How Short is Too Short?

Now, this is a question that has troubled womankind for thousands of years. Well, at least since the 1960s, any way. Just how short does a dress or skirt have to be before it is too short? And, I would like to ask, is the answer any different for us cross-dressers?

This question arose for me a few weeks ago when I was getting ready to go out for afternoon tea. I had ordered a lovely 1920s dress online, especially for the occasion, but it hadn’t yet arrived. My backup dress was a silver little number I had found in a local charity shop. It was covered all over in tassely fringes and was absolutely gorgeous. I arranged to show my friend Ginny and, when she did the magic knock on my office door and I unlocked it and let her in, she stood there watching me for a minute as I walked up and down. She agreed that it was lovely, and then it came… “Do you think it’s a bit short?” she asked.

Well, I admit it was short but wasn’t that a good thing? And, anyway, weren’t flapper dresses terribly short in the 1920s? “Well, it’s up to you,” said Ginny. “But it’s not something I would ever wear.” Now that, of course was a death sentence for that poor old dress. Back it went into the drawer and, a week or two later, when I had a clear out, off it went to the charity clothes skip.

This question is a very interesting one, if I might philosophise for a moment, because, after initial consideration, I believe there are multiple answers to this, multiple truths. Let’s consider some examples. Take a young woman, or a young crossdressing man for that matter, and put him/her in a knee-length dress. Make the subject take a walk along any British high street and no one who saw them pass by would have anything to say on the subject of hem length. Okay, so now let’s shorten that dress a little to, say, about six inches above the knee. Make the subject walk back down that high street and what would be the reaction now? Well most people, I would suggest, would not bat an eyelid and those that did notice anything would simply think ‘Oh, look! There goes a fashionable young woman’ – that is assuming, of course, that the crossdressing subject would pass in other regards.

But now it gets interesting. Shorten that dress just a little more to around 10 inches above the knee and I think we would start to see a difference. Our subject would now start to turn heads. Passers-by would start to think ‘gosh!’ and ‘goodness me!’ But the verdict would still be positive, from most people I think. “I wish I had legs like that” would be a common response to seeing a young lady walking down the street like that.

But if it was a transvestite? Yes, heads would turn. People would take a second look. They would see the skirt and then they would notice the narrow hips and the broad shoulders. They would notice that the coiffured hair was almost too good to be true, to be real, and that jawline…! “Isn’t that…?” they would whisper to each other. Everyone would turn to stare and, for our cross-dressing subject, that lovely experience of being out and about dressed as a woman would change into one of cringing embarrassment.

So here we have reached an important point: a hemline can be too short if it attracts unwanted attention. And this is what I think Ginny meant with her critique of my tassely flapper dress. The balance is a fine one. Yes, we transvestites like to feel ultra-feminine – I think that’s only natural when you spend most of your time lumbering around as a man – but we also like to fit in and feel comfortable. Good call, Ginny!

Now let us continue with our thought experiment, because this next bit gets very interesting. Let us shorten the dress on our subject again, now to about 12 inches above the knee. Now some kind of line has been crossed and the reaction from passers-by would be quite different. Whether our subject was a gorgeous young woman with fantastic legs or pretty obviously a man in a dress, the hemline would be considered definitely too short. But why? This I would be interested to know. I would like to take a microphone and go and interview some of those passers-by.
“Why do you think the dress is too short?” I would ask some nice lady who I might find standing outside the local Tesco.
“I don’t know, but it is.” She would reply
“Is it too revealing?” I would ask.
“Yes, it is really.”
“So what is it revealing?” I would press.
“Well, nothing, I suppose. But it’s definitely too short!”

And this is the thing: People consider a dress too short when all it is revealing is more leg. And these are the very people who, with the dress just 2 inches longer, thought these legs looked great! I suppose this isn’t surprising – there are many examples in life where the difference between good taste and bad taste, between right and wrong even, is just a matter of judgement. And I suppose that simple logic would suggest that if a hemline is so short that it would seem more sensible to measure it down from the waist than up from the knee, most reasonable people could well consider that too short.

You might think that, by now, there ought to be some quick, practical ways to gauge when a skirt is just not long enough, and indeed there are! If you stand up straight and hold your arms down at your sides with your fingers bent inwards and the tip of your index finger touches leg, not skirt, then that skirt needs to be longer. And this is not some arbitrary measure, for by an amazing quirk of evolution – or by ‘intelligent design’, as the more religious among us might say – your fingertips are at the same level as the bottom of your bum cheeks. So, if bare thigh is visible at the front… you know what’s visible at the back! And here there does need to be a difference introduced for those transvestites living life at the limit. In ‘normal’ circumstances this fingertip rule holds good at the front for shemales too, for keeping out of sight that-which-should-not-be-seen. But, given the risks inherent in a man squeezing himself into skimpy panties meant for a woman – the risks of ‘popping out’ after a sudden ill-judged movement, and of the soft rub of lacy fabric then making the problem, well, much ‘bigger’ – some additional margin is definitely required. In my own personal experience I would suggest going two inches beyond the fingertip rule, but we are each different, and a tranny should experiment to find the length that stops their friends putting in an unwanted appearance in these extreme circumstances.

Another good rule of thumb for determining when a skirt is too short – one that is eminently practical – is that, when you are tired out after a hard morning’s shopping and you find that perfect table in the corner of a cafe and you dump all your bags on the floor and sit down, you want to find that you are sitting on skirt fabric and not on your panties alone or worse , if you are wearing a thong, on just the bare wood of the chair!

There are other tests that, frankly, I would not bother with. The classic one is bending over but, I’m sorry, if you’re that close to ‘too short’, bending over is something you just can’t afford to do. Instead, you’re going to have to master that beautifully elegant, but actually extremely difficult technique of bending your knees while keeping them locked together, sinking down onto your haunches and then rising upright again, gracefully, without falling sideways. Either that or you’re just going to have to leave all your dropped loose change lying on the pavement.

The other test that’s not worth the trouble is seeing whether you can get out of a car without revealing your modesty. Technically, it’s possible in the very shortest of dresses. The best practitioners seem just to swing their legs sideways, keeping them tightly together of course, place their gorgeous stiletto heels onto the pavement and rise in one single movement. They might even hold out one hand in mid-air in total confidence that a bystanding gentleman will reach out to offer them a steadying hand. The rest of us, though, would make a complete dog’s dinner of this ‘move’: When the car door opened we would find ourselves too far from it for our legs to reach and we would have to shuffle forward from cheek to cheek. With our skirt already half up our backsides we would then find that we simply didn’t have the momentum to rise into a standing position. We would have to grab hold of either side of the door frame with our hands, elbows braced outwards, open our legs wide for extra stability and purchase and heave ourselves out and up onto the pavement, just as a waiting paparazzi, kneeling on the pavement in front of us, gets a perfect shot of our panties! You might think you could do a much better job of this but my advice to you would be to always have your driver stop the car just round the corner so you can clamber out and tug down your skirt before you head for the red carpet.

But let’s get back to our thought experiment investigating just how short is too short. Although we may be passing the point where most people would be happy to stop, we cross-dressers are an adventurous lot and I think we could learn something useful if we explore further. So, if a dress is commonly held to be too short even if in any practical sense it isn’t, at what point would a dress really, really, really become just too short? I don’t think it is appropriate to carry on with our experiment out in the high street so we had better go indoors. This change of setting is an important one. As transvestites we are all acutely aware of the difference between being ‘ourselves’ in our safe homes and going ‘out’ into the scary world at-large. Are we bound by the same ‘rules’ and social norms when we are alone, in front of our mirror or video camera as we are when we are in public. Of course we aren’t! We just love to strut about making the most of our fleeting femininity. We become theatrical darlings, relishing each little twist and turn, captivated by the beautiful woman looking back at us from the mirror or viewfinder. It is, of course, all about the clothes. We have bought that beautiful dress. We have purchased that gorgeous wig, we’ve invested in that stunning pair of heels and of course we have bought those exquisite little panties. And we jolly well want to show them all off! Safe in our rooms, we throw caution to the wind. We stand admiring our lovely stockinged legs stretching down below that oh-so-short dress and we wonder how much lovelier they would look if the skirt was just a little shorter still. We lift our skirt up higher and higher and there is that beautiful little lacy triangle peeking out. We lift our skirt right up – something we could never do in the real world – and admire their skimpy femininity stretched over our barely covered bulge. Away from prying eyes we might stand with one foot raised up on the bed or we might get down on all fours and crawl along like a pussycat, looking back over our shoulder to enjoy the view of our lacey-thonged rear in the mirror behind. This is us in seventh heaven!

And so, our values do change depending on our circumstances. Quite rightly, we would not dream of doing in the high street what we love to do by ourselves – we are very adept at tuning in to the social context. A short dress that we would feel fine in at a drinks party would make us feel uncomfortably exposed in the office but actually, when we were putting on a show for ourselves, we would feel it wasn’t short enough . And the same ‘tuning in’ is happening in the minds of those who see us. Take that same nice woman, for example, who we have just interviewed outside Tesco and who thought my dress ‘definitely too short.’ If I invited her to our drinks do then I think I could hitch my dress an inch or two higher before she would say ‘My, that’s a little short!’ And maybe, if she ever got an invitation to my inner sanctum, to sit on the edge of my bed away from all those social norms and influences and watch me putting on a show for myself, she would see how much pleasure I get from giving myself those little flashes of red lace, she would look at me and say, “You look gorgeous, Lilly, but do you think your dress should be, well… a little shorter?


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