The use of sexual violence as a means of power and control within the South African prison system has been well documented. Sexual violence is intimately linked to the gendering of roles, such that rape and coercive sex is used as a brutal means of imposing a feminised identity; a violent enactment of who penetrates and who gets penetrated. Within this context, this article aims to examine both the performative and performed notions of gender and sexuality in relation to a prison theatre project located in a medium-security male prison in South Africa. I situate myself as a white feminist working within a black, all-male context, and examine moments from our theatre-making when men assumed feminised or female roles, and gender was actively and deliberately played with in an uncensored, open way. This article aims to analyse the relationship between the deliberate performance choices within the theatrical frame and the performative notions of gender and sexuality that are played out external to the theatrical moment. I question when and how prescribed gender scripts that dictate an aggressive and often violent masculinity might simultaneously be enacted and violated through theatrical performance. Drawing on my own reflections and interviews with participants, the article highlights how participants make sense of the gender choices made, and how these choices relate to wider questions of identity which need to be navigated. The issue of how such gender play might translate to a lived experience beyond the theatre space and outside of prison remains unknown, and further research is needed to understand the dynamics of the identities explored within the theatre event and how they are transferred to the world outside of it.