In Walter Pater’s work there are often mentions of discipline and ascesis in an explicitly positive way. But, in some of his work, discipline, although not ascesis, seem to be taking on a more negative form. Critics have nonetheless seemed satisfied with Pater’s explicit praise for discipline and the area is thus not very thoroughly researched. One area that is well researched is the homoerotic subtexts that are evident in a lot of Pater’s work, which critics have examined in a variety of different ways. I suggest analysing the imaginary portraits “Emerald Uthwart” and “Apollo in Picardy,” to argue that Pater contrasts the Ancient Greek notion of ascesis with the nineteenth century understanding of discipline in order to question the legal restrictions on homosexuality in late nineteenth century England. Due to the historical context of the 1885 Criminal Law Amendment Act, which criminalised homosexuality, and Pater’s regular use of—as well as his admiration for—Ancient Greece, I have found that there is a connection between discipline, ascesis, and homosexuality. In the essay I make use of some of Foucault’s theories, especially from The History of Sexuality Vol. 1 and Vol. 2., to argue that the juxtaposition between homosexuality and discipline and ascesis in the two portraits provides new insights to the intricacies of Pater’s work. Keywords: Walter Pater; discipline; ascesis; homosexuality; “Apollo in Picardy”; “Emerald Uthwart”; Imaginary Portraits