Pairing: Sam/Dean, Sam/Jess, Sam/OCs
Summary: Sam's always had a weird relationship with sex.
Notes/Acknowledgments: Unbetad. For the prompt do it til you fall down for salt_burn_porn. Title is a shout-out to Chasing Amy.
The first time Sam had sex ended with a trip to the hospital, because Dean is right and virgins should never ever try to have sex with other virgins. Or, maybe that's the first time he tried to have sex. He's still kind of unclear as to whether that counts as sex or not since they didn't actually manage to do... much of anything.
No one actually got hurt hurt. Well, there was pain, but there weren't any stitches needed or anything. The emotional pain is something Sam will never forget though, because it led to the most awkward version of the talk he has ever been forced to experience. No one should ever be forced to hear John Winchester talk about "proper lubrication." Especially since he actually said it like that, and Sam realized Pastor Jim probably wrote him a script to read.
That was pretty much the most embarrassing moment of Sam's life right there. Until the next time he attempted to have sex.
She gave him points for enthusiasm, which were every bit as condescending and horrible as they sounded, and then told everyone in the school that he couldn't get it out of his pants. Dean laughed at him all the way up until he got them run out of town for banging the sheriff's daughter.
"What the hell, Dean? What possible reason could you have to fuck her on a firetruck?"
"Shut up and keep packing."
It's not like something bad happens every time he has sex. Just, you know. Most of the time. Nothing bad enough to make him considering stopping it seriously, of course. A small skull fracture, a few torqued fingers, a dislocated ankle, things like that. One time he dislocated his shoulder taking off his shirt—which is not as bad as it sounds because trick shoulders mean the arm will just kind of slide in and out of the socket randomly. That doesn't count anyway because the shriek of terror from... that one girl, was like ice water to the crotch.
But then she went psycho a week later and tried to stab him to death with a bowie knife. So Sam forcibly blocked her name from his memory. In hindsight, she was probably a demon, but back then he thought he just had the fucking worst taste in people on the planet. Apparently he was underestimating.
That all changed with Jess, though. The bad taste, that is. Not the injuries. They both went from four foot nothing to six feet in the span of about a day and a half when puberty hit them, and for all the grace Jess had with a paintbrush she was a flailing newborn giraffe the rest of the time.
She was smart, and gorgeous, and nice, and had absolutely no problem telling him exactly how far he had his head up his own ass. She also, apparently, had a logic chip in her brain that was just as faulty as Dean's was, because while a sane person might want to keep the details of embarrassing sex to themselves, Jess liked to tell them to her mom and her cousins and her grandmother.
The night they celebrated their three month anniversary, for example, was a fond memory her mother used to torture Sam with over Thanksgiving dinner. Given, Sam had only experienced Thanksgiving with other families twice before, but he was pretty sure that wasn't how it was supposed to go.
The anniversary started out amazing. Sam saved up money, and took Jess out to her favorite restaurant, and didn't worry all night about homework or if he had done the math right on the money in his account. She had lobster and made fun of the face Sam made when she cracked the tail, and Sam even splurged and got desert.
Later that night they had gone back to her apartment, because his had three other guys living in it. They made it to the living room; with Jess's dress flung somewhere near the kitchen and Sam's mouth working over that spot on her neck that always made her dig her nails into his back. He bit her, just a small nip with the barest hint of teeth, and Jess moaned and then apparently curled her legs up.
"Apparently" because all Sam knew was a sudden sharp pressure in the back of his knee and then pain, pain, pain. Pain when his knee gave up and gave out on him, pain when Jess's forehead bounced off of his, and pain worse than that time Dean hauled off and kicked him in the nuts so hard Sam was sure his balls were going to be actually missing when he took off his pants.
Because Sam is Sam. And, so, when Jess's heel decided to kiss the back of Sam's knee, he was still inside of her. And when she fell, painfully and heavily on top of him, that didn't change. It was this sudden bloom of pain that Sam could not put into words, and he actually blacked out for a small portion of time.
The rest of their anniversary was spent in the emergency room, with a zip-loc bag of ice wrapped in a towel, and a hoodie pulled down low over his face. He ended up with a knee immobilizer and a deep and abiding love for every single nurse there, not one of who so much as batted an eye at him. And the most awkward Thanksgiving ever, of course.
Jess used to tease him. Because while he could do slow and patient sex, most of the time he approached it like a challenge, or a fight. Something to conquer before it knocked him unconscious and took his wallet. Which may have possibly not helped with the whole thing where if sex could be anthropomorphized it would clearly want him in various levels of pain at all times.
Dean has never had a sexual encounter he has kept to himself, or a sexual experience, if Sam's unusually formative years were anything to go by. He always told Sam sex should be fun. It can be dirty, or secret or whatever, but if you're spending the whole time "mad at the universe because you literally can't tell her elbow from her asshole, then you don't deserve to have sex."
Sam never really understood what that meant. Half of what Dean says is just shit to annoy Sam anyway, but in hindsight, Dean maybe had a point there.
After Jess, Sam doesn't want fun. Not for a long time. When he finally does, it's with Madison, who reminds him so much of Jess that it makes him love her a little, even knowing that that's a stupid thing only a twelve-year-old would think after knowing her less than a week.
Then it was Dean. Dean, who he spent more of his life than he would care to admit specifically trying not to think about. Dean, who sold his soul for Sam, who was gleefully going to hell and didn't seem to care at all, so long as Sam was still topside to keep existing with the rest of his heart ripped out.
It wasn't fun. It was desperate, and sad, and painful. It was Sam finally admitting that he had failed, wasn't as good or as smart as they thought he was, and that short of a miracle, Sam was going to be the last Winchester alive in less than twenty-four hours.
After that, Sam spiraled. There was nothing but Ruby and too many varieties of pain and hurt and injuries to even begin to try to account for, and then nothing, and then nothing and no one that matters for a very long time.
Then it's Dean again. Dean who is not dead, who does not hate Sam, even though he has every right to. He pins Sam's wrists to the bed so Sam doesn't smash them behind the headboard, and blocks the knee Sam accidentally sends towards his kidneys when Dean grazes a ticklish spot.
He's in Dean's lap, riding him. Dean's got a hand wrapped around his cock, jerking him off, and the other at the back of his neck, guiding his head for a better angle to kiss at. And then Castiel, who has still yet to ever begin to even comprehend boundaries, is suddenly right next to the bed and talking to them.
The physical pain is minimal, either he bit his own tongue or Dean did, but Sam may never recover from the mortification caused by coming all over his brother in front of an angel, even if that angel is Castiel.
All in all, it could be worse. It beats having his dick bent.