Three-hundred-eleven female drug-using sex workers in urban Puerto Rico were asked to describe their last negotiation with a client. They described efforts to protect themselves from many hazards of sex work, including violence, illness, and drug withdrawal. They also described efforts to minimize the stigma and marginalization of sex work by cultivating relationships with clients, distinguishing between types of clients, and prioritizing their role as mothers. Sex workers adopted alternating gender roles to leverage autonomy and respect from clients. Their narratives suggest that sex workers negotiate a world in which HIV is relative to other risks, and in which sexual practices which are incomprehensible from an HIV-prevention perspective are actually rooted in a local cultural logic. Future HIV prevention efforts should frame condom use and other self-protective acts in terms that build upon sex workers own strategies for understanding their options and modifying their risks.