The current literatures on girls, queer youth, and multicultural education have ignored a significant group of young people and their experiences in school. This research is a retrospective exploratory study of masculine female adolescent schooling experiences, focusing on the school experiences of adults aged 18-54 who were socially defined as "girls" but who presented a masculine gender expression. This group of people, who may call themselves "tomboys," "butches," or "transgendered" are so underrepresented in the dominant discourses that there is no common language by which to categorize them. In interviews conducted over the past year, these participants revealed the transphobia, homophobia, and misogyny, as well as the support and freedoms they experienced within educational systems. This study reveals the need for critical examination of school policies and their impact on transgender youth. Further development of anti-oppressive curricula which address gender expression as a form of diversity is needed, as well as a better understanding by teachers of the complexity and multiplicity of gender expression. (Contains 2 notes.)