Himegoto

Hime Arikawa is a high school boy with a huge debt, and he is saved by the girls of his school's student council after being chased down by yakuza debt collectors. The student council agrees to pay off his debt if he'll join the student council and spend his high school life cross-dressing.

Note: The series continue after chapter 16 to Himegoto (Febri) and then to Himegoto (Comic Rex)