Preliminary evidence has suggested that some transgender men who have sex with nontransgender men ("trans MSM") may be at risk for HIV and sexually transmitted infections and that their prevention needs are not being met. Quantitative (n =45) and qualitative (n =15) interviews explored risk behaviors, protective strategies, and perceptions of the impact of transgender identity on sexual decision making among trans MSM. A majority of the participants reported inconsistent condom use during receptive vaginal and anal sex with nontrans male partners; HIV prevalence was 2.2%. Risk factors included barriers to sexual negotiation such as unequal power dynamics, low self-esteem, and need for gender identity affirmation. Protective strategies included meeting and negotiating with potential partners online. Results of this study provide initial evidence that current risk behaviors could lead to rising HIV prevalence rates among trans MSM. Prevention programs must tailor services to include issues unique to trans MSM and their nontrans male partners.