In a cramped dorm room, Bailey Wilde, a confident trans woman, and her roommate Jake Grand stumble upon Cassidy Cream's hidden transvestite paraphernalia. Bailey, intrigued by Jake's reluctance, coaxes him into trying on a pair of silky stockings and a restrictive chastity cage. Jake's initial discomfort gives way to arousal as Bailey and Cassidy tease him mercilessly, forcing him to masturbate in the cage and taste his own pre-cum. The taboo allure of sissification consumes Jake, and he eagerly awaits further feminization and humiliation at the hands of his roommates.