This interdisciplinary study offers an exploration of the polysemy of the term “fiction,” as a possible tool which could contribute to conceptualizing the links and exchanges between Law and Literature. The starting point is the theory of fictions developed by Jeremy Bentham (1748–1832). Although Bentham early expressed his distrust of legal, religious and political fictions, he acknowledged the interest of logical fictions in the constitution of knowledge. Later thinkers like Hans Vaihinger and Michel Foucault further elaborated on the heuristic value of fictions. Could literary fiction too constitute a heuristic tool? The hypothesis is tested by looking at the way Bentham’s penal theory was reflected in late eighteenth-century Gothic and Victorian literary works, as well as the way his Principles of Penal Law and Panopticon letters rely on literary devices and the production of numerous scenarios. Reading Bentham’s writings alongside Gothic and sensation literature—with works by William Godwin, Charles Maturin, Ann Radcliffe, and Wilkie Collins—makes it possible to map out the points at which penal theory and literary discourse meet.