This study aimed to examine racial discrimination and relation to sexual risk for HIV among a sample of urban black and African American men. Participants of this cross-sectional study were black and African American men (N = 703) between the ages of 18 and 65 years, recruited from four urban clinical sites in the northeast. Multivariate logistic regression models were used to analyze the relation of reported racial discrimination to the following: (1) sex trade involvement, (2) recent unprotected sex, and (3) reporting a number of sex partners in the past 12 months greater than the sample average. The majority of the sample (96%) reported racial discrimination. In adjusted analyses, men reporting high levels of discrimination were significantly more likely to report recent sex trade involvement (buying and/or selling) (adjusted odds ratio (AOR) range = 1.7-2.3), having recent unprotected vaginal sex with a female partner (AOR = 1.4, 95% confidence interval (CI), 1.1-2.0), and reporting more than four sex partners in the past year (AOR = 1.4, 95% CI, 1.1-1.9). Findings highlight the link between experiences of racial discrimination and men's sexual risk for HIV.