A common thought about the designs of male characters in anime is that they look too feminine. The anime comedy Princess Princess takes that idea and makes it the basis of an entire show. Based on the manga by Mikiyo Tsuda, Princess Princess is now available in a box set after initially being released as individual volumes. It's a fun show for shoujo manga/anime fans and those who don't mind their pretty boys being pretty girls too.
The show begins with Tohru Kouno arriving at the elite boys' school Fujimori Academy as a transfer student. On campus, Tohru notices that everyone seems fascinated by him. Despite feeling a bit uncomfortable from all the attention, his teacher assures him that he'll fit in just fine. In class, he meets Yujirou Shihoudani, a boy so pretty that he initially mistakes him for a girl. Yujirou escorts Tohru to the dorm and it's there where he learns about the Princess program.
In order to provide excitement for the school's all-male student body, certain first-year students are selected and more or less forced into dressing up in girls' clothes. These princesses are revered by the student body much in the way actual female idols would be and receive benefits like free meals, free school supplies, and a cut of any money made from their likeness. Yujirou and another student, Mikoto Yutaka, are already princesses and Tohru is considered a prime candidate. Liking the benefits that the job offers, Tohru accepts the position and takes his place as one of the school's princesses.
Although much of the humor derives for the sheer oddity of the guys' situation, the characters keep it from simply being a one-note gag. Tohru and Yuujirou each have family issues (Tohru is an orphan who was raised by his aunt and uncle, for example) and develop a close friendship that hints at something more. Mikoto hates dressing up like a princess and is the only one of the three to have a girlfriend. This, along with his repeated attempts to keep his job secret from his girlfriend as well as the world outside the school, causes Tohru and Yuujirou to tease him mercilessly.
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