This essay comprises an investigation of ekphrasis in the work of J. J. Winckelmann and particularly in his presentation of famous statues in the Vatican Belvedere courtyard collection. Key treatments of statues are revealed as offering much more than descriptions or art-historical analyses. Rather, they detail emerging relationships with works of art, relationships the dynamic nature of which is captured in the rhetoric of the descriptions. And like many good relationships these are informed by sex – but perhaps not in the obvious manner. It is more than a matter of Winckelmann taking a fancy to the objects he describes. Writing on art is revealed as an important site of repressed/submerged homosexuality. Following theoretical leads offered by Michel Foucault and Michael Worton, the essay investigates the disguised discursive existence of homosexuality in the rhetoric of aesthetics and explains its importance and subversive potential in a world where homosexuality cannot easily exist in the open; it then reflects upon the fact that in the apparently more liberated twentieth century, discussion of the sexual subtext to Winckelmann is still remarkable for its absence. Winckelmann is thus preserved in the literary/historical consciousness as the initiator of a rather arid brand of Neo- Classicism – all noble simplicity and calm grandeur – when his own writing reveals opposite, more human qualities.