Objective: Childhood sexual abuse (CSA) among boys has been associated with a variety of subsequent maladaptive behaviors. This study explored a potential connection between CSA and an increased likelihood of risky sexual behavior in adulthood. Further, the study examined whether or not alcohol use may contribute to this relationship. Method: As part of a study on alcohol and sexual decision-making, 280 heterosexual men completed multiple background questionnaires pertaining to past and current sexual experiences and patterns of alcohol use. CSA history was obtained and severity ratings were made based on type of contact reported. Results: CSA was reported by 56 men (20%). Structural equation modeling revealed that CSA positively predicted number of sexual partners directly as well as indirectly, through its effect on alcohol use. Specifically, greater CSA severity predicted significantly lower age of first intoxication, which in turn predicted greater current alcohol consumption, followed by greater use of alcohol before sexual intercourse, leading to an increased number of reported sexual partners. The reported frequency of condom use was not predicted by CSA severity or the alcohol-use pathway. Conclusions: These findings suggest that CSA influences risky sexual behavior via multiple pathways and that more severe CSA may lead to elevated sexual risk indices. Moreover, these results suggest that men may elevate their risk of sexually transmitted infections via high numbers of sexual partners versus irregular condom use. Practical implications: These results highlight the need for adequate assessment and early interventions in order to mitigate the effects CSA may have on subsequent alcohol use and risky sexual behavior. Secondly, ensuring that male CSA victims understand the inherent risks of high numbers of sexual partners may be an effective strategy to interrupt the path toward risk-taking. (Contains 3 tables and 2 figures.)