This thesis interrogates denotations and connotations the signifier ‘homosexual’ has had on like-kind desiring men and their desiring; howtheir identities have culturally and psychoanalytically been subject-ed/ structured by/around/through this signifier. Unlike other texts’ attention to the history of the ‘homosexual’ as a personage, this thesis attends more pointedly to the cultural contingencies, most especially Freudian psychoanalytic discourse, which initiated and propagated this signification ‘homo-sexual’ over other possible terms and discourses. This thesis explores within three subjective epochs how homo-sexual signification, came to represent and be performed within cultural practices: the fin de siècle nativity of psychoanalysis; the Lacanian post-war world theorisations of desire and language; and the contemporary enactments of homo-sexuality within an increasingly porn-informed and subjected sexual discourse.