This thesis uncovers and historicizes an overlooked aspect of America’s transgender history. The heterosexual male cross-dressers, or transvestites, of mid-century America constituted a group of individuals that espoused a particular discourse of respectability in their cross-gender practices, conceptualized unique bi-gender identities, and cultivated a community. Heterosexual male cross-dressers, under the leadership of Virginia Prince and Ariadne Kane worked to separate themselves from broader, and more recognizable, identities such as gay transvestites, drag queens, and homosexuals in an effort to define themselves as respectable. A critical historical analysis of Fantasia Fair indicates that Prince and Kane were not alone in their desire for a community of their peers, with whom to share ideas about sexological theories, personal stories, and tactics for self-preservation. As a direct response to the pervasive nature of transsexual narratives in the field of transgender history, this project demonstrates the important advances made by heterosexual male cross-dressers to our modern understanding of trans diversity. These cross-dressing narratives prompt historians of transgender phenomena to think critically about the diversity of identity categories that are encompassed in our present understanding of the term ‘transgender’. / Graduate / 2019-07-30