Kent, a young straight submissive man, dabbles on the fringes of the world of BDSM. At a weekend party, he dresses as a woman for the first time and is surprised at how popular it makes him. Jerome, an older black man, is especially admiring, and names him Cindy. Soon Cindy is saying yes to the filthiest requests from Jerome. When Jerome asks Cindy to give a young black BDSM master his first sissy experience, she must work extra hard to please two men at once.