In light of evidence that racial discrimination and posttraumatic stress symptoms (PTSS) are neither rare nor extraordinary for many Black urban men, we examined the relationship between everyday racial discrimination and sexual HIV risk behaviors in a predominantly low-income sample of 526 urban Black heterosexually identified men; 64% of whom were unemployed and 55% of whom reported a history of incarceration. We tested the hypothesis that PTSS would mediate the relationship between everyday racial discrimination and sexual risk. Participants in the predominantly low-income urban sample ranged in age from 18 to 45 (M = 28.80, SD = 7.57). Three multiple regression models were used to test the study's mediational model. As hypothesized, PTSS mediated the relationship between everyday racial discrimination and sexual risk behaviors. Most participants (97%) reported experiences with everyday racial discrimination. Results empirically support the notion of racial discrimination-based traumatic stress as a pathway to Black heterosexual men's increased sexual risk behaviors. Results also highlighted key demographic differences with older men reporting fewer PTSS and sexual risk behaviors compared with younger men. Incarceration was related to both PTSS and sexual risk, underscoring the role that incarceration may play in Black heterosexual men's adverse health outcomes. Our study highlights the need for more qualitative and quantitative research to understand the nature of PTSS in Black heterosexual men and mechanisms such as substance use that may link traumatic experiences and sexual risk. Future research could also assess experiences with childhood sexual abuse, violence, and incarceration to gain a more in-depth understanding of the sources of traumatic stress in Black heterosexual men's lives. We advocate for the development of community-based individual and structural-level interventions to help Black heterosexual men in urban areas develop effective strategies to cope with racial discrimination-based traumatic stress to reduce sexual HIV risk behaviors in Black communities.