This is another of my continuing series of posts revolving around chances I took cross dressing my way into becoming a transgender woman and living fulltime in a feminine world.
In the restaurant/bar I used to manage, two cis women who I presumed were in their fifties, came in several days a week to enjoy a cocktail or two. During the warmer months they used to stop by after their tennis matches in their tennis outfits. Of course I was jealous of the fact I didn’t have an outfit to match theirs.
Around the point in time I am writing about, the stores I loved to shop in started to carry short thin ribbed flared dresses in larger sizes. Perfect to put together a tennis outfit. All I needed to do was find a white one. As luck would have it, I found one in my size. I then set out to complete my “outfit”. The problem I had was finding items and then hiding them from my wife. As luck would have it, we had a rarely visited other closet where I could hide an item. Often in plain sight.
Now, back to the outfit. Finding a pair of white tennis shoes in my size actually proved to be fairly easy too. Now I had to figure out what to do about my legs. Even though I was able to shave my legs back then I added a pair of Leggs pantyhose and even added a pair of white thigh highs which didn’t exactly fit the idea of what a cis woman would wear with a tennis outfit but still added some pizzaz to the whole image. After all, I was reliving my non existent teen girl years I missed.
I finished off the whole tennis image with my long straight blonde wig.
Let me add in here, I had rarely even touched a tennis racket in my life so I would be without one when I went out. Once I was secure (the best I could) in my tennis woman outfit, I headed out to one of my favorite up scale malls. My wife was working that day so I had free time on my hands. Once I arrived at the mall, I was able to semi relax and feel the air on my legs and I found also I attracted quite a bit of attention from the older men who seemingly were there to supposedly walk but probably to look at women too.
The whole situation was I equated being stared at as validation as a woman. I was to learn later in life it was so wrong. There is a thin line between being classy and trashy when you are first cross dressing in public. I’m afraid I crossed the line into trashy in my early days of journeying into a feminine world. If my tennis outfit crossed into trashy I can’t tell you. It was so long ago.
My story is I was doing nothing different than other cis women I had mentioned above. It was only another attempt to be just like them.
Tennis was just an excuse.