A Crossdresser Story

"Its a phase" or so I always thought. It wasn't a phase, it wouldn't go away, that what I had to accept. In keeping it hidden I was only lying to myself and the relief when it was no longer a secret. Like the world was lifted from my shoulders. Becoming Sindy was the best thing I did in my life.

I now describe myself as a cross-dresser, a man who likes to dress up like a woman. I always knew that I liked to wear clothes that were meant for the opposite sex. I don’t remember how early but feel like it’s always been there.

Like most other crossdressers the first experience of wearing female clothing was secretly trying on dresses/skirts of female family members. Once old enough to have my own place I would still dress but in private and not telling anyone about it.

Like many stories on crossdresser forums, I would feel ashamed for some reason. Occasionally, I’d “quit” throw away any clothes and say it wouldn’t happen again. But that never works and soon your out buying new clothes and the whole cycle starts again.

It took till the age of 29 for me to accept who I was and look more into things. I looked at transitioning and with some research knew that it wouldn’t be for me. I struggle to classify myself as I feel like having the best from both worlds.

I dropped hints about it though the music I was making at the time. Using my words to open up but neither confirming what was true and what was made up. I created a Facebook profile in the name of Sindy and began adding other crossdressers.

This is how I came out. Friends from work were given Sindy as a friend suggestion and from pictures of my leg tattoos realised that it was me.

I wasn’t 100% ready for this but the reaction I got couldn’t have been better. There wasn’t really a reaction. People weren’t shocked or horrified. In fact, I believe this has made me closer to my female friends.

I was no longer hiding Sindy it time for her to be seen. Now I had dressed in front of some close friends but only ever in my house, but to go out in public. A works night out to a 1920’s era themed was the first time stepping out in public.

I bought a dress, a mid-length black flapper dress, some heels (not an easy task when you have size 12 feet) and even got my first make up.

Prior to the night out I had to learn how to walk and stand in heels and suffered some sore calves and ankles. I did not want to go out and just be a man in a dress, I wanted people to see me as a woman. I'd started to grow my hair out any way so didn’t bother with a wig. I shaved my whole body and started using female shower gels and body sprays. This soon became my norm as I just find them better smelling.

On the night I was invited to get ready with the girls, who had offered to help with make up etc. I had only ever had that male experience of going out and always wondered why it took girls so long to get ready. I now know and it’s because the getting ready together is as much fun as the night out itself.

I was excited and nervous as we got ready but felt better after a couple of glasses of wine. My friend did an amazing job sorting out make up and since has helped me to learn to do my own.

Despite some nerves I was excited to introduce the world to Sindy.

Part Two: Stepping Out Coming Soon