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Between 1500 and 1600, Portuguese ships carried 154,191 men, women and children to the shores of Portugal and South America via the transatlantic slave trade. This harrowing passage, known as the “commerce in human flesh and blood,” was the result of sea routes newly forged by Portuguese sea captains and their African assistants (or grumetes). On the early waterways of the coastal Upper Guinea and Senegambia, these early African cosmopolitans, both free and enslaved, fulfilled demand for skilled maritime labor in the service of this accelerating commercialization. As native assistants, they worked alongside captains to navigate vessels, provide interpretation of local languages and act as intermediaries to local potentates selling slaves. As one early seafarer, Alvise da Cadamosto, explained, every ship carried an interpreter brought from Portugal “who had been sold by the lords of Senegal to the first Portuguese to discover this land of the blacks. They were often locally recruited from elite families or hired out by their Portuguese owners, if enslaved. Hailing from Lebou, Niominka, Papel, and Biafada ethnic groups, their maritime expertise marked them as unique bondsmen in the early Atlantic world. In stark contrast to the skilled men who circulated in and out of Portuguese coastal settlements in West Africa and Portuguese vessels, were young women traded or gifted by local rulers to ostensibly perform domestic and sexual labor. This presentation explores the early gendered dynamics of early Portuguese experiences on the West African coast, particularly the sexual division of labor in hybrid maritime spaces and the increasing sense of the distinct commercial value of enslaved men and women.