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An abundance of scholarship centers on masculinities constructed in relation to other forms, resulting in hegemonic and subordinate designations. This article examines how street-based male sex workers in a recovery program articulate and enact masculinity. Some men embrace the program-endorsed hegemonic version, which encompasses sobriety, cessation of sex work, spiritual growth, participation in twelve-step groups, volunteering to recruit fellow sex workers, and attainment of conventional markers of success. In contrast, other men actively resist it. They do so by criticizing the program, and its directives, and embodying alternative masculinities aligned with ongoing illicit activities, including sex work, violence, drug use and street crimes. This paper underscores that even among a marginalized and disadvantaged population of men, the formation of masculinity is a relational process, one influenced by the broader organizational milieu.