Cross Dressing Movies

Superman's pal Jimmy Olsen gets his own story. Boy meets girl. Boy loses girl. Boy meets boy!

Selfhood follows 5 individuals and the difference between their sense of self compared to how they present theirselves to the outside world.

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

The original documentary on the Wigstock festival, back in the day when it was a much smaller affair in Thompkins Square Park. A full day of peace,...

A cross-dressing Adolf Hitler sings tasteless, but humorous musical numbers.

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

Lillian dresses as a man to gain access to a boy's school.

To conquer his beautiful mother without insospettirne, Polidor dresses for women and can thus safely visit the house, but was immediately made...

Two guys found a treasure map. They decided to make a plan to approach and figure out the truth behind it. One had to disguise as a woman and other...

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