This thesis examines the experimental film and video art by two Canadian moving image artists: James Diamond’s video Jizz Envy (2014) and Skyler Braeden Fox’s short film Hello Titty (2015). It argues that these works create spaces that enable a recategorization and rethinking of trans embodiment as part of a larger gender spectrum of possibilities than those offered in the current diagnostic definition of trans identity practiced in the medical field and propagated in society at large. It presents how by centering transmasculine sexuality, these artworks disrupt the logic of dysphoria at the heart of diagnostic discourse which assumes that trans individuals are incapable of pre-operative sexual intimacy. The thesis critiques the current model of diagnosis focused on dysphoria and the concept of the wrong body. Using José Esteban Muñoz’s theory of disidentification, it presents how these works weave between different conceptualizations of embodiment that can be simultaneously aligned with diagnosis and contradictory to its implied structure of trans identity. Finally, through discussion on BDSM practices, sex, and play within the works, it concludes that Diamond and Fox’s works explore and expose the antagonistic relationship between dysphoria and trans embodiment that each artist experiences, simultaneously upholding the concept of the wrong body and critiquing it.