Drawing on Butler's theory of gender performativity, which conceptualizes the discursive production of the gendered subject and the corresponding “constitutive instabilities” of such reiterative practices, I provide an empirical sociological examination of how individuals negotiate potentially unintelligible identities in their daily lives and the extent to which these practices call into question the conceptual dichotomization of stability and fluidity. While transsexed bodies, histories, and identities may “exceed” the limits of intelligibility, trans individuals are engaged in the process of meaning making—creating coherence both for themselves and for others. The present theorizing of (trans)gender identification has not fully explored the interaction among social expectations, individuals' attempts to be credible, and the structural limitations on intelligible gender identifications. In addition, despite theoretical arguments resting on the compulsory, regulatory nature of gender regimes, gender fluidity is often situated as counter to such regulation. By exploring the negotiated identifications of transsexed respondents across different interactional spaces and the structural rules and norms which frame such presentation choices, this article theorizes the contextual regulation of (trans)gender diversity and the corresponding production of situated identification. Further, in examining this negotiation, the concept of fluidity is interrogated in order to complicate the analytic dualism of fluidity/stability and the corresponding dichotomous positioning of transsexed individuals as either blurring or reifying the boundaries of the gender binary.