Black adolescents, including Black immigrants living in the United States, experience a disproportionate burden of sexually transmitted infections (STIs), including HIV, which are linked to adolescents’ sexual decision making. Parent-child sex conversation is one effective strategy to aid adolescents in making responsible sexual decisions and reducing their sexual risk. Applying a theoretical framework, this qualitative study sought to characterize the perceptions, enablers, and nurturers of parent-child sex conversations among Afro-Caribbean families and their role in adolescent sexual development. The sample included 14 mother-adolescent dyads/triads (N = 31), recruited from four community-based organizations in MiamiDade County, Florida. Utilizing a narrative inquiry approach, researchers collected data on parent-child sex conversations within Haitian and Jamaican families. Thematic content analysis was used to generate themes and allowed for comparisons across groups. Positive perceptions of sex conversations were reported, yet families experienced frequent barriers to sex conversations, including discomfort and limited sexual health knowledge. Extended family and community members were identified as additional and alternate sex educators, often reinforcing common cultural sexual views such as abstinence. To promote healthy adolescent sexual development, Afro-Caribbean adolescents may benefit from parents, extended family, and community members acting as early interventionists, who can provide accurate and culturally appropriate sexual health messages to adolescents.