This article explores schooling experiences of James, assigned-female-at-birth (AFAB) male, with a focus on his Catholic K-8 experience. James was caught in the tensions of school and home: Catholic school reinforcing traditional norms of gender and a family that bucked these norms. At school James learned about the body and sex, never feeling comfortable in his biological body or his assigned female gender; he did not want to menstruate and birth babies but wanted to grow a mustache and have his voice deepen. The purpose of this qualitative study, using narrative inquiry, was to understand the schooling experience of a transgender student, experiences influencing how they came to understand gender and identity. James' narrative is presented here as he emerged from school as one who: pushed against norms; engaged in inquiry through self-reliance; and longed for a different gender identity and biological self, gender and biological longing. These themes demonstrate the complexity of navigating through school while trying to understand one's gendered and, in James' case, his biological identity and self. Educators can learn how to support transgender youth and create educative lessons of gender through James' narrative.