This study examined contextual influences on the relationship between peer norms for condom use and risky sexual behavior among African-American men who have sex with men. Analyses assessed the moderating effects of socio-demographic, socio-contextual, and health-related variables. One thousand forty African-American men, who have sex with men, ages 17 to 25 years, were surveyed as part of the Community Intervention Trial for Youth (CITY) from 1999 to 2002 in Atlanta, Georgia. Findings supported the hypothesis that participants who engaged in unprotected insertive anal intercourse, socio-contextual variables moderated the relationship between peer norms and risky sexual behavior. Findings also supported the hypothesis that participants who engaged in unprotected receptive anal intercourse, both socio-demographic variables and a health variable moderated the relationship between peer norms and risky sexual behavior. Findings have implications for intervention, policy, and research, including a need for interventions that recognize the contexts of influence that shape African-American MSM sexual behavior and that support norms for consistent condom use in both steady and casual sexual relationships.