While there have been a few isolated studies that touch upon urbanization, development of modern fiction, and contested configurations of public morality, there have been no serious scholarly work which puts the above mentioned concepts into conversation to one another. However, a careful historiographical study, allows one to witness a congenital intimacy between the unfolding of novel as a literary genre, rapid growth of urban sites, and constant reconfigurations of public morality in early 20th century Iran. Putting prostitution-as a mediating site- at the center of historical and literary inquiry this paper engages with contesting arrangements of concrete and metaphoric spaces of pleasure and pain and the slippery boundaries of moral space. During the Pahlavi period (1925-1979) Tehran became the site of rigorous urbanization, reformist will, and intense moral concern. Radical urban transformations during this time facilitated a public space that exhibited that which previously belonged to the private space, i.e. woman. Concurrently the category of woman became the emblematic and productive site of moralizing, reformist, and progressive will, as well as the failure of this will. This double sidedness of the category of woman gave birth to the emergence of the image of the prostitute as the “plague” of modernity. The gap between the two sides was maintained and reified through concrete compartmentalization of urban space of Tehran. In 1950s walls were erected around the red light district, first constructed in 1920s, making it a place of containment, to prevent prostitutes from leaking back into the city site. By this time, the red light district was referred to as the “District of Sorrow” (Mahhali`i Gham), perceived as the paradoxical space of pleasure and pain, and joy and sorrow. The modern(ist) urban space and novel as a literary form come to being at about the same time. Novels as modern fiction particularly portray the complexity of urban city life in exuberant prose. Delving into such novels, this paper argues that the double-side space of pleasure and pain eventually leaked back into the city, constantly (de)territorializing the moral public space. It takes as its point of departure, the concrete formation and failure of the “District of Sorrow” together with the cartography of prostitution in novels of the time as a window to the ways in which, the space of pleasure and pain is compartmentalized and mapped in relation to the constantly shifting space of morality.