We collected narratives from five undergraduates who identified as either in the process of or had formerly transitioned from one gender to another while enrolled in a postsecondary institution. We used a narrative life story protocol to explore the greater context of participants as individuals. Participant stories focused on: the importance of relationships including roommates, friends, romantic partners, and role models; their experiences during enrollment, and institutional structures such as campus environments, faculty, and staff. We found the presence of health services focused on trans students' needs and a trans-specific student organization contributed to perceptions of an affirming campus. We also found that gender binary norms still impacted participants through their struggle to align with cisnormative practices. Implications for higher education educators and administrators include proper training of faculty and staff on trans issues and the need to systemically address practices and policies rooted in the gender binary.