The African presence in the United States and the construction of American black identity has a history of being sexualized. From this perspective, writing about racialization has often meant writing about sexual relations. Increasingly, scholars have drawn attention not simply to the sexualization of the black body, but also to the historical construction of sexual desire in the writings of African Americans. This chapter explores the representation of same-sex desire as well as the emergence of transgressive ideas about sexuality in these writings. It considers African American writing and cultural expression from the antebellum period until 1930. The chapter outlines the significance of representations of nonnormative sexuality in African American expressive culture that become the context for late twentieth-century works by self-identified gay and lesbian artists. Critical treatments have consistently shown that the logic of enslavement was perverse not simply in the abuse and misuses of power but in the sexual dynamics it encouraged and even required.