I am so your girl for this.

Here There Be Tygers (http://kalliel.livejournal.com/206457.html)by kalliel: "The problem with Dean's memory is, it means he asks that question about eight trillion times more ("Sammy, are you okay? well, are you?") and as far as Sam's concerned, the answer matters even less. The problem with Dean's life is, it's supposed to end this year. And the problem with Dean's brother, well. Sam's still working on that one." (gen; I'm reccing this one all over the place today)

The Firefly That Loved Metallica (http://fleshflutter.livejournal.com/3749.html) by fleshflutter: "In which Sam has a bottle full of soul." (Sam/Dean)

The Descent of Inanna (http://vaingirlfic.livejournal.com/32303.html) by vaingirlfic: "Sam gets Dean out of his deal by making a worse one. It's like kidfic in a way." (Sam/Dean, lots of warnings and mindfuckery, and one of my very very favorites)

We Came From the Breeze (http://lazy-daze.livejournal.com/486002.html?format=light) by lazy_daze: "Have some post-hell amnesia fic!" (Sam/Dean)

Three Days on the Rack (http://archiveofourown.org/works/221235) by keerawa and reena_jenkins: "It’s been months, but Sam finally found a crossroads demon willing to Deal to get Dean’s soul out of Hell. The Deal sounded too good to be true. Sam took it anyway." (Sam/Dean, potential triggers out the wazoo)

The Year of Letting Go (http://runedgirl.livejournal.com/32053.html) by runedgirl: "A hunt gone wrong leaves Dean Winchester barely alive, and helpless for the first time in his life. Can Dean let go of his need to be the big brother and let Sam help him heal, or will the complicated feelings both brothers have been hiding from each other pull them further apart than ever? As Dean’s deal comes due, both Sam and Dean will have to let go of their fears, or face losing each other forever." (Sam/Dean)

Regrets Trilogy (http://samdean.archive.nu/series.php?seriesid=95) by jassy: "Sam refuses to allow the Crossroads Demon to have his brother." (Sam/Dean)

One Moment of Knowing That (http://kroki-refur.livejournal.com/174637.html) by kroki_refur: "As Obelix would say, if you're off your food, you're ill. Of course, he never met the Winchesters." (gen)

I don't know how you feel about fanvids, but The Other Side (http://archiveofourown.org/works/838289/chapters/1597321) by astolat is unlike any fanvid I've ever seen: "A hunt for a dragon in New York City ends with some unexpected changes for Sam and Dean. With the clock ticking down on Dean's deal, can the brothers pull together to save the city?" (The movie is gen, and there's a follow-up fic called Mystery Dance (http://archiveofourown.org/works/989550) by balder12 that is Sam/Dean and wonderful)

Life as We Know It (http://sevenfists.livejournal.com/113120.html) by sevenfists (and follow-up fic, The Taste of Apples (http://archiveofourown.org/works/283711) by rosekay) is a AU domestic fic where Sam saved Dean, though the focus is much more on the domesticity and the growing wincestuous tension than on the specifics of what went down. (Sam/Dean)

Keep Our Minds on the Sum of Each Other (http://lazy-daze.livejournal.com/452858.html?format=light) by lazy_daze is a Sam/Dean bodyswap fic where Sam talked Dean's way out of Hell. :)

Death Like Dying (http://archiveofourown.org/works/189790) by sobrecogimiento: "After Sam gets Dean out of hell, Dean doens't remember anything except Sam. And that means anything. So Sam has bundles of fucking joy trying to deal with it." (Sam/Dean)

Crush (http://sonofabiscuit77.livejournal.com/18531.html) by sonofabiscuit77: "Five years after the apocalypse didn’t happen and Sam and Dean have settled down, or as much as the Winchesters can ever settle down. Sam is a college professor and Dean a well-respected small business owner and they’re learning how to balance work, hunting and dog-ownership while coping with the metaphorical and literal scars of war. Life’s not perfect, not for a (sort of) out and proud couple in small town USA with a lot to hide, but they’re dealing, that is, until Dean employs one sexually-confused teenager who develops an unhealthy obsession with both of them... Switching between five years earlier and now, we learn how the boys came together, how they made it through the big fight and whether they’ll ever manage to find that flighty temptress, happily ever after." (Sam/Dean; to be completely honest, I'm not 100% sure whether Sam saves Dean here or Castiel does, but either way Sam's a huge part of the processes and sacrifices plenty along the way)

And the ending is ambiguous in this one, but it's wonderful anyway - Route 66 (http://spn-heraea.livejournal.com/3846.html) by sevenfists (Sam/Dean).

And a couple crossovers - Defect (http://www.fanfic.otherplaces.net/defect.htm) by kikkimax (gen; SPN/Criminal Minds) and Old Country (http://archiveofourown.org/works/164479) by astolat (Sam/Dean, SPN/Harry Potter)

Hell yes. I have a tag (https://delicious.com/acqiel/th%3ASam.saves.Dean.from.Hell)solely dedicated to fics with this trope. But my reccommendations:

Sam breaks the deal and saves Dean:

Until the End of the World (http://geminigrl11.livejournal.com/10599.html) by geminigrl11
He finally gets a look at his brother and Sam is...Sam is laughing. Pained, raw, gulping laughter that's verging on hysteria. Dean can't get his head around it. "What did you do?"

Small Clause Out (https://www.fanfiction.net/s/4164320/1/Small-Clause-Out) by authoressnebula
There's a way out of the deal, one that'll have Dean back at Sam's side. Problem is, it isn't going to really be the same; not with Sam now the oldest between them.

I'll Keep You Safe Inside Me (http://flawedamythyst.livejournal.com/223183.html) by flawedamythyst
So, the thing is, there really is no way to break a deal with a demon without consequences that even Sam isn't willing to consider. Sam has had to accept that and move on, looking at new areas of research, about souls and hell and the way demons get one into the other. It isn't until the fourteenth time that he reads 'demons can't touch a soul while it still has a body protecting it' that he really understands what it means.

I Am the Very Model (http://vorpalblades.livejournal.com/63183.html) by vorpalblades
Jake killed Sam, but Sam came back. Sam killed Jake, and Jake stayed dead. That means Sam won, and to the victor goes the spoils, right? Yeah, that’s what the rest of Hell thought too.

weathercock snowfall (starlight cockcrow) (http://kroki-refur.livejournal.com/217733.html) by kroki_refur
Dean's got three weeks to live, and Sam's acting like a freakin asshole. And hey, it's not like that's never happened before, but this is a little too much like history repeating for Dean's liking.

Sam pulls Dean out of Hell:

and death is no parenthesis (http://ficviendha.livejournal.com/96853.html) by minviendha
Prompt: Between S3 and S4. Sam decides he's going to get Dean out come hell or high water, so he opens the Devil's Gate (Colt, C4, whatever) and marches right in. Describe the trials and tribulations he endures on the way to find Dean and on the way out with Dean.

I'd Gladly Lose Me To Find You (http://flawedamythyst.livejournal.com/366852.html) by flawedamythyst
Sam takes a vow of silence in order to pull Dean out of Hell, but by the time Dean comes back, Sam's lost more of himself than just his voice.

Highway to the Grave (http://chase-acow.livejournal.com/182028.html) by chase-acow
The unfortunate fact that Sam found to be true, was that you could never find a hellhound when you needed one.


Now excuse me while I go read all the other recs I haven't come across yet. :)

Edited 2015-06-30 12:39 am (UTC)

This is my favorite Sam saves Dean fic: it's funnier than all get out. 'Do Not Pass Go' by insomnia_geek. Summary: It wasn't as if Sam expected it to work. Even the most ironclad contract can have hidden escape clauses, exploitable with proper documentation.

http://insomnia-geek.livejournal.com/3931.html

Of course, I can't find the links when I need them, but I love these two.

"No Stop Signs or Speed Limits" -- Sam breaks Dean out -- with the help of a friend.

"The Devil and Samuel Winchester" -- they wait together at a church for the crossroads demon-- but something goes sideways.

This one is for Sam pulling Dean out of hell:
What He Was Taught (https://www.fanfiction.net/s/4262213/1/What-He-Was-Taught) by authoressnebula
Summary: Sam was taught not to give up, and that family means everything.
It's also part of a series, if you want more:
Where He Was Changed (https://www.fanfiction.net/s/4274164/1/Where-He-Was-Changed)
How He Was Loved (https://www.fanfiction.net/s/4276332/1/How-He-Was-Loved)
When He Was Strong (https://www.fanfiction.net/s/4389953/1/When-He-Was-Strong)
Why He Was Shaken (https://www.fanfiction.net/s/4747020/1/Why-He-Was-Shaken)


This one is Sam saving Dean from going to hell:
Everyone Plays (https://www.fanfiction.net/s/4289594/1/Everyone-Plays) by authoressnebula
Summary: "Sam finally stopped in the middle of the dirt road, tears streaming down his face as the Impala and Dean disappeared into the night." Sam offers a plan; Dean's far from interested, but the crossroads demon is.

Free and Clear (http://archiveofourown.org/works/4207?view_adult=true) by molly
Summary: "You don't even know what you're thanking me for."

One King And A Colt (https://archiveofourown.org/works/178392?view_adult=true) by apetslife
Summary: A followup to the S2 finale. They spend the first few days after killing the demon with Bobby, resting up. He'd taken one look at the both of them, said something gruff about the "walking dead" (which wasn't as funny as it should have been), and dragged both of them back to his place. (I realize this says season 2, but read it anyway because it's excellent.)

Everything, After (http://destina.livejournal.com/450592.html) by destina
Summary: Everything's different, after.

pick a star on the dark horizon (and follow the light) (http://javajunkie13.livejournal.com/61839.html) by javajunkie13
Summary: One month, and it's still a little overwhelming to have Dean back, still a little unbelievable.

The World's A Small Child in the Dark (http://archiveofourown.org/works/695472?view_adult=true) by stele3
Summary: Post-AHBL II. Dean made his deal: he's got a year. This is that year.

Threefold Path to Redemption 'Verse (http://rei-c.livejournal.com/tag/threefoldpath) by rei_c
Summary: Sam finds a way to keep Dean from going to hell: he'll go in his brother's place. He knows it's going to be bad and that he'll emerge changed. He never knew how much. (First, this is a dark fic. So be warned. The main fic is listed towards the bottom of the page; scroll past the prequels to find it.)

These 2 are humorous:
An Undreamt Thing (http://setissma.livejournal.com/540427.html) by setissma
Set post-season 2, as Sam's working to get Dean out his deal. Dean discovers he can overhear other peoples' thoughts. Very funny.

Dimensions and Verticals (http://archiveofourown.org/works/288486) by bellatemple
Summary: Sam accidentally gets Dean out of Hell. The results are something no one could have expected. . . .

Edited 2015-06-30 10:32 am (UTC)

Eight Arms are Better than Two --right? (http://fannishliss.livejournal.com/184584.html) by fannishliss
Length: 899 words

Sam, in s3, considered saving Dean from Hell by making him immortal through creepy super science. In this story, the result is that Dean is an Octopus.

Notes: I can't even fucking believe how cute this is.


Defect (http://www.fanfic.otherplaces.net/defect.htm) by kikkimax
Crossover: Criminal Minds
This fic is too good to miss. I might've read it before I started watching CM, but I'm not sure. For maximum enjoyment, consider watching a few episodes of Criminal Minds and coming back if you've never seen it. Episodes 1, 2, and 14 of season 1, and episodes 17 and 21 of season 2 is a pretty good pool to pick from.
Length: 39,686 words

Dean is finally captured by the FBI just as his time runs out.

Notes: My #1 favorite fic. Sam and Dean both are written wonderfully. The first half of this fic is mainly Dean vs. FBI, but then it gets into the lengths Sam is willing to go through to save his brother. It was a pret-tay cool operation imo. Kikki's depiction of Gideon is beyond flawless. I've never seen characterization this good anywhere else. It's done with such care in every aspect- from Gideon's at times insensitive working manner to his near-limitless compassion in situations few others would be able to stomach- that I dare to say it has a purity of character the show usually lacks.

And Lord, is this fic sad. It has a happy ending- and two sequels- but...

Edited 2015-06-30 08:14 pm (UTC)

Wow, thanks everybody so much for all the suggestions. They're highly appreciated. I guess I have a lot to read!!