In this article we examine the dynamics of social relationships in which alcohol use and risky sexual behaviors cooccur. As part of a larger biological and behavioral HIV surveillance survey, 20 men who lived in an urban, informal settlement on the outskirts of Cape Town, South Africa participated in in-depth interviews. Interview transcripts were analyzed according to a latent content analysis. Findings highlight the latent association between alcohol and transactional sex, and enable an in-depth examination of the normative role that alcohol plays in the formation of casual sexual partnerships characterized by exchange. We build on an existing conceptual model that traces the potential pathways by which alcohol use and transactional sex are linked to sexual risk behaviors. The study findings point to the need for multilevel HIV risk-reduction interventions among men to reduce excessive alcohol use, risky sexual behaviors, and underlying perceptions of ideal masculinity.