This article employs Lacan’s notion of anamorphosis, and the retrospection which Kathryn Bond Stockton presents as fundamental to the assumption of queer identity, as it demonstrates the functions and value of transgender readings of medieval texts. The article analyses two thirteenth-century literary works, Le Roman de Saint Fanuel and Aucassin et Nicolette, both of which feature pregnant male characters, alongside A.K. Summers’ 2014 graphic novel, Pregnant Butch. This juxtaposition reveals the resonances between these medieval and modern portrayals of gender non-conformity, as well as the highly gendered cultural norms surrounding pregnancy. Finally, attention to Janice Raymond’s transmisogynistic claims about the “rebirth” of trans women illustrates the importance of an awareness of transgender history.