In the United States, there is an urgent need to provide HIV prevention services to African American men who have sex with men and women (MSMW) but who do not identify as gay or homosexual. Engaging these men in HIV prevention has historically been challenging. This study used qualitative methodology to explore the beliefs and experiences from community-based service providers (n = 21) and from African American MSMW (n = 21) regarding the provision of HIV prevention education and counseling to these men. Data analysis revealed that (a) African American MSMW who do not identify as gay can challenge service providers' assumptions about sexual behavior and sexual identity; (b) service providers' attitudes toward these men can be affected by ambivalent or negative beliefs that pervade the general community; (c) African American MSMW need safe and nonjudgmental spaces that offer HIV risk reduction, but they also might experience anxiety about disclosing same-sex behaviors to counselors. Findings highlighted the complexities related to culture, masculinity, and sexuality as determinants of HIV risk in African American MSMW, and findings also revealed tensions between these factors that may affect the quality of HIV prevention services. Service providers may need additional training to provide appropriate and non-judgmental HIV prevention counseling and education.