This chapter analyzes cultural representations of what Amalia Cabezas calls a transnational “economy of desire” as an important vehicle of socio-economic mobility for working-class Dominican women. Studying the photo series and personal account of a U.S. sex tourist, a short story by Dominican writer Aurora Arias, sex worker testimonies, and several recent films, the chapter enumerates the limits of nonwhite Dominican women’s engagements with, and manipulations of, this uneven transnational economy and questions the optimism behind individual and business philanthropy that takes for granted the larger world order, assuming equal access to global citizenship acquired and consolidated through consumer choices. This chapter proposes that what had been a unique territory within the Americas had become another “third world” island-nation providing cheap labor, sun, sex, and sand through the major socio-political and demographic shifts of the twentieth century, including the consolidation of the Dominican nation-state, U.S. imperialism, and transnational neoliberal policies.