Himegoto

The main protagonist of Himegoto, Arikawa Hime, is in serious trouble. He’s being pursued by loan sharks for the debt his parents left him with. That is, until the Shimoshina High School student council steps in to bail him out. These "kind" girls help Hime by paying off his debt and accepting him into the student council… as a beautiful girl, that is! Hime just happened to be wearing a French maid outfit when the council came across him, and now they won’t have him any other way. In return for paying off his debt, Hime must dress as a girl and be the council’s pet dog for the rest of his high school years. Still, things could be worse. After all, Hime is now surrounded by beautiful girls who constantly dote on him, expose him, and do naughty things to him. Thankfully, Hime has at least one person trying to get him out of this predicament: his little brother, who also happens to cross-dress. And then, of course, there’s the head of the disciplinary committee, who is… another cross-dressing boy!? This is getting ridiculous!