First and last my name is Lisa. Not my real name, but something I go about whenever I do a little gender play. I am 48 and I like to explore my feminine side and by that also enjoy taking it to the extreme from time to time. If you were to run into me by accident you would not notice anything strange. Mid-life, an average-looking guy, and nothing else about it. I like to keep things private, but also I miss talking and sharing things like this with like-minded people. Truth be told, it is still a pretty big tabu in society, even though it should not be.
My first experience with cross-dressing was back in the mid 90`s, and it happened by faith I guess. Have no idea. A female friend has a project about transforming a man from young to old, and she asked me to model for her. Back then I was young and did not have an ounce of too much body fat so to say. This was fun enough, but a few weeks later at a party she and a friend of hers asked if I wanted to model again. They said you should go out with us. We can transform you and we can all have a girl's night out. Young and curious I said yes, sure why not? I don`t know a thing about this, but what the heck?
Not fully understanding what I signed up for I did not think much more of it until I got a call from her asking if we could do it next weekend. Don't worry about it. I got everything.
The day came and they came home to me with a few giant bags of supplies. All in, yes that had a different meaning from then on. As she studied for a make-up artist she had things I did not even know existed back then.
So I got shaved from head to toe, body shaped with actual theatrical breasts, and put on lingerie, dress, wig, makeup, and high heels. Still, remember when I looked at myself in the mirror before going out. I did not even recognize myself.
Well we went off, and I was amazed at how well I could walk in high heels. Or so I thought anyway. At the club is was a staircase going down to the basement, and not knowing any better, I started to walk down. I learned something new about gravity and high heels that day. Lucky me there was a guy in front that I grabbed onto as I fell, and he caught me and said.
Are you all right? That was an awkward situation.
Well, that was my introduction to this world. Some 30 years later I still crave the urge to gender play from time to time. And now that the kids are big and I am divorced, who knows what that might lead to?
