Take a Letter, Jenny Part Two – Jennys Story

┬áTAKE A LETTER JENNY PART TWO – Jennys Story

Saturday was so frenzied that Jenny never had the time to think too much about the humiliation of serving complete strangers whilst dressed as a maid. Lisa was constantly sending her scurrying off to prepare vegetables or mix sauces. When the preparations for the meal were complete, Jenny was ordered to continue cleaning the house and, following an inspection by Lisa, was summoned to her bedroom.


“Ah, there you are! I want you to help me get dressed for this evening. Select my underwear while I have my bath. Oh, and iron my dress… but be careful.”


Jenny picked up the turqoise and black patterned taffeta dress and gazed at it with envy. It was sleeveless, and cut to reveal the shoulders, emphasising the feminine neck of her mistress. The bodice looked fairly tight, but the lower half of the skirt swirled out to end at mid calf. Jenny stood in front of the mirror and held the dress in front of her, romanticising about the feeling of glamour it could provide. Reluctantly, she tore her gaze away from the mirror, disconcerted that such girlish feelings could be coming to the surface so easily.

Ironing the dress was a nightmare. Jenny’s nervous fingers had to work as gently as possible to prevent the dress from being ruined by the heat of the iron.


After mincing back to her mistress’s bedroom, Jenny proceeded to select the most sensual and delicate lingerie. She chose very pale blue silk stockings with a little butterfly pattern just above the heel. Matching high heel shoes were added, followed by beautiful white satin French knickers with dainty lace trim, a wispy white lace basque for utter femininity.


Jenny laid the garments gently on the bed, again feeling twinges of envy and wishing she could be allowed to look so seductively glamorous.


When Lisa returned from her bath she seemed pleased with the selection Jenny had made. She gave her a little pat on the buttocks as a sign of approval and Jenny blushed with pride. Lisa let the towel fall from around her, revealing her naked body, with no apparent thought for Jenny’s presence.


Jenny proceeded to help her slip on the garments one by one, trying hard to control her excitement – partly because she was afraid of what punishment might ensue and partly because she didn’t want to be reminded of her maleness.

Lisa finally finished dressing, and Jenny gasped. Her mistress looked so gorgeous, so utterly, delightfully feminine!

“Now then, my pretty little shemale maid. How can we make sure you turn out to be the belle of the ball? Get undressed!”

 


 

 

Saturday was so frenzied that Jenny never had the time to think too much about the humiliation of serving complete strangers whilst dressed as a maid. Lisa was constantly sending her scurrying off to prepare vegetables or mix sauces. When the preparations for the meal were complete, Jenny was ordered to continue cleaning the house and, following an inspection by Lisa, was summoned to her bedroom.


“Ah, there you are! I want you to help me get dressed for this evening. Select my underwear while I have my bath. Oh, and iron my dress… but be careful.”

Jenny picked up the turqoise and black patterned taffeta dress and gazed at it with envy. It was sleeveless, and cut to reveal the shoulders, emphasising the feminine neck of her mistress. The bodice looked fairly tight, but the lower half of the skirt swirled out to end at mid calf. Jenny stood in front of the mirror and held the dress in front of her, romanticising about the feeling of glamour it could provide. Reluctantly, she tore her gaze away from the mirror, disconcerted that such girlish feelings could be coming to the surface so easily.


Ironing the dress was a nightmare. Jenny’s nervous fingers had to work as gently as possible to prevent the dress from being ruined by the heat of the iron.

After mincing back to her mistress’s bedroom, Jenny proceeded to select the most sensual and delicate lingerie. She chose very pale blue silk stockings with a little butterfly pattern just above the heel. Matching high heel shoes were added, followed by beautiful white satin French knickers with dainty lace trim, a wispy white lace basque for utter femininity.

Jenny laid the garments gently on the bed, again feeling twinges of envy and wishing she could be allowed to look so seductively glamorous.


When Lisa returned from her bath she seemed pleased with the selection Jenny had made. She gave her a little pat on the buttocks as a sign of approval and Jenny blushed with pride. Lisa let the towel fall from around her, revealing her naked body, with no apparent thought for Jenny’s presence.


Jenny proceeded to help her slip on the garments one by one, trying hard to control her excitement – partly because she was afraid of what punishment might ensue and partly because she didn’t want to be reminded of her maleness.

Lisa finally finished dressing, and Jenny gasped. Her mistress looked so gorgeous, so utterly, delightfully feminine!

“Now then, my pretty little shemale maid. How can we make sure you turn out to be the belle of the ball? Get undressed!”


Jenny did not know what to say. She felt that Lisa had deliberately trapped her, but at the same time she found the prospect quite thrilling.

 

“Yes, all right… but I’ll have to get permission from my mistress first.” she said.

“Don’t you worry your pretty little head about that. Leave it to me. I’ll take you to an excellent little Italian restaurant I know. I’ll come and pick you up on Wednesday at eight. Make sure you look as gorgeous as you look tonight.”

The rest of the night went by in a haze and, before she knew it, Jenny was helping the guests with their coats and curtsying to them as they left.

As she was tidying up, she noticed Lisa staring intently at her from the other side of the room. “Did you enjoy yourself tonight, Jenny?” she asked.

“Oh yes, mistress. I hope I served your guests well?”

“I think you did a very good job of keeping my guests happy.. especially Steve.” H er tone was gently mocking.

“Thank you mistress,” said Jenny. She meant every word of it, although she did not want to admit, even to herself, that the thought of being romanced and fussed over by a handsome young man could cause her heart to flutter with feelings of submissive bliss.


Sunday went by very quickly, as Jenny was kept busy with a variety of household chores. She woke early and changed from her pink satin nightie into her original ensemble. Dressing as a girl felt completely natural now, but although Jenny could have dressed in a matter of minutes she took her time with each item of clothing. It was so pleasurable to feel the smoothness of the stockings, the tightness of the corset and the soft, feminine rustle of the petticoat. She hummed to herself as she placed the apron around her waist and tied the large bow.


Suddenly she realised that she would have to make herself up for the first ever time. She tried to remember the routine that Lisa had followed and went over to the dressing table.

She usedlong, even strokes to get an even finish to the foundation. The eyeliner was much more difficult, and she needed several attempts before she obtained the right effect. She chose a very subtle light blue eyeshadow and added a hint of blusher high on the cheeks. After some hesitation, a coral pink lipstick was applied and Jenny gave herself a pout of satisfaction in the mirror.


She slowly placed the beautiful auburn wig on her head and, even though the effect was similar to the first time she put it on, the feeling of complete transformation flooded over her again. It was amazing how her movements, her gestures, even her voice changed as soon as she looked so fully like a woman.


 

 

The first chore was to make her mistress breakfast in bed. Jenny busied herself in the kitchen making cereal, boiled eggs, toast and marmalade, fresh orange juice and a pot of steaming ground coffe. She knocked and entered Lisa’s bedroom, placing the tray by the side of her bed before opening the curtains to allow the early winter sunlight to stream in.


Lisa slowly opened her eyes and smiled at the thought of being served in such a way. The prospect of having a maid obviously pleased her greatly as her first words were “Thank you Jenny, you really are a little gem. I don’t want to let you become that awful John tomorrow – you’re much nicer like this.”

Realisation dawned on Jenny that this was her last day. She had been such a short time in her new role, but already she knew that this was the person she wanted to be.

“Thank you mistress. I like me like this as well.”


She curtsied and swished out of the room, but she could tell her mistress was thinking very deeply about something.

That evening, Jenny was busy sewing. She particularly enjoyed this chore as it required delicate movement and made her feel so feminine. Her mistress (which was really how Jenny thought of Lisa now) was sitting on the other side of the room, reading. She looked up from her magazine.


“Are you looking forward to going to work tomorrow, Jenny?” she asked.

It was hard to admit that her acceptance of her female role was so complete, but Jenny could not lie about something which was so important to her. “No mistress, I’m not. I know it’s wrong and I shouldn’t be saying this, but I realise now I don’t like John. Jenny is so much nicer, and so soft and gentle that I wish I could be like this for a lot longer. I don’t know if I can ever be John again.”


Lisa smiled. “I’m glad you said that. When I was at the office on Friday afternoon I told them that you had telephoned in to say you were very sick and could be off qork for quite some time, so you can be Jenny for a while longer yet. But I think you should earn your keep while you learn the finer arts of being a woman. Can you type?”

“Yes mistress, a little”

“Good. As I shall be running the office in John’s office I will need a temporary secretary. That would be a suitably feminine job for you to do.”

“But mistress, what if they recognise me?”

“You managed to fool Elaine didn’t you? I’m sure that you’ll be such a good little secretary that no one would even begin to suspect your real identity.”


Jenny felt a rising panic but realised that her mistress’s mind was made up. She would be returning to her old place of work… but as Jenny the secretary rather than John the boss.

 


 

 

On Monday morning Jenny was awake before her alarm went off. She had found sleeping difficult that night. It wasn’t just the fear of being found out, or even the strange sensation of returning to work as a mere secretary when she had been so used to being John the boss.


Her restlessness stemmed from the fact that Jenny was taking over her personality so completely. The strange, girlish sensations when she thought of Steve, or wore her dresses and high heels, or performed some little domestic chore for her mistress felt perfectly natural. And yet Jenny knew that the more she yielded to them the more she would be trapped in her new role. The question was, did she want to be trapped forever?


Jenny rose with the question still dominating her thoughts. She put on her maid’s uniform, as she still had to perform her morning chores before getting ready for work. When she took breakfast to her mistress’s room she found Lisa already up, preparing a suitable ensemble for Jenny to wear on her first day in her new job.


As Lisa took her breakfast, Jenny undressed and exmined the new outfit with typically feminine curiosity. The light grey stockings seemed to soften the outline of her sjapely legs. The pastel blue A-line skirt was mid-calf in length and had a gorgeous little kick pleat to produce a pleasing swirl effect as she walked. The cream coloured silk blouse has delightful little puff shoulders and a rather low neckline. The matching pastel-blue bolero jacket had padded shoulders and mid length sleeves. The high-heeled blue sandals completed the picture of a young girl set for a day at the office.

When it was time to leave, Jenny had a recurrence of her earlier feelings of trepidation. This was the first time she had been outside to mingle in the real world dressed as a woman. The first thing that hit her was the cold feeling of the early morning breeze as it played around her legs. It gave her a strange tingle as she realised how vulnerable it made her feel.


The drive to work seemed to take forever. Jenny spent the whole journey worrying about how the girls in the department would react and whether she would be found out – the consequences of which would be that John could never work there again… in fact, it could be the end of him altogether. But then, would that be such a disaster?

To make herself more convincing, Jenny fussed endlessly with her clothes and make-up while they were stuck in traffic. She smoothed down her skirt to get the most pleasing effect, applied and re-applied more lipstick, teasing her hair into more flowing, feminine waves.


Lisa watched from the corner of her eye, but gave little encouragement apart from saying “Don’t worry, Jenny, you look lovely. I’m sure the girls will treat you just like one of them.” Jenny tried to look as confident as she could, then went back to toying with her hairstyle.


When they arrived at work, Lisa ushered Jenny into her office and asked her to wait while she explained to the rest of the department what was going on. Jenny sat demurely, trying to listen to the voices in the outer office but she could not make the words out clearly. Lisa came in with a wry smile on her face and led Jenny out.

“Right girls, gather round. I want you to meet Jenny, who will be acting as the department’s secretary for a while. Any little jobs that you want doing, just ask and I’m sure she’ll be only too willing to oblige… she’s a real sweetie. Oh, and as I’ve just told you, Jenny used to be known to you as John, our boss.”

 


 

 

Jenny felt as though her legs had been kicked from under her! After all the promises Lisa had revealed her true identity… what would happen now? Jenny looked around at the other girls and saw that they were eager to take their chance of revenge for their previous mistreatment at the hands of John.


Elaine was the first to speak.

“Well, Jenny, this is a real turn-up isn’t it? You had me completely fooled when I called round on Friday. You should have been born a girl – it suits you.”

The other girls giggled, but she carried on. “Don’t think we don’t know how badly John used to treat us and look down on us. This is our chance to apply some of the same treatment. We’ve all promised not to reveal your little secret to senior management… just so long as you’re a good little girl and do as you’re told.”

Jenny winced inwardly, but she managed to smile and say in her most feminine voice, “I will be good, and I’ll try and do everything you ask of me. I’m sorry for the way I treated you all before, but I promise I’ll make it up to you.”

Some of the girls looked a little unconvinced, but before anybody could say any more, Lisa stepped in.

“OK girls, we have plenty of work to do. Now come along, Jenny darling, I want you to take a letter.”


She gave Jenny a little pat on the buttocks as she minced past and the other girls laughed. Jenny was red faced with embarrassment but followed Lisa – now her boss as well as her mistress – into her office.

The rest of the day went by in a mad whirl. The other girls seemed to make up as many jobs as possible for Jenny to do, but by the end of the day she seemed to have won some of their confidence with her quiet acquiescence in her new role in the department.


She was sent off mid-morning with Debbie to make drinks for the rest of the girls and found herself giggling about boys and chatting earnestly about clothes with a girl who she had only days before been trying to seduce. At one point, Debbie clasped her hand and said “I don’t care what you’ve been or done before. I like you as your are, Jenny, we could be good friends.”


Tears welled in Jenny’s eyes. She realised that she loved being a girl and being allowed to be close to other girls. Jenny wanted to think romantic thoughts about Steve and discuss the latest fashions with other girls.

Perhaps, if she was a good maid for Lisa, and a good secretary for the department, John would be allowed to fade away completely and Jenny could enjoy the girlish fantasies and feminine lifestyle that had now taken over completely. Her thoughts were interrupted by the familiar sound of her mistress.

“Pop in here a minute, Jenny darling. I want you to take some dictation.”


Jenny swished into her mistress’s office and gracefully sat down, resting one silk-clad leg over the other and placing her notebook demurely on her lap. Yes, Jenny would be around for quite some time, of that she was certain…

The End

 

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