This study tested a developmental model of pathways to risky sexual behavior among South African adolescents. Participants comprised 633 adolescents, 12-17 years old, recruited from households in Durban, South Africa. Data were collected using in-person interviews. Topics included adolescents' sexual behaviors, household poverty levels, vulnerable personality and behavioral attributes, parent-child relations, and deviant peers. Structural equation modeling was used to assess the pathways to risky sexual behavior among the adolescents. The goodness-of-fit index (GFI) was .93. One major pathway indicated that family poverty was associated with difficulty in the parent-child relationship. This was related to vulnerable personality and behavioral attributes and to association with deviant peers, which, in turn, were related to risky sexual behavior. Findings suggest that poverty, parent-child relations, personality and behavioral vulnerabilities, and peer influences should be among factors addressed by prevention and intervention programs to reduce sexual risk behaviors by South African adolescents.