Despite high human immunodeficiency virus (HIV) rates among young Black men who have sex with men (YBMSM), there are limited data about condom use during first same‐sex (FSS). This study sought to understand socio‐contextual factors of 50 YBMSM aged 15–19 years that influenced condom use during FSS. Condom use was influenced by individual, partner, and community factors. Individual factors—recent illness or sexually transmitted infections (STI)—prompted condom use, while frequent HIV testing prompted nonuse. Partner factors—proactive encouragement from partners—prompted condom use, while trust and condom discomfort prompted nonuse. Larger community factors—such as presence of females—were key for use, while limited sexual health information combined with peers who discouraged condoms prompted nonuse. A multilevel approach may be useful in developing sexual health programming for these young men.