Since the 17th century there has been a proliferation of discourse on sex and a host of sexual identities have been surfaced. One such sexuality that is particularly marginalised is transsexuality; central to which is the management of the transsexual self. The critical study of such practices has often been neglected in favour of ‘mainstream’ research on transsexuality’s deviance, aetiology and treatment. Furthermore, internet-based resources have been identified as a key site for the management of the transsexual self. Hence, this study aimed to investigate the constructions of transitioning in popular websites aimed at transsexuals and significant others, family, friends and allies of transgendered persons (SOFFAs). A search strategy was adapted to select the most popular websites for analysis. A discourse analysis – guided by Parker’s (1992) 20 ‘steps’ – was conducted on 12 webpages. The construction of transitioning was dominated by biomedicine and the ‘psy’ professions. Due to these hegemonic powers the transsexual identity was associated with distress and thus a number of technologies of self – particularly medical intervention – were ‘needed’ for the management of the transsexual self. This construction spoke to the rights and health of transsexuals but also appeared to limit their freedom and serve capitalist gain rather than the interests of trans persons. Uncovering these power dynamics may have important implications for the Standards of Care, the controversial status of gender identity disorder in the DSM and allowing for the creation of alternative power strategies which may permit more freedom in the care of the gendered self.