This chapter focuses on the literary production and social context in Istanbul, which is the political heart of the empire as well as the center of literary production from the late fifteenth century onward. It examines recent critical approaches to same-sex eroticism in Ottoman literature. The chapter describes homoerotic examples in early modern poetry to uncover commonly used homoerotic patterns. The understanding of homosexuality as an innate perversion and an immoral practice in the nineteenth century transformed the societal norms and literary representations in late Ottoman culture and continued to develop as the society strove to modernize and Westernize. The dildo woman becomes the very manifestation of the possibility of female-female penetrative sex. The deployment of the Western-originated identity categories of gay, lesbian, or homosexual to refer to non-Western queers may lead to the latter's exclusion and oppression as Westernized, immoral perverts by the state and some other political groups.