Background. Despite the prevalence of sex work and strip clubs across Canadian urban geographies, few studies explore the occupational health and safety outcomes related to indoor male sex work, let alone male stripping whereby men dance for men. Moreover, the sexual service negotiation process in the sex work industry remains to be explored. In knowing that sexual practices with high HIV/STI rates occur in strip clubs (e.g., condomless oral, vaginal, and anal sex), as well as widespread psychoactive substance use among strippers, the purpose of this study was to explore the cultural features of male strippers’ work that impact their health and safety outcomes. Methodology. For this study, we recruited 14 male strippers working with male clients in a Canadian city. Critical ethnography was our espoused methodology. Through field observations, informal conversations, questionnaires, and semi-structured qualitative interviews, we explored the process of sexual transactions between strippers and clients. We used a postmodern angle to interpret our findings through the works of Deleuze, Guattari, and Foucault. Findings. The male strip club is a social matrix produced by the intersection of motivational forces: the motivation to gain money, pleasure, or intimacy, and the motivation to abide by socio-cultural and legal norms. It is upon a matrix of financial necessity and socio-cultural and legal constraints that sex work transactions unfold in the club. Moreover, the club’s health and safety conditions and strippers’ transaction outcomes result from intersecting motivations. Finally, sexual service negotiation is a process of configuring motivational forces between social agents. The motivation for financial gain revealed itself to be the strongest and most consistent force; the focus on capital gain generated asymmetrical connections between strippers, clients, and business entrepreneurs, resulting in specific health and safety outcomes. Conclusion. The Canadian legal and political context surrounding male sex work negatively impacts male strippers’ occupational health and safety conditions by disabling safe connections with clients. Further, the emphasis on money-making activities encourages strippers to value financial gain over their physical and mental integrity. In short, the male strip club work environment is configured in a manner whereby capital gain is prioritized and strippers’ health and safety is undermined.