Cross Dressing Movies

Low budget softcore farce where two men cross-dress to go into a women's prison.

Billy and His Pal, released on February 16, 1911, is about a cowboy, Jim (Francis Ford), who is idolised by young Billy (actress Edith Storey in...

An 18-year-old boy who came from the countryside to attend school. The person he was introduced to to share a room with by a real estate agent was a...

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,...

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.