Crossdressing Freedom

I hope this story is enjoyed by everyone who has the desire to wear clothes of the opposite sex and feel good about it. Wouldn't it be great to overcome your fears involved in being a cross dresser and have the freedom to walk down the street with your high heels on feeling good about yourself without a care in the world?

It isn't fair, women can wear men's clothes and get away with it! What happened to equal rights?  Sorry I am not here to change the world as we know it but that's how I used to feel. Luckily I found an answer which meant I could wear what I wanted, when I wanted, where I wanted without the usual fear of being an outcast of society.

My name is Zoe and although I am a man, I just love wearing women's clothing whenever I get the desire to. I would like to tell you my story purely because it might help you and others like you to pluck up the courage and do something about the feelings you have about cross-dressing. You may have your own reasons to crossdress, some men do it for sexual gratification or have a crossdressing fantasy, others because they enjoy the experience of feeling like a woman. Some crossdressers are professionals such as drag queens or escorts and others just like to wear silk knickers and stockings under their boring man clothes whilst they are at work. There are lots of different reasons and feelings as to why we would want to dress up in women's clothes.

No matter what your reasons are I don't want to bring up a debate if it is right or wrong, different or indifferent. I would however like to tell you about the one single thing that helped me break through finding out who I really wanted to be and how my life as a transvestite seemed to become complete. It took me a long time to come out of the closet and have the freedom to be myself whatever mood I was in. In fact it has taken me a long time to build up the confidence to share my crossdressing stories and photos here. I have one person to thank who really helped me overcome my deepest fears and would like to share with you what this person taught me.

Before I share my story with you I just want you to know that I understand that everybody's circumstances will be different than mine. You may be married with children living a happy content lifestyle or live either on your own or with a partner also enjoying life to the full. I cannot relate to everyone's individual circumstance but I do know that if you have read this far you either want to be a cross-dresser or you are already enjoying crossdressing as part of your life.

Perhaps you want to hold your head up high and feel good about yourself without feeling as though you are doing wrong or feel as though you are being frowned upon by other people with biased views who are living in this so called normal world. I spent many years trying to go about my normal everyday life without feeling bad about the fact that I was a secret crossdresser. Click to read chapter 2

I hope that all crossdressers understand me when I say that although I felt good whilst I was in ladies clothing I couldn't help feeling guilty because I knew that it wasn't socially accepted. I used to draw the curtains so that my neighbors wouldn't see me before I was relaxed enough to take off my boring man clothes and put on my new knee high leather boots and a figure hugging tight fit pencil skirt in the privacy of my home. I couldn't speak to anybody that I knew about how normal and relaxed I felt about wearing women's clothes as I was very afraid of what they would say and do, especially my family.

I was sitting at my computer one day wearing a silk cream blouse, my favorite black pencil skirt and a pair of shiny black patent shoes with a little buckle strap. I was feeling confident and safe in the confines of my home when all of a sudden the door bell rang. I remember having a full panic attack and started to strip off,hide the evidence and quickly got changed into mans clothes. By the time I got to the door whoever it was had gone. At that moment in time every piece of women's clothing I owned was thrown away. I would have been mortified if I had been caught. When I wear women's clothing I feel invigorated, at peace with myself and relaxed but the second there was a threat at being found out what I was wearing, my emotions would stir up and the peace would be replaced by fear and apprehension. I clearly had to find a way to stop having these mixed emotions.

It took me a long time to pluck up the courage and speak to other cross dressers over the internet and I am thankful that I did because that's where I met Jane.

- Zoe

I watched a news program about a man who felt that he was a women trapped in a mans body and wanted to have transgender surgery to turn him into a woman. The man was talking to a specialist gender therapists explaining why he felt that he really needed to be transformed into a woman permanently. This made me realize that I had never once thought about actually becoming a woman, in fact It made me realize that I also enjoyed being a man very much even though I equally enjoyed being a cross-dresser. This is something I cannot explain and never have since the first time those stockings were pulled up and the sense of being a few inches taller wearing my heels. I also knew that I was not a gay crossdresser as I fancied women a great deal and enjoyed clubbing at weekends and coming out with a hot chic on my arm at the end of the night.

As the internet grew, more information was becoming available for crossdressers, transvestites and the transgendered community for which I was really happy and relieved about as I knew then that I was not alone. Before the age of the internet I did not know how many other men like me wore dresses and spent their time looking through women's magazines so they could get ideas on what to dress up in. It took me a long time to pluck up the courage and speak to other cross dressers over the internet and I am thankful that I did because that's where I met Jane. Click to read chapter 4

I would crossdress into my white silk camisole at night and then settle down at the computer where Jane and I would chat online and exchange a few emails. After a few weeks we arranged to meet one another for a coffee. Seeing as the coffee shop was not inside my home I put my man clothes on and headed off there 15 mins early. As soon as I arrived at the coffee shop my phone rang, it was Jane. It was strange because I could hear Janes voice in my phone and behind me at the same time. I turned around and saw a very attractive lady looking at me with a beautiful smile on her face, she was wearing a cream two piece suit with matching high heels. I took a step back and looked again before I managed to say 'hello you must be Jane'. Jane said hi back and started laughing

The coffee shop wasn't very busy so we got a table by the window and ordered two coffees. We exchanged pleasantries for a while and the Jane broke the ice by asking me if that I had crossdressed in public before. I told Jane that I hadn't and only crossdressed at home where it was safe to do so. I also mentioned that I had experimented with cosmetics and a couple of wigs but I just looked ridiculous. As we continued our conversation I realized that Jane was very calm and comfortable being a lady. Her confidence flowed as she spoke to me in a sweet voice and her body language was relaxing and elegant.

As I got to know more about Jane I found out that she too used to just crossdress at home but she said that after a while she wanted to know what it felt like wearing women's clothing outside so that she could feel the restrictions the clothes had on her body as she walked down the street. The only way she could confidently do this was to look like a lady. As Jane was speaking to me I started to feel a bit jealous about her because she looked great and had the confidence to pull off being a woman. This meant that she could crossdress without the fear of anyone noticing that she was really a man.

I wanted to know how Jane managed to pull this off as I now started to think about if it was possible for myself to pass as a woman. I couldn't help thinking though that my shape and size was completely different than Jane's. She was petite built which meant that her small frame lent far more kindly towards a females body than mine. I was tall, thick boned, dark skinned, hairy and let's say a visit to the gym wouldn't have gone a miss.

When I mentioned this to Jane she said that my mental attitude towards my body was getting in the way and that she has a circle of friends that are all shapes and sizes, one of her friends was much bigger than me. I asked Jane how she knew how to look so great when other men just cannot pull it off. Jane then wrote down for me some things to find out about and try. As she handed me the note she also stated that crossdressing was just like everything else in life, if you put your mind to it then you can achieve anything. I thanked her for seeing me and we agreed to meet back at the coffee shop in a couple of weeks time. I then left clutching the list that Jane wrote for me. Click to read chapter 5