To address the tension between public education norms and the lived experiences of racially marginalized students, this study examines how Brother to Sister (BTS), a community group, promotes sense of belonging and college access among Black high school students using the school as a primary dialogical space. Specifically, through qualitative assessment, this study interprets the pedagogy of Brother to Sister through narrative accounts of how the organization functioned in the lives of its members. As experienced by participants, BTS enacts culturally centered pedagogy and African-centered education to promote personal development and community enrichment outcomes.