Most persons aware of their HIV-positive serostatus refrain from sexual behavior that could transmit HIV infection to others. However, a minority of men who test HIV-seropositive continue to engage in transmission risk behavior. One factor that may play a role in high-risk sexual activity involves sexual behavior self-management. The present study investigated the role of sexual compulsivity as a contributing factor to high-risk sexual behavior in HIV seropositive men who have sex with men (N = 112). Participants also completed measures of factors known to be related to risky sexual behavior including: personal substance use, sexual partner substance use, pleasure associated with high-risk activities, beliefs about transmission risks, intentions to avoid future instances of risky behavior, and self-esteem. Men scoring high on sexual compulsivity reported engaging in more frequent unprotected sexual acts with more partners, reported greater use of cocaine in conjunction with sexual activity, rated high-risk sexual acts as more pleasurable, and reported lower self-esteem. Mediational analyses indicated that the relationship between sexual compulsivity and high-risk sexual behavior was partially mediated by both personal cocaine use and partner cocaine use in conjunction with sexual activity. The results suggest a need to integrate HIV risk-reduction services and substance use treatment for those persons living with HIV who have difficulty avoiding transmission risk behavior.