A Crossdresser Story

So for the first time the world would met Sindy.

I felt I knew Sindy well but no had ever really known so every experience felt like I was doing it for the first time. All my senses were tingling and I didn’t know what to expect in terms of reactions, not only from my work group but from others at this event.

We had been dropped a short distance from the entrance but as this was my first time in heels I found it hard to keep up with the others. Something I have learned since then is that if you are tall a good think block heel is preferable to stiletto.

Once inside we joined our table and as when news of Sindy had come out I had no need to worry about those in group who treated me as Sindy. As this point I was just looking forward to enjoying the night and was no longer concerned about and reactions from others.

We sat at our table and just this small thing was so different. I noticed as I sat I was conscious about ensuring that my dress didn’t rise over my bottom. Sitting with my legs together and feeling a slight relieve in my legs from not standing and walking in heels.

After a few drinks the inevitable need to use the toilet came and I hadn’t really given this much thought. So I stood up chin up and tried to walk as confidently as I could muster in my heels. I used the men’s toilets and when I entered it was empty. After using the cubicle the bathroom remined empty so I washed my hands and went back. On the next visit when I went in again it was empty but as was in the cubicle some other people came in. This time though people did come in. From inside the cubical I could here the laddish banter that is normal. I made the choice to embrace myself and my outfit…..

With my heart racing and no idea what to expect on the other side of the door I went for it. Trying to find all of the confidence I could I decided to turn into the skid. “Hello Boys” I declared as I exit the cubical. I could see the initial shock of the gentleman in their faces but soon it was all fun and jokes. “I think your in the wrong place love” being the first replay. Then everything was as normal as anytime. I quick discussion on how the night was going and off we went. The night went on like any other with drinks and dancing.

Sindy’s confidence soon grew and she was out regularly each time gaining more confidence and making friends with strangers everywhere she went.

One of the first places I went as Sindy regular was Metro’s in Cardiff. Wednesday nights “Cheapskates” being a almost weekly thing. Our group who all worked at McDonalds at the time found Wednesday a great time for us all to get time off.

Metros was always one of the best places to go out as Sindy as there weren’t the judging looks that you would get at other places. We had a period of always going out in fancy dress, no reason we just did. So each week we would take turns and on my first it was Disney Princess’. The main reason being it was the first time in my life I could dress up as Cinderella without judgement.

Our Metro’s nights would often start with a pre-drink in Weatherspoon’s where given a lot of time we had all dressed up we would all be subject to strange looks.

As time went on it became normal to be Sindy on a night out. On occasions when I did not I was asked why and people looked forward to me being Sindy.

In some ways it became a pressure at times when it was meant to be a pleasure.