Additional tags: CasDeanFlipFest, Enemies to Lovers, Angel Dean Winchester, Demon Castiel, Lawyer Castiel, Social Worker Dean Winchester, Custody Battle, Johns Winchesters A+ parenting, Bigotry & Prejudice, Implied/Referenced Child Abuse, Alternate Universe - Modern with Magic, Alternate Universe - Urban Fantasy, Hate to Love, Deans afraid of cars, Castiel Has a Dog, Drunk Sex, Tail Kink, Wing Kink, Wing Oil, Switching, Top Castiel/Bottom Dean Winchester, Bottom Castiel/Top Dean Winchester, Topping from the Bottom, Misunderstandings, Past Child Abuse, Minor Rowena/Sam Winchester/Gabriel, Minor Kaia Nieves/Claire Novak, Gender-Neutral Pronouns, Eventual Happy Ending
Summary: After years of working as Claire’s Guardian angel, Dean’s getting ready to let his Charge go. It’s time to let her make a life without him being there to protect her. He probably would have done it too, if he didn’t discover that Claire went behind his back making a deal with the infamous lawyer Castiel Gladius. With his past experiences making him wary of demon deals, Dean offers to take Claire’s place. Working for a demon he hates, just so his kid doesn’t have too. But will spending 66 days in the presence of the alluring Castiel lead to more than he ever bargained for?