If I'm not mistaken, if you go to the town mansion and look through things (stealing included) you will have a fight with the witch inside and if you lose, she will cast a curse on one of them and turn you into a woman
Well, the character sheet says that he turned into a she, being female, so I believe he did turn into a woman. Besides that, I literally only reset when I got that curse, so I can't really confirm that what you're asking for happened.
