Objective: The first purpose was to determine whether sexual abuse involving penetration that occurred in childhood only, adolescence only, or both childhood and adolescence differently impacted whether community-recruited women had ever traded sex for money or drugs, their number of recent sex partners, and the number of times they had engaged in recent unprotected sex. The second purpose was to assess the mediating effects of adulthood rape, recent drug use, and recent sex with an injection drug user on these three HIV-risky sexual behaviors. Method: Women ( n = 1,490) recruited from three US sites were questioned about their childhood and/or adolescent sexual abuse histories, adulthood rape experiences, recent drug use, and adult HIV-risky sexual behaviors via structured interviews. Results: One-third of the women reported having experienced sexual abuse involving penetration in childhood and/or adolescence. Overall, regression analyses indicated a significant relationship between early sexual abuse and adult risky behaviors; rape in adulthood mediated this relationship for all three HIV-risky behaviors. Abuse that occurred in childhood only and abuse that occurred in both childhood and adolescence had a stronger impact on later risky behaviors than did abuse that occurred in adolescence only. Conclusions: Because childhood constitutes a critical period in individuals’ sexual, social, and personal development, sexual abuse precipitated during this time may distort women’s constructions of sex and sexuality. Women abused in childhood may therefore engage in HIV-risky sexual behaviors to a greater extent than women abused in adolescence as a result of these disruptions to their development. Rape in adulthood appears to intensify the effects of early sexual abuse, increasing abused women’s involvement in risky behaviors. Treatment that connects abused women’s experiences during development to their current behaviors is recommended to help them adopt safer sex practices.