Any wild, crazy, kinky cross dresser stories?

Answer 1

I was at this Rave at a total knock-out blonde asked me to hold her jacket while she danced. I did even though I was confused because noone had ever asked to do that before. I didnt know if I looked like a hat-rack, door-man, or if she was flirting or using me. Later someone asked me if that guy was bugging me. 'What guy,' I said. Turns out the knock-out was a man who was trying to pick some guys up. She was so perfect, I couldnt honestly tell.

Answer 2

My brother's girlfriend was a stripper. ( I guess she still strips, but they no longer go out). Anyways she had tons of outfits and promotional materials ( 8x10 glossy's and all that). She was really hot chick, and super tall.

One day my brother came home to find their house had been broken into. He ventured upstairs, to check if the jewelery had been taken. In his bedroom he found he found a midget dressed in his g/f's clothes and masturbating over her photos which were spread all over the floor.

My brother beat the intruder senseless, to the point of unconsciousness, then called 911.

the police arrived, and when buddy finally came to , he tried to tell the Police that my Bro had kidnapped him, forced him to dress in the sequined outfit and tiara, then made him "entertain" himself.

Of course nobody believed the guy, and when asked why we should believe the story, he said;

"Why would I put on clothes that are too big for me?"

Answer 3

Why would you want to know in the first place?

Answer 4

Once I put on my man t shirt, does this count?

Answer 5

none that i can remember