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This paper explores the relationship between sexuality and freedom by considering josou (male-to-female crossdressing) as a transgressive gender- and sexual-variant practice in contemporary Japan. Based on fieldwork in Tokyo’s josou scene, I will argue that individuals trouble social norms and enact alternative forms of belonging when they play with gender and interact with fellow crossdressers. Many josouko (crossdressers) regard josou as an accepted part of Japanese tradition, rejecting present-day gender and sexual norms adopted from Western culture. What therefore defines josou and what is freeing about the practice? This research rethinks gender and sexual diversity in Japan through josou culture.