Transgressions aims to use poetry to explore the intersections of transgender and transitional identities in education spaces through the lenses of queer theory, literature studies, and autoethnography. I address the lack of representation of transgender voices and experiences in historical literature and poetry (the classroom content) in addition to my experiences in the classroom itself. The objective of this study is to use evocative methods that intentionally resist hegemonic expectations to highlight the importance of trans*poetry as an essential tool for self-reflection and identity formation and to point toward new methods for teaching writing that reflect the lived experiences of learners in the margins. The methods used in this study are autoethnographic and involve self-reflexive analysis of my own post-secondary academic experiences and literature-based analysis of my own poetry (written throughout my academic career). My study reveals insights into the nuanced experiences of the learner and educator in post-academic spaces, and the results of my research indicate that trans*poetry has the power to challenge dominant narratives; the power to ground, historicize, and contextualize self-narratives; and the power to create space for marginalized voices to be heard in and out of the classroom. In conclusion, Transgressions offers a new perspective and framework to study identity and history in post-secondary education spaces. It highlights the importance of experience and creative expression as sources of knowledge and understanding and proposes a new historiography that centers the voices and experiences of transgender people. While this study has its limitations, it is hoped that it will inspire further research into the intersections of poetic expression and self-identity in post-secondary classrooms.