This article presents a tool of literary analysis developed by the author as an alternative to existing possible world theories (PWT). The aim is to create links between the latter’s neutral, descriptive accuracy and more value-laden approaches with an eye to both research and education. Establishing such links demands careful monitoring to prevent the tool from becoming arbitrary. This is done by (1) showing the steps that lead from common versions of PWT to this tool of analysis; (2) building control mechanisms into the tool, above all by keeping in touch with the original semantic modalities of PWT and reflecting on the use of the tool (“metacognition”); and (3) systematizing reader expectations, as the tool’s orientation toward value makes it cognitive. To show how the tool fares under such conditions and how it could play a role in education, it is then applied to the children’s books Where the Wild Things Are and The Gruffalo and the comic “The Baba Yaga” (from the Hellboy series): they all undergo a process of analysis and metacognitive reflection. Validating the tool as an analytic and an educational measure depends on its ability to guide the reader toward an interpretation of these texts and to handle interpretative lacunae through metacognitive inquiry.