Despite the popularity of peer education as an HIV prevention strategy across a range of contexts, understanding of the experiences of those intimately placed within these programmes is limited. Instead, the majority of research in this field relies on hegemonic notions of rational human behaviour that operate under the assumption that knowledge leads to sexual behaviour change. This study explored the experience of peer educators and peer facilitators in an HIV prevention peer education programme in Cape Town, South Africa. The empirical analysis draws primarily on the perspectives of four peer educators and four peer facilitators, and was supported by interviews with three NGO management staff. The findings reveal how gendered expectations and identities deeply influence the lives and experiences of the peer educators and peer facilitators. However, the HIV prevention programme also reinforces gender stereotypes and notions of a rational sexual being, rather than creating channels for the emergence of new understandings of gender, power, and sexuality. We conclude with a brief description of future directions for HIV peer education prevention programming based on critical engagement with gender power dynamics and contextualised lived experiences.