"Chink in the Armor" is amazing. It's by BlueSea14 and it is on fanfiction.net. It's is pretty much exactly what you are looking for. I don't know if Sam feels guilty, but he freaks out and goes all out to help him.

Summary: Dean Winchester, in the years following Sam's departure for college, was not a very stable individual. Warnings: self-harm, drugs, alcoholism. OneShot.

[url]http://www.fanfiction.net/s/4207347/1/Chink_in_the_Armor[/url]


I know I did the url thing wrong, but it still works! I need to learn how to do that properly. :(



This somewhat fits your description. It's set after All Hell Breaks Loose, Part 2. Dean can't sleep. It's called "Remember This" by Onari. It has a paranoid Dean and this story makes me wish that there were more All Hell Breaks Loose P2 codas.

Summary Dean looked exhausted all day. Dark circles appeared under his eyes, and he needed three times more coffee to keep functioning. He happened to be awake whenever Sam was asleep. But if he was also awake when Sam was awake, when did Dean actually sleep at all? Spoilers for AHBL I/II


[url]http://www.fanfiction.net/s/3726924/1/[/url]




There is another one on ff.net called "Head Rush" by SaintDogStreet. I know you asked for Dean fics, and I usually love Dean fics more than Sam ones since Dean is so fascinating, but this one focuses on Sam falling apart after Dean goes to hell. It's amazing.

Summary: Four months without Dean. Hell on Earth. A look at one night in the life of Sam Winchester as he steadily falls apart. Limp!Sam and BigBrother!Dean. Set sometime after No Rest for the Wicked, before Ruby came and worked her magic on Sam. Oneshot.

[url]http://www.fanfiction.net/s/5129618/1/[/url]


I love fics where one of the boys falls apart and go through dark periods (I don't know what that says about me) so I will let you know if I find more. I know I've read more fics that fit your description but I will have to dig them up. If I find them, I'll let you know. I'll probably stalk this post to see who else puts things up, lol.

Thank you so much! They all sound like awesome stories.

And the code for html is

There's The Bright Lights of Disturbia, which is very, very long, but finally complete. Lots of messed up Dean and guilty Sam towards the middle/end.

http://community.livejournal.com/leonidasden/34359.html

Thanks for much for the link. I'm already on the 5th chapter lol. What a great story!

Welcome... it gets really, really good towards the end too!

I don't know if you've already read this, but it mostly fits your criteria. It's an AU set directly after "In My Time of Dying". Sam is left to deal with the fallout after John leaves Dean. Sam realizes how much he and John really hurt Dean after they left, and how emotionally fragile he really is. Features Depressed!Dean.

It's Wincest, which you said is fine with you, and one of my favorite stories of all time. I cannot recommend it enough.

http://samdean.archive.nu/viewstory.php?sid=976

Thanks for the link =) I don't think I've read it before, but it sounds great.