This takes place during the last couple seasons
Sam and Y/N met on a job hunting a succubus and an incubus. They started texting, then calling, then Y/N moved into the bunker. Their relationship is getting pretty serious, but will hunting get in way, or get one of them killed.
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When Dean has had enough of the constant back and forth flirting between you and Sam, he decides to take matters into his own hands. But, after slipping Sam some dream root, things don't exactly go as planned.
(Trigger Warnings!)