A prison culture of masculinity shapes the prison macho – boys don’t cry. The prison macho is a real man who always hides his feelings and performs like a tough guy. These characteristics are much different from what happens in everyday life in the social spheres, where human being needs to be loved, need concerns and compassion from others and express these to others as well. In the current study, there is a recognition of a multiplicity of masculinities and an emphasis on how subjects are continually constituting and constructing their identity. Based on qualitative research, this study analyzes the patterns of masculinity embedded in the daily code of conduct used by prison staff to deal with prisoners and by prisoners to interact with other inmates and constitute their subculture. The investigation of prison sociology in the constitution of masculinity discourses in Tainan Prison contributes to both gender studies and to the literature exploring differences between western and eastern perspectives and policies related to incarceration.