In this talk, I consider the work transformismo masculino (drag king performance) is doing during a time of social and economic transformation in post-socialist Cuba. Over the past ten years, Cuba has witnessed the growth of a private economic sector dependent on tourism and the unfolding of a so-called “sexual revolution” aimed at combating homophobia and transphobia. Both of these reform movements have been criticized, however, for the lack of material gains experienced by women and Afrodescendants on the island. In response, some independent projects have emerged that draw on histories of Afrofeminist and antiracist critique in Cuba to elaborate an Afroqueer social vision for the future. I examine the performances of Havana’s transformistas masculinas (drag kings) in this context to discuss how they critique normative masculinity, create space for Black lesbian women, and promote dignity for ordinary Cubans. This work, along with the broader Afroqueer movement of which it is a part, resonates with related artist-activism throughout the hemisphere that imagines social possibilities that go beyond the well-documented alliances between neoliberalism and LGBT rights.