Someone already recc'd Needed but I feel the need to say how much I also love that friggin' story. Ahem. Brother Mine has also already been recc'd as well, but that's a good one. I do have this one, which is not exactly what you specified but I have a suspicion you would like it:

* A Friend Given By Nature (http://mollrach13.livejournal.com/9363.html): Adam's mom is killed, and the only contactable family number is Sam. First shocked, but accepting, Sam takes on the role as older brother and caretaker with pride and worms his way into Adam's heart. But going to school, to work, and making enough money to support two people is hard to do and after a while, he works himself into a fever big enough to warrant a hospital visit.

If you are okay with complete AU universes, there's also:

* There's No Easy Way to Live Free (http://archiveofourown.org/works/1441864): When a young man shows up at the garage claiming he’s John Winchester’s son, he’s just in time to get entangled in the Wayward Sons Motorcycle Club’s latest attempts to stay afloat while their president’s in jail on arms trafficking charges. No one’s sure about the direction the club might be forced to move in, but Dean knows he would feel a lot better about it if he trusted the girl who put the idea into Sam’s head and if Cas weren't being even more cagey than normal. Being Sergeant at Arms was easier when he didn't have to keep everyone calm about the fact that they were working with their rival club’s boss and that’d be easier if he was calm about it. Personal lives and work get tangled together and it's hard to decide which one is more dangerous, even if only one has bullets.

As far as disappointment fics, this will probably fit the bill pretty nicely, as both of the Js parents are, well, yeah....

* One Kiss at a Time (and timestamp) (http://archiveofourown.org/series/152768): Jensen, Jared's newest employee at Jay's Pad, has had a hard decade. Recently released from a rehab facility, Jensen's living at a shelter and just needs some help getting his life back on track, and Jared vows to be the one to do just that. Jensen is also an amazing guy and Jared finds himself falling hard after just a week, and he's delighted to find out that Jensen feels the same way. But Jensen still has demons he's fighting and secrets he's keeping and Jared knows that a relationship is the last thing Jensen needs right now. But his heart isn't listening, and when Jared's involved in a stomach churning ordeal, it brings up things from Jensen's past that are revealed to be the causes of all his problems. And Jared doesn't know if he can fix them all.

And also

* Disintegration (series, current story WIP but updating regularly) (http://archiveofourown.org/series/61120): This series explores the deterioration of the family ties within the Winchester family between Sam's departure for Stanford and the series pilot. An attempt is made to explore the lives of all three Winchesters, exploring the reasons for the changes that take place in familial relationships over this three and a half year period. (Note: Sam is pretty damn BAMF in this, John is an asshole who can't see anything good in what Sam does, and Dean is John's little soldier. I love the portrayal of Sam in this, but some Dean fans may not like it; he's not evil, just too busy following John's orders to think for himself too much of the time. However, it totally matches the multiple points for disappointment.)

Edited 2015-05-04 04:47 pm (UTC)

Thank you so much!! 💛 YAY this will keep me happy for a while😊

I love all your recs!
I just had to add: If you like BAMF!Sam with serious self-esteem issues, asshole!John, and not-really-thinking-things-through Dean, Safiyabat (http://safiyabat.livejournal.com) is your girl. She's the author of the Disintegration series.

Thank you! I'll check it out😊

I do love her stuff! Sometimes she's a little too Dean negative for me, but her BAMF Sam really is fantastic, right behind Jassy's Regrets (http://samdean.archive.nu/series.php?seriesid=95) trilogy, which is probably my favorite BAMF!angsty!Sam.