Cuban journalist and diplomat Alfonso Hernández-Catá (born 24 June 1885 in Aldeadávila de la Ribera, Salamanca, Spain; died 8 November 1940 in Rio de Janeiro, Brazil) was a prolific cosmopolitan writer whose fiction is largely centered on the psychological, social, and political dimensions of human experience. In this dissertation, I analyze the stories of the male protagonists in two of his novels: Eulogio Valdés in La piel (1913; The Skin) and José-María Vélez-Gomara in El ángel de Sodoma (1928; The Angel of Sodom). I focus on how these characters, who struggle with “sexual and racial inversions,” such as gender dysphoria, homosexuality, and miscegenation, are allegorical portrayals of hegemonic discourses and practices on sex, gender, and race in transnational contexts from the turn of the nineteenth century to the twentieth. First, I demonstrate how Hernández-Catá symbolically employs inversion—in its general meaning of reversal—as a literary device in concert with other ones that denote opposition, such as irony and antithesis, in order to invert, and therefore, problematize the stigmatizing historical and social meanings of the masculine/feminine and white/black binaries of sexual and racial inversion. By doing so, Hernández-Catá revises the homogenizing binaries of modernity and the psychological fragmentation they caused within the modern subject in order to reveal how the progress and advancement of eugenics and sexual reform reproduced and failed to attend to the hegemonic flow of power and knowledge during neocolonialism. While modernity has been regarded as an era of progress and change, I contend that it has not resolved the uneven management of resources and capital during the neocolonial period and the socioeconomic disparities that it continues to create for the marginalized subject beyond Hernández-Catá’s time. Therefore, I propose transmodernity as an alternative sociohistorical paradigm that addresses how the globalization and the exclusion of the marginalized from the discourse of modern advancement has rearticulated and reoriented the skewed notion of progress of modernity in order to account for ethical concerns over the sexual and racial difference of the subaltern. I suggest that the trans in trans-modernity responds not only to the transness of inversion, but also to what Riley Snorton has referred to as the transitivity and transversality—as in the passing and crossing of two entities—of gender and blackness. As such, I argue that while La piel and El ángel de Sodoma are texts that reproduce discourses on racism and patriarchy, their protagonists resist and destabilize their hegemonic presuppositions in order to formulate their own response to the repressive and homogenizing forces of tradition and modernity. In this way, they find ways to exercise their agency and autonomy amidst the temporal, spatial, and embodied changes of the transness of their inversion, thus allowing Hernández-Catá’s texts to transform fixed meanings of subjectivity that continue to reappear in the present of a transmodern imaginary. Keywords: Alfonso Hernández-Catá, modernism, inversion, homosexuality, race, trans