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Realizing the constructed nature of gender is often described as a twentieth-century Western phenomenon. Nevertheless, in several South Asian religious traditions, practitioners are instructed through songs and oral teachings to exchange and ultimately transcend gender identities. In this article I discuss the practices aimed at transcending gender identity among some contemporary Bengali lineages that have been defined as "heterodox" by nineteenth-century reformers. Several lineages in West Bengal and Bangladesh perform cross-dressing and meditative identification with the opposite sex. I discuss such practices using songs, riddles, and oral sources collected during fieldwork conducted between 2011 and 2015. I then briefly trace the history of religious transvestism in South Asian literature, while contextualizing this practice within Vaishnava and Sufi traditions. Finally, I discuss how similar phenomena have been interpreted by modern and postmodern scholarship to conclude with a conceptual framework for interpreting "pregnant males" and "barren mothers" in light of contemporary gender theories, with reference to performativity and ritual liminality. [ABSTRACT FROM AUTHOR]