This research paper focuses on ethnographic fieldwork to understand the logic of action and representations specific to Japanese men who deploy virtual female characters, notably called babiniku, for the purpose of creating entertainment content. The logic of babiniku comparisons with Japanese theatre is explored to demonstrate that portraying oneself as a "cute girl" (bishōjo) character is a tactic for defining oneself against dominant norms and developing an alternative model of identification for men. By researching virtual crossdressing practices, this paper attempts to shine a light on the contemporary issues connected to technology in Japan.