Jeremy Smith sat nervously in passenger seat of the Porsche. He felt in a kind of daze, unable to fully take in what was happening to him. He glanced almost unbelieving at his black nylon-clad legs emerging from the froth of petticoats that set off the black satin skirt and frilly white pinafore of the maid's uniform that he was, incredibly, wearing as the Porsche glided into the town centre. "Feeling ready for your public debut, Jemima," said the voice of the attractive older woman steering the car smoothly through the traffic, "your public awaits." She laughed, smiling mockingly at the young man. Jeremy gave a start as the full horror of what was about to happen hit home, "I really don't think this is a good idea...." he started to say, but was cut short. "Oh no, you're not backing out now, we've come this far, and you know you want to do it really - its much too late to have second thoughts now, time for Jemima to meet the world!" With that she turned the car into the car park adjoining a small pedestrianized shopping square, "Right here we are," she said turning to him with a smile, "you know what you've got to do, you'd better get on with it." Jeremy took a deep sigh, he knew only too well once his mistress was in this mood that there was no escape. How on earth had he got into this predicament? -------------------------------------
Jeremy had first met Christine Roper at his mother's house about a year earlier. Jeremy was a reasonably successful young solicitor's clerk and lived in a flat in the next town, having moved out of his mother's home once qualified. His mother had asked him to visit as she was having a meeting with her financial adviser and felt she needed his support. Jeremy remembered being surprised that the adviser was a very smart and attractive woman in her forties, who immediately impressed him with her authoratitive, business-like manner. He found his gaze often straying to the hem of the skirt of her superbly fitting business suit as black nylon clad legs disappeared towards..... he realised that she was watching him with a smile playing at the corners of her mouth and felt himself blush as she seemed to read his thoughts. Her presentation was superb and her advice appeared very sound, soon, with his approval, his mother was agreeing to the investments she was proposing and, all too soon for him, he was showing Ms Roper out of the house. He knew he must see this woman again. "Mmm, I'm wondering whether perhaps I might have a look at some investments, perhaps you could also advise me?" Christine Roper looked at him with that faint smile playing at her mouth again, "Yes," she said, looking at her watch and then back at him, "I've actually got half an hour now, let's meet in the wine bar round the corner and have a chat, that'll give me an idea of whether you are a suitable candidate for the sort of things I may have in mind for you." She smiled that enigmatic smile again and it never occurred to Jeremy for a moment to turn down her strangely worded invitation. Over a glass of wine he found himself being drawn irresistibly to this formidable woman. The fact that she was about 20 years older than him seemed not to matter in the least - he couldn't remember ever being so attracted to a woman. The next meeting, for her to present her ideas to him would be at his flat and that was when, after him agreeing to her investment plan, she bedded him - and it really was her bedding him. Soon he was visiting her at her large house in a very expensive village on the edge of the town, and found himself, always at her instigation, enjoying the best sex he had ever experienced. He knew that he was completely in her power already, but didn't care at all. He found himself telling her his innermost thoughts and one day, as she aroused him yet again, this time slowly stroking his rampant member with her recently removed silk knickers, she noted the effect of the lingerie on him and at her prompting he admitted that he fantasised about being forced to wear women's clothes. She seemed to find this fascinating and questioned him remorselessly, refusing to let him enter her until he had "told her everything." And he even, as he could bear the suspense no longer, admitted that he had a few items of clothing at his flat that he sometimes wore to indulge his fantasy. After being rewarded with ecstatic love making he couldn't believe that he had divulged his greatest secret but, to his astonishment, Christine seemed not to be deterred at all by what he regarded as his shameful admission, but rather, wanted to know more and was fascinated when he reluctantly admitted that he sometimes wore a dress and a pinny to clean his flat. Without further ado she insisted that on his next visit he brought his "housemaid" outfit with him and laughingly told him that if wanted to clean a house that was one fantasy she was very happy to indulge! He started to argue, saying that he didn't really want her to see him in a dress, but she would have none of it, saying that was a sight that she couldn't wait to see, and then, teasingly, that she always paid her cleaners very well! So a few days later he turned up with his "housemaid uniform" in a case and found himself brusquely ordered to get himself dressed as there was a long list of jobs that required doing. With some embarrassment he went to the bedroom and slowly put on the knickers, bra, petticoat, knee length pink shirtwaister dress and white cotton apron with a rose pattern that he had gradually assembled from various charity shops. Putting on the low-heeled black shoes that completed the outfit he checked himself in the mirror and, taking a deep breath, walked downstairs to present himself, en femme, to someone for the first time. He opened the door to the lounge and entered. Christine stood and smiled at him. She stroked her chin and looked thoughtful. She spoke in her most authorative tone, "Mmm, not bad at all, but if you're going to be my housemaid I will be insisting that we make some improvements in time, we'll need to get you a wig and shave those legs but for now you'll do well enough, let's get you to work." She ran through a list of jobs and, first insisted that he allow her to tie a pretty pink scarf, turban style on his head "to complete the housemaid look." He found her a demanding mistress and worked hard as the day progressed with Christine on several occasions playfully patting his bottom and even letting her hand stray up his skirt. He couldn't believe this - his greatest fantasy actually becoming reality! She decided that a housemaid needed a more feminine name than Jeremy, so "Jemima" was born that day. Eventually his mistress decided he had earned his reward and what reward it was. Laying him on the bed and lifting his skirt and pinny she rode him to an incredible climax, then insisted on several more until they were both exhausted. As the weeks went by he became more and more in thrall to her. His housemaid duty became a weekly, then twice-weekly event and, as promised, she worked on improving his appearance. She showed him how to shave his legs and insisted that this was done on a weekly basis, even giving him a lady shaver as a beautifully gift wrapped present! She showed him how to apply make-up and then provided a wig. His figure was improved by a very restrictive corselette, and higher heeled shoes and changes of underwear were added. At each visit he underwent a short training session, in walking correctly in heels, sitting nicely in a ladylike manner or curtseying in suitably submissive style. One evening, as he presented himself for inspection, Christine surprised him further. "Well, Jemima, you are coming along nicely and so I have an opportunity for you. My cleaner is leaving and so I am going to offer you the job." She looked sternly at him. "You understand that this will mean a firm commitment, two evenings per week, without fail, and every weekend of course. You will find that I am a demanding employer but I think you'd rather like that wouldn't you?" Jeremy soon agreed with Christine's proposal, his manhood already aroused at the very thought of this delightful new humiliation! Soon two new dresses were given him, more like overalls really, one black and one dark red, each with a pinny and matching cap to complete the housemaid look It was obvious that Ms Roper ran a very successful business and had acquired considerable wealth, which, she joked, she was happy to spend on ensuring her staff were presentable! On arrival in an evening he now had to spend some time preparing himself for inspection by his ever more demanding mistress, who seemed to take great delight in making him correct some real or imagined fault in his appearance. Then, on his birthday came the real surprise - she presented him with a beautifully made French Maid's costume, complete with voluminous frilled petticoats, an ultra frilly white pinny and matching hat. In short, his perfect fantasy costume. He could scarcely believe it as this sensual mature woman zipped him into this ultra feminine outfit and sweetly informed him that now he finally looked like a real ladies maid and that he would wear this outfit to serve tea at the end of his housemaid duties, adding archly that she would now be proud to show her maid off to anyone that happened to call in for tea. She obviously noticed the terror in his eyes at the thought of this public humiliation and teasing him about being seen in female clothing became a feature of her conversation. She frequently made him take rubbish out into the garden or clean the inside of the windows, teasing him about being seen by passers-by and smiling thoughtfully as she observed his terrified efforts to avoid any public sighting. One day as "reward time" was under way she teasingly said that she was sure he must have fantasised about being seen in public whilst dressed and, eventually, he reluctantly admitted that this was the case, he had indeed fantasised about being forced into a public place whilst feminised, quickly adding that it was of course just a fantasy and he didn't really want to be so exposed "Oh I'm sure you'd love it, and you know I always make your dreams come true!," Before he had time to take this in he was in the throes of ecstacy as she mounted him and he found himself agreeing that a public outing was just what he needed! ------------------------------------------------ And so, a week or two later, he found himself sat in the car park of a shopping centre in the Porsche. As he had finished his housemaid duties that afternoon he had been ordered to take special care in dressing in his maid's uniform as there was going to be a "special occasion." Once dressed he presented himself for inspection and was stunned as Christine pronounced herself satisfied and produced a three quarter length pink raincoat that she asked him to slip on. "Yes, that's fine, it's a little chilly out so I don't want you getting cold, here, take this," she said firmly, slipping a little black shoulder bag onto his shoulder, "No lady ever goes out without a few essentials." Jeremy was stunned. "But I can't go out like this," he protested, "at least let me wear something less noticeable, one of my work dresses or something." "Of course you can and you're going to, wearing exactly what I tell you," snapped Christine, "you know you want to really, you've told me its been your fantasy. It'll be no fun at all if people don't realise what's going on and you will have no chance of escaping notice dressed like this! This is how its going to work. I'm taking you to The Mill shopping centre, you are going to walk around the perimeter, all the way, and you will talk to at least two people, ask them if there's a bank machine or something, and then return to the car. If I'm happy that you've done it properly I'll let you back in the car and we'll have the best night you've ever had. Is that clear?" Jeremy nodded dumbly and was still in shock as he found himself being led by the arm out of the door of the house and bundled into the Porsche! As they drove towards the shopping centre he had thought of how he had always been incredibly excited by the thought of being forced to appear in public in female attire, but now, as the time approached, excitement was replaced by dread of what was about to happen! As all this was going through his mind, Christine had impatiently got out of the car and walked round to open the passenger door. She bent over and took his hand. "Come on Jemima, this is the last step on the road to making your fantasy into reality. If you don't do this, my plan for you has failed and you'll never see me again. Do this properly and tomorrow you can resign from you job and come and live with me permanently as my housemaid and lover." She pulled his hand. "I don't think there's any choice, do you?" He stepped from the car, so nervous his legs almost buckled. Christine fussily straightened his pinny and cap and gave him a gentle push on to the pavement. It was early evening and most of the shops were closed so fortunately there were not too many people about - but more than enough for Jeremy! He walked gingerly forward feeling so conscious of the wind tugging at his petticoats and cooling the tops of his legs between his stocking tops and knickers. He tried to pull the coat about him but knew that it didn't hide his pinny and rustling petticoats. His mouth felt dry, he still couldn't believe this was really happening to him, walking about in a public place in a ridiculously feminine outfit. Suddenly a mobile phone rang, it took a few rings before he realised it was in his handbag. Hurriedly he opened the bag and answered the phone. Christine's voice was cool. "Good so far, now go up to those two women to your right, they seem very interested in you, and tell them your mistress wants to find a bank machine. Leave the phone on so I can hear that you do it properly." He looked around and for the first time noticed two women sitting on one of the seats, they did indeed seem to be looking at him. Again he thought his legs would buckle as he walked towards them. Clearing his throat he mumbled, "Excuse me is there a bank machine nearby." The women were staring at him in disbelief. "I'm sorry, what did you say?" said one, barely containing her laughter. He tried to clear his throat again, his mouth was so dry he could barely speak. Before he could say anything the other woman guffawed, "Why are you dressed like that, is this some sort of bet?" He realised he would be in trouble with Christine if he didn't get this right. "No, madam, my mistress likes me to dress like this and she has asked me to find a bank machine." He could feel himself blushing scarlet as the two women burst out laughing. "Well, I must say you look very pretty, your mistress must be proud of you." The other one interrupted, "I think I must look out for a maid like you myself - there's a bank machine over there," she said pointing to shop a little further along. With the women's laughter in his ears he took a few steps in the direction they had indicated. Suddenly he was aware of Christine's voice from the mobile phone, he quickly raised it to his ear. "Very good Jemima, are you enjoying this?" she asked. "No, mistress, please can I come back to the car now." There was a thoughtful silence. "Yes, but first you must apologise to those ladies for not thanking them properly for their help, with a curtsey of course!" "But mistress....." he started. "Just do it - or I will drive off now." Falteringly he turned back to the two, still highly amused, women. Wishing the ground would open up he stood before them. "I'm very sorry ladies, my mistress says I must thank you properly for your assistance." Lowering his eyes he curtsied deeply as they absolutely dissolved in hilarity. The voice from the phone started again "That's better Jemima, you may return to the car - but walk nicely, don't hurry! Accompanied by wolf whistles and catcalls from the two ladies, which drew him to the attention of several other passers by who watched in amusement he walked as delicately as he had been trained back to the Porsche, where he opened the door and slumped, drained, into the passenger seat. Christine leant across and kissed him firmly, at the same time slipping her hand up under his petticoats and stroking him. "Hmm, yes, I thought you'd find that exciting, wait till I get you home my girl. I'm going to give you the time of your life, and tomorrow we can start making plans for your new life. I think it's going to be Goodbye Jeremy, hello Jemima, I'm sure that's what you really want isn't it? I think its going to be very exciting don't you?" "Mmm yeeeees Mistress," gasped Jemima as his first orgasm of the night went cascading into his pretty knickers!
YOU ARE READING
A Wish to be The Maid
FantasyA young man's fantasy is made real by an older woman - more real than he perhaps ever imagined. ***Credit to Lesley for the amazing story***