The thesis examines how the fantastic as a literary mode may offer imaginative possibilities for expressing dissident sexualities and gender, via an author study of Jeanette Winterson. The study concentrates on the potentially subversive nature of the literary fantastic as a critique of culturally dominant notions of reality and in a close reading of Winterson's texts the thesis explores fantastic figurations of dissident genders and sexualities; thematic and structural convergences between the psychoanalytic category of the 'uncanny' and the 'queer'; and Winterson's efficient use of the fantastic mode in writing a historiographic metafiction of deviant sexuality.