I have 5 sisters and have always wanted to dress like them. One of them had a western woman’s costume and as a young boy I dressed in that dress one Halloween
As I became a teenager, my bedroom moved to the third floor of our house where my mother stored all her clothes from the 1940’s and 1950’s. I started wearing my mother’s clothes that were in storage as a young teen.
At night, after everyone was asleep, I would take them out and dress in them. There were old fashioned girdles with garter straps and long line bras along with numerous dresses. Wearing them made me feel very feminine.
In college I did not have the opportunity to dress as a woman.
When I got married, I would dress in my wife’s clothes in the locked bathroom, using water balloons in the bra. These sessions were very short, as I could only do it while she was asleep.
After my first wife passed away I was able to get my own apartment. During that time I explored my feminine side, buying a few outfits that I would wear in the apartment after I came home from work. This lasted for a year. I never had the courage to venture out, so all the activity was just lounging around the house.
Later, I met a wonderful woman and we fell in love. We bought a house together and settled into married life.
After awhile, I revealed to her my desire to cross dress. She was very supportive and helped dress as Stephanie. We had many photo sessions around the house. We even ventured out to a concert one time.
We are looking forward to continuing my dressing as Stephanie and will certainly venture out again.
Submitted by Stephanie Krossdreski
You look fantastic Stephanie and so lucky yo have a supportive wife