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Punishment 5 - by Debbie Johnson Chapter 1 - Delivery It was now Friday morning at 10.00am. Jim was standing in front of the full-length hallway mirror reciting his mantra. He was reciting it there, because Karen insisted he now do it there, so that he would have a visual aid to help get his mind-set as feminine as possible. As he said each part of his mantra (which he was instructed to do in as feminine a voice as possible) he was to gaze at any part of his body that his mantra related to.....which he dutifully did..... "My name is Debbie. I love my name because it is a really pretty name. And I sooo love being a girl! I love wearing sheer hosiery. (as Jim looked in the mirror at his pretty legs sheathed in barely-black 10 denier tights) I love wearing tight foundation underwear, the tighter, smoother and silkier the better. (eyes moving slowly down his body, at the light pink blouse he had borrowed from his girlfriend, his mind subconsciously regretting having such a flat chest) I love wearing hot pants, but I also want to wear the shortest of mini- skirts and tightest of dresses. (gaze shifting to his feminine crotch of his light blue denim hotpants) I never want to be without a full face of make-up. (looking directly into his own smokily made-up eyes) I never want to be without a spray of pretty perfume. (inhaling the feminine flowery scent that misted around his petite frame) I'm a real girly-girl and the thing I love most about being a girly-girl is getting to wear sexy, skyscraper heels. (eyes flitting down to his glossy stilettos, his mind now subconsciously associating sexiness with high-heels as his groin gave up yet another involuntary twitch) I wish I could wear high-heels to bed. (his mind also acknowleding that it sort of made sense for him to wear stilettos to bed, it would help his feet adjust quicker to wearing high-heels) I sooo love having the two best friends that can make my deepest feminine desires come true. Thank you Karen. Thank you Maria." As the 15 minutes wore on, it seemed as if Jim had entered some sort of trance state as his voice took on an increased sing-song feminine quality. Indeed, he was so far into this relaxed state, as his eyes roamed all over the feminine creature captured within the mirror, that he continued it long after his 15 minutes were up and he only stopped when he was interupted by the intercom buzzer going off in the hall. Without even thinking about it, Jim tottered over to the intercom, his rear swinging in an ever so womanly fashion. Again, without thinking about it, Jim pressed the button and automatically said in a feminine voice, "Hello....can I help you?" It was only when a gruff masculine voice replied that he had a delivery for a Miss Maria White that Jim suddenly came out of his reverie and his heart immediately started racing and almost leapt out of his chest. Jim was suddenly dumbstruck and didn't know what to do, when the man's voice questioned "Hello?...Hello Miss?...Are you still there?" Jim quickly regained his thoughts and realised that the man had mistaken (mistaken?) his voice for a girl's voice which he identified as a good thing (really?). Jim again pressed the button and replied, "Ye...Yes I'm still here. Ple...please come up," as he pressed the button which would allow the stranger access to the building. Jim's heart was racing as he tottered over to the mirror to check his appearance once more. "I've nothing to worry about," he said to himself out loud as his eyes ran up and down his reflection in the mirror. "When I open the flat door, all the delivery man will see is a pretty young woman." Jim's eyes couldn't help but return to his flat chest and he momentarily cursed the fact he was so small-chested. He knew that most men couldn't help but look at a woman's breasts. He did, however, console himself with the thought that he had sexy legs and hoped that the delivery man would eye those up instead. Even as those thoughts ran through his mind, Jim found nothing strange in the way that he wished he had a bigger bust and also that he wished that some random male would lust after his pretty legs. After a minute or so, as the delivery man ascended the stairs to the flat, Jim was startled away from his reflection in the mirror as the flat doorbell rang. He hesitated briefly before tottering over to the front door of the flat, all the time trying to whisper convincingly to himself that there was nothing to worry about and that he was just a normal girl, waiting at home for a delivery of some shoes. What happened next for Jim as a bit of a terrifying blur as he opened the door to be confronted by a hulking brute of a man, who had a large box at his feet. It wasn't lost on Jim that as soon as the delivery man clapped eyes on him, his mouth broadened into a wide grin, his eyes opening widely, as he drank in the sight of the lovely young creature that opened the door. Jim inwardly prayed that the delivery man wouldn't notice that he was blushing furiously. The delivery man's eyes continued to dart all over Jim's form, taking in the prettily made-up face, the petite torso (hmmm....tits too small he thought), moving to the sexiest hot pants he had ever seen on a girl, moving slowly down her incredibly pretty legs, on down to the fuck-me-shoes she was wearing. "Jeez...this bird must be getting ready to clubbing or something in that outfit!" the man thought to himself. After a few moments, during which Jim stood frozen in the doorway, not knowing what to do as panic increasingly overcame him, the delivery man asked Jim to sign for the package and held out the pen to his electronic reader. Jim took the pen and shakily scribbled his name ("wait!....what name did I just sign there?....Debbie?...what the Fuck!" he thought to himself quickly). Jim handed the man his pen back and, as he did so, the man handed Jim the box which had momentarily been at his feet. Jim snatched the box from the man and, after stumbling through a mumbled thank you, he darted back into the safety of the flat. After closing the door, Jim leaned back against it, all the while clutching the box to his (flat) chest as if his life depended upon it. As Jim stood there for a few minutes, his heart thumping and his nylon encased legs feeling like jelly, he felt total relief at getting through those brief minutes without his secret being discovered. In fact, a small smile flitted across Jim's face as he realised that Karen was totally right in what her earlier assessment of the delivery man's reaction would be. Jim didn't realise that he was actually pleased that a random man had found him to be so convincingly female and that he had probably descended the stairs to his van with a firm smile on his own face and an even firmer boner in his trousers (which he did!). Chapter 2 - Reflection Once Jim had regained his composure and his heart-rate had returned to somewhere close to normal, he minced his way into the living room, placed the box on the seat of the sofa and flopped down ungracefully beside it, before remembering himself as he femininely crossed his legs at mid- thigh. Jim stared at the box for a minute, while wondering if he should open it, or even if he was allowed to open it. He knew the contents had to be one of the new items of footwear that he had ordered a few nights ago, but wondered which it would be. As he recalled the different types of high- heels he previously had ordered over the internet, he felt more twitches in his panty-girdled groin, but no longer considered such twitches to be a bad thing, because, as Karen had said to him only the previous night, it was best that he got himself in the most feminine mind-set possible. So if he got excited about thinking about sexy footwear, then he was just being like any other girl who was fixated on shoes or boots. Looking at the size of the box, Jim thought to himself that it was likely to be too big for any of the the high-heeled shoes that he had ordered for himself, as he mentally tried to recall the image of the shoes he had bought.....being the t-bar stilettos, with the 5 and a half inch heel....and the black patent shoes with a six-inch stiletto heel and a 1- inch platform sole and three bar-straps running across the top part of the foot. As he tried to picture the sexy shoes, Jim was oblivious to the fact his flattened crotch was erupting in a series of almost continual twitches. "It must be the boots...a box that big," Jim said to himself out loud. "Must be," as he reached for the box and began to open it. It only took a moment for Jim to rip away the outer packaging before prising the top of the box open. As he did so Jim let out an almost inaudible gasp as his prettily made-up eyes looked upon the contents. "Wow!" whispered Jim gazing at the soft, black leather of his new boots as he stroked it softly with the tips of his delicate fingers. Jim realised immediately that he had made a good choice in opting away from the whorish looking patent boots that he first considered buying, before choosing these gorgeous creations. Jim loved seeing women wearing high- heeled boots and now, incredibly, he had his own pair. However, his face did show some concern at the height of the boots' slender stiletto heels which he now remembered being 6 inches in height. Lying in the box, however, the heels looked longer. Jim remembered that the boots also had a concealed 1-inch, mini, platform sole which, in theory, should make them easier to walk in. Jim's hands were trembling from a mixture of excitement and anticipation. He thought to himself that a man shouldn't be excited about taking possession of his own pair of stiletto-heeled knee-boots, never mind the thought of actually wearing them. But think that as much as he tried, Jim could not deny his own groin's betrayal of these thoughts, as his previous twitches of arousal had been replaced by an onslaught of full on arousal, as much as could be permitted anyway, given the tight imprisonment in which his panty girdle and hot pants continually gripped Jim's small cock and balls. Slowly, Jim removed first one, then the other knee-boot from the box. The boots were indeed exquisite. The black leather, being of obvious quality, had a lovely sheen to it. So much so that Jim thought to himself that he must make a big effort to keep them looking so nice, which shouldn't be too much of a problem, as he was only planning on wearing them indoors anyway. As he picked up one of the boots, he turned it over in his hands, looking at the finer details of it, from the rich-looking, yellow, leather sole, to the expensive-looking, synthetic material of the zip, to the intricate detailing of the stitching. It truly was a thing of beauty and Jim began to absent-mindedly undo the zip of the boot. Once the zip was fully undone, Jim slowly rubbed the delicate, inner fabric of the boot, delighting at how soft and almost sensual it felt as he thought to himself, "Wow...if it feels that good to the touch of the hand, I wonder what nylon-clad feet will feel like against it." Jim was unaware that he was smiling broadly as he clasped the back of one of the high-heeled court shoes that he was wearing before easing it from his tiny foot, followed by the other one. He then gently clasped the top part of the left boot and placed it on the ground in front of him. As he looked at his left foot, the re-inforced toe of his tights standing out in dark contrast to the rest of the sheer nylon, it almost seemed to be frozen in the same un-natural angle in which his court shoe had held it in only moments previously. As Jim slowly eased his hosiery clad foot into the welcoming soft embrace of the boot and slowly zipped it up, he was almost giddy as he seem to briefly have some sort of an out-of-body experience, as he wondered how he managed to find himself in the weird position of sitting on the sofa of his living room, wearing tight constricting lingerie, a female top, incredibly tight hot-pants and sheer hosiery, not to mention also wearing a full-face of make-up and a feminine hairstyle, and was beginning to pull on his very own 6-inch stiletto-heeled, fitted knee-boots. The feelings on Jim's nylon clad foot and lower leg being gripped tightly by the soft material of the boot's inner, as he slowly zipped it all the way up almost caused him to suffer from sensory overload. Once the boot was fully zipped up, Jim marvelled at how perfect a fit the (size 5) boot was. It was a 'fitted' style of boot, which meant it hugged every contour of his foot, slender ankles and leg perfectly like a soft supple second skin, and when he bent his leg at a right angle to give himself a better look at the boot's high stiletto heel, he could just about feel the rim at the top of the boot graze the back of his thigh. After a few seconds, Jim lightly grasped the other boot and slowly repeated the action of easing his other dainty foot into it's welcoming inner and slowly zipped it up. The zipper made a delightful rasping sound, which was almost as sexy as the boots themselves Jim thought. Once both knee-boots were fully clamped to his lower legs, Jim subconsiously marvelled in the sensory feelings they were transmitting through his sheer tights onto his skin. "Jeezo...if wearing boots feels this good, why aren't women wearing them all the time?" Jim wondered to himself out loud, again speaking in a most girl-like voice. Jim slowly started to rise from the sofa, holding on to the sofa arm as he did so. Jim had half expected to have some difficulty standing in the boots, given that the heels were 6 inches high, compared to the 5-inch stiletto-heels that he was more accustomed (already?) to wearing. Jim was pleased, however, that he had no dificulty standing in them as he started taking his first tentative steps in stiletto-heeled knee-boots. After he had walked up and down the living room a couple of times, Jim quickly made for the hall, eager to see how his new boots looked in the mirror. When Jim got there, his lipstick-covered mouth gaped in wonder as he took in the true beauty of the boots. All sorts of words flitted through his mind as he gracefully twirled and twisted to enable him see his new boots in the mirror from every possible angle .... 'georgeous'.... 'pretty'.... 'exquisite'....but only one word truly captured what Jim was thinking as he stared transfixed at his boots....'SEXY!'. Yes....no doubting it. Jim had to admit that when he was earlier wearing just tights and high heeled court shoes, his legs did look pretty. But now?....No denying it! His image shouted sex. "These boots are incredible looking" Jim thought to himself. Just then, a strange thought came into Jim's head. "If my legs had given the delivery man a boner earlier, just think the state he would get into seeing me wearing these boots together with the rest of my outfit." As Jim giggled and stared lustfully at his own reflection within the mirror, almost automatically, the heel of his right hand started pressing against his girlish crotch. As he gazed at his reflection in the mirror, he wondered whether his new stiletto-boots would look even sexier if he were to replace his hot-pats with a sexy little red mini- kilt.....as he began to say out loud, "My name is Debbie. I love my name because it is a really pretty name. And I sooo love being a girl!......" Chapter 3 - Questions Jim had worn his sexy new boots about the flat for a couple of hours, before taking them off and putting them back in their box. He had regained some composure earlier, when first gazing at his new boots' reflection in the mirror, when he had realised that he was rubbing the heel of his hand against his girlish crotch and that he was almost close to coming. Somehow Jim had managed to summon willpower from somewhere, preventing himself from what would surely have been a crashing orgasm. However, all this did was to increase the ache of his sexual frustration and inwardly prayed that Maria would spend some quality alone-time with him later that night in bed and allow him to orgasm for the first time in what seemed like an age, but what was, in reality, only a few days. During the short time he had wore his new boots around the flat, his eyes seemed to be magnetically drawn to them, whether being their reflection in the mirror, or just when he was sitting on the sofa. Jim eventually took his boots off and replaced them in the box in which they were delivered. As he slipped his dainty nylon clad feet back into place in their customary glossy, stiletto, court shoes, his primary emotion was worrying about the fact he had opened the box without any instruction from Karen (or Maria) to do so. He felt uneasy and even confused, because he wasn't even sure if he had needed any such instruction to try on his new boots, such was the strange manner in which he found himself thinking lately or, more accurately, 'not thinking' as he seemed to be automatically following any orders Karen and Maria gave him. Jim found himself wondering exactly what the two girls would say when they found out he couldn't even wait for them to get home before he gave in to the urge to try his new boots on. As he sat on the sofa, pretty legs crossed as if in their now natural position, his groin emitting a frustratingly sexual ache, Jim fretted that the girls might think that he was some sort of cross-dresser or something, which Jim knew for definite he absolutely wasn't (right?). What would he say to the girls if they accused them of being one? As his mind whirled, it subconsciously drifted back to his mantra and what Karen had said to him last night. He made his mind up that if the either of the two girls were to make an absurd accusation that he was some sort of cross-dresser, he would defend himself by saying that he was only following Karen's instruction, that he should accept that he was a girly-girl (for the next few weeks at most) and that he just tried the boots on to see if they fit him properly, and maybe even break them in slightly and that he would definitely deny to getting aroused from wearing his new high-heeled boots if so accused ....because he was definitely not sexually aroused by them ....no way....right! So it was eventually around tea-time that both Karen and Maria returned to the flat. As they came through the door giggling and chattering away, Jim was half-way through yet another recital of his mantra. When he saw the girls he momentarily paused and looked over to them smiling with, what seemed to Karen and Maria, a slightly glassy-eyed expression, almost like he was half asleep. On seeing Jim, Karen instructed him to carry on and finish his mantra 'session' in front of the mirror. Jim returned the gaze of his pretty eyes to his own reflection and started on his mantra once more. As he did so, both girls placed their shopping bags on the floor and hung up their jackets and, in doing so, exchanged smiles as they saw that Jim was now following his new instructions to the letter, as his eyes roamed all over the decidedly feminine reflection of his sexy image in the mirror, as he spoke softly to himself in a very convincingly feminine manner., both girls felt their panties dampen.... As soon as Jim finished his mantra, he tottered into the living room and seeing Karen and Maria sitting on the sofa, he minced over to them and nestled himself in his customary position, squeezed in between them. Jim found this position comforting but, as with a lot of things these days, he found that he could not really comprehend why he felt that way. As he lowered himself onto the sofa, he couldn't help but give a sidewways glance to Karen's lap, on which now lay the box containing his new knee- boots. As soon as he was seated, Karen said to him, "So Debbie, what's this then?" gesturing to the box, although Karen knew exactly what was in the box, as she and Maria had had a quick peek inside as Jim stood admiring himself in the hall mirror. "It's a delivery Karen," replied Jim (oblivious to the fact that he was now answering to the name 'Debbie', just as automatically he did when Karen had taken to calling him 'Princess') "It's my new knee-boots," he continued uneasily. "Really? Knee-boots?" said Karen, a small smile registering on her face "what time did they come?" "I think it was just after ten this morning," replied Jim. "I was in the middle of reciting my mantra when the hall buzzer went." "I see," said Karen. "So, for the second time in two days, you had to interact with someone other than me and Maria dressed the way you are.....dressed all girly-girl and such. So how did that go then? Any problems? Did the delivery man...and I assume it was a man? (as Jim nodded yes) So did he accuse you of being anything other that the pretty young woman you appeared to be? Did he threaten to call the police or beat you up because he thought you were a man trying to disguise yourself as a girl? Or were his reactions totally different to that? Tell me and Maria...how did it go?" "No...I mean ye...yeah, his reactions were totally different to that. I was really scared though, my heart was thumping when I opened the door. I guess I was scared that he would recognise that I was really a man (as barely disguised sneers flitted across both the faces of Karen and Maria) and that he would maybe get angry with me or something, but...(as Jim smiled and looked alternately at both girls) but it was totally different because he was...well...(as Karen gently urged him to continue) well he kind of looked me over and smiled. I think he totally thought I was a girl!" There was a slight pause between all three of them as Karen and Maria gave each other knowing smiles. They both then put their arms around Jim and congratulated him and said that they had known that there was nothing for him to have ever worried about, because he did look every inch the pretty girly-girl after all. Jim winced and knew that he should have rebelled at hearing that description of him, but all he could actually feel was relief that he had passed another test and that he now should have no further worries taking delivery of his other new sexy (sexy?) shoes when they eventually come. "I was a bit worried though," said Jim, "because my chest is so flat and...well I think the delivery man noticed it was flat, but then his eyes carried on down to my legs and seemed to linger there. That's what I hoped would happen." "What do you mean?" answered Maria this time. "Well," gushed Jim, who seemed to be in full flow by now, "I know that I am flat chested, but that my legs are pretty and I kind of hoped that the delivery man might think so, so as not to notice my flat chest." Jim's breathing had taken on a quicker tempo and his face was flushed slightly as he had said this, darting glances back and forth between the two girls. "I think you should be very proud of yourself Debbie," said Maria. "You do certainly have pretty legs and those sheer tights you are wearing make them look downright sexy. There's no way any man could not have thought you looked like nothing other that the pretty young woman you appear to be," as she and Karen gave Jim yet another round of hugs. Again, Jim should have fought back against Karen's latest verbal assault on his masculinity, but instead he found himself being pleased that his relations with Maria seemed to be getting on a better footing over the past couple of days, as he settled more into his punishment. Chapter 4 - Treats Once the two girls had finished hugging the feminised young man, Karen surprised Jim by placing the box containing his new knee-boots on the floor and instructed him to go and fetch the shopping bags from the hall. Jim did so without even thinking otherwise and, when he handed the shopping bags to Karen after he had tottered back into the living-room, before he could settle himself back on the sofa he was instructed to stay standing. This instruction caught Jim slightly unawares and, not knowing what else to do, he stood silently with both high-heeled feet together, hands behind his back, head slightly bowed. Jim's latest gestures did not go un-noticed by the two girls and they only served to confirm their, earlier voiced, suspicions that Jim's psyche was tapping into some deep submissive reservoir within his mind. Karen picked up one of the bags and took from it what looked to be another shoe box. As she opened the shoe box she took out a pair of stiletto-heeled sandals. As Jim looked down on the sandals, Karen spoke; "Right now Debbie, pay attention...(as Jim raised his head and imperceptibly tried to stiffen his posture....which only served to send his bubble-butt thrusting out slightly more than it already did, together with his non-existant bust)...I told you that for you to get better used to wearing high-heels, the best thing for you to do is wear such shoes to bed. These lovely sandals are the high-heels I have selected for that. They are a cheap pair that I got in the sale. The reason I have went for a cheap pair, is that wearing shoes to bed can cause them to become worn, so by picking a cheap pair there is no real loss. If you look at the sandals, you'll see that they have a 6-inch stiletto heel and a 1-inch platform. They have multiple straps that cover most of the foot and have a zipper up the back. They are a mock-suede fabric and one of the benefits of you wearing these high-heels to bed Debbie, is that when you get up in the morning, you simply have to roll out of bed and continue wearing them until it is time for you to get showered and dressed. The only thing that I personally don't really like about the sandals is their navy blue colour, but I guess that is why they were on sale after all. Obviously, they are in a size 5, which is your new shoe size anyway. What do you think Debbie? Do you like them?" Jim looked down on the high-heeled sandals Karen was holding and before he knew it had replied "Yes...they are very sexy" before catching himself and continuing "I mean...they would look very sexy on a girl " "But Debbie," said Karen, "haven't we already gone over this? Haven't we already established that you are a girly-girl and that the thing you like best about being a girly-girl is that you get to wear sexy skyscraper heels? Isn't that the case?" It was almost as if a switch had been thrown in Jim's mind on hearing Karen's words as his mind started spinning. "Wh...well yes...yes...I think...I mean yes, the thing I like best about being a girly-girl is that I get to wear sexy skyscraper heels," said Jim in a feminine melodic tone as his mantra automatically started to kick in. "Good...that's what I thought," continued Karen. "Now, I think we would all agree that it would be almost impossible for you to try to attempt to pull on pyjama bottoms while wearing such skyscraper heels. So, we've come up with an ingeneous solution (Jim's mind foggily agreed that it would seem difficult to pull on pyjama bottoms while wearing any shoes , never mind such sexy shoes as those Karen had bought for him, but for the life of him, Jim couldn't see any way round it, never mind the obvious solution of him putting on his new high-heeled sandals after his pyjama bottoms) So the solution is for you to wear nighties to bed ("What?" went Jim's whirling mind). That's why we bought you some of these nice sets. (As Karen said this she pulled several packages out of the bags. Each package was wrapped in clear sellophane and Jim could make out that each had several shiny (satin?) items contained within, with what looked like contrasting white lace detail. The 4 colours he could make out were lemon, pink, red and black.) Each one of these packages contains a baby-doll night gown, a short matching robe and a set of matching panties with lines of frills at the rear. Now Debbie, I know that you already love wearing a panty-girdle during the day, as well as your sheer tights, so from tonight, you will take off all your clothes except for your panty-girdle and tights and slip into your baby-doll nightie, frilled panties and stiletto sandals, before slipping under the covers. How does that sound? Eh?" As Karen eyed Jim intently, her panties again dampening even more with each second. Jim stood silently for a few moments, mind awhirl, eyes glazed and mouth agape after hearing how he was now seemingly going to be dressed femininely 24/7...even while he was asleep. Only a few days ago he would have asked the question, "Why? Why did his 'punishment' have to now extend to his sleeping hours?" But now, as his mind became even more confused and his manner even more submissive, Jim simply whispered, "Great Karen...that all sounds great, thanks." Karen's smile broadened widely on hearing Jim's reply, although silently, she was a little disappointed that he had seemed to give in so easily. "Well," she thought to herself, "we'll see how he reacts to his other treats." "I'm very impressed by the improvement in your attitude Debbie," said Karen. "Much better that having you all hystrionic-like you have been recently. Your new and improved attitude can only serve to allow you and Maria to get through your punishment and get back to normality as soon as possible." "What?...Punishment?...Right, that's right" thought Jim "Punishment... that's what this is all about, how could I have nearly forgot that?" "So," continued Karen, "some more treats for you Debbie. Now that you are going to be wearing high-heels when awake and in bed, it makes sense for you to wear them every possible minute of the day. So the only other time when you will need to wear them is in the shower. That's why we got you these. These are a pair of plastic mules that have a 5-inch stiletto heel, with no platform in the sole. I hope you appreciate the trouble we had to go to, to get you these mules...we actually had to go to one of those sex shops, but we got there in the end. So the good news, is that except for the brief times when you are drying your feet after a shower or changing clothes, you will be able to always wear skyscraper heels....you lucky girly-girl you!" As Karen had been explaining this, Jim's whirling mind was unable to fully comprehend what it really meant for him. What he didn't know was that by having his feet strapped in high-heels for almost every minute of every day, the effect on his tendons and muscles would be that they would shrink and atrophy over time, until such a point that eventually, maybe only a few months in the future, Jim would be unable to walk at all unless he was wearing high-heels. Of course, Karen knew this, as did Maria. Chapter 5 - Corsets "Now... some more nice treats for you Debbie, you lucky, lucky girl you," continued Karen. "We all know that you have really taking nicely to wearing hot-pants around the house, but as you are continually reminding every one, you wish you could wear the shortest of skirts and the tightest of dresses (as Jim's mind automatically repeated his mantra that he did indeed wish he could wear the shortest of skirts and tightest of dresses... "Wait! What I don't really want that do I?" thought Jim). Well, we haven't managed to get you any dresses yet, but we have managed to pick up these two skirts for you, one in black and one in grey." As she said that, Karen pulled two skirts from one of the shopping bags. "Both skirts are pleated mini-skirts, with the pleats going from the hem to the waist band. They both have elasticated waist bands, which will be handy as we intend to do something about that flabby tummy of yours." As Karen said this, Jim looked down at his waist line. He didn't think he had anything close to a flabby tummy, especially given that the waist- cinch he was wearing had managed to pull his waist in from it's normal 27 inches to a ridiculously small 24 inches. He was shaken from these thoughts as Karen continued. "For the first week or so, you will only be required to wear these to bed at night and you can change out of them into your normal waist-cinches when you get showered and changed each day." While saying this, Karen pulled some more objects from one of the other shopping bags. "These are corsets," she said studying Jim's expression which was gradually becoming more open-eyed and quizzical. "Before changing into your baby-doll night clothes each night, you will be required to lace yourself into one of the corsets. We have bought you 4 corsets for now, so that you will be able to lace yourself into a clean one each night and hand wash your previous night's corset each morning. We do think that you may have difficulty lacing yourself into a corset the first time you try, so Maria and me will kindly help you for the first few nights. However, after that, we both expect you to be able to lace yourself down to at least 22 inches without any problems. As time goes on, and your waist begins to train itself into a more acceptable shape, we do expect that you will be able to lace yourself down further, is that clear?" Jim slowly nodded an affirmative, but in his mind he was asking questions. "Wha?... what?... 22 inches?... she surely can't be serious can she?... and... and smaller than that?...how much smaller for fuck's sake?" "So... now I wan't you to repeat to me an Maria what exactly your new night wear will consist of from now on," said Karen. Jim could barely bring himself to utter the words and at first his full, pretty lips seemed only able to open and close without any sound. Then... almost a whisper at first then more loudly, again in a now almost natural feminine manner, Jim replied, "I... I'll be wearing sh... sheer tights, pa...panty girdle, corset, b... baby-doll nighty, frilly panties and...and stiletto-heeled sandals to bed," his head spinning at the thought. Where will all this going to end Jim thought. However, his crotch was again betraying him as it twitched away at the thought of someone going to bed dressed almost like a whorehouse prostitute... he just wished it wasn't him that was going to be so dressed. "Good girl Debbie. And such a luckly girl you are at that getting to go to bed all prettied up. But... the treats don't stop there you lucky girly-girl. Now... we did tell you that we had a plan in place to stop you fiddling with your bits when me and Maria weren't here to look after you, do you remember that?" Jim nodded hesitantly and he couldn't help himself as he blushed even more furiously than he already had been. Both girls couldn't help but notice Jim's face take on an even darker shade of red, even under the silky foundation that covered his face. It was Maria who spoke this time. "Why are you blushing Debbie? MY GOD! Have you been playing with yourself? Even after I told you it was strictly forbidden? Well? Have you? Speak up girl? Tell me!" Jim's lower lip started trembling and his eyes started to fill up. What struck him as strange was that he immediately thought that if he started crying, he would mess up his pretty eye make-up... why the fuck was he thinking about that at a time like this? Forcing himself to speak, Jim replied, "I... I didn't really mean to and...I...I didn't follow it through...so to speak, but...but I did kind of start to rub myself earlier today. But I did manage to stop in time...so that...that...I didn't...you know...finish." Jim stood silently almost at attention in front of the two girls, although he couldn't bring himself to look them in the eyes, as he instead looked down at the patent-leather high-heels he was wearing. Karen and Maria looked at each other for a few minutes, before Maria asked "So... what are you telling us Debbie? You took down your hot- pants, panties and tights and wanked yourself off...and that you didn't really mean to? Is that what you are trying to tell us? Was it because you were attracted to the delivery man? Was he cute? Was he a hunk? Did you fancy him? Is that it?" "No... no...that's not how it happened at all," stammered Jim. "No...it was when I tried on my new boots that it happened." On hearing this Maria stared intently at the petite feminized boy standing in front of her. Never in a million years could she ever associate that image with being that of her boyfriend. She hardly found it imaginable that there was ever a time when she did consider him to be male, never mind her actual boyfriend. "What the fuck did I ever see in that fucking sissy?" she thought to herself, because that was exactly what she saw standing before her now...a sissy! "Tell us exactly what happened then Debbie," barked Karen totally intrigued by what Jim was talking about. "And no lying... because we will see through any lies immediately!" "After the boots were delivered, I took them into this room and... well... opened the box. The boots looked so nice... I... well I thought I'd better try them on... just to make sure that they fitted me... obviously. And... well... once I had them on, I... I tried walking in them to... to try to break them in a bit that is. Af... after a few minutes walking in them, well I went out into the hall and... and had a look at them in the mirror... ju... just to be sure that they did look okay and fit me that is... and... and well I thought that while I was there I should... you know... be a good girl (!) and recite my mantra. Tha... that's when it just seemed to... like... happen..." as Jim's stuttering voiced trailed off. Both girls looked alternately at each other and back at Jim with increasing incredulity as he stood there motionless, looking straight down at his high-heeled shoes. "What exactly 'happened'?" asked Maria slowly. "I... I kind of... started.... started rubbing myself," said Jim as his head looked like it was about to explode, such was the severity of his blushing. "Show us!" barked Karen. "WHAT!" exclaimed Jim as he looked first frantically at Karen, then to Maria, then back to Karen. "You said you rubbed yourself," replied Karen. "Show us. Show us exactly how you rubbed yourself. Do it now girl!" she ordered. With a start, Jim's hands unclasped themselves from behind his back and he automatically brought his right hand to his crotch. Both Karen and Maria watched fascinated as he did so, Karen's own groin, in particular, almost aflame with arousal. Subconsciously, Jim shifted his stance slightly, as he spread his feet about a foot apart and placed most of the weight on his left foot, a stance that both girls thought to be decidedly feminine. In his continually confused state of mind, Jim wasn't sure whether Karen was telling him just to mimic his 'rubbing' actions of earlier that day, or whether she was instructing him to actually put any meaning into it and actually try to bring himself off. Jim was way beyond what could be called embarrassment. As his heart pounded away and as his mind was again caught up in a whirl of confusion, something strange started to happen. As the heel of his hand came into contact with the front of his sexy hot- pants, Jim's groin gave out another twitch, quickly followed by another and yet more. This couldn't be happening to him surely, Jim thought to himself. I can't be getting turned on surely, he thought, as he applied slightly more force and increased the motion of his hand. In doing so, Jim closed his eyes and recalled his own reflection when he stood in the hallway earlier that day. A reflection of him wearing his sexy, new, high-heeled boots, sheer tights, hot-pants, feminine top and make-up. Subconsciously...a soft moan escaped Jim's pretty lips as he momentarily became lost in his own little world, a world in which he wears sexy stiletto knee-boots and where he is desperate to come at any cost. Karen and Maria sat on the sofa, mouths wide open, mouths which mirrored their eyes, which themselves were like saucers as they took in the spectacle unfolding before them. They exchanged quick confused glances with each other as if both of them were uncertain what to do. Jim seemed to be spiralling out of control. Here was Maria's supposedly 19-year old boyfriend, standing before them perched on a pair of glossy high-heels, rubbing the crotch of his hot-pants with the heel of his hand in what could only be described as a picture of female masturbation. There was almost no hint that the creature standing before them was even remotely male, as it looked to be hurtling head-on to orgasm. It was Karen who finally decided to take back control as she stood up. Jim had his eyes closed so did not see Karen approach and stand directly in front of him, though he was probably distantly aware of the feel of her breath on his face as she approached. Without warning, Karen raised her hand and brought it hard across Jim's cheek with a deafening slap. The slap had the desired effect as Jim stumbled back slightly on his high-heels, opening his eyes and bringing both hands up to his face in defence, his eyes and mouth opened wide with shock. Karen and Jim stood there for a few moments each sizing each other up before Karen shouted at him, "YOU DISGUSTING LITTLE BOY! YOU FILTHY, DISGUSTING, PERVERTED LITTLE BOY! WHAT IS WRONG WITH YOU? YOU THINK YOU CAN STAND IN THE MIDDLE OF THIS LIVING ROOM AND TRY TO WANK YOURSELF OFF?! DO YOU?! YOU DISGUSTING EXCUSE FOR A BOY." Karen stood for a minute looking directly into Jim's eyes, eyes which could not return her gaze, eyes whose mascara was now running down the face to which they belonged, as the tears of the feminized boy erupted and rolled down his pretty face. Karen sat back down on the sofa. Crossing her legs and arms as she looked up at the blubbering wreck Jim had become and asked, "Well? What have you got to say for yourself?" Jim didn't know what to say. He couldn't think straight as the confusion coarsed through what was left of his fragile mind. Karen was right he thought to himself. What the fuck was wrong with him? He had only moments earlier been standing in his own living room trying to bring himself to orgasm... in front of his own girlfriend and her best friend... what was he thinking? what was wrong with him for fuck's sake!? And why had Karen called him a boy? He knew that secretly (secretly?) he really was a boy (wasn't he?) but Karen had been calling him 'Princess', 'Debbie' and 'girl' all week, so why was she now saying that he was a boy? This was all way too confusing for Jim, who as he looked down past his pretty legs to his sexy shoes, couldn't think of anything to say, so he stood with his head down in total shame. Karen smiled at Maria, who nodded back to her friend and winked conspiratorially. "Now now," said Maria softly as Jim lifted his head to look at her, his sniffles dying down slightly. "Come here, here sit between us here on the couch Debbie." as she patted the sofa. Jim tottered slowly over to the sofa and eased himself into position between the two girls, again, feeling that same comfort that sitting between them gave him, albeit that he was now a bit more wary of Karen, after being on the receiving end of her almost brutal strength. As he sat, he again automatically crossed his legs at mid-thigh, almost feeling reassured by the now normal sound of the material of his tights as his legs rubbed sensuously together. As he sat there, first Maria, then Karen placed a comforting arm around Jim, both feeling the straps of the boy's bra as it dug ever so slightly into his slender shoulders. "Now. That was quite some performance you put on for us Debbie. Wasn't it?" asked Maria soothingly, almost as if a 'good-cop bad-cop' situation was now playing out. "Eh Debbie? I asked you a question sweetie." As Jim looked down at his nylon-encased thighs (twitch!) he nodded almost imperceptibly and whispered, "I'm sorry Maria." "Well... I think we all know that your sorry," said Maria ("Well a sorry excuse for a man really," she thought to herself) "What we have to do is come up with a solution to make sure there are no repeat performances of the one that just occurred. Don't you agree? (as Jim softly nodded yes). Good girl ("girl again?" thought Jim). That's why we've arranged for someone to come here tonight to help put a stop to your unforgivable urges. He'll be here at 8.00 pm to be precise. Karen and me have already spoken to him on the phone briefly and we believe that once he has been and gone, you won't have to worry about that little thing in your panties causing any more problems (as Jim winced slightly at hearing the word little... but only slightly). So what do you say Debbie? Shall we get you all cleaned up, have something to eat and get you changed into some more appropriate clothes for later on? Eh? What do you say?" Jim had zero fight left in him, or was that now zero willpower. He couldn't tell the difference and, if he was being honest with himself, he didn't really have the energy to care either way. He simply lifted his head to look into Maria's beautiful eyes and whispered, "Yes." "Good girl Debbie," said Maria, as she kissed Jim on the cheek, before grabbing his hand and leading him into her bedroom. "Let's fix your make-up and then you can get started on making us something to eat," said Maria. "Talking of make-up. We didn't get round to showing you the rest of our purchases, but we did get you your own make-up kit, so after today you will be able to start practising at putting it on yourself. Isn't that great?" "Ye... yeah Maria, sounds great," replied Jim slightly unconvincingly, as he thought to himself that fixing his make-up just now seemed like a bit of a waste of time, if he was going to have to take it all off later when he would have to dress up as a boy for the visitor due at 8.00pm......