Most efforts to promote gender equity in sub-Saharan Africa have been rooted in a Western heteronormative framework inherited from colonialism that aims at ‘balancing’ gender rather than deconstructing it. Dismantling this entrenched, though exogenous, binary is a daunting task, especially since, over time, it has become widely accepted as ‘authentically’ African, while the more radical initiatives of African trans* activists are seen as foreign. African trans* activism is theoretically sophisticated, deeply committed, and highly skilled, but its impact has been confined largely to an ‘Afropolitan’ elite. Based on interviews with leading trans* activists, this paper examines some of the key challenges to deconstructing the imported binary at grassroots levels. It looks at how linguistic and cultural particularities affect trans* activism in Africa and proposes new strategies, using lived cultures as a basis, that will be more appropriate and effective in a postcolonial context in which both indigenous and exogenous elements legitimately interact.