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To describe and evaluate risk factors for HIV/sexually transmitted infections (STIs) among male-to-female (MTF) transgender persons.Using the life chart interview, potential lifetime risk factors for HIV/STIs among MTFs were measured and evaluated in conjunction with lifetime exposures for HIV, syphilis, hepatitis B, and hepatitis C. The participants were 517 MTFs between the ages of 19 and 59 years from the New York metropolitan area.HIV/STIs were low among white Americans and very high among Hispanics and African Americans. In the latter groups, HIV and hepatitis B were associated with an androphilic sexual orientation, lifetime number of commercial sex partners (sex work), and the social expression of transgender identity; syphilis was associated with lifetime number of casual sex partners; and hepatitis C was associated with injection drug use, unemployment, and social expression of transgender identity. In multivariate models, the social expression of transgender identity was the strongest and most consistent predictor of HIV/STIs. Consistent with their lower levels of infections, white Americans reported significantly lower levels of the risk factors found to be predictive of HIV/STI among Hispanics and African Americans.HIV/STI prevention in this population should be targeted at Hispanic and African Americans. Prevention programs should incorporate multiple components designed to address the diverse issues confronting ethnic minority transgender persons, with an emphasis on the social expression of transgender identity.