Crossdressing Freedom

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