Cleaning up someone else’s message

What do your clothes say about you? If only you could eavesdrop on them. I just hope my underwear knows when to be discreet…

As a straight guy, there are certain things I find attractive – like short skirts, tight dresses, low-cut tops. And I want to wear clothes I find attractive, so that’s what I often go for. This doesn’t mean I think all women ‘should’ wear these in order to be attractive – that’s not what I mean at all. Nor is it about trying to look attractive to other people. It’s about wearing clothes that you think you can wear with some degree of confidence. If you think you’re wearing something attractive, it will boost your confidence. You have to be careful though – ‘attractive’ isn’t the same as ‘attention-getting’.

Like it or not, people will read messages in what you wear. Before I really got into cross-dressing I didn’t fully appreciate that because some women might dress in tight or skimpy clothing, it doesn’t mean they’re inviting sexual advances. Hell, I’m certainly not inviting anyone for anything! But it’s still a commonly-held misconception that rape victims were somehow ‘asking for it’ (this argument has even been applied to domestic violence as well).

This throws up all sorts of awkward thoughts for a cross-dresser.

Am I somehow helping to ‘objectify women’ (unintentionally) by dressing in short skirts? Am I somehow perpetuating one standard or another for how women should dress? (Some of my female friends say I’m far girlier than they are, for wearing heels or the makeup I put on.)

Reactions of passers-by vary according to what I wear, but broadly speaking men will look at my tits and my legs and then move on to the next person. Women are more likely to look at my face, and more likely to do a double-take (probably because I don’t walk in a feminine way). I sometimes wonder if guys should be made to dress in skirts and dresses for a week or so at school,  just to see what it’s like to be regarded as a woman. (I don’t for a second believe cross-dressing gives a guy any insights into what it’s like to be a woman; only how women are seen.)

From my point of view, when I cross-dress I want to disguise myself as thoroughly as possible – that’s why I choose to wear the clothes I do. So far I haven’t received any negative reactions (the worst was a couple of snickering teenage boys in tracksuits waiting at a bus-stop when I passed by), but that’s probably down to the city I live in and the friends I’ve got.

I do think that women are all too frequently seen as ‘sex objects’, and it becomes more obvious to me when I dress as one. But would I notice it quite so much if I dressed in jeans and a high-cut top? I doubt it. Do I intend to dress as a sex object? No! (But part of me can’t help but wonder if it influences some of my clothing choices.) As I said previously, looking ‘sexy’ isn’t the aim – looking passably feminine is. If someone ‘sees’ a message in my clothes (“He’s dressed as a woman! He must want to have sex with men!”), that has to be their problem, not mine. Clothes can be cut in ‘sexy’ styles or from ‘sexy’ fabrics, but how sexy it is depends on who’s wearing it, and how sexy you find them whilst they’re wearing it.

Sexy people can wear unsexy clothes – but are they still sexy? Unsexy people can wear sexy clothes – do their clothes suddenly, magically make them sexy? Either way, is it the person or their clothing that’s having that effect?


Choices, choices…

So what makes me choose the clothes I wear when I go out looking feminine?

There are certain practicalities to consider (hiding the engineering works required to fake up my cleavage, how much walking will I do, will I be likely to need to take a toilet break, that sort of thing), which rules out a lot of great-looking stuff (halternecks, strapless or backless dresses, mostly – this is really annoying).

If I want to pass as feminine (at least on first glance, and until I start speaking), then I don’t want to wear unisex stuff – I can wear jeans, trousers, ordinary shoes or trainers, shirts and what-have-you as a guy. Normally I’d never show off my legs or expose my chest, but I have no problem wearing short skirts or showing off cleavage (one of these days I’ll explain how I do it).

Part of the attraction of cross-dressing is wearing stuff I wouldn’t normally wear (it’s not a lifestyle thing for me; it’s more of an occasional social thing). Because this isn’t a lifestyle, I’m not keen on spending too much on it; I’m a charity-shop transvestite (which has the advantage that if I buy something the wrong size, at least I haven’t wasted vast sums on it).

I want to wear something that looks good, but not overly glamourous. I usually want to dress to fit in, rather than stand out too much: flared skirts or dresses, flat calf-length boots, cardigans. My legs are a battlefield, so I’ll wear tights or leggings rather than leave them bare; I found thick flesh-coloured ballet tights can cover up a multitude of sins…

Occasionally, I might want to show off. It’s a bit of a circular argument here. I’ll see a dress I think looks great, but only because it’s tight and really flatters the mannequins in the shops. So I’ll buy it and discover I’m too damn lumpy and flabby to pull it off. I then spend weeks or months losing weight and practising tucking everything away until I think I can wear it. By this point, I think I’ve earned the right to wear the damn thing, and am prepared to put up with all sorts of discomforts to wear it. (This also applies to certain fancy dress items; I think if I’ve been out and about often enough dressed in everyday female clothes, then once in a while I can try out something a little more extroverted.)

So that leaves a huge range of things to sift through, and throws up a few issues most guys might not even consider. That’s a topic for my next post, though…