Early Experiences In Wearing Pretty Things

I’ve worn my Mommie’s clothes since I was a little boy. I remember once when I was 5 walking hand in hand with Mommie to the grocery store when we ran into one of her dear friends. She was a lovely woman and she leaned down close to me at one point and “He’s so pretty. He could be a little girl!” I felt embarrassed and turned bright red—but she spoke what was on my mind. I often wished I could be a pretty girl and one day be beautiful like my Mommie.

I would often sneak into her closet and slip into her high heels, my little feet swimming in them and then attempt to take a few steps. I liked the way Mommie walked in her heels and the way she looked in her skirts. Even as a small boy I knew Mommie was beautiful and attracted the gaze of men. I wanted that for me, too.

One day when I was in seventh grade I stayed home sick from school. Mommie had long ago left for work. I went into the bathroom and found one of her slips hanging on the back of the door. I ran my hands over it and felt attracted by its silky texture. Soon I was naked and slipping it on. I loved the way the little straps caressed my shoulders and how it hung on me hinting at a feminine shape. I wished I had breasts to fill in the top and a lovely rump to pull it tight over my bottom. I could barely contain my excitement and quickly began to stroke myself until I had an explosive organism. I was hooked. Dressing in Mommie’s undies and clothes became my greatest secret joy.

I continued on this lonely path for several years, unable to share my secret with anyone. And then several years later, I did share it with my dear friend Davey. We had cut school together and while hiding in the basement of my house, he sat on my lap. My **** grew hard from the contact and we both laughed about it. A few days later, we talked about the incident and he shared with me that he loved dressing in his sister’s undies and being femme. I told him that I loved wearing my Mommie’s panties and bras. Every few weeks we would sneak moments dressed en femme and climaxing together. Then we would sheepishly clean ourselves up, put on our boy clothes and quietly separate. But then the need to share our feminine nature would grow strong and once again we would arrange a rendezvous after school or on a weekend.
Candiegurl Candiegurl
2 Responses Aug 8, 2010

did you ever trade ********?

What a wonderful short story this is! So many closeted cross dressers and transvestites right now would love to have someone trustworthy to share their secret with and, would delight in finding that the someone would have the same secret to share as well. This is such a marvelous memory for you to have shared with us who read it. I must say that the story did leave me wondering what ever became of the two friends? Did they continue to meet together as time passed? Did either one of the friends, especially the writer ever go on to become the girl or woman that he wished he could be when he was young? The story left my mind to wander into different scenarios. Excellent.