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See more by tags PureTaboo Maisey Monroe

Maisey Monroe - Stealing Her Crush

Released: December 9, 2025

A lesbian teen, Anna (Sophia Sterling), invites her bisexual crush Bailey (Maisey Monroe) over for a movie night to get to know her better. Anna's stepdad Jake (Ryan Driller) is supportive and plays wingman in an attempt to help Anna, but it backfires when Bailey starts coming onto HIM instead. Bailey cheekily invites him to watch the movie with them, which leads to Bailey tempting Jake to fool around with her under a shared blanket. All the while, Anna is unaware. When Anna finally leaves the room for a short time, Bailey and Jake have lustful sex with a major almost-caught moment.