Himegoto - Episode 9

The story follows Hime Arikawa, a boy who is being chased down by scary people. However, he is rescued from danger by the girls in his school's student council — 18-Kin-san, President Unko, and Beru-senpai. The student council will assume Arikawa's debt under one condition: "As the student council's dog, you will spend your high school life in women's clothes."