     Cas has had all Dean's firsts, and Dean all Cas' bests, but they
     never knew it or recognised each other until now.
     Working title:
     All Your Firsts, All My Bests
     After a wet office party, Cas goes out drinking with a couple of
     colleagues and clients. At the bar, they start telling each other
     about their first times. Cas can barely remember his first times, but
     he does remember his bests and tells the group about his first best
     kiss. It turns out that one of the clients just happen to be the boy
     he kissed. As the client tells the group of his firsts, and Cas about
     his bests, a pattern emerges...
***** First kiss... *****
**** 30 years old - 2010 - Trendy bar in New York ****
“My firsts weren’t that memorable. But I can tell you my first bests,” Cas
smiles at the coworkers and clients across the table. Liquor has been flowing
freely at the office party and when it ended some of his colleagues and invited
guests had decided to keep up partying by going to a nearby bar. The topic had
turned into sex and first times. “My most memorable french kiss happened when I
was twelve. I had kissed before, but this one… It was like we were made for
each other. Not until I was fifteen did I meet someone who kissed just as
perfectly.”
“So what happened?”
“I was at a party, living in Kansas at the time. We were playing Postman’s
Knock. There was this boy who got paired up with me. He didn’t want to kiss me
because I was a boy, but the other kids more or less bullied him into it. It
was fantastic. But it wasn’t until after the party that I got the best kiss. He
and I were waiting outside for our rides…”
===============================================================================
**** 12 years old - 1992 - Lawrence, Kansas ****
“I can’t kiss him! He’s a dude!”
“So? You a chicken, or what?”
“No! But―”
“Dean’s a chicken! Pock pock pock!” The children playing a variation of
Postman’s Knock starts chanting that he’s a chicken. Dean huffs in frustration
and looks at the boy he’s supposed to kiss. The boy is just standing there
patiently looking at Dean with his huge blue droopy eyes under a fringe of
light brown hair. He is not chanting, just looking kinda sad.
“To hell with it…” Dean mutters and throws up his hands saying “Fine!” loud
enough for everybody to hear. The chanting dies down and is replaced by giggles
and a tense hush. He walks up to the boy and glares at him, daring him to
protest. He just looks apprehensive. Dean has kissed girls before on the mouth.
But this is going to be his first french kiss. Just his typical luck that it
had to be with a boy. “You ready with the stopwatch?”
“Yeah, go ahead. 30 seconds starting….NOW!”
Dean leans in and presses his lips against the boy’s mouth (soft, no difference
from kissing a girl), he opens his mouth and experimentally pushes his tongue
in. It feels weird and wet. The boy kinda pokes at his tongue with his own at
first but resorts to letting Dean take the lead. It takes Dean 6 seconds to
decide he likes it. It takes the two of them 15 seconds to establish some kind
of balance with how relaxed/active their tongues should be for it to feel the
best. It takes Dean 30 seconds to figure out that 30 seconds is not enough.
When they break apart Dean fights the urge to chase after the boy’s mouth. They
stare dumbly at each other for a moment while their audience hoots and cheers
before Dean gathers his wits around and turns around smirking. “See? I’m not a
chicken!”
Later, Dean is waiting outside. Dean has kissed two more people - girls -
during the game. But stupidly enough, the first one was the best. He and the
boy are the only ones left still waiting to be picked up by their parents. The
boy is leaning against the wall just like Dean, only a few steps in between
them. He keeps throwing surreptitious glances at Dean, looking like he wants to
say something.
“What?” Dean says at last when the silence is getting too awkward.
“I’m sorry they forced you to do it,” The boy says looking regretful.
“Yeah, well. They forced you too.”
“No, I… I considered myself lucky. You’re…” the boy blushes and looks down on
the ground, “the most good looking person at the party. I-I liked it.”
“You liked it?” Dean asks, surprised.
The boy looks up and nods solemnly. “Yes. Very much. Sorry if that bothers
you.”
Dean looks down at his shoes and rubs his neck. Boy or not, Dean is ever the
opportunist. “I liked it too. Wanna do it again?” he asks and looks up at the
boy.
“Really?” The boy’s eyes go huge.
“Really,” Dean smirks. The boy nods eagerly but still looks like he doesn’t
really believe Dean. So Dean goes the distance that separates them, and with
the motto ‘Offense is the best defence’ he leans in for a kiss. And holy
fucking hell! it’s better than the first one now that they’ve gotten a hang of
it. It’s like they were made for each other. It turns into (although Dean
doesn’t know it yet) the best make out session Dean will have for years to
come. In hindsight, Dean is going to consider this a pretty innocent make out
session. Really. They’re just holding onto each other and kissing, and kissing
some more, and more. For maybe ten minutes before Dean’s dad’s car honks,
startling them to jump apart. They stare at each other, out of breath, possibly
a bit stunned. Then Dean once again gets his wits about. “Gotta go. See ya!” he
says with a cheeky grin and runs to his father’s car.
His father does not look pleased when Dean gets in and buckles his seatbelt.
They start driving away. “Dean,” his father begins.
“I know, I know. It’s wrong. I’m sorry.”
“You’re only twelve Dean. If you could just wait a couple of years before you
start doing that…”
“Wait, what? That’s what you have a problem with? Not that I was kissing a
dude?”
“Why would I have a problem with that?”
“Because it’s wrong?”
“Why is it wrong?”
Dean is baffled. “I dunno. Isn’t it illegal in places and stuff?”
“Yes, but in North Carolina, it’s illegal to sing off-key. That doesn’t make it
wrong,” his dad argues.
“Huh.” Dean is silent mulling it over for a while. “So you don’t mind me
kissing boys, you just want me to wait a couple of years before I do it?”
“Yes.”
A cocky lopsided smirk spreads on Dean’s face. “Dad. You know that’s not gonna
happen, right?”
His dad snorts a laugh, throws him an amused look, and says “I’m going to let
your mother have ‘the talk’ with you when we get home, son.”
“The talk” was an awkward affair by all means. But also kind of interesting.
And despite his dad’s attempt to delegate he got roped into it too in the end.
Maybe, in alternate universes, if there are any, Dean’s parents wouldn’t be so
at ease with the issue of their oldest son hitting puberty and discovering his
sexuality. But in this one they were. So Dean never had to go through any
internal crisis about liking, well, turns out - essentially anybody and
everybody. Which was a good thing. Sadly for Dean though, the boy was never
seen again before the Winchesters had to move. For a while, Dean thought about
him often. But it faded with time.
**** 30 years old - Trendy bar in New York ****
“Holy shit! That was you!?! It took me more than a year to stop looking for
you!”
Cas eyes snap up to meet the incredulous wide-eyed green gaze from one of the
clients sitting by the end of the table. Cas hadn’t even noticed him until now.
He’s gorgeous. And has freckles. If he truly is the boy Cas just told them
about it would explain Cas’ obsession with freckles.
“Did your dad drive an Impala 67?”
“Hell yeah. Fuck yeah,” the client grins. “And that was my first french kiss to
boot. Best makeout session I had for years. The next time I met someone who
kissed as good as you I was fifteen. Which, by the way, coincides with the
first time I received a BJ.”
“Go on,” one of Cas’ colleagues urges. “Tell us about it!”
***** First BJ... *****
**** 15 years old - 1995 - Baltimore, Maryland ****
Fucking costume parties. Dean’s dressed as Batman and is sweating under the
mask. He'd chosen Batman because there are always girls dressed as Catwoman or
Poison Ivy at these parties. A surefire way to hook up, right? You've got the
flirting part served on a plate - including jokes about stealing kisses from
Batman. But lo and behold, there were at least five Pocahontas, but not a
single Catwoman. Or any character from Gotham for that matter. All of his
carefully thought out pickup lines had failed miserably.
Plus he needs to pee. It’s lucky this costume is a two piece, otherwise, he
wouldn’t know what he'd do. He jostles his way through the crowd to one of the
toilets. There’s a queue, so he goes to find the other one. It’s locked. He
waits, the need to pee getting worse by the second. He knocks. “Oy! Could you
hurry up? My bladder’s about to explode.”
“Sorry! It’s gonna be awhile. Got the runs badly!”
He curses under his breath and throws a look across the room. There’s still a
queue by the other toilet.
Maybe there’s a toilet on the other floor?
He hurries up the stairs. This floor is off limits. He knows that. But if he
doesn’t pee soon something embarrassing is about to happen. Granted, he doesn’t
know many people at this fancy-ass house party, but it would still be a
humiliation he’d never live down. He tries a couple of doors - bedrooms, a
closet, then, bingo!
He sees the toilet, hurries inside, locks behind him and struggles to get the
costume bottom down enough to pee. It feels like he’s about to explode. The
relief when he finally has his dick out and starts emptying his bladder is so
great all his hairs stand on end and he has to support himself with a hand
against the wall, not to sag.
“Dun-un-un-un, nun-un-un-un, Batman!”
Dean jerks in fright at the voice behind him, heart hammering in his chest and
pee going everywhere for a beat. He turns his head to see (the now chuckling)
speaker, lying in the empty bathtub fully costumed, cradling a bottle of Jack
Daniels. “Christ, dude! Not cool.”
“I’d say. I’m the one who’s going to get blamed for peeing on the wall,” the
stranger says dryly with a lopsided smirk. He’s wearing a Robin costume. Not
some cheap shit like Dean, but a Batman Forever-Robin replica. Must have cost a
fortune.
“This your house?” Dean asks. He’s unable to stop peeing, but he tries to pull
his pants up enough to cover his ass at least.
“Mhm. And this floor is off limits for guests.”
“I know, but I was literally about to pee myself. And what the hell are you
doing up here if this is your party?”
“It’s my party and I cry if I want to, cry if I want to…” Robin sings with a
sarcastic expression. “I only host it because it’s Halloween and my parents
think that’s what kids ought to do. I hate parties. This party sucks.”
“Yeah, buddy. I’m gonna have to agree with ya. I think I’ve flirted with every
skirt at this party and struck out. All I wanted was to get some action, if you
know what I mean? But it’s gettin’ late. Gotta be home in an hour or mom will
have a fit,” Dean says and shakes himself off before tucking himself back into
his pants. He turns around to find Robin smirking at him.
“Lucky for you then, Batman, that Robin’s here for the rescue,” Robin say, then
holds out the bottle to him.
Dean takes it. “Thanks,” he says, takes a swig, and shudders as the strong
liquor burns his throat and land like a warm ball in his belly.
Robin heaves himself up out of the bathtub and comes to stand in front of him
with that sly smirk. Dean holds the bottle out to him, but he doesn’t take it.
Instead, he steps closer with a little shake of his head. “I can drink later.
You just told me we’re on a time limit.” He leans in looking at Dean’s lips,
licking his own.
Dean’s heart begins to jump when he gets what’s about to happen. He’s not sure
if he should push the guy away or not, but Robin doesn’t give him much time to
think. Between a breath and another Robin’s lips are on his, and a tongue is
questing for entrance. Dean thinks Robin has balls of steel. Going for another
guy like this could end up with broken bones. But he opens his mouth willingly,
thrill upon thrill running down his spine, nervous butterflies flapping in his
stomach. Robin’s a great kisser. No. A Great kisser! He kisses like he’s
fucking made for it. Dean closes his eyes and lifts the hand that doesn’t hold
the bottle, and rests it on Robin’s hip.
Robin responds by reaching down and massaging Dean’s dick through his costume
pants, bold as day. Dean’s no innocent little angel. He’s made out with girls,
gotten to grind against them, suck on their tits, and even gotten to finger
them a time or two. But he isn’t used to anyone going straight for the prize,
even if he’s managed to convince a few girls to touch it through his clothes.
He pushes himself into Robin’s hand and makes a needy noise into the kiss.
Robin takes that as encouragement. As Dean’s getting harder Robin lets go just
to pry his hand down Dean’s pants and grip his dick and draw it out so he can
stroke it in earnest.
Holy shit! He’s giving me a handjob!
Dean’s never had someone give him an actual handjob before. And Robin’s acting
as if pulling someone’s naked dick out is completely normal. Dean’s inside is
sizzling, lighting up like fireworks. He bucks into Robin’s hand and pulls
greedily at his shoulders. He moans and gasps into the perfect whisky-tasting
kisses. This couldn’t get better than it is!
Robin suddenly tears himself away. Dean’s about to protest, but Robin falls to
his knees in front of him and without a moment of hesitation sucks Dean’s
cockhead into his mouth.
Dean’s knees almost buckle.
Holy Shit!
===============================================================================
**** 30 years old - 2010 - Trendy bar in New York ****
“Did you like my costume?” Cas asks with a smirk. On the inside, his heart is
beating with excitement. What are the odds that this stranger had been two of
his most memorable occasions?
“Your costume?” the client exclaims with wide eyes.
The other people around the table laugh. They start to get excited about the
coincidence too.
“Yes, mine. I was so frustrated when you offered to reciprocate, because the
costume was damned near impossible to get in and out of, and you had to leave.
No matter how cool it looked, I wished my parents would have bought some cheap
crap that could easily have been discarded.”
“I hated that costume for the exact same reason,” the client grins. “Our family
went on vacation. When we came back, I worked up the courage to go back to your
house. But there was this old lady telling me you’d moved.”
“Yes. My family moved often. I threw a fit, wanting to stay so I could find
you. But alas, nothing helped. You made quite an impression. I was somewhat of
a slut―”
“Still are,” one of his colleagues jokes and nudges Cas’ shoulder, making Cas
and the other laugh.
“True. But I pined for his kisses for years,” Cas goes on with a gesture
towards the green eyed client. “Best kisser I’d met. Didn’t find anyone to top
that until I was seventeen.”
The client’s blushing and bites his lip over a grin. His eyes are glowing. Cas
thinks that if this night doesn’t end with him getting to kiss those luscious
lips again, he might as well give up on life.
“What are you waiting for? Tell us about it!” A redhead woman sitting opposite
of Green Eyes urges excitedly. The others around the table agree, and Green
Eyes nods encouragingly.
“Very well. We were living in Indianapolis at the time…”
===============================================================================
***** First time bottoming... *****
**** 17 years old - 1997 - Indianapolis, Indiana ****
Cas silently wonders what he is doing here in this apartment. This is so not
his crowd. These are the popular kids, the cool kids. He is not one of them.
Oddly, they never seemed to realise. Every new school he went to, it took him
only a day or two until he got roped into the hip crowd. Despite being
meticulous with his studies, despite his eyeliner and pierced eyebrow, despite
his Dr.Who shirt, hair dyed black and his bangs constantly covering one eye. In
any new school, some jock or popular girl called dibs on him and it snowballed
from there. He was never bullied for his straight A’s or his looks, they
admired him for how good he was with sports and his arrogant self-assured ways.
They liked having him around. He didn’t know why. He certainly never felt like
he belonged. He was sick and tired of life. Not in the want-to-kill-myself way,
but in the I’m-bored-and-don’t-give-a-shit-about-people way. They move so often
he no longer bothers trying to keep in touch with people he gets to know. Yet
he has never missed one day at school. Which says a lot, since one year he
changed schools 15 times and still aced all his grades. His parents are, well,
who knows? Diplomats? Lobbyists? Secret agents? Frankly, Cas doesn’t really
know, nor does he care. The important thing tonight is that they’re out of town
for the weekend and he is set on getting laid. This party is in the same
apartment building that they’re currently living in so it shouldn’t be that
hard to find a hookup and lure them up to his apartment for a good fuck. (Or a
bad one. You never know.) But currently, Cas is debating if he really is that,
desperate because he hates parties and he is yet to spot someone that catches
his attention.
“Hey C! Wanna join us playing I have never?”
Well, why not? If he isn’t going to get laid he might as well get drunk. Cas
gets up and goes to sit down in the circle of boys and girls playing. He looks
to his left and Whoa! Hello there tonight’s catch! The guy seems strangely
familiar, but then again, when you move as often as Cas, sooner or later
everybody seems familiar. He is gorgeous. Model type. Long blond hair swept up
in a ponytail, broad shoulders, straight nose, plush lips, strong jaw, long
lashes and green, green eyes. Best of all, he has freckles. Cas has a thing for
freckles. He can’t really remember what started that off but he adores people
with freckles. And this guy has the exactly perfect amount of them.
The guy turns his head and catches him staring. Cas gives him a blatant once-
over, smirks and winks, revelling in the blush spreading over the guy’s cheeks,
making the freckles stand out. He doesn’t miss the tiny smile on the guy’s lips
when he looks away. In Cas' book, it means he has a chance.
The game goes on with the usual questions. Cas has to drink to every single
one. He is not innocent. Neither is ‘gorgeous freckles’ beside him it seems.
His own question is “I’ve never done drugs.” Which about sums up what he hasn’t
done pretty well. Gorgeous drinks to that, though. Alastair, a guy in Cas’
chemistry class, asks a question that is pretty tasteless if you know he has
made a sport out of taking girls’ virginities. “I’ve never been fucked by a
guy.” The interesting thing that Cas notices about that as he tips his own shot
down is that gorgeous freckles doesn’t drink to that. Cas leans over and
whispers “Do you want to?”
“Want to what?”
“Drink to that the next time you play this game?”
Gorgeous bites his lip. “Depends. You offering to make it happen?”
Cas smirks at him. “I live four flights up. Currently parental free zone. I’m,
indeed, offering,” he says, raising an eyebrow challengingly.
God is smiling at him and so is Gorgeous.
Five minutes later they’re making out in the elevator. Cas might be in love.
This guy is the king of kissing, making it hard to uphold any for of blasé
attitude. His knees feel like jelly and Gorgeous has green eyes worthy of
writing poems about. The elevator door dings open on Cas’ floor and he tears
himself away only to grab Gorgeous by the hand and hurriedly pull him along
towards his apartment. When he stops to fumble with the keys in the lock,
Gorgeous plasters himself against his back, kissing his neck so every hair on
his body stands up. Hands find their way inside his shirt, nails scrape over
his belly - tickling. Gorgeous grinds himself against his ass and Dammit! Cas
almost changes his mind about who’s topping tonight.
He should get an award of some sort for managing to unlock the door with
gorgeous distracting him so thoroughly.
Once inside they go back to making out, shedding clothes as they go, while Cas
backs them towards his room.
[NOT FINISHED]
***** First time giving head... *****
**** 21 years old - 2001 - Hawaii? Tropical island somewhere anyway ****
Writing notes: POV Dean. Beach *Cas has long hair here. Light brown, blond,
sunbleached streaks. He’s wearing pilot glasses he doesn’t take off during the
encounter. He’s about to leave the island and sells his surfboard to Dean in
exchange for Dean’s necklace and a BJ. Cas never takes the necklace off after
this and still has it under his suit in present day. Dean’s got mutton chops, a
goatee, and blue hair. Of course.
===============================================================================
***** First time topping... *****
**** 24 years old - 2004 - San Francisco, California ****
Writing notes: POV Cas. Dance club. Intoxicated. Dean’s got a full beard and
short hair. Cas has a moustache and a baseball cap that doesn’t come off. They
meet at the dance floor and go outside. They do it outdoors in a nearby park,
against a tree.
***** First time falling in love... *****
Chapter Notes
See the end of the chapter for notes
**** 30 years old - 2010 - Trendy bar in New York ****
Writer's notes: This is where it ends. They introduce themselves properly and
hook up, of course, they do. How could they not? After realising that they've
been searching for each other since that first kiss back in Kansas. This time,
when they wake up in Cas' apartment, they lie talking. They've been intoxicated
or on a time limit everytime they've hooked up before, but not now. They go out
to eat a greasy brunch to cure their hangover. Dean's just moved here and Cas -
no longer being yanked around the country by his parents - lives a stationary
life here. They talk and talk, and can't tear themselves away. Cas follows Dean
home just to walk him, but ends up staying the night. It goes from there. They
start dating, and spend every free hour with each other. Moving in together
doesn't take long. A year later they get married. You know how it goes. Happily
forever after is a thing. ;)
Chapter End Notes
     If you liked the story, or find yourself inspired to write one or
     several of the chapters, please, hit me up here, on twitter_
     (coplinz), or tumblr_(coplins).
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!