The dramatic racial disparities in the rates of HIV/STIs(sexually transmitted infections) among African Americans make understanding broader structural factors that increase the risk for HIV/STIs crucial. The current study of young 564 African American men attending STI clinics investigated whether those who had ever been incarcerated reported recent sexual behaviors relatively more risky than their counterparts who had never been incarcerated. Participants were recruited from clinics treating STIs in three southern U.S. cities. Males 15 to 23 years of age who identified as Black/African American and reported recent (past 2 months) sexual activity were eligible. Linear mixed-effects models and generalized estimating equation models were used to assess associations between baseline incarceration history and sexual risk behavior over a 6-month follow-up period. Mean age was 19.6 years (SD = 1.87). At baseline, 240 (42.6%) men reported history of incarceration. Incarceration history predicted several risk behaviors over a 6-month follow-up period. Compared with those with no incarceration history, men previously incarcerated reported a desire to conceive a pregnancy (β = .40, p = .02), were less likely to have used a condom at last sex act (odds ratio = .91, p = .02) and were more likely to have used drugs and alcohol before sex in the past 2 months (β = .69, p < .001; β = .41, p < .001). A history of incarceration may influence the sexual risk behavior of young African American males. Prevention programs and interventions should intensify support for postincarceration African American males to help mitigate this behavior.