I Get the Feeling I've Lost as a Woman.

Having forcibly been dressed in a maid uniform, Hime Arikawa is chased down by two men, but is saved by the three girls of the Shimoshina High School student council from his school: president Unko, vice president 18-kin, and secretary Albertina II. They immediately invite him to join the student council, but are shocked to discover Hime is actually male. Hime explains that his parents forced him to assume a large amount of debt and the two men were debt collectors. The girls offer to pay off his debt, but in exchange, Hime has to spend the rest of his high school life cross-dressing as the student council's dog. Hime agrees to their terms, and the girls introduce Hime at an assembly in front of the other students, in the process revealing he is cross-dressing.

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S01E02 - I'd Totally Hit That