This study investigates how transfeminine crossplay—imagined or enacted crossdressing as feminine characters from anime and manga—offers aesthetic resources for genderqueer experimentation. We situate this investigation in Singapore, an Asian sociopolitical context which privileges social harmony and penalizes vocal dissent. Through interviews with six crossplay fans (some identifying as transgender but not others), we unpack how they harness aesthetics in crossplay to negotiate genderqueer trajectories. Crossplay aesthetics clarified gendered feelings and prospective gendered futures. It created gendered-aesthetic styles, forming new trajectories. But for some, it counterproductively constricted gender experimentation's inventiveness. We argue that aesthetic play constitutes a holding space to silently cultivate gender nonconformity, sidestepping Singapore society's demonization of dissent. By momentarily suspending ties to futural demands of gender identities, crossplay installs a sense of atemporality within gendered aesthetics, encouraging fans to engage gender as aesthetic considerations dissociated from personal and social histories of shame, suffering, and discrimination.

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