First steps in dressing up 2


Through the Internet, I did not only find a lot of documentation and information on cross-dressing, but I also met a community of supportive people who explained those things to me. At the beginning, I was as yet reluctant to talk to them. Most people I found online were almost all of the sexual fetishist type — associated to bisexuality or BSDM groups. They cross-dress as part of their sexual fetishists. My own “group”, if I can call it that way, does not. And we seem to be a tiny minority among the vaster group that does cross-dress mostly — or almost exclusively — for fetishitic purposes.

Next came the shops 🙂

Well, if you’re 1.78 m tall (5’10) in a country where the average woman is perhaps 1.65m tall, you have a problem — finding clothes, not to mention shoes (around here, women’s shoes go up to 41 on shops… and I wear a 43 1/2!) Bra sizes or panties do come in larger sizes… but they are designed for women of over 50 year, and weighing 100 kg of more. So don’t expect any fashion statements there 🙂

I looked for some online shops for countries where women are much taller — like in the Netherlands,
Germany, or the Skandinavian countries. It was rather a surprise to find not only how big the offerings were — lots of choices, even in 1995! — but that there were all sorts of shops attending exactly the needs of cross-dressers. This naturally amazed me quite a bit, since the first dress I bought, at a popular market on the street, definitely did not fit well.

So, hmm, clothes designed specifically for crossdressers. I had to try those out.

Living still at my parent’s home, my first clothes were simply stashed in a bag in my car. I always wonder why nobody ever suspected what those bags actually contained. There are always times when I could be alone on my own, and after blushing violently to pick up the parcels at a P.O. box near my workplace, I finally managed to try my first things out.

Many others have described the feelings when they first tried out their female clothes. For most cross-dressers, this happens usually very early in their lives — between 9-11 years, most often, then perhaps during their teens. In my case, I was almost 26, so I missed the whole “childhood experience”. It was, so to speak, a very first time. And I couldn’t believe how good it felt! It was clear, by then, that I had no other choice to accept that I liked it — nay, I was absolutely swept away by the feeling of all those lacy clothes, their textures, their smell. And at that time I just got rather simple things, a pair of panties, a very simple skirt, one or two plain panties, a bra or two. Nothing earth-shattering.

All cross-dressers know how addictive cross-dressing can become — once you feel the freedom and pleasure of wearing female clothes, it’s hard to stop. I hardly paused for breath before logging in to one popular cross-dresser shop once again, and starting to do some serious shopping. This time, a wig, and some latex breasts — wrapped-up socks simply didn’t feel “good enough” — and some sexy stockings. Also, some makeup, and a handbook to get some tips, to complement the ones I already got through the Web.

I remember at that time that I couldn’t even wait to try them on — so, after most people at the office left (I used to work late hours — a bad habit I still have!), I tried them on on the bathroom just after getting them from the post office. Well, it was pure heaven — even in such a cramped space as a public toilet!

As time passed, it seems that my addictiveness grew, and I wanted what for some cross-dressers is the ultimate goal: being able “to pass”. This follows an old rule: “You can fool some people all the time, and you can even fool all the people some time, but you can never fool all the people all the time” which is one of the cross-dresser’s mantra.”Fooling all the people for some time” means that the goal is to be able to pass as a female in a public space without people looking at you twice. It’s not easy to achieve, specially if you haven’t had the training as an actor and have to rely upon observation.

The other issue, of course, is that male and female bodies are usually easy to distinguish. Tricking the eye with an optical illusion — making others think that they’re seeing a female — is not easy, specially if you aim to have a “casual” look, while still presenting to oneself an exciting image. If you overdo it, you’ll be tagged as a drag queen — something that is hard not to notice.

At that point, I understood that getting a cheap wig, a few non-descript tops and skirts, and latex breasts were not enough. It was time to consider some more shopping!

  • From what little I have to go by, it would appear that you are well on your way to “passing”. As a heterosexual male, I could never explain it, but, there is so much more femininity displayed by crossdressers than their genetic sisters.

  • Thank you very much for your comment! No, actually, I don’t think I am; far from that. Remember, my genetic sisters have a life-long experience, I don’t 🙂

    It’s very hard to define “display of femininity”. In most of the world, it’s usually agreed that “gender” is a “role” we “play” (as opposed to genetic sexual characteristics), which, like most things, is always a mix of nature and nurture. I might write another blog entry on the concept, but, basically, I would say that most of the “display of femininity” exhibited by genetic females are mostly education, personal choice, and (of course), some hormonal-driven behaviour. In a sense, boys are taught to behave like boys, girls are taught to behave like girls…