Considered one of the most controversial phenomena produced by the processes of economic globalization, the expansion of the sex industry and the radical shift in its composition and organization have received much attention in the last two decades, both academic and political. My research aims to interrogate the largely unexplored transformations that have affected the urban geography of prostitution and the evolution of local regulatory systems. In the context of a metamorphosis of the local sex markets, coincided with the accelerated growth of international women’s migration from the last decades of the century, these pages present an original empirical study on the relationship between prostitution, communities and local authorities in the major cities of the Italian region of northeast: the Emilia-Romagna. The survey focuses on street prostitution and observes three processes that in the last twenty years contribute to the crisis of the existing ones and the production of new urban regulation of sex work: 1) the settlement of migrant prostitution in the geography of territory; 2) the impact of spatial configurations of street prostitution on the communities; 3) the institutional mediation carried out by the local policy makers (first of all the Majors) on the effects of globalization of the sex market in the urban context. The comparison between cities is based on the hypothesis that the geopolitical dynamics between the different territorial systems operate as an organizing principle in the production of specific rules and practices on the prostitution issue.