Painted Angels by WinJennster
105,637 words, 25 chapters, published 12/16/2013, part 1 of the Painted Angels ‘Verse series

Summary: Author Castiel Novak has finally hit the big time, with a book based on his failed college relationship with a brilliant painter. He’s put all his pain behind him, but at a book signing, he comes face to face with Dean Winchester for the first time in twelve years, and the reunion doesn’t go like Cas hoped. Dean’s a broken man, with a lot of scars and secrets, shoulders weighed down by his demons and self loathing.
Cas sees a second chance with the man he’s never stopped loving, but Dean’s moved on, and is about to get married. Sam launches a “brilliant” plan to reunite his brother and his best friend, but Cas is worried it will all blow up in their faces, and he’ll go through the agony of losing Dean a second time.

Peanut Butter Pumpkin Wedding Cake by Sparseparsley
30,784 words, published 12/03/2009

Summary: Dean is a waiter in a strip club to put his kid brother through school. Castiel is dragged to the club as a part of his sister Anna’s bachelorette party. Dean and Cas hit it off, but Dean thinks Cas is the one marrying Anna.

Living in Agony by ChasingRabbits
120,136 words, 18 chapters, published 06/22/2014

Summary: Dean Winchester’s life is… well, it’s not great. He’s a gym teacher, he’s in his thirties, and he can’t seem to keep any part of his life straight. When the aftermath of a one-night stand goes awry, Dean is dragged kicking and screaming out of his cozy little closet and into the harsh light of reality.

Enter: Castiel Novak, the new history teacher, who knows full well that life gets crappy when you don’t allow yourself to live it in the way it needs to be lived.