I swear I've read something like #2 fairly recently on the kinkmeme. I'll let you know if I find it again!
ETA: Although obviously it's not set after 9.08, but it has similar themes.
ETA2: Found it! Although it's not recent at all apparently, I just haven't read it till now. This Is All Very Meta by road_rhythm Summary: Dean didn't get there first. That's okay; hell, that's the way he wanted it. He never even cared—until he stumbled over some stupid freaking fanfic about him taking Sam's virginity. Now he can't get it out of his head.
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timeasmymeasure
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Date: 2013-12-02 08:45 am (UTC)ETA: Although obviously it's not set after 9.08, but it has similar themes.
ETA2: Found it! Although it's not recent at all apparently, I just haven't read it till now.
This Is All Very Meta by
Summary: Dean didn't get there first. That's okay; hell, that's the way he wanted it. He never even cared—until he stumbled over some stupid freaking fanfic about him taking Sam's virginity. Now he can't get it out of his head.