Undergraduate students training to become educators--unfamiliar with schooling and student populations beyond their alma mater--center on their own PK-12 milieu, rather than challenge their dispositions to acknowledge varied lived experiences. Their struggle to comprehend identity intersections can complicate diversity and social justice discussions in teacher preparation. Thus, pushing future teachers to better understand other lived experiences, as well as their own levels of privilege, is paramount in preparing them to effectively teach all populations. This article is an autoethnographic study of instructing teacher candidates (TCs) in a multicultural education course to investigate issues of transgender, gender non-conforming, and intersex communities--exploring literature, current events, and classroom discussions through poetic inquiry. Analysis of arts-based curriculum interwoven with TC-authored poetry demonstrates: (1) one course's evolving understanding of TCs' cisgender privilege; and (2) how privilege impacts TC interactions with gender non-conforming youth.