Cross Dressing Movies

Based on the stage musical of the same name, this is the tale of a princess who grew up loving fairy tales and finds herself thrust into one where...

A young woman must pretend to be a man to visit her grandfather, and gets into some romantic scrapes in the process.

An orphan moves to the city to find work but discovers that women's wages are significantly lower than men's. Unwilling to abide by this injustice,...

Macho shows concerns about his wife cheating on him by live streaming herself nude while spreading the fact that Macho is a mysoginist.

Martina and Sonja, cross-dress in vampire capes and werewolf claws, re-enacting familiar horror tropes. A corresponding soundtrack of stock screams...

An extremely sympathetic and interesting look into how some couples came to terms with transness and crossdressing in the late eighties and early...

A young woman cuts her hair and dons men's clothing to escape her wealthy but quick-tempered father.

A set of seven portraits consisting of personal accounts from the lives of gays and lesbians. The narration includes stories about coming out,...

Man impersonates a female typist.