Drawing from a life history study we examine memories and experience of schooling in Papua New Guinea among 45 trans women and sexuality diverse men. While participants reported regulating their expression of gender and sexuality to ‘fit in’ and avoid physical and verbal abuse at school, others felt able and supported to express their gender and sexuality diversity more freely beyond stereotypical norms. Schools provided a variety of experience for trans and sexuality diverse youth, unsupportive in many ways but supportive in others. The study highlights the importance of examining the impact of colonial discourses driving homophobia and transphobia in diverse settings, and understanding the socio-cultural climates of schools to identify solutions to the discrimination and violence experienced by trans women and sexuality diverse students. Further research into the current experiences of trans, gender and sexuality diverse young people in school would provide a valuable comparative perspective to our retrospective study.