#2 I love reluctantly bottoming/secretly a needy bottom Dean fics; they're awesome!

A Matter of Trust by philalethia
http://philalethia.livejournal.com/238046.html
The first time is an accident, but accident or not, it leads them them down a road they may or may not be ready for.

The World That I See Inside You by Little Miss GG http://littlemissgg.livejournal.com/162121.html
Sam's imagined it many, many times now if only he can get away with it.

Persuasion by lazydaze
http://lazy-daze.livejournal.com/493388.html
Sam and dean have fooled around but before they can take the plunge one of them has to agree to be the bottom

For #3 you can check out

Tangled Up In You by leonidaslion http://community.livejournal.com/leonidasden/48781.html
Whilst taking a break Sam and Dean have trouble convincing their hostess that they really are brothers, and after awhile the distinction hardly seems to matter anyway.

The Little Spoon by leonidaslion http://community.livejournal.com/leonidasden/48459.html
Sam and Dean engage in some stealth snuggling. The question is who's fault is it and will they stop?

Travel Insurance by Juli
http://samdean.archive.nu/viewstory.php?sid=117
When Dean and Sam get on another plane they learn that sometimes it's nice for the protector to be protected and the protected to protect.

For #1, if you haven't already read it
The Bright Lights of Disturbia by leonidaslion
Dean is damaged and Sam doesn't know why, all he does know is that it has something to do with mirrors, with scars, and with his own desire.
http://community.livejournal.com/leonidasden/tag/disturbia