This essay explores some of the ways people conceived of the relationship between sexed bodies and gendered roles during the slow transition from the Ming (1368-1644) to the Qing dynasty (1644-1911). This was a period of increasing commercialization and significant challenges to traditional Confucian thought, one reflected in the work of the prolific author and cultural entrepreneur Li Yu (1611-80). Given his imbrication in both traditional networks of elite men and in the increasingly important realm of the market economy, Li Yu provides a useful entry point into the analysis of transgender representations in early modern China. Li Yu’s works demonstrate that the representation and performance of ambiguous or trans genders was linked to elite male consumption: that is, transgressive gender presentations were a prime form of entertainment, in fiction as in theater. However, his representation of nonnormative gender presentation also evidences a significant reconfiguring of conceptions of the body, the self, and the family in a world in which money was increasingly able to purchase anything. The author shows that during this tumultuous period, in which men and women grappled with questions of allegiance to the fallen Ming or the foreign Qing, the intersection between fungible currency and the gendered body emerged as a primary locus of elite male experimentation, in life and in literature, with the seemingly boundless possibilities of novelty and the purchasing power of silver.