Since their first appearance in the 1990s, emoji and kaomoji have represented a tool to express and transmit messages in nonverbal ways. Their use has been increasing and developing over the past few years, especially thanks to the massive diffusion of new media and devices such as computers, smartphones, tablets, and freeware apps for instant communication (Line, WhatsApp, etc.). Emoji and kaomoji could be specifically interpreted as a new language, and especially in Japan, their use represents a current trend in social media and blogs. In this article, I investigate the use of emoji and kaomoji by professional dansō, 男装 (female-to-male crossdresser escorts), in their blogs and Twitter accounts. Crossdresser escort companies require every dansō to keep a weekly updated blog and a daily updated Twitter profile to communicate and share their life experiences and thoughts with (potential) customers and fans. I explain in which ways, and for what reasons, dansō use emoji and kaomoji in virtual interactions, relying on the outcomes of interviews conducted from September 2015 to July 2016 with 14 professional crossdresser escorts and through the examination of blog posts, tweets, and direct messages on LINE. Specifically, drawing upon Butler’s theory of gender performativity (1990), I argue that dansō perform1 their gender identity using (or avoiding the use of) emoji and kaomoji. I also compare their use of emoji and kaomoji on public profiles and in private conversations, to highlight the different gender negotiation required when interacting with customers or coworkers. Moreover, I highlight how emoji and kaomoji are used as tools to manage intimacy in relationships between crossdresser escorts and their customers.