It Was A Dark And Stormy Night...

Actually it was a warm summer afternoon. We had just moved to a new subdivision still under construction and there weren't many kids my age to play with. I was (still am) a normal guy at 7 yrs old. I liked to do what all boys did at that age. Play cowboys and indians, kickball and trade baseball cards. Problem was, there was only one kid within walking distance to play with and he was a little different than the kids I was used to playing with... he was a 6 y/o cross dresser, if there is such a thing.

One afternoon we were in his basement when he dragged out a huge trunk and asked if I wanted to play dress up. He opened it and started pulling out dresses and hats, scarves and high heels. For some reason I didn't run screaming home!!! I remember thinking it was wrong for a boy to wear girl things, but the idea of doing something so strange appealed to me on some level. His mother soon appeared and suggested we have a "tea party" and she would make us some lunch. My heart was pounding as I pawed through the colorful dresses and handbags selecting what I was going to wear. Everything was too big for us, but I remember selecting a brown flowered dress that  just stopped short of my ankles, beige pumps a a pillbox hat that had netting over my face. I completed it with a large brown handbag and white gloves. We put on huge clipon ear rings and fake strands of pearls.

Funny I don't remember what my friend chose. but I do remember we practiced walking in the pumps like ladies, even speaking in high voices even though we probably didn't need to. His mother returned with a tray of goodies and lemonade served in tea cups. She commented on how pretty I looked and how nicely everything I chose went well together. She gave us instruction on how a proper lady sits and drinks her tea. She even decided she would call me Mary when ever I came over and played dress up with her son. Well, we spent the rest of that afternoon as any young girls would, playing with dolls and trying on different outfits.

Walking home that evening I remember a sense of dread coming over me. What if anyone found out about what I did that afternoon? What if my older brother and his friends found out? And why did I enjoy it so much? I never went back to his house to play again... in fact I made it a point to avoid him.  I thought it was best forgotten about... for a couple of years anyway.
marylee196444 marylee196444
2 Responses Jul 19, 2010

I too have dressed on and off for years, mostly off lately, but for some reason all these feelings are coming back strong now and isn't accepted by my wife. I too make myself have a big O, and then it's back to being male. Also feel kinda guilty and sad after.

Too bad you didn't pursue your crossdressing. I love to crossdress even though I am a straight male. I love the feel of womens clothes on my body and whenever I am dressed up I jack off. When I *** I eat my own load. I have been doing this since I was 9 yrs old. I only dress when I am alone but I do enjoy the pleasures of putting on women's lingerie and dresses and acting like a true woman. But once I jack off I return to my straight male role.