This critical text proposes new ways of conceptualizing Black womanhood by challenging plantation patriarchal culture and its binary constructions, and methods of Black heterosexual coupling. Black Women’s performances of womanhood are understood from juxtapositions with white idealism, resulting in Black womanhood explained negatively or for what it is not, rather than positively and expansively for what it is and could be. This book contextualizes Black womanhood as it was shaped by historical experiences of plantation, trauma, survival and most importantly, triumph. Myrie Obi expands upon her theory of butch heterosexuality, which identifies elements of gender presentation commonly marked as masculine. Using Jack Halberstam’s essential work of queer theory, “Female Masculinity” as a point of departure, Myrie Obi uses the Commonwealth Caribbean as a site of new inquiry. Butch heterosexuality challenges the patriarchal gender binary and encourages an understanding of sexuality and gender performance as distinct, arguing against a conflation of female masculinity and lesbianism. The result is an alternative way to start conversations about decolonial approaches to understanding (Caribbean) Black women, Black sexuality and Black gender performances. This book is critical reading for scholar activists and students in the areas of Black or Caribbean studies, Black sexualities and gender studies, sociology, social work, politics, gender justice and social justice courses.