Bad Boy to Good Girl

This is a broad category of T* fiction because the category only describes the outcome and not the means by which the transformation is achieved, which could for example involve magic. A common theme is punishment: a despairing mother subjects her rebellious son to “petticoat punishment”, the theory being that he won’t keep on acting out because he’s been left in a very vulnerable situation, perhaps with his male clothing taken away. Through humiliation, the bad boy is made to change his ways. If he doesn’t become a sissy, he becomes a ‘good girl’, typically the daughter that his female relatives wish he could have been: sweet and demure. Surgery and hormones are often mentioned in the closing stages of the story.

The conversion from bad boy to good girl may take place in the home (a relatively mild form, where the boy attends school in his usual attire but is forced to change when at home), the project might also involve his school life, or in extremis he might be sent away to a ‘special’ school. In this last case, some stories include elements such as brainwashing and hypnosis to bring about the desired behaviour.

In the wild (outside of T* fiction) there are very few examples of “petticoating”, although there was the 19th century practice of dressing young boys in skirts and dresses – largely for practical reasons in terms of changing a diaper in the time before zips and velcro.

Stories about wayward sons and nephews who get turned into sweet daughters and nieces abound at both Fictionmania and BigCloset.