This chapter looks at Iurko Pokalchuk’s Ukrainian “foundational” pornographic fictions, which he sees as an essential genre for the Ukrainian literary process, and examines how his representations of sexuality are articulated through the dual discourse of erotic desire and transgression. The chapter focuses on a link between sexual transgression, the transgression of conventional discursive norms and regimes, the subversion of social values, and the disruption of commanded historical memory, all of which work against social and cultural fixities. It shows how Pokalchuk departs radically from totalitarian paradigms that are promoted persistently by socialist realist literature. In so doing, he is capable of invoking transgression through imbrication of the public and private discourses of power and pleasure, of politics and the erotic. Thus, transgression releases the sexual bodies blacked out by dominant Soviet ideologies, public morals, and self-censorship into the representational sphere.