Trans collegian research continues to grow, although focus on trans residents in campus housing environments warrants continued expansion. The reliance of university housing programs on assignments using the gender binary, even with attempts to be inclusive towards trans collegians, poses challenges and difficulties for trans collegians, with additional challenges for those transitioning. This article presents the narratives of two trans men transitioning during their first year of college in campus housing. The challenges but also possibilities for housing professionals to better support transitioning trans men and other trans collegians emerge from their stories.