Accidental Documentaries by Tassos
"As Class Historian, Antonia is determined to make the best high school documentary her senior year that anyone has ever seen, but the first few weeks of school bring more to light than she ever expected when a freshman girl goes missing, the new kid Dean takes an interest, and old traumas may be the key to the present." Outside POV requires that the author sell you one hell of an OC, and Tassos delivers brilliantly. Antonia is real and realistic, and the story works its way through two weeks in her life in riveting style. Welcome back to high school. Pre-series.
Accidents Will Happen by holli
Some Goth teenagers accidentally resurrect John Winchester. No, seriously. A first-person original character POV, which has absolutely no business working, yet does. Funny and awesome in the 'watching a train wreck' sense; 16-year-old Leah's view of the Winchester boys is just too hilarious. Read immediately, even if you don't watch Supernatural.
Communication by Rusalka
A post-ep for "Asylum" with a gorgeous Dean voice, not reflecting on all the things the boys don't talk about.
credu ut intelligam by fryadvocate
"If Dean was a noun, he would be a Latin noun, he would shuttle off each part of himself into a different ending, so that when he smiled a certain way he would mean one thing and when he lied to people it would be ok because the other four declinations of him weren't liars at all." Gorgeous, gorgeous Dean, struggling to teach himself a dead language because it means so much more to his life. It sounds really simple, but it's layered and complex and captures Dean just beautifully. You must read this.
Don't Look Back by cupiscent
A beautiful extrapolation of a one-shot character; Seri (the little girl from Home) rings perfectly true 6 years later, as do the reactions of the people around her when things continue to go bump in the night. It's rare to find OCs that fit so beautifully into a canon universe, but this is very well done.
Family Comes First by ethrosdemon
A cool future-possible, with Dean's son and Sam and Dean, and how life goes on. The ending is a little abrupt (and goes immediately into ranty author's notes, so be careful), but the story is just awesome, with two truly lovely OCs.
A Foreign Country by casspeach
Dean finds himself alone and badly injured on the side of a mountain in Colorado with no memory of who he is or what heís doing there. An amnesia story with an OFC who gets involved with Dean. Shouldn't work, right? SO WRONG. It totally works and is entirely excellent! Go read!! KikiRec
Hard Rain's Gonna Fall by ErinRua
A haunting in Pennsylvania turns ugly, and Sam and Dean must deal with hazards both supernatural and secular. ErinRua incorporates Civil War history in a very cool way, and she captures both of the boys perfectly. A must-read.
Killing Time in Detention by Troll Princess
And along the same lines, Sam and Dean pass notes in detention; it's all fun and games until the shop teacher tries to eat you.
my life's come off its tracks by mimblexwimble
A wee!Chesters AU; young Dean falls seriously ill and the consequences will last forever. Really, really well-done. KikiRec
Night Moves by researchgrrrl
Seriously, totally hot Dean smut, with the sexy and the glitter and the funny and the... wow. Yeah. < fanning self > Take one really messy hunt, a rescued girl who's no damsel, thank you, and Dean. Mix well and enjoy. An incredible OC takes this from the level of everyday smut to masterful smut, beautifully conceived and executed. And did I mention with the hot? NC-17
Red by Big_Pink
Rich, detailed, terrifying, and pulling no punches; when you figure out what the title is referring to, your jaw will drop. One of the best Supernatural stories out there, set mainly in a Washington State logging camp, and featuring gorgeously characterized Sam and Dean, many awesome OCs and a monster that will haunt you as thoroughly as it haunts Dean. Incredibly well done; this will totally blow you away. (For an equally good, and far more hilarious, time, try Abracapocus.)s
Sneeze Three Times by dotfic
A very neat pre-series story about baby Sam and Dean and a heffalump hunt. A nice look at the family dynamic of John and the boys.
A Stand-Up Man by Alethia
Roadtripping with your brother, on a mission to kill evil beings, without killing each other -- some times are harder for Sam than others. Snarky and hilarious, a freewheeling ride in the Metallicar eavesdropping on the Winchester boys, and a gorgeous view of Dean through Sam's eyes.
There'll Be Peace when You Are Done by lyra_wing
Why Dean hates fortune cookies -- it's a weird premise for a story, but the reason works heartbreakingly well. Short, but definitely not sweet.
Tradition! by bellatemple
Oh, you actually expected the Winchesters to have normal Christmas traditions? Yeah, not so much with that.
Twelve Times Dad Threatened to Turn The Car Around (And Three Times Dean Almost Rode In The Trunk) by clex-monkie89
If you've never felt sorry for John Winchester, consider 18 years of car trips with two boys. Often funny, often sad; there are a few grammatical issues but not enough to take away from the coolness of it all.
Under a Haystack by Emily Brunson
Holy crap. Kidfic, yes, but deadly serious kidfic: Dean gets reverted to age 7 by a curse, and by that I mean he is Dean when he was 7 -- training to hunt and wanting his daddy. And Sam finds himself responsible for a child, suddenly living his father's life. Sam's voice is pitch-perfect and babyDean will leave you on the floor in tears. Fabulous.
Walk Like a Man by hkath
Dean gets cursed to the mental age of 10, but it takes Sam a while to notice. < snerk > It all kind of snowballs from there: the virgins, the breading, the space ninjas.... KikiRec
weathercock snowfall (starlight cockcrow) by kroki_refur
To quite marinarusalka: "Three weeks before Dean's deal comes due, Sam stops talking -- just as he had done once before, pre-Stanford." A darker, twisted fairy-tale kind of story.