Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Pre-2011 Sissy Stories => Topic started by: frillibabi on July 07, 2009, 05:00:04 AM
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part one of my first story! I will write more if it appeals to other readers
Remedial action
Part 1
It was mid afternoon on a hot day in the first week in July and Carol Walters was justifiably proud of herself. Yes, her husband had left her two years ago to live with the secretary who was young enough to be his daughter, and yes her 16 year old son, Simon, was behaving in a way that the charitable would attribute to his parents divorce, but Carol had finally managed to get promotion to supervisor in the office she worked in and the extra money would come in handy. Particularly as Simon’s father had become somewhat tawdry in his maintenance payments. There was a double benefit in that this was the first summer that Carol hadn’t had to arrange paid care and supervision for Simon, so the additional income would come in especially handy.
Carol was therefore particularly agitated when, just before her lunch break, the receptionist told her that her neighbour Elsie Stamford was on the phone. Elsie Stamford, or Mrs Stamford, as Carol always called her, lived in the next house to the Walters. Whilst Carol Walters had always addressed her as “Mrs Stamford” she was never aware of there ever having been a Mr Stamford. Elsie Stamford was now retired – Carol would guess she was in her late sixties, but was aware that she had retired as a headmistress of an infants school a few years before the Walters had moved into the neighbourhood.
“Mrs Walters, I ‘m sorry to disturb you at work but it was a choice of calling you or the police.”
“Whats wrong?” said Carol, the panic audible in her voice.
“I’m afraid its your son Simon. You know I look after the Wilson’s house opposite when the go away on holiday?” Carol Walters knew the Wilson family, nice people, 3 daughters aged 17, 15 and 12.
“Yes” said Carol.
“Well I was just popping over to check that everything was alright at the house and I caught your son climbing out of the window.” “Oh No!” Carol exclaimed. “Oh yes indeed” said Mrs Stamford. He had a bag with him. I’m afraid I decided I had better check to see what he might have taken. I’m afraid that its rather unpleasant”
“What?” exclaimed Carol, her mind running wild with the thought of what her son had been doing.
“The bag contained a large amount of the Wilson girls under wear – they seem to have a rather nice taste in teenage lingerie. There were some of the younger girl’s items too – frilly panties and lacy tights – that sort of thing. I have Simon at my house now. My first thought was to call the police, but I thought that perhaps you’d like an opportunity to deal with it first.”
It took all of Carol Walters’s restraint not to use expletives. Unfortunately simon’s interest in girl’s under wear and his willingness to steal it from the drawers of others was not news to her. She had found several items on previous occasions hidden under his bed or behind the bookcase in his room on routine cleaning forays. She had been troubled by the finds and questioned simon, but he had either been evasive or claimed that he’d just found them. It was only after a stay at her sister’s when her 17 year old neice had complained that a baby doll nightie set had disappeared – and turned up under simon’s bed – that she knew what was going on. What she didn’t know was what to do about it.
Now, however, something needed to be done, and seen to be done, if the Police were not to be involved.
“Thank you Mrs Stamford, I don’t know what has come over Simon. I guess he’s missing his father. I’ll come right over. I’m sorry you’ve been troubled.”
“Its not his father he’s missing Mrs Walters, it’s the firm hand of discipline. If you want that boy to turn out all right you need to take some action now. If you ask me you’ve been too soft on him since his father left. He’s been allowed to get away with murder. He needs taking down a peg or two. But its not for me to tell you how to bring up your son – I don’t suffer the embarrassment of his behaviour. We both know what your son intended with that clothing. It’s a dirty filthy habit and he needs to be cured of it. Whatever it takes.”
“I very sorry”, muttered Carol Walters, embarrassed that she was being thought responsible for her errant son’s behaviour. “You’re quite right, I should do something, I’m just not sure what.”
“We’ll if you need a hand, I’m quite able to help you out” said Mrs Stamford “but perhaps we can discuss matters once you’ve sorted out the immediate situation”.
“Yes, of course” said Carol Walters, “I’ll be right over, I’m leaving now.”
Carol Walters immediately approached her line manager and said she had to leave work for an hour due to a domestic situation. She could tell her Manager was unimpressed. As an unmarried male he had little understanding, and even less sympathy, for the plight of a single mother. Carol brooded on this on the 10 minute drive home. Why had Simon let her down like this? Hadn’t she got enough on her plate? Why couldn’t Simon act his age with some responsibility? Maybe Mrs Stamford was right, maybe she had been too soft and Simon needed taking down a peg or two. By the time Carol Walters pulled into her drive 10 minutes later she was near incandescent with rage. She was not going to debate the matter. She was going to take action.
When she arrived at Mrs Stamford’s house simon was sitting sheepishly in the hall. Mrs Stamford welcomed Carol and explained what she’d seen and handed Carol the bag she’d found Simon with. One by one the items were removed and admired by the ladies.
“I shall take the under wear back to the Wilson’s” said Mrs Stamford. I presume you will deal with Simon at home?”
“That’s what I had intended” replied CAROL.
“Very well – you may find the contents of this back useful” offered Mrs Stamford and she produced a small opaque plastic back. Carol looked inside. There was a large wooden hairbrush and a pair of pink rumba pants. The Woman exchanged a knowing look that worried simon who had quietly been witnessing the conversation, confident that he would be able to sweet talk his way out of the situation.
Carol Walters reached down and took Simon’s arm. “Come with me” and with that she led him out of Mrs Stamford’s house. To the front door of their own home. When she unlocked the door she pointed to the satairs and said:
“Go to your room now and wait for me”
“Oh mum I’m not a little boy anymore” replied simon.
Carol walked to where her son stood and slapped him firmly across his left cheek. Simon’s head was ringing with the blow but he heard her mother next words clearly enough.
“That is exactly how you have behaved, little boy. You disobeyed me and embarrassed me. Enough is enough. Now quick march if you know what’s good for you.”
Simon sensed something in his mothers tone and realised this was not the time to argue.
What was she to do? She needed the job and the money it brought. But Simon clearly couldn’t be left unsupervised. That would have to wait. First she had to deal with Simon then she had to apologise to her neighbour, Mrs Stamford and thank her for alerting her to the problem.
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Part 2
Simon was sitting on his bed reading a comic when his mother stormed in. Simon’s eyes were drawn to the hairbrush in her mother’s hand. He hadn’t seen it since he was 12 but the 4 years of its absence hadn’t dimmed the memories of its power. “Please Mum” Simon stammered – “I’m sorry about . .” His mother cut her off “Sorry? You’re going to be very sorry indeed my boy I’ve just about had it with you. You cannot seem to keep your hands out of your pants for more than a minute, you sneak into peoples private drawers and steal their clothing! You are a dirty little sissy w**nker, aren’t you? I’ve let things slide since your father left but I’m going to make up for that good and proper now – we’ll see how sorry you are then. Now get over my knees NOW! Stand up!” As you seem to like girls panties you can wear them whilst I punish you – maybe that will make you think twice before you behave like that again sissy simon! His mother held out the pair of frilly rumba panties Mrs Stamford had provided. She held them at waist height so that simon had to “high step” to get into them into them.
Carol stood back and glared at her son. “Just look at yourself – don’t you look silly? And she pointed to a mirror so simon could see himself standing wearing nothing but the frilly panties. Tear began to form in his eyes.
“Whats the matter sissy? Don’t like your panties?” his mother laughed. Well you’d better get used to them!”
“Come round here” Mrs Walters barked, indicating a place on her right. Simon stood crestfallen as his mother picked up the hairbrush by her side. “Please Mum” was all Simon could think of saying but he knew it was useless. His mother was furious, he could tell and nothing he could say would save imr from the spanking that was about to begin.
Carol Walters grabbed her frightened teenage son by the wrist and pulled him towards her. In a second Simon was forced over his mother’s lap and the punishment began.
Mrs Walters raised the hairbrush high in the air and began to wear of the pent up anger and frustration she had felt since her husband had left WHACK…. WHACK …WHACK went the hairbrush and “Ouch”…”Please” …”I’m sorry” cried simon. WHACK…. WHACK …WHACK. . . WHACK…. WHACK …WHACK . .
WHACK…. WHACK …WHACK. . . WHACK…. WHACK …WHACK WHACK…. WHACK …WHACK . . . “I’m sorry, I’m sorry I’m sorry” wailed simon but he was already beginning to cry and Mrs Walters ignored her pleas. WHACK…. WHACK …WHACK. . . WHACK…. WHACK …WHACK . . WHACK…. WHACK …WHACK . . . WHACK…. WHACK …WHACK. . . WHACK…. WHACK …WHACK . . WHACK…. WHACK …WHACK . . .
By now tears were freely flowing down simon’s face. His bottom and the top of his thighs were dark red. he was wailing and kicking his feet and screaming something about being a good boy in future. Mrs Walters paused for a moment and listened to her son’s sobbing. Maybe that was enough she thought. “OK that’s enough for now – now I want you in the corner with your nose against the wall and your hands on your head. Simon stood up and pulled up the frilly panties. “Simon” she barked, “Did I say you could rub your bottom?” “No Mum” Simon whispered, the tears still running, “Hands on head immediately” ordered Mrs Walters and as soon as he complied Mrs Walters brought the hairbrush down on Simon’s thighs. WHACK…on the left thigh then WHACK on the right thigh then back to the left…WHACK. . right. WHACK…left. WHACK …right WHACK . left WHACK. . right…. WHACK .The pain was immense. Simon was finding it hard to breathe. The tears were in full flow. His mother stopped. Grabbed him by the ear and marched him, to the corner of the room.
“Now get your hands up on your head”. Simon obeyed. “You will stay there until I come back, . . If you move . . . well I think you can guess what will happen.”
Mrs Walters walked back to the doorway of the bedroom. She turned and looked back at her son. The Red marks on her bottom were beginning to take on a bluish tinge. The marks contrasted deeply with the whiteness of his shaking lower thighs.
Right she thought I’d better go and apologise to Mrs Stamford and thank her for alerting me.
Part 3
Carol thought it would do no harm to tell Mrs Stamford how she had dealt with Simon. She knew Mrs Stamford held firm views on the discipline and didn’t want to be thought too liberal. Mrs Stamford however already knew the fate that had befallen Simon – the sound of the hairbrush on Simon’s bottom – and Simon’s reaction to it - had travelled to Mrs Stamford’s veranda where Mrs Stamford was sitting with a pot of tea.
As Carol Walters approached Mrs Stamford’s house, she was greeted by Mrs Stamford and the words “Your far too lenient with that child”. Carol Walters, unaware that Mrs Stamford had heard simon’s spanking replied, “Well I’ve just put a stop to that. I’ve just given simon the spanking of his life”. Mrs Stamford laughed, “Well, I heard you give the child a few licks, but it’s hardly the discipline the child needs. A boy like your simon needs a good radical approach to discipline . . root and branch. It’s far too late to just rely upon the hairbrush or paddle . . No that boy needs re-educating in discipline so he knows exactly what he is, a sissy. . . your just too soft with her.”
Her? Carol Walters was staggered. There she was proud of herself for, at last, getting up the courage, and the anger, to discipline her son, and her neighbour was saying it was too little to late and calling the boy a sissy girl. “Well what do you suggest?” Asked Simon’s mother. “Well” said Mrs Stamford, you need to devote some time to disciplining him – lengthy sessions of re-education and training. It will take time.And he needs to be dressed appropriately to remind him exactly what he is. You cant have him breaking into neighbours houses and going through they’re intimate clothing can you? No that child needs to be kept under constant watch – and dressed in a way he’s not likely to want to go out much!”
“But I don’t have time” said Carol Walters “I should be at work now. I took this job because I thought Simon was old enough to leave on his own. . How wrong was I. What am I going to do? I need this job.”
Mrs Stamford looked at Carol Stamford and smiled. “Don’t worry, if you want I will look after Simon. I have quite a lot of experience in dealing with boys like your Simon and if your son thinks he can get away with his nasty habits he can think again. I think your son needs a baby sitter for the summer to make sure he doesn’t get up to any more trouble. And you can go out to work, or even with friends in the evening, knowing that Simon has done the chores around the house and hasn’t got up to any mischief.
Carol Walters thought for a moment “but Mrs Stamford, Simon hardly ever helps with the chores he . .”
Mrs Stamford cut her off “Oh I can be very persuasive. he’ll be happy to help with chores when I’ve finished with him. I ‘d like to start know, if you don’t mind. Perhaps you could bring Simon over and the you can get back to work we get better acquainted.”
“Why certainly, I’ll just go back and tell him to get dressed,” said Carol Walter’s, who was still bemused at the idea of her son doing chores.
“Oh no, there’s no need to get him dressed – just bring her over as he is. The humiliation will do him good and he won’t be needing any of his clothes, I’ve got a number of suitable outfits for him here”
Carol Walters had to admit that she was shocked at the thought of dragging her 16-year-old son out into the street dressed only in a pair of pink frilly panties and into her neighbour’s house, but she was still reeling from Mrs Stamford’s suggestion that she was too lenient with Simon and that Simon’s behaviour was partly her fault. The woman spoke with authority. Maybe it was time she handed Simons correction over to someone else. Maybe the humiliation would do Simon some good. Even so, she was a little surprised when she heard herself say “Very well. I’ll go and get him now!”
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Part 4
Simon had been horrified as his mother had dragged him by the ear down the stairs and into the street. He’d pleaded with his mother not to humiliate him, but her pleas had fallen on deaf ears. He was screaming and sobbing and asking where they were going and his fears were not eased when his mother told him Mrs Stamford would be looking after him for a while. Simon had never liked Mrs Stamford. The woman was old fashioned and clearly didn’t approve of him. The thought of Mrs Stamford seeing him in her present condition, tear stained face and crimson bottom and thighs made Simon feel physically sick. But there was nothing he could do, such was the vice like grip his mother had on her ear.
Mrs Stamford was strangely calm and told Simon that she was sure that he regretted his conduct and that it wouldn’t happen again. Mrs Stamford said that perhaps, just so that Simon knew how displeased she was, she ought to give him another spanking. Simon had protested again, but this time half heartedly. He knew it was useless. Whilst he’d had a chance of talking his mother out of punishing him he knew instinctively that Mrs Stamford was altogether another prospect.
Mrs Stamford had suggested that Carol Walters returned to work and left Mrs Stamford to get on with the spanking.
“Don’t worry dear, he’ll be a lot quieter if your not here. You go back to work and leave us two to get better acquainted. When you get home tonight we can have a chat about the rest of the summer holidays”
Carol Walters thought about it for a few seconds and agreed.
She turned to her son who was still blubbering “Good bye Simon, I’ll be back later, now don’t give Mrs Stamford any trouble”.
“Oh don’t worry, I’m sure we’ll get along fine” beamed Mrs Stamford.
Simon didn’t like the look on Mrs Stamford’s face one bit.
Mrs Stamford walked to the window and watched Carol Walters drive away, leaving Simon stood naked but for his pink frilly panties in the middle of the room. Once she saw the tail lights of the car turn the corner of the street she turned and looked at Simon. “O K young lady, time to get that spanking out of the way” and with that she moved a high backed dining chair into the centre of the room, sat down and motioned to her lap. Simon hesitated for a second.”Young lady?” he croaked. “Why yes, Simone, who else but a young girl would be wearing pink frilly panties? I can only imagine that you were stealing the Wilson girl’s frillies as you like them so much and don’t have your own” Simon blushed and couldn’t think of an answer
“Now, Come here this instance” boomed Mrs Stamford “or I shall fetch my cane”.
Simon had never experienced the cane and didn’t want to; he was frightened and scared, cowered by Mrs Stamford’s authority. he scampered over to Mrs Stamford’s right side. Mrs Stamford roughly pulled him down over her lap and reached across with her left arm to pull his right arm back across her back. There would be no attempt to try and protect his bottom! Then the spanking began. SMACK . . Simon could not believe such pain could be imparted with just the bare hand. SMACK . . .SMACK . . . SMACK . . .SMACK . . SMACK . . .SMACK . . SMACK . . Simon began his wailing and sobbing again. . . SMACK . . .SMACK . . SMACK . . “its no . SMACK . . .SMACK . . SMACK” said Mrs Stamford, keeping up an even tempo with the spanks . . . SMACK . . .SMACK . . SMACK . . “you should have thought of that” . . . SMACK . . .SMACK . . SMACK “before you stole” . . . SMACK . . .SMACK . . SMACK . “this morning” . . . . SMACK . . .SMACK . . SMACK . . “I’m sorry, I’m sorry” pleaded Simon . . “. SMACK . . .SMACK . . SMACK” . . . “I’ll be good” . . . SMACK . . .SMACK . . SMACK . . “I promise” added Simon . . . SMACK . . .SMACK . . SMACK . . . “Oh I don’t doubt that!” said Mrs Stamford, “just another six . . . for the moment, anyway.” . SMACK . . .SMACK . . SMACK . . . SMACK . . .SMACK . . SMACK. Mrs Stamford released Simon’s right arm and unceremoniously pushed him off her lap onto the floor. Simon lay there in a flood of tears. His nose was running and he was gasping for breath. His bottom felt on fire.
“Hell” he thought, he would never have gone into the Wilson’s house if he’d known that would happen. However if he’d known then what Mrs Stamford had in store for him he’d have wished that he’d never been born! “Up little lady” commanded Mrs Stamford “Up now, or do you want some more?” Quickly Simon got to his feet and was led by the ear by Mrs Stamford to an empty corner of the room. “I want you up straight, no slouching, nose in tight to the corner, and hands on head. You will stay there and compose yourself until I have decided you can turn round. Do you understand ?”
Simon sniffed. “I asked you a question. Do you understand, child?”
“Yes” mumbled Simon
“Oh I think we can do better than that, can’t we child?” said Mrs Stamford, planting a hefty swipe across Simon’s right calf. The impact on Simon was immediate and he quickly replied “Yes Mrs Stamford”.
“That’s better, but I think as we’re going to get to know each other a lot better you had better call me Aunt Elsie. Now I am going upstairs to find you some suitable clothing to wear when we go out. Whilst I am out of the room you are NOT to move a muscle.”
Simon heard Mrs Stamford leave the room and climb the stairs. he was tempted to look over his shoulder but thought better of it. he could hear drawers being open and shut. he tried to catch his breath and stop crying but the pain in his bottom and thighs kept reminding him of his sorry state. he heard Mrs Stamford come back downstairs and go into the kitchen. Mrs Stamford was on the phone to someone. he couldn’t hear what was being said other than Mrs Stamford seemed to be arranging to meet someone. After what seemed an eternity, but was in fact only about half an hour Mrs Stamford entered the room and told Simon he could put his arms down and turn around.
“Well we cant go out with you naked, can we child, so lets get you dressed.” Said Mrs Stamford.
Mrs Stamford held up a pair of lacy white tights. “Mmm” she said thoughtfully, “I think we’ll have the panties over the tights – then everyone can see those lovely frills, eh? What do you think girly?”
Simon stammered “please Mrs . . Aunty, please no!”
“Oh yes indeed, its just what a silly little thief like you needs, a public outing, so everyone knows what happens to sissy who steal panties. Now into these double quick or its over my knee again”
Simon was in no state to put up a fight and gingerly put on the tights. The material scratched his swollen bottom. Mrs Stamford took hold of the hem and yanked the crotch up, ensuring the fit was snugger – and more uncomfortable.
“No lets get the frillies back on” Again Simon was required to high step into the panties as Mrs Stamford held them open for him.
“Now I know you know what this is” smirked Mrs Stamford as she held up a lacy white training bra that belonged to the youngest Wilson girl. “Arms out sissy” barked Mrs Stamford.
Next came the blouse. It was made of a silky white material, it had puffed long sleeves and large frills on the front and collar and buttoned up the back.
Mrs Stamford stood back and admired Simon, who was now looking and feeling uncomfortable. She stepped forward and placed a white hairband, with a single pink artificial rose attached over his head.
“Yes” she said, “all we need now is a pair of shoes”.
“What” wailed Simon “What about trousers,?”
“Girls don’t wear trousers simon! And your going to be a pretty girly aren’t you!” laughed Mrs Stamford.
In desperation Simon pleaded “well then a skirt, please . . I’ll wear a skirt”
“Oh no” laughed Mrs Stamford “girls undergoing tights punishment don’t get skirts. “My, my Sissy, you do have a lot to learn”.
“You can’t take me out like this!” cried Simon
“Can’t Simon, I’ll show you what I can and cant do” Mrs Stamford fixed Simon with a steely grin.
Simon felt a chill run down his back.
Simon realised that he was about to be publicly humiliated. His knees were beginning to shake and his stomach was turning.” Please Mrs . . Aunt Elsie . . I need the toilet,” he whispered.
“Wait here” said Mrs Stamford forcefully. She left the room and returned a few seconds later with a yellow plastic potty which she placed on the floor in the centre of the room.
“Very well, girl. Get on with it” said Mrs Stamford.
Simon found it all so hard to believe – he looked at the potty and then at Mrs Stamford.
“Please Mrs . . Aunt Elsie . . please let me use the toilet”
“It is either that or nothing. Now what is it to be young lady? We haven’t got all day. You have precisely one minute or I take the potty away and then we go out. If you wet your panties in public that will be your concern”
Simon hesitated and saw where he stood. Between crouching down and using the potty in front of Mrs Stamford or possibly wetting his pants in public he knew which he would choose. he stepped forward and lowered the tights and pants before squatting, rather inelegantly, on the potty. he tried to forget Mrs Stamford was there watching him as he relieved himself, conscious of the noise his pee was making as it hit the inside of the potty. Mrs Stamford was all to keen to make her presence known.
“Stay squatting when you’ve finished, dear” she said, “Just tell me your done but do not get up”.
What was she doing now, Simon thought. “I’ve finished” said Simon almost inaudibly.
“Good girl ” cooed Mrs Stamford as she stepped towards Simon, opening her handbag. She withdrew a tissue from her handbag, bent down and proceeded to wipe Simon dry. “Now you can stand up and pull up your panties and tights”. When Simon had complied she picked up the part filled potty containing the now used tissue and told Simon to empty it down the toilet in the hallway, wash his hands and return.
When Simon got back Mrs Stamford had a pair of black leather platform shoes with T Bar strap for Simon to wear.
“I know they’re not fashionable, but they are all I have that will fit you. Actually I think they go rather well with the outfit. They’re faintly ridiculous – and that’s the idea. Put them on and then we’re off shopping. Oh I nearly forgot!” and with that Mrs Stamford picked up a piece of paper on which was written “I steal girls panties” and pinned it on to the back of Simon’s blouse.
“ Come on girl, don’t dawdle, unless you want to go out without your top on!”
Simon, by now, knew not to push it.
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Part 5
Simon had felt that he would be unable to bear the public humiliation of having to go shopping in her tights punishment outfit. he hadn’t realised that Mrs Stamford had intended the outfit to be only the beginning of simon’s humiliation. As they went about the town Mrs Stamford held Simon by the wrist. Whenever they bumped into someone that Mrs Stamford knew Simon was introduced as a “sissy nephew who needed some attitude adjustment”. The interested acquaintance would then be told that Simon had already had his bottom spanked today and knew what to expect if he misbehaved again. On one occasion Simon had been made to lower his tights and panties to show the inquisitive acquaintance his inflamed and sore bottom, only to be told, “I’m sure you deserved it”.
Neither had Simon been prepared for the nature of the shopping. They had visited the pharmacist store where Mrs Stamford had purchased a number of jars and packets. Simon had been made to go to the counter on his own and request a packet of disposable diapers in his size. he had nearly refused but had caught the look in Mrs Stamford’s eyes when he had hesitated. The assistant, who was probable only a couple of years older than Simon hadn’t helped by asking if Simon wore them during the day, or just at night. Simon, who hadn’t worn them at all, and wasn’t sure of Mrs Stamford’s intentions, mumbled something about occasional nights. The assistant seemed to enjoy Simon’s discomfort and asked if he wanted a dummy as well, and pointed to a selection on the wall. Simon was lost for words and felt himself blushing furiously. But Mrs Stamford, who had just come to the counter with her full basket, and had overheard the conversation said “What an excellent idea . .My niece will take 3 – do you have them in an extra large size?”
The assistant said she did, put them in Mrs Stamford’s basket and began ringing the purchases through the till. All the purchases were put in a carrier bag except for the disposables, which wouldn’t fit. Whilst the assistant searched for a larger bag Mrs Stamford said “Don’t worry, my niece will carry them as they are”. Simon was all too aware that everyone would know, dressed as he was, who the diapers were for. Was there no end to his shame? If Mrs Stamford got her way, of course not.
As they walked through the town Simon began to realise the humiliations that Mrs Stamford had in store for him. Surely she wasn’t intending to put Simon in diapers. It wasn’t fair. Maybe Mrs Stamford would listen to reason. Perhaps if he spoke to her. “Mrs . . Aunt Elsie, please don’t put me in diapers” whined Simon “I don’t need them, honest”. Mrs Stamford stopped and looked at Simon. A smile appeared on her face. “Lets see if you don’t need them Sissy, but I think you will” laughed Mrs Stamford. She took Simon by the wrist again a led him into a large department store. Simon was conscious again of people staring at him. Some, girls and boys of his own age, or younger, openly pointed and laughed.
Mrs Stamford approached a young store assistant and enquired where the baby changing rooms were. The store assistant looked at Simon and smiled before explaining they were on the 3rd floor. Mrs Stamford led Simon up the escalators and located the room. “Come on Sissy, hurry up, we haven’t got all day” chided Mrs Stamford. Simon entered the changing room. It was small and designed to be used by parents changing their children’s diapers.
A washbasin was in one corner and a long wide raised bench ran the length of the room which was covered with a plastic covered cushioning. In the other corner was a chair. Mrs Stamford put the shopping bags down and sat on the chair.”Ok sissy, come here now.”
Simon was frightened; he hoped this wasn’t going to be another spanking. Nevertheless he knew better than to disobey Mrs Stamford. When Simon was standing in front of her Mrs Stamford rose and inserted her hand down the front of Simon’s tights, feeling his crotch. “Well you feel dry enough now, I’ll admit” said Mrs Stamford. Then she grinned again, “Right Sissy, up on the bench on your tummy”. Gingerly Simon climbed onto the raised bench and lay down. Mrs Stamford reached into the shopping back and produced a pair of latex gloves, a jar and a packet. She walked over to Simon, reached round his hips and pulled the tights down to Simon’s knees. “OK girl, I want you up on all fours” she said. Simon didn’t know what was happening, but complied immediately. As he was doing so Mrs Stamford was donning the latex gloves and opening the jar. It was a lubricant and Mrs Stamford inserted her gloved right index finger first in the jar and then in Simon’s anus. Mrs Stamford’s finger made a slight “plopping” sound as she inserted and withdrew the finger ensuring that the anus was well lubricated. Simon was stunned by this latest assault on his dignity but could think of no protest that would not result in more pain. He could hear Mrs Stamford behind him tearing open the cardboard packet.
Had he seen the packet he would have learnt that it contained laxative suppository. He would have read that the suppository would take effect within 10 minutes. One of the contents of the packet was now being inserted by Mrs Stamford into Simon. With her task completed Mrs Stamford gave Simon’s bottom a playful swat, and she proceed to draw the panties and tights back up his thighs until they were back, snugly, in place.
“Now then Sissy, shall we see if you can control yourself, or whether you need diapers? I’m guessing on diapers, but its up to you” Mrs Stamford laughed. Simon didn’t realised his predicament. He didn’t know what a suppository was, never mind the effect on his bowels.All he knew was it was awful to be seen in town dressed as he was, but he didn’t want the embarrassment of being seen obviously having pooped in his pants. He could feel something happening in his bottom and began to realise that Mrs Stamford had done something to loosen his bowels. He turned to Mrs Stamford and heard himself say “Please Aunt Elsie will you put a diaper on me now”. Mrs Stamford smiled sweetly and said “No Sissy, it will have to wait until we get home. I’ll tell you what though, I’ve got something just incase you have an accident.”
Then Mrs Stamford reached into the shopping bag and produced a pair of plastic lined white satin rumba pants. She held them up for Debby to see. There was row upon row of white lace sown onto the seat of the pants and little satin bows adorned the legs and waistband. “Aren’t these the cutest Sissy? You’d better pop them on in case you have an accident.” And with that Mrs Stamford began pulling down Simon’s pink frilly panties and replaced them with a similar but plastic lined pair that crinkled as Simon moved.
Anyone who was paying attention to Simon, and quite a few were, would have noticed that he was adopting a curious gait as he left the store with Mrs Stamford. The truth was he was already conscious of the suppository in her anal passage beginning to dissolve and do its work. he was walking trying to clench his buttocks together in the hope, much misguided, that he could somehow delay events until he was back at Mrs Stamford’s. That was a 20 minute drive away, and the car was parked some 10 minutes from the store. The laxative packet had suggested that results could be achieved in about 10 minutes, and they were right. As Mrs Stamford and Simon entered the car park, and Mrs Stamford opened her bag to retrieve her keys she was aware that Simon was breathing quite fast and taking shallow breaths. Simon had that look of concentration on his face that suggested he was channelling all his will into avoiding the force of nature. Mrs Stamford looked at him and smiled “I think my little friend is doing its business !” Mrs Stamford laughed at her own joke, but Simon couldn’t see anything funny. he stood next to the car as he felt himself expel something large and soft into the gusset of his panties. he was embarrassed and shocked. he didn’t know what to do but wanted to cry, so that’s what he did.
Mrs Stamford, aware that the Sissy was now broken, put her arms around the him and said “there, there. We’ll get you home and bath you and change you.” She got out some plastic sheeting, put it on the back seat and got Simon seated in the car. The last thing Simon really wanted was to have to sit in his soiled pants, but there was no other option. With Simon securely seated in the back seat Mrs Stamford drove home..
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Part 6
As soon as they were through the door of Mrs Stamford’s house Simon was told to go upstairs to the large bathroom and wait there. Gingerly, conscious of the contents of his panties, which he’d been sitting in for the last 20 minutes, he climbed the stairs and entered the bathroom. he didn’t have to wait long for Mrs Stamford to arrive. Mrs Stamford was now wearing a long plastic apron and the latex gloves.
“Well, little miss “I don’t need a diaper”, it seems we’re in a right mess now!” she sneered and then chuckled at the joke.
“Do you want Aunt Elsie to change you?”
Simon said nothing; he thought the answer was obvious. How could he stay as she was?
“Well, cat got your tongue, answer me, or shall I leave you all night in them!” said Mrs Stamford.
Simon quickly realised this was no joking matter. “Please Aunt Elsie” Simon stammered “Please . . don’t leave me in my panties . . Please change me.”
Mrs Stamford smirked. She walked over to Simon and roughly pulled the White frilly plastic lined Rumba pants down to his knees.
“Step out of them” ordered Mrs Stamford. Simon obliged.
Mrs Stamford went to the large walk in cupboard in the corner of the bathroom and returned with a plastic covered changing mat which she placed on the floor.
“Lie down on this on your back” barked Mrs Stamford.
Mrs Stamford bent down and began drawing the lacy tights down over Simon’s bottom. When they were at mid thigh level he was instructed to draw his heels back so as to raise his knees, and to arch his back. This enabled Mrs Stamford to remove the tights.
Mrs Stamford looked down at Simon lying on the floor. It was clear now – both by sight and smell that Simon had messed his panties. “Not such a big girl as you thought are we miss panty pooper” Mrs Stamford taunted. “Well I have ways of dealing with girls like you, nasty dishonest girls . . who like to mess they’re panties!”
Mrs Stamford now pulled Simon to his feet by his hair. Simon yelped but didn’t resist - he couldn’t. Forcibly Mrs Stamford pushed Simon into the shower cubicle and quickly turned on the cold-water outlet. The water began to wash the waste loose, aided in part by a long handled bath brush being wielded by Mrs Stamford. Every few seconds Mrs Stamford would bark a command which would be punctuated by a blow with the back of the brush if Simon wasn’t complying fast enough.
“Turn” . . . CRACK …. “left” . . . CRACK . . “turn” . . . CRACK.
When the water was turned off Simon was clean but freezing and sore. Mrs Stamford held up a short white towelling robe and announced “You will put this on and follow me. With that Mrs Stamford bent down and picked up the plastic changing mat and walked out of the bathroom.
Simon followed Mrs Stamford into a small bedroom. The room was decorated like a small childs room. Mrs Stamford placed the mat on the single bed and told Simon to take off his robe and lie on his back. Simon obeyed, fearful of the return of the bath brush. Soon he felt the cold latex gloves of Mrs Stamford invading his bottom again. “This will help you relax dear”, she cooed “you appear a little nervous” Mrs Stamford laughed. Next Simon felt the bulk of the diaper as it encased his throbbing bottom as Mrs Stamford attached the self-adhesive fasteners at the waist. Mrs Stamford turned and opened a drawer in the dresser under the window. She held up a pair of pink, semi opaque tights. “Yes, I think these will do nicely” she said to herself.
Simon felt his feet being put in the tights and Mrs Stamford drawing them up and over the diaper. Mrs Stamford turned and fetched another pair of plastic lined rumba pants like those she’d been wearing earlier, but this time in a canary yellow colour, and drew them up and over Simon’s diaper. “And finally” said Mrs Stamford “your pretty nightie” and she held up a very short, very frilly, nylon baby doll nightie. “Hands up”. Simon raised his hands above his head to enable Mrs Stamford to put the ridiculous garment over his head and on to him.
“Now wait there” said Mrs Stamford “I’ll be back in a couple of minutes” and she left the room.
Simon didn’t know if it was the fear, or the embarrassment but he was beginning to feel a little lightheaded. he could feel, what ever Mrs Stamford had placed up his bottom was beginning to dissolve and causing a gentle tingling sensation.
Within a couple of minutes Mrs Stamford had returned and she was holding a rather outsized babies feeding bottle complete with teat. “I’ve brought you a little drink to help settle you, Sissy” said Mrs Stamford smiling again. “Now I want you to sit up and let me feed you. Open wide now, or do I have to fetch the bath brush . . . no I didn’t think I would.” And the teat was put in simon’s mouth. The drink was warm and milky, and slightly sweet. Mrs Stamford held the bottle inverted over Simon’s mouth and placed her arm around him, pulling her towards the bottle.
It took some 5 minutes and some encouragement, and threats, Simon to empty the bottle, but when she did so Mrs Stamford remarked “Well Done”.
Then Mrs Stamford dropped the bombshell. “Well you should be ready for a little nap now. The pessary I placed in your bottom is a combined sedative and laxative, and the drink contained a diuretic and muscle relaxant. They should be taking effect by now. Its bed time for you now even though its only 4 pm. I’d get a good rest because tomorrow I intend to start your re-education in earnest. I’ve spoken to the Wilson’s. They were very annoyed to hear tat you had violated the privacy of their home and the girls were shocked to hear that you had been through their underwear. They are returning tomorrow. I have told them of your punishment so far and Mrs Wilson says that she will ensure that the girls get their own opportunity to have some “pay back time”. Your mother knows and approves. I have told her that you are a silly sissy who will always be drawn to ladies panties and will only end up in serious trouble unless strictly controlled. I know your type and can assure you, you can look forward to a summer of strict sissy punishment which will control you though I doubt it will cure you!”
“Oh no!” Simon thought. Today had been so humiliating but at least he’d avoided meeting anyone he knew. The Wilson girls were neighbours and went to the same school as him. If they saw him as he was now they would be bound to talk – and they would too! They were so haughty and always sneered at him, even the youngest girl, that’s what had excited him, what had made him think of getting some of the lovely underwear he knew they would wear. The thought had excited him, made him stiff. He knew what he would have done with that underwear, but then again, so did Mrs Stamford!
“Now up you get and under the covers – tomorrows another day” ordered Mrs Stamford.
Simon rose on uncertain feet. he felt wobbly. Mrs Stamford drew back the sheets blankets and quilt and Simon climbed in. he felt overdressed in the diaper, tights, rumba pants and nightie and he realised she’d be hot with the bedding. Mrs Stamford fetched another quilt and tightly tucked it under the mattress on both sides of the bed making it difficult for Simon to move.
“Its just so you don’t fall out” Mrs Stamford announced. With that she walked to the windows and drew the heavy curtains together. The only light came from a dim bulb in the centre of the ceiling.
Mrs Stamford looked down at Simon snugly secured in the bed “Now let me tell you this my girl. I don’t enjoy changing diapers, but I will do so when it’s needed. However I always spank, firmly, whenever I change a diaper, so remember that. The more times you need changing, the more times you get spanked. That’s fair isn’t it” But Simon couldn’t answer as Mrs Stamford had just inserted the large pacifier into his mouth, and Simon knew better than to spit it out.
“Now you have a nap little one, and I’ll come back and see you in the morning. Your mother will be back soon and I need to discuss your bedtime schedule with her. I think a girl like you should be in bed by 3 everyday to stop you getting crabby. I’ll speak to her when she’s back.”
With that Mrs Stamford turned, switched off the light and closed the door behind her.
Simon was left in the dark bedroom, swaddled in the bedding and beginning to perspire.
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Part 7
Mrs Stamford descended the stairs to her living room. She bore a rather contented look. She was pleased with her day. Pleased to have trapped another “fly” in her web. If Simon thought that he had been unlucky being seen by Mrs Stamford leaving the Wilson’s house that morning he was wrong, very wrong. Mrs Stamford had been watching Simon for several months now. She knew all about his dirty habits of stealing girls underwear and she could make a very educated guess of what he was doing with the various items he’d collected. Elsie Stamford knew the tale tell tale signs of an embryonic Sissy when she saw them, and Simon displayed quite a few. What was the “tell”? Was it the way he liked to grow his hair long? Or that he didn’t like his nails cut short? Perhaps it was the way he lack any real friends, and certainly not the boyish sporting ones. But the real give away was when simon had failed to pull the curtains closed in his bedroom the night his mother had gone to the School Parents meeting. There was only a gap of about a foot. But that was a big enough gap for Elsie Stamford. Equipped with her ziess binoculars that she kept to ensure she knew what was happening in the neighbourhood Elsie had had her thoughts confirmed when she caught glimpses of Simon dressed in stockings and garter belt and playing with his pen*s. That was over a month ago. Since then she’d diligently watched him. She knew he was fascinated by the Wilson girls. She’d seen him ogle the dainty underwear on the washing line at the Wilson’s house, pretending he was mending his bike. And was it Simon’s good fortune that the Wilson’s had left a small downstairs window open as they drove away that morning? Of course not. Mr and Mrs Wilson were extremely security conscious. They had checked all the windows and doors before they left. No, the window was open, because Elsie Stamford had opened it, knowing that silly Simon would not be able to help himself. Not only that, but Elsie Stamford had made sure that the Wilson girls frilliest, daintiest, most feminine under wear was placed at the top of their drawers so that they would be on immediate view once the drawers were open. She had set the trap and need only wait for Simon to act – it was like watching a moth drawn to the light she thought.
So there were no surprises for her when she encountered Simon exiting the window. Well there was a little surprise, perhaps. Simon had not only removed the frillies from the drawers, he’d also rooted about in the laundry basket and taken a couple of pairs of the older Wilson girls soil panties and pantyhose. Was she surprised by Simon’s choice of these items? Well perhaps a little, but she wasn’t shocked. She knew a thing or two about Sissies and she knew what dirty things they could get up to.So she was going to have fun with this one – yes indeed. She enjoyed humiliating vunerable young men and boys and reducing them to simpering sissies trained to serve their betters.
She entered her living room and reached for the photo album in the bookcase. “Yes” she thought “lets have a little trip down memory lane” and she began looking at the photos reaching back over 3 decades. On the pages could be seen the apprehensive faces staring back, like rabbits caught in the headlight. On the first page was the image of a rather leggy individual dressed in patent shoes, white ankle socks and very short canary yellow dress. Peeking from under the dress could be detected several layers of net petticoat forcing the skirt of the dress up and out. The hair was in bunches, tied with white lace edged ribbons and small white lace gloves adorned the hands. To the casual observer the image appeared to be that of a teenage girl, although the clothing and hair was too juvenile for her age – perhaps it was a halloween costume some might think. But Mrs Stamford knew the real truth. The photo was of Paula – or Paul, as he’d been known when she first met him – Mrs Stamford’s first success. He had come to lodge with her as a fresher at college. He too was light fingered when it came to lingerie. He too had learnt to regret it and had been taught the error of his ways. Where was Paula now? Mrs Stamford thought. Oh yes, she remembered. He was overseas, working as a personal maid for that rather successful business woman that she had met through the Club. Yes, that’s right. Karen Winters was her name. She ran a rather up market lingerie business – how ironic that Paula should have ended up there! She remembered receiving a grateful Christmas card from Miss Winters some years ago enclosing a photograph of Paula in his maids uniform complete with lacy cap. A warm glow filled Mrs Stamford at the thought. Yes she had notable success as a sissy trainer over the years. And upstairs, in bed, safe and secure, was the latest recruit. She’d have her fun with him for a couple of months and then she could contact the Club again to see what vacancies there were. Simon, given his age and looks, once trained would be very sought after indeed. Yes she would have to sort out Simon’s mother, Carol Walters. But that wouldn’t be too difficult. She knew from experience that once she found a Male for Carol who “tended to her needs” she’d not miss the troublesome son, particularly one that seemed to be an embarrassment.
Yes, she thought. Time to progress the plan.
Elsie Stamford picked up the phone and called Carol Walters. “Mrs Walters, Elsie Stamford here . . . yes, he’s fine, just a little washed out, what with the crying and the shock of his predicament. Listen, it might be better if he stayed here tonight, in fact I’ve put him to bed already . . . yes I know its early, but he’ll benefit from it. . . its no trouble at all. Why don’t you go out and have some fun – you deserve to”
At the other end of the phone Carol Walters paused and thought for a moment. She hadn’t had a proper night out since her husband left her. She hadn’t felt like it and besides Simon had always acted up if she tried to leave him alone for any length of time. And Bill Nicholson, the Head of Finance had been flirting with her recently and suggested meeting for a drink. Why not she thought!
“Yes Mrs Stamford, yes I will, thank you so much for taking care of Simon”
“Oh there is no need to thank me at all” replied Elsie Stamford.
Mrs Stamford had a few further phone calls to make. Tomorrow was to be a busy day and arrangements had to be made.
Upstairs, lay Simon. Had he known Mrs Stamford’s plans for him he would not have slept a wink. As it was, the sedatives and the laxatives gently went to work as Mrs Stamford had intended. Indeed everything would happen as Mrs Stamford intended.
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First class story with all the excitment and skill of an accomplished author. Wonderful enjoyment - well done and thank you!
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PART 8
Simon had slept well thanks to sedatives Mrs Stamford had provided. He woke to Mrs Stamford’s cooing voice “Common Sissy, its wakey wakey time. How’s my little panty thief this morning?” At first Simon was confused, he didn’t know where he was. He felt uncomfortable. He was conscious of the cold clamminess surrounding his groin and bottom. But as the sight of Mrs Stamford, hands on hips, staring at him with a broad grin, registered with him he began to remember where he was, and what had happened yesterday. His heart sank.
“Well” said Mrs Stamford “what do we have to say?” Simon looked nonplussed. “Is Sissy shy then? Is she?” asked Mrs Stamford in the manner one would use to address a baby. Simon just stared back at her.
“Well I know how to get this little girl to make some noise” and with that Mrs Stamford pulled back the covers and delivered two crisp blows to Simon’s upper thighs. Simon yelped in response. “Ah sissies found her voice!” laughed Elsie Stamford. “Well aren’t you going to say morning to your Aunty Elsie?” Simon mumbled a “Good Morning” with little enthusiasm. Another two crisp slaps were delivered by Mrs Stamford’s meaty hand. “Not good enough Girl!” she exclaimed, followed by another cry of pain from Simon. “When you talk to me you will do so in a soft, “little girl” voice, with a slight lisp . . and you will address me as Aunty Elsie. Now lets try it again. Good Morning Sissy” and she stared intently at Simon, her right hand raised ready to fall on Simons already reddened and sore upper thigh. Simon starred back. His first thought was that she was crazy, that if his mother knew she’d call the police and have her arrested. Then he remembered why he was in Mrs Stamford’s house. No he didn’t think it would be a good idea for anyone to contact the police. Mrs Stamford knew how to hurt him, and that trip to town yesterday was awful. He realised that the best thing to do would be to humour her.
In his best “little girl” voice Simon lisped “Gooth Morthink Aunthy Elthie”. Mrs Stamford beamed at him. “That’s much better . . much better . . you’re a quick learner Sissy . . and you’ll need to be if you want to avoid a hot bottom!” she laughed.
Right lets get you up and cleaned. Then I can give you your first spanking of the day sissy.
“But I hav’nth donth anythink wong yet! Pleath don’t spwank me!” exclaimed Simon, remembering to use the voice.
“Oh, Sissy” laughed Mrs Stamford, “You’ve done plenty wrong. You’ve just not been caught in the past. We’re just doing some “catch up” and making sure you get all the spankings you deserved in the past before we give you the ones you deserve now.”
Simon began to frown. “Now little one, I don’t want any sulking, understand. You are going to get what you deserve, that’s a promise from Aunty Elsie. Lets get you up and out of those stinky wet diapers. If you’re a good girl and take your spanking properly I might just let you wear big girls panties today. Would you like that sissy?” Simon just lay there not knowing what to say. “Well, diapers or big girls panties – unless you’d like to go out naked? “ Simon knew she meant it. It was a limited choice but he knew which he’d prefer “Big girls panthies” he lisped. “Good” smiled Mrs Stamford. Well we’ll see after the spanking.” And she bent down over Simon and began removing the tights’ rubber pants and wet diaper. As Simon eased his hips into the air to enable Mrs Stamford to remove the sodden diaper she noticed that his pen*s was stiff and erect. Even so, it could have measured only about 2 ½ inches in length and was barely thicker than one of Mrs Stamford’s fingers.
“I think sissy is all excited about wearing big girls panties, isn’t she?” Mrs Stamford sniggered. “That’s why her little cli*ty is all stiff and swollen” and with that Mrs Stamford took Simon’s erect member between her thumb and forefinger and pinched it. Simon winched in pain and bucked his hips. “Now now sissy, settle down,” Mrs Stamford said quite sternly. “You are not to touch that without my permission. Do you understand” The look she gave Simon said it all. “Yeth” Simon replied, and he nodded his head several time to let Mrs Stamford know that he wouldn’t be chancing his luck on that front.
“Now then, stand up sissy. Right go and fetch the chair and place it on the mat.” Simon walked to the corner and picked up the straight-backed chair and carried it to the centre of the room. He was naked from the waist down but still wearing the short white baby doll nightie. Mrs Stamford walked up to him. “So sissy, its not just panties you like, is it? No, sissy likes dirty worn panties too? Eh?” Simon blushed. Well perhaps this will remind you that you are not just a panty thief, but a panty sniffer too!” and she produced a pair of the worn panties that Simon had stolen from the Wilson girls’ laundry basket. They were ivory white hipsters, in a satin material, with the legs and waist trimmed in a white lace fabric decorated with red rose buds. Mrs Stamford held them up in front of her for Simon to see, her forefingers of each hand pulling the waist open. “I think you’ll recognise these” she smirked “you can wear them whilst I give you your spanking”.
Simon raised his right foot waiting for Mrs Stamford to lower them so he could step into the panties. “Oh no, no, no”, laughed Mrs Stamford “You are getting your spanking on your bare bottom sissy. When I said you could wear them I meant this way.” And with that she placed the worn panties over Simon’s head. She took a moment to adjust them so that Simon’s nose was pressed against the crotch of the panties. Simon immediately recognised the mixed smell of body fluids and perfume. Once again his pen*s began to swell. The panties covered his eyes and he could see little but was aware that Mrs Stamford had now seated herself in the chair. He felt a sharp pull on his arm and fell over Mrs Stamford’s lap where he remained for the next 5 minutes or so whilst Mrs Stamford and a smoothed backed hairbrush went to work.
Whilst Simon’s demeanour immediately before the spanking could be described as quiet or even sullen, his behaviour immediately after the spanking would probably be best described as “agitated”. He was bawling his eyes out, his nose was running and he was fighting to catch his breath. He knelt on the floor at Mrs Stamford’s knees, where she had unceremoniously dumped him, the panties still on his head as he furiously tried to rub the pain from his hot and swollen bottom.
“I think we can take these off now,” announced Mrs Stamford as she removed the panties from his head. “You will sit on the naughty stool for 20 minutes and compose yourself. Go sissy” and she pointed to a low three legged stool in the corner of the room. Simon hurried across and lowered his bottom onto the stool. As he made contact he immediately rose again in pain. “Sit child!” bellowed Mrs Stamford “and be still, or I’ll give you something that will make you move”. Simon lowered himself onto the surface of the stool again and realised that the cause of his discomfort was the layer of fine sharp sand embedded in the varnished surface of the stool.
Mrs Stamford walked across the room and towered above him. She had her hands on her hips as she looked down on him. “Here’s a tissue so that you can dry your eyes and blow your nose sissy. You really are a big cry baby aren’t you? Maybe you’ll get used to your spankings after a while” and she produced a pink tissue and held it out for Simon to take.”
“Now I want you to stop crying so we can do your make up. We have a very busy day today and lots of people to see. So, 20 minutes and then I want you bright eyed and bushy tailed. Understand poppet?”
Simon didn’t understand. As he sat on a scratchy stool nursing a sore bottom dressed only in a short frilly nightie and crying his eyes out he realised he was very very confused. What confused him the most was that whilst he was in pain, humiliated and scared his pen*s was standing to attention and rock hard. It literally throbbed with excitement.
Mrs Stamford noticed it too. But unlike Simon, Mrs Stamford wasn’t confused. She’d seen it all before. She knew that Simon’s libido was reacting to what Simon’s brain could not possibly contemplate. She was giving Simon what he needed even though he didn’t know it, and wouldn’t recognise it.
“Now, not a peep out of you for the next 20 minutes, or we’ll start again” she firmly advised Simon. “When I come back I want to find those tears gone and that tiny thing” and she pointed to Simon’s groin “less excited. If you can’t control it I will. Understand?”
“Yeth Auntie” Simon responded. He wasn’t sure he could comply though!
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Part 9
Twenty minutes later Mrs Stamford entered the room. Simon had managed to gain control of his emotions again and whilst his bottom was still extremely sore and he had a headache and sore throat from the crying at least his erection had subsided.
Mrs Stamford had a bundle of clothing with her that she placed on the bed and a two handled child’s drinking cup which she offered to Simon saying “I brought Sissy a little drinky. You’d like that wouldn’t you Sissy, it will help calm you down”
Simon gratefully took the cup with a “thwank you Aunty” and began to gently sip its contents.
“Now Sissy, we have a busy day today and I have to get you ready. We are going to beauty salon to have your hair and nails done first and then to the dress makers. If there is time and you behave I might take you for a glass of milk and a slice of cake. Won’t that be fun?” The thought of another outing into town caused Simon to visibly blanche and his stomach immediately began to knot”. Mrs Stamford could see Simon’s discomfiture and laughed. “Oh Sissy, your not frightened of going into town are you? There is nothing to worry about, Aunty Elsie will hold your hand all the time and introduce you too all the people we meet!” That’s what Simon was afraid of!
“So Sissy, over here and lets get your face made up before we select your pretty clothes for town” and she pointed to a little stool placed before the dressing table upon which were arrayed various jars and boxes and tubes.
“Now Sissy, I think we shall get the girls at the salon to give you a proper make up session but we need something to make you look nice. I didn’t tell you, but we’re getting the bus into town today. I thought I would leave the car at home.”
Simon swallowed hard. He wasn’t even going to be able to hide in the back seat of the car on the journey into town. He would have to wait at the bus stop and be seen by everyone else. He could feel himself blushing.
“Oh how sweet Sissy” smiled Mrs Stamford “That looks very suitable. Yes, a little rouge to the cheeks makes you look very cute and girly. But first the eyes.”
Mrs Stamford spent a good 15 minutes applying the various contents of the tubes and jars during which she hardly spoke other than to periodically exclaim “Yes, Yes” or “very pretty” or even “what a cutie!”.
When she finished she held a mirror up for Simon to see her handiwork. “Well Sissy, don’t you look just the little princess you are? And she beamed with obvious self-satisfaction. Simon looked at the mirror. He didn’t recognise himself. His eyes had been made up and the lids shaded to make him look very wide-eyed and innocent. His lips had been made to look very full and plump and the rouge increased the “doll like” image. One sight of Simon’s face would cause any passer by to stop and stare, and smile at the youthful, naive innocent image it conveyed.
“I hope Sissy likes her new face,” said Mrs Stamford. “Well to be honest” she added “I don’t really care if you like it or not Sissy, I like it and that’s all that matters, isn’t it Sissy?” Simon was so shocked he said nothing. “Well Sissy, do I need to help you talk again?” Simon understood immediately “No Aunty, thwank you Aunty” he lisped.
“Now then Sissy lets get you dressed. Even though you were very noisy during your spanking I think I’ll let you wear the big girls panties rather than a diaper, but there better not be any accidents, understand?” Simon nodded, “Yeth Auntie”.
“Now then Sissy lets get you dressed. Even though you were very noisy during your spanking I think I’ll let you wear the big girls panties rather than a diaper, but there better not be any accidents, understand?” Simon nodded, “Yeth Auntie”.
“Now up you get, I think we’ll have this on first” and she held up a white bustier. It was lightly boned for shape, semi, transparent with a satin front panel. The bra cups were edged with a delicate lace trim as were the shoulder straps and attached suspenders. “Arms out . . come on girl, don’t dawdle or do I need to fetch my hairbrush?”
Simon immediately thrust out his arms and Mrs Stamford placed each through the shoulders straps and began hooking up the fasteners at his back.
“Now these” and Mrs Stamford picked up a pair of bridal lace topped stockings, white, and semi opaque the lace extending down a full 5 inches of the thigh.
Simon gawked at the stockings. “p p pleath Auntie” he stuttered. Mrs Stamford gave him a hard stare. “Put them on now Sissy, or else! And make sure you are careful putting them on, they are very delicate and I don’t want them laddered.”
She looked at Simon who had now seated himself on the stool again and was rolling up the stocking before placing it over his foot. Mrs Stamford smiled “Yes I thought you’d know how to do it sissy. Not the first time you’ve worn stockings is it? Eh?” and she laughed out loud causing Simon to blush again. But the blood wasn’t just flowing to his cheeks. Once again he felt his member stiffen and extend. It was if it had a mind of its own. Mrs Stamford noticed of course. She would have been surprised if it hadn’t happened. That didn’t mean that it was to be excused, or that she couldn’t use it to embarrass Simon further.
“What is that?” she barked, pointing to Simon’s groin. “Did I or did I not tell you to control it?” Simon shamefully stared at the floor. “What did I say I would do if you didn’t control it? “Simon said nothing “Well Sissy? I want to hear you” “You thed you’d control it Aunty” mumbled Simon.
“Yes I did. And I intend to do so. Come here” and she pointed the index finger of her right hand to a spot on the floor immediately in front of her “Now!”.
When Simon was in front of her Mrs Stamford turned and opened a drawer in the dressing table and removed a couple of items. She turned to face Simon and looked him straight in the eyes before speaking gently “I think that this will stop that filth habit” and speedily, before Simon could flinch or pull back, Mrs Stamford had grabbed his scrot*m with her left hand and with her right hand placed a hinged stainless steel ring behind his testicles and deftly snapped the ring shut. She turned and picked up two further items – a small metal cigar shaped” cage” and a small padlock. She held each item up for Simon to see.
“You see, Aunty always keeps her promises!” and she bent down and placed the cage over Simon’s now shrinking appendage before attaching it to the ring by means of the padlock. In less than a minute Simon’s member had been encased and securely locked away. It really now was out of his control!
“Now, some big girls panties, eh? You’d better not have any accidents in these!” warned Mrs Stamford, and she held up a pair of white satin panties decorated with red polka dots and edged in lace. “Come on, sissy, step into them” and as Simon obeyed Mrs Stamford edged them gently up over the stockings and cage and pulling them gently up into Simons crotch.
“I think we should finish dressing Sissy, don’t you?” Mrs Stamford did not wait for an answer. She went to the wardrobe and removed a white layered tulle mini petticoat. “This will look very pretty I think.” And she held it out for Simon to step into. As it was eased up Simon’s calves and thighs the softness of the tulle on the stockings Simon experienced a frisson which caused his pen*s to swell within its cage until it found the limits its permitted freedom. The pleasure of the experience immediately turned to discomfort proving the old adage “what goes up must come down”.
“Nearly there Sissy” said Mrs Stamford as she admired the image of the Bimbo Sissy before her. “I think we’ll go with the sailor suit, yes that will work very well.” And she turned to the wardrobe again and removed a hangar bearing a ridiculous and grotesque pastiche of a sailors suit. The main body of the dress was white and pleated below the waistline. There were navy blue short-capped sleeves and a matching “peter pan” collar surrounding the round neck. A wide navy blue ribbon surrounded the waist and hung down at each side –from its length it obviously was meant to tie at the back in a large bow. The skirt section looked extremely short and Simon was aware that not only his petticoat but probably the lace tops of his stockings would be visible below it. But it was that hat that looked most ridiculous. It was a white brimless hat, with navy piping and a badge on the front embroidered with a gold anchor surrounded by the words “all the nice boys love a sailor!”. A navy blue elasticated chin strap was attached to each side of the hat.
“Sweetly pretty” proclaimed Mrs Stamford, as she lowered the dress over Simon’s head.
“And these too” said Mrs Stamford as she produced a pair of white lace gloves. “and this” as she handed Simon a small white shoulder bag which was edged in navy to match the dress and emblazoned with a gold anchor to match the hat. “You’ll need to take care of your bag, Sissy, it contains lots of useful things you might need!” Simon had no idea what might be in the bag and if Mrs Stamford thought they’d be useful he really didn’t want to know.
Taking his hand she led him to the mirror so that he could take in the full force of the image he portrayed. “What a delicious little sissy girl you make sweetie” she commented. Simon stared at his reflection as she placed the hat snugly on his head.
“My my Sissy,” laughed Mrs Stamford “its just as well we used the waterproof mascara” as she noticed the tears well up in Simon’s eyes. “Come along Sissy, shoes on and then we must be off to catch the bus. The hated platforms from yesterday were produced and buckled on Simon’s feet.
“Right Sissy, we’re off,” announced Mrs Stamford, and with that she gripped his wrist in her hand and propelled him down the stairs and out of the door into the street.
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Please juest keep writing. It is very good. Please include early bed punishment as outlined before and especially tights punishment as you have already described. Opaque tights work best with panties beneath. Regardless though, I enjoy all you w rite. You are keeping us on edge waiting what the Wilson girls will do. Will they turn him intoa baby with their suggestions and help in making baby clothes? Any way you like a great story is unfolding here...
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PART 10
The journey into town had been excruciatingly unpleasant for Simon. First he was led by the wrist by Mrs Stamford to the bus stop where they waited for the bus to arrive. It was a pleasant day, but there was a gentle breeze that made Simon acutely aware that he was dressed in the flimsiest of outfits. At times he could feel the breeze catch and lift his petticoat and dress and whilst it would have been natural to try to hold the hem of his skirt down he was constrained by the fact that one hand was securely gripped by Mrs Stamford and the other was being used to ensure that his shoulder bag was kept in place. Simon knew his stocking tops, and on occasions his panties were being displayed to all and sundry and there was nothing to do but endure the same of it. I noticed that three or four cars slowed down as they approached the bus stop and he saw the male drivers leer hungrily at him – one car actually circled the block twice!
Worse still was the group of boys, about Simon’s age, who walked past on the other side of the road and “wolf whistled” at him. One shouted “hello sailor!” at him in a mocking way whilst another chanted, “show us your panties”. Simon was petrified that the youths would cross the road and accost him. He pressed closer to Mrs Stamford for security and she, conscious of Simon’s vulnerability “ whispered to him “Awe is Sissy scared of the rough boys? Don’t fret petal, Aunty will keep you safe. Or would you like me to call them over so you can show them your big girl’s panties?” and with that she looked Simon straight in the face and smiled. “No pleath don’t Aunty” was all Simon could say “Pleath don’t, pleath!” and Mrs Stamford chuckled to herself, enjoying the Sissy’s dependence upon her.
Things had not improved when they were joined at the bus stop by a young woman and a little girl who Simon guessed was about 8 or 9. As they had joined the queue Simon had shuffled up, closer to Mrs Stamford who still held his wrist. Mrs Stamford had turned to smile at the new arrivals and then loudly said “Say good morning to the lady and her daughter sissy”. Simon was shocked at the attention Mrs Stamford was drawing to him. He truly wanted the earth to open and swallow him. In a faint voice, the best he could command in the circ-umstances he croaked “Good morning Mith”. The mother and daughter looked at him strangely but then Mrs Stamford said in a crisp voice “I don’t think they heard you Sissy, I’m sure you can do it louder, or would you prefer to curtsey?”
Simon immediately spoke up – the thought of having to curtsey in the street to this stranger and little child was too horrible to contemplate. “Good morning Mith” he piped up. The little girl looked at him and asked “Mummy why is that girl wearing such silly clothes? I can see her panties!” Simon’s cheeks burned with shame and Mrs Stamford answered the little girl’s question by telling her that Simon was not a girl but a boy who was being punished for stealing and doing other naught nasty things.
She told how Simon had been put in diapers the day before but was being allowed big girls panties today as a treat because he had taken his spanking well that morning. Whilst Simon had kept his eyes firmly on the ground whilst Mrs Stamford was disclosing his shameful predicament, he could not but be aware that the little girl’s mother was coldly staring at him. When Mrs Stamford completed the account of Simon’s punishment to date and his misdemeanours the lady said “I’m pleased to see that someone is prepared to take the time and trouble to cure this wicked boy of his filthy habits. Should you need any assistance, I would be only too happy to provide it” and she introduced herself to Mrs Stamford and gave her a phone number. As the bus arrived Mrs Stamford told Simon to take out his purse as he’d have to ask for his own ticket and count out the pennies she’d placed there to pay for it. Not surprisingly everyone on the bus became aware of Simon as he stood at the front lisping to the driver that he wanted a “twicket to town” and then counted out the fare in pennies whist the driver looked at him and laughed muttering “thought I’d seen everything! Wait till I tell the boys back at the depot about this one!
As Simon shuffled up the aisle to join Mrs Stamford he heard the little girl say to her mother “Mummy, Mummy can we visit the sissy boy soon and watch him being spanked? I’d love to see him cry, can we Mummy?” to which the Mother replied that she would ask the sissy’s Aunty and was sure that it would be possible.
As Simon slumped, rather unlady like into his seat besides Mrs Stamford he realised, too late, that his short dress had ridden up and the tops of his lacy stockings were clearly on display as was an inch or too of exposed thigh. Mrs Stamford leant to him and said, a little to loudly for Simon’s taste “I can see that you will need some lessons in deportment Sissy . . that is unless you want everyone taking you for a slut!”
Simon could here two girls sitting behind him roar with laughter in what he thought was a rather unladylike manner. Whilst he couldn’t really appreciate it, he did realise there was a certain irony in the situation.
When they reached their destination Simon was aware that the, by now, rather full bus was solely concerned with him, and in particular with the area of his body between knees and waist. As he followed Mrs Stamford down the aisle to the exit he was aware of titters and whistles and stares.
As he stepped of the bus, timed to perfection, nature provided a sudden gust that lifted his skirt and petticoat revealing the effect of his underwear to all those seated on the kerb side of the bus. Had it not been for the elasticated chin strap on his hat that too would have been displaced. Mrs Stamford just turned and looked at him, hands on her hips, and admonished him “Well I can see that you are quite the exhibitionist, aren’t you? You obviously not only enjoy wearing girls underwear, but want everyone to know it too. I shall be happy to oblige” and she reached for Simon’s wrist and, gripping it firmly dragged him along the kerb towards the doorway of “Little Miss Beauty Salon” . As he was dragged inside the doorway he noticed the quote above the doorway “the one stop salon for pageant princesses and their Moms”
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Sorry for the delay - I have been enjoying a vacation!
here is the next instalment - as usual feed back is welcome and most encouraging.
PART 11
As Simon was propelled into the Salon by a firm push from behind by Mrs Stamford he became, once again, the object of attention for everyone else. Not that the salon was by any means as busy as the bus – there were 3 girls of ages between 8 and 13 and one mother being attended to by the same number of staff members. The staff comprised two girls who looked as though they were in their late teens, a lady in her twenties and another, who seemed to be in charge and was much older. The older lady approached Mrs Stamford with a broad grin
“Hello Elsie, how good to see you again – it must be what, nearly a year since you were last here?”
“Oh longer than that Aril, closer to two years I’d say, but I’m very well. How’s business?”
“Oh up and down, up and down. You know that pageants aren’t as popular now and girls seem to be growing up a lot earlier so our style of beauty isn’t as popular as it was twenty years ago but . . we still have a regular trade in the old sissy treatment” and at that she laughed and looked at Simon. “I guess this little specimen is you latest, Elsie?”
“Yes indeed”
“How did you come by him if you don’t mind me asking?”
“I caught him stealing my neighbours daughters’ underwear – he lives across the street from me”
“tut tut . . does it have a name?”
“Not yet, at present I just address it as sissy – I’ve not settled on a name yet.”
“Well” said the owner, addressing Simon, and bending forward to speak directly to his face” “My name is Miss Aril, and this is my salon, and we are going to give you the full sissy beauty treatment today and make you all pwetty! Yes indeed, well take away all those ugly boyish looks and make you into a pwincess . . yes we will!. Just you have a little seat with your Aunty Elsie and as soon as Julia and Stacy are free” and she looked over to the two teenage girls Simon had noticed before, “They’ll make a start on you”
Simon noticed that the two girls were each working the younger girls. As they heard their names mentioned by Miss Aril they had looked up and towards Simon, then they had looked at each other and laughed. Something intuitive told Simon that he could expect no sympathy from those girls and he squirmed in his seat beside Mrs Stamford. Her response was to simply say, quite curtly “do sit still sissy, unless you want me to give you something that will make you fidget? Here you can look at this whilst you wait” and she thrust a magazine into Simon’s lap. He looked down at it. It was a comic – but not the sort he’d ever seen or read before. Whilst his preferred choice was superhero’s and action men, this one was called “the misadventures of a super sissy” and the cover was a drawing of a man dressed in diaper, frilly pants and bonnet being pushed around a park by two school girls whilst various onlookers joked and laughed.
After about 5 minutes – which seemed a lot longer to Simon, Miss April returned to where Simon and Mrs Stamford were sitting. Julia, who was tall and buxom, accompanied her. She wore a white polyester tunic dress with a V-neck and stand up collar. The dress was short – about mid thigh and she wore tan pantyhose and white high-heeled shoes making her look even taller than her 5’9”. Her hair was blonde, and pulled tightly into a knot at the back of her head making her face look large. As natural for a girl working in a beauty salon her make up was generously applied and the application of the bright red lipstick and the high arching eyebrows gave her a striking appearance.
“Right,” said Miss Aril, “we’re ready for sissy now. Julia, would you like to take her down to the treatment room and get her started whilst Stacy finishes off”
“Go on then Sissy – go with Julia, she’ll take care of you” urged Mrs Stamford.
Simon rose and followed Julia across the salon. Before they had taken more than a couple of steps Mrs Stamford called “Oh wait Julia” and when she turned Mrs Bradford held up a small key and smiled “I think you may need this”.
Julia and Mrs Stamford exchanged a knowing smile as Julia dropped the key into the pocket of her tunic and turned again to lead Simon away.
As Simon followed Julia he could hear her gently humming and as she walked her hips swayed and she gently swung her arms. If Simon had not been walking behind her he would have seen that she had a broad smirk on her face. She’d only ever assisted Miss Aril with Sissy treatment before. This was to be the first time that she was in charge. When she’d been told the day before that a new sissy was being brought in for an appointment she knew it was going to be a good day, but when Miss Aril had told her that she could take charge she just couldn’t wait. She’d lain awake in bed most of the night excited at the prospect. She’d found it so thrilling and had indulged herself at the prospect of the forthcoming fun. One day, she thought, she’d be able to acquire a sissy of her own. What fun she’d have then. For now, however, she’d have to make do with the opportunities that came her way. And this Sissy was the best opportunity she’d had so far. This was going to be so much fun!
She led Simon down a long corridor. He was acutely conscious of the rhythmic click of Julia’s heels as she confidently strode ahead. As they reached a pair of double doors she pushed them apart and turned holding one half open.
“Come on, in here . . . we haven’t got all day” she said impatiently. She was eager to get started. Eager too to ensure that she had impressed her authority over the sissy before Stacy arrived. She liked Stacy, and she was fun, but she didn’t want it thought that she couldn’t handle the sissy alone.
The room was tiled from floor to ceiling and a long treatment table ran down the centre of the room. There were numerous wall cabinets and a stainless steel washbasin against the wall. Simon noticed various rings hanging down from secure fixings on the ceiling.
“Right sissy” said Julia, deciding it was time to take command of the situation “lets have this little dress of and have you stripped down to your underwear” and with that she came round the back of Simon and began to undo the dress fastenings. Simon was too subdued to put up any resistance. If truth be told he found Julia very exciting. Whilst he was very embarrassed that such a good looking girl was undressing him and that he was wearing such an embarrassing outfit he, once again, became aware that his member was beginning to swell and assert its presence causing Simon to wince in pain. Julia could not contain her laughter. She knew why this sissy was wincing. “Oh dear sissy. . Can’t control your little stiffy? Well, we’ll sort that out soon enough!” and she pulled each arm of Simon’s dress down freeing his arms before pulling the dress down below his waist.
“Now step out of the dress,” she instructed him
Simon lifted each leg in turn allowing Julia to remove the dress which she place on a hangar and hung from a hook on the back of the door. She stood and looked Simon up and down – her hands placed on her hips. “Pretty, pretty undies sissy” She commented in a not unfriendly way. Then she walked up to Simon and, much to his confusion she put on hand up his petticoat whilst pulling him in towards her with the other arm. As she held him in this embrace Simon instinctively tried to struggle and pull away. He didn’t like her wandering hand invading the privacy of his panties. It was only causing him more excitement with a resulting pain as his pen*s grew to the maximum capacity of its cage. He could feel her hot breath as she gently whispered in his ear “oh is Sissy just a little tease then! I know your sort . . you lead them on and make them all excited and then you go all coy and prim and proper! That’s it Sissy? Your just a little c*ck tease, aren’t you?”
Simon tried to pull away again. He tried to free himself from the embrace but Julia continued “careful sweetie, if you don’t behave yourself and do as you are told I shall tell Mrs Stamford that you grabbed my breasts and tried to put your hand up my skirt! I know she’d believe me – after all why should I lie” she laughed “I think you’re in enough trouble already, don’t you?” Simon knew she’d be believed – he could guess Mrs Stamford’s reaction too. She was right. All he could do was passively submit to this groping. “That’s better Sissy” Julia cooed “I knew you’d understand” she laughed. “But don’t worry, I was only teasing you . . I prefer real men” and she laughed again. “But sissies do have their uses in service . . as you’ll find out in due course.” And with that she withdrew her hand and released Simon.
“Ok, strip naked and then I want you on your back on the treatment table”
As Simon complied the tears began to flow again. A few days ago he would have given everything to be alone with a beautiful girl like Julia. He had fantasised about girls like her – the elder Wilson girl was very similar and his furtive imagination had fuelled many an hour when he had lain in bed playing with himself. He imagined them standing above him looking down at him whilst he was able to catch glimpses of their lacy underwear beneath their skirts or dresses. But here he was, being mocked and humiliated by such a girl. And the lacy underwear was being worn by him. Mrs Stamford had caught him and knew all about his dirty thoughts and now he was paying the price.
For the next 10 minutes Simon was subjected to an embarrassing array of treatments that involved the removal of all his body hair and the introduction of various tubes and fluids into his bottom. At regular intervals Simon was allowed to rise and expel the fluids, which he did by squatting on a cold stainless steel potty.
Julia was now acting rather matter of factly. She had made a few more embarrassing comments – such as remarking on Simon’s “freshly spanked botty” and how he deserved “another dose” for being such a “limp wrested panty waist” but by and large she quietly busied herself with her work, humming gently to herself when not barking out commands to Simon.
When Stacy finally entered the treatment room Julia was well on with the tasks. Simon was now thoroughly clean, internally and externally. He had been fitted with a medium sized but plug and Julia was applying, by means of a strong adhesive, a pair of small artificial breasts to Simon’s chest. The breasts were made of a latex material filled with gel and Julia had precisely matched the colour to Simon’s skin tone so that to anyone who did not undertake a careful examination they would look as though they were his own.
“Good” said Julia, at Stacy’s arrival “I was just about to apply the vagina. I’ll need a hand”
Stacy looked at Simon and smiled “Wow Julia, what a brilliant job! Those boobs look so good. I see you’ve given him the smaller size with the puffy nipples. He looks what? About 14?”
“Yes, that’s what Mrs Stamford wants until he gets used to them. Evidently she plans on working him up to the Super Bimbo breasts in due course. She thinks this one has Slut potential!” and with that both girls laughed in unison. Simon didn’t really understand what the girls were saying. He was eyeing the false vagina that Julia held. It too was made of latex matched to his skin tones.
Julia applied a generous coating of adhesive to the back of the vagina. As she did so, Stacy took hold of hid member with her thumb and forefinger and pulled it. Julia moved towards Stacy holding the false vagina in her right hand. Simon watched her as she gently squeezed it at the top and bottom, causing it to gape open, like a split tennis ball. She held it above Simon’s groin and Stacey let go of his little pen*s. Julia squeezed the vagina again and said “ready?” When Stacey replied “yep” two things happened. Julia pushed the gaping vagina onto Simon’s groin and Stacy, nimbly inserted her thumb and forefinger into the gap and pulled Simon’s pen*s through. As Julia pushed hard down on the vagina waiting for the adhesive to set Simon experienced a variety of pain and discomfort – his groin burnt from the adhesive, his pen*s hurt as it was firmly trapped by the side wall and “lips” of the false vagina, and his balls ached as they were forced up an into the base of the contraption. He moaned and winced, moving his hips about.
“Hush Sissy” urged Stacey “We’re nearly done now”. After 3 minutes Julia relaxed the pressure and examined her handiwork. Simon’s body was transformed. Not only was there a total absence of any sign of male genitalia but in their place was a very convincing vagina with the head of his pen*s slightly protruding and giving a very convincing impression of a cl*toris. “That’s brilliant,” exclaimed Stacey “Wow you’d think he really was a girl now”.
“Yes” said Julia “well the body does, but I think he could do with quite a bit of work to his hair, face and nails. Lets get this little sissy dressed and back up to the salon to finish her off.
So Stacey picked up Simon’s underwear item by item and supervised his dressing. The panties were pulled up Simon’s waist and adjusted so that the gusset sat correctly over his new vagina and when both girls were satisfied that his bra, panties, stockings and garter belt were safely and securely in place, he was instructed to step into the dress which the girls then secured him into. His shoes were buckled onto his feet and he was led back along the corridor into the salon.
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Sorry for the delay in posting and thanks for your comments.
As Simon emerged through the doors back into the main part of the salon he was met by the smiles and grins of Mrs Stamford and Miss Aril.
“All done are we? Enquired Miss Aril to which Julia loudly announced that the sissy was sorted out “down below”
“I hope sissy gave you no trouble,” asked Mrs Stamford
“None that I couldn’t take care of” replied Julia. In fact Julia was mildly disappointed that Simon hadn’t been a little bit more rebellious and shown some spirit that might have justified her applying a hard backed hairbrush to his bottom But then he was a sissy – if he had been a real boy he wouldn’t have allowed himself to that embarrassing treatment thought Julia.
“Now then, just the hair face and hands, and we’ll be finished with the little sissy” observed Miss Aril.
“Good” replied Mrs Stamford “If you can be as quick as you can – we’re due at the dressmakers in just under an hour. So much to do to get the sissy ready.”
“What are you planning? Something special?” Enquired Miss Aril.
“Well remember I told you that I’d caught sissy stealing the underwear from my neighbours house whilst they were away? Well they return this weekend, and I’ve told them on the phone that I’d bring sissy over for afternoon tea so she can apologise to the girls for violating their personal clothing and we can discuss how amends can properly be made. I want to get her a new party frock for the occasion so that she is looking at her cutest when the girls see her for the first time. It will make it easier for them that way – imagine the horror if they thought their panties had been taken by a real boy! No this way is better”
Whilst this conversation was going on Simon had been guided to an empty chair where the girls lost no time in washing and perming his hair and manicuring his nails. The chair in which Simon was seated was, unusually, not facing a mirror, so he was unable to see what was being done by the girls. Every so often he would be told to “look up” of “hold steady” as some procedure was performed – some painless, others causing mild discomfort – whilst the girls chatted between themselves and making the odd comment such as “oh, how sweet” and “yes pretty . . very pretty” The worst part was when he felt Julia inject something into the corner of his lips – as he flinched she said “Aw, that was just a little prick . . but then that’s what you are, isn’t it” and both girls had laughed and had to stop work for a minute or two until they could compose themselves enough to continue.
Simon could feel some lipstick being applied to his now, nearly numb lips. When she’d finished applying it Julia turn the chair round though 180 degrees so she could view her handiwork. Simon could see she was pleased – her eyes widened with approval and she wore a broad grin. She put her hands on her hips – causing her top to tighten and her br*sts appear more prominent. She moved her head from side to side and then bent down to whisper something to him. He could feel her warm breath on his ear, he could smell her fragrance and those ample bre*sts were just inches from him. Simon wondered what it was Julia intended to say – perhaps she wanted to say how much she sympathised with him, or how she would help him escape from Mrs Stamford’s clutches. Simon had convinced himself in that moment that Julia liked him and would help him. So it was a surprise, and shock to him, when she heard her say “sissy, I have just given you a pair of the most perfect c*cksuc-ker lips” and then she pulled back and laughed.
When Simon was finally led back to the reception area even the staid and sober Mrs Stamford found it difficult to suppress an expression of mirth at simon’s appearance.
“I just love what you have done with her lips” Mrs Stamford said, proffering her credit card to pay for the salon treatment. “Is it permanent?” she enquired. “Semi” replied Miss Aril. “You’ll need to bring her back in a couple of months for some follow up treatment, otherwise her appearance will regress”
“We wouldn’t want that, would we” smirked Mrs Stamford, and she fixed Simon with an hard stare and in a loud voice commanded “Come Sissy – to the dress makers” and with that she firmly grasped his wrist and led him out of the salon and back onto the High Street where once again Simon was subjected to jeers, wolf whistles and the odd car horn which made him even more nervous than before
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Simon’s leg felt decidedly unstable as Mrs Stamford led him by the wrist up the High Street. “Nearly finished in town” announced Mrs Stamford, without looking at her charge, “and then we can get you back for a little nap. But first we need to get you measured for your party outfit”.
Once again Simon had difficulty knowing precisely what Mrs Stamford meant. But he knew enough to guess that any party to which he was invited would be a deeply embarrassing and humiliating event.
Suddenly, as they reached a plain doorway market “Edith Bottomley – Dressmaker and alteration specialist” Mrs Stamford stopped and looked at Simon. The mirthful look she had given Simon as they had left the Salon was gone and once again she fixed him with a “no nonsense” stare.
“Sissy we are about to go upstairs to Mrs Bottomley’s. I expect you to do as you are told and not embarrass me. If you do you’ll know what to expect” and with that she suddenly landed a crisp blow on Simon’s exposed thigh, leaving a distinctive red handprint where it landed. Simon flinched and nodded. He wasn’t sure what was happening to him. He wasn’t enjoying it, but he was learning that there was nothing he could do about it that wouldn’t make it worse.
Mrs Stamford opened the door and began to lead Simon up a narrow staircase. Simon was aware that if anyone entered behind they would have had a clear view up his short petticoat skirt and seen the fully frilled seat of his panties.
As Mrs Stamford opened another door at the top of the stairs and led Simon through a bell was activated. A small plump woman, who Simon guessed was in her mid fifties looked up from a sewing machine and smiled at the new arrivals. Simon could see a young girl, probably in her early twenties; emerge from a storeroom behind carrying a roll of pink satin fabric.
“ Good Morning Mrs Stamford. We’ve been expecting you,” announced the small lady.
“Thank you, Mrs Bottomley” replied Mrs Stamford. “This is my new charge,” she said turning to look Simon up and down. Simon was acutely aware that he was being looked at and stared at the ground in embarrassment.
“Well, well” smiled Mrs Bottomley “aren’t we the pretty sissy” and Simon could hear the younger lady snigger. He continued to look at the ground, aware that he was now furiously blushing.
“Excuse me!” boomed Mrs Stamford as she turned to Simon “we’ll have none of that false modesty here. You will thank Mrs Bottomley and give her a nice curtsey – unless you want a trip over my knee” and at that Simon could here the young lady snigger again.
Simon had never curtseyed before – he’d seen it on old films but didn’t know how too. He looked at Mrs Stamford’s face and muttered “Please . . Aunty. . I don’t know how too.”
Mrs Stamford could see the fear in Simon’s face and laughed. “Well Sissy, its time you learnt then!”
“Perhaps” suggested Mrs Bottomley “my daughter could teach Sissy?” and she looked at the younger lady. “Oh, I’d love too!” exclaimed the younger lady.
“Splendid idea” replied Mrs Bottomley. “Its Fiona, isn’t it?” she said looking at the younger lady.
“Yes it is. Just let me get a little teaching aide” and with that Fiona Bottomley disappeared back into the storeroom.
She emerged a few moments later with a thin bamboo stick about 3 foot long which she held in front of her in both hands as she strode purposely towards Simon.
In appearance she was nothing like her mother. She was slim and tall. With straight blond hair that reached to her shoulders. She did not look like she worked in a dressmakers – even if it was her mother’s. Instead she had the appearance of a young businesswoman. She was dressed in a crisp red and white candy striped bloused and straight cut black skirt that reached just below her knee. A pair of black high-heeled shoes accentuated her natural height.
“Now then” Fiona Bottomley addressed Simon “you are going to learn how to curtsey, which is the basis of Sissy deportment.”
Simon was acutely aware of the close proximity of the elegant young lady and could smell her fragrant perfume as she stood beside him. He still stared at the ground in embarrassed silence.
“First step” she announced, “is posture” and with that she put the cane under his chin and tapped it until Simon raised his head.
“Good, head up, but eyes down!” and Simon, fearful of the cane in her hand followed her directions.
“Now, shoulders back” and she used the cane as a pointer to sharply poke each of Simon’s shoulders.
“Good. Now take the hem of your skirt in between the thumb and forefinger of each hand.
Simon followed the instruction but absent-mindedly grabbed each edge with all the fingers on each hand.
“No! You oaf” he heard Miss Bottomley bark, before feeling the cane promptly strike first his left hand and then his right. Quickly he released the grip on his skirt and tried again this time using just his thumb and forefinger.
“Not a good start sissy!” smirked Fiona Bottomley. “Lets see how you do with the next stage” and she moved her position so that she was standing behind him.
“Now I want you to take your right foot and place it behind the left foot.” Simon followed the instructions wobbling slightly has he adopted this strange position.
“Steady” was all Miss Bottomley said.
Simon waited, holding his skirt as instructed, waiting for the next instruction.
“Ok Sissy, so now for the curtsey. I want you to bend your knees so that you dip down, and keep that pretty little head of yours straight whilst you do it.”
Slowly Simon bent his knees, feeling very unsteady on his feet as he did so. He had dropped perhaps a foot when Miss Bottomley announce “now rise again” and then “feet together”.
She returned so that she was standing in front of him and once again placed the point of the cane under Simon’s chin. “Well Sissy that was your first curtsey. It wasn’t very good, but practice makes perfect. So I want to see you do a dozen curtsies for me now. And I want each one to be smooth and elegant, or Mr Cane will come and visit the back of your thighs!” and she gave a little laugh. Then she stood so that she was to Simon’s side holding the cane ready.
“Now then, begin, and count each one out loud”
As Simon counted of the curtsies he’d been taught he was aware of the three ladies looking on a revealing in their humiliation of him. His legs were aching from the bending and adoption of the unusual stance but he was mindful of the cane carried by Miss Bottomley and knew that she would use it on him given a chance.
At last Simon counted off his 12th curtsey and stood, perspiring slightly, waiting for the next humiliation.
“Now” Miss Bottomley addressed him, “You will need to practice that frequently. I am sure that Mrs Stamford will ensure you do. If she is too busy to supervise I will be only too happy to visit with my friend Mr Cane to ensure you progress.” And with that she sniggered again
“Thank you Fiona, I might take you up on that,” replied Mrs Stamford. “Now then Sissy, thank Miss Fiona for teaching you to curtsey”
Simon needed no prompting – he was beginning to understand the rules – he took the hem of his skirt in his fingers, executed another curtsey, and expressed his thanks to Miss Bottomley.
“Well I’m sure you didn’t bring Sissy here for deportment lessons” laughed Mrs Bottomley. “What can we do for you?”
Mrs Stamford told Mrs Bottomley and Fiona about how she had caught Simon stealing the Wilson girls’ panties. She told them that the Wilson’s were on holiday but had been notified, and that they were due back in a few days. Simon, of course knew all this. He listened in horror, however, as he heard Mrs Stamford tell how she planned to take Simon to Church on Sunday and that in the afternoon the Wilson’s would be coming over for a tea party so that Simon could apologise to the family for violating their home, and their underwear.
“So I’d like something sweet and pretty for sissy to wear to church, and then something for the party – the girls have suggested that he should be put back into nappies, so maybe some baby clothes too?”
“Splendid” remarked Mrs Bottomley. “Fiona, perhaps you could fetch the Sewbaby and PrissyMiss pattern books. I think we may find what we are looking for there. Whilst we are ding so perhaps you could get Sissy undressed and start getting measurements.
For the next 10 minutes Mrs Bottomley and Mrs Stamford stood at a desk pouring over the various illustrations in the pattern books. Whilst they were doing so Fiona Bottomley undress Simon and led him, wearing only his underwear to a small stool standing in the centre of the room.
“Up we get” she commanded as Simon stepped onto the stool. “Now arms out straight and head up” as she busied herself with a tape measure noting various measurements.
Simon did not see what outfits had been ordered. He was only aware of the odd comment being made, such as “yes, that one, but can it be shorter?” and “Oh, now that would be embarrassing!”. He had little doubt that no consideration was being given to his modesty.
When the ladies were finished Simon was dressed again in the travesty of the sailor dress.
Mrs Bottomley looked up at Simon and smiled “We’ll have everything ready for Sunday, don’t worry poppet; We’ll make sure you turn heads and get noticed.”
“If you’d like, we can bring everything over on Friday for a final fitting, then if any alterations are needed we can do them next Saturday” enquired Fiona.
“Could you? Oh that would be wonderful” replied Mrs Stamford. “Thank the ladies sissy, and make sure you do it properly” she said turning to Simon.
Simon knew what was expected. He executed a quick curtsey and lisped “Thwank you Mith” to Fiona, before turning to Mrs Bottomley and repeating the exercise.
The Bottomleys laughed out load and Fiona said “See you at the weekend Sissy, and don’t forget to practice the curtsying”.
They were still laughing as Mrs Stamford led Simon back through the door and down the stairs to the street.
“Right then” she said “time to get you home, I think you could probably do with a little nap, couldn’t you? Home then ” and she led the way to the bus stop.