Recently, ‘rent boys’ have become increasingly visible in the queer social spaces of Istanbul. They come from impoverished areas of the city and engage in compensated sex with other men. In this article, I examine how these heterosexually identified rent boys assemble and perform exaggerated masculinity in order to negotiate the tensions between their local socially excluded environments and an burgeoning western-style gay culture while they conduct their ‘risky’ sexual interactions with other men. Exaggerated masculinity repairs and masks the subverting effects of compensated sex for rent boys’ heterosexual subjectivities and makes them closer to the hegemonic ideals of masculinity. Through intense participant observation and 20 recorded interviews with rent boys and their clients, this study demonstrates how rent boys perform an assiduous self-governance through symbols and implicit meanings vis-à-vis different and contradictory class positions, gender identities, and sexual acts.