Transactional sex refers to selling sex (exchanging sex for money, drugs, food, shelter, or other items) or purchasing sex (exchanging money, drugs, food, shelter, or other items for sex). These activities have been associated with a higher risk for HIV and other sexually transmitted infections in a variety of populations and settings. This paper examines correlates of purchasing and selling sex in a large sample of drug users, men who have sex with men, and sex partners of these groups. Using respondent-driven sampling, participants were recruited between 2005 and 2008 in two urban and two rural counties in North Carolina. We used multiple logistic regressions to examine separate models for selling and purchasing sex in men and women. In addition, we estimated direct and indirect associations among independent variables in the logistic regression models and transactional sex using structural equation models. The analysis shows that factors associated with women selling and buying sex include being homeless, use of stimulants, bisexual behavior, and neighborhood disorder. There was also a significant difference by race. For men, the factors associated with selling and buying sex include being homeless, bisexual behavior, and not being in a relationship. Although neighborhood violence and disorder show significance in bivariate associations with the outcome, these associations disappear in the structural equation models.