Is he, or isn’t he? Ambiguity and indeterminacy are powerful incitements to sexual interest for certain queer adventurers. The flamboyant and in-your-face faggot has undeniable charms; the unequivocally straight he-man is an attractive challenge; but the doubt that graces and gilds an uncertain target is a consummate come-on. For the queer reader, the enigmatic or polysemous text is a similar turn-on. Ambiguity is an invitation to approach, pursue, or persuade. This dissertation is a culmination of my encounters with sexual ambiguity in medieval literature. In my attempts to come to terms with negative representations of homoerotic desire or expression, I began a flirtation with certain texts that are usually understood to promulgate an unambiguous condemnation of same-sex erotic activity or attachment. My readings reveal these texts to be far-from-unequivocal. Their language is, itself, dubious, and insofar as language was analogized to sexual practices they are, themselves, sexually suspect. These texts present images that are open to multiple interpretation—often troublingly erotic. At the level of the word, these authors employ polysemy and dubiety that challenge a superficial understanding of their antisodomitical sense. My chapter on the Anglo-Saxon riddles of the Exeter Book explores how the obscene can be concealed in the commonplace. The riddle form is an elaborate type of metaphor or simile. My exploration of the mechanism at the gross level will prepare my reader for my more subtle suspicions of the sexual in later texts. Exploiting the ambiguity of Old English in his deliberately obscure descriptions, the poems invite readers to picture obscene action and objects as solutions to ostensibly benign enigmas. The unnamed is unmentionable, the unspoken, the unspeakable. My chapters on Peter Damian and Alain de Lille—and a preliminary excursus on exegetical practices (“A Monstration”)—demonstrate my queer interpretive method, recognizing in their use of polysemous Latin a potential for play and perversion. The anti-sodomitical texts embrace paradox and paronomasia—the potential for a word to signify multiple (sometimes contradictory) ideas simultaneously. Word-play enacts sex-play, and paronomasia, therefore, perpetrates paranomesis, transgressive conduct. The careful reader can discern an ambiguous attitude toward the topic both in what these texts say and the way in which it is said. These texts say one thing but hint at another. Rather than the oppressive polemics we imagined, the Liber Gomorrheanus and de Planctu Naturae become liberating paeans to the perverse or peculiar. My dissection of Chaucer’s pansified Pardoner lays bare a related phenomenon: How language and other signs may be adopted to obscure the patently obvious. Chaucer exploits the plasticity of Middle English to problematize the Pardoner’s predicatory (and predatory) practices. Despite all manner of misdirection, the anxious pilgrim’s constant insistence on corporal language and imagery always returns the reader to the source and site of sexual disgust: the Pardoner’s anomalous body. I figure wordplay as sex-play, fostered by the queer’s ambiguous relation to ambiguous speech. There is something in the nature of language—polysemy, plasticity—that speaks to the gay sensibility precariously situated at the margins of intelligibility or invisibility. My method combines the impulses of the eromenos (boy-lover) and the hermeneus (interpreter). This eromeneutics intends to encourage and equip like-minded readers to approach texts fearlessly. In flirting with these texts and their meanings, critics should consider the semantically tentative tempting. A queer interpretation informed by double consciousness delves the conscious doubleness of these texts. Through such tilling, the field of study becomes a playground.