Young Black men (YBM), aged 13 to 24 years, face a disproportionate burden of sexually transmitted infections (STIs). STI acquisition among YBM is due to incorrect and inconsistent condom use and is exacerbated by multiple sexual partners. Sexual and reproductive health is influenced by a complex interaction of biological, psychological, and social determinants that contribute to increased risk for STI acquisition. However, there are key social determinants of sexual health that play a major role in adolescent sexual risk–taking behaviors: gender norms, environment, peers, and families as well as a desire to impregnate a woman. Associations between contextual factors (risky environmental context, desire to impregnate a woman, and peer norms supportive of unsafe sex) and sexual risk behaviors were examined among a sample of YBM attending adolescent health clinics. This study used baseline data from a randomized controlled trial (N = 702). Parental monitoring was also examined as an effect modifier of those associations. Sexual risk behaviors were the frequency of condomless vaginal sex, number of sexual partners within the previous 2 months, and lifetime number of sexual partners. Mean age was 19.7. In the adjusted model, peer norms was the only significant predictor for all sexual risk outcomes (p < .05). Parental monitoring was an effect modifier for the perceived peer norms and lifetime sexual partners association (p = .053) where the effect of peer norms on lifetime sexual partners was lower for participants with higher levels of perceived parental monitoring.