This present study explores transvestitism and gender identification in cosplay behaviors. Drawing on the perspectives of textual poaching and gender performance, it asks whether transvestitism merely a temporary gender transgression, or a specific tactics aiming to dismantle the compulsory categorization of sex inherent in the gendered socio-culture. Based on semi-structured interviews, the author finds cosplay transvestites have to follow in-group rules which tend to echo mainstream gender values. The imaginary space deriving from transvestitism, however, does play an important role in the process of (male) cosplay transvestites' gender identification, as multiple or flexible gender values could be encouraged and introduced in real life. As conclusion, the author suggests further examination for probing the degree to which gender politics is implied in cosplay behaviors.