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Little attention has focused on generational or age-related differences in human immunodeficiency virus/sexually transmitted infection (HIV/STI) risk behaviors among Black men who have sex with men and women (BMSMW). We examined sexual risk behaviors between BMSMW ages 40 and under compared to over age 40. Analysis was conducted using Centers for Disease Control and Prevention (CDC)-sponsored intervention data among BMSMW in Los Angeles, Chicago, and Philadelphia (n = 546). Pearson's chi-square tests were conducted to evaluate associations between age groups and behavioral outcomes. Logistic regression was used to evaluate the odds of behavioral outcomes by age group, adjusting for sexual orientation and study location, within strata of HIV status. HIV-positive BMSMW over age 40 had 62% reduced odds of having a nonmain female partner of HIV-negative or unknown status compared to those ages 40 and under (adjusted odds ratio [AOR] 0.38, 95% confidence interval [CI] = 0.15, 0.95). Among HIV-negative BMSMW, the older cohort was associated with greater odds of having condomless insertive anal intercourse (IAI) with most recent main male partner (AOR 2.44, 95% CI = 1.12, 5.32) and having a concurrent partnership while with their recent main female partner (AOR = 2.6, 95% CI = 1.10, 4.67). For both groups, odds of engaging in certain risk behaviors increased with increasing age. Prevention efforts should consider generational differences and age in HIV risks among BMSMW.

African-American men who have sex with men and women (MSMW) are among those most heavily impacted by HIV in the United States, and those who have histories of incarceration are at further risk of infection. The Men in Life Environments (MILE) HIV prevention intervention was developed to provide culturally appropriate skills-based education and support for African-American MSMW with recent histories of incarceration. The MILE's conceptual framework was informed by three theories: Theory of Reasoned Action and Planned Behavior, Critical Thinking and Cultural Affirmation Model, and Empowerment Theory. The theory-based framework posits that improving racial pride is crucial in building self-efficacy and intentions that in turn promote health-protective behaviors. Therefore, our study aimed to assess whether baseline associations between racial pride and condom use self-efficacy, intentions, and behaviors among African-American MSMW with histories of incarceration align with our conceptual model. We report data on 212 participants recruited from Los Angeles County Sheriff's Department Men's Central Jail and the local community. Using structural equation modeling, we tested two separate models: one with female sexual partners and one with male sexual partners, while stratifying by participant's HIV status. Only among HIV-negative participants was greater racial pride associated with less condomless intercourse with men. In this group, greater self-efficacy and intentions-but not racial pride-predicted less condomless intercourse with women. Our findings suggest that racial pride is an important factor to address in HIV prevention interventions for post-incarcerated African-American MSMW.