This article employs ethnographic methods to study the motivations and sexual behaviors of migrant women between the ages of 15 and 45 living in informal settlements near Rustenberg, South Africa. We build on the prior literature on female mobility in South Africa, which describes a history of women who, under coercion to maintain the rural homestead in order to support the formal male migrant labor system, used migration as a means to escape. Our informants were not only driven by a desire to flee their destitute rural communities, but also by a need for autonomy that would enable them to provide for their families back home. Guided by women who had made the journey before them, our informants’ arrival was marked by a realization that their economic security rested solely on their ability to establish relationships with men, who served both as long-term lovers as well as shorter-term transactional pursuits. This article dissects the complex nature of these relationships, which cannot simply be reduced to prostitution. The varying power dynamics are especially evidence in the case of condom use, and suggest that while women exhibit instances of empowerment, they are highly vulnerable to sexually transmitted diseases, particularly HIV.