Reduction in the incidence of high-risk sexual behaviors among HIV-positive men is a priority. We examined the roles of proximal substance use and delinquency-related variables, and more distal demographic and psychosocial variables as predictors of serious high-risk sexual behaviors among 248 HIV-positive young males, aged 15-24 years. In a mediated latent variable model, demographics (ethnicity, sexual orientation and poverty) and background psychosocial factors (coping style, peer norms, emotional distress, self-esteem and social support) predicted recent problem behaviors (delinquency, common drug use and hard drug use), which in turn predicted recent high-risk sexual behaviors. Hard drug use and delinquency were found to predict sexual risk behaviors directly, as did lower self-esteem, white ethnicity and being gay/bisexual. Negative peer norms strongly influenced delinquency and substance use and positive coping predicted less delinquency. In turn, less positive coping and negative peer norms exerted indirect effects on sexual transmission risk behavior through delinquency and hard drug use. Results suggest targeting hard drug use, delinquency, maladaptive peer norms, dysfunctional styles of escaping stress and self-esteem in the design of intervention programs for HIV-positive individuals.