For many more years, than I care to remember, I believed that I was simply a once-in-a-while Crossdresser. I recall having a fascination with ladies’ clothing from a very young age, probably six years old onwards, but I can’t remember trying anything on until around twelve when I found myself at home alone in the evenings.
I was pretty well hooked from then on, but with puberty happening it all felt very naughty. During the 70s, the media in the UK, and likely elsewhere, portrayed men who wore women’s clothes as either gay or perverted. I knew I wasn’t gay even then, so I assumed that I must be a pervert. This caused me a lot of guilt and shame attached to my desire to dress. It was something that took many, many years to shake off.
Although very sporty, I was never one of the lads at school, or since really. I carried on dressing throughout my teens, initially wearing my Mum’s, and then my sister’s, clothes whenever I was alone. At the age of 17, I had one, rather bloody attempt at shaving my legs. I adored the feeling of tights on my bare legs. But unfortunately, I never did it again.
It did prompt me to go out for a walk one night while wearing my sister’s skirt, which I couldn’t fully zip up, and a pair of sandals that were so small my toes hung well over the front. It was probably as well that I didn’t bump into anyone.
As girlfriends came on the scene, dressing took a back seat, although it seemed to come back to the forefront when I was single. Eventually, marriage and children came along, and dressing was forgotten, or maybe not quite. There were a few stolen moments when I found myself home alone, I would try on a new skirt or dress that my now ex-wife had bought, but those moments were very few and far between.
When I met my current wife, I hadn’t dressed in years, and I don’t think I would have even thought of considering myself as a crossdresser, although I clearly was, there weren’t any thoughts of telling her, as I thought there was nothing to tell.
My wife soon noticed that I wasn’t much like her previous boyfriends. When she shopped for clothes, I would be there with her, unlike a lot of men dragged into that environment who didn’t go to another shop or look at the TV displays while she tried on new outfits. I was always waiting outside the fitting room, insisting that she show me, and giving her my opinion on what I felt she looked good or didn’t in.
That, and other things, prompted her to say many times over the years, “You’re such a girl,” and she means it in a nice way. She knows nothing of Lucy, but I don’t think she’d be that surprised to find out.
We’d been married about 10 years, and I’d given her no signs of dressing from me when she’d put out some underwear for throwing out. Something prompted me to divert the items away from the bin, and they were stored in a bag in the loft for later use.
Over the next five years, the items would come out if my wife went away for the weekend, and I would borrow one of her dresses to make up an outfit. Sometimes this was sexual, and sometimes I would just sit and watch TV. Almost always after dressing though, the old feelings of guilt and shame would re-appear. And then along came Covid-19. I now work from home, but my wife’s job doesn’t really allow for that.
In 2021 in the run-up to my wife’s annual trip to collect the Mother-In-Law for Christmas, I decided to buy myself some shoes from Amazon to go with the outfit that I would wear while she was away. They were very high heels of course, and I couldn’t even walk 10 feet in them, but they became a catalyst for what followed.
During the Christmas holidays, it occurred to me that I had ample opportunity to dress while working at home. I did question myself as to why I would want to. After all, for many years I’d only dressed a couple of times a year for an hour here and there and usually felt so ashamed afterward that I couldn’t put things away quickly enough.
And there it was, the lightbulb moment. I had the opportunity, something I’d never really had before! Within a couple of weeks, thanks to Amazon, I had a couple of outfits, and even some shoes that (just about) fit and were wearable.
So, there I was a “real” crossdresser after all. And then the crossdresser wanted a name! So, in 2022, Lucy was born. Lucy started to develop her own personality. She wanted to go out into the world, and she managed it for the first time in December 2022, but more of that another time.
The changes that happened with Lucy’s development felt a little overwhelming at first, but as I embraced them more this year, I realised that she’s always been there. I just didn’t get the opportunity to let her out. For the first time in my life, I referred to myself as Transgender. Some may disagree, but it’s how I see myself. Life seems to make so much more sense nowadays.
Where things will develop from here, I don’t know. As I said earlier, my lovely wife still knows nothing of Lucy, at least I don’t think she does. If she did find out, knowing her as I do, I’m fairly sure she wouldn’t throw me out, but I have no urge to tell her at present.
So Hi, I’m Lucy. I’m a work in progress…
Thank you, my friend, for sharing your story of how “Lucy” evolved over the years. You have been cross-dressing for many years, even before my time. According to your article, crossdressers were terribly misunderstood in the past, and sadly, we are also misunderstood in the present. It doesn’t make it easy for us, but thanks to the internet and CDH, we can communicate and have support from our sisters as well. Amazon has been a blessing for many CDs to shop and have our feminine clothing delivered discreetly. If in time your wife somehow finds out about Lucy, that would… Read more »