Stills from the very first pornographic movie to be released featuring a trans man, Transsexual Trouble (1991), directed by Gino Colbert and released by Cinderella. You can purchase or stream the full movie here.
Transsexual Trouble is told from the point of view of a cis male family therapist, who describes his therapeutic relationship with the Boner family, starting with Lulu who “takes after” her trans woman mother, Cindy. Les Nichols plays Cindy’s husband, Harry Boner. Les appears in a consensual non-consent femdom scene with actress Tasha Voux, who verbally degrades him, plays with his t-cock, sits on his face and rides his phallo-cock. The movie was released in 1991, a year before the release of Linda/Les and Annie: The First F2M Transsexual Love Story.