Writing is a powerful communication tool. It affords the opportunity for creative expression and the analysis of comprehensive thought. This monograph describes the authentic writing experiences of three African American adolescent members of an after-school writing club situated in a boarding school. Without the constraints imposed by deadlines, rubrics, grading, teacher feedback, or test-centered, argumentative compositions, members of the club participated in eleven writing sessions where they co-constructed meaningful dialogue, wrote original manuscripts, and developed a supportive social community. The sociocultural context of these adolescents’ experiences with writing presents themes of choice, collaboration, creativity, and catharsis told in a series of dynamic narratives.