Some of these scenarios are the stuff of dreams, then again something like those awful unrealistic clichés from Petticoat Discipline Quarterly
There were a few instances from my childhood where a slight bit of half-hearted crossdressing was just playful... anything other than playful and my parents surely wouldn't let it happen. I had a subversive overly-sexual milf of a neighbour that on occasoin called me "pretty". Once on halloween she recommended I dress as a girl and that she would sort me out. I'm sure if I went through with her offer it would have been full on... and appropriately horrifying for me as it was halloween!
