Transactional sex among black South African women has become a mode of economic survival putting them at higher risk for HIV and other infectious disease. In order to inform HIV interventions, drug and sexual risk behavior correlates of recent transactional sex among a descriptive epidemiological, cross-sectional sample of 189, black, South African women in Pretoria were examined using log binomial regression. Prevalence of HIV seropositivity was extremely high among non-transactional sex workers (47.1%) and transactional sex workers (54.6%), albeit not significantly different. Adjusted regression results indicated that the probability of transactional sex was greater for drug using women who tested positive for cocaine use (Adjusted Prevalence Ratio (APR)=1.3, 95% CI=1.1, 1.5) and knew of anyone who died of AIDS (APR =1.5, 95% CI 1.1, 2.1). The probability of transactional sex was lower for female drug users who reported greater education (APR =0.6, 95% CI= 0.4, 0.8), condom use in their first sexual encounter (APR =0.7, 95% CI=0.6, 1.0) or reported a recent steady sexual partnership (APR =0.8, 95% CI=0.7, 0.9). Drug use-related interventions for female transactional sex workers may need to focus on methods for the reduction of not only drug use, especially cocaine use, but also the reduction of sexual risk behaviors.