Sissy Prudence Part 1 free porn video

Sissy Prudence (Part 1) (by Sissy Caroline - 14 December 2006) He paused at the top of the stairs waiting for his heart to slow down a little. He had never been confronted by these circumstances before and for a moment he thought that he would break into tears, something he did from time to time when things upset him. At 13 years of age you would have thought he should be well past that stage, but he wasn't. In fact as time went on it seemed he was becoming more emotional. He had one final look in the hall mirror to check everything was in place, before he put his left hand on the stair rail and slowly started to walk down to the main room of the house. Some time before, his mother had greeted one of her best friends, Mrs. Smithton, and ushered her into the lounge, asking her to take a seat and, by the way, would she like a drink of tea. Once the tea was poured they sat and talked for a while about things in general before Mrs. Smithton couldn't hold in her curiosity any longer. "So tell me Jennifer, how did all this start. I can't believe that your little Peter really does like wearing girly clothes." "Well, to tell you the honest truth Anne, neither could I at first, but it is true and as you will see he does it rather nicely. I suppose the start was when he was about 8 years of age. I came home one day to find him asleep on his bed under a soft plastic sheet that I had stored in his wardrobe since he was out of nappies. He looked so peaceful and relaxed I didn't dare wake him, but it made me start to think about what was in his mind about such things. So, I bought a new pair of plastic panties to fit him and left them in the wardrobe as well. It took some time, but I finally knew that he was putting them on at night after I had put him to bed." "Didn't he know that you had left them there for him, and that it was a sort of a trap?" "Well, he may have, but whatever he thought it did not stop him from trying them on. Then one night I decided to go into his room after he was in bed and see if he was alright. Of course, I knew he was, it was just an excuse, and as soon as I sat next to him on the bed and touched the blanket I knew he had them on. So I asked him if he really liked wearing plastic panties to bed, because he didn't really need to if he didn't want to. Of course he was embarrassed but it was clear that it gave him a lot of comfort and it was then I got the plastic sheet, pulled back his covers and placed it over him before putting the covers back on. I have to tell you Anne, his reaction was one of sheer pleasure. He sort of looked at me with dreamy eyes and said thank you and almost immediately went off to sleep. The next step was simple. I suggested that if he really liked wearing plastic panties then he should really be wearing nappies to bed as well, and that Mummy would be more then happy to put him in nappies every night and tuck him into bed all snug and warm. And the fact is that I have done that for him most nights since, even encouraging him to wet his nappies at night rather than have to get out in the cold to go to the toilet. Can I explain why he is like this? No, I can't, but I know he loves being treated that way and I must admit that I love it too. It has brought us very close together. From there it seemed almost natural that he would like to wear some girl's clothes and so I gradually gave him the opportunity by leaving things out for him to wear if he wished to do so. And so here we are today where he really is the sweetest boy you could ever imagine, although I do worry about what is ahead for him. He has limited numbers of friends, although he does very well at school, because I think he is always thinking about coming home and dressing as he wants to dress rather than being in boy clothes." "Here he comes now Anne. Please, please don't say anything until he is down the stairs and made his greeting to you. I have had him working on this moment for a long time, because he knows that at some stage it is inevitable that others become aware of his activities as a sissy." Anne watched entranced as ?Peter' walked slowly down the stairs. His hair was still reasonably short but beautifully soft and shiny with a lovely wave through it that made it look very feminine despite its length. Perhaps it was the light blue satin bow pinned at the side that made it look so lovely. He had on a full length blue satin dress that billowed out around him in waves created by multiple layers of white lace petticoats that showed as he took each step. The dress had short puffy sleeves with white lace trim, and there was a white lace trim collar as well as a white satin band around his middle tied in his back into a huge bow with long trailing ribbons. Pearl earrings and a double strand of pearls in a choker around his slender neck were set off by makeup dominated by a luscious pink lipstick and eyes where the mascara, eye shadow and eyeliner made him look both feminine and very sexy at the same time. When he reached the bottom of the stairs he walked to the front of Mrs. Smithton, curtsied on his white 2" heels and then said in a low voice, "Hello Mrs. Smithton, my name is Prue." Anne was stunned by the vision before her. She stood up and took one of his hands, noticing his long pink nails, and put a hand on his waist before leaning forward to kiss him lightly on the cheek. "My dear you are so beautiful, and it is wonderful of your mother to let me meet you and see what a glorious creature you have become." Anne was intrigued because by touching him she became aware that he was very tightly corseted. She would have to learn more. "Run along now dear and get us both another cup of tea. You may have one as well if you wish." "Yes mother," and he walked from the room with Anne's eyes following him all the way with delight. "You have him in corsets dear", she asked somewhat surprised. "I would have thought that would not have been necessary." "Well, of course he doesn't wear them all the time, but he just loves girly underwear and the corset he has on today is his favourite. The only trouble with it is it takes me some time to lace him in, but he insisted because this is such a special occasion." Prue soon came back with the cups of tea on a tray and then served them to his mother and Mrs. Smithton, before standing still waiting for permission to sit and have his cup of tea as well. "Put your cushion at my feet darling and sit down and have your tea. Careful not to crush that pretty new dress, and make sure you fold your legs properly as I have taught you." The boy sat down as he was told and quietly drank his tea while listening to his mother and Mrs. Smithton discussed everything from the weather to what they had bought in the last week at the sales. "Mrs. Smithton is nice isn't she darling." Jennifer sat on the edge of the boy's bed as he prepared to go to sleep. She had already powdered him and put on his nappies and plastic panties and made sure he had cleaned off his makeup properly and used his moisturizer to keep his skin smooth and clear. "Yes Mummy, I like her. She seemed to understand and thought I looked nice, which was good of her." "I told you things would be fine darling. I think it is about time now that you have come out, so to speak, that we did a little more of that sort of thing so you can express your personality more openly. What do you think?" "Well. I suppose so. I did enjoy being with both of you today." A big kiss and cuddle before she left made Peter feel warm and cozy, and he really did sleep like a baby even though he had one of those delicious dreams where he came into his nappies. He just loved it when that happened. ________________________________________________________________________ Mrs. Smithton was due to come over again in a week's time and Jennifer pondered for a long time on what Peter should wear. She thought it should be something bold and a little outrageous because she thought Anne would cope with something a little bit off the wall, as she called it. Over the years it had just naturally occurred that she determined what Peter would wear at any time. He seemed to be happy with it that way, as it made his life simpler, and Jennifer was very happy with it because it gave her increasing control over her son's life. There was nothing planned about any of this, it just seemed to be natural for it to be that way. Just to be sure, she rang Anne to tell her what she was planning and was pleased to hear the excitement in her voice as she agreed and even suggested something she could bring to add to Peter's outfit. This time as Prue came down the stairs, Anne could barely contain herself. While the last entrance was so demure and full of frills and bows and petticoats, this one was totally erotic. Everything Prue was wearing was made of plastic. He had on a tight dark pink plastic g string under a pair of transparent pink panties, a clear plastic laced corset, a bra with the nipples of the breast inserts pushing against the top of a short dress made of the same material as his panties, and to top it all off 4" clear plastic heels. He had on a small plastic bonnet that framed his beautifully made up face and gorgeous dark pink lips. He was stunning, and his bare smooth legs almost glistened as he minced his way down the stairs to stand again in front of Mrs. Smithton and curtsey rather provocatively. "Well. What have we here? Is this the same boy I saw last time?" As she spoke she reached into her bag and withdrew a white plastic harness with gold buckles that she soon had fastened on him. "Do you think the straps and collar are tight enough Jennifer?" At a shake of the head from Jennifer she tightened them considerably and watched with fascination as the boy accepted the constraint without a murmur of protest, particularly as the collar was very wide and very firmly fastened around his neck and clipped and locked into place so he could not remove it even if he wished to do so. "Do you have a lead as well Anne? If not I can get something for you." ?Yes I do Jennifer. I found this lovely gold chain which will clip onto the collar of his harness. Here we go." And there he stood, shaking slightly with excitement wondering what would happen next. It was then that the phone rang, and the message was that Jennifer had to leave the house for a while to purchase some items for her work that were urgently required. "Why don't you take him for a walk in the garden Anne. I won't be long." Anne led the boy through the house and outside into what was a lovely green and very sheltered garden. With no words spoken they walked quietly around for a few minutes before Anne sat down on a bench, expecting Prue to sit down next to her. But he stood quite still, seemingly awaiting permission to do something. Anne asked what was wrong and he told her that when he was dressed as a girl he had to have permission to do most things and that he was always required to sit at the feet of his mother, not next to her. "Well. Sit at my feet then girl." To Anne, this was a revelation. Fancy having a boy who was so docile he would wait on you and look after your every wish as this one seemed to want to do. He was comfortable in her presence and in fact, seemed to enjoy her company. The possibilities were endless, as she lived alone and often wanted for both help around the house and for company. "Do you like to be called Prue or Prudence darling?" "Whatever you wish Mrs. Smithton. Mother often calls me Prudence when she is being strict, but if I am in her good books she will usually call me Prue." "Well I will do the same then. Perhaps your mother will let you come and stay with me sometime. Would you like to do that? You could make me cups of tea, clean up a little around the house, and perhaps you could even sleep over and I could put you to bed in the same way that your mother does." "Yes Mrs. Smithton." "Is that all you can say? You don't sound enthusiastic," and she touched his cheek lightly as she spoke this time and then played with the ribbons on his bonnet that fell down over his dress. To her great surprise he turned his head slowly and kissed her hand gently in a sign of submission and acceptance of her proposal. She was aroused by this and touched his pink lips with one finger while gently pulling him towards her with the lead. Almost without thinking the boy opened his mouth and kissed her finger, gently taking it inside him and then sucking it with obvious pleasure. Anne was aware that Jennifer had returned and was watching them, but the boy was not so he could not see the joy on his mother's face as she saw her son responding to another woman in this way. He was truly a sensitive boy with a lot of love to give if he was provided with the right environment, and she intended to provide more and more opportunities for him to grow as a sissy. Soon his mother came forward and sat on the bench next to Anne, and they sat there completely relaxed and comfortable while Prue sat at their feet and listened as his mother agreed that, "of course he can stay with you at times. I am sure he will enjoy it and it will broaden his experiences in life. We should do that very soon." That night as she put him in his nappies she was entranced by the way his penis came erect when she powdered him. "Do you play with yourself at night darling?" It sort of popped out of her mouth before she had thought about it, and she was angry with herself for asking such a leading question. Although he was surprised by his mother's question, he responded that he did sometimes play with himself, and he assumed that all boys his age did that >from time to time. "Have I ever given you permission to do that darling?" "No Mummy. I am sorry. I didn't think I needed permission." "Well dear, you do now. I think that if you are going to stay with Mrs. Smithton at all then you cannot play with yourself unless you have my permission. It would be unfair to her in the first instance if she is going to change your nappies. So. Is it agreed that from now on you will not play with yourself without my express permission?" And so, a new control came into the boy's life, and it was one that was to have a profound influence on his future because, although a promise is a promise, how can a boy of his age and urges live up to such a promise? The truth is that as hard as he was to try he could not. At night all rugged up in bed he loved to play with himself while lying on his stomach and feeling his plastic panties encasing his nappies before he spurted into them leaving himself panting and exhausted. ________________________________________________________________________ "Mrs. Smithton and I have discussed what sort of maid's dress you should wear Prudence, and this is what we have decided. I don't care if you don't like it. It is what you will wear and unless you apologize for your insolence I might be forced to do something that you will regret." He had never seen his mother like this. Certainly she always determined what he would wear, but until now it had always been something pretty or sexy. This maid's dress was neither of those things and he thought he would look silly in it, and that it would be really hard for him to work in. If he had to wear a maid's dress why not something short and frilly as he had so often seen in internet shops. He knew he was in trouble, something that happened very rarely, and so he did apologize while trying to explain to his mother why he had become upset. "Look I am sorry dear. It is just that Mrs. Smithton and I have agreed on this and I guess we thought that you would like it too. Let's try it on and see how you look before she arrives to take you home. If there is a major problem perhaps we can do something else, but Mrs. Smithton was so looking forward to you being her maid for the weekend." He was already tightly corseted and with a black bra, suspender belt and stockings he had already started to look the part. The dress to which he had objected was a long sleeved full length dress with a hobble skirt. A white pinafore fitted over the top and tied around his waist in a big bow. His shoes were black of course with 3" chunky heels, and his mother had also bought him a little black with white lace cap. Once it was on him he was forced to walk in tiny mincing steps and at first he was really unsettled by it all. His mother left him alone for a while as she packed his bags for the trip to Mrs. Smithton's place, and when she returned she could see that he seemed to have settled down and adjusted to the new attire. "Is it okay now darling? You must know that you look very sweet in it - it is so different from anything else that you have worn I know, but you do look lovely." "Do I really mother? It feels so strange to be dressed like this, and of course I have never really been a maid before so I am nervous about it all. I don't want to disappoint you but I am so nervous I feel like I want to cry." She took his hand, and walked with him to the mirror in the hallway. "Look at yourself. How could anyone who looked like that disappoint me. You have to be truly beautiful to look so good in an outfit that is as plain as this one." When Mrs. Smithton arrived she too commented on how good he looked and his nerves began to fade. Her car was out in the street and she made sure the coast was clear before taking the boy by the hand, settling him into the car. His mother put his bag of clothes in and half an hour later he was alone with Mrs. Smithton at her place. Despite the hobble skirt he soon learnt to get around reasonably well, and he did a number of cleaning chores before he was asked to make some afternoon tea and then sit at Mrs. Smithton's feet. "Do you like the harness I bought for you Prudence? I think you liked it when I put in on you, but perhaps you don't like being controlled by a woman in that way. Your mother thinks you loved our little walk in the garden, but is that true?" Very quietly he said that, "yes, it is true", but it was so quiet she had to ask him again. "Yes it is true Mrs. Smithton", he said this time in a much firmer voice. "Well, I am pleased. Perhaps I should get it now and put you in it again - would you like that?" This time he nodded his bowed head, and soon he felt himself collared, harnessed and leashed again. The truth is he loved being controlled this way, because it made him feel even more submissive than usual and that, in turn, made him feel closer than ever to the woman controlling him. The collar in particular made him feel so submissive it almost frightened him. "Turn around and put you hands behind your back." He turned while sitting on his cushion, and then just knew that she was going to somehow cuff his hands together. He could still resist but to his surprise she asked him if he would like to be cuffed. What would she say if he said ?no' he wondered, but he just nodded agreement and then felt the cold steel of a pair of handcuffs fastened upon him. "There. You look so pretty and demure and you have worked so hard for me I think that it is time that we relaxed outside." Again she led him outside and he walked behind her until she sat in a seat under a huge elm tree, spread a rug for him to sit on and then pulled his head so it was resting on her thigh. For an hour she did not speak, and of course he said nothing. She simply made sure that he was as comfortable as he could be given the way he was cuffed, and she gently stroked his hair and face, occasionally reaching down to kiss him on the neck and cheek. He loved the smell of her perfume and when he could he nuzzled her hands with his face and kissed her gently on the thigh through her dress. At long last she took him back inside, released him and told him to change into a simple cotton dress and come down for dinner. Almost no words were spoken. It was as though they communicated better without words. As she powdered him getting him ready for bed, she looked directly into his eyes and smiled and then kissed him full on the lips before pinning his nappy on and sliding those oh so soft plastic panties up his smooth legs. It was then she surprised him with another collar that was separate from the one attached to his harness. This one too was white but it was about 3" wide and made of a quite thick but pliable plastic. He felt her clip and then lock it into place while she very gently leant over him, her bosom close to his face as she locked the collar at the back of his neck. "There. That's much better. I thought you liked the collar on your harness so much that you should begin to wear a collar much more often." A final kiss, the covers on and it was lights out to another one of those wonderful dreams where he had no control at all. "He was wonderful, and I am sure now that you could increase your level of control and he will respond in a positive way. You saw him at your place when I had him harnessed. He becomes even more docile if that is possible, and you can feel the warmth radiating from him. By the way, his nappies were full of you know what in the morning, but when I questioned him he said it was a wet dream. I have no reason to doubt him this time, but you know what boys his age are like. You may need to do something more positive at some time if you really require him to ask permission before playing with himself. I can have a look for options if you like. Oh, and by the way, the collar looks so lovely upon him. I think you should make him wear it every night." "Thanks Anne. Yes, I will put him in the collar from now on, and it would be good if you could look at options to control him playing with himself.. I don't want to push it too far too fast, but since he has met you he seems to be more accepting of control and discipline. Perhaps if the suggestions come from you it would help. By the way, thanks for that beautiful little baby outfit you bought for him. I will use it on him this weekend - come over if you wish." ________________________________________________________________________ When Anne came over that weekend she found that Prue was already dressed in the baby clothes that she had bought for her, and was sitting quietly on her cushion next to his mother's chair. His legs were bare but his toenails had been painted a light pink, there was a little lace anklet clipped around each slender ankle, and there was just a hint of his plastic panties peeping >from under his short pink satin dress. Anne was delighted to see his harness was on the floor beside him waiting for her to put it on him. During the week she had also gone out and bought a satin bonnet to go with the outfit and, just in case Jennifer did not have one, a large dummy with a ribbon attached. "My but he looks so gorgeous Jennifer. Did he dress without any complaints given that he looks so babyish?" "Well, as it happens Anne, he did object a little. I have never made him dress this way before, but when I told him that you had bought him the outfit especially because of his good behaviour as your maid, he calmed down and agreed to put the outfit on. The truth is he loves it. He has been sitting there for nearly an hour now without any complaint and every now and then he runs his hands over the little skirt and lifts it up to touch his plastic panties. I suspect that inside those nappies we have a very excited little boy. Come on. Let's go in and I will get you to put him in his harness." Anne loved doing this to him. Without saying a word she was entranced as he raised his arms and leant forward so she could slip the harness on to him before buckling it in place firmly, locking the attached collar around his neck and attaching his leash. Then without a word passing between anyone in the room, she pinned the dummy she had bought for him to his chest and slipped the bonnet on him, tying the ribbons below his chin in huge bows. Jennifer looked on in delight. Anne was proving to be capable of reaching out to him in a way that she had not seen before, and between the two of them her little Prue was being led to explore wonderful new facets of her inner self. Jennifer picked up the lead and pulled her son even closer to him, She put the dummy in his mouth and told him to leave it in until given permission to remove it, and at the same time reached down to smooth out his skirt over his panties. Even the light touch of her hand in this area made the boy shiver and both Anne and Jennifer watched in silent fascination as he closed his eyes trying to fight off the urge to come into his nappies. Finally he settled down and it was then his mother spoke quietly to him. "You are a good girl for controlling yourself Prue. It must have been hard for you, but I know that you did it because you wanted to obey me didn't you?" "Yes mother." They kept him dressed in that way for the remainder of the day while they allowed him to relax with them in the house and for a time on a rug spread in the shade on the lawn in the back yard. After he was put to bed, Jennifer and Anne talked about how things were going and Anne raised her thoughts on controlling his capacity to play with himself whenever he wished. "I thought this would be easy Jennifer, but it isn't. There are a few devices out there that claim to work, but the one that seems to be the best is a full chastity belt which locks him away very securely. The trouble is that they need specialised fitting and they are also expensive, and perhaps you do not want to go that far at this stage." Jennifer thought about it for a while. It wasn't the cost that worried her. It was his reaction and the need to get someone to do a fitting. "I will tell him that is what I am going to do Anne. Assuming he is not totally negative perhaps you can arrange an appointment for us to visit the lady you have spoken to and get a fitting." Within a week an appointment for a fitting had been arranged in a month's time. ________________________________________________________________________ Peter hated going shopping with his mother. What boy didn't? But today, because Anne was going with her, Jennifer insisted that her son accompany them. He knew what it would be like. Hours of dawdling around looking at things but not buying them. Window shopping. Well. It didn't quite work out like that. Sure they did some window shopping, but as it turned out both his mother and Anne had decided to get themselves some new clothes and makeup. Peter went to wander off while they did so, but again his mother insisted that he go with them because, as she explained, it would be wonderful for him to see the range of clothes and accessories that were available to women or, as she said with a smile, little boys who liked to dress as girls. Peter blushed but had to admit finally he was interested and so he went with them into a huge department store where they stayed for a couple of hours. His mother wanted to buy a bra, panty and suspender belt set and eventually, after asking Peter's view she bought a lovely mauve set with lace trim that Peter thought would look very nice. Anne bought a short skirt before looking for some new high heels, again getting Peter's approval before settling on a strappy pair of 3" stilettos. "And what would you like us to buy for you darling?" said his mother when they were in the corsetry section. Peter blushed, although no one could have heard the question. "I don't want anything mother." "Don't be silly. There is very nice long line bra and long leg panty girdle set that would give you very nice control especially under that knee length floral dress Anne bought for you a few weeks ago. What do you think? I would love to buy it for you." And so the deal was done, with Peter accompanying them through the checkout as his new garments were purchased. In truth, he could hardly wait to get home and try them on. From that day he very often went shopping with his mother to buy makeup, clothes and accessories that he could wear when he was told to dress as a girl by his mother. Anne wore the stilettos the next time Prue was doing maid duties at her place. She found that he was fascinated by them - on the one hand they seemed so flimsy, but they gave a powerful image of strength and control to the woman wearing them. After his duties were finished he was allowed to sit next to her and she made him kiss her shoes and especially those slim powerful looking heels. He had no idea why they were going to drive almost two hours to meet a friend of Mrs. Smithton's, but one Saturday morning they headed off early. He was dressed as a boy as always when he was away from home or not at Mrs. Smithton's place. Although his mother had suggested once that they go for a walk while he was dressed, he didn't wish to do so, and his mother was wise enough not to push the issue. She knew the time would come. It was a Miss Hampson they were visiting said his mother, and Miss Hampson lived in a pretty small cottage on the edge of a tiny village. She was a little bit older than his mother and seemed very friendly. She greeted him with a big hug and looked him over carefully before settling them in for a cup of tea. "So, will we get on with the measurements Jennifer?" "I think we should. Please go with Miss Hampson Peter. She needs to take some measurements for some new items we are going to buy for you." A short time later, Peter came running out of the room. "What is she doing? She wants me to undress totally and measure my private bits. Mum. What is going on?" Jennifer took the distressed boy aside and spoke quietly to him. "You remember that you promised not to play with yourself without permission?" He nodded. "Well, I know that you have been disobeying me. I can see the evidence in your nappies that you put in for washing every morning. I am right aren't I? You do play with yourself without permission." Again the boy nodded before saying, but I just can't help it Mum. I try not too, but I can't help it." "I understand darling, so Miss Hampson is measuring you for the chastity belt that will help you, and me, control those things when I want them to be controlled. It is important that we get these urges of yours under control. I want you to be a good girl not a bad little boy." Two weeks later, Miss Hampson arrived with the belt and, after just a few adjustments, Prue was locked inside the belt feeling totally controlled and submissive. Miss Hampson was gentle and understanding, explaining that the cost included any necessary adjustments over the next few years. She had made a number of belts for other little ?girls' like Prue, and was very concerned to ensure that her customers were totally satisfied with the product. "Leave it on for short periods at first but you will find he will adjust to it readily provided you are careful with hygiene. I know of one mother who now keeps her son in his belt for two weeks at a time, and then allows him relief for a day before he is locked up again. She actually is looking to extend the period to a month in the near future. She is convinced it is good for him, and of course it has increased his dependence on her enormously, and he is very attentive to her needs and absolutely compliant and submissive. I would be surprised if you cannot achieve the same with Prue. I will also ask my other customers if they are happy for you to contact them if you wish further advice on how to manage this quite dramatic change in his life." Two weeks later there was an eruption in the household. Someone at school had accused Peter of being gay. He had no idea why this had happened, because the truth is he just loved girls. He was very shy, and perhaps that is what led to the accusation, but he really did like girls even though he was very awkward in their presence. It was not unusual for a young boy to be shy, but the accusation hurt him a great deal and when he got home he absolutely refused to have anything to do with dressing as a girl again. This went on for two weeks, until the Friday night when he arrived home >from school, and his mother had laid out his prettiest frilly little girl clothes on his bed. He refused to put them on, but he soon found that his mother was simply going to insist. "I have had enough of this nonsense of the last two weeks. I know and you know that you are not gay, but we both know how much you like being a sissy and you are going to dress as prettily as you can for me right now or I will give you an almighty spanking. Now get dressed and come down to the lounge. Anne is coming over and she expects to see you properly attired. When you go to bed tonight I am going to get Anne to put your belt on and you will not be released until I consider that you have got over this nonsense. Now hurry up and do as you are told, or else." She turned on her heel and left the room, leaving the boy in a quandary. He wanted to do as he was told, but could he do that given all that had happened in the last fortnight. Jennifer was anxious. She thought he would obey her, but she wasn't certain. Anne arrived in the middle of all this, and asked if she could help. Heading upstairs to his bedroom she marched in without knocking to find him sitting on the bed partially undressed and holding his panties. "Do what your mother says Prue. Do it now and do it quickly or I too will spank you. You have no choice in the matter. Be dressed and downstairs in 15 minutes." Without another word she left and went downstairs. "He was already starting to dress Jennifer. I am sure he will do as he is told." A short time later Prue came down the stairs looking as lovely as ever. However, she was not wearing what her mother had put out for her. Instead she was in the transparent pink plastic outfit that she had worn a few weeks ago - a tight dark pink plastic g string under a pair of transparent pink panties, a clear plastic laced corset, a bra with the nipples of the breast inserts pushing against the top of a short dress made of the same material as his panties, 4" clear plastic heels and a small plastic bonnet that framing his beautifully face with dark pink lips. As she reached her mother, she curtseyed and said "I am so sorry Mother that I have been naughty. I wanted to wear something really really special for you so I decided to wear my favourite outfit - I hope that you approve." He knelt in front of her with his head bowed hoping everything would be alright, as of course it was. His mother was delighted that he had dressed the way he had and she kissed him on the cheek before suggesting that perhaps he needed some help to tighten his corset which was difficult to do by oneself. She tightened it around him and smoothed down his skirt before asking Anne to collar and harness him firmly. "Now, while I get something ready for us to eat, why don't you take our sweetie for a walk in the garden again Anne. He loves being with you out there, and I think he needs to be rewarded for making the right decision, don't you." Anne led him outside and again she sat on the bench in the garden while he sat at her feet. She reached down inside his plastic panties and unclipped and removed the g string. "There. Does that feel better my darling?" He didn't know what to say but he became very hard and excited by this even though he knew that if he was to come he would be disobeying his mother. Anne watched him with strong feelings as she saw him struggle inside, and she was smart enough to allow him to settle without exciting him any more. But the g string stayed off and when she led him back inside he remained erect, pushing out the front of the plastic panties quite noticeably. Strangely, he thought, his mother accepted it all without comment as though it was the most natural thing in the world for him to be exposed in this way. He had to admit it was comfortable without the g string, and he loved the feel of the plastic moving against his erect penis. He was to find that he would be allowed to dress this way on special occasions when he was with his mother and Mrs. Smithton. That night, Mrs. Smithton locked him in the belt, put his nappies and plastic panties on over the top, and slipped on his white nightie before locking on the collar he now always wore at night. It was a restless night as he felt himself constrained by the tube of the belt every time he tried to become erect. "You will need to wear the long bra and panty girdle set under that floral dress darling. Have you got them on?" "Yes mother, but the girdle is very tight." "It will get more comfortable as you wear it dear. Get your handbag and let's go. Anne is waiting for us. Those new gloves go nicely with that outfit don't they." After picking Anne up at her house they drove north to see Miss Hampson, who they had arranged to stay with for a short while because it was the start of the long school summer holidays. When they arrived Miss Hampson was dressed all in black leather with long black high heel boots. Poor Prue nearly went weak at the knees at the sight, but of course it was no surprise to Anne or to Jennifer. They had talked quite a bit with Miss Hampson about how they might teach Prue more about being a sissy, and knowing that Prue was quite submissive they thought that some experience with a very dominant Mistress might be good for her. "So how is our little sissy today," said Miss Hampson as she took his hand and led him inside. "My, your mother and Anne have you looking very sweet. Has he got his belt on Jennifer?" "Not yet Janice. I thought that perhaps you could do a final adjustment check and then put it on him for us before we get on with his hair and other training." Miss Hampson reached for Prue and gently pushed him down so that he was kneeling before her. She then placed a very wide leather posture collar around his neck and locked it into place, noticing that the boy was surprised by what was happening but made no move to object. He really was a docile little thing when dressed as a girl she thought. Taken to the bedroom and made to undress she soon had him locked into his chastity belt after some minor final adjustment of the belt that ran between his legs. Then she buckled a strap between the back of his collar and the waist strap of his chastity belt making sure it was quite tight and restricted his ability to bend forward. Then she dressed him again and led him back into the lounge room. "Here he is. All locked up in his wonderful belt and I have added a strap to make sure he has to keep a straight back at all times, as we discussed. Worn frequently it will help him adopt a much better posture all round and we will see quite a profound change in the way that he walks." Prue found it very difficult at first to walk properly, but he said nothing and in fact it made him feel very safe and secure when he was fastened into his belts and collar in this way. He didn't understand why that it did, but he just knew that this was something that increased his level of pleasure no end. "I understand that you want to keep his hair reasonably short at this stage Jennifer, but I am sure with a little careful shaping we can make it very girlish indeed, particularly if we give him a perm that puts some waves into the top and around his ears. Shall we do that?" A short time later he was in a high chair while the women fussed about him washing, drying and then placing rollers in his hair with setting lotion and then drying it again before brushing it out lightly. The effect was magical and Prue was allowed to view himself in the mirror before his mother this time redid his makeup and told him to get down from the chair. ?My goodness. That has made a difference." Jennifer attached his leash and took him for a walk around the house and gardens, noticing the improvement in his posture and the way that he walked. What a darling he was she thought, and she kept him on the leash taking him with her wherever she went in the house for the rest of the day. She felt so powerful being able to control him this way, but she also felt an enormous amount of love and affection for her son as he was coming to grips with the changes in his life he was dealing with. "Did you see his reaction to my leather outfit. He loved it. Perhaps we should all look to become Leather Mistresses with him from time to time," said Janice with a big smile. Prue had already been put to bed in his nappies, plastic panties and nightie and collar, but it was Janice who had had the pleasure of doing this for him for the first time. She had left his chastity belt in place because, as she explained to him before tucking him in, ?accidents' were no longer allowed, and if he misbehaved in any way his mother had agreed that they would have to look at a more regular regime of punishment for him. The next few weeks proved to be very rigourous for Prue. Locked in the chastity belt, posture collar and the connecting strap he was made to work very hard around the house looking after the needs of everyone while dressed in his long maid's dress with the hobble skirt. When he had time off he was allowed to sit at the feet of one of the three women who inevitably locked him into his harness to keep him under her control. They noticed him becoming more and more docile, and he loved to be told to kiss their shoes or boots. It made him very excited to do these things but the control they had over him was such that he did not come once during the whole period at Miss Hampson's place. Jennifer wondered what would happen if he was given permission to come, but she was not ready to do that yet. He had to learn who was in charge. After a week back home the new outfit Jennifer had ordered for him finally arrived, and it was the Friday night after school that she helped him put it on. It was a harem girl's outfit, made entirely of soft pink plastic. The trousers were nice and loose but tight around each ankle and three bands of elastic held them high up around his waist. The short top exposed his midriff, and it had a collar with many ruffles of plastic around it coming high up under his chin. The long sleeves were loose as well, although tight around each wrist. Little anklets and bracelets with bells made it obvious whenever he moved, and strapless clear plastic shoes with 3" heels completed the outfit. He wore no underwear and no belt so he could feel the plastic against every part of his body as he walked from his bedroom down the stairs into the lounge, the tinkle of the bells ringing in his ears. Jennifer had spread a large wool rug and some cushions onto the floor and she told him to sit down and relax. She then chained him to an anchor point she had installed in the floor near the wall, and left him to his own thoughts and desires. She then went off to change into the leather outfit that she had purchased -a tight revealing leather halter top over a short leather skirt and knee length boots with 4"heels. She tied her hair into a ponytail and then clipped a short leather strap to a stud on her belt. She loved being dressed this way, and she hoped that Prue would like her dressed like this as well. Given his reaction to Janice he thought that he would. When she came back into the room he was lying quite still and she thought at first he may be asleep. But he wasn't and as he stirred to look at her dressed this way for the first time he was noticeably excited. She walked up next to him and with one simple command and response she knew their relationship had changed forever. "Lick my boots Prue. Lick them you little sissy." Without a word he did as he was told, and she could see him harden inside his plastic pants. "Keep licking them until I tell you to stop or I will use my strap on you," and she took the strap off her belt and showed it to him, giving him just a gentle tap with it on his bottom. As she hit him gently she could see him become even more excited as he ran his tongue over her boots, loving every minute of what he was being required to do for his beautiful mother. "Would you like permission to play with yourself darling?" "Yes mother." "What did you say Prue? Ask me properly." "May I please have permission to play with myself mother?" "No. I don't think so at this stage. Maybe later. Keep licking." The boy was horribly frustrated, but he obeyed as she thought he would, even if he was probably as excited about what was happening to him as he had ever been. Two hours later and he was in bed locked into his chastity belt. His emotions were in turmoil. He had wanted to come so badly, but he now knew better than to disobey his mother, or for that matter Mrs. Simpson or Miss Hampson. He was happiest when he was Prue and being controlled by one of the three wonderful females in his life. He ached inside to serve them and be with them. He wanted to please them and he wanted to look beautiful and, when allowed, sexy for them. He wondered again and again why he was like this, and how all this had come about, but he knew in the end he didn't really care. It was just the way he was and the way he would remain - a sissy. (to be continued)