XY - Why cross-dress?

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XY – Why cross-dress?

I have a friend who ….. oh no – here we go again – a pretence that this is not an autobiography.


This is perhaps the most personal piece I have posted yet. Well, I write and I enjoy putting words in a row. Some of what I string together is when my brain is deeply into my feminine life. At other times I am content just to wear the outer garb but to retain and enjoy the certainty that I am a male. After all, I have never even considered that I might want to remove my penis. I don’t love it as much as many males. But I do not hate it. I rather enjoy what I can do with it.

I have read that some homosexuals are ardently fond of their penises; I can’t say I ‘know’ because I am not gay (I’m barely happy on some occasions). Wooops, that was naughty and shows that I am an Aged Fart who has barely learnt political correctness.

I know which categories I belong to – I am middle-aged, mildly christian, white, male, heterosexual, married, intelligent, carnivorous, trans-interested, cross-dressing, cat-loving, ….. oh, white, quite well-off, socially inept, (ex-)rugby playing, non-smoking, average-drinking, never-druggy …… and obviously more. What I am limits what I can know about.

I have read about and I have been told about a variety of characteristics – but I cannot imagine myself into the required role.

To widen the list of the groups of which I have less than excellent understanding I can use the list above in reverse. I do not know about people who are old, young, black, brown or yellow, female, homosexual, divorced, dim, vegetarian, poor, millionaires, football fans, binge-drinking, and on and on.

To me, it is very useful to be willing and able to say ‘this is something I do not know’. These are known unknowns to use Donald Rumsfeld’s much criticised analysis.

So – I do not comprehend the need to make the transgender transition, I do not understand women, homosexuals. I have no real concept of the gender divide except from a one-sided view. I have never experienced being black, brown, yellow or any non-white skin colour. I know nothing about Catholic guilt, Jewish or Islamic pressures or the quasi-religious demands of cults and other fanatics.

As I move onward in my life, I have grown and learnt. I have begun to understand some of my attitudes and habits. Some I cannot understand – how is it that someone who is so involved in figures and patterns can never remember to make a mental note of the mileage at the beginning of a journey AND at the end. I can do sometimes it if I write it down. I can remember to check the dial within the first or last mile of a journey – but. I have one much-repeated journey for which I can take some 5 different routes of much the same mileage and duration. After several years I have not managed to analyse with confidence which is the quickest or the shortest or the easiest option to use most often. If I cannot do a simple task like that – then what more complex tasks can I prove to myself or to others that I am capable of.

I know the most overt of my socially unacceptable habits. I like to cross-dress. I enjoy cross-dressing. Sometimes I actually need to cross-dress. But I know that, at the very least maritally, this particular foible is not acceptable.

Can I understand this attitude? No.
Can I accept this attitude? Barely.
Can I give up cross-dressing ? I don’t think so.
What will I do? Be more careful and not get caught!
What about reading stories? Not acceptable either!!
The future ? uncertain ….. and a bit scary.

[tangent – I just saw a typo: I wrote the word ‘maritally’ as ‘martially’ which would have meant that I was referring to the armed services attitude to sexual and gender variation. No, ‘maritally’ – refers to my wife.]

Perhaps fortunately, my parents are both dead. My uncles and aunts are dead. My sibling is dead (lung and brain cancer at 49). I am self-employed but would find it difficult to deal with my clients as an overt ‘man in a dress’.

Socially, I have touched on sexual diversity with some friends but apart from a few who ‘have a friend who is ‘fill the gap’’ not one has opened themselves as regards any unusual habit or proclivity.

What can I tell myself about my cross-dressing.

I tried on my mother’s clothes a few times when I was a young teenager on holiday from boarding school. Did she catch me – once or twice. Did she say anything to me or do anything. Nothing was said. My father never said anything. To my recollection, nothing happened.

Years later, as my social incompetence continued and my unintended asexuality continued – I did become interested again in and eventually bought panties for myself, and tights. Despite sharing a flat with several girls, I never even thought of stealing their clothes (although all of them were nothing like my 6ft 12+ stone build.

Later still, I bought my own house. I think, and I don’t remember accurately, that I bought and wore panties, nighties and occasional items. I don’t recall wearing a dress or a skirt. My cross-dressing went on for so long that it seems likely that I did press my own boundaries. It may well be that I even went out wearing a dress or similar. I really cannot remember.

And in those days, the internet was slow, sluglike and therefore pictures and videos were outside my ambit. I did read stories for many years. I was content with just words-in-a-row. It’s still my preferred method of escapism. Put me in a heap with books, pen & paper, drink, food, maybe music and it may be that I will not move except for the toilet.

The internet has, extremely gradually, altered my interests. I have to agree that my habit has obsessive flavours, if not addictive. I know that I am easily obsessive. I refuse to have any games on my computer because I know that I could easily get myself locked into hours of late night gameplay. It happened on my brother’s computer in the early days of Apple – but I have avoided that display of weakness.

But I can drive myself to near exhaustion for a new and exciting project. For one or two or three weeks, even more maybe, I can ignore food, drink, sleep, duties and meetings for quite a time. This does feel like a near-addictive potential.

Oh dear, I keep drifting away from my main theme. Why do I like cross-dressing? Perhaps I need to go back to school and use an ‘essay plan’.

I like the feel of the clothes. Male clothes are alright for the purpose of covering my skin from the elements – but the only things I can ever remember enjoying are crisp, new shirts or new socks and my waistcoats. The waistcoats are perhaps my most obvious display of peacockery – after all there’s not much a modern western normal man can wear in public for enjoyment.

I love the feel of satin, of silk, of sheer, soft, slinky, slithery. I’m not sure about lace – because it is almost scratchy – but it is so pretty and feminine that I can put up with the mild discomfort.

I adore the pull and stretch of stockings or tights on my skin. There’s something very pleasant about the feel of the hem of my dress or skirt against the taut nylon that is very different but equally pleasurable as the feel of the hem against my bare skin.

I really get irritated with spaghetti straps sliding off my shoulders – but heck, how else do you get some of your camis and slips to stay in place. At least a bra has the complex arrangements of straps and elastics to keep it mostly in place. And having used a filled bra for many days in a row over the summer, the entrancing sight of the double curve of my own (yes – fake) breasts at the edge of my vision wants them to be there more of the time. I love having breasts.

And my clothes were discovered and destroyed. That was a mistake of awful proportions. Dreadful. Catastrophic. Almost irrecoverable. I dare not be caught again, yet I love dressing.

I used to buy clothes for my wife. She enjoyed it. But now, when I offer, a scowl crosses her face and I can see her thinking ‘you only want to do it as some sort of grubby equivalent of buying and wearing them yourself’. And my pleasure and her pleasure has been obliterated by her distatste at my unpopular activity.

I love the enormously bigger palette of colours that women can use. I don’t like all the colours and, if I knew my colour code, I would not use others.

I enjoy the materials – and again in the western world, the feminine range is fantastic. And I want to have my part of it.

I love the feeling of a woman’s clothes. And that feeling is deep inside me. My future, sadly, is at risk because of it. But it goes so deep that it doesn’t feel as if I have either control or choice.

But of course I have a choice – I can choose to surrender my pleasure and my leisure – and take on the camouflage of a normal. Yukk.



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