CHAPTER ONE

 

My wife was insistent that I should take part in the fancy-dress ball to be promoted for charity by a club I used in Soho. I had mentioned it casually without any intention of entering myself. I had told her that all the tickets would cost ten pounds and that all the takings would be going to charity. It had been decided by the committee of the club that all the men should go dressed as women and all the women as men.

'It's an excellent idea,' said Margot. 'I think you'd look good dressed as a woman.'

'Make a damned fool of myself, more like,' was my reply. 'My hair's too short and thin for one thing and I haven't got the foggiest idea about making up.'

'Don't be silly. Those are not problems. I've got a wig you could wear and I'd do the making up for you. No, you might look really fetching. At least you have a decent figure.'

I put up a number of other arguments why I felt the idea was absurd, but she was quite insistent.

'I'd like to go myself,' she said, 'and that's why you are going.'

'But Margot, be reasonable. I'd look like a fool and I'd never live it down. I'd be laughing-stock for months.'

'Well, even if you were what would it matter? That would apply equally to all the others. But I really don't think you would. I'd think out the best outfit for you - the kind that would suit you best - and with a good wig and proper make-up I'm quite sure you'd cut quite a figure. Certainly you wouldn't look ridiculous. If I thought you did, then we'd find a last minute excuse and we wouldn't go.'

It was that that decided me. I knew that Margot would be able to judge how I looked and that she was telling the truth when she said that we wouldn't go if she thought I looked ridiculous. So we bought the two tickets and I thought no more about it until a couple of days before the party.

 

I reached home about five-thirty and Margot said that she had got the things ready for me. 'I think we ought to have a rehearsal,' she said. 'Let's dress up after dinner.'

I agreed that a rehearsal was a good idea. I felt sure that when she'd done everything possible to make me presentable she'd have to admit that it would be better if we didn't go and give up the idea.

As soon as dinner was over we went into the bedroom and Margot told me to strip. 'There's no problem for me - I can just put on some of your things - so we'll concentrate on you.'

In a moment or two I had stripped and waiting for Margot to start on me.

I had never put on any item of women's clothing before and, to tell the truth, I hadn't the vaguest idea how to go about it. Of course I had noticed my wife's clothes and some I preferred to others. Like most men of my generation I preferred to see a woman in stockings to seeing one in tights and I was always pleased when I saw Margot roaming around the house in a bra, suspender belt, knickers and stockings. As far as I was concerned, I felt that tights would be much the best thing to wear. I'd feel more 'dressed' and safer for one thing! But Margot was adamant that I should go as what she called a femme fatale.

'You must look the part and dress the part," she said. 'As I'm bound to use a fair amount of makeup on you to hide your blemishes, we may as well go the whole hog: false eyelashes, heavy makeup, dark eyes - the lot.' And then she added: 'and that means suspender belt and stockings.'

I couldn't see why it did for surely no one was going to look under my dress or my skirt to see what I was wearing underneath. But Margot's idea was that I should 'live out' the part fully. 'It's no use doing the thing half heartedly,' she said. So I was told to put on the suspender belt first of all. That presented no problem but when it came to the stockings she had to show me how to pull them up properly without laddering them. In the end I got the idea and when I had fastened them to the suspenders, I got to my feet and tried to get an idea of what I looked like. It was my legs that I thought would show me up more than anything else.

To my surprise they didn't look at all bad and Margot confirmed this. 'In the thirties,' she told me, 'the most fashionable legs were heavier than the type most admired today. Models' legs nowadays are much slimmer, sometimes almost without any contour. So you're in the fashion!' She laughed and then went on, 'No, joking apart, you've got quite good legs, I told you that before. Not so muscular as those of most men. Lucky you!'

Well, it was some small comfort to know that my legs would pass muster. I had really been horrified at the thought of my legs in stockings. I had seen one or two men in drag in south London pubs and it had always been their legs that gave them away. A man can wear a wig and pad out his bra, but he can't do much about his legs, except, perhaps, wear two or three pairs of stockings at once.

Apart from being pleased at what my wife had said about my legs I was quite enjoying the 'feel' of the nylons and especially the tug of the suspenders as I walked about the room. These things gave me what I can only call a 'sensual' feeling. Nevertheless I felt rather 'silly' wearing these two items of women s clothing. I wondered what my friends would have thought if they could have seen me at that moment. I'm sure they would have used some quite abusive comments about my being a 'poofta' or something of that kind!

My genitals ware hanging down beneath the suspenderbelt and between my stockings and my wife was quick to hand me a pair of knickers. 'Knickers are a different shape,' she said,' from a man's underpants, I suppose because a woman's bottom is very different from a man's. But they're a fairly large size and should so the trick.' The pair she handed to me were in a soft lilac colour and matched the bra I was to put on next. I pulled them up my legs and drew them tight in my crotch. Owing to the special shape of a woman's knickers they did not wholly cover my genitals. I must admit, however, that I have a rather large scrotum and a not insignificant penis!

I liked the feel of the knickers and when I looked at my bottom in the mirror I got the impression that knickers did something for me, somehow giving me a better shape in that quarter. My wife then explained that it was better to wear knickers over the suspenders, instead of putting them on first. 'Much easier when you go to the loo,' she said. I could see her point.

'Now for your bra,' she said, showing me how to put it on. I slipped first one arm and then the other into the shoulders straps and then drew on the garment. Then I reached round to fasten the clasp at the back. 'You may as well do it yourself so you'll know how,' she remarked, a faint smile on her face.

'So I'll know how?' I queried. 'Why do you think I'm going to wear a bra again?'

'You never know,' she laughed. It was a joke at the time but I have never forgotten that moment.

Once I had the bra clasps fixed Margot got four stockings and bundled two into each bra cup to give me what looked like two prominent breasts. When I looked at myself in profile I was quite impressed by my 'shapeliness'. I had a weakness for breasts anyway, and I was going to dress as a woman with a decent bosom if I was going to dress as one at all! I don't go for flat-cheated women and I find them unprepossessing.

'You're taking on quite a feminine appearance even at this stage,' my wife remarked. 'Come, let's try a wig on now so that we can get an all-round impression.' She produced two or three wigs from her collection and suggested one with black hair, a fringe and shoulder length. 'This is the one that I think will suit you best. I think it will really transform you, you'll almost be unrecognisable in it.'

She put it on my head, adjusted it carefully and then told me to look on the mirror. When I did so I had to admit to considerable surprise. It made all the difference and I could almost see anyone who didn't know me thinking that my face suggested that I was a woman! Framed by the hair my face took on a softer feminine aspect and I could already see that with the judicious use of make-up I might really look like a woman.

'You look quite pretty,' my wife remarked. 'Well, not so much pretty as attractive - almost desirable.'

'Oh, don't be stupid!' I said.

'No, really, I'm serious. I knew that you could look quite womanly when you were dressed in women e clothes and wearing a wig, but I really didn't think you'd look quite so good. I'll have to watch out in future!'

I pretended to be indifferent, even annoyed at what she was saying, but secretly I was rather flattered. Did I really look like a woman? I asked myself. In a way - and I couldn't understand why - I was rather pleased with my discovery ...

We didn't pursue the full dress rehearsal for as I sat on the bed my wife came over and began to feel me under my knickers. I was quickly aroused and it was no time before she was lying on her back with me on top of her. For some reason I got a special 'kick' out of making love to her and having intercourse dressed in women's undies!