Otome wa Boku ni Koishiteru: Futari no Elder The Animation

Otoboku 2 begins about two years after Mizuho's graduation. The main protagonist Chihaya Mikado was truant at his school because of harassment in the school and of a distrust in men. His mother cannot bear to watch him be in trouble, so she makes him transfer to Seio Girl's School, her old school. He dresses as a girl and introduces himself as Chihaya Kisakinomiya. Chihaya meets another protagonist Kaoruko Nanahara, who once rescued him from a playboy, and he begins to live in the dormitory building. He becomes the focus of public attention due to his attractive face and figure, and due to high grades at studies.

(Source: Wikipedia)