This article considers the ways in which pedagogy is formally represented in trans masculine porn, specifically in three films that stage scenes of learning: Linda/Les and Annie: A Female-to-Male Transsexual Love Story, Phineas Slipped, and Sex Education. Focusing on pedagogical scenes that dramatize failure, the article asks, Why, in trans porn, do we see extrageneric claims to educate? What kinds of pedagogical fantasies do trans porn, and porn-adjacent film, render about bodies and pleasures? The author offers a close reading of these films as rooted not in pornographic fantasy but in the fantasies of pedagogy. By directly incorporating pedagogy into the formal content of trans masculine porn films, these films distance themselves from the pedagogical functions of porn—porn as encounter, porn as learning about trans “difference”—and instead point to fantasies of efficacious pedagogy. The author suggests that these films do more than educate viewers on transgender; rather, they portray the pedagogical encounter itself as one way in which performers work through their own fantasies of successful pedagogy.