The heterosexual transmission of HIV has affected middle-age African American women at alarming rates; yet there is a paucity of research and interventions focused on this population. This study used a qualitative approach to understand middle-age urban African American women’s experiences with HIV-related sexual risk behaviors and to identify the sexual protective strategies they employed to reduce their risk for HIV infection. Ten African American women, ages 45 to 56, were recruited from low-income neighborhoods in New York City. Data were collected using in-depth interviews and analyzed using content analysis. Investigator triangulation and member checking were used to ensure rigor. Five salient themes emerged that highlighted the individual, gender/relationship power factors, and the sociocultural elements that influenced sexual protection or risk-taking behavior. Findings provide new insight into the complexities of HIV sexual risk behavior and can guide future HIV prevention interventions for middle-age, African American, urban women.