by zation
~ 6k
It’s senior prom and Dean has his eyes set on his graduation price. Rhonda has the best plan ever to help her friend and there’s no reason it won’t work out because who doesn’t have sex on prom night, right?
Or,
The one where (spoiler) Dean totally has sex on prom night.
by brokentoy
~ 40k
It starts when they're sixteen: Dean is flunking his classes and Castiel is his strangely persistent tutor. They grow into best friends, and now that they're adults (or at least they're supposed to be) into best friends with benefits. They agree: no strings attached, no feelings to complicate the fantastic sex. Things are supposed to be simple, and yet they aren't.
by Unforth
~ 41k
With an over-sensitive sense of smell, omega Dean Winchester finds the scent of most potential mates to be, frankly, nauseating. Enter alpha Castiel, who smells fracken *perfect* but has problems of his own.
by ozonecologne
~ 3500
Prompt fill: a/b/o. When I think Omega I think Dean Smith. Sorry but them’s the breaks.
Basically 3.5k of Dean Smith giving Endverse!Cas road head in a taxi cab.
by Angrysouffle
~ 10k
Dean is a shy lifeguard who catches a swimmer skinny dipping on his watch. Castiel is a paramedic with a stressful job, a painful past and a penchant for public masturbation and sex in inappropriate places.
by Dangerousnotbroken
~ 9k
Dean's best friend lives just shy of 3000 miles away, and they've never been in the same room. That hasn't stopped Dean from falling stupidly in love, though.
by cagdignan, Guu
~ 81k
Castiel spends the first two weeks of college in much the same way he spent the previous years: alone with his books. He’s fine with it—he enrolled in college to learn, after all. Then in his first chemistry lab, he has the bad luck of being paired with snide, good-for-nothing Ruby, and the further misfortune of sitting behind Dean Winchester, the world’s most beautiful distraction. Ruby catches Castiel staring at Dean and makes him an offer.
by ballsdeepinwinchesters
~ 149k
Dean and Castiel's relationship has evolved over time- from strangers to roommates, roommates to friends, friends to best friends, and from best friends to "We're just friends."
Previously "It Happened One Night (And A Few Times After That)"
by KiwiChick42
~ 108k
Castiel thought it was teenage hormones... it wasn't. He couldn't have been more wrong. Evolution was once again molding the human race, whether it was ready for it, or not.
by zation
~ 119k
When Lisa and Dean break up Dean finds himself devastated. Not surprisingly, he doesn’t handle the situation very well and ends up kind of accidentally hiring a prostitute. Only, Castiel isn’t really what Dean had expected and he finds himself coming back again and again. And Castiel in turn finds himself powerless to stop him.
Or,
The one where Dean falls in love with a whore and Cas tries desperately to prevent it.
by Ivy_Brooks
~ 1700
Prompt fill: "Dean's stuck on a packed subway car. The guy behind him is pushed right up against him, his groin to Dean's ass, and it's hitting just right. The rocking of the car is causing them to rub together, and it's really starting to turn Dean on."
~ 11k
by sharkfish (waitforspring)
Oh god. By the time Dean is visualizing, compulsively, the last good fuck he had, he knows that he’s made a mistake. Within the next mile of walking, he can’t even delude himself into ignoring it anymore; he can feel a trickle of moisture running down the inside of his thigh. Oh god.
Castiel has had plenty of time to get used to the idiosyncrasies of his symptoms, but the way his focus shifts towards this particular scent that reaches him on the barest breeze -- it’s somehow different.
And somehow he knows, automatically, that it’s not happy-heat-mate but scared and sick and alone.
by justkeeponwriting
~ 50k
“Three days, Cas,” Dean groaned. “You’re not going to call her tomorrow and scare her off, like you always do! Or worse, tonight! That has ‘creeper’ written all over it.”
Or, the one where Dean pretends to be a woman who likes to text Cas in order to teach him a lesson, and finds that he’s way in over his head. (Inspired by How I Met Your Mother's episode 4x21, "The Three Days Rule".)
by Jo_Winchest1967
~ 54k
Dean is very unsatisfied with his sex life. His best friend and roommate, Castiel, suggests he try out BDSM. Castiel has been in the world of BDSM for years as a Dom. Dean agrees and as they go over the list of possible Doms, it becomes clear that the most realistic choice is Castiel himself. Dean harbored a rather large crush on Cas while they were in college, but he still agrees not to let feelings get involved. He soon realizes how hard it is to keep old feelings in check.
by 6or3dom
~ 169k
The bed is their home.
The bed is there the night that Dean pulls Castiel into his room. The bed is there when Dean weeps in it over the course of four years, when Dean wonders where the angel had gone after the Darkness had taken over. The bed is there the night that Castiel returns to Dean after having been missing for four years. The bed is there when Dean tells Sam that Castiel has lost all of his memories after Rowena's curse, that Castiel simply doesn't know who Dean is anymore.
It is in the bed where Dean and Castiel lie, slowly weaving their relationship together, first the wrong way and then the right way. It is in the bed where Dean pines for Castiel and wishes for the angel's memories to come back. It is in the bed where Castiel slowly falls in love with the man that he can't remember.
It is in the bed where they press their bodies together, press their lips together for soft kisses on their pretend wedding night. It is in the bed where Dean asks Castiel to touch him and Castiel obliges and they hold hands and move in rhythm with each other.
Everything changes when they share the bed.
by Winglesss
~ 70k
On his way home from work Dean meets a young prostitute and decides that he can’t leave the boy sleep on the street in a pouring rain.
by zation
~ 5500
When Castiel suddenly starts receiving notes of a particular kind he at first treats it as a joke because high school right? Only, the notes don’t stop and Castiel finds he can’t ignore their pull for much longer.
Or,
The one where Cas has a secret admirer.
by Unforth
~ 152k
Regency Era-esque AU. Dean Winchester has built the life expected of him, marrying Charlotte Bradbury, raising a family, maintaining his estate, spending winters in ton. However, their life together is built on a shared lie - they are best friends, united to protect the secret of their true desires. Charlie has found a companion who shares her preferences, but Dean is lonely for a want of partner. That is, until he learns of Ms. Naomi's exclusive, monthly, male-only parties, and manages to secure himself an invitation...
by Kaemem
~ 4500
Dean likes wearing buttplugs and when he arrives at the airport he realizes he should've thought about this one a little sooner.