The article focuses on a very specific form of transactional sex that exists at a university campus in Zimbabwe, which students refer to as ‘pimping.’ Drawing extensively on the specific experiences of a male student pimp, the article demonstrates that, in practice, transactional sex takes different forms and is not always confined to two parties (namely, a woman and a man). In this case, ‘pimp-mediated’ transactional sex introduces a third person – the pimp – into what is traditionally understood to be a relationship between the two parties and, in the process, dramatically transforms the social obligations that define this particular social relation. A major transformation that occurs in pimp-mediated transactional sex is that it makes the pimps, rather than the women, the central people in these relationships. This, I argue, makes transactional sex more efficient and potentially increases the female participants’ vulnerability to HIV infection.