This is a work of FICTION for ADULTS only. Do NOT read this if you are under 18 or if you are not an adult according to the laws of your state or country. Do NOT read this if you are offended by fantasies involving sexually explicit material.

Written by Bethany Jacques. Comments welcome to bethjac@hotmail.com

 

That red dress started it....!                 by: Bethany Jacques

 

Part 1

Inevitably, after graduating, there were a lot of changes in my life. And in my lifestyle. I had never dreamed they would be so drastic though. And so much fun!

Not that I hadn’t had my share of fun in the previous three years, that is. On and off I’d had a great time. Living on campus the first year, with lots of other young impressionable teenagers. Both sexes. I’d been cloistered up until then but I came out big time, lost my virginity in the ladies’ loo of a pub in that October. To a woman twice my age and oh-so-attractive, I always did go for older women after that.

I settled down a bit after Easter in the first year, then went at it even bigger time in my second year, living in lodgings. And then calmed down, a lot, in the third year. Basically I worked. Not over-endowed with brain cells I knew I had to do that for a long spell before my finals. But I came through well, nearly got a first. Very nearly, apparently I was oh-so close but just under the borderline. But I did impress my professor. So much he agreed when I said I wanted to stay on for a Masters.

I had to find my own lodgings then of course. I thought I had that all sorted early on, got ahead of all the others looking for someone to live.

But at the end of August, just before going back for the Autumn term I struck lucky. I got a flat attached to a house, admittedly some way from the campus but it really was a nice setting. A ‘granny flat’ built for the owner’s mother but she had died a few months earlier. The couple there had decided to let it out rather that incorporate it back into their residence. They had another reason to want to do that. The owner explained to me when I had looked round and decided to take it.

"You see, Ben, my wife and I entertain a lot and quite often we are away at the weekends. So we need someone to be around, just to keep an eye on the house. Burglars, you know. If they know the house is empty, well ... At least with a lodger there will be comings and goings, the place will seem occupied. And of course we realise you need recompense. If you can take this on we’ll reduce the rent. How about it?"

When he said that I jumped at the chance. For all sorts of reasons, some of which I didn’t want to reveal. The money, though, would help. Lots. He asked for references of course, after all I was going to be entrusted with the keys to a very nice house with some rather valuable contents. But my professor came good, gave me a glowing report. I was in.

I moved in very early in September and got to grips with what was expected of me, tutoring students, getting started on my own research, beginning to set out my portfolio for submission later. A lot to do, it was a busy month with little social life. Most of my own friends from the previous year had gone but that didn’t worry me. I had work to do.

In fact it wasn’t until three weeks into term that I met my ‘landlady’. Charlie’s wife that is. They invited me round one Friday evening for drinks and nibbles, for a friendly get-together. She amazed me! In about eight ways at once. I was in love, immediately. The perfect older woman. Older than me that is but a lot younger than him. About 35 I reckoned, in fact she told me so later, I had guessed dead right. Charlie was 51, owner of a chain of stores across Brum and the surrounding area. Selling clothes mainly, men’s and women’s. Helena wasn’t a model but could have been.

Tallish, slim. Gorgeous figure, not afraid to show off her assets, when she held out her hand to greet me I had to move closer, and had to work very hard indeed not to just stare down her cleavage. And when she sat down, well, those legs in that skirt, wow. She looked good in anything, I imagined her in a ‘lbd’ - maybe not black. Red. Definitely. She would look sensational!

And very well dressed too. Skirt and top were obviously not chap. And the shoes, in that area I am an expert, I’d swear they were Italian and very expensive.

"Charlie gets lots of my clothes, Ben, from the shops or through his contacts. He’s very good to me, really, he’s the best husband ever". And to prove her point she leaned over towards him and kissed him on the lips, sliding her well-manicured hand round his bum. At that moment I would have given anything to be in his shoes.

I was a little nervous later when he went into the study to sort his e-mails, leaving us alone. Helena though had been reading the signals all evening and came straight out with it.

"Ben. Please don’t take this the wrong way. But I’ve been watching you all evening. Watching me. You need warning. Charlie is very jealous. He likes me to dress up, specially when we have company. And he doesn’t like other men watching me. But. Look but don’t touch. OK?"

I mumbled some sort of reply.

"Ben, I can tell. You’re a sweet young man. But despite the age difference Charlie and I are very happy together. Some of our so-called friends think I’m only after his money. That’s not true. I married him, ten years ago, for love and for money. "

I mumbled again, embarrassed my Helena’s honesty. At which point Charlie interrupted our conversation.

"Helena, I’ve had a message from Jim. Jim Harrison. Can we go down to the cottage in Poole with them next weekend again. Could be fun, have we anything on?"

"No darling, that sounds fine. Do you want to email Jim straight back? I’ll bring Katie that dress she wanted, you did get it didn’t you?"

"Yes I did, it came into the shop today. Okay, we’re on."

Mrs Warner - Helena - looked across at me.

"Looks like the first time you’ll be looking after the house, Ben. Charlie had better give you a proper guided tour, so you know what to look out for. How about Sunday? Evening? That OK?"

Indeed it was, the tour went OK. But not before I had spent almost all day Saturday preparing. Preparing what? Preparing for the next weekend of course. Some guys might have taken he opportunity to do something they shouldn’t. Like burglary? Not me. Like arranging a rave, a party, an orgy? Not me. Or just inviting a girl round for the evening/night, trying to impress her with the opulence of his house and lifestyle. Well, maybe I might have gone for that but I had a better idea.

Which is why that Friday night, after the drinks and before going to bed, I got down a large case from on top of my wardrobe. A locked case. And checked exactly what I had in it.

One pair of sheer black nylon stockings, unopened, seamed, very expensive, one of the two pairs I had bought in Paris on a visit at the end of the previous year (part of my degree course). A rash purchase at the time, but I had just HAD to have them;

One only slightly used lipstick, an extremely attractive, I thought, beep cherry red, very thick and creamy and glamorous, again bought on the same trip to Paris;

One lip-liner pencil, a shade just a little darker than the above, to heighten its effect;

One tube of lip gloss, to enhance the above even more;

Two somewhat older pairs of stockings, one pair a deep tan colour, the other black and thick-ish, 30 denier;

One black bra, size 38D for moments of wanting to feel voluptuous which, when I was indulging in my ‘hobby’, was all the time;

One pair of black silk panties, matching the above;

One wig, straight, longish, a deep-to-mid brown colour.

One pair of black high-heeled shoes, shiny patent, with ankle strap and a sensational 5" high stiletto heel.

It was a start. Actually not a start, it was just those items I had forgotten to or had been unwilling to throw away after a previous purge at the end of my course. But for now it was something to work from. And work I did, sitting down and actually committing to paper a ‘shopping list’ after I got back into my flat. A list of those items I was just going to have to have before Helena and Charlie left for their weekend away.

I had imagined what I would like to do the first time this happened. I knew I was serious, the very next day in the afternoon I had the chance of a ‘date’ for the coming Saturday night. A friend of a friend in the faculty actually sought me out, inviting me to a party she had heard about. She was nice, Jessica was her name if I remember properly. I hadn’t really fancied her though I do admit the chance of a social evening out in mixed company, drink and maybe some ‘fun’, was appealing. But I had decided what I was going to do. OK it was on my own. But I just knew I had to do it.

And over the next three days, after working in college, tutoring, planning my main project and generally helping my professor (always keep in with him, you’ll need a reference one day) I shopped on the way home. At Boots, and at ‘Miss Selfridges’. And at a local cheap clothing shop, and at a charity shop I had been eyeing for a while. Just in case. By the Thursday evening I was ready.

I had them all, at least enough for the occasion. Longish ‘unisex’ black leather jacket, not something I had purchased specially, but one which I knew would look the part. White sweater, short-ish dark denim skirt. And some assorted jewellery, mainly ‘gold’ and rather tartily chunky, earrings and necklet and a bracelet.

And the nails of course, not too long, stick on and a cherry red. A half hour after Charlie had driven off, at about 5.30, I was sat in my little bedroom, facing my mirror, just looking, and imagining. Wondering just how well I could do.

I set to it. Stripped and showered first, using a mildly scented gel and revelled in the heat and the fragrance of the experience. I had at that time a slightly hairy body, nothing like as much as most men but some, enough to spoil my experience if I left the situation untouched. I had on a previous occasion found a way round that - a slightly fragrant oil, just a tiny amount, gently smoothed over my arms, my chest, my whole body. After this I really was getting into the swing of it.

The black bra and panties came first as I began to ‘dress’, the former padded with two small water-filled balloons wrapped in old pairs of tights. The bra had quite full cups, and from the right angle the boobs and the panties looked good, my cock tucked tightly between my legs and the smooth knickers pulled right up. Black tights finished off the undies, then a tight-ish white ribbed sweater and short denim skirt, earrings and necklet, two rings on each hand, this was beginning to feel really good. Doing all this in the privacy of my own flat, with no risk of interruption from family, landlady, fellow tenants, I was relishing the opportunity.

I unwrapped my new purchases to augment my existing stock of make-up and set to with relish. The foundation I had chosen was labelled ‘pale peach’, difficult to tell what it was going to look like on. But only a few minutes later I was looking delightedly at the end results. It looked smooth, silky, not too heavy, yet it covered up any remaining trace of my facial hair. The blusher went on well, I was on a roll, then, eyeshadow, eyeliner, mascara, I did so like doing my eye make-up. I shaded in gently a sculpted pair of eyebrows and then sat back to look carefully. This was even more fun than usual. The wig finished off my look, followed by very careful application of my coloured stick-on nails. I slipped my stockinged feet into my high heels, Nearly finished. The deep cherry lipstick together with my lip-liner. Extremely delicately applied. Done!

I stood up. The heels felt good. The moment I started to move, to walk towards the tall mirror on the wardrobe door that sensational feeling, enlarged by the sensation of one nylon thigh sliding across the other. Wow! I couldn’t believe just how good this felt. And the mirror did not let me down. For the second time in my life - my fifth time of trying, I looked at a reflection of a woman. My mind slipped back.

The very first time had been about five years earlier, in my last year at school I had tried on my sister’s underwear and posed to look at myself in her bedroom mirror. It had been a television programme the previous evening which had exposed me to ‘transvestites’ - up to then I just didn’t realise they existed. And a couple of weeks later I had gone further, squeezing myself into her entire school uniform. For the first time I wanted to go out, to be seen, to be looked on as a girl, a female, a woman. But I stayed in and posed some more, too scared to expose myself to the outside world.

Occasion number three was quite some time later, about three years I think, again at home, visiting my parents at the end of a hard term. They had gone out for the evening, leaving me in on my own with the football on the television. Only this time I had gone for my mother’s things, underwear, a party dress she had which was rather tight on me. And heels. High hells. For the first time I felt the delight in wobbling at first, then becoming more confident wearing her strappy stiletto sandals. Again going out had not been an option, the shoes were really too small but I managed to re-fix the buckles and squeeze into them.

And the last time. Maybe six months earlier, for an evening’s relaxation in the middle of preparing for my Finals. Except it wasn’t relaxation really. I had been determined to do the job properly, to see whether I could really look the part. That was when I had bought some of my own stuff, the bra and panties, the wig and so on.

As I sat there in my own small kitchen, Charlie and Helena out for the weekend, no risk of being seen I did recall. The thrill of six months ago. Going out into the street, rather different there, outside my student lodgings, nothing like as secluded as this. Out into the street and for a short, sweet, delightful first walk in public. I’d been lucky, it had been a Monday evening, not too busy, it was just after 11 o’clock as I took my very first 200 yard stroll ‘as a woman’. Dark with street lights, I was sure no-one could possibly recognise me, not that I expected to meet anyone I knew.

And I was about to do it again. Dressed somewhat similarly but feeling more confident. I’d done this once after all, I could do it again. And I had my car this time, I could drive some distance, to an area where I was definitely not known. I sat and breathed deeply, fascinated by the rise and fall of my ‘breasts’. I unlocked my door, reached back to grab my handbag, checked for keys. And closed it behind me. I heard the lock click. Charlie’s garden lights had just come on, I stepped gingerly along the path, past the main house’s front door and unlocked my mini. I slid in.

It was a thrill to notice my skirt had slid up. Another to see that while the interior light stayed on I could see my hands, rings and red nails flashing, holding the wheel. I started up. The heels felt different now - obviously I’d never driven in them. But they also felt good. I pulled out of the drive and into the traffic, heading out of town and towards the suburbs.

I had my evening planned. Amazingly every one of the three parts of my plan worked. Perfectly. First to the bank, to the ‘hole-in-the-wall’ cash machine. I took out £30 with my credit card, and got another thrill as another customer passed me as I returned to my car.

"Evening" he said.

"Evening" I replied. I hadn’t at that time any indication of how my voice had sounded, aiming to pitch it just a little higher than normal. But - my very first words, well, word, to another person as a woman. Secondly to a shop. I was determined to do this. I had picked out a late-opening newsagents in a small arcade some distance from my flat. I didn’t exactly set the world on fire, just went in, grabbed a small carton of milk from the display cabinet, and paid for it. I was thrilled as I walked out. The woman behind the counter hadn’t paid me any attention at all. Again, sounds like nothing, but it was a first for me.

And the third occasion was a visit to the middle of town, parking at the end of Broad Street, walking down towards the shops and back again. Again just a couple of hundred yards, again doesn’t seem like much. Bur again, just being ‘in company’ as the late-night shoppers went about their business, as the businessmen who had been working late in their offices headed back to their cars, as just a few clubbers and ‘night-people’ began to make their way to the clubs and bars, I just mingled with them.

I drove back to the flat after that. The whole ‘outing’ had taken me just over an hour. That’s all, But as I changed back at my flat I was shaking rather, not from the cold but from the excitement of it all.

Over the next month or more I had two more chances to dress when Charlie and Helena were either away for the weekend or out for the night. The first time I didn’t do anything, my professor came up with some designs he wanted me to work on at short notice. But the second I did, I started where I had finished in walking through town, the same 200 yard stretch. I did move on, I had to, the whole point of ‘these sessions’ was to extend myself, to see how far I could go as a woman.

Phase two worked fine too. My little car wasn’t out of petrol, I had made absolutely sure of that before setting out. But the tank was half full, I reckoned I could easily fit £10 worth in. As I was filling up, at a service station I had visited a few times before, I realised that I was on camera! The video system there showed each of the pumps, maybe the cashier was even now looking down at me and admiring the woman he saw. But no, when I went in to pay it was an old-ish woman who took my ten pound note, hardly giving me a second glance. Still, I thought, I ‘got away with it’ again.

Phase three was due to be shopping, but things didn’t exactly go as intended! At a big superstore, the kind which sells virtually everything. I had intended to get a few items or ordinary shopping and groceries, then have a good look in the ladies’ clothing section. I really could go an awful long way, maybe trying on stuff, bras and tops and skirts and so on. But I intended to restrict myself, maybe buy a sweater and a couple of pairs of tights. I also wanted to go in the café there, maybe have a coffee and a pastry or something, try out my ‘femininity’. But it was on my way into the store from the car park, that’s where it went awry.

As I walked from my car towards the store I realised I had a problem. The excitement was getting too much for me. In a urinary sense that is, I just had to have a pee! I hadn’t taken proper care of that aspect of my preparation before going out and, with my penis somewhat constricted in my panties, I just had to go. Somewhere. I knew it had to be in the ‘Ladies’ in the store.

No problem, I thought, just go in, into a cubicle, do it, then walk out. It sounded easy. It should have been. Except for the ‘person’ I met in there. ‘She’ was just coming in as I left, I was amazed. I couldn’t believe nobody else had noticed ‘her’. It was a man! A transvestite. Hell, two of us in the same Ladies loo at the same time, just how many of us were there wandering round Birmingham that day? I decided the very best thing to do was to ignore ‘her’, get out of there fast. I was just about to, ‘she’ was starting to fix up her make-up in the mirror there when the door opened again.

 

To admit a policewoman!

"Just hold on a minute, please, we’ve had a rather strange report."

She was looking me up and down. Carefully. I began to shiver just a little, I was worried. And not too happy about being viewed so closely in such a position. I managed to turn - the transvestite was nowhere to be seen, ‘she’ had slipped rapidly into a cubicle.

 

"Excuse me, er - miss. May I ask, have you any ID with you?"

That was it. I was ‘read’. It was the ‘er’ in the ‘er - miss’ that was the giveaway.

 

End of Part 1 ....

 

 

© 2001
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.