rhythmia

Misfile is a web comic that I think kind of gets it right. The premise is that an incompetent angel accidentally messed up two people's lives by mixing up papers from their "files". One of the characters became two years younger, the other (Ash) goes from biologically male to female. One of the persistent themes is Ash's lack of comfort with suddenly being a woman, and his wondering whether certain behaviors (caused by the trials of high school life) are because his mind is becoming more girly or if his male self would have done the same thing.