My First Time I Crossed DressedThe first time I crossed dressed I was 14 and it was for a costume party at church. There were 5 of us kids and money was tight. My mom said I would be going as a girl. First she had me put on a pair of her panties then one of her bras and stuffed it with kleenexes. I remember the panties and bra felt really good on my body. Then she had me put a pair of panty hose which also felt really good. I was a bit taller than her and about the same size she had me put on one of her dresses. I liked it too. Then we proceeded to put on make up. The rouge, eye shadow, eye liner, and best of all red lipstick. She did do some plucking on my eyebrows to give them a more female look. We used a new cloth mop head for my hair and one of her hats for my head to hid the seam in the mop head. As if that wasn't enough I wore a pair of shoes with 4 inch heels. Then for the next hour and a half I was parading around the house learning to walk in heels and like a lady. I also had to sit like a lady. I also wore white gloves. I had a complete feeling of satisfaction at that time. Now I know It was a turn-on for me. I was the first of the kids to get dressed. I don't remember how they were dressed. We all got into the car and went to the party. They went in first and I would come in later. As I came in people were asking "who is that" trying to figure out who I was. As they did I walked like a female and like I had worn heels for years. I went to an empty chair slid my hand down my butt and the back of my thighs as I sat in the chair and crossed my legs lady like and gave little flip to my dress to put it on top of my legs. Boy those hose felt good as my legs were crossed. Well they were able to guess who everyone was except the young lady who arrived alone. ME. So finally they gave up. I removed the hat and the hair and put my glasses on which mom had. They could not believe it was me. Some of them said I was a pretty girl.The rest of the evening we played games all this I was still dressed as a lady. All total I was a woman for about seven hours and loved it. Over the years from time to time I put on my wife's clothes for a little while she is out and still love it. I have my own bras now since I have developed breasts. I also do theather acting and one dream is to have a part as a male dressed as a woman so I can parade around in front of hundreds of people dressed as a woman.
What do you think?
Adam59 56-60, M 11 Responses 18 Feb 12, 2012