this is the first fic that came to mind. it's all about hurting Dean. I honestly don't recall if there was any Dean angsting about Sam. Set during Sam's time at Standford. Long dark fic. Beware the warnings :p

Bright Lights of Disturbia (http://archiveofourown.org/works/181007/chapters/266202)

I have already read this one but thank you for commenting.

Not sure that these fit exactly...

Dean solo, when Sam's at Stanford
Turn the Page
https://apocalypsos.dreamwidth.org/1286158.html
Dean gets a new hobby after Sam leaves for Stanford.

Land's End
https://www.fanfiction.net/s/3719763/1/Land-s-End
In limbo after Sam goes to Stanford and John heads out on a solo hunt, and short on cash, Dean takes a job that just may be more dangerous than the one he already has: crab fishing in the Bering Sea.

-------

Stanford era, hurt Dean
Crash
https://www.fanfiction.net/s/5825011/1/Crash
Set in the Stanford years. After a rough solo hunt, a hurting Dean camps out on Sam's couch. Sam's roommate notices a few things about Dean that Sam finds hard to hear.

Because of Houdini
https://www.fanfiction.net/s/5412180/1/Because-of-Houdini
Dean was born with cystic fibrosis, a chronic illness of the lungs. Sam struggles with juggling two lives. Something's killing people at Stanford.

Falling (maybe?)
https://www.fanfiction.net/s/5417294/1/
Dean experiences a serious illness (cancer) while Sam is away at Stanford and hides the leftover or recurring symptoms from him once Sam is back on the road. Then Dean collapses during a hunt...' Not a deathfic

-------------------------
After School Special
http://archiveofourown.org/series/6861
John found it when he was doing laundry. When John dug into the bottom of Dean's duffel to get the last of the dirty socks that had been sitting in there, probably, since the last time John had caved and done the laundry, he found a roll of bills. Tens and twenties, mostly, held together with a black binder clip. It was close to five hundred dollars.

Do Dandelions Roar (Dean is taken when Sam is at Stanford, and includes your second request, but he is protecting Sam originally)
http://singer-salvage.livejournal.com/42273.html
Two years ago Dean disappeared. Now John and Sam have gotten him back. But how will the three of them deal with the unexpected changes his trials in the time between have effected? And what does a goddess have to do with the whole thing?

Dean focused angst

Aftermath
https://www.fanfiction.net/s/3401472/1/


The Odds Are....
http://spn-au.livejournal.com/573626.html
This is a post Devil’s Trap story. It’s about the Winchesters and what happens when one of them is hurt and how all three cope with the fallout. It is a story of pain and despair, of hope and love. The Winchesters have known tough times in the past but Dean’s situation is the ultimate test of their bond to each other. The question is can they make a future out of such a troubled and bitter past?


Carouselambra (i think this is fits your second one from memory)
http://archiveofourown.org/works/336612/chapters/544434
Eight years after a hunt with John and Bobby that ended in disaster, Sam and Dean return to Johnston, Iowa for what looks to be a simple job. It isn't long before they realize that things are not always what they seem, and it's not so easy to escape a horror that refuses to stay dead. The reality of the situation flies in the face of everything they know about spirits and forces them to confront their biggest fears. With one Winchester struggling against a nightmare that keeps dragging him back under, and the other reeling from the knowledge of what his brother is willing to sacrifice to protect him, they will have to find the strength to stand together and defeat the ghost that haunts them both, once and for all.

Renovations
https://www.fanfiction.net/s/3610442/1/
Mostly Dean POV as he deals with an aftermath of a hunt

SUCH A LONG LIST. Actually, Carouselambra was what inspired me to make this post. What I read of it was interesting and well-written but contained the trope of the monster being after Sam and only settling for Dean so I had to stop and leave it for some other time. But the rest of these fics look great and right up my alley so thank you, thank you, thank you!!

Smack http://allowable-mist.livejournal.com/3698.html
Summary: Dean runs into more than he bargained for on what should’ve been a simple 2 day hunt. Can John save his son and put him back together?
Notes/Warnings: This story contains graphic drug use as well as graphic rape

Thank you!!

Stanford-era Dean with minimal Sam angst:

The 1300 Days (http://archiveofourown.org/works/695225) by stele 3 (this one has some Sam-related angst, but it's definitely very Dean-centric and there's none of the 'Dean is nothing without Sam' crap)

And My Flame Made a Pinnacle to Heaven (http://gekizetsu.net/sn/bonfire.html) by gekizetsu

Man's Allotted Span (https://www.fanfiction.net/s/4165502/1/Man-s-Allotted-Span) by Janissa11 (sequel to Land's End)

Highway Chile (http://art-savage.livejournal.com/18328.html) by art_savage

THANK YOU.

Ah, such a nice request. Let's see if I find something for you, or anyone else who might be interested.

I haven't read them all recently, so I hope my initial reaction that lead to them being bookmarked still stands true.

Stanford-era:

Lightning Crashes (http://www.fanfiction.net/s/4004174/1/Lightning_Crashes)
Preseries. It's been two years since the brothers have spoken, but several freak accidents on the Stanford campus have a rusty and out of the game Sam calling the one person he knows will always come through for him. Drama, banter, whump.

I just checked this one over - It really has the banter and bitchy-Sam-voice of early seasons down pat. Sam is annoyed and annoying, and Dean is long-suffering and annoying and annoyed. So - I hope you'll like it.



pre-series hurt Dean with human predator - it has four (?) sequels!
Payment Plan (http://minkmix.livejournal.com/81200.html)
When John fails to pay a debt a dangerous man comes after his children...(Outside POV which switches in the epilogues, of which there are four, yay!)

Maybe also this one.
Carnaveral (http://www.fanfiction.net/s/4254156/1/Canaveral):Just why does Dean hate Florida so much? Cocoa Beach, fuglies, allergies, and car accidents – Dean simply can’t catch a break. Pre-Season and early Season One. Hurt!Dean. Rated T for Language.

thank you!!

https://www.fanfiction.net/s/5658092/1/Sacrificial-Son

This kind of a mix of both. While the Winchesters are in town hunting a siren, Sam announces his plans to go to college and he and John get into it. Dean gets tired of reffing and goes off on his own and is assaulted and nearly killed by the siren. I like that it brings Sam, John, and Bobby and makes them realize how much they ask of him and how much he willingly sacrifices without being asked. John is a decent albeit distracted dad, Sam is somewhat selfish but no more than you would expect from a teenager who doesn't understand the world doesn't revolve around them and what they want and Bobby and Dean are very canon-compliant. I think you'll like it.

thank you so much!!