A brief history of my crossdressing years between my first sustained period of crossdressing ending in 1986 at the age of 21, through until I made myself known to the trans community in May 2009 at the age of 44.
I first began crossdressing in 1978, when I was 13. I dressed a lot at home, when my parents were out of the house. When I entered my early 20s, I dressed very infrequently and this continued for the next decade. At the age of 21 in 1986 I was really not that interested in crossdressing. There were the occasional dalliances in various girlfriends lingerie but really nothing more than that.
In early 1995, a few days before my 30th birthday, I met my future wife, and we moved into a small rented house together, later that year. Very early on in our relationship my wife told me that she had been in a couple of lesbian relationships in the past, but now preferred men (Apart from an infatuation with Marilyn Monroe, which is entirely understandable and something we have in common). It didn't phase me at all as I'm fairly laissez-faire about sexuality. I chose not to mention my past crossdressing exploits. But I thought that if things changed in the future, I would probably get a reasonably positive or sympathetic reaction if I ever did come clean about my desire to dress as a woman.
We lived in our rented accommodation for two years, until we had saved enough deposit to buy a small house in a nearby town, which we moved to in 1997. By now my fiancé had got a job working shifts that meant that a couple of nights a week, she would get home from work a couple of hours later than myself. Also she would be at work for 12 hours on some Saturday and Sundays.
Well suddenly I found myself alone in a house with a wardrobe full of my fiancé's clothes. And she had put on a little weight recently, so she was a size 18/20, which just happened to fit me perfectly. And as the song by The Smiths says, "Oh the Devil will find work for idle hands" .
I hadn’t crossedressed once during our first two years together in the rented house. But now with a wardrobe of women's clothes that fitted me, I felt the desire returning. At first I just wore my future wife's lingerie and underwear. She had some nice full bras and big knickers (panties if your not from Britain or Ireland). I've always preferred big knickers to skimpy ones, so I loved them. She also had some lovely one piece corsellettes, which are my favourite type of women's underwear. That was a link back to my early crossdressing days, because my Mum had a wonderful collection of corsellettes and girdles that I had adored wearing. So I loved to wear her corsellettes. She also had some lovely satin chemise nighties which I loved, both on her and on me. She used to wear them for me when we had sex, because she knew how much i loved seeing her in them. What she didn't know was that I loved wearing them too, and when we made love with her wearing one of them, I would be looking to wear it myself at the earliest opportunity.
Around this time, I discovered the 'World Of Transvestism' magazine and I would look at the photos of the transvestites, as we were called back then, and wish I was like them.
There was definitely a very sexual and erotic motivation to my crossdressing for three years or so after we moved into our house. That was different from when I had dressed as a teenager in my Mum's clothes, which was more about being feminine and being a woman. Perhaps this change of focus was down to me now being a fully developed male in his 30s, and also because I had lost the natural and pretty androgynous look of my teens and early 20s. So I felt very much like a man dressing in women's underwear rather than a feminine entity, as I had in my teens. It was enjoyable dressing like this on a sexual level, but my crossdressing had felt so much more satisfying before and didn't feel as good now. I even felt guilt about dressing, something I hadn't felt before.
We got married in 1999, when I was 34 years old. I remember having very conflicted feelings on our wedding day. And I'm sure it's something that many crossdressers who get married to a woman feel. Joy at getting married to the woman you love. But jealousy because you want to be the bride in the beautiful dress. Well four days after our wedding, my new Wife went to work and I dressed fully in her bridal outfit. It felt wonderful and exciting. But also very sad, because when I looked in the mirror, I saw an overweight man in his mid 30s, wearing a wedding dress and looking ridiculous. It upset me and I decided to make another concerted effort to give up crossdressing for good. I gave it a good go. I didn't crossdress again until 2001.
When I did begin to crossdress again, I made sure it was more full dressing and not just lingerie and underwear. It made me feel much happier than just being a man playing in his wife's knickers. But I still had a sense of dysphoria when I looked in the mirror and saw that man, now in his late 30s, staring back at me.
There was a problem looming with crossdressing in my Wife's clothes. Dress size. My wife was putting on weight and getting bigger. Which I didn't mind, because I find plump, curvy women very attractive. But it was a problem for me, with regards to wearing her clothes. I was now a size 20/22. My wife was a size 24 and soon grew to be a size 26/28. Which I must admit I loved. But it meant her underwear no longer fitted me. And her outerwear hung off me and didn't fit well. It did make it less fulfilling for me to wear my wife's clothes and so the crossdressing dwindled away to only being a very occasional thing by 2004.
I was deeply unhappy and unfulfilled in my life as I approached being 40 in 2005. And it was a dissatisfaction with my femme life that was behind this. A few weeks before my birthday, late in 2004, I had bought some underwear and hosiery from Mark's & Spencer's and Evans, and I bought myself a cheap wig from Ebay. It was a shoulder length brunnete bob style. It looked ok for the money. It was nowhere near as good a quality as the ones my Mum used to own, which I borrowed. My own hair was now short and rapidly greying, and no longer conducive to achieving a femme presentation. I began to dress more fully and even returned to using make up again, which I hadn't done since I was 21 years old. I looked quite pretty as a middle aged plump lady, which I didn't mind at all, because I have always found women like that very attractive.
With renewed confidence in my ability to dress and look attractively femme, I entered my 40s full of optimism. Some of the clothes in my Wife's wardrobe still fitted me, and I found myself so much happier looking in the mirror and seeing a woman looking back at me, rather than a middle aged man in women's clothes. I remember my Wife had a lovely black lace teddy top that was stretchy and looked amazing on both me and her, worn with a black bra, visible underneath. I used to wear it with a lovely red jacket and a long dark brown suede skirt and a pair of ankle boots, which were all my Wife's apart from the underwear and hosiery. I felt wonderful. I was in a very happy place in my life, and they say life begins at 40, right? Unfortunately this was before I got my first digital camera, so there were no photographs from this happy time.
With this renewed sense of optimism and enjoyment, I decided I wanted to reach out to the TG community. I now had a home computer and access to the internet and I spent time on the world wide web looking at photos of other crossdressers. I saw a letter on the problem pages in a woman's magazine about crossdressing and the reply mentioned a group who catered for crossdressers, and a phone number for their helpline. And so I had my rather unfortunate experience with the Beaumont Society, which I wrote about here. Basically the person representing the Beaumont Society called me a time waster because I got tongue tied when they asked me a question. It greatly upset me. I had recently been diagnosed with Aspergers Syndrome and so I was prone to to taking setbacks quite hard, and it really did knock me back a long way. I purged my small collection of underwear and my wig, and I once again vowed to give up crossdressing. And for two years I succeeded. But I didn't feel happy in my life. This period also coincided with my Wife getting pregnant and having a miscarriage, which was hard for us both. I didn't look after myself during this period of my life and my weight soared to nearly 20st.
The desire to dress was still in the back of my mind, but I managed to dismiss it for two years, until in 2007 I tried on my Wife's underwear again and it fitted. I was both delighted and upset. My Wife was now a size 28 and so was I. All of her clothes fitted me perfectly. I bought myself another wig. Again a brunnete bob with lighter highlights, this time a little shorter than my old discarded wig. I bought it from Doreen's Fashions, the London based store specialising in clothes and accessories for crossdressers. It was a much quality than my old wig. Anyone who met me or viewed my Flickr page between 2009 and early 2011, will have seen me wearing this wig. When I was fully dressed in my Wife's clothes, I looked like a pretty but very fat middle aged woman. I wished I was a little smaller, but still liked what I saw in the mirror. As I said previously, I do find large women attractive, so I didn't mind being one. And I looked very convincing.
Late in 2008, I became very ill with bronchitis and then pneumonia, and my GP advised that I really needed to lose weight. I did lose nearly 2st, although I was a little loathe to lose more, because I wanted to stay able to wear my Wife's clothes. But then she also decided to lose weight. So I weighed myself on New Year's Day 2009 and I weighed exactly 18st. I was a size 28. I gave myself six months to drop two dress sizes to size 24. I also promised myself that I was going to buy my own clothes from now on. I would borrow items from my Wife but only if they looked good on me. And I wouldn't wear her underwear anymore. I didn't dress until May when I weighed myself and I had lost a stone. I ordered a size 24 skirt and top from Doreen's Fashions and it fitted perfectly. I had achieved my goal a month early. I took a trip to M&S and bought myself several pieces of underwear, lingerie and hosiery. I ordered a make up kit from The Boudoir Dressing Service in London. And then I dress fully in my own clothes, wig and make up for the first time in my life. I was 44 years old.
Now I needed a name for myself. When I was a teenager I called myself Wendy, but had stopped using it, and really hadn't chosen a replacement name. From the age of 21 until I was 44, I was 'The Girl With No Name'. With my male first name being David, I settled on Davina. Or to give me my full name, Davina Anne Williams. Anne was chosen as a middle name because it fitted with Davina nicely. And Williams is the surname I was born with. My Father died when I was 6 years old and my Mum remarried a few years later and I was given my Stepfather's surname (which will remain my secret). Of course you all know me as Deeanna Williams now, and the reason for the difference in name will feature in a future episode of the epic adventures from The Other Side Of Life.
Anyway, back to this story. As I mentioned, I enjoyed looking at other crossdressers, transvestites,Tgirls, drag queens, queer folk and trans women on the internet. One crossdresser who I particularly admired, was a mature girl called Gillyanne Charlotte Blake, who had a website called Gilly's Corner Of The Web. I felt moved to writing to her, and we became good friends for a couple of years. She mentioned a very supportive and fun forum that she liked to visit. It was the UK Angels forum. This forum was run by a trans girl called Jo Angel, who also hosted Gilly's website. My timing wasn't great with contacting Gilly, as she had decided to give up crossdressing (or as she referred to it, "Hanging her tits up") and so she had sold most of her clothes and given notice to Jo, to close her website down at the end of the month. I stayed friends with Gilly's male alter ego, George for a couple of years, but eventually we drifted apart without the shared crossdressing. But I did sign up to the UK Angels forum on May 24th 2009, which is the date I consider as the starting date for my current crossdressing life as Davina and then Deeanna.
I will write more about my time on the UK Angels and other aspects of my trans journey on a future post.
So 2009, aged 44 and now engaging with the trans community for the first time, I took my first photos of myself. Not very good ones, but I used them to show myself to the TG world for the first time.
The next episode of this story will follow in a week or two, entitled 'The Girl Who Put The Lightning Back In The Bottle', so if you enjoyed this story, then look out for that.
I hope you enjoyed this story from my crossdressing past. Here are my first photos that I posted on to the UK Angels forum in 2009. Sadly the UK Angels forum closed earlier this year due to the complications caused by the Online Safety legislation and the liability surrounding it. But it will always have a special place in my heart as the first place I felt at home as a trans-femme girl.
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