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To describe homosexual men who continue to engage in unprotected oral and anal sex, 601 men who attended three urban STD clinics and who had engaged in these behaviors with a male partner in the previous 4 months were interviewed regarding their sexual and drug-use behaviors. Although approximately one fourth of participants had engaged in 1 to 2 episodes of unprotected anal sex, more than 20% reported engaging in greater than 23 episodes. Higher frequency of anal sex was associated with lower condom use rates. Although 50% had primary relationships, less than 22% had sex with just one partner, and less than 10% were in relationships concordant for HIV-antibody status. Multiple regression analyses showed that number of drugs used each month, sex in a steady relationship, and Hispanic ethnicity were the most consistent predictors of risk behavior across sites. Careful evaluation of the diverse nature and characteristics of these men is essential to target risk-reduction programs for this population.