Change is an inevitable part of life, more so for gender non-conforming students who have to confront prejudice and hostile environments as they transition from school to university. An understanding of the issues faced by first year students with diverse sexual and gender identities is important to ameliorate many of the challenges presented during this transition. This article examines how these youth negotiate and navigate the marked compulsory heteronormative university environments. We employed the concept of compulsory heteronormativity to reflect on assumptions of sexuality and gender identity construction as well as aspects of power and difference. A phenomenological research design was used in the study. Twelve gender non-conforming students participated in focus group discussions and individual in-depth interviews to relate their day-to-day experiences as they transition from school to university environment. The findings revealed that there are individual, institutional and structural factors that impede on the transitioning progress of gender non-conforming students from school to university in South Africa. Given these findings, we strongly recommend further research in the development and implementation of robust university transition programmes that are inclusive of students with diverse sexual and gender identities.