This article examines the poetry, prose, and rap lyrics written by nine low-income, African American and Latino urban youths. The study is based on a 3-year research project using ethnographic methods including field observations, informal interviews, and collection of written artifacts. Part of a larger study of these youths' writing practices, this article focuses on the ways that they use writing to negotiate gendered and sexual identities in complicated, sometimes conflicting, ways. The article is grounded in the field of new literacy studies, and the author argues that educators and other youth workers can find, in the writing of youths like those in the study, an entree into sometimes uncomfortable yet vitally important conversations about gender and sexuality. Through analysis of the writers' texts and conversations, the author models ways of drawing useful insights from such texts.