Brandy Ch. 07-08

Chapter 7

THE DRESSERS

It's amazing how many men there are with a thing about clothing of one sort or another, either for themselves or for their partner and, sometimes both.

Of course, as I've said before, most men are more likely to be turned-on by something visual than the average woman is. For instance, there have been several attempts at launching magazines for women that include naked or semi-naked men, none have really been successful - compare that with the constant flood of 'girlie' magazines available on the market and you'll see what I mean.

So I can quite understand a guy getting turned-on by looking at a good-looking girl in something sexy - and don't mind admitting I often play on that to get a man going - and sometimes get a kick out of it myself. But I'm talking about the odd kinds of clothes that some men see as being sexy - not to mention the ways they then like to get off!

One of the best examples I can think of was a guy I saw about once a month for over a year. He always wanted exactly the same thing, never ever any variation. Nuns' habits were his thing - he may well have been a priest for all I know but somehow I doubt that, it's probably more likely that as a kid he went to a catholic school and got some sort of fixation about them then.

Anyway, he had two habits, his and mine, they looked genuine enough to me but then I wouldn't really know how to tell the genuine thing from just something he'd had made up. I had to travel to his flat, in quite an exclusive suburb I might add, a nice place, quite large, the furniture was a bit old-fashioned for my taste but well looked after and everything was always very neat and tidy. He'd let me in and once I knew the lay-out he'd leave me to find my own way to the second bed-room and get myself ready, while he went and changed in the main bed-room. Of course the first time I'd gone to see him he'd sat me down, offered me a drink and explained what he wanted me to do, when he'd finished I asked if that was all he wanted and with a sad little smile, he just nodded.

As I said, from then on I knew the routine - I had to strip down to bra, suspender-belt, stockings and high-heeled shoes, then put on the habit that was laid out on the bed for me, making sure I left just a little bit of hair sticking out from under the head-piece. He'd leave the agreed amount of cash in an envelope lying on top of the habit and every now and then, if he'd got something extra out of the performance, he'd leave a bit more in another envelope on a table just inside the front door - but I could never really see what it was that made the difference between a satisfactory and an extra special event for him. Apart from that first visit he never spoke and as I said, I never worked out why some times were better than others for him.

Once I was ready I'd go along to the main bed-room where I'd find him standing in one corner, waiting patiently for me to join him, at a casual glance looking exactly like a middle-aged nun.

I found that he didn't mind if I varied the start of the routine but once down to the serious part he wanted the identical sequence every time. So sometimes I walked slowly around the room, looking as though I was deep in thought, sometimes I'd just stand looking out of the window, sometimes I would sit for a few minutes.

But at some stage I had to notice the full-length mirror in the wardrobe door, walk over and stand in front of it and look at myself for a while - then seem to notice the stray piece of hair. I'd try to poke it back under the head-piece and when I couldn't do that I'd try adjusting the head-piece itself - and in doing that of course it would come off, letting my hair fall free. I'd stand looking at it, as though surprised to see so much of it, shake it from side to side, reach up and play with it.

By that stage, if I looked out of the corner of my eye I could tell from the slight movement at the front of the habit that he was starting to get excited. I'd worked out that underneath it he was naked and that what appeared to be pockets were merely slits, enabling him to handle himself while he watched me.

Once I was sure he was getting started I moved on to the next stage of the performance - looking down at my feet, lifting the hem of my habit a little, just high enough to show my ankles, then a little higher, a little higher. I had to do it slowly, tantalisingly, gradually increasing his rising level of excitement. When I finally had the hem high enough to show my knees I'd step back a pace or two, as though to get a better look at what I was seeing, lift one foot, then the other - then, gathering the folds of material in my hands, continue slowly lifting the habit higher still.

Usually at about that stage I'd hear him come - just a very faint gasp - once or twice I actually got the habit all the way up to my waist before he got himself off but normally he was satisfied long before that.

And that was it - that was all he wanted. I've no idea whether he had his habit dry-cleaned or whether he'd hand wash it himself - maybe he simply had a wad of tissues or something in one of his hands to collect the semen.

Then there was the guy I'm always reminded of whenever I go to the beach. His turn-on was to have me rub sun-tan lotion into him, in his hotel room!

After the first time, when I didn't know what his speciality was of course, I always made sure I packed a swim-suit when he booked me, sometimes a bikini, sometimes a one-piece - but frankly I don't think what I wore really mattered very much to him. Like the guy with the nuns' habits, his imagination provided most of what he needed, except than in his case it was my hands he wanted, not his own.

Once I had arrived he'd get out a big beach towel, spread it on the floor, put a bottle of sun-tan lotion beside it then go off into the bath-room and change into a swim-suit. When he was ready he'd stretch himself out on the towel and I would start massaging lotion into his back.

He had a good physique, with nicely defined muscles and as he liked me to take my time I actually found it quite pleasant doing it for him, relaxing in a way. As I worked my way lower down his back I had to ease his swim-suit down over the cheeks of his arse, massage the lotion into them too and then pull it back up again before I started on the backs of his legs.

Once I had finished his back I'd roll him over and start on his chest and by that stage he would usually have a partial erection, which would of course be very obvious beneath the thin stuff they use for swimming gear. As I massaged lotion into his shoulders and chest I'd keep one eye on its development and either slow down or speed up my progress depending on how solid it was getting. Once I was sure it was fully erect I'd slip my hands lower and as he lifted his hips up off the towel I'd tug his briefs down over them, releasing his cock.

Of course by then my hands would be really slippery from the lotion and the feel of them as I gently fondled his balls and stroked up and down the hard length of his shaft must have been really exciting for him. He liked me to masturbate him slowly too - and though he kept his eyes shut and his hands straight down beside himself the whole time his little charade was going on, he did respond quite normally in every other way.

Unlike most guys that want to be jacked-off rather than fucked properly, he didn't expect me to take his cock in my mouth, realising that I couldn't do that with it covered in sun-tan lotion - or maybe he just preferred the slick feel of my hands to being sucked-off. I must say that when he finally came both the amount he'd shoot and the distance it went were more powerful than most men I've known - but I never did get to find out just what it was that was going on his head while I was getting him there.

He and the guy with the nuns' habits were at one end of the spectrum of men turned on by what was being worn, they both needed very little in the way of props for what was going on in their heads. At the other end of that spectrum I'd put a man that I knew as Tony, what he needed was far more complex.

Our actual meeting followed a long phone call during which I was several times tempted to hang up on him, mainly because he refused to tell me how he had got my number. He said it wasn't important, I said it was. Anyway, to cut a long story short he offered me a larger than usual fee, just for a chance to meet me - and, when he suggested a well known restaurant as a suitable place, although I was still a little hesitant, I agreed.

When I had he then wanted to know what I'd be wearing and at first I assumed that was so he would recognise me - but then he wanted me to give him totally unimportant details, like the actual brand and shade of lipstick, the size and style of my shoes, where I had bought the dress I'd said I would wear, stuff like that. I very nearly called the whole thing off again but there was something about his voice that intrigued me, so I just told him that if he was that interested we could talk about those things when we met - that seemed to keep him happy - but he did insist on knowing my height, weight and dress size and to bring the conversation to an end, I gave them to him.

When we met a couple of evenings later I found he was in his mid-forties, only a little bit taller than me and quite slim, with very fine, almost boyish features and absolutely perfect skin. He turned out to be quite charming, extremely polite and attentive - but the thing that really impressed me was his personal grooming, I don't just mean his clothes, which were impeccable but also things like nails and hair - everything about him was immaculate.

Once he'd ordered drinks we started to talk and I soon found out that he had a really cheeky sense of humour and in no time at all he had me laughing. Later, as we ate we chatted about a range of things and quite soon touched on clothes and fashion, a subject I found he was keenly interested in, women's as well as men's and once that came up not only did he become even more animated, I also felt that he was watching me and my reactions more intently.

It was only when we were sipping coffee that he finally asked the question - but it wasn't the one I had been expecting.

'Do you ever take women as clients Brandy?'

Sex with women wasn't something that I particularly looked for but it wasn't something I had avoided either and there had been occasions when, with the right person and under the right circumstances, I had found it extremely enjoyable. So I answered him honestly.

'Not regularly - but from time to time, yes.'

'I know that my sister would love to meet you.' he said quietly.

'On her own, or with you?' I asked.

'Aah! How perceptive, I knew you were an intelligent as well as an attractive woman Brandy.' He paused for a moment or two, his cool grey eyes looking steadily into mine. 'Let's say together - but separately. Neither of us is really interested in threesomes.'

'If she is as interesting a person as you are Tony then it could be a very pleasant evening.' I said, deciding to follow my instincts.

'Oh I think you'll find that she is.' he responded with a grin. 'But, she likes her little charade, do you have any objection to dressing-up for the part?'

'It depends on what sort of dressing-up Tony.'

'Oh, nothing too strange. Men's clothes for instance?'

'I wouldn't mind that - but I don't have anything that is particularly masculine.'

'I'm sure you don't Brandy, I wouldn't expect someone as feminine as you are to have the kind of thing she likes - but I'm sure she has some things that would fit you very well.'

'That's why you wanted to know my size.'

'One reason yes. So?'

'Why not!'

He beamed at my reply. 'Why not indeed. When? Now?'

'Where is she?'

'We have a little apartment not too far from here actually.' He looked down at his watch, looked back up into my eyes and added. 'She'll be home quite soon now. We could surprise her.'

'All right - but it will be a little expensive Tony.'

'Ah, not only intelligent and attractive - but practical too, I like that.' He took out his wallet and simply asked. 'How much?'

I replied by saying that the price depended on exactly what was involved and for how long - but he didn't seem to be listening, merely separating a number of notes from the thickish bundle in the wallet, then having folded them, he discreetly slid them across the table to me.

'If, afterwards you think it should be more than that just say so Brandy. Money isn't the problem.'

Without actually counting the money I couldn't tell exactly how much he'd given me but from the look of things it was more than I would have suggested, so I just slipped the notes into my purse and smiled back at him as I said. 'That should be fine - but I'll let you know.'

Then he was all bustle, paying the bill, finding a cab and within minutes we were outside a very exclusive looking block of apartments. As we went up in the lift I asked him what his sister's name was. He gave me a wry smile then replied. 'Our parents had a very odd sense of humour Brandy. They actually christened me Anthony and my sister Antoinette but calling us both 'Tony' - mine's with a Y and my sister's has an I, you see?'

'Make's it easier for me though.' I answered with a grin.

The apartment was beautiful, everything I'd ever hoped that one day I'd be able to afford for myself but Tony didn't give me a chance to look properly around it, simply bustled me straight through into a bed-room.

'What my sister would like Brandy is for you to remove your make-up, shower and dress in whatever you like from the things you'll find in the wardrobe, there should be plenty to choose from to fit you. Your bath-room is through here.' he explained as he walked over and opened a door to an en-suite. 'Toni should be back quite soon but take your time, there's no need to rush. When you are ready just go through to the living-room down the hall, help yourself to a drink. I'm sure she won't keep you waiting long.'

'And you Tony, where will you be?'

'Oh, don't worry about me, I'll be around. But I'll wait until after you and Toni have enjoyed yourselves. Now, I think you'll find everything you need here, is there anything else?'

'No Tony, that looks fine. I'll look for something to wear first.'

'Oh, I forgot - she would prefer it if you didn't wear anything underneath, do you mind that?'

'Of course not Tony.'

'Good, I'll leave you to it then.' he said as he left, closing the door behind him.

I stood there for a few moments, wondering just what I had let myself in for, then, having quickly counted the money he had given me, decided it was well worth finding out - and opened the wardrobe to find that it was full of all sorts of men's clothing - business suits, casual gear, chunky sweaters, silky shirts and even a whole variety of shoes!

A quick check showed that the clothes were arranged in series, by size, obviously Toni liked her 'men' in a variety of shapes - and so I was soon able to find a reasonable selection of things that I could comfortably fit into. Having picked out a sharp looking denim outfit that had cap to match, a soft shirt to go under the jacket and a pair of shoes that fitted fairly well, I laid them on the bed and then went through to the bath-room to remove the outer traces of my femininity.

Once I had showered I pinned my hair up so I could get most of it under the cap and when I turned off the overhead light and stood looking in the mirror at the finished result I surprised myself at just how good I looked as a man - and, as I felt a small tingle of excitement running through me, hoped Toni would think so too.

When I went through to the living-room I found that the lights had been dimmed there already and music was coming from a unit on one side of the room. Nearby was an open cocktail-bar so I made myself a weak drink then walked across to the picture windows that dominated the far wall and as I slowly sipped I stared down at the spectacular view of the flickering lights of the city.

I couldn't have been standing there for more than a minute or two before I heard the soft voice behind me.

'Hello.'

I turned around and saw her - tall, slim and quite lovely, standing just inside the door-way, her face in shadow, her figure silhouetted by the stronger light from the hall-way behind her.

'Hello - you must be Toni. Your brother said I should help myself to a drink, so I did, I hope you don't mind.'

'I'm glad you did, I'm sorry if I kept you waiting too long.' she replied as she came forward into the light so I could see her better.

'Not at all, I was enjoying the view. It's quite spectacular from up here.'

'Yes, we enjoy it too, especially on a warm, moonlit night, sitting outside with a cool drink.'

By then I could see her properly, she really was quite stunning. Pale auburn hair, that was thick and full and had been cut in one of the latest styles; quite short on the nape of her long elegant neck but kept full over her ears and on the crown, falling forwards in a casual- looking, shortish fringe. Her face was almost too perfect, oval shaped with large, wide-set eyes which were either a light blue or a pale grey-green colour, it was hard to be sure in the subdued light. A straight, slender nose and below that a wide, almost too full- lipped mouth - that smiled quietly as she watched me studying her. And in that smile I saw reflected the strong family resemblance she had with her brother.

As she came slowly closer I saw that she was even taller than I had first thought, quite a bit taller than myself and even allowing for the fact that she was wearing high heels I guessed that without them she would be at least as tall as Tony. But her height gave her that elegance that really top-class models need and seeing the way she carried herself I wondered if she had actually worked as one at sometime.

But the dress she was wearing wouldn't have been paid for from just modelling fees, it was exquisite and screamed Italian or French Couture. It appeared to be a mixture of a fine wool-crepe and chiffon that though it hugged her slim body still swayed gently, not allowing the eye to follow its precise shape too closely. Not the kind of dress I would even feel comfortable wearing for a night at the Opera, let alone something I might slip into to meet an escort-girl.

'I'm so glad you chose that outfit, it looks even better on you than it did when I bought it, very saucy and really very sexy - if you don't mind me saying so.' she said as she stopped just in front of me.

'Thank you. It fits surprisingly well - but now, seeing the lovely dress you have on, I feel a bit out of place in it.'

'Oh, please don't. It's always been my lucky dress - nice things have happened to me when I've worn it - I didn't put it on to impress you, I just wanted to look my best for you.'

'You look sensational.'

'Thank you. Now, how about another drink, then let's sit and chat for a while. Tell me all about yourself - well, whatever parts you feel like telling me I mean.' she added with a knowing smile as she guided me to an arm-chair, made fresh drinks, then settled herself elegantly in another chair opposite to me.

And that's how we spent the next half hour or so, I seemed to do most of the talking, Toni prompted me with questions from time to time and whenever I asked her one she quickly brought the conversation back to myself again. She was particularly interested in the young men I had met in the course of business, what they wanted of me, how they reacted, were they shy, fumbling, how did I feel when, as she put it - I had their young bodies all 'steamed-up'. And as I talked I saw her eyes staring, almost unblinkingly, wandering over my body, trying to see beneath my clothes. And I don't mind admitting that as I talked and felt the intensity of her gaze increasing the small thrill I had felt earlier gradually grew and before very long I felt a moist warmth building between my legs and then spreading out through my body.