A 2011 to 2015 4koma manga series by Tsukudani Norio with a summer 2014 anime adaptation. The series also had a 2012 spinoff, Himegoto+, which has been merged into the main series.
Himegoto is about a male high school student who is chased after by the Yakuza to pay off a debt incurred by his parents. He is saved by 3 girls who are members of the student council of school he attends, but ends up signing a contract where he must be their loyal dog and must always crossdress.
Himegoto+ focuses on the younger brother of Himegoto's main character, and revolves around him joining the Public Morals Committee to take back his older brother from the Student Council.