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.Many female-to-male (FTM) transgender persons, or transmen, are at high risk for HIV infection. This has been overshadowed to a great extent by the HIV risk and prevalence among male-to-female (MTF) transgender persons, or transwomen. However, there has been some recognition that many transmen identify with the gay community and have non-trans gay men as sex partners (Clements-Nolle, Marx, Guzman, & Katz, 2001;Herbst et al., 2008;Sevelius, 2009). The San Francisco Department of Public Health recently included TMSM (transmen who have sex with non-trans men) within the larger HIV risk group MSM. HIV prevalence among MSM in San Francisco was recently estimated to be 24.3% (Scheer et al., 2008), and HIV was characterized as being hyperendemic in the gay community. The Centers for Disease Control and Prevention reported at the 2010 National STD Prevention Conference that gay men are 44 times more likely to acquire HIV than other men (Roehr, 2010). It is unknown if these statistics apply equally to transmen. This study was conducted in order to understand and explicate the situated HIV risk of transmen who identify as gay.