Comment on Chained to a comet by lily-fox
I can't separate Castiel from Jimmy in my head. I know people kind of accept that Jimmy's basically gone, maybe to Heaven, but every time Castiel gets hurt or has to go to Hell on an errand or sees something awful, I just remember that there's a guy in there who has to witness this and can't do anything about it. That sounds like hell to me. Like I just want to stop and give Castiel a backrub, mostly for Jimmy's benefit.
I always thought Jimmy hung around (remained trapped?) inside. Accepting that he can never be parted from Castiel again, but sort of still eternally committed to his decision to become a vessel. After all, his final choice was to save his daughter, and I feel like he would be at least somewhat satisfied that his final act was something so noble. And although he's stuck on the "ride" with everything poor Cas goes through, he'd know Castiel was grateful to him, and be happy that Castiel is getting to experience friendship, love, and lots of other things he would have missed out on as a regular angel.
That said, Castiel deserves ALL the backrubs.
That said, Castiel deserves ALL the backrubs.