This study investigated how early experience with racial discrimination affected the subsequent risky sexual behaviors of a diverse sample of African American youths (N = 745). The analyses focused on 3 risk-promoting factors thought to mediate the hypothesized discrimination → risky sex relation: negative affect, affiliation with deviant peers, and favorable attitudes toward risky sex. In addition, attentive parenting was examined as a protective factor. Analyses using structural equation modeling revealed that youths who perceived more racial discrimination at age 10 or 11 were engaging in more sexual risk taking at age 18 or 19. This relation was mediated by the hypothesized risk-promoting factors via pathways that were consistent with our conceptual model. Results also indicated a prospective reciprocal relation between parenting and children's deviant affiliations: deviant peer affiliations at age 10 or 11 predicted more attentive parenting behaviors by the parents; this response from the parents, in turn, predicted relatively fewer deviant affiliations when the youths were 15 or 16. Study findings are discussed in terms of their relevance to the disproportionately high rates of sexually transmitted infections among African Americans.