Transactional sex has not been studied much among men who have sex with men in Africa. Consequently, little is understood about attitudes towards the practice, the circumstances that give rise to it or how transactional sex relationships are managed. We conducted in-depth interviews with 81 Black men aged 20-44 from four low resourced townships in Tshwane, South Africa. We found that transactional sex was a widely used strategy for initiating and sustaining relationships with regular and casual partners, and was motivated by both the need for subsistence and for consumption. Alcohol-based exchanges in particular provided men in the townships with a covert and safe platform to communicate erotic, sexual and romantic attraction to other men, and bars and other drinking places were a popular venue for meeting potential sexual partners. The majority of 'feminine-identifying' men had engaged in transactional sex as the providers of money and material goods compared to men who identified as either 'masculine' or as 'both masculine and feminine'. Surprisingly, however, this did not necessarily give them greater control in these relationships. Our study provides an initial foray into a complex sociosexual phenomenon and suggests that gender identity is an important construct for understanding transactional sex relationships among men in Africa.