Crossdressing Story from Start to Present Day

This is my crossdressing story from start to present day. It may be similar to yours, it may be completely different, but it’s mine and I hope that it in someway helps other people open up about things. For me it all started when I was an early teenager, I would say around 13 years old. Usually the time of self discovery for many teenage boys. You reach this age and suddenly your mind becomes open to girls around you. I was never a hit with the girls especially at school, but I had a few friends who were girls, and they found me comforting and easy to talk too. We would hang out and they would have their usual conversations about boys they liked, clothes, make up etc. And although I was very happy with my sexual orientation, I felt like I was more in tune with my female friends than my male friends. I seemed to understand them better, be responsive when one of them was having a bad day or dealing with a problem they needed to talk about.

"I cannot describe the feeling I had when I first put on those pair of tights, how they held my body, the smooth material on my skin and they felt so good."

Like I said I knew I fancied girls, still do, but I wanted to have a deeper connection. For me to better understand women I needed to be more feminine. In order to do this I sneaked some clothes from my sisters' wardrobe on a day that I knew the rest of my family were going out. Just a pair of tights and a skirt to begin with. I cannot describe the feeling I had when I first put on those pair of tights, how they held my body, the smooth material on my skin and they felt so good. The material, the texture, from that moment I knew I was in love. The skirt was perfect too, I looked at myself in the bathroom mirror and had my first feeling of what it was like to wear girls clothes and it felt really good. I continued in any free time I got to try on clothes were I could.

I tried to also have a chat with a friend about it when I was about 15-16, his opinion on the whole thing was made very clear to me, so I made a joke of it and said no more. I now believed that it was something weird and that I should be ashamed off it. So I purged myself of the small collection of clothes I had and attempted to move on with my normal boy life. For 4 years I told myself that it was weird and not normal and that I shouldn’t be doing it. By now I was 20, I got a job, had a couple of girlfriends, but had never gone back to thinking about let alone wearing feminine clothes. But I knew the feelings were still there. When I had intimate times with a girlfriend I would always enjoy it when she would keep her lingerie and/or stockings on as I loved the feel of them against me. It was the closest I could get to enjoy that sensation again but not being viewed as a weirdo.

 "It was the choice of how I could express myself through clothing and mix and match between pairing male and female clothes together."

By my mid twenties I had a few years of being single and not dating a lot of girls so my need to feel that feminine side arose in me again much stronger as I had spent so long burying it, and thus I went out to buy some new feminine clothes for myself. I had more money and my own place, so I was able to live in this little, comfortable world of my own making where I could enjoy getting dressed up. It was around this time that it also discovered that it wasn’t necessarily about the thrill or sexual excitement of getting dressed that was giving me the true pleasure. It was the choice of how I could express myself through clothing and mix and match between pairing male and female clothes together. I could wear a nice skirt with a cool t-shirt I had and I loved the freedom it brought me. But again it was still in my little world and at the time there was no way I way I was going to share this side of me. Partly because at the time, this was for me only but also because I had the fear of it being rejected by my friends and me having to lose it again.

"She does understand that at the end of the day it is just clothing and it is a way of me expressing my true self and being happy in myself."

Now let me bring you right up to date. I’m now married, my wife does know about my crossdressing. She understands my want and need to do it as we have discussed it at length, but for her it is a side she cannot make herself a part of and I totally understand her and respect how she feels. I know it doesn’t change the fact that she loves me for who I am. She does understand that at the end of the day it is just clothing and it is a way of me expressing my true self and being happy in myself. I do however continue to keep it mostly to myself, but I do have the occasional day trip out or weekend away with some girl mates that allow me to fully get dolled up, dressed up and let my hair down in whatever I fancy wearing. I have 2 guy friends who know about my feminine side and they have been great supporters since being open with them. My wardrobe has grown drastically, lots of gorgeous dresses, skirts, tops and I now have more pairs of heels than my wife. Unfortunately for her my feet are way to big for us to share. I still love to mix it up, I still have my guy days and I love my days with my ladies.

"...you shouldn’t never be ashamed of who you are and you shouldn’t let other people dictate how you love yourself and express yourself."

I know that I still have a way to go with my journey, but I am in a much happier, healthier place than where I was even 5 years ago. The world that we live in is still a very sheltered place, people are still very unaccepting of things that they don’t know about or don’t understand. But I know things will improve and that we will become a more inclusive society one day. Where individuals can wear what they want, say what they want and love who they want with out being judged or vilified. My journey is still continuing and I hope that some of what I have written about may resonate with others. What I have discovered about myself through writing this is that, you shouldn’t never be ashamed of who you are and you shouldn’t let other people dictate how you love yourself and express yourself. Thanks to Sandra for giving me this opportunity to put into words my little story and I hope that we can start to see more change and more acceptance in the near future. Xx

- Joseph Cleeves