CROSSDRESSING

39
PG-13

Chou Kuse ni Narisou

Shiratori Nagisa is a pink haired singing idol, continually badgered by her father to find new disciples for the family dojo. In an attempt to gain free-time as a normal kid, she cuts her hair and cross-dresses as a high-school boy. "Ootori Nagisa" enrolls in a run-down school, falling in love with a rival school's gang leader, Nosaka Akira. She soon finds out Nosaka-kun is a fan of Nagisa - The Idol. Keeping up the charade, they manage to sneak time together. Rivals for Nagisa's affection, BOTH their dojo-running fathers, as well as martial artist animals and an up-in-coming Idol conspire to make thier lives a complicated as possible. (Source: ANN)
TV Spring 1994 6.36
52
PG-13

Ribbon no Kishi

In the kingdom of Silverland, Prince Sapphire holds a big secret: he is actually a girl. When Sapphire was born, she accidentally received both the blue heart of a boy and the pink heart of a girl. To protect the kingdom from the evil Duke Duralumin, who is the successor to the throne, Sapphire leads a double life, posing as a boy as women are not allowed to reign. God assigns trainee angel Tink to retrieve Sapphire's boy heart, but she refuses to let go of it. As the Duke schemes to usurp the throne, Sapphire finds herself in an even worse predicament in the clash of her two identities—she falls for Prince Franz Charming from the neighboring kingdom. Sapphire and Tink now embark on exciting adventures, but along the way, they must fight various enemies to uphold the throne at all costs.
TV Spring 1967 6.72
1
Rx

Mellow

A story about a crossdressing teacher handling a delinquent class. Based on the same-name seinen manga by Rin Kasahara.
Ova Winter 1993 5.37
1
PG-13

Otome wa Boku ni Koishiteru: Trinkle Stars The Animation

Hisoka was an orphan who was raised by Yukitaka, the present head of the worldwide Jinsei Corporation, with the help of his right-hand man Daisuke. He was adopted for the sole purpose of working both publicly and secretly for his daughter Orihime, who was next in line to inherit the business. That’s why he did not hesitate when he was asked by Yukitaka to attend the same school as her and serve as her bodyguard in secret. The only problem was that her school was the refined Saint Ceral Girls’ Academy, which was closed to boys. He didn’t know it at the time, but it would be a major turning point in his life. (Source: VNDB, edited)
Ova Winter 2022 5.55

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