Background: Most research on ‘Chemsex’ has been conducted with gay, bi-sexual, and men who have sex with men (GBMSM) in large cities with well-established infrastructures. Therefore, this study aimed to explore the ‘Chemsex’ risks and responsibilities of GBMSM who lived outside of the queer metropolis. This study also aimed to understand how stigma and mental health present in the absence of a well-established community infrastructure. Methods: This study utilized mixed methods in Leicester, Leicestershire, and Rutland, a location in the East Midlands of England. The quantitative component consisted of a survey. The qualitative component comprised three case studies based on in-depth interviews, using interpretative phenomenological analysis. Results: Of the 123 survey respondents, 86% engaged in riskier sex during sessions and 35% no longer enjoyed sober sex. In the interviews, the three men balanced risk management and personal responsibility, positioning themselves as mature, considerate, and well-educated users. All were alienated by the term ‘Chemsex’. The findings are considered using theoretical frameworks, or how discourses of ‘moral threat’ operate within the micro-politics of regulating GBMSM’s pleasure and stigma. Conclusions: The complexities of understanding this practice for researchers and practitioners are discussed and recommendations are made for reframing education and support services for GBMSM.