The Headmaster is a game about being the headmaster at a remote girls academy for young women located in the UK, the students failed their exams or were troublesome causing them to be sent to the academy in the hopes of being rehabilitated and to pass their exams, the government has allowed the use of corporate punishments and the mysterious school owners allow you to use your disciplinary methods of pain, humiliation, and pleasure. All students are between the ages of 18 - 19 years old.