Black men and boys have been constructed as libidinous threats to white womanhood and white racial purity since the sixteenth century. In the wake of the landmark "Brown" decision, white citizens fused the Black male rapist trope with segregation theology to create private segregation academies to minimize Black-white contact. These schools remain more segregated than traditional public schools. The participants in this study were recruited to a private Catholic high school where the entire Black population was made up of Black boys who played a sport and whose interracial relationships with white girls triggered resistance. Drawing from qualitative data, the purpose of this paper is to highlight five Black boys' experiences with phallic-based Negrophobia in a predominantly white and private Catholic high school. Findings reveal that participants realized they were transgressing institutional boundaries to preserve a racial order, and their transgressions were constantly policed and monitored.