OZMA and/or My Lost Youth
Back in the late 1990s TGForum contributor Hebe Dotson wrote about a transgender plot twist in one of Frank L. Baum’s Oz books. The twist happens many chapters into The Marvelous Land of Oz. Some of the familiar characters are present and the action takes place after the Wizard has headed back to Kansas. Dorothy and Toto have also left Oz but the Tin Woodman and Scarecrow team up with a boy named Tip and a being Tip has accidentally created named Jack Pumpkinhead. Because his head is a pumpkin.