Transsexuality is understood variously as a psycho-medical phenomenon, as an identity category, and as a postmodern challenge to notions of gender and identity. As transsexuality is discursively constituted through each of these frames of reference, different assertions are made about what transsexuality is. Each of these ontological statements carries different implications for "transsexuals". By employing queer and poststructuralist feminist critiques which unsettle "knowledge" about trans sexuality, this thesis becomes part of a wider project of exploring the crevices in the process of (normative) gendering. I work closely with transsexual and transgender texts to engage with political and theoretical issues arising out of specific attempts to define trans sexuality theoretically or to deploy the transsexual figure politically. Some of these texts are transcripts of taped interviews and a workshop conducted with transsexual and transgendered people in Aotearoa I New Zealand. I begin by introducing the thesis and situating it relative to other literatures on trans sexuality. I then offer a discussion of epistemological and methodological questions, and describe the research process. I critique psycho-medical definitions of "transsexuality" and then discuss critically debates among transgender theorists and activists. My analysis of the various diagnostic classifications of transsexuality highlights problematic ways in which transsexuals' erotic attractions have been constructed or overlooked. Through my discussion of trans sexuality as a case of being "trapped in the wrong body", I suggest ways in which both transgender and psycho-medical theorising could work more critically with understandings of transsexual embodiment. By engaging with selected transgender texts, I identify ways in which transgender theorising and political ventures could be strengthened: by opening up to theorising about the significatory importance of sex reassignment surgery, by negotiating carefully the inc1usivity (or exclusivity) of the term "transgender", and by challenging ethnocentricity in transgender theorising. I discuss contentious assumptions about the interactions between transgender theorising and queer theorising, emphasising the importance of developing theorising about "sexuality" and "gender" that does not become mired in the language and politics of identity. I present this thesis as a multi-vocal discussion of the ways in which trans sexuality is constructed within various clinical, academic, and political settings. Throughout the thesis I engage with "transgender theorising" - a recent body of political and analytic writing. This intersection of theorising and activism opens up discussion about the political implications of gender-crossing and the power dynamics in which transsexuals are imbricated on entering the psycho-medical arena. By engaging in this transdisciplinary discussion, I seek to open up possibilities for transgendered ways of being: possibilities that can no longer be defined through frameworks of diagnosis and disorder.