Cross Dressing Movies

An aspiring actor dresses up as a female nurse to bag a role in a film, and more importantly, woo the love of his life.

A trio of former sideshow performers double as the "Unholy Three" in a scam to nab some shiny rocks.

Lillian Travers, a New York heiress, pops down to Florida to surprise her fiancé, Fred Cassadene, the house doctor at a prominent Saint Augustine hote...

The stooges are singing comedic waiters, enlisted by two doctors to try and cheer up a depressed little girl, whose banker-father has gone missing wit...

A televised pantomime of Cinderella featuring various celebrities.

After her husband is captured during WWII, homesteader Alice is forced to maintain their land herself. One day, a wandering soldier named Barton stops...

Keeping the position of number one son requires a certain amount of ingenuity. Twelve year old Greg has inherited his father's competitive streak. On...

A hot young hustler finds himself in uncharted waters when he spends the night with a client who's far from the "johns" he's used to servicing.

Duk-jae is being overlooked at his marketing job and sublimates his unhappiness by getting drunk after work. His boss tells him he’ll be fired if he d...

Lillian dresses as a man to gain access to a boy's school. (from Performing Queer Female Identity on Screen: A Critical Analysis of Five Recent Films)

Italy 1757, Pippo Popolino, a lowly tailor, disguises himself as the great Casanova in order to romance the attractive widow Francesca. He little susp...

The station-master Fabian Bom is a very meticulous person, and he makes sure that the trains leaves exactly - on the second. To him, nothing could be...

An Asian-Irish cross-dresser's one-night stand with an exhibitionist turns life-threatening when a group of voyeurs discover they are not a woman.

Neil Bishop has spent his whole life living on the fringes of society. His only interaction with people is through his job as a lost luggage courier....

Madea's young great-grandniece, Tiffany, introduces her new boyfriend, Zavier, to her family and drops the shocking news to them: that the couple is g...

Filmed live at the Wilbur Theater in Boston, the self-proclaimed sweatiest woman in show business brings you her first ever standup special. Told in t...