This article presents a case study of Simon, a 25-year old Black South African male. According to his Pedi customs, Simon underwent traditional male circumcision (TMC) as a 12-year-old adolescent. He tells of his fears relative to this experience and how, over time, he transitioned from a belief in TMC to a strong preference for medical male circumcision (MMC). Using a single-case study design, the aim of the research was to explore the value of the exercise of choice in TMC, which may influence cultural perceptions of gender and masculinity. The study unpacks the way in which the meaning and experience of TMC is shaped by the social and cultural contexts of South Africa. This qualitative exploration complements conventional medical accounts of circumcision, which are often focused on the medical procedure while ignoring cultural and social factors. Issues of gender, particularly the construction of hegemonic masculinity and how it positions men, women, and young boys in relation to each other and their communities, are discussed. Simon’s case study provides new insights and perspectives on personally and culturally sensitive issues which are not easily accessed nor commonly understood. Data collected via in-depth interviews were transcribed and analyzed thematically. Analysis applied information from the literature and key concepts from the theoretical standpoint of social constructivism. Case study analysis allowed space for unexpected, emergent themes to arise from the data. Four main themes were identified, notably language, silence, patriarchy, and masculinity.