I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.

Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I discovered that it was another old friend who had gone through a full sex change. I had no idea at all that he had done this as it had been kept private. 

She had renamed herself, Sarah. She asked me if I would still talk to her now that I knew. I said yes, of course I would and that I didn't have a problem with it. Secretly I had another motive.

I remember thinking about it incessantly over the next few days. The secret, lonely life I had was fun but was still frustrating. Here was someone who had had the same issues and desires. By far the biggest fear I had at that time was that someone might find out, disapprove and tell everyone.

I did feel shame because of the way society viewed cross-dressers and transvestites. There were also many ramifications with this being common knowledge, my business, my children, and violent bigots etcetera. If only it was possible to talk openly about such a lifestyle. I didn't want a sex change but love dressing up.

I realised that this was the first time I had actually talked with a trans person and was desperate to tell her my secret and the frustration I was experiencing. Inside I had this burning desire to tell someone about it. This seemed to be my chance knowing that she would understand. 

I nervously approached the subject and asked if she had started with cross-dressing. She had. The conversation went on for a little while and I was trying to act as if I was just curious. Sarah told me that I was very accepting and it was refreshing to find someone who didn’t judge or rebuke her for being what she wanted to be. This was the moment when I knew that I could tell her, but still, I resisted. She was obviously aware that something was a bit untoward but refrained from commenting. 

As I went on I approached the fact that it must be difficult to admit that one was a crossdresser and to tell anyone. Sarah assured me that if such a revelation was going to be admitted, it was far better to talk to someone who had gone through the same experiences. Bang! this was my chance.

For a few seconds, I stayed silent as my mind panicked. All sorts of emotions percolated every cell in my head, ‘tell her, admit it, own up, say you crossdress and have done so for years and you love it, and try not to get too emotional and cry, but do it, do it do it!’

Well, I did. 

“Sarah. I am a crossdresser. I have done it for years and no one knows. It’s been my lonely secret. Can we talk about it?”

Sarah was wonderful and very understanding. She told me that she did suspect as the conversation was very revealing. She knew how hard it was to come out and say it. 

“Be proud that not only do you dress but that you have admitted it to me,” Sarah said supportively. “It’s ok, really it is. You are not alone. There are many people who do the same.” 

She told me that I had to pick a girly name for myself as that was what ‘we’ do. I started thinking about it and then decided that I liked the name ‘Lucy Lou.’ We also talked about certain aspects of the whole cross-dressing thing. How and when I started, what I wore, and was there ever any sexual element to it. It was uplifting and I felt so relieved. We decided that we would talk in a day or so after I had got my head around the fact that I was no longer alone. 

I put the phone down and sat there dazed for about five minutes. I actually felt really turned on that my dressing had gone up a stage. I immediately went to my bedroom and opened my case with my clothes in it and started to dress. All I had at that time was a wet look basque, a pair of panties and fishnet stockings but it still felt invigorating. 

Sarah told me that there were websites for cross-dressers and trans people and I should go to one of them and create an account. The first one I went to was a site called Tvchix.com. I logged on and started the process. I didn't stay on the site for very long as it turned out to be just about sex and masturbating, which wasn’t really what I needed at that time. 

I was determined and started searching the net for something that was more serious and where I could talk about my issues. I found a site called crossdressers.com and enrolled. It was much better and was a  revelation when I realised that I was not suffering alone and that there were thousands of guys/girls just like me. It wasn’t about sex or dating but a place where there were forums where sensible, intelligent discussions took place. This was really what I so desperately desired.  

It helped a great deal because I sorted out some important points, almost immediately. The most important point was that of something called purging, i.e. throwing all my clothes out and saying to myself that I was wrong to be doing this and that I would never go back. But after a few months, I would feel the desire and need to dress again. So would start again, feeling so sad that I had lost so many lovely things. 

I found out that this was also a normal thing for crossdressers. Every time I had purged I regretted it. Some very kind and understanding girls helped me deal with it and told me that if that was my mindset that I should just put everything in a case and stick it in the loft or garage or somewhere out of site. When the desire came back I could just pick up where I left off, without having to go back out and buy a load of new stuff.

They also made me realise that this was a part of me that was never going to go away so I should just accept it, embrace it and most of all enjoy it. I did feel somewhat liberated. 

Two days later I called Sarah back and told her all about my findings. She was very encouraging and we discussed what else I needed to get. I had no picture on the site but it would be much better if I did. 

The journey began with new vigour and the desire to get myself looking feminine was paramount. I found places online where I could get some wigs and dresses. I had already found a place to buy lingerie but needed so much more if I was going to do it properly.

Shoes were a problem because I wanted stiletto heels but no shops would stock them in my size. I did find a place in Spain that had all styles of heels and women’s shoes in all sizes, even mine. Every time I ordered something I felt excited and couldn’t wait for them to arrive. It was an exciting time. I also found a place to get breast forms and decided that 38D would be right for me.

Then there was the whole issue of makeup. What would I need? Foundation, blusher, powder, eyeshadow, mascara, eye pencil, lipstick, and perfume, (which would only be for me as no picture could be smelt.) Then I had to get some jewellery. Earrings, necklaces, rings and bangles. 

As this process continued I realised that it was quite expensive making myself look like a woman. Really expensive. Hundreds and hundreds of Euros but I was committed and just made it happen. 

The other aspect was that I had to learn how to put my makeup on and the more I did it the better it got. I took pictures of myself and practised. I accepted the fact that I needed to improve but found a look that I liked and posted some pictures on my profile page, found an avatar face picture and then suddenly it dawned on me that I had done it.

There were some very lovely complimentary comments made by other dressers and this made me feel good about myself. I could be a cross-dresser and show pictures of myself, talk to likeminded girls and just embrace the whole experience. 

This whole wonderful experience also made my self-stimulation so much more for filling. Being dressed turned me on and seeing myself dressed like a woman has made it better than I could have imagined it would. 

I have had such a ball and love being Lucy Lou.