The narrative texts of contemporary Chilean writer-visual artists Pedro Lemebel and Francisco Casas use the theme of cross-dressing as a weapon to parody and criticize the value system which determines the process of identity formation, both individual and social. Employing the exuberant and ornamental language of the neobaroque style, these authors highlight in their urban chronicles and novels the problematic figure of the cross-dresser, an androgynous and transgressive Subject, in order to propose a new perspective toward the traditional categories of masculine / feminine, white / mixed, and Latin American / Western Culture. The use of linguistic artifice is associated with Simulation, an artistic and discursive technique employed as a mask that unmasks the conventionality of the categories which govern the patriarchal, Masculine-heterosexual Western society.