Tooru walks in expecting a normal school life at an all-boys academy, instead finds out he's been volunteered into a dress-up role that should humiliate him, then actually starts enjoying it. The show's real trick is never making the cross-dressing the punchline; it makes it the permission structure for these guys to be softer with each other, to care about aesthetics and feelings without the usual armor. By the end you're not laughing at Tooru in a Gothic Lolita dress. You're watching a bunch of boys realize that femininity isn't contagion, it's just another way to be human.
Tooru's transfer to an all-boys academy seems straightforward until his classmates spring a surprise: he's been selected for the school's bizarre "Princess System." Good-looking first years are picked by the student council to dress as girls, in frilly Gothic Lolita outfits, at school events. The idea is to lift morale and soften the stiff, masculine mood of campus life. Two classmates, Yuujirou Shihoudani and Mikoto Yutaka, already fill the role, and Tooru is tapped as the third. He refuses at first, but once he learns that being a Princess comes with a range of privileges, he decides to take it on. The result is a cross-dressing school comedy adapted from Mikiyo Tsuda's shoujo manga.