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Punishment 1 - by Debbie Johnson Chapter 1 - The blonde It had all happened the previous weekend when he had been out with a fellow college student, who had invited him to his brother's stag night. Not a hardened drinker, Jim had quickly gotten pissed and found himself separated from the others, in a large bar with what seemed like hundreds of strangers. He had intended to phone his live-in girlfriend of 1 year, Maria, and tell her he was drunk and would be heading home soon, but as he sat on the large leather couch at the back wall of the bar, he realised that he wouldn't be able to use his mobile phone due to the loudness of the the background music. He instead sat forward on the edge of the couch, with his hands on his forehead looking down at the floor. "Five minutes to steady myself then I'll be off," he thought to himself. After a couple of minutes, first one, then a second shiny black high- heeled shoe came into view. As he looked at the shoes, he figured they were what he had heard described as killer-heels. They were black patent leather, with what must have been 5 or 6 inch heels, with a single strap that ran across the top part of the foot, which itself fastened with a little silver buckle. "They are the type of shoes that I'd like to see Maria wear" Jim thought, before quickly dismissing the idea. He rued that although Maria was only 5 feet 4 inches in height, if she were to wear heels that high, she would end up around 8 inches taller than his own 5 foot 2 inch stature. As he took his head from his hands and started to look up, he slowly ran his eyes up the legs that were attached to the sexy shoes. In the brightly lit bar he could tell that the legs were encased in very sheer black tights. Up his eyes travelled, first past the slim shapely ankles, then past the smooth rounded knees and onwards past the firm-looking thighs, his eyes eventually settling on what for him was nirvana. The girl was wearing impossibly-tight, dark-blue, high-waisted, denim hotpants, which was his favourite turn- on. His eyes didn't get further that the women's waspie waist as they started to dart up and down from shoes to thighs, from thighs to ankles, from ankles to crotch. This went on for what seemed like minutes, but in reality was only seconds, before he heard a feminine cough, followed by, "Enjoying the view sweetheart?" Immediatley blushing scarlet, he bashfully looked up to look into the face of a gorgeous women of around 25 or so, heavily made-up, with blonde hair in a page-boy style with long fringe resting just below her concealed eyebrows. He quickly glanced at her not inconsiderable titties, which seemed to be trying to escape from a low-cut t-shirt which was obviously a couple of sizes too small. Jim was already overcome with a sense of lust, and, despite being in his drunken state, realised his cock had stiffened before hearing the further utterance, "Well......cat got your tonge sweetheart?............" When Jim awoke the next morning, thankfully in his own bed, he caught a whiff of perfume that he recognised as not being Maria's. Panicked, he quickly sat bolt-upright and looked at the space beside him on the bed, relieved to see that Maria was not there. He lay back on the bed and remembered that Maria was spending the night at the flat of her childhood friend, Karen, and would not be back until mid-afternoon. As Jim lay there, memories of the mystery blonde of the previous night began to creep into his mind. He rembered that she had sat beside him on the leather couch and had crossed those heavenly legs of hers at mid- thigh. She gently placed her hand on his own thigh and had asked if he was okay, which he re-assured her he was. They had then began chatting before they.... "Oh God!" said Jim out loud. "Christ! Please tell me we didn't! Please....Please...Please!" Slowy , Jim remembered he had talked and drank with the blonde for an hour or so, before she dragged him to the disabled toilet,which was adjacent to the leather couch. In there, the blonde had expertly given Jim what he could only describe as the best blow-job he had ever had in his, albeit brief, 19 years on this planet. "Oh Fuck!...What the fuck have I done...Fuck!...Fuck!...Maria will go apeshit if she finds out," Jim said aloud before bursting into tears. Chapter 2 - Explanation It had been a couple of days after the blow job incident when, overcome with guilt, Jim had blabbed to Maria about the the blonde and what they had done. This had caused a rant from Maria and her hasty exit from their flat. Now, on Saturday evening, Maria had returned to the flat. On seeing her, Jim had been relieved and confused in equal measures. Relieved that Maria had returned, but confused because, on the face of it, she no longer seemed angry, although her silence seemed to be at odds with that. When she eventually spoke, she calmly asked Jim to tell her why he would put at risk their relationship over a mere blow-job. As best he could, Jim then tried to explain that he didn't know what came over him and that if the blonde hadn't been dressed so sexily things wouldn't have happened as they did. Maria then got Jim to describe what the blonde had been wearing, in detail, from the shiny killer heels, to the sheer black tights, to the tiny blue hotpants. Maria made him describe the items several times, as Jim continually blamed the clothing on the reason for his being unfaithful. Maria took note that Jim didn't mention the top that the blonde had been wearing or what her face looked like. When Maria was satisfied with Jim's protestations, she proceeded to explain to Jim that she was prepared to forgive his weakness this one- time only and that she had not only been deeply hurt by his straying, but that she had felt a humiliation, the depths of which she had never felt before and that she would never want to feel again. To that end she had said that she wanted to punish Jim and had thought of a suitable one. Jim had told her that he would wholeheartedly accept any puishment that she saw fit. When Maria calmly explained what that punishment would be, Jim sat listening open-mouthed, before stuttering, "I'm sorry Maria..... wha...sorry what did you say?" "For the next 12 months, whenever you are at home, you will wear identical items of clothing to the ones that so turned you on that night," replied Maria. "You can't be serious," said Jim. "You want me to wear womens clothes? I'd die of shame." "You idiot, that's the idea," spat Maria. "I want you to feel the humiliation I felt. And as you protest that it was the sexy clothes that the blonde was wearing that started all of this, then for the next 12 months whenever you are at home and you look down at your body, you'll be reminded of your indiscretion and how humiliated you made me feel." Pausing for several seconds, she continued, "Well?........what's it to be? Yes and you stay here with me and we try to mend our relationship, or No, and you pack your bags immediately." It was a no-brainer to Jim. He loved Maria with all of his being and he didn't want to lose her. "Yes, I'll stay and try to make amends to you as best I can Maria. If that means some embarrassment for me, then so be it. I love you Maria," he said. "Okay then.... I'll get the ball rolling. Your puishment starts tomorrow," said Maria. As she rose and left the room, she thought to herselfas as a thin smile spread over her plump lips. "Love? Huh! That went out the window, or should I say into the disabled toilet the night you got your rocks off with that blonde whore. No.....once I've finished humiliating you, you're out on your arse you tiny skinny excuse for a man." Chapter 3 - Punishment begins The next evening at exactly 6.oopm Jim's face was so red that he thought he was going to explode with embarassment. This delighted Maria. Jim was sitting on the living-room settee. He was mortified. When Maria had suggested his form of punishment, and he had agreed to it, he had told himself that he could put up with anything to stay with Maria, and that anyway, it was just different types of material cut in a different style that he would have to wear, no problem he thought. But now, in the cold light of day, he wasn't so sure. Before having him change into "his new sexy clothes" as Maria described them, she had taken him into the shower and used a hair depilitory cream on his whole body from the neck down. He didn't have much hair anyway, but when he got out of the shower, he swore his body looked no older than a short plumpish 14 year old boys would. Maria had then handed him a pack of black 12-denier tights. As he stared open eyed at the packet, he saw that they were a make called Levante Class control tights and were Chestnut in colour. He then put them on under Maria's expert instruction. As she explained how to slide into the delicate creations without putting a ladder in them, she cooed to Jim that he would be an expert in putting on delicate tights in no time, causing him to give an involuntary shudder and sent his face a deeper red still; a reaction that was not lost on Maria. When "his" tights were fully on, Jim was amazed at how feminine they made his slender legs look. Jim was never a sporty type of person, and as a result had litte or no leg muscles. That fact now combined with the sheer tights, made his slim legs look not only womanly, but distinctly pretty. Maria then handed Jim "his" panties. These were not the usuall flimsy white cotton affairs that Maria normally wore. These were instead black satin and were definitely what he thought were in the "granny pants" variety. What Maria didn't tell Jim was that the panties were not panties, but a a high-waisted panty girdle, He was about to protest that he shouldn't have to wear panties because he didn't get to see the mystery blonde's panties (if she was wearing any that is), but he thought better of mentioning her again. He worked the panty girdle up his slim, hosiery-encased legs with difficulty, and said to Maria that they seemed too small. This earned the rebuke that he was talking nonsense, that they were a size 6, and that he needed them to be snug to hold in his tiny man-parts. The reference to tiny was like a barb to his pride, knowing now what he always feared, that his cock and balls were definitely smaller than average. But hearing it from his true-love smarted. He continued his struggle with his panty girdle, finally managing to squeeze into it. As he looked at his satin encased crotch he was amazed at how the girdle had crushed it almost entirely flat. He was further amazed when Maria slowly caressed the black satin and whispered, "Very nice.....very sexy." Jim immedietly felt his penis begin to stir, only for it to come to a halt in it's satin prison, causing him to visibly wince. His change of facial expression didn't escape Maria's eye and she smiled sweetly as she saw Jim's obvious discomfort. Maria then moved onto the next item of feminine finery. Jim was unable to identify what it was and when Maria saw Jim's puzzled expression she explained "This little creation is what is called a waist cincher. Although you were able to squeeze into size 6 panties they are elasticated and have some give in them. But your new hot pants don't have any elastication and their high-waited design doesn't have any give. Therefore we have to get your waist down to 24 inches from it's current 27 inches. This is also in black satin and is fastened using a hook and eye system. Now you'll probably find wearing a waist cinch uncomfortable for the first few weeks, but your body will soon adjust, and eventually wearing it will become just as an every day occurance to you as as wearing your panties will be. Now let's get it on you.." Jim gulped as Maria approached him and wrapped the black satin cinch around his waist. As she fastened it at his front, she urged him to suck in his stomach as far as possible. As Maria worked away, Jim felt his himself being squeezed increasingly tightly. He looked down just as Maria had finished fastening the last hook, and he marvelled at just how much the waist cinch had changed the look of his body. He saw that it stretched from a few inches below his nipples, and curved all the way past his now tiny waist, going down to just above his hips, flaring slightly as it did so. As Jim looked, he touched the cinch and as both hands ran up and down the silky material, he felt the boning which set his waist rigidly and wondered to himself how he would ever be able to bend over in it. As Maria stood and watched Jim, she smiled as she too saw the effect the cinch had on his body. She saw that it seemed to push up his excess body flesh into 2 small mounds around his chest area, and if she didn't know better, she would have sworn that Jim was starting to sprout a pair of delicious little titties. She saw that the cinch had reshaped Jim's body so effectively, that he had the beginnings of an hourglass figure. After giving Jim a couple of minutes to get used to his newly constricted waist, Maria handed him "his" high-waisted hot-pants, which were a dark shade of blue denim with an inch of turn-ups and looked impossibly small for him. He then felt inwardly grateful to Maria for coming up with the idea of the waist cinch, which should enable him to squeeze into them. And squeeze into them he did, and not without some considerable effort. He had joked in the past about girls wearing jeans so tight that they must have jumped off the wardrobe into them to get them on. He worried he might have to do that himself, but in the end he managed to get his hot-pants buttoned and zipped up. He marvelled at how his hot-pants seemed to make his crotch even flatter if at all possible, and he couldn't help but admire the contrast they made against the colour of his sheer tights. Maria then told him to sit and she would put "his" heels on to his feet. He sat as instructed as he watched Maria fish into the shoe box lying beside her on the floor. He wasn't quite prepared by what he saw. Maria was holding a pair of black, patent, leather court shoes, with yellow soles. As he stared at them thinking how the hell I'm I going to be able to walk in those things, he thought Maria must have read his mind as she said "Now these have a 5-inch stilleto heel and no platform in the sole, so you'll need a lot of practice walking in them. But don't worry, you will get loads of practice, and will soon be able to move with the grace of a runway model in no time." Jim shuddered again as he listened to Maria, who continued "Now, I know you find shoes like these an incredible turn-on, so to remind you that wearing them is actually a punishment, I got you them in a smaller size. So these are a size 5 and not your usual size 6, so they will pinch a bit every time you wear them. "What?....no...I don't find the shoes a turn-on," protested Jim. "It's just that womens feet look much sexier when they wear high-heels." "Oh! Silly me," said Maria. "Just a slip of the tongue. Let's just ease your little tootsies into these bad boys and see if they make your feet look sexier" Maria took first Jim's left foot and then his right, and as he pointed his lycra encased toes, he slipped and squeezed them into each of the glossy high heeled creations, feeling his feet becoming re-shaped into the classic feminine arch. "There!" she said. "All dressed now. And you're right about heels making womens feet sexier. Yours look fabulous in those." Realising that Maria had just addressed his feet as womens feet, Jim protested he wasn't a woman but a man instead. "Oh stop fussing," said Maria. "Jeez...a bit of make-up and a padded bra and we could send you off to work in Hooters....your legs look that hot. Anyway, lets get you standing in these for the first time." Jim was going to complain about Maria's comments, but looking at his lower body, he knew that from below the chest he unmistakenly looked like a woman, and inwardly he cursed his pathetic lack of physique. Maria then grabbed his arms and hauled him to his feet, and as he stood upright he nearly fell forwards as he shared the experience all girls have, when they try to stand up for the first time in a pair of high heels. As he did so, he felt as if his whole weight was bearing down on his toes and the balls of his feet and he was clinging to Maria as if his life depended on it. "Now," Maria said, "your 12 months punishment starts now, so lets get you some practice walking in your high heels." Maria then subjected Jim to an hour of hell. She made him walk up and down their 40 foot long hall, insisting that the only way he would get accustomed to his new high heels, would be for him to practice walking in them. By the time she had summoned him into the living room at the end of the hour, she made him parade up and down the length of it a few times, and said that he had made some improvement, but that he still had some way to go if he wanted to please her. Jim did indeed want to please Maria, but he thought he was already doing a good job in manouvering about in high heels, considering that he had never worn shoes with so much as an inch heel before, never mind the towering 5-inch stillettos he was now wearing. He was going to comment to Maria that his feet were burning from pain, given that the shoes were a size too small for him, but then remembered that Maria had said that the high heels were not for his enjoyment, but for his punishment instead. Those words were now being hammered home. "Come sweetie,....come sit on the couch beside me," commanded Maria, as she patted the cushion of the settee. Jim made his way over to the settee, taking small steps. Maria watched him intently as she thought to herself "Hmm....short mincing steps definitly suit his new appearance. And my god does the little twerp have some seriously gorgeous long pins on him. He might be a shortarse, but in that outfit he seems to be all legs." Maria then squeezed her thighs together as she felt the first delicious tingle of arousal. "Jeez," she thought, "this is starting to turn me on......what a pleasant bonus." She was knocked out of her thoughts as Jim plonked himself rather ungainly next to her on the settee. A frown crossed her face as she exclaimed, as much to herself as to Jim "No No!...that will never do. That was far too ungainly for someone with such pretty legs!" Jim looked at Maria shocked. When he had first put on his new clothes, he had realised that his legs were too pretty for what a normal man's should be, but he was still disturbed to hear Maria share his own thoughts, and vowed to himself, that he must join a gym as soon as possible to get some muscle onto his legs. "Now, I know that this whole change of clothes thing is designed to punish you sweetie, but there is no reason for you to develop any slovenly behaviours is there? Maria asked Jim. Jim was momentarily confused by this question. "What does she mean by slovenly behaviours?" he thought to himself. "I've not done anything differently in the way I sat down." Maria continued, "Right. We will start off as we mean to go on. I have an idea on what we can do to improve your walk, but before that, we'll have to do some work on your deportment and how you sit and rise from a chair." For the next hour Maria coached Jim on the correct way to rise from the settee, making him walk to the end of the room, and swivel...not turn as a normal person would do, no, swivel on the ball of one foot to face the opposite way... before gliding to the settee and delicately turning his back to it, before softly setting his arse on it and crossing his legs at mid thigh. This went on for ages, as Maria constantly told him what he was doing wrong, and correcting him on what to do properly. The only interruption to her verbal barrage was when she went into the kitchen to make an phone call to her friend Karen. Jim was over 2 hours into his new routine, when Maria allowed him to finally rest onto the settee and watch some telly with her. He sat there with her for 3 hours prior to going to bed, without getting up once, giving his feet some much needed relief. Every now and again he would uncross his legs and cross them again with the other leg on top, much as he had seen countless women do, and would hear the whispering zip of the lycra as his legs rubbed against each other each time he did so. It was partly a subconcious movement, but also was done to get more comfortable as he wasn't used to sitting with his legs crossed. He would also take occassional glances at his legs, from the towering glossy heels, all the way up the sheer black tights to the impossibly tight hot pants. As he did so, he began to realise that Maria had managed to do what she had intended, in that his legs were dressed so sexily, that they looked so much like the mystery blonde's did that fateful night. He hated that he thought of his own legs as being feminine and sexy, and in a corner of his mind he was worried that he might be liking his punishment even just a little. As Jim sat there with his mind confused, he didn't notice a smiling Maria watching him from the corner of her eyes. Maria was smiling not only because she had discovered just how submissive her wimpy boyfriend was, but also just how wet this whole experience had made her panties. She vowed to herself to thank her friend Karen for coming up with the idea. When Jim went to bed that night, he thought that he would be allowed to take off all his new clothes, but Maria instead insisted that he wore his panty girdle and waist cinch to bed, so that his body would become accustomed to them more quickly, a thought which made Jim inwardly groan. That night as he tried to get some sleep, his feet and calves were aching from the evenings onslaught and with dread, he thought of the year of punishment ahead. As he drifted off, he didn't realise that one of his thumbs was absent mindedly stroking the taut black satin prison that rigidly gripped his crotch Chapter 4 - New routine It was now Monday at 4.oopm. Jim had been home from college for nearly 15 minutes, and he had spent those minutes in the main bedroom debating with himself whether he should change into his sexy clothes. He thought of them as his sexy clothes, not because he thought they were sexy, but instead because Maria had insisted that whenever he mentioned them or even thought of them, then that was how he was to describe them. When he opened his underwear drawer and looked in, he was dismayed at how busy Maria had been after he had gone to college that morning. On the right side of the drawer, he saw that his old boxers had gone and were replaced by 10 packets of lingerie. Or to be more precise 10 packets of the same satin high waisted panty girdle that he had worn the previous night, all in the same size 6, and saw that 3 pairs were black in colour, 1 pair in lemon, 2 pairs in pink, 2 pairs in red and 2 pairs in white. His heart sank when he realised that as Maria had gotten rid of his old underwear, he would need to wear his new lingerie at all times, and not just during his punishment time when he was at home. He then looked over to the left hand side of his drawer. Sitting there were 5 satin waist cinchs, in colours black, red, pink, lemon and white and he briefly wondered to himself how much this punishment was costing Maria in financial terms. He was not at all surprised to see that his socks had also vanished in the same manner as his old underwear. In their place now sat a dozen pairs of tights, of varying make. He glanced through the packets and recognised the name Levante on several packets, realising they were all 12 denier sheer black tights similar to those he had worn the previous evening. Some of the names were unfamiliar to him and he read them out loud, "Pretty Polly...... Aristoc...... Jonathon Aston......Charnos......Cette." The last packets lookeds different and as he picked them up saw that they were called Pretty Polly 40 denier black opaque tights, and that they were actually 2 separate twin packs, making 4 pairs of black opaques. As he rubbed the smooth material of the opaques, he realised that they were slightly thicker than his sheer tights, and made the connection that as they were thicker, they must be more practical than his delicate sheers, and that Maria must have her reasons for buying them for him. Jim then closed what was now his lingerie drawer and opened the one below. He wasn't surprised to see that all of his normal baggy shorts had been replaced with 6 new pairs of high-waisted hot pants. 3 of the pairs were blue denim, 1 being the hot pants he wore the previous evening, 1 were very pale blue denim with turn-ups, and 1 were again very pale blue denim, but with white frayed edges, almost half an inch long. The remaining 3 pairs of hot pants were in the colours red, pink, and lemon, and all in cotton. All in a size 6 and high waisted. Jim's mouth was agape when the full extent of his punishment began to sink in. As he realised that Maria intended to be true to her word and make Jim dress in his sexy new clothes for the next year, he felt his eyes begin to tear up, before catching himself, and saying out loud, "Come on now Jim....get a grip of yourself. You can do this, and at the end of the year things will go back to normal and you'll still have Maria." Then, in an almost out of body experience, Jim reached into the drawer and pulled out the light blue denim hot pants with the frayed edges. He then went into his lingerie drawer and pulled out a pair of12 denier Pretty Polly sheer black tights, a red panty girdle, and a red waist cinch. He placed them all on the bed before going over to open his wardrobe door. He was relieved to see that he still only owned the one pair of high heels as he bent down to pick up the glossy black stillettos and took them over to the bed. Chapter 5 - Going solo Jim took a shower before changing into his sexy clothes, as per Maria's instructions. While in the shower, he marvelled at the job the depilitary cream had done on him the previous evening. The sensations he experienced while using the shower cream on his skin (another instruction from Maria....no more soap in the shower, only her moisturising shower cream) was another new one to him. He couldn't believe how silky his skin felt, and when he closed his eyes it was almost as if he was caressing the skin of a woman. He was so lost in the sensation that he almost didn't notice the raging 4 inch hard-on he was now sporting. When he eventually began to caress his penis with hands frothing with shower cream he immediately erupted in a shattering orgasm. After leaning against the tiled wall trying to get his breath back, he thought "there may be some benefits to this new arrangement after all." After towelling himself dry..."patting your skin sweetie, not rubbing it."..following Maria's instructions from the previous night, he spent a few minutes rubbing some of Maria's moisturising cream all over his body (another instruction), then walked into the bedroom. Jim looked down at the assortment of clothes on the bed and let out a long sigh. "Day 2 of punishment, only 363 days to go" he thought to himself. Maria was due home shortly and she had left strict instructions that he must always be dressed in his sexy clothes before she gets home. He sat on the edge of the bed, opened up the packet of tights and gently slid them out. After taking the tights from the cellophane inner packet he gently let them fall open to their full length. As he held them up against the light of the window, he could see just how delicate the material actually was. He was immediately fearful that he would put a snag in them when he attempted to put them on, as Maria had given him a warning that by doing so, it would be an infraction that would earn him a yet to be determined further punishment. He looked at his fingernails for any signs of nicks that may catch on his tights, and realised that sooner or later, he would have to take Maria up on her offer of teaching him how to care for his nails. Jim slowly and deliberately rolled up the left leg of the sheer tights in the doughnut fashion Maria had showed him yesterday. He then pointed his left toe and slowly ran the hosiery up as far as his knee. He then repeated the process with the right leg, this time taking the hosiery up as far as mid thigh, before moving back to the left leg and pulling up the tights to the top of his thigh. He then finished putting the tights on by pulling the heavily elasticated control top fully up to his waist. Once he had the tights fully on he stared at the crushing effect the control top had on his crotch, wondering how a penis which was at full mast only minutes earlier could now have seemed to have vanished so completely. Jim then took the red panty girdle out of its packet and stepped into the legs one foot in turn. He slowly worked the girdle up his legs and began to struggle once more as he reached the area of his upper thighs. Carefully so as not to damage his tights, he slowly inched the girdle into place around his crotch and tummy, in a ritual which, although new to him now, would soon become an everyday occurrance. Once Jim had his panty girdle fully on, he glanced over at his reflection in the full length mirror. He was immediately captivated by the contrast of his sheer black tights against the vibrant red of his satin panty girdle, and, for some reason unknow to him, suddenly thought he looked very "christmassy." He stared at his reflection for only a few minutes, before realising that he actually liked the look of the combination of colours and materials encasing his lower body, before cursing that it was himself that was being forced to wear the clothes, and wished he could get to see Maria wearing identical delicates. Jim was oblivious to the fact that the image of his slim feminine legs encased in the sheer black tights, and his smooth girly crotch enveloped in rich red satin, was beginning to register in his mind and associate the clothes with sexiness and in turn arousal. If he hadn't came in the shower a few minutes earlier, there would have been a distinct possibility that his small penis might have twitched into life. As it was, it was now firmly set like concrete within its satin confinement, with no room for growth. Jim then spent the next 10 minutes getting into his waist cinch. It was obvious to him that Maria had managed the hook and eye fastenings much better than he was able to, but he was hopeful that he would be able to get into his waist cinches much quicker in the near future, and indeed, get dressed in all his new sexy clothes much quicker for that matter. It didn't occur to Jim that having such a thought should be unusual for a normal, hetrosexual, young man, but then again, he didn't realise that the design of Maria's punishment was also starting to have a subliminal effect on the design of Jim's mind also. Next, Jim squeezed into his hotpants, and once on, he subconsciously noticed that their light blue colour contrasted pleasantly with the colour of his tights. Next, Jim pulled on one of his own slim-fit t-shirts before attempting to tackle getting into his high heels. Maria had told him the night before that the best way for him to slip his stillettos on unaided, would be for him to do it standing up. So holding onto the bedside cabinet, he pointed the toe of his left foot and eased it into the shiny shoe. Although the court shoes were a size too small for Jim, he noticed that the slippery material of his tights seemed to make his foot more dainty and allowed it to slide effortlessly into the shoe and before he knew it, it was fully on. Jim then slid his right foot into his other high heeled shoe. He stood with posture fully upright, as his waist cinch would allow for no slouching, before taking his supporting hand away from the bedside cabinet. Jim had almost expected to fall over once he did so, but was pleasantly surprised that he was able to easily keep his balance in the high heels, probably due to last nights practice. "This might not be as hard as I thought it would be" he smiled to himself, while looking at the severe arch his feet now seemed set in, without once realising that the mere act of putting on a pair of killer heels had caused him to feel more subconscious pleasure. Chapter 6 - Karen When Maria had first told Karen about Jim's infidelity, Karen had been a great comfort to her, and she had let Maria stay at her house for a night while she had gotten her head together. In truth however, it had been more than just comfort that Karen had wanted to provide. Karen had a secret crush on Maria, which may have been as a result of their "experimental days" 10 years ago when they were both at school together, aged just 14. As both of the young girls sexuality began to awaken, they did what many girl friends did, by learning about their bodies during "sleepovers." During the sleepovers, they indulged in hours of illicit sexual passion together, in which the most common theme was performing oral sex on each other. Their illicit affair continued for a year, until Maria decided that it was time for boys, and insisted that it was time they each found themselves a boyfriend. Karen never told Maria how she felt during and after their schoolgirl affair, because she didn't want to lose Maria's friendship, but she was devastated that Maria had decided to end the affair,and she rather foolishly thought they would be lovers forever. However, Karen had vowed at that young age, that she would be the best friend that Maria could ever hope for, and carried the faint hope that maybe, one day, she might, just might, become her lover once more. On meeting him, Karen had an immediate dislike for Jim, a dislike which had slowly turned to hate, although she hid her feelings well from both him and Maria. She particulary hated the fact that at 5 feet 2 inches tall and weighing less than 8 stone, Jim was shorther and lighter than she was at 5 foot 7 and 10 stone in weight. She couldn't therefore understand why, when Maria had decided years earlier that she was into men, that she had eventually opted for a creature with such an unmanly physique. Ironically however, it was Jim's physique that had given Karen the idea on how Maria could exact her punishment, and when she explained her idea, Maria was delighted and they spent a whole night plotting, discussing and refining the idea in minute detail. Chapter 7 - Expectation As Maria arrived home from work and stepped through the front door of her flat, she could feel her heart racing slightly and felt somewhat nervous at what she would find. She had been distracted most of the day at work. The cause of her distraction had been the images that kept creeping into her mind. Those images had been of Jim's pretty legs sheathed in black lycra, with his feet impossibly arched in sexy stillettos, which had been reality just the previous night. All day she couldn't wait to get home, hoping to see Jim further entrenched in his punishment, mincing around the flat in his hose, hotpants and heels. Maria quietly closed the front door, took off her coat, draping it over a hallway chair, and silently slipped out of her own 3 inch high heels. In her stocking feet, she tiptoed over to the kitchen door, stopped in the doorway, and smiled as she saw Jim standing over the stove as he slowly stirred a bowl of pasta. Maria assumed it was Jim, as there would be no reason for anyone else to be in the flat. She was sure, however, that any stranger who might have been standing in her place would have had considerable difficulty recognising that it was a male standing at the stove, never mind it actually being Jim. Maria stared at Jim for several minutes without making a sound. Her eyes were first drawn to his stunning legs. If Maria had had any initial doubts about what she intended to do to Jim, the doubts were dispelled there and then. As her eyes slowly made their way up and down Jim's shapely legs, Maria realised that there was no way possible that they could ever be mistaken for male legs. They tapered from his slightly chubby upper thighs, all the way down to slim ankles, and the sheerness of his tights showed that Jim's legs were evidently hairless, and appeared to be blemish free. Maria also noticed that the length of Jim's legs seemed out of proportion to the rest of his body, in thatfrom toes to waist, they seemed to take up almost 2 thirds of his total body length. Maria then looked at Jim's ever so tight hotpants that seemed to shape his bum and hips into an almost perfectly smoothly rounded bubble, and again, Maria thought that it would be difficult to mistake such a bum as being male. Maria's eyes then settled on Jim's feet which seemed to be coping easily with the 5-inch stillettos they were slipped into, although, as he did have one leg perfectly straight, and the other slightly crooked at the knee, she realised that Jim must be experiencing the discomfort that comes whenever a girl is standing and wearing heels for any length of time, and by crooking his knee, he was taking the weight partly off one high-heeled foot. Maria then looked at Jim's upper body, as if almost for the first time. She noticed that Jim's back and shoulders were slim with little or no muscle mass, and his arms were built in the same slender proportions as his pretty legs, and wondered to herself why she had never noticed that before. Finally she noticed that Jim's hair was getting pretty long. It was now well down his neck and was probably only a few weeks away from reaching his narrow shoulders. As Maria sood there quietly paused in her thoughts, with ever-dampening panties, she realised that she was definitely doing the right thing , and that with Karen's help she would get the results she desired. Conversation during dinner was fairly muted, with Jim unsure of what mood Maria was in. Eventually the main topic was broached when Maria said "So then sweetie, how do your feet feel now that you've worn heels for a second time?" Jim wasn't overly keen to discuss the subject, but as there didn't seem to be any way to avoid it, offered "Not too bad considering. I found it easy to slip them on by doing it standing up as you suggested, and all that practise in walking in them last night seems to have paid off, as I was able to manage in them quite well. They do still seem tight, but as you explained last night, that is to add to my punishment, so I won't complain about that. "Yes," said Maria. "You do seem to be getting the hang of them. Have you ever worn high heels before this week?" "Eh?!" spluttered Jim. "Certainly not! I'm not some sort of pervert tranny you know. This is all your idea if you remember." "Okay, Okay," smiled Maria. "Don't get your....ahem...PANTIES...in a twist sweetie. Anyway, I take it you had a look at your new wardrobe when you were getting dressed?" "Yes," groaned Jim in reply. "Well it's not fully stocked as yet" said Maria as Jim looked up, puzzled, from his meal at her. "No, one pair of high heels will never be enough to get you through the year. You'll need another two or three pairs...at least. Though this time I'll let you pick them out so that you at least get stilettos that you like. Talking of which,do you like how your first pair of heels look?" Jim was unsure of how he should answer that question. What was Maria really asking him? Was she trying to trick him or something? And why did she think he would be interested in shopping for high heels? "Well?" continued Maria impatiently. "Do you like how your heels look?" "Well....obviously....high heels are sexy," stammered Jim. "....but really only when they are being worn by women. I'd love to see you wear these shoes sometime. But I don't think they look sexy on my feet." "Why not?" asked Maria. "There's nothing fundamentally different about mens and womens feet, other than mens feet are normally bigger than womens feet. But that's certainly not the case with you. Not many men would be able to wear high heels in a size 5, but you are managing it quite easily. Certainly, looking at your feet, not many people would dream of even mistaking them for mens feet. Your shoes are classic, elegant high heels and I think they, together with your sheer tights, make your feet and legs look ever so pretty." As she had spoke, Jim's face had gotten steadily redder, and as each word dripped salaciously from her lips, Maria felt her panties dampen further. "But.....but....I don't want to think of my feet as being sexy or even pretty. It's not right for a man to think that way. Not unless he is some transvestite or something," replied Jim. "So," said Maria, "let me get this straight. What you are saying is that if I was wearing your tights and your stilletos, you would think that my feet and legs were sexy. But because you are wearing them you don't? Come on now sweetie. I don't think you are being truly honest here are you? I mean look at you for Christ's sake. Whether you want to admit it or not, your legs are a total knockout. So much so that if you were actually a women, you could easily be making a living modelling hosiery. So, are you going to be honest with me? After you got dressed in your sexy new clothes, did you not sneak a look in the mirror and liked what you saw in it? Don't lie to me now, because if you do I'll know and you'll be heading for extra punishments". Maria was eying Jim's facial expression intently. He was blushing as red as anyone she had ever seen before, and he almost looked as though he was tearing up just a little. She loved this new found power she had over Jim and this delight was transferring itself to her panties which were now thoroughly wet. "Well," said Jim, "I did look in the mirror. And if I'm being honest, I did think the contrast between the red of the panties and the colour of the tights did look somehow christmassy, so I suppose I did sort of like how they looked. And when I was fully dressed I did think the shoes looked good. But.... I mean....I would challenge anyone not to think that. It's not possible." Maria couldn't believe it. Her pantied and corsetted boyfriend had almost just confessed to liking wearing women's clothes. Was he secretly a closet transvestite she wondered to herself. How far could she possibly take him down this path of feminity she had started him on? "Oh my!" said Maria. "Only a minute ago you said only a transvestite would like how his feet and legs looked while wearing tights and high heels. And her now you've just admitted that you liked how you looked when you peeked in the mirror. So what does that make you then? A pervert? A transvestite? Eh? are you a little sissy? Did you get hard when you looked in the mirror? She was on the verge of coming, and knew she had to rein herself in a bit. This gave Jim a chance to speak and he spluttered, "God no! I'm none of those things. You are trying to twist my words. And no, I didn't get hard. I couldn't have , as I had just came in the shower, and you know I need at least thirty minutes to get hard again after coming" Jim caught himself too late and realised that what he had offered as a defence was not only, not that, but he had confessed to pleasuring himself in Maria's absence, which he knew she felt was as bad as infidelity. He sat motionless and stared at Maria as he saw her expression turn from amusement to anger. "You did fucking what?!" she screamed at Jim. "You've been playing with yourself in the shower....after I said you were never to do it again after the last time I caught you? What was it? Was it the thought that you were about to get dressed all girlie that made you hard? Was it? Eh sissyboy? Was it the thought of slipping into delicate tights and shiny lingerie? Was it the thought of mincing about in high heels and hotpants while you pretending to be a little pretty housewife, making dinner and getting ready for her big strong husband to come home and give her a big kiss? Eh? is that it? Should I get you some bras and blouses and put make-up on you? Maybe even get you some pretty dresses? Eh? is that what we should do .....TRANNY!?" Jim was now sobbing. All through Maria's tirade he had continued to protest no at every question. But he was scared. He was scared in case he did like how his legs looked encased in sheer black lycra, and how sexy his shoes were. But he wasn't a transvestite. He knew that. He had never harboured any notions of trying on women's clothes in the past. Indeed he thought any tranny he had ever seen, which was not many, looked plainly ridiculous. Maria sat looking at Jim, who was now crying like a little girl. She watched as he shot out of his seat and ran......yes ran!....from the kitchen into the toilet. She was very surprised at the speed Jim ran from the room. Christ, she coudn't even run in 3 inch heels, yet alone the 5 inch skyscrapers Jim was wearing. She thought to herself that he must have worn high heels in the past to be able to maneouvre that quickly in them. All the while she was thinking this, she had been rubbing her clit furiously through her knickers, and it was no surprise to her that she erupted with a thundering climax that was easily the best she had ever had. "Fuck me!" she exclaimed a little to loudly for her own liking, as she sat there in a post-climatic glow. Five minutes after her orgasm, Maria got up from her seat and made her way over to the toilet door. She Placed her ear against it to try to hear if Jim was still crying, but could only hear silence. She tried the handle of the door, but it was locked, before saying "Sweetie?.... Sweetie?....Are you alright in there?" "Leave me alone....I don't want to talk to you," came Jim's reply from behind the door. This exchange was more or less repeated for about 5 minutes, before Maria was able to coax Jim to open the toilet door. When he did, Maria immediately noticed that Jim had taken off his stilletos and was preparing to leave the toilet in his stockinged feet. A frown crossed Maria's brow as she gently placed a hand against Jim's chest to bar his exit from the toilet and whispered to him "Now sweetie....no walking about in your stockinged feet for you for the next year....it's high heels or the door for you and you know that." Jim looked up into Maria's eyes, with a yearning for pity that was evidently not there, and almost pleaded with her to stop this foolishness, before realising her stern expression was a signal that Maria was not for changing her mind. Dejectedly he walked back into the toilet and again slipped into his stilletos. As he did so, Maria watched silently and incrediblly felt a fresh tingle of arousal in her loins. When Jim returned to Maria, she silently took his hand, led him to the living room settee, where they both sat, crossed legged, and silently watched some television, before later going to bed and to sleep. Shopping for Shoes Jim was miserable the whole of the next day at college. He wasn't able to concentrate at all on his coursework as he fretted endlessly about his exchange with Maria the previous evening. He also was definitely not looking forward to dressing in his sexy clothes and wondered to himself whether he would be able to cope with a further 362 days of punishment. However, after getting home and he had showered, Jim reluctantly went about getting ready to get dressed in his new sexy clothes. This time he opted with pairing his lemon panty girdle with his lemon waist cinch, and then selected his lemon hot pants. Jim stopped briefly and thought to himself why he had decided on these colours, before shaking his head dismissively and rationalising with himself that he will have to wear everything at some point. After he had slipped into his sheer tights and squeezed into his panty girdle, Jim couldn't help himself by sneaking a quick look in the mirror. Again, as happened yesterday, he was captivated by the pretty contrast of his sheer black tights against the vibrance of the shiny yellow satin of his panty girdle. He hated that he liked how they looked on his slender frame, and actully felt tears forming in his eyes. He tore his gaze from his reflection and spent the next 5 minutes putting on his waist cinch, hotpants and slim fit t- shirt. He silently then went over to his wardrobe to get his high heels, and as he did so, he failed to notice that his walk had already changed to short mincing steps with a roll to his hips, almost as if he were already wearing his stilletos. It was almost as if Jim's mind had undergone a subtle shift as it now seemed to associate wearing sexy clothes with his new walk. Once at the wardrobe, Jim took out his high heels, placed them onto the floor and slipped them on. As he did so he barely held on to the wardrobe to steady his balance, such was his confidence in stepping into skyscraper heels even after just 3 days. Again he gazed at his reflection in the mirror he couldn't help but curse the fact that he liked how sexy he now looked. He then started to feel the first tinglings of arousal and said out loud "No...please no....don't let me get turned on by any of this!" Jim then looked down at his feet and was almost transfixed as he stared at his glossy stilletos in the mirror, and almost shocked himself by thinking that yellow patent stilletos would probably look better with his outfit. He was not only shocked that he would consider wearing yellow high heels, but also that he considered what he was wearing was an outfit, rather than just clothes. Bemused by his own thoughts, Jim went to prepare dinner and awaited Maria coming home from work. Dinner was eaten silently by both Jim and Maria, and after it was over and Jim had washed and dried the dishes, he teetered into the living room, where he saw Maria was busy on the laptop. Maria breached the silence by summoning Jim over to sit with her on the couch. Jim walked over to the couch and was extra careful to walk just as Maria demanded him to, with short steps, and with slightly more roll to his hips than usual just to be sure. After he had gracefully settled down on the couch and he had elegantly crossed his lycra encased legs at mid-thigh, hearing the now familiar whispering zip of the tight lycra, he was surprised when Maria gently took both his hands in hers. As she looked into his eyes, Maria said one word. "Sorry." That was all it took for Jim to start crying. Jim didn't really know why he was crying, but when his tears had subsided after a few minutes, Maria continued "I'm sorry for what I said to you last night Jim. I know your not a transvestite or a pervert or anything, but I guess that I just found it hard to come home from work to find by boyfriend not only dressed so prettily, but also how sexy he managed to look too. Now I know that your punishment was my idea and that I will have to endure it just as much as you, but I will try to be strong and accept that you now dress as a woman at home. Hopefully the tears can now end and we can get on with the rest of your punishment, and, before we know it, it will have ended and things will be back to normal" Maria looked intently at Jim to see if there was any trace of realisation that she had just lied throught her teeth, but was happy to see only bewilderment in Jim's expression. Jim sat quietly for a few seconds, unsure whether Maria had finished speaking, and also because he was unsure what to say. He was terrified that earlier when he looked at his reflection in the mirror he felt pleasure and even slight arousal, at how sexily he was dressed. But he couldn't admit that to Maria could he? She would propably throw him out of the flat. No...he couldn't and wouldn't. Also he didn't realise that him wearing sexy clothes would give Maria cause to be further upset. He had been so wrapped up in his own self-pity that he hadn't thought what effect this would have on her. No he would have to be stronger for her to enable both of them get through this. "I'm sorry too Maria," Jim said, "this is all basically my fault, and I'll do anything that helps us get through the next year or so. Just you tell me what you want me to do and I'll do it." "Well I have a few ideas in mind," said Maria "but for now, we have to get you more shoes." Jim nodded and said okay, but a brief flicker of an image of a pair of yellow patent heels flashed across his mind and thought to himself whether he would have to stick to black shoes or different colours. His own question was answered when Maria placed the laptop on his lycra- encased thighs and said, "Time to get busy. What I want you to buy tonight is 3 more pairs of shoes. The stipulations are that they must all be black patent leather, with slim stilleto heels. The heels must be a minumum of 5 inches high, but you can go higher if you want" Jim gulped as he thought about trying to wear higher heels than the 5-inch high ankle breakers that were already on his feet. Maria continued "Now you are allowed to get shoes with a small platform sole, but the thickness is to be no greater than 1 inch. And, if you get shoes with a platform sole, the heels must be at least 6 inches, so that the difference between sole thickness and heel height is always at least 5 inches. I want you to get different styles of shoes. You already own a pair of elegant court heels Jim, so you don't need to get another pair of those. The styles you can choose from are the likes of t-bars, simple one bar, to 2, 3 or even 4 bar shoes, and these can be open waisted or closed waist. You also have slingbacks, but make sure they have a closed toe. I also want you to consider a pair of knee boots, again with the required heel height. And no sandals. Now I know that you don't have great experience with women's shoes yet, but you can spend the next couple of hours browsing through the available styles. As you do that, make a short list of 5 pairs, and I'll help you whittle it down to 3 to buy. Got that, good," (as Jim nodded) "and remember, this is a punishment, so you take a size 5 shoe now." Jim did as he was instructed and spent the next 2 hours shopping for high heels. As he did so he was amazed at the huge range of styles of shoes that women could choose from. He always liked to see women wear high heels, and he found his task of shopping for stilletos surprisingly pleasant. So much so, that when Maria told him his 2 hours were up, he was surprised at how quickly they had flew by. Jim then spent the next 10 minutes showing Maria his selections. He had picked a pair of boots first. He had to explain to Maria that he thought all the patent boots had looked cheap and whorish, but that he had found a pair of black leather, fitted, zip-up, knee boots, which although had a 1 inch, mini- platform sole, had the required 6 inch stilleto heel. Although not patent, the soft looking leather did have a high shine to them, and he hoped they would be okay. Maria was immediately impressed by Jim's taste, because not only did the boots look sexy, but also classy, and were a pair that she herself would have no trouble wearing to the office. A strange thought then occurred to her, that as Jim's feminine wardrobe started to grow, she would be able to borrow some of his clothes. Maria immediatly agreed to Jim's boots selection and told him to go ahead and buy them. The next pair of shoes Jim picked were a pair of black patent, open-waisted, t-bar stilletos, with a 5 and a half inch heel height and no platform in the sole. She again was impressed by Jim's selection and told him to click buy. The next pair of heels that Jim had chosen, were a pair of black patent shoes with a six inch stilleto heel and a 1 inch platform sole. These were bar shoes, with three straps running across the top part of the foot, which attached to silver buckles. Again, Maria was impressed that Jim had excellent taste in womens shoes and instructed him to buy them. As he did so, Maria also realised that Jim's 3rd selection were not all that different from those worn by the tramp who had sucked him off and a small smile flickered across her face, as she gave Jim her bank card and told him to close the on-line transactions. When Jim had finished buying his new high heels, he set the laptop aside and settleed down to watch TV with Maria. As he sat there silently, he thought to himself that he wouldn't mind whiling more time away shoe shopping, and began to understand why women loved the almost therapeutic nature of the task. Shoe delivery The following morning after showering, Jim started to get dressed. He selected his panty girdle for the day, but when he reached for socks realised that he no longer had any. He looked over at Maria and asked her, "I don't have any socks left Maria, what should I do?" Maria repled with, "That's why I got you some thicker opaque tights sweetie. You can wear those under your trousers, which are long enough that no-one will see your tights. But even if someone does get a glimpse that you are wearing tights, unless they look really closely, they will think that you are just wearing thin black socks." Jim didn't feel at all comfortable with the thought of not only having to wear his panty girdle to college, but also tights, but he knew better than to start another argument with Maria. Instead he simply reached into his drawer and took out a twin packet of the Pretty Polly 40 denier tights. As he seperated one pair from the other and let them fall open to thier full length, he could see that they were considerably thicker than his sheer tights. Nonetheless, he was careful as he slipped the tights up his legs and once fully on could see that around his ankles and lower legs, the tights did appear to have a similar appearance to thin socks, but around his thighs, where the lycra was stretched more, it was thin enough that he could make out some of his skin. Did he imagine it, or did his cock just twitch a little!? "My god!" he thought, "what the fuck is happening to me?" Jim steeled himself for a moment, before he managed to squeeze into his panty girdle which when fully on again compressed his crotch to almost female flatness. Jim let out a soft sigh as he finished getting dressed, kissed Maria goodbye and left for college. All the way to college on the bus Jim fretted to himself that everyone on the bus must somehow know that he was some sort of panty wearing sissy who was also wearing tights. That nagging fear stayed with him all day and for the second day in row found that he had zero ability to concentrate in class. As he was leaving class for the day, he was surprised when his lecturer told him that the college administrator wanted to speak to him urgently. 5 minutes later Jim was sitting in the college administrator's office as he received a finger-wagging lecture about how poor his grades and attendance were and that if there was no immediate improvement from him, that the college would have no alternative but to suspend him from the course. With those words ringing in his ears, Jim made his way home and when he got there hopped straight in the shower after undressing. As he was undressing, he felt it weird that after only a few days of his punishment, he was becoming comfortably accustomed to not only seeing his legs constantly encased in tight lycra, but also how accepting he was that he almost always now had a femininely flat crotch. He thought ahead to when his punishment would end in a year's time, and what a relief it would be to be able to wear baggy boxer shorts with more room to swing in. However, he knew that would not be today, because it was sexy clothes for him. Once in the shower, Jim again revelled in the sensations of his soapy hands caressing his smooth hairless body and he almost immediately got a hard-on. He hadn't came in 2 days now, and he was desperate for some relief. But somehow he was able to ignore his hard-on and managed to finish washing and drying himself without spurting his load. As he entered the bedroom he realised that he wouldn't be able to put on his sheer tights and panty girdle until he did something about his diamond- hard penis. He therefore went into the kitchen and, after retrieving them from the freezer, pressed a packet of frozen peas against his crotch. After the initial shock of the coldness had subsided, Jim's penis eventually shrank and when he took the packet of peas away from his numb crotch, couldn't believe just how small the cold had made his, already small sized, genitailia. Jim then made his way into the bedroom and again glided his shapely legs into his sheer tights and, after squeezing into his panty-girdle, waist cinch and hot-pants, slipped his dainty feet into his glossy stilletos. Just after he had put his feet into his heels, he absent-mindedly thought, just for a fleeting second, that both his feet had looked decidedly "pointy', in that his toes seemed to be crushed together. He quickly dismissed the idea as probably being down to the tight grip that the end of his tights had his feet in. Jim quickly put on a slim-fit t-shirt and made for the kitchen to make a start on dinner, walking as daintily as ever in his stilletos, with his hips having an ever increasing roll to them. Jim was unaware of the increased roll his hips were making, which seemed to be as a result of him being able to walk faster in his high heels. He was inwardly happy however that he had mastered the act of walking in stilletos so quickly and hoped that Maria would be pleased with him. He actually smiled to himself as he sexily minced into the kitchen. Once he had dinner set to cooking, he switched on the laptop and checked his e-mails. He had 3 new e-mails, which were from the on-line shoe stores he had bought from last night, confirming when his purchases would be delivered. It was now Wednesday. His boots would be delivered within the next 10 days, his t-bar shoes next Monday, and his bar shoes next Tuesday. None of the e-mails gave a delivery time, but instead said they could be delivered sometime between 08.00 am and 06.00 pm. Jim immediately recognised that there was a problem. He would be at college and Maria at work during the delivery times. How therefore would he take delivery of his new high heels? He decided he would discuss it with Maria as he closed the laptop and sat back to watch the news, absent mindedly crossing his pretty legs at mid thigh, hearing the. now almost familiar, comforting zip of lycra. As he sat there, he realised that his crotch was particularly uncomfortable and felt this was partly due to him taking, almost conspiratorial, glances his lycra encased legs and glossy high heels, and vowed to stop doing so.......unsuccessfully.