Many female-to-male transgender individuals, or transmen, are situated within the gay community, one of the highest risk communities for HIV, yet there has been little research regarding the experience of risk for these transmen. Seventeen transmen were interviewed regarding their sexuality and HIV risk behavior. Fourteen of the 17 reported having non-trans gay men as sexual partners. Risk behaviors included not using condoms with multiple partners who were HIV-positive, or of unknown HIV status. Aspects of risk included the unfamiliarity of the gay community and the lack of safe sex negotiating skills. The dynamics of acceptance and rejection between transmen and non-trans gay men impacted risk by compromising safety. Incorrect assumptions regarding transmen, non-trans gay men, and risk included beliefs that neither person could be at risk. Other aspects included the impact of testosterone on sexual behavior, the changed bodies of transmen, and sex work.