Following the proclamation of the Second Constitution in 1908 and then the countercoup of 1909, the former guards of the harem, the African eunuchs, lost their jobs and became more visible in daily life in Istanbul. The curiosity about their private, post-harem lives became the topic of a 1914 novel, Wedding Night: The Lovemaking of A Eunuch. Belonging to a body of erotic literature published under suggestive titles yet with rather punitive plot lines that became popular in early 20th century, Wedding Night, in an unprecedented way, focuses on Ethiopian Amber Aga as he tries to settle in his post-harem life with a concubine at home and a soon-to-be wife. Amber is immediately marked by his Ottoman Muslim male neighbors as an outsider for his geographical origins, color, and sexuality, particularities that gave eunuchs their liminality and authority to monitor the sexual life in the harem. Outside the confines of the palace and in a society with pre-drawn boundaries, however, Amber’s ambiguous sexuality creates confusion and anxiety, one that quickly turns into an anxiety over masculinity and loss of imperial power that marked Ottoman fictional texts since 19th century. In this paper I will discuss how imperial masculinity redefined and eroticized over the body of an African eunuch and how the eunuch in the early 20th century context replaces the dandy, the effeminate fop of the Tanzimat novels, the embodiment of political and sexual anxieties.