This study explores community members’ perspectives regarding the relationship between neighborhood characteristics and adolescent sexual behaviors in two rural, African American communities. The data were collected as part of a community needs assessment to inform the development of HIV prevention interventions in two contiguous counties in northeastern North Carolina, USA. We conducted eleven focus groups with three population groups: adolescents and young adults aged 16–24 (N = 38), adults over age 25 (N = 42), and formerly incarcerated individuals (N = 13). All focus groups were audio-recorded, transcribed and analyzed using a grounded theory approach to content analysis and a constant comparison method. Six major themes emerged from the discussions linking neighborhood context and adolescents sexual behavior: the overwhelming absence of recreational options for community members; lack of diverse leisure-time activities for adolescents; lack of recreational options for adolescents who are dating; adolescent access to inappropriate leisure time activities that promote multiple risk behaviors; limited safe environments for socializing; and cost-barriers to recreational activities for adolescents. In addition, lack of adequate parental supervision of adolescents’ time alone and with friends of the opposite sex, as well as ineffective community monitoring of adolescent social activities, were thought to create situations that promoted sexual and other risk behaviors. These findings allowed us to develop a conceptual model linking neighborhood structural and social organization factors to adolescent sexual behaviors and provided insights for developing interventions tailored to address local socioeconomic realities.