This study examined the experiences of male cross-dressers (josōsha) and the cisgender men who are attracted to them (josōsha aikō dansei) in the Kansai region of Japan. The difficulties they faced are analysed as well as why these difficulties tend to be seen as personal issues rather than social problems. We conducted in-depth semi-structured interviews and observations with 13 josōsha and 3 josōsha aikō dansei and with one person who managed a video box shop. Gender boundaries were found to be fluid and shifting for cross-dressers and those attracted to them. Some remained close to their parents and children. Some faced the risk of hormone overdose, stigmatisation, sexually transmitted infection, and being 'outed' on the Internet. For josōsha, sexuality and sexual expression were seen as matters of individual preference not a personal or social identity. The gender identities and life experiences of josōsha are diverse, and the difficulties they experience are largely understood as being their own responsibility rather than as social issues or societal problems.