Bay City (pseudonym) is one of the nation's urban epicenters of the HIV epidemic. Although researchers have examined HIV risk behaviors among juvenile offenders detained in juvenile facilities, no study has examined these risk behaviors among youth offenders who have been waived to adult criminal court and detained in U.S. jails. In the present study, qualitative data were collected from 30 African American male youth (ages 15-17) detained at the Bay City Jail. These rich, descriptive narratives provide important insight into the HIV risk behaviors within this population.