In an historical and theoretical investigation of female enslavement in urban eighteenth century Barbados and South Carolina, I track the evolution of a female African diaspora in two colonial port cities and the tools they fashioned to survive the violent reality of New World slavery. Beginning with Barbados, I investigate the development of an enslaved female majority in an urban setting and the ways in which enslaved women were confined by and created space within this context. I argue that perceptions of gender and the African female were transplanted to the Carolinas from Barbados leading initially, to a similar system of female enslavement in work and confinement in the city of Charleston. With particular attention to the making of colonial cities, my discussion of Bridgetown, Barbados and Charleston, South Carolina, both major slave-trading ports, reveals the development of the institutionalization of a sex industry, involving female slave owners and enslaved women and the multiple roles an enslaved female could occupy within an urban context. Moreover, I examine confinement, literal and figurative, in both cities to interrogate the construction of criminality and the means and methods used to punish the enslaved female captive, in life and death. I contend that an analysis into the subjectivitics or experiences of enslaved women must be interdisciplinary and explicitly conscious of power in the production of History. Illuminating those who were the most powerless, my dissertation crosses geographical, temporal and cultural boundaries in an effort to deconstruct both race and gender.