This dissertation is concerned with the works written by the American novelist Thomas Pynchon while he was in his twenties. As such it deals with some of the short stories he produced as a student at Cornell, and with his first two novels, <i>V.</i> and <i>The Crying of Lot 49</i>. It excludes his longest and probably greatest novel, <i>Gravity's Rainbow</i>, partly because the earlier work deserves more attention than it has received, partly because it is difficult to confine a discussion of a text of such size and complexity to a single chapter. The Introduction is an exposition of the method of the dissertation, which draws on a distinction between the 'first story' or narrative level of the texts, and the 'second story', a latent structure concealed beneath the surface. Motives, techniques and problems involved in the construction of such latent structures are discussed, and brief examples are given. Ch. 1 is a close reading of three short stories, rather than a comprehensive account of Pynchon's career as a short story writer. It considers in turn <i>Mortality and Mercy in Vienna</i>, <i>Low-lands</i> and <i>Entropy</i>, all three set in Washington or New York in the late 1950s. In each case analysis reveals levels of meaning - artistic, political, psychological - which the anecdotal and apparently casual quality of the writing would not lead one to suspect. Ch. 2, devoted to <i>V.</i>, is concerned entirely with eliciting information from the subtext of the novel on the position it assigns to itself in literary tradition. The chapter consists of two sections, the first listing the more obvious allusions to 20th century literature in the foreign half of <i>V.</i>; the second inferring a critique of Modernism from these allusions. Ch. 3 opens with a reading of the 'first story' of <i>The Crying of Lot 49</i> which detects subtle indications in the text of negligence on the part of the heroine, Oedipa Maas. This reading then becomes the basis of an analysis of the 'second story' which suggests a concordance between the text's implicit conception of literary history and its political vision.