Himegoto (2014)

Himegoto follows Hime Arikawa, a second-year student at Shimoshina High School. Forced to assume a large amount of debt from by his now-absent parents, Hime is saved by the three girls of his school's student council after he is chased down by debt collectors. In return for paying off his debt, Hime agrees to their conditions of becoming the student council's "dog" and spending his high school life dressed as a girl.