Black men who have sex with men and women (BMSMW) are at increased HIV risk, but few efficacious interventions meet their unique needs. Three HIV prevention interventions were evaluated with a common protocol. Baseline data were pooled to describe sexual behavior involving transmission risk with male, female, and male-to-female transgender partners and identify factors associated with transmission risk. BMSMW from Los Angeles, Philadelphia, and Chicago who reported sexual risk and bisexual behavior in the past year were recruited via modified chain referral sampling and community recruitment. Baseline assessments were conducted via audio computer-assisted interview and sexual behaviors assessed over the past 3 months. From December 2010 to November 2012, 584 BMSMW were enrolled across the three cities. More than half (55%) were recruited by other participants. Overall, the mean age was 43 years. Seventy-five percent reported an annual income <$10,000 and selling sex was prevalent (31%). Three-quarters identified as bisexual. Thirty-nine percent were HIV-positive. Among HIV-positive participants, 46% reported sex without condoms with HIV-negative or unknown male partners and 45% with HIV-negative or unknown female partners. Overall, factors associated with sex without condoms included network size, education, income, sexual orientation identification, HIV status, exchange sex, homonegativity, and social support. Findings support the need for enhanced HIV prevention efforts for this population. Future studies should examine contextual factors in addition to individual risk behaviors to inform the development and implementation of promising strategies to prevent HIV and promote the overall health and wellness of BMSMW and their sexual partners.