Lisa's Dream

by Susan Heywood

Part 2

 

That afternoon he said goodbye to his landlady, telling her, quite truthfully, that he had left Kennedy and Wise for another position and that he had been invited to share with a colleague at work. He returned to Miss Armitage's house and rang the bell.

The door opened and Jennifer once again greeted him. This time, however, she wore a blue blouse with long, full sleeves, buttoned cuffs and fashionable scarf neck. The blouse was cut to show her ample bust to perfection and Robert could not help staring at her in rapt admiration. With the blouse she wore a black pencil skirt which emphasised her hips. She wore barely-black stockings and her feet were slipped into black patent 3 inch high-heeled court shoes. She had a gold chain around her right ankle and a gold watch and bracelet. From her pierced ears dangled gold hoop earrings. Her blonde hair, free of the headband, tumbled in curls around her shoulders.

"Hello", she said, giving him a radiant smile as he entered the house. "I'm really glad that you have agreed to join us. I'll show you to your room and you can have a bath and change into something more suitable: then I can run through a few details, what you might call the house rules".

Lisa watched every movement in Jennifer's lovely body as Robert followed her upstairs to a large room at the top of the house. Jennifer motioned with her hand. "This will be your room. As you can see, there is an en-suite bathroom and dressing room".

Robert gazed open-mouthed: the room was overtly feminine in style and colour with pink satin sheets and bedspread, drapes and frilly curtain around the dressing table. Soft lighting revealed itself at the touch of a button and on the dressing table top was arrayed all manner of lipsticks, powder, mascara, perfume, make-up pencils and so on. Finally he observed two doors in one wall: one gave access to the bathroom, the other was closed and led to a dressing room.

"Now that you are here we can make some final adjustments to your wardrobe, although many of these clothes will fit without alteration. Since your response to the mistress's advertisement we have had a few weeks to prepare for your arrival and the final details you gave her on Friday morning completed the picture. I do hope that you will be happy with us". She again took and held Robert's hands, then kissed him full on the mouth!

This was the first time (apart from a rare peck on the cheek from his mother or an aging aunt) that anyone had kissed him and he was shaken, yet he responded instinctively. All Robert's thoughts and rationalisations took place long after that first kiss. He, of course, had no experience of girls and had no idea of what to do. When he had previously thought about relationships he had supposed that he, who had all his life wished himself to be female, would have a relationship with a man. He was unsure of this but the alternative was with a woman. Whilst he found this thought exciting he concluded that, if he were a woman then he could not have any sort of relationship with another woman. His mind was by now in a state of utter confusion. Jennifer's kiss was turning all his ideas on their head because he found himself being drawn to her as to a magnet.

Eventually the proximity of this beautiful woman caused him to relax and he unconsciously wound his arms around Jennifer's neck. Now he knew that feeling of passionate ecstasy that a woman gets when she is one with her lover and responds to a kiss!

"My, oh my!" Jennifer said, laughing, as they finally detached themselves from one another. "Very interesting indeed!"

Then Robert realised that this had been a test to see how he would react - and he had acted exactly as Jennifer had hoped he would!

Robert was breathless when Jennifer finally let go of him. She looked at him with her head slightly tilted to one side and a small smile playing on her luscious red lips. Robert was amazed that someone as lovely as Jennifer would want to kiss plain old Robert and missed the significance of the smile. Before he could think more about it, however, she grabbed him by the arm and started stripping him.

"The sooner you get rid of that awful stubble the better," Jennifer said as Robert removed the last of his clothing. "It was like kissing a hedgehog!" He was disappointed - he thought that he had made a good attempt at shaving that morning!

Just then a voice from behind made him freeze.

"Bring her to me in the drawing room at 8 o'clock this evening and ensure that my instructions have been followed to the letter!"

Jennifer curtsied as Miss Armitage marched out of the room and Robert was left to contemplate his future in the company of these women who were to play such a significant part in Lisa's new life.

Jennifer led him into the bathroom and ran a bath laced with a generous helping of perfumed oils. She told Robert to get in and soak, which he did with a will. He was enjoying the pleasant and relaxing atmosphere and had been daydreaming about Jennifer's breasts and being kissed again by her when she suddenly entered the bathroom wearing a white overall and carrying a safety razor and a wet/dry shaver. She proceeded to lather his face and shave him. This she repeated and then lathered his whole body and shaved it clean. Finally she stood him up, dried him, creamed and powdered him and gave him a long white satin wrap and some heeled mules to put on. The satin felt good against his hairless skin as he tied first the inside ribbons and then the belt. Back again in the bedroom, she manicured his nails and applied nail polish, saying "They will grow in no time at all and we can shape them properly". She also treated his toes in the same way.

She applied moisturiser to his face and then, when the nail polish was dry, said "Time to get you into some new clothes". It was then he noticed that all his male clothes had gone. He was never to see them again.

Jennifer asked, "Have you ever worn a corset?"

Robert stammered, "N-No".

"Well then, I have laid out some clothes for you which should reinforce your new status as a woman and will help to give you the feminine figure that I'm sure you have always desired."

So saying she produced a long lace-up corset and Robert caught his breath. What a beautiful garment! It was made of heavy satin, well boned and with 6 strong suspenders hanging from the bottom. His joy knew no bounds as he helped Jennifer fit it around his waist.

"This is especially designed to give you more rounded hips and bum and somewhere to put your boobs!" Jennifer smiled as she popped a pair of silicone breasts into the bra part of the corset. As she was so doing she remarked "Not as big as mine but satisfactory for now".

With that statement sinking in she told him to hold onto the foot of the bed whilst she pulled the laces in tight. More and more she pulled until Robert could hardly breathe, then she stopped pulling and deftly tied off the laces in a bow at the back. How thrilling it was to be wearing such a garment!

"You will soon get used to wearing the corset and we will tighten it regularly until you achieve your ideal waist size".

So saying, Jennifer took up a pair of white silk stockings which she rolled onto his legs, then clipped them to the suspenders of the corset. My goodness, thought Robert! How slim they made his legs look! He stood there for a moment just pointing his foot out as he had seen other women in department stores do when they were trying something on and loving the sight of it! (Other women! He suddenly realised that he was already starting to act and think like a woman!) The only thing that spoilt the appearance was that joke between his legs but that was soon covered as he put on the white silky knickers which Jennifer had produced. He noticed that they were very strong, like a pantie-girdle: they also had a sort of absorbent pad inside the crotch and he asked what it was for.

"It's a sanitary towel, otherwise known as a panty liner: we don't want you soiling your new underwear now, do we? Other women of your age have periods and many wear a tampon. You don't have the necessary place to put one so will wear a sanitary towel. You will wear one all the time to help remind you of your new status. It will also help to flatten that oversized clitoris you have".

He was starting to suffer from information overload but there was no time to consider the matter further because Jennifer was starting on his makeup. After shaping his eyebrows she started on the other items which adorned the dressing table top. Foundation, powder, eyeliner, eye shadow, blusher; all were applied with consummate skill. Robert could not see what was going on as he had his back to the mirror but noticed the subtle fragrance as each item was opened and applied to his face. Before applying lipstick Jennifer reached over and took up a shoulder-length curly auburn wig, which she placed on his head and then styled.

She led him by the hand over to the second door leading off the bedroom. From this, the dressing room, she now took a long white petticoat, with several layers of skirt, which she popped over his head. He thrilled to the touch of the fine material as it slid down his silk-clad legs. Then she took a long white dress out of the wardrobe and Robert's eyes nearly popped out of his head when he saw it. In his dreams he had imagined himself wearing such a dress. Oh, yes! He had seen one like it numerous times. He had seen the film 'Chitty Chitty Bang Bang' on television some years before and sat glued to the screen whenever Sally Ann Howes appeared. She had worn a gorgeous dress just like that. He had bought the video and played it whenever he had the opportunity just so that he could see that wonderful dress. And now, such a dress was his to wear! It was white as snow, full length and very tight in the waist. Jennifer undid the long back zip and helped Robert to put on the dress. He felt a tremendous thrill as the long skirt fell to the floor. When Jennifer zipped him up he found that the dress fitted perfectly. His padded hips and bum, together with the layers of petticoat, caused the dress to flare out at just the right places and ensured that it was a very good fit indeed. He felt so feminine and that was before he had seen himself in the mirror!

Meanwhile Jennifer had placed a satin sash around his waist, tying it with a large floppy bow at the back. She bade him sit on the stool while she fitted white satin 3-inch heeled shoes onto his feet.

He had never before worn women's' clothes. He had never worn utterly feminine underwear, beautiful dresses, had never had the pleasure of feeling his feet in 'proper' shoes. He was getting really excited by now and couldn't wait for Jennifer to show him what he looked like fully dressed. Just before she did so she squirted some perfume behind his ears, then fitted pearl cluster clip-on earrings to them.

Finally she showed him how to gather up his skirts, turned him round and led him to the long mirror. He nearly fainted with the shock of it. He was utterly overwhelmed by the sight of himself in that mirror. 'My goodness!' He thought. 'She looks absolutely stunning!' Then he realised that it was himself he was looking at! It was amazing what the combination of hair, makeup, a beautiful dress and 'real' shoes could do to a girl! And that waist, and those hips! 'That's right,' he thought, 'I am now a woman.' There was nothing of the old Robert in that vision of loveliness. He looked very pretty indeed!

All at once the feeling, that had been slowly but steadily building over the time that he was being dressed, finally reached its point of no return. Suddenly his body took control: a huge, all consuming event that left him stunned and speechless.

Later, in his bed, he reflected that, whilst he had previously brought himself to a climax when dreaming of wearing women's clothes, he had always imagined himself having a woman's genitals with which to perform and that the penis with which he achieved his orgasm was, in fact, inside him. The thing that puzzled him most, however, was that he never ever imagined himself making love with a man but only with a woman. Perhaps he was, indeed, a lesbian! Now he knew, though, why he was to wear a sanitary towel!

Jennifer stood away a little and watched him: she said nothing, but merely smiled dreamily to herself and kept silent. Robert didn't notice that Jennifer had 'drifted away': she was looking at Robert/Lisa in a totally different way and she was quite surprised at both the vision she had created and her own feelings towards that creature!

Robert eventually recovered his composure and looked with a glassy expression at Jennifer who then seemed to come awake. She went over and took his arm to steady him.

"Are you OK now, Lisa?"

Robert was thrilled at being called Lisa at last, both by the mistress and now by this beautiful woman, towards whom his feelings of gratitude knew no bounds. Although, was it just gratitude or the seeds of something else? He smiled at Jennifer and was again surprised when she came over to him and kissed him lightly on the cheek.

"Mustn't smudge your lipstick now, must we? I should get into trouble with the mistress! By the way, you look absolutely divine!"

With that she led him out of the room and, as he was unfamiliar with skirts and heels, she helped him down the stairs.

Jennifer led him into the drawing room and then showed him how to curtsey saying, "The mistress will expect it and you mustn't forget to do so". She taught him what to do with his hands, how to sit, how to stand, walk and many other things that had his head reeling!

At precisely 8 o'clock Miss Armitage came into the room. Robert curtsied as he had been taught, then, once again, his mouth dropped open as he took in the sight before him.

Harriet Armitage wore a denim long-sleeved shirt, denim trousers and brown leather boots. They were not male clothes for they were a perfect fit, rather than the 'if it touches, it fits' approach that men's clothes always have. The shirt was unbuttoned to show a hint of small but well-formed breasts which Miss Armitage clearly had no wish to hide (She was not wearing a bra). She also wore a large gold Rolex watch on her left wrist and a chunky gold chain around her neck. Her short hair shone in the subtle lighting of the room. Again she neither needed, nor wore, any makeup.

"My word, Lisa, what a transformation! And that waist! Really Jennifer, I congratulate you! Well, Lisa, did you enjoy your initiation into our household?"

Robert nodded dumbly and bobbed a curtsey.

"Splendid!" cried Miss Armitage, clapping her hands. "Before we go any further I will tell you that you will henceforth be known only as Lisa. There will be no further reference to that other name by which you used to be known in your former life, nor, for obvious reasons, will you ever again be referred to as 'HE' or 'HIM'.

"Now, you may be wondering about the nature of the clothes that you are wearing. I like to see my girls (Robert completely missed the plural in this statement) in beautiful clothes, such as soft feminine blouses, long skirts, often long dresses when they are off duty. The more feminine looking, the better I like it. As this is your first night with us I thought that you would love that adorable white gown, am I right?"

"Y...yes, ma'am", Lisa stammered and wondered if she would ever feel as wonderfully feminine as she did that evening. To know that she was to spend several hours in those heavenly clothes made her loins start to tingle again.

Miss Armitage spoke again.

"It is time for Jennifer to go up and change and then we will all sit down for a quiet evening and get to know each other. Please sit, Lisa, I suggest that upright chair would be more suitable for you as you are wearing a corset".

Lisa curtsied again and did as she was bid. Miss Armitage smiled and lounged on one of the settees. She was very pleased indeed: Lisa made a lovely girl and would surely be an ideal addition to the household. She was both eager to learn and eager to please.

Miss Armitage then proceeded to tell Lisa her plans for the future. As each stage was explained to her she gasped with astonishment. After half-an-hour she was in a total whirl, trying to get her mind around all the many things that were to happen to her. Her mistress firstly told her that she would be regularly treated, as required, by both Jennifer and a beautician for waxing, electrolysis, manicure and pedicure, eyebrow shaping and trained in the use of make-up. Jennifer would teach her the skills of homemaking, cookery, sewing, dressmaking, deportment, speech, colour and style .......the list went on and on!

A little while later Jennifer came back into the room and Lisa was once more treated to the sight of this beautiful woman in another outfit. This time, however, her long, sleeveless dress was in the palest mint green. At her neck she wore a stylish chiffon scarf. The dress was very well fitted and, as before, did nothing to hide the swell of those wonderful breasts, her tiny waist and her full hips. She wore white court shoes with 4-inch heels and her shining golden hair was piled high onto the crown of her head and adorned with a sparkling tiara. A beautiful gold chain necklace with a large cameo pendant matched her gold pendant earrings.

Lisa wondered if she would ever again see Jennifer looking so beautiful. On impulse she stood and hugged Jennifer, whispering, "You look enchanting. What a beautiful dress."

Jennifer smiled, took the chair next to Lisa and marvelled at the natural way that Lisa was already slipping into feminine ways, mannerisms and thought and speech patterns. She had already told Lisa that women use different words from those that men use. Words like 'enchanting', 'gorgeous', 'heavenly' and so on slip easily and naturally into a woman's vocabulary and Jennifer was delighted to hear Lisa use these expressions in an apparently unconscious and natural manner. She took Lisa's hand in hers and squeezed it reassuringly as if to say "you're doing well" - but she didn't let go!

Miss Armitage smiled to herself and considered the results of work well done. In addition to finding a good, reliable assistant for her business enterprise, she felt sure that she had found an ideal companion for Jennifer. There were, however, a few surprises still in store for Miss Lisa Pemberton!

"It is time" said Miss Armitage to Lisa, "to explain to you the nature of your duties and the timetable of the household activities. Jennifer usually spends her mornings doing the housework: shopping, cleaning, washing, ironing, etc., after which she changes out of her work clothes and does some dressmaking or other activity. She absolutely adores keeping house, cooking and dressmaking. In fact she made those beautiful dresses that you are both wearing.

"In order to put you in the correct frame of mind for work - I will show you the office tomorrow morning - you will wear clothes appropriate to a personal assistant in business. It might be a skirt suit, blouse and skirt, a day dress in the summer, and so on. Jennifer will select what you wear each day as she knows how I would like to see you dressed. I am sure, however, that our choice of clothes will always make you feel very feminine and at the same time will teach you what colours and styles will most suit you. In the evening, as you have seen, you will change into something appropriate. In addition I frequently entertain guests and you will be required to assist Jennifer with her role as hostess for these functions: the exact duties will be explained later but I am certain that you will also enjoy this aspect of life in this house."

Lisa was intrigued but, meanwhile, certain feelings were again starting to get the better of her and she hoped that her mistress would soon finish so that her embarrassment would not show.

"I can see that you are feeling some excitement as a result of wearing that delightful dress, Lisa, and no doubt also at the prospect of living and working in a female role. Don't worry, it comes as no surprise to me, I was expecting it. Very soon, of course, medication will deal with this; meanwhile, Jennifer will look after you."

Jennifer rose and took Lisa in her arms. It seemed incredible that this wonderful pleasure should be hers after so many years. The delight at again being enfolded in the arms of the beautiful Jennifer, to smell her fragrance and to press against those breasts sent thrill after thrill through her body to enhance the shock waves already overtaking her.

She lightly kissed Jennifer as a 'thank you', turned to her mistress, curtsied and said shakily, "Thank you, ma'am. I am very grateful to you both and I will do my very best to please you".

"I know you will, my dear," Miss Armitage said as she rose from her chair and took Lisa's hands in hers. "Jennifer, you may bring supper now and then we will all retire. Lisa and I have a busy day ahead of us tomorrow."

Jennifer returned to the room a little later bearing the supper tray but Lisa was too excited to be able to eat or drink anything. She was still overwhelmed by the transformation that had taken place in a mere half-day.

A little later Jennifer helped her to prepare for bed. She bathed and was shown how to dispose of and replace her sanitary towel, which she now had to wear at all times. She was laced into another corset, lighter than the other and designed for nightwear, and given a beautiful long-sleeved white satin night-dress. She removed her makeup and replaced it with a night moisturising cream. Jennifer showed her all these things, then tucked her in and kissed her goodnight. Lisa's mother hadn't bothered with a goodnight kiss but this was a different sort of goodnight kiss to that which a mother would give. She became excited yet again when she felt Jennifer's tongue exploring her mouth. Before she had time to react, however, Jennifer smiled then turned out the light and left her, closing the bedroom door. She contentedly settled down in the satin sheets and, thinking again of Jennifer, drifted off to sleep.

The next morning at 7 o'clock Lisa was awakened, like Cinderella, with a gentle kiss. She had slept very well, feeling totally at peace for the first time in many a year. Following a visit to the bathroom, during which she washed and thoroughly shaved, Lisa began the intensive treatment that was to change her body for ever. Firstly Jennifer massaged special oils into Lisa's body and applied moisturiser to her face. Then she gave her a small capsule which she washed down with a glass of water. This, Jennifer explained, was a twofold assault on Lisa's maleness. The massage and oils were to help develop a smooth skin: the capsule was a hormone concentrate, which would help her to develop a female shape, skin texture and so on. Lisa was very excited at the prospect before her but still a little anxious. She decided that she must speak to Jennifer very soon about the ultimate result of all this treatment.

Lisa was then prepared for the task awaiting her that morning. Jennifer was wearing her black and white outfit and now Lisa could see that this consisted of a white vee-neck blouse with long sleeves, over which she wore a black pinafore dress. This had a tight waist and straight, knee-length skirt. It clearly had to be specially made in order to fit so snugly around Jennifer's ample bosom. (Then Lisa remembered that one of Jennifer's interests was dressmaking: this could then be one of her own creations). Her glossy black tights and black 2-inch heeled court shoes showed her lovely slim legs to perfection. Her hair was once again gathered into a white headband.

Jennifer explained, "Today you will be dressed for your first day at work."

The tight-laced corset, knickers and honey coloured stockings were to be her regular foundation for some time to come. Jennifer then applied makeup but this time told Lisa what she was doing and gave her little tips as she did so.

And now for the rest of her clothing. As Lisa put on her blouse and did up the buttons she finally admitting to herself that she had arrived! She really was now a working girl getting ready for her first day at the office and wanted to look pretty for her new boss. Her mid-calf length pencil skirt, in a stunning burgundy colour, was the height of office fashion. It was zipped and buttoned at the waist and had a matching lined long-sleeved jacket. Jennifer again fitted the curly auburn wig to Lisa's head and brushed it out. Small stud earrings, fine neck chain, watch, bangle and rings completed the jewellery and then Lisa watched in open-mouthed astonishment as Jennifer picked out a pair of black patent shoes from the cupboard.

"Try these for your first day; the mistress will just love them!"

That's all very well, thought Lisa, but the heels must be at least 4-inches, I'll never walk in them. She put them on, however, and then looked at her reflection in the long mirror, particularly admiring the way the very high heels helped to give her legs a lovely feminine shape. Again there was that feeling of warm excitement and she started to cry with joy at the thought that it really was Lisa looking back from that mirror. Not a photo or poster, but Lisa herself!

Jennifer held out her arms and Lisa gratefully flung herself into them, sobbing with delight. After a while she felt intoxicated by the nearness and fragrance of Jennifer and their lips seem to find each other like magnets. Very soon the two of them were locked in a passionate embrace made all the more sensual by the feeling of Jennifer's hands gently caressing Lisa's body through the satin blouse. No words were spoken or needed as they stood revelling in the joy of each other's company. The practicalities of a relationship were of no consequence at that time, save that each found the other attractive and wanted to share each with the other. Later, at bedtime, Lisa lay awake and thought about her feelings for Jennifer. Was she, in fact, a lesbian in all but genitals? Or was there some other explanation that had so far eluded her? All she knew for certain was that she had fallen head-over-heels in love!

After what seemed like hours, although only a few minutes, Jenny (as she insisted on being called) said "I'd better repair our makeup, the mistress will be expecting us and woe betide us if we're late!"

With that done she dabbed some perfume onto Lisa's pulse points, she put on and buttoned the matching burgundy jacket and they went downstairs, with Jenny again helping Lisa to negotiate the downward route.

Jenny led Lisa to the drawing room where Miss Armitage was waiting for her.

"Ah! Good morning, girls."

"Good morning, ma'am," they replied and Lisa was thrilled at being addressed in this manner. To curtsy in the skirt and shoes that she was wearing was difficult but she made the effort anyway.

Miss Armitage obviously didn't pick her up on it because she continued. "You look delightful, Lisa, and I love the shoes; very suitable for your first day in the office."

Lisa turned to Jenny and they exchanged knowing little smiles.

"This morning I will introduce you to the work that I require to be done every day. I know that you can type, I watched you in the office, practising at lunch times when you thought that no one was looking," said Miss Armitage, "I think that you will be putting those skills to good use in my employ."

After breakfast, Miss Armitage took Lisa and showed her the office. It had a very modern feel to it, including a 'state of the art' computer system.

"You already know most of this from your previous employment. There are, however, a few differences in the procedures that I use and we will go through these later. Meanwhile I would like to test your shorthand and typing skills."

With that, she indicated a pair of office chairs and Lisa sat straight-backed upon one of them. She marvelled at how easy it was to sit upright and then realised that this was entirely due to her tightly-laced corset! Miss Armitage handed her a shorthand notebook and pencil and then, taking the other chair, started to dictate.

"To Messrs. Brookes & James, Solicitors. The address is on file. For attention of Ms J. Smithson. Dear Ms Smithson, I acknowledge receipt of your letter.................."

Miss Armitage dictated slowly at first so that Lisa could keep up, and then waited while the letter and envelope had been typed. This was unnerving; being watched by her mistress, but Lisa persevered and completed it. All seemed satisfactory and so, after dictating a further four letters, showing Lisa the other documents awaiting attention and ensuring that she knew her way around the computer system, Miss Armitage said "I shall leave you for a while. Jennifer will prepare refreshments at lunchtime and you may have your break together. I will return later to sign those letters". So saying, she left Lisa to begin her work.

When Miss Armitage had gone, Lisa marvelled for a moment at her transformation and complete change of lifestyle! On Friday morning, just 4 days ago, she had been a nondescript male accounts clerk. Now she was a female Personal Assistant living in the same house as the beautiful Jenny and the enigmatic Miss Armitage!

 

To be continued……………….

  

  

  

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© 2004 by Susan Heywood. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.