So I just read The First Five Times, and it was beautiful, but now my soul hurts just a little bit. I really enjoyed the way you ended it though. On another note, I'm now going to read something full of fluff and sweetness.
I always feel so guilty when my fics hurt the souls of my readers. I have a couple happy fics, though. Sort of.
Constellations of Scars (post-series, M)
Mile-High Club (human!AU, E)
This Is What Dean Wants (alt-canon, M)
The Happiest Place on Earth (alt-canon, T)
Constellations of Scars is my go-to when I'm sad because it's my favorite fic I've written and makes me feel all sorts of happy squishy feelsies.