High HIV prevalence and incidence rates and high-risk sexual activity have been documented in certain subgroups of the transgender community; however, less is known about the sexual experiences and risks shared by these subgroups. To identify contextual features influencing the sexual risk-taking of transgender adults, semi-structured interviews conducted with 41 self-identified transgender adults were analyzed via constant comparative analysis, a technique rooted in grounded theory. Seven aspects of the transgender experience, including stigma, financial hardship, sexual objectification, a lack of outreach, hormones, a second puberty, and gender role issues, created a unique context of risk. Findings indicate that traditional HIV prevention efforts might not be suited to the unique needs of transgender adults. Tailoring HIV prevention efforts to this community will warrant further attention to contextual influences on sexual risk and safety.