The Slavery Abolition Act 1833, triggered a mass labour emigration between the years 1837 and 1917 from the Indian subcontinent to the Caribbean islands which prompted a “new system of slavery” in the form of the indentureship and became a potent mechanism in the formation of the Indo-Caribbean diaspora. Female indentees were encumbered with continuing Indian traditions and preserving a sense of Indianness through domestic enactments, culinary practices, and religious perpetuation across the kala pani. However, Indian women shattered the bigoted patriarchal confines to liberate womanhood in the foreign land with their jahaji-family and renewed sense of independence. Women suffered double marginalisation throughout indentureship and in the defining voyage where they silently agonised the loss of homeland, family, and culture but also formed lasting bond referred as jahaji-behen and acted as sisters, mothers, midwives, and allies to one another. The second largest ethnic population spread across the West Indies manifests a long history of Indo-Caribbean women’s struggle that acquired a primary status as a dialectical development for the globally progressing feminist thought. My discussions regarding gender/sex in the Caribbean will be defined by cultural crossings, diasporic cosmologies, identity reconstruction as well as binaries of traditions and transformations, myths and artefacts, and the sacred and the sexual. This chapter will emphasise the feminist navigations, domestic relations, and cultural and political engagements in Shani Mootoo’s Cereus Blooms at Night, Janice Shinebourne’s The Last English Plantation, Shiva Naipual’s The Chip-Chip Gatherers, Sam Selvon’s The Brighter Sun, Lakshmi Persaud’s Butterfly in the Wind and Daughters of the Empire.