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Guadeloupe and Martinique, the French Caribbean, are societies which were built in slavery and are based on a race, class and gender hierarchy. Matrifocality is known to be a singular family system that specifies those islands, and in which learning sexual and parental roles depends on a respectability/ reputation double rule, coming from the colonial period. This paper aims at demonstrating how a mother-headed education, the community social control and a widespread and castrating representation of slavery traditionally manage to prepare black boys to become lovers and runners much more than fathers or husbands. Actually, they are summoned to prove their virility, by showing their physical and sexual strength, while hiding their lack of social power. The paper also questions the contemporary evolutions of those manliness roles, as well as sex and gender new images, for example in rap culture and pornography videos.