Many behavioral studies of Black men fail to differentiate between those who have sex exclusively with men (MSM) and those who have sex with both men and women (MSMW). Respondent-driven sampling was used to recruit a total of 1,154 Black MSM and MSMW in New York City and Philadelphia. In descriptive analyses, MSMW and MSM were compared on several demographic, health, and behavioral risk correlates using chi-square tests. Differences in prevalence of unprotected anal intercourse (UAI) between these two groups were examined in two multivariate logistic regressions. Age, country of birth, self-identified sexual orientation, experience of being forced to have sex, self-reported HIV status, exchange sex for money/food/ drug, and drug use in the past 3 months were significantly associated with either insertive or receptive UAI in the past 3 months. The strongest correlate of either insertive or receptive UAI among both groups of men was engaging in exchange sex. Differences between MSMW and MSM were found in the areas of forced sexual experiences, disclosure of same sex behavior, and history of being arrested or incarcerated. Findings from our study highlight the need for specific HIV prevention interventions targeting Black MSMW as distinguished from Black MSM.