Crossdressers-Haven.com

I was 5 or 6 years old the first time I dressed, it was Halloween, The night before my dad had gone to a costume party in drag wearing some of my mom's old cloths and a wig that was borrowed from my moms hairdresser. So my mom decided to dress me up in one of her mini skirts, blouse, padded bra, nylons, high heels, and the same wig that my dad wore. I loved the feel of it all adn the look also. After that when I would get home from school and no one was home I would go into the ceder closet and play dressup with my mom's old cloths. I did this for years.

At the age of 17 my mom caught me sleeping in her nightgown. All that was said is " those are mine" nothing else needed to be said. I stoped dressing for years not because I didnt want to but the oppertunity was not there to.

I did not start dressing again untill I had started dating my now "wife" Amy it started with painting finger and toe nails and dressing up for Halloween. Now Amy lets me dress when ever I want/need to, as long as it stays within the home, and that is fine with me.

there will be more Halloween stories to follow but for now thats how I started dressing

Huggs
Nancy T

Interesting, my mom called it play dress up. She even gave me my own cloths so I wouldn't wear hers. Oh but of course it was a secret that had to stay in the house.

My mom also dressed me as a girl for Halloween, at my request. She was very natural about it. I did not dress in front of her again, but often when shopping for clothes she or I would pick out something and say it was especially pretty (even if it was a boy's), and I would wear them when I felt most girlish. She would always notice and make a nice comment. I'm grateful to her for accepting and acknowledging my feminine side without making a big deal out of it.

xoxo chrissie

Hi Chrissie,
It took me about a month before I would openly dress in front of my mother and she never fussed at me just help me along. I"ll never forget one weekend when she ask me if I would like to wear makeup and she done my face up. You know back in the mid 50's she and I would have been tared and feather if people knew.

Carol Ann wrote:Interesting, my mom called it play dress up. She even gave me my own cloths so I wouldn't wear hers. Oh but of course it was a secret that had to stay in the house.

A few times after that Halloween, I wanted to dress at home after school, and my mom helped me and did my makeup. I did go over to my friend Bobby's house like that once, but I don't remember that I got quite the reception that I wanted.