So hard to choose what to rec for my first rec post here. I was all, must include this, and there are these crossovers, and that's my favourite story of all time, oh, and this one too... But I was brutal, and limited myself to four five six, and went with het recs, as we haven't had any of those yet.
One thing I'll say before going onto the stories - you might want to give these a try even if you're a bit ambivalent about het. The first two and the fourth in particular could easily be canon, one is really Sam and Dean, though Dean is Sam's older sister Dee, and they're all just gorgeous stories independant of the pairing or genre.
leaving louisiana in the broad daylight by
traveller (pre-series, Dean/OFC, PG-13, 1,667 words)
Dean in New Orleans, just prior to fetching Sam from Stanford. A story about wanting, and what you'll do for what you want, without thinking about the consequences. It's a story with a sting, and it's told in
traveller's amazing prose that somehow manages to be both rich and spare.
When by Now and Tree by Leaf (She Laughed His Joy, She Cried His Grief) by
pyrebi (Stanford era, Sam/Jess, PG-13, 6,041 words)
This, I think, was the story that made me feel I knew Jess. It's a gorgeous, happy story, Jess and Sam meeting and falling in love, except that we know what has to happen and I swear it hurts worse reading this than in the pilot, because this time I love Jess too.
isis on the fifth day by
appletarts (AU genderfuck, incest, Dee/Sam, Dee/f, R, 3,245 words)
I've read this story probably more times than any other story. It's raw and vivid and visceral, it doesn't flinch away from the realities of incest and sex and their youth.
Sam's Watched Porn Before by
femmenerd (Stanford, Sam/OFC, NC-17, 1,024 words)
I'm trying to think what to say about this that wouldn't be serious TMI. I'll just say it's really, really hot! Yeah.
Black Days by
mayatawi (post 2x05, Dean/Ellen, NC-17, 2,030 words)
This isn't a pairing I can get behind, but if it did happen, this is a way I could believe in. Ellen's a tough woman, and Dean's in way over his head with her.
and my heart the shape of a begging bowl by
flipmontigirl (early season 2, Sam/Ellen, NC-17, 3,613 words)
Now this is a pairing I absolutely adore, and this is the story that made me fall for them. Sadly, I haven't got either time, or words good enough to say how much I love this story.