This essay anticipates twentieth-century arguments about the production of the ideal transgender subject as those who are harbingers of an extractive ethnonationalism and have a right to transnational mobility. In looking at Olive Schreiner’s The Story of an African Farm (1883), this essay frames the white English settler and landowner Gregory Rose as a proto-transwoman. Gregory’s seamless gender-passing, to the point that they can move across national boundaries with ease, without declaring their citizenship, while still maintaining private property elsewhere, throws into relief the mobility of whiteness and the immobility of Blackness and Brownness within the Transvaal, and South Africa more broadly. Such a narrative of white settler womanhood imbricates the prototranswoman in the exacting of colonial land dispossession. The proto-transgender settler subject’s privilege of passing, both in gender presentation and across geographical borders, is predicated on the dissolution of Native African customary land law and the exacerbated surveillance of indentured laborers of Asian descent under legislative acts called “pass laws.”