Cas and Dean are both retired from their normal jobs (teaching and working in the shop) and hunt occasionally. Claire graduated high school and got married to her friend Aiden, Dustin married Josephine, and Krissy married Ben, Lisa's son. All of them hunt together, mainly focusing in Indiana.
Sam and Jess had another kid, a girl named Bela, of all names. Their uncle Bobby married a sheriff, Jody. Jo grew up to be a hunter and a cop, and died with her mother, Ellen, and Ash on the job. Zachariah got possessed by an angel and was killed during the apocolypse, which we stopped from happening. Benny got turned into a vampire, and killed by Martin, a hunter.
All in all, most of their friends died. Somehow, Sam, Cas, and Dean managed to stay alive. And their kids grew up to be strong, which is what's important.
Every morning, Dean wakes up next to Cas and smiles, knowing that they were part of the lucky few.
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Hayran KurguDean Winchester and Castiel Novak grew up together. They were best friends. Things happened, and they ended up with some tattoos...