Tentacle anal fingering
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The Yellow-Eyed demon is dead. Vengeance extracted, Sam and Dean decide to try and get out of the hunting business and settle down. So Sam goes back to Stanford, Dean buys a beach house along the Californian coast, and things are simple for a while. Until it isn’t.
The one where the supernatural insists on finding Dean and where Dean doesn’t mind all that much. Not when the supernatural has tentacles, bluer than blue eyes, and is called Castiel.