This study compared sexually transmitted infection (STI)-associated risks between young Black cisgender men who have sex with men (YBMSM) and young Black transwomen who have sex with men (YBTWSM). Comparisons pertained to: (1) prevalence of infections; (2) sexual risk; (3) partner-related risks; and (4) socioeconomic marginalization. YBMSM (n = 577) and YBTWSM (n = 32) were recruited from an STI clinic in the USA. Volunteers completed a computer-assisted self-interview and medical records were abstracted for STI/HIV information. Significantly greater prevalence of pharyngeal Chlamydia ( P < .001) and pharyngeal gonorrhea ( P = .04) occurred among YBTWSM; however, both associations were moderated and only significant for HIV-uninfected volunteers. YBTWSM had more oral sex partners and more frequent engagement in oral sex. The number of new sex partners for anal receptive sex was greater in YBTWSM. YBTWSM were more likely to exchange sex for money/drugs ( P < .001), have sex with men recently in prison ( P < .001), who were "anonymous" ( P = .004), or who were "one night stands" ( P < .001). YBTWSM were more likely to depend on sex partners for money food, etc. ( P < .001), to miss meals due to lack of money ( P = .01), and to report having ever being incarcerated ( P = .009). Compared to cisgender YBMSM, YBTWSM experience multiple risk factors relative to the acquisition/transmission of STIs and HIV.