Until recently, the kala pani or “dark waters” navigated by Indian subjects indentured and shipped to locations in the Caribbean remained largely unexplored. In the past decade, the fiction of authors such as Ramabai Espinet and Shani Mootoo, as well as scholarship by Brinda Mehta, Shalini Puri, M. Jacqui Alexander, and others, has begun to excavate Indo-Caribbean experience as well as to chart paths from places such as Trinidad to locations in the North, especially Canada. In considering issues of citizenship and belonging, texts by Espinet and Mootoo offer insights into both the enduring borders that attempt to shore up norms of gender and sexuality and the ways that non-conforming subjects may build bridges to more inclusive concepts of citizenship. This essay discusses Espinet’s The Swinging Bridge (2003) and Mootoo’s novel Valmiki’s Daughter (2008) through the lens of transgressive sexualities that seek spaces of belonging beyond the dark seas of normativity and taboo. In both texts, lies and repression mark the lives of Indo-Caribbean men who desire other men. Both texts emphasize spatial arrangements, specifically houses and property in Trinidad, to examine issues of territory, citizenship, and nation for Indo-Caribbean subjects and to challenge borders that maintain normative identities as they label “perverse” and “unnatural” those whose desires blur such boundaries. In particular, women who desire other women, as seen in Mootoo’s novel, pose a powerful challenge to established order and prescribed roles. The essay explores the transgressive potential of such rebellions, which aim to cross and blur identities of race and gender as well as sexuality. Further, the essay addresses the following questions: If belonging necessitates a lack of freedom, what does free choice entail? What stepping stones might form the bridge to full citizenship?