This paper looks at the transformation of male-to-female transgender identities in Japan since the Second World War. The development of print media aimed at a transgender readership is outlined as is the development of bars, clubs and sex venues where transgendered men sought both partners and commercial opportunities. The origin of various transgender 'folk categories' such as okama, gei bōi, burūbōi and nyūhāfu is discussed and their dependence upon and relationship to the entertainment world is outlined. Finally, the paper looks at how the resumption of sex-change operations in Japan in 1998 has led to a new public discourse about transgender phenomena that utilises a range of medical terminology. While the recent establishment in Japan of clinics for individuals who consider themselves to be transsexual is an important development, it is argued that other transgenders who identify with indigenous categories are sceptical about the new medical model which they regard as both reductionist and pathologising, and that their experience should not be overlooked when giving an account of constructions of transgender experience in contemporary Japan.