This paper investigates perceptions of courtesans, gender and power from various perspectives, using both literary and non-literary sources and reconstructed lost books. Analysis focuses on representations of the celebrated courtesan, poet and painter Xue Susu (fl. 1575-before 1652) by writers of different backgrounds, gender and class. In late Ming times women participated in elite culture in unprecedented numbers. Courtesans gained prominence in the literati arts, playing a formative role in shaping cultural ideals. Late imperial Chinese discourse embeds the image of the courtesan in the formation of new beauty ideals and social negotiations of gender roles and power. Paradoxes abound, linking the courtesan with notions of chivalry, chastity and loyalism and depicting her in the context of national politics and warfare. The Ming/Qing texts reflect not only current perceptions of women and courtesans, but also the social and cultural aspirations, dreams, anxieties and desires of their authors.