Lipstick And Heels

Ampersand points out this 2005 essay by Julia Serano:

Media depictions of trans women, whether they take the form of fictional characters or actual people, usually fall under one of two main archetypes: the “deceptive” transsexual or the “pathetic” transsexual. While characters of both models have an interest in achieving an ultrafeminine appearance, they differ in their abilities to pull it off. Because the “deceivers” successfully pass as women, they generally act as unexpected plot twists, or play the role of sexual predators who fool innocent straight guys into falling for “men.”