Satisfaction and Condomless Anal Sex at Sexual Debut and Sexual Risk Among Young Black Same-Sex Attracted Men

First sex may be a sentinel event crucial to understanding sexual health trajectories of young Black same-sex attracted men (YBSSAM). We sought to understand whether satisfaction, condomless anal sex, and contextual factors during first sex were associated with sexual risk and recent condom use in YBSSAM. A total of 201 YBSSAM aged 15–24 years completed an Internet survey exploring first sex, current condom use, and sexual risk. High risk was defined as ≥3 of the following: new/concurrent sex partners, STI history, and no/inconsistent condom use. Multivariate logistic regression assessed the association between predictor (satisfaction and first condomless anal sex) and outcome (sexual risk and condomless sex in the past 3 months) variables. Mean age at first sex was 15.2 (SD = 2.9) years, and emotional satisfaction (51.7 %), physical satisfaction (63.7 %), and condomless first anal sex (55.2 %) were common. YBSSAM describing high levels of satisfaction were no more likely to be at high risk or engage in recent condomless sex. Condomless first sex (AOR = 4.57, p = .001), younger age (AOR = 3.43, p = .02), and having a partner >5 years older (AOR = 2.78, p = .03) at first sex were significantly associated with increased risk. Only condomless first sex (AOR = 4.28, p < .001) was associated with condomless recent sex. Satisfaction at first sex may not influence later sexual risk in YBSSAM. However, context of first sex, including condom use at first sex, may play an important role in subsequent risk. Prevention strategies on condom negotiation prior to first sex may help to mitigate HIV burden in YBSSAM.