Psychopathic individuals are thought to have impersonal and sexually promiscuous relationships. Despite considerable theory on this topic (Cleckley, 1941), there is little research to support this contention. To fill this gap in research, the current study sought to examine the relation between psychopathy, promiscuity, and other risky sexual behavior. One hundred fifty-two delinquent youth between the ages of 11 and 18, were recruited for the study following contact with the juvenile justice system. Youth participated in four evaluations over two years to assess whether psychopathic traits predicted engagement in promiscuous sexual behavior and other risky sex practices. In addition, this study examined whether youth with psychopathic characteristics experience negative outcomes as a result of their sexual behavior. Findings indicated that psychopathic traits did not predict promiscuous sexual behavior, casual sex, or unprotected sex. Psychopathic traits (CU traits) however, were negatively associated with negative sex outcomes (e.g., pregnancy, STD infection), indicating that youth high in these traits experienced fewer negative outcomes. Demographic characteristics gender and age were significant predictors of risky sexual behavior at the 2-year follow-up including engagement in casual sex and promiscuous sex. Based on Moffitt's (1993) model of youth antisocial behavior trajectories, growth mixture modeling techniques were employed based on age of onset and past promiscuous sexual behavior to identify patterns of promiscuity over time. However, age of sexual debut did not discriminate different patterns of promiscuous sexual behavior in the present study. Overall, the results indicate that psychopathy was not a predictor of engagement in promiscuity and other risky sexual behaviors. Implications of the findings are discussed.