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African Americans are disproportionately affected by HIV/AIDS and other sexually transmitted infections relative to other racial groups. Although substance use has been linked to risky sexual behavior, the understanding of how these associations develop over the life course remains limited, particularly the role of social bonds. This study uses structural equation modeling to examine pathways from adolescent substance use to young adult sexual risk, substance problems, and social bonds and then to midlife risky sexual behavior among African American men and women, controlling for childhood confounders. Data come from 4 assessments, 1 per developmental period, of a community-based urban African American cohort (N = 1,242) followed prospectively from ages 6 to 42 years. We found that greater adolescent substance use predicts greater young adult substance problems and increased risky sexual behavior, both of which in turn predict greater midlife sexual risk. Although greater adolescent substance use predicts fewer young adult social bonds for both genders, less young adult social bonding is unexpectedly associated with decreased midlife risky sexual behavior among women and not related for men. Substance use interventions among urban African American adolescents may have both immediate and long-term effects on decreasing sexual risk behaviors. Given the association between young adult social bonding and midlife risky sex among females, number of social bonds should not be used as a criterion for determining whom to screen for sexual risk among African American women. Future studies should explore other aspects of social bonding in linking substance use and risky sexual behavior over time.