This thesis draws on 64 published life-stories of transsexuals to explore the structure and performance of gender in Western society. The concepts of “normal”, “natural”, or “ordinary”, gender are based on a set of largely unarticulated assumptions about the structure of gender, and how it is legitimated and maintained within a social context. The existence of transsexuals, as agents, challenges the “innocent” terms of occupation of the non-transsexed, and has given rise to a series of gatekeeping exercises to not only control and pathologise the transsexuals’ demands for re-embodiment, but also to control and constrain the transsexuals’ legitimacy as occupiers of gendered space. Transsexuals cause unease to the “normally” gendered, not so much because of the intrinsic pathology of their “condition”, but because of the structural and linguistic limitations of the existing model of engenderment. I have gained insights into “gender-in-the-ordinary” by studying how a frequently marginalised group, transsexuals, negotiate the existing gendered landscape, and how the non-transsexed occupiers of “the ordinary” police the borders of legitimacy. This study shows that the transsexual discourse has both led, and reacted to, existing understandings of engenderment. Having identified some of the limitations of these “understandings”, I re-mapped the gendered landscape with an aim of accommodating the transsexual narrative without resorting to pathologisation. My revised model of gender contains four distinct and quasi-independent states; an organically-based conviction of being gendered, an internal understanding of one’s legitimate place on the gender binary, a socially-validated state of engenderment, and a set of socially-sanctioned roles to affirm that legitimacy. While all four states are concordant in non-transsexuals, an inconsistency of these layers forms the substance of the transsexual condition. This thesis situates the transsexual narrative within other Western discourses on gender, by recognising a common goal of genderal legitimacy within a multi-layered gender landscape.