Take a Letter Jenny Part One



John leaned back in his chair and sighed wearily. It had been a long day at the office, even by normal standards, but it was almost over and he was so much looking forward to tonight. He put his hands behind his head and surveyed his ‘kingdom’.

He smiled at the thought, but in a way, his being manager of the Accounts Department was similar to the role of a benevolent despot. He had been promoted there at a young age, and had initially found it difficult to order people around, but over the months he’d grown to enjoy his position of superiority. It was quite pleasant to occasionally overreact to some small error, just to ensure people knew who was in charge.

Of course, the thing that made his role easier was the fact that he had a department full of women. Not that he had any choice in the matter – being surrounded by females all day was not something he particularly enjoyed. All that giggling and silly chatter, and oohing-and-aahing over the new dresses they’d just bought!

He looked at each of them through the glass walls of the office. He could see Jan, his secretary, who was leaving the next day as her baby was almost due.

“I must get a replacement sorted out,” thought John.

Then there was the clerical staff. Denise and Elaine had both been with the company for a couple of years. John laughed inwardly at the thought that neither of them knew he’d seduced and bedded the other. Promises of promotion had helped, of course, but they should learn not to be so naive.

His eyes rested on Debs, the new girl. Only 19, a figure like heaven and a face to match, with long blonde hair caressing her slight, girlish shoulders. He would have his way with her before the year was out.

“Can we go through the report on the new budgeting system, Mr Fielding?”

John’s thoughts were interrupted by the attractive, if rather formal redhead standing by his desk. Lisa was the Assistant Manager, and the reason he was so looking forward to tonight – after months of persuasion, using every trick and chat-up line he knew, she’d finally agreed to have dinner with him.

“Yes, yes, of course, Lisa. But please call me John – I can’t stand too much formality with someone so pretty.”

He thought he detected her wince slightly, but she smiled. “I’m so looking forward to this evening Mr Field… erm, John, but there’s been a slight change of plan. I thought we could have dinner at my place – I’d love to cook for you.”

John was amazed – this was better than he could have hoped for. Dinner at her place, a few quiet drinks, soft music, then… well, who knows?

John found her house with no trouble and stood poised before the door. He collected his thoughts before he rang the doorbell – he still hadn’t got over the surprise of her agreeing to go out with him. In fact, he’d almost given up trying. He’d assumed that she’d learned of his opposition to her appointment as Assistant Manager, arguing that a man should be doing such an important job and there were enough women in his department already.

However, senior management had been impressed enough to overrule John, which caused him some resentment. In the early days, he’d made life very difficult for her, often treating her like a dumb secretary in front of other staff and giving her menial tasks to do. When he realised she wouldn’t break, he decided that it would be easier to bed her.

He rang the doorbell.


The door opened and John almost took a step back. She looked stunning, more like a real woman than she could ever look in those business suits. Her red hair was swept up on top of her head, she wore discreet but effective make-up and her black, figure-hugging dress was delightful.

“Don’t stand there on the doorstep all night, John. Come on in.”

He entered the hallway and the door closed behind him…

The fog lifted, to be replaced by a throbbing headache which made John wish for unconsciousness again. Suddenly he was aware of a tugging at his wrist and, with his headache temporarily forgotten, he realised that his hands were tied to the edges of the brass bedhead. Not only that, but his feet were tied at the other end of the bed in a similar manner.

He raised his head, despite the dull ache in his brain, and also saw that he was completely naked. The panic of being caught in such a vulnerable position caused him to struggle against the rope, but all he succeeded in doing was to tighten the knots still further, so that the pain became almost unbearable. He lay back with a moan of frustration and tried to remember what had happened to lead him into such a bizarre situation.

He hadn’t had too much to drink – he’d deliberately stayed sober in order to increase his chances of seduction. He remembered the meal well enough – he’d been in top form, complimenting her on her looks and getting into an amiable debate about the superiority of men. He remembered the two of them retiring to the sofa for drinks, the first, fumbled forays into lovemaking, and then… blackness.

That was it! His drink had been drugged. He vaguely remembered her laughing softly as he struggled against sleep, and the whispered remark in his ear: “Now we’ll see who’s the superior sex…”

And so here he was – defenceless. He’d made it to her bedroom all right, but not in the way he’d planned. He heard footsteps and
looked up. She entered the room wearing a flowing pink satin dressing gown which she immediately allowed to drop to the floor, revealing her beautifully rounded, naked body.

John felt a wave of relief – this was merely some strange sex game after all. Then the feeling vanished, to be replaced by a shiver of fear, as a cruel smile of victory played around her lips. Suddenly John understood – this was for real!

A surge of renewed confidence came over him as, with her back to him, Lisa rummaged through her wardrobe.

“Get these bloody ropes off me right now! There’ll be hell to pay at the office if you don’t stop being so damned stupid. I’ll… AAAARGHHH!”

He screamed as the stick came down sharply across his naked thighs. Tears welled in his eyes but she continued to ignore him. He was about to protest again, but the stinging in his thighs convinced him to keep quiet.

As Lisa continued to get dressed, he realised that she was preparing for work. He looked through the crack in the curtains and he became aware that it was morning… surely she’d have to let him free to go to work?

“Are you going to untie me now? I can’t be late for work.” He was aware that a note of submission was beginning to enter his voice.

“Don’t you worry your pretty little head about work” she said, “I’ll pretend that you phoned me to say that you’re too sick to come in today. That will leave you with plenty of time to think about your future.”

She sat on the edge of the bed and waved a handful of Polaroids in front of him. “These should convince you that, unless you do what I say, I can destroy your reputation at work. Either you obey my orders or these get circulated to our senior management.”

She showed him a series of photographs and he blanched. While he had been unconscious, she had dressed him completely in ‘little girl’ clothes. He stared in fascination at his shaved body dressed in the bonnet, pink blousette, short flared skirt that exposed the frilly panties underneath, frilled white socks, and to complete the humiliation, a large pink dummy in his mouth. Worse still, the photographs had been shot in such a way as to make him look like he was totally awake and enjoying himself!


“But why are you doing this?” he pleaded.

“Simple. You’ve made my life hell since I joined the department, and your pathetic attempts to seduce me made me hate you even more. Now’s my chance for revenge. All I have to do is show these photographs at the office and you’ll never be able to work there again.”

John panicked. “No, please don’t show these photographs to anybody!!! I’ll do anything, honest, I will!”

She seemed to reconsider. “Anything, you say? Well I won’t show them just yet. I’m going to leave you here like this and I’ll come home at lunchtime. Meanwhile, you’ll have plenty of time to think just what you’re prepared to do to stop me from ruining your career. The only thing that will satisfy me is if you make up for all the humiliation and frustration you’ve put me through these last few months. And there’s only one way you can do that – you can be my maid for the weekend.”

With that she got up and left, before John had had time to realise what she was asking him to do.

John spent the rest of the morning thinking about what Lisa had said. Part of him refused to accept that any woman could possibly want a man to act as her maid, but the care and attention to which she had gone in order to trap him like this, plus the obvious hatred she’d shown towards him had been enough to convince him that it was all for real. Then, too, there was the painful reminder of the stick cutting down across his legs. John decided to go along with the whole thing, at least until he could somehow get those photographs.

By the time Lisa returned from work, the agony of the ropes cutting into him made John desperate for release. He looked at her with pleading eyes as she walked into the bedroom, but she seemed to discount his presence completely. Again she sorted through her wardrobe, but this time John knew she was selecting the garments for him. He didn’t dare to look. Finally, she spoke.

“I’m going to untie you now, but you’d better behave yourself or else you’ll feel the full weight of my stick on your pretty behind. When you’ve been let free, I want you to put these clothes on one by one – and VERY SLOWLY. I want to admire the effect as you become a new person. I also think we ought to give you a new name for your role – what do you think?”

John didn’t answer, until the sting of a hard slap across his face made him mumble “Yes, yes, a new name. Whatever you say”

SLAP!! “Whatever you say, MISTRESS!”

“I’m sorry – please don’t hit me – whatever you say… mistress.” John was aware of a grovelling tone creeping into his voice.

“Good. Well, it has to be something suitably feminine and submissive, to remind you of your new role in life. I think we’ll call you Jenny. Do you like that… Jenny?” Her tone was mocking.

“Yes, I like my name a lot, mistress.”

She seemed appeased and began to untie John’s hands. Despite her previous cruelty to him, John couldn’t help but get excited when she leaned over him and her warm breath caressed his face. She noticed his sudden erection and slapped him hard again.

“I don’t want to ever see that again! You’re my maid now, and I’m beyond your wildest dreams.”

John cried inwardly, but allowed her to untie him without saying anything. She stood before him.

“Before you get dressed, I want you to kneel before me and beg me to let you put on your pretty new clothes. DO IT!”

John knelt before her, with the first signs of tears welling in his eyes. He’d never been so humiliated before, but he knew it would be impossible to resist her. “Please mistress, please let me wear my pretty new clothes. I want to wear my dress and high heels and stockings and apron. Please mistress… I just want to serve you and be your maid.”


She seemed pleased and allowed him to stand. The humiliation of having his naked body paraded before her was overwhelming, especially as she watched him with a cool, appraising look. She handed him a pair of black, delicately laced panties with a tiny red rosebud motif. He shivered slightly as he lifted his legs into them and pulled them on.

He suddenly felt very embarrassed, but she handed him a jet black corset and indicated that he put it on. He kneaded it over his rather slim body and breathed in as it settled into place. Suddenly, she grabbed the laces at the back and pulled hard, until John felt all his remaining breath escaping from his lungs. He gave out a sudden little scream. She fastened the corset and he realised that his breasts filled the cup and completed the girlish outline of his body. He also felt more trapped than ever, as if the corset was locked around his body.

Her eyes gleamed as she handed him the sheer, black silk stockings. They felt so soft and delicate that John was almost afraid to feel them in case he laddered them – and incurred the displeasure of his mistress again. He put them on very gently, which heightened the sensation as they glided over his shaved legs. He knew something was happening which could never be revoked, and the feeling of helplessness and vulnerability was growing with every item of clothing she forced him to wear.

Next came the shoes. They were shiny black court shoes with a stiletto heel and a pretty little bow at the back. He forced them onto his feet and silently cried as he stood up and the pain became intense.

“Now, walk over to the mirror, Jenny,” she mocked. He staggered over to the full-length mirror and immediately understood why she had chosen this particular punishment for him – he looked so feminine, with his calves stretched into shape by the high heels to give the impression of a leggy girl’s body. This impression was helped by the slimming effect of the corset, which not only pulled in his waist but also gave his hips and bust a much fuller, feminine appearance. John began to almost enjoy the transformation!

“Now then, Jenny, I think you should wear this.”

He picked up the elaborately-frilled and laced petticoat and, raising his arms in the air, let it rustle down his body. He watched, fascinated, as it settled into place around his waist, reaching just above his knees. He played with the delicately trimmed edges and wanted to cry. This wasn’t right… and yet it felt right to him.

The jet-black cire dress cam next. It hugged his body as far down as the waist and then flared out with the petticoat. He teased it into shape to produce the best effect, and was suddenly conscious of her staring intently at his every move.

“Enjoying yourself… Jenny?”

He realised then that his humiliation was complete – he was standing before her with a man’s features and a girl’s body. He wanted to hide, to avoid her mocking glance. He knew how ridiculous he looked.

“W-w-would you make me up, please mistress?” he pleaded. He knew it would be the only way to look even vaguely normal, and yet he understood that if this was to go any further, he would rather be mistaken for a girl than be seen to be a transvested man. All the same, he hated to ask her to complete his humiliation – it seemed like a final admission of defeat.


She led him to her dressing table and gently sat him down. She applied the foundation cream, and he just sat back passively. He closed his eyes as she applied the eye make-up, face powder and blusher, and finally the flaming red lipstick. His eyes wouldn’t leave his reflection in the mirror when he finally opened them – he was completely transfixed.

“Now then, I have a wig for you to wear, but first you must prove to me that you deserve it. Practice walking and talking in the proper manner, and curtsying, and if you please me I might decide to let you wear it.”

She walked out of the room, locking the door behind her. John immediately got to work, walking in the most feminine way he knew. He was helped by the heels and the shape of the corset, and he was aware that his hips were swinging and his stocking-clad legs were constantly brushing each other.

He practised curtsying, daintily lifting the hem of his dress and, placing one foot before the other, slowly bobbing up and down. He was too busy worrying about his mistresses fury to think about how he might look.

When she re-entered the room he felt almost like a woman and was eager to show her the progress he had made. She laughed at his attempts to walk without tottering on his high heels, but seemed to enjoy his curtsy, which seemed so subservient when she was watching him. He talked in high-pitched, soft voice and she congratulated him on his natural ability to behave as a girl.

To show her satisfaction, she placed her hand in the carrier bag which was by the bed, and with a flourish produced a beautiful mid-length blonde wig. It had been styled to produce a very feminine look, with flowing, delicate curls flicking out.

John fingered the silky tresses with eager anticipation. He placed the wig on his head and adjusted it until it felt tight agains his scalp. He wasn’t prepared for the little gasp of surprise which Lisa inadvertantly gave out and rushed to the mirror to see the effect for himself.

When he looked at his reflection, his legs almost gave way from underneath him. Staring back at him was a young, pretty girl with
a shy smile and a soft, feminine face. It was amazing how the wig produced the final transformation. Suddenly his stance, his gestures, even the sound of his voice felt so wonderfully, naturally womanlike.

“Right, Jenny my darling, it’s time for you to go to work. You can start by cleaning all the floors downstairs, and I’ll inspect your work when I come home this evening. It had better be spotless – or else!”

John spent the rest of the day working as he had never worked before. The endless scrubbing and dusting and cleaning wore him out, and yet he had to admit to a certain satisfaction with his menial tasks. He bagan to hum to himself and swish his skirts around his legs. He looked in the mirror at every opportunity to admire his prettily made-up face, and realised that his new role was becoming very natural to him.

Suddenly the doorbell rang and John’s heart skipped a beat. He wanted to ignore it but the glass panelled front gave away the fact that he was in the house. He walked as daintily as possible to the door, opened it and saw Elaine from the office!

In his most feminine voice he said “Hello, can I help you?”

“Oh, yes. You must be Jenny, the maid. Lisa told me I’d find you in. She asked me to come round to pick up a pair of shoes for her. She wants to wear them this evening.”

John felt a wave of relief – she hadn’t recognised him. “Right away, miss. I’ll show you to the mistress’s bedroom” he said in his high, girlish voice.


Elaine followed him up the stairs and John thought it was ironic that the girl he had bedded only a few months ago was now looking at him as a dumb servant girl. He wanted to shout at her, to tell her who he was, but instead he only blushed and helped her look for her shoes.

When he had shown Elaine out, John carried on dusting and cleaning. He was aware that it was getting late and realised that Lisa must have gone to Jan’s leaving party. He didn’t dare stop working in case she punished him again, so he continued to vacuum and clean until she returned late in the evening.

She seemed a little tipsy. Almost without thinking, John curtsied and helped her take off her coat. She seemed pleased by this little impromptu display of acceptance of his new role, and asked for a demonstration of his new-found femininity.

John minced before her, careful to walk gracefully and with a feminine sway. He felt humiliated, but at the same time he was anxious to please her, and not solely because of the threat of punishment. He curtsied again, and then sat opposite her, with his hands folded demurely on his lap. She looked around to assess the results of his housework and then addressed him.

“Well, Jenny…” She paused to let the name sink in. “I’m very pleased with your progress. You make a very pretty little maid, and your work around the house has been excellent. I’m going to prove my confidence in you… I’m going to let you serve at a dinner party I’m hosting tomorrow evening.”

John felt as if he’d been kicked in the stomach. Serve at a dinner party? In front of lots of people? He would not do it, not in a million years!

She must have read his thoughts, because she proceeded to remind him that the photographs were waiting at work, and she had disposed of all his male clothes so that there was no way he could leave the house. The hopelessness of his situation began to dawn on him, and the next thing John knew he was sobbing uncontrollably.

Lisa put her arm around his heaving shoulders. “There, there, don’t cry Jenny darling. You’ll be magnificent. And by Sunday, it’ll all be over and life can get back to normal.”

But John continued to sob – he knew life would never be normal again.

End of Part One



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