Tricky Love {Sabriel; Supernatural}

Sam Winchester has been hunting with his older brother, Dean for 10 years now. They've encountered many things, such as vampires, werewolves, demons, etc. They've had many close calls, and they've both died at least 5 times each. They always come back, though. Dean learned a while ago that he comes back because of an angel called Castiel, but Cas has only saved Sam once from Hell and he came back soulless. Who's saved him all the other times? He's about to find out....
*In this they haven't met Gabriel yet, but it is still in season 10, but nothing that happened in the show is actually happening in this. Also, Destiel is canon in this.*