Himeko's transformation isn't about becoming prettier for anyone else, it's about a boy in a dress teaching her to see herself differently. The comedy lives in the genuine weirdness of the setup, not in mocking it. By the time you realize this is actually about two people learning what they care about, the show has already made you invested in their ridiculous, specific friendship.
Tachikawa Himeko is an ordinary, unremarkable high school girl. Her routine changes when Mikami Tochiotome, a good-looking boy, comes to board at her home. Tochiotome enjoys dressing as a girl, and his sense of fashion opens Himeko's eyes to beauty and style for the first time. The comedy OVA adapts Wao Akira's shoujo manga, and its nine episodes were first released on DVDs packaged with issues of Ciao magazine.