Men who have sex with men and women (MSMW), particularly Black MSMW, are at high risk for HIV. However, few studies have focused on factors that influence Black MSMW’s specific HIV risk behaviors, and there are no evidence-based interventions specifically targeting this population. Some studies have suggested that masculine ideals are associated with high-risk sex practices and partners. Norms around masculinity in the social environments in which MSMW live may prohibit nonheterosexual identities and behaviors, may lead to internalized homophobia, and may promote high-risk strategies to seek male partners. Using data collected from 180 Black and 101 White MSMW recruited for a study to develop strategies for recruiting MSMW for research and services and to inform the content of HIV prevention messages, we examined the association between hypermasculinity ideals and sexual behaviors that may contribute to increased HIV risk among Black MSMW and a comparison group of White MSMW. Comparing Black and White MSMW, we explored how this association may differ by race. Multivariate models, controlling for sociodemographic and other covariates, indicate that hypermasculine ideals are associated with increased numbers of male and female partners among Black MSMW and an increased number of female partners among White MSMW. Hypermasculinity is important to address in programs that aim to reduce HIV risk among Black MSMW.