Dean Winchester is as straight as an arrow. He’s a lady’s man of epic proportions: the king of the one night stand, the messiah of the friends with benefits paradigm, the emperor of perpetual bachelorhood.
Except, apparently, when it comes to his best friend, Castiel Novak.
Dean and Cas went to high school together, but they ran in different social circles and only had a couple classes together. Their graduating class was small, so they were acquaintances and on friendly terms, but they only reconnected on a friendship level at their five-year class reunion.
When Dean is completely honest with himself, which is rare, he had always been kind of intimidated by Castiel. Cas was one of those guys who was popular in an infamous way. He wasn’t bullied and he wasn’t exactly a nerd. He was a lone wolf, a guy who had one foot in a dozen different cliques. He was the guy who looked at teachers like they were stupid, and had an answer for every question. He was the guy who made teachers say, “Oh, I hadn’t thought about it like that.”
Cas just had a unique perspective of the world, and nobody could quite put a finger on him, so everyone left him alone.
Dean was shamefully obsessive about his own stereotype, though. He was a varsity football player, a quarterback. He got straight Cs and flirted with everyone who gave him the time of day and was generally kind of a douche.
But he’s had a rough five years, and he’s grown up a lot.
At the reunion, Dean walked up to Cas and shook his hand. “Castiel Novak, right?”
Cas smiled and shook his hand in turn. “Dean Winchester. How’ve you been?”
“Good,” Dean replied, and added – as Dean learned was par for high school reunions – “Mechanic. I own the body shop down the street.”
“Ah, an entrepreneur. Good on you.” He smiled. “I’m an English teacher. Here, actually.”
Dean and Cas ignored everyone else at the reunion for the rest of the night, becoming both acquainted and somehow reacquainted with one another, then exchanged phone numbers to grab a beer together sometime in the near future.
The near future turned out to be early the next week, when Dean texted Cas and asked if he wanted to meet up with his friends for trivia at the bar down the street. With Cas’s knowledge of totally random academic-type shit, Dean’s knowledge of sports and pop culture, Sam’s knowledge of history, and Garth’s knowledge of… well, nothing, but he provided much-needed comedic relief because the other three took the game way too damn seriously, they won.
They started doing trivia weekly after that, and Dean and Cas sometimes hung out on weekends too. Dean learned that Cas, like Dean, was single. They both lived in shitty apartments. They both had no idea where their lives were headed.
They were on an easy, relaxed path to close friendship, and they were both okay with that.
After three months, they had this routine of texting each other shit they found on the internet on an almost-daily basis, and in general keeping up with each other’s lives. Dean knew enough about Cas that he was anecdotally introduced to all the characters in Cas’s life – his parents, his five brothers and sisters, a few of his best and worst students – so that Cas could mention them by name without an antecedent. Dean was the same way with Cas, but he had much fewer people in his life to recount stories about. He had a lot less drama, but he appreciated being able to keep up with Cas’s. It made life have an interesting flare that Dean hadn’t realized was even missing.
One day, Cas sent Dean a picture text. It was of Cas’s car and what appeared to be a dozen eggs smashed all over it. The text below it read:
C: In your expert opinion, do you believe this incident was caused by:
A) A random suburban thug
B) A vengeful student
C) Gabriel Novak
Dean had replied:
D: Gotta go with C on this one.
Cas’s response was a picture of a note in big scrawled handwriting that read:
Enjoy your breakfast! Love, Gabe
Dean and Cas’s friendship was simple.
Until it wasn’t.
Things started going downhill one night when Dean was bingeing on Netflix and eating an entire pizza. His phone buzzed on the coffee table and Dean groaned because it was just out of reach. After a minute, he put his pizza box on the floor and rolled over to reach for it.
Cas had sent him a picture text.
Of a sexy, naked woman wearing nothing but a lacy, black thong.
The text below it read:
Dean replied, eloquently:
C: Scale of 1-10?
D: 9. Why?
Dean saved a couple pictures on his phone of his favorite porn stars and sent them to Cas in turn.
This new… thing began where some nights they would trade off sending each other porn. Like their friendship, it just seemed like a chill, normal thing for them to do.
Two dudes, sending each other pictures of naked women.
Slowly, pictures turned to videos, and single-word opinions turned into graphic descriptions of what they’d like to do to these women.
D: I’d bend her over the hood of my car and pound into her so hard she’d scream, “Papi! Dios mio!”
It was hilarious. And depraved. And wrong on every level. But it was a blast when they’d do this, just because of how filthy it all was.
And, somehow, comforting.
Also, it always ended with Dean texting one-handed while his other hand was pumping furiously on his cock.
While Dean could only ever think of snappy one-liners to type out, and also because he lacked the patience to text long paragraphs, Cas sent novels of description with his pictures. It was so vivid, Dean would feel like he was right there, watching Cas fuck the curvy redhead bent over with her wrists tied to her ankles.
C: I would shove my tongue down her throat and pull her hair back until she gasped, then I’d lick a stripe up the length of her pale neck and bite down, sucking, until dark purple marks cover that pristine flesh. She would be moaning so loud I would have to shove a ball gag in her mouth, then I would bend her over a table and hog tie her, wrists to ankles, body stretched tight and contorted until her muscles ache. I’d get a flog and slap her ass until it’s red, raw with strips of welts across that perfect round ass. Once she’s groaning and whimpering on her gag, I’d get a vibe and shove it onto her clit, alternating between the vibe and slapping her pussy until it’s soaked, dripping down her legs, and only when she’s sobbing with want would I shove two fingers into her, ramming her g-spot until she squirts all over me. I’d use her cum to prep her ass around three fingers while I shove my dick into her pussy and fuck her until she comes again, sobbing around her gag while I spank her hard on top of her existing welts, leaving hand prints on each cheek. When I’m close and her hole is prepped, I’d bottom out into her ass in one long slide and pump into her, smacking her ass so that she clenches around me over and over and over, then I’d spill my load into her, filling her up so much that when I pull out, it gushes out into her pussy and down her legs.
D: Dude. Holy shit.
C: You’re welcome.
D: I gotta… go clean up now.
Jesus Christ, Dean thought. The orgasm that paragraph and its accompanying picture pulled out of him was intense as fuck.
It suddenly occurred to him that he had been imagining Castiel in all of these positions over the past few weeks they’d been doing this, naked and fucking chicks, over and over and over again.
The horrific result of this realization is this present moment, when Dean is at trivia holding their usual table, and Cas walks into the bar wearing his school clothes: a white button-up dress shirt with sleeves rolled up to his elbows – showing off a full-sleeve tattoo that Dean has never asked about – and a blue tie that’s loosened and backwards hanging on his neck. He has a five o’clock shadow, and his dark blue eyes are tired.
When Cas sits down – acting like he hadn’t given Dean a mind-blowing orgasm the night before – Dean’s dick twitches in his pants, because the hands that are picking up the menu directly in front of him are the same hands that Dean imagined spanking and prepping and fucking the holes of a hot redhead.
His chapped, pink lips are the same lips Dean has inadvertently imagined countless times on the lips of some chick’s pussy, eating her out while she combed her fingers through his hair, making it the perfectly spiky mess it is right now after a long day of running his hands through it in exasperation of his students.
Like a punch to the gut, Dean realizes he wants to run his hands through Cas’s hair too, preferably while Cas is on his knees with those beautiful, plump lips wrapped around Dean’s cock.
And suddenly Dean’s mouth has gone completely dry, and he’s hard as a rock, without having to think of tits or ass or pussy. Just Cas, in his rumpled, business casual attire, with his sex-hair and his DSL and the strong hands that Dean would be willing to bet a lot of money are as skilled and dexterous as he thinks they are.
“Dean? Are you okay?” Cas asks, brow furrowed.
Dean swallows and clears his throat, diverting his eyes and looking at the draft menu. “Yeah. Want to split a pitcher?”
The rest of the night goes smoothly, despite Dean feeling like he’s been kicked in the throat at the realization that he is presently, horribly, painfully attracted to his best friend.
That night, as soon as he gets home from trivia, he decides to push the line a bit further, and he sends Cas a picture of a buff, shirtless dude.
The minutes tick by at an agonizingly slow speed as Cas gets home from trivia too and does all his nightly routine stuff that somehow Dean knows by heart.
Finally, Cas texts back.
C: I bet he doesn’t even lift.
Dean rolls his eyes.
D: Scale of 1-10?
After several minutes, Cas replies:
Cas has only ever given chicks 7 or below. The only porn star who got an 8 was a woman covered in tattoos with a pixie cut who was shoving some chick’s face onto her pussy.
It finally hits Dean:
Cas digs dudes.
D: What would you do to him?
It’s a long time before Cas replies, and Dean’s dick is already hard and leaking in his jeans with anticipation. While he waits, he tears his clothes off and lies on top of his covers in bed, letting the cool early Autumn air of his open window rove over his body.
C: I’d kiss him. Gently, at first. Then I’d pull his lip into my mouth and bite down on it until he whimpers. I’d shove my hand in his pants and wrap my fingers around his cock, pumping him furiously until he leaks all over me, and my palm is slick with his cum. I’d slide my hand down and cup his balls, reaching further back to tease his hole with my slicked-up finger, pressing slowly into it, further and faster, until I’m two knuckles deep and he’s panting into my mouth that I need to fuck him, right now.
Dean grasps the base of his cock to keep from coming.
Then he gets an idea.
D: Do you want to see what you do to me?
The reply is immediate:
Dean goes to the camera app on his phone and takes a picture of his dick, swollen red with a pearl of cum at the top, shiny with his own wetness slicked all over the shaft. He sends it to Cas.
C: Jfc, Dean. You’re huge.
D: Keep going.
Dean closes his eyes and jerks himself loosely, imagining Cas’s hands on him, his fingers in him, giving Dean the intense pleasure that Cas has proven over the history of their friendship that he is more than capable of providing.
C: I’d push him to his knees and unbutton my pants, relieving my cock, half-hard. He would move his hands up to touch me, but I’d swat them away, and instead rub myself on his face, across his lips while he chases me around trying to catch my cock in his mouth. Fully hard, I’d leave a stripe of cum across his cheek and bottom lip, then press myself into his mouth and shove all the way down his throat until he’s swallowing around me, eyes watering. I’d fuck his face until I’m close and then I’d pull out and make him stand up, licking the taste of myself off of his lips. Then I’d lay him down and lube up my fingers, prepping him so slowly that he begs me for a third, and then for my dick inside of him. When he’s ready, I’d line my cock up with his ass and press in, bottoming out slowly, and he’d scream for me to fuck into him, harder and faster, until I’m slapping into him, onto his sweet spot so hard that he comes all over his own chest and, with his orgasm clenching his hole around my cock, I’d come inside him, hard, screaming your name.
Dean comes with a shout while barely touching himself.
Screaming your name, Dean reads again.
Panting and unable to use his hands to type out a coherent message, he takes a picture of his dick, waning hardness, resting against his abdomen and the fuck-ton of spunk all over his stomach, chest, and neck.
He sends it to Cas, and passes out.