Scholarship on David Foster Wallace understandably tends to focus on addiction in his novel Infinite Jest, as well as on his stated desire for a literary movement that transcends the recursive, ironic loop of the postmodern. This essay, however, explores issues of trauma and perversion in Wallace's fiction – primarily beginning with Infinite Jest, chronologically speaking – demonstrating Wallace's concern with the freedom of choice. A palpable friction exists between conservatism and sexual taboos, and this friction characterizes much, if not most, of Wallace's fictional oeuvre. A principally psychoanalytic reading of the sexual elements at play in Infinite Jest, as well as in several stories from Brief Interviews with Hideous Men and Oblivion, cultivates a more thorough understanding of the addiction theme present in his work.