ABSTRACT This article explores the schooling experiences of 12 fa’afāfine and fakaleiti who attended an all-boys faith-based secondary school in Aotearoa-New Zealand. Fa’afāfine are Samoan, and fakaleiti Tongans who are assigned male at birth, but enact varying degrees and types of behaviour deemed as feminine. There are currently no in-depth qualitative studies that examine the schooling experiences of these young people. Within the existing literature the experiences of fa’afāfine and fakaleiti are typically subsumed under the umbrella of transgender and/or non-binary students. This study examines participants’ recollections of daily experiences of being fa’afāfine and fakaleiti at an all-boys school where any expression of femininity was frequently disallowed and denigrated. In this highly masculinised environment, participants describe the struggle to be ‘like-women’ and the cisgender discrimination they faced. Incidents of bullying, physical assault and marginalisation from teachers and students along with the pathologisation and erasure of their identities within school curricula and practices were daily occurrences. These accounts contribute to an emerging and broader picture of schools as cisgender spaces, in which educational structures and processes reinforce the idea there are only two genders, and that gender is based on sex assigned at birth.