The Farm School Sissy free porn video

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INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much as every community is generally autonomous to set it's own rules and values, bizarre or arbitrary as they might be. Jesse Cotton is an outsider, gentle, and a loner. A perfect target for the tastes of the particularly powerful and perverse ladies that run the school. Dale and Jesse don't realise but their victim was chosen almost from the moment he came to their attention. My plan was for Jesse to "fail" in his first term, and succumb to more indignities, hormones perhaps. The relationship with Dale might come to the attention of the ladies and be used to further humiliate Jesse, and Dale too probably. I had planned to write the next chapter from Jesse's perspective. Anyway enjoy what there is.... You might first hear the rustle of those sissy petticoats if he was close by, or the click of heels if that's what they had him wear that day. But you'd nearly always hear the tinkle of all those bangles, if you didn't you'd catch the scent of the sickly sweet perfume the house Matrons seemed to love to douse him in. How could he let them dress him like that? It was so creepy to see, and I know many boys felt disgusted by him. What was worse really was that he was so obviously utterly terrified of the Matrons that he'd tap about in his heels so prissily even when they weren't around. He'd even talk like a girl, and even redo his lipstick like a proper girl whenever they told him to. Most boys said they'd rather spend a whole year in the "cage" than be a Sissy like Jesse Cotton. I'm pretty sure I would. It's not like Cotton even spent an hour in the cage before, he was always a good kid, if a bit shy and goofy. How he ever got mixed up with the Sykes brothers nobody knows. It was always going to end bad. I don't know the details but the Syke's were running some kind of porno mag library or something, Cotton was some kind of runner, and you could see he felt proud to have tough friend's like the Sykes. When their little business was uncovered it seems the devious Sykes brothers managed to frame poor Cotton as the brains and leader of the whole thing. It was laughable to the other boys that Cotton could order the Sykes about like that. Whatever, the school council fell for it. If Cotton had done the dirty like that on Steve or Kevin Sykes he'd have been dead, but it was OK for the Sykes to do the dirty on him. I'd never ever trust them. The brothers didn't get off scot free. They both got a week in the cage, and were put on "report" for the term. Mysteriously Cotton just disappeared at the same time that we were told Matron Janice was going away on a special project for a month. I don't think anyone linked the two events at the time. Jesse Cotton might have been a bit of a wimp, tallish, but skinny, and crap at sports, but he seemed a decent kid. Anyway I risked a detention for insubordination and stopped Vice Principal Darlene in the corridor a few days after he disappeared and asked her if Cotton had swapped farm schools. They did sometimes pass on some awkward kids to other places so it wasn't such a stupid question. Miss Darlene surprised me by actually smiling at me, which was kind of scary. "Don't you worry Jake, he will be back in a few weeks, and..." She hesitated a moment. "I'm sure he'd be a much better boy. You'll see," she said still with that creepy smile. I wasn't sure what to make of that. She'd even called me Jake, and not Clarke, or even just "boy." I told the other boys, but even after being gone just a few days nobody was much interested in what had happened to the new boy Cotton, and nobody worried whether he came back or not. Within a week I'd pretty much forgotten about him too. A fourteen year old boy has plenty more to think about. The special assembly was pretty memorable. Special assemblies meant trouble for somebody, but if you were in the audience you were usually safe, and being there was better than work or lessons. This must have been a pretty special special because they even let two "untouchables" in, and temporarily took poor Edwards out of the cage. When VP Darlene came on stage with a beaming Matron Janice and a really soppy looking girl there was a bit of a buzz amongst the guys. We didn't get to see many girls of our age, and especially not in school, and we didn't get out much. Not that the girl was that hot. She was slim, and a bit shy I guess. She was dressed kind of weird though. She wore a frilly kind of pink dress and her hem was short, and the skirt was sort of filled out with petticoats. It wasn't exactly a little girls party dress, but it was a bit childish and a bit too girly. She wore white tights and lacy ankle socks, and gleaming white mary janes with a little heel like my sister used to wear. Her head was bowed so I couldn't see whether her face was pretty or not. Her hair was a shortish blonde bob with a huge pink barrette clipped to the side. She seemed to clutch her little cream clutch bag for grim life. The buzz of the guys, surprisingly unchecked by VP Darlene so far, seemed to make her even shyer and her head almost bowed into her chest. The VP walked to the lectern. "Take a seat please Janice and you too Sissy." She smiled to the Matron and the strange girl, whose name was obviously Sissy. An oddball name for an oddball girl I thought. Janice sat primly, her long legs crossed at the ankle as usual. The weird girl sat a bit awkwardly I felt. She smoothed the back of her dress as an afterthought before sitting, then crossing her legs like Janice but only when Matron gave her an odd look. There was a pretty flash of fluttering mascaraed lashes as she glanced across to Matron Janice, but soon her head was bowed to her chest again, and she fingered her little handbag with her pretty pink varnished nails rather nervously. VP Darlene had finally had enough of our murmurings and called us to attention. "Boy's please, your attention," she boomed. Silence fell, but I bet nearly every eye was on that odd girl sat on the stage. "About a month ago we had a very unfortunate incident regarding the circulation of unsavoury, sexist, and frankly disgusting material intended to denigrate and disrespect womankind." It took a moment for me to process "VP Darlene speak" into the Sykes and Cotton porno mag incident. "As you are no doubt aware two of the culprits have been punished already. Some of you might think they were too leniently dealt with given the enormity of this crime. However I'm assured that they were deceived into this transgression by the influence of a new and immoral presence in our midst. I too, I must admit to my shame, was deceived by this particular boy, and never imagined such a seemingly quiet, polite, and gentle child concealed such a monstrous heart." She paused a moment to look amongst the assembled boys as if seeking out such a "monstrous heart" amongst us. We all involuntarily returned her look with our most angelic expressions. Satisfied apparently that our hearts were pure, she continued. "What is a woman?" she bizarrely asked. There was a mini buzz of surprise amongst the guys at this question. "A woman is not an object, nor is she a toy of man," she added, answering her question herself, to our relief. "There is a certain type of man who thinks women are objects, that they dress and act purely to please men. They believe that women are weaker, inferior to man, subservient to the male. They effectively believe that woman were put on this earth merely for their satisfaction." The VP was obviously "going off on one now." "If a man who thought like that were to create a girl, perhaps of your age boys, what would she be like, how would she be defined?" A murmur of puzzlement broke her apparent pause for a response. "You'd be surprised to know that myself and Matron Janice, and the other Matrons have been giving that question a great deal of thought. That does surprise you doesn't it boys?" The boys hesitated a moment because we weren't sure if this question was going to be answered by the VP herself again. "Y...yes," we eventually dutifully replied in a ragged chorus, even though we weren't sure exactly sure what we were meant to be surprised by. "Well we have given it a great deal of thought I can assure you. We've even included the ladies of the outer community in our deliberations." Another pause for us to take in the incomprehensible. "This girl, the creation of such a man, would most certainly be a slave to every aspect of subservient and debilitating femininity. She'd wear make up at all times don't you think? She'd always wear heels that made walking preposterously difficult sometimes. She'd never wear trousers or jeans, always skirts or dresses no mater how awfully impractical and unsuitable they might be." Her audience were lost now. We all tried to hide our bewildered expressions. "And what of her pursuits? Do you think she'd be a mathematician, or teacher like myself?" The boys hesitantly shook there heads and mumbled "no" in response to the VP already shaking her head. "Correct. This poor creature's only pursuit would to be pretty, to pamper to the male's ideal of fragile and submissive femininity. Her pursuits would be the so called 'feminine pursuits' of cooking, cleaning, and keeping home. Her supposed hobbies would be needlework, sewing, or dressmaking perhaps. Her every thought would be how to please men, how to ensure she is always presentable and feminine both in appearance and in demeanour. In short she would be a slave to a particularly perverted male ideal of womanhood." I think even the VP was beginning to notice that she was losing the comprehension of her young male audience now. "So I think you are perhaps wondering why I'm telling you about this distorted male ideal of femininity?" A few hesitant nods amongst the guys, unsure if they were meant to respond or not. "A few years ago before Principal Martina took office we used to have amongst our array of necessary tools for the better guidance of young boys the tool of Sissydom." We boys knew all too well what were the supposed "necessary tools for the better guidance of young boys." There was the strap and the cane, the cage, the "untouchables" and a few other more minor unpleasant and painful punishments for boys that got out of line. Sissydom didn't really mean anything. "Principal Martina objected to the use of Sissydom in bettering her charges on the grounds of it distorting the characteristics of femininity in the eyes of those boys. I shall make a very rare exception to never criticising my peers in front of you boys to just say that I'm not completely sure dear Martina completely understood the purpose and benefits of Sissydom. "However myself, and most of the Matrons always felt Sissydom was an excellent tool for the improvement of certain boys. It was a very suitable tool for those boys who displayed excessive weakness or timidity, since Sissydom demonstrated to them the extreme consequences of actually enforcing weakness and submissiveness upon that child. It was useful too for the other types of boy who disrespected female authority or who showed signs of perverse attitudes to women in general, because understanding comes when you are walk a mile in the other's shoes." "I must admit too that we poor women, being surrounded by rough boys all the time, did miss the company of young women, and the help of willing gentle and uncomplaining hands. We also missed the opportunity to express immoderate levels of feminine fancy. More so, a really accomplished Sissy could be a splendid daily assistance to a hard working Matron I can assure you." The VP had a rather creepy dreamy look in her eye. Personally I wasn't really getting what she was talking about, but the beginning of a buzz from a few of the boys made me wonder if this wasn't something big. She snapped out of her reverie anyway and continued. "Well boys you may have noticed that Principal Martina has been absent for some weeks now...." We'd noticed that she seemed on the edge of a nervous breakdown for ages. "...well I'm sorry to say poor Martina has had to take early retirement due to ill health." A pause for us to show our sympathy. "For the moment I am taking over as acting Principal." A not exactly celebratory murmur passed amongst the audience. "I'm very much hoping that my appointment as permanent Principal will be confirmed very soon. So anyway with poor dear Martina's departure I am reinstating the 'role' shall we call it of Sissy in this establishment." I wasn't sure now if that was her speech over, her pause was so long. We'd never had any explanation of the presence of the weird girl either. Not that it wasn't unusual for stuff to go unexplained in this place. "So, referring back to the awful incident I began talking about in this assembly, I believe I left one thread unresolved. The two minor perpetrators have been dealt with, the 'ringleader' so to speak had shocked our sensibilities so much we had hard decisions to make." "The wicked boy, Jesse Cotton, was new to our establishment, and I was sorely tempted to simply return him to his previous establishment, or find some new more suitable destination for the troubled child. However such was the magnitude of his misdemeanours I felt it was our solemn duty to rid the boy of his distorted, perverted, and misconceived attitudes. We shouldn't merely shuffle him off to some other school only for them at a later stage to realise how we'd so cowardly merely absolved ourselves of the responsibility of such a 'snake in the grass.'" "I wasn't sure we had the tools to redirect such a boy as Cotton. Yes, we could make him suffer, we had the tools for that. However could we reform this devil in angel's form?" "Well we did come up with a plan boys, which ironically was facilitated by the untimely departure of our dear colleague Miss Martina. Matron Janice put herself forward as the initiator of this complex path of reform. Myself and the Matrons gave considerable time to planning and preparing every aspect and detail of this programme." "Something you boys may not be aware of is that dear Janice hasn't always been a Matron in an establishment such as this. She first trained as a nurse whilst in her spare time doing a little modelling. She later changed career to run a successful provincial beauty salon, before she had the calling to so ably fulfil her role as a Matron in institutions such as our own." Feet were beginning to shuffle now. VP Darlene's speeches were normally long and often incomprehensible but now she was rambling on about the history of the Matrons this speech could prove to be even more boring then usual. "So, given her experience, it was with much confidence that I freed dear Janice for a whole month to embark on a special project to lay down the foundations of the first of possibly many programmes to reform a certain type of boy, using a remedy quite suitable to the crime. It was a heavy responsibility upon Miss Janice's shoulders since her first charge was one of the most devious miscreants we have ever had in our midst. However on first appearances I'm suitably impressed by our Matron's thoroughness and rigour." Perhaps some of the boy's were following this a little better than I was because in a couple of corners there was hushed whisperings of apparent astonishment. Some boys too seemed to be more intently examining the soppy girl sat with her head now almost buried in her chest her pretty hands now feverishly fiddling with her clutch bag. Personally I was none the wiser, I followed that the Principal had now gone, and some ramblings about men and women, and something about a new "torture" called sissydom. On reflection maybe I was a bit thick, but honestly at the time, like the majority of the guys, I thought this was just another random rambling from the VP. Also as she droned on longer I began to wonder if this assembly really was truly a better alternative to actual work and lessons. The VP, or acting Principal as we now knew, paused again to look amongst the boys. I think most faces stared back rather blankly, I know mine did. I think she was looking to see if we were keeping up, and most of us obviously weren't. Usually our "lack of comprehension" sent her into a hissy fit, but to our surprise she smiled broadly. That felt more blood curdling then a hissy fit I can assure you. "So a few words from dear Janice, and we'll make our....our introductions." She smiled. She took her seat, still smiling, and the elegant but hardened Matron Janice stepped up to the rostrum. "Good Morning boys," she piped. "Good Morning Miss Janice," came the ragged reply. "Just a few things to remember boys. Firstly, our Sissy isn't a symbol of femininity, but a distorted and extreme vision of the female kind, the notional ideal of femininity imagined by a certain type of misguided male." Something our acting Principal and Matron Janice had in common was their ability to talk in riddles. An odd thought did go through my mind however. This was that they both were going on about sissies, and wasn't that strange girl called Sissy too? What a funny coincidence I thought. I know how stupid that sounds now, but it was genuinely what I was thinking at the time. "Secondly boys, whilst humiliation and shame are a very important part of this programme, you, the boys, are to treat our subject with a degree of respect, and according to the rules which will be explained to you in due course. It is for us the staff to develop situations which may be extremely humiliating and shameful to the subject in order to better achieve reform. Humiliation is like a boosting injection in a programme like this, an intense dose of our medicine, it isn't sought out of cruelty but merely to better the outcome." "Lastly, whilst this programme has been created in essence to reform a particularly unsavoury individual, this programme could be extended to other boys who might be deemed to benefit from such treatment. So please try to learn from this example, and avoid a similar fate." Matron Janice paused a moment, then turned to the soppy girl. "Sissy, come forward and introduce yourself," she said rather firmly. The strange girl rather hesitantly stood up with a crackle of petticoats. I could hear a strange whine coming from her, and I think she was crying. The Matron rather crossly stepped over to the trembling girl and reached for some wipes from her pocket. A little roughly she wiped the girl's face whispering something about "pull yourself together" and "waterproof mascara," and something about "consequences." She took the girl by the hand and led her to the rostrum. There was a few more buzzes about something from some of the boys, but I still didn't get it. Matron Janice pulled the microphone over to the girl's face, and switched on the equipment. Not everyone could boom out like her and the old VP. The girl's trembling fingers took a sheet of folded paper from out of her clutch bag. She was in such a state she was about to drop the bag, before Matron Janice rather abruptly snatched it from her, then sat beside acting principal Darlene, the poor girl's handbag sat on her lap like a trophy. "Head up, and speak up dear," she called to the girl, "just like we practised." The sad girl lifted her head for the first time. Her face wasn't ugly, if not exactly classically pretty either. She seemed to wear a lot of make up for a girl of her age, heavy eye make up, and shiny bright pink lipstick. Her face was oddly familiar. I wondered if I'd seen her on one of the rare visits into the community, but felt sure I'd remember a girl who dressed like her. We could hear her stressing and breathing heavily through the microphone. "I did something very stupid and very bad," the girl began reading from her notes her voice shaky and oddly shifting in pitch. There was a slightly familiar tone in the voice which unnerved me a little. There were now audible gasps amongst the boys. No it can't be I thought to myself. No way that's Jesse Cotton. She's wearing a proper dress, and petticoats, and girl's shoes and make up, even her hair looks like a girl's, and Cotton's hair might have been a bit long but it wasn't blonde for god's sake. "Modest tones," chided Matron Janice at the poor girl from her chair. "I used to be Jesse Cotton," the girl said now it a softer but strained sweeter voice. "Used to be, because I lost the right to a boy's name," she added choking a little. The assembly hall was in uproar now. I heard calls of "no way" and "oh my god!" "Boys, boys, quiet and listen to what Sissy has to say," called the new acting Principal in remarkably calm tones. The boys hushed a little but she surprisingly did nothing about the continued murmurings and whisperings. "Until....until I can prove myself worthy...." the creature before us stumblingly continued from its notes... "I have lost the right to be a boy. I'm not worthy to be a girl either. However my assignment and punishment is to try to be the epitome of a girl that perverted men like I would have become would mistakenly imagine women should aspire to." The creature stumbled over the words epitome and aspire, since clearly they were the words of Matron Janice or the acting Principal Darlene. "But...err....however....the Matrons have decided that for the period of my...my instruction...I am allowed to adopt the terms of 'she' or 'her.' In fact for the foreseeable future I "must" only be referred to as 'she,' 'her,' or my new name..." She or it audibly sobbed now in self pity... "or my new name "Sissy." A few ill suppressed giggles from the less sympathetic boys. "If at the end of the term I sufficiently demonstrate my willingness to learn my lesson, only then will I earn the right to regain my former male title. Should I fail...then...then... I solemnly swear to do whatever more is asked of me to rid myself of my former bad character." The creature looked imploringly over to Matron Janice to confirm if her utterly humiliating ordeal was over. "Thank you Sissy, now run along back home and get your pretty aprons starched and ironed, you have a big day tomorrow young lady," she said to the poor creature in tones reserved for little girls or the simple minded. A lot of the boys laughed at the aprons remark. I felt a bit sorry for the poor sap, but part of me too was disgusted at how a boy could let himself be treated quite like that. The Sissy did an odd sort of bob to Matron Janice, and then to Darlene, and turned on her heels and went out through the staff door, her chest heaving with tears I think. Matron Janice called us to order again. Her face though beamed with pride that she had truly shocked and surprised us. She went on to elaborate in more detail exactly how Sissy's "programme" worked out, and how we should treat "her." Jesse Cotton had obviously seriously rubbed them up the wrong way because I'd never known such attention to detail in one of their cruel punishments. Worst still I knew almost for sure the poor kid had been framed up. Whatever, they'd forced a full confession out of him and now that poor sucker was in for such a pretty horrendous time. Even when his punishment was over lots of boys will never ever let him forget he spent a term flaunting about in make up and dresses. Anyway the details roughly were this. As the poor Sissy said, he, well formerly "he," will be referred to as she or her, and only ever called Sissy. That's the rule for both boys and staff. "She" stays in dresses until the end of term when "her reformation" will be tested and reviewed. If improvement isn't sufficient then the programme will be "stepped up a gear" for a further term and again reviewed. Stepping up a gear from flaunting about in petticoats and dresses and girls hair and make up all day is going to be a tough call I thought. Sissy's "home" is at Matron Janice's staff house where she has "all the necessary features and facilities that "her" programme demands." Sissy has been withdrawn from all normal work and lesson schedules. Workwise she is assigned to staff, and will "fulfil roles suitable to her improvement." Tomorrow morning for example "she" will be assigned to the catering staff and will fulfil the new role of "breakfast hostess" until further notice. What that job means I didn't know. Her lessons will be "customised" to her new position. In most cases supervised by Matron Janice herself. If Sissy is ever to be cured of these "distorted male views" then "she" has not only to fully co-operate and participate in her fulfilling her role to the best of "her" ability, but she also has to learn to "head on" embrace the shame and humiliation of her situation. There will hopefully come a time asserted Matron Janice "when she eagerly accepts every new aspect of femininity she adopts with open willingness and a shame free knowledge that the false conception of losing any false male dignity are far outweighed by the benefits of a total and unresisting acceptance of her heightened feminine status." That is her only true path to her cure she declared. I'm not quite sure what all that meant, but we boys were told in no uncertain terms that we were to treat Sissy "just like a girl" or feel the consequences. Sissy should look and act like a girl too. Any boy that successfully reported an infringement from Sissy, where she was "less than ladylike" would be amply rewarded. Snitching on "untouchables" was the hobby of a number of sneaky boys, and they earned better work schedules, and special treats by being snitches. That kind of boy would guess the rewards would be even better for snitching on the new Sissy, because he'd obviously really pissed off the Staff. The poor Sissy better be on his guard. I made up my mind to warn him as soon as I could, even though it sickened me a bit to see how he'd let himself be treated. Eventually Matron Janice's explanations came to an end, and acting Principal Darlene dismissed us. The rest of the day was dominated by talk about the Sissy. Lots of the guys thought it was funny, I wasn't one of those anyway. A lot were disgusted, and though I stuck up for him a bit, I was in my heart a bit disgusted too. Some of the guys who were near the front of the assembly hall said they could actually smell girly perfume on the Sissy. I suppose with the make up and stuff they might have sprayed the poor kid in scent or something. At break Cooper was holding forth in the playground. He was right at the front of the hall for the special assembly he claimed and could actually see right up the Sissy's skirt. Cooper was a big mouth and I didn't like him, but he had all the boys around him listening. "You know what I saw up that effing skirt?" he crowed. "Actual pink frilly knickers...he was wearing pink lacy effing panties!" Most boys laughed deliriously. I wasn't having it. "Don't be stupid Cooper. You're a liar. Why would the Matrons bother to put him in girl's knickers nobody would see?" "Well I saw them Dale!" "Yeah right. You see a lot of shit nobody else sees too." Cooper glared at me a moment, we had history, but he didn't have enough of his close buddies around him to pick a fight. "Well, I saw what I saw," he mumbled and drifted off. There was speculation too whether Sissy's hair was a wig or not. I thought it was a wig but some guys came up with some compelling evidence that it might actually be the poor kids own hair. Firstly when he first came here his brown mousy hair was kind of long, he'd come from a distant community and I guess and in some districts guys had longer hair, or so I'd heard. Maybe it was because the Matrons were preoccupied with the problems with the Principal but I was surprised that for the few weeks he was here they never packed him off to have his hair cut. Before he was orphaned Joe Barnes said his Mother was a hairdresser and he reckoned that Cotton's hair was long enough to be cut into what he told us was called a "bob." His Mum had done it for his sister and he reckoned her hair might have been even shorter then "the new Sissie's." And it was "dead easy" to dye hair blonde he claimed. Of course he'd "stab the Matron's before they gave him a Sissy hair cut!" Anyway next morning I had chance myself to check out Sissy's hair myself. Before breakfast we were all told to wear our name badges before queuing for the refectory. We normally only wore them at the start of term or when there were visitors arriving, or new staff starting. Usually it was a bit of a jostle to get into the building. Today I could smell actual bacon, so we were in for a special treat. This would normally be the cause of a mini stampede but Matron Clare had us orderly, if impatiently, entering the refectory one at a time. When it was my turn to enter I realised why we were being directed in single file. Just inside the door was stood poor Sissy. She, he, it, whatever, was in some kind of black silky dress puffed out with petticoats, and she wore a really girly lacy white apron, and white cuffs on her short puffy sleeves. I saw her tired made up eyes look over the name badge of the fairly new guy Dwayne Bright who was directly in front of me. "Good Morning Master Dwayne" she said in that sickly girlish voice we had first heard yesterday. She did that weird bob at the knees, and handed him his cutlery. Bright seemed a bit startled, but grabbed the cutlery off the poor Sissy, and made haste to the queue for the food. Sissy's head bowed a little when she saw me. She, he, obviously recognised me and was ashamed. The Sissy did the little bob anyway, which Jennings later explained was called a curtsey, "it's what maids used to do in the olden days" he said. "Good Morning Master Dale," she said, a little hoarsely now, looking at my feet. He handed over the cutlery wrapped in a paper checker napkin. I noticed that his fingers weren't just painted with red nail varnish, but the nails were filed into long ovals like a proper girl's. "Head up Sissy," called Matron Janice from over on the staff table where she was obviously keeping an eye on the poor sap. Sissy raised her head and he tried to look blankly at me as I took the cutlery but I could see that under all that make up those eyes were full of pain. I took the opportunity to check out Sissy's hair out of curiosity. A tiny little lacy cap was pinned into the blonde "bob," but the way the hair naturally swayed when Sissy's head moved made me realise it was actually Sissy's own real hair that had been dyed and cut so girlishly. I felt deeply sorry for Sissy at that moment, even though I failed to see how a boy could let the Matron's do something like cut and dye his hair like a girl. Anyway my thoughts soon turned to the feast of real bacon, sausage, and eggs before us. This was a really really unusual treat. We were all sat impatiently waiting for one of the Matron's to say a few "words of motivation" then we'd get stuck in to this feast. All excepting the Syke's brothers who were chewing on something they'd already sneakily snaffled from their breakfast, or somebody else's breakfast probably. It was Matron Janice who stood to say her words. To our disappointment she didn't get straight to the "motivation of the day" but made a small announcement. "Each morning now Sissy will be your breakfast hostess...." A few ill suppressed titters from some of the boys. "....If you need any sauces, salt, clean napkins, or whatever, please simply call 'Sissy!' and she'll come to your table and you can tell her what you need. You are now forbidden to leave your tables now except to return your tray and leave the refectory. Sissy is here to serve." "The motivation words today are 'to serve is to obey.' Begin your meal boys!" We didn't need a second invitation and the scrape of knives and forks attacking the plates was a joy to hear. For a while nobody called Sissy for anything, and I was a little proud of the guys not playing the Matron's nasty game. But I thought the best of the guys too soon. It had to be one of the Syke's didn't it. "Sissy I need ketchup," he called in a mocking sing song voice. Matron Janice called over. "You just simply call 'Sissy' Kevin, she'll ask you what you need when she gets to your table." "Now hurry along to Master Kevin's table young lady, he's a growing boy," she called to the poor kid, obviously intending to humiliate him even more. The Syke's were at the table opposite mine, and even above the scrape of cutlery I could hear the clip clop of the heels she must have been wearing. I also felt the waft of flowery perfume as he passed behind me, and the faint crackling of petticoats. I looked down as he, she, it passed, and he was wearing shiny black Mary Jane's with a little heel. He was also wearing sheer tan tights, which I hadn't noticed before, the kind of tights Matron Janice seemed to like to wear on her long slim legs. I looked up now to see what happened. Lots of us did I think. The Sissy stopped at the Syke's table. I felt for Sissy a bit because it must have really hurt to have the rotten bastards who framed you for all this shit to be the first one's to rub it all in. Sissy took a moment to compose itself. "How can I help you Master Kevin?" she asked in that sickly voice, and she actually bobbed that stupid curtsey thing in front of the little shit. "I'd like some ketchup Sissy, and make it snappy!" The Sissy turned biting her lipsticked lip in obvious distress. "Be polite to Sissy Kevin! And a please wouldn't hurt," called Matron Janice mildly. "Ketchup please Sissy!" called Kevin after the Sissy in a mock sing song voice. His odious friends obviously thought that was hilarious. "Now, now, boys let Sissy get along with her work," called the Matron much more mildly than a usual scolding ever sounded. We heard Sissy clip clop back behind us and heard Kevin Syke's sarcastic sugary thanks. Next Jenning's called for a fork. The dozy kid had accidentally dropped his and realised he was forbidden to get up to retrieve it. I could forgive him a bit for that. But after that half a dozen other boy's made more casual requests for sauce, or salt, and even a clean napkin! As we left the poor Sissy was at the door, and bobbed her stupid curtsey and bid each of us to "Have a lovely day Master Dale" or whatever. I couldn't bear to look at her as I left. Then I felt a bit bad and thought I could maybe have given the poor kid some kind of secret sign that I was on his side and was sorry for him. The chat amongst the guys that morning was a fifty fifty mix of raving about the awesome breakfast, and discussing the poor Sissy. The discussion about the food was pretty unanimous. That was the best breakfast we'd had in months. The discussion about the Sissy was more mixed. A lot of the guys still thought it was funny. Some more guys now were getting a bit more shocked about just how cruelly thorough the Matron's were being with him. "He was definitely wearing perfume, and proper women's tights, even his nails were like...like shaped and painted like a girl. And that voice they make him use is just creepy," said Jennings in a mixture of awe and I think a bit of sympathy. Lots of the guys weren't sympathetic, and called the boy a wimp, or a pansy, or worse. They'd never ever allow themselves to be treated like that. They'd rather die. I didn't agree with those guys there and then, even if part of me was still disgusted with Jesse Cotton for apparently so pathetically going along with the Matron's cruel games. Some of the guys wondered if Cotton was made to wear those Sissy clothes all day. I said I was sure they just dressed him up for our benefit. But Bright remarked that his hair would still look Sissy, and his nails, even in his normal school uniform, so he'd still feel pretty bad. He had a good point. Greaves said, "He probably even wears a sexy girl's nightie in bed," whilst doing an imitation of a sexy girl's twirl. I'm afraid I laughed at that too, but Greaves was such a clown. Sissy wasn't in the refectory at lunch. I was glad that he was saved further humiliation, but a little disappointed I had no opportunity somehow to show my sympathy, or warn him about the snitches. At our table, Jake Riley, who's a good guy and doesn't tell lies did shed more light on something we were speculating on. He was passing behind Matron Janice's place on his way to see Doc Keene for his asthma check up, when he saw a girl in a yellow dress hanging washing out in Matron's garden. He thought at first that it might be another Matron, since she was too slim for Matron Janice. Anyway as he got closer he saw the blonde hair and realised it was Sissy. She, he, it, was in a regular dress though, a bit short, but no puffy petticoats or anything. Sissy never saw him and he didn't call out. On his way back Sissy was nowhere to be seen, but he could see the washing line was full of Matron Janice's bras and pants and stuff. The poor sap had actually been made to hang out Matron Janice's flaming underwear in public. Later that afternoon, when I was on work duty, Farmer James needed somebody to hike over to the old barn and fetch a sledgehammer for knocking down an old picket that seemed not to want to budge. There were no volunteers, firstly because it's a long way back carrying a heavy hammer, and secondly, as a golden rule, unless there's something in it for you don't volunteer for anything. I suddenly had an idea and called out to volunteer to go fetch the tool, just as Farmer James was about to "volunteer" somebody at random. He looked surprised, but shrugged and let me go. "But don't dawdle," he called after me. Taking only a slight diversion I realised I could pass by Matron Janice's garden fence. With luck Cotton would be about and I could warn him about the snitches at least. As I passed the garden I was disappointed only to see only a long line of women's underwear in shades of white, pink, and black. So as I thought, Jake Riley probably had been honest about seeing the poor kid hanging out Matron Janice's under things. There was no sign of the boy though. I decided to carry on to the barn and hope for better luck on the way back. I found the sledgehammer quite easily. It was damned heavy. Even over my shoulder it would be a pain by the time I got back to the field. As I walked towards Matron Janice's quarters I did wonder about calling for Jesse Cotton from the fence. The Matron almost certainly was on the school grounds at this time of day. My nerve failed me though. It was too risky. We weren't told that we couldn't talk to the boy, but a sixth sense told me there would be some kind of trouble for him or me if I did get caught shouting for him. Anyway as I got close I could see the "girl" in a pale yellow dress that Jake saw. Presumably she was bringing in the washing. As I got nearer to the fence I could see from the slim frame of the supposed girl that it was Jesse Cotton. The dress was like what my sister would call a sun dress. Fairly short, and his skinny arms were exposed. The blonde bob was confirmation it was Cotton. He was carefully folding the bras and knickers like a real woman does before placing them very delicately into the wicker basket at his feet. I saw he was wearing cork wedge heeled open toe sandals and plain white tights. I suppose you could say he was dressed like a regular girl. I wasn't sure if that was preferable to the sissy stuff or not. Being there dressed like a normal girl when there was nobody to see it was even more pathetic in an odd way. He hadn't seen me. I got right up to the fence and put down the heavy hammer. I made a "pssh" sound. There was no reaction. The blonde bob swayed as he unpegged another bra from the line. I "psshed" a little louder. He looked up, his mascaraed and made up eyes looking in my direction. I waved him over. He hesitated, a white lacy bra dangling from his right hand. Even from maybe fifteen metres I could see his face colour up despite all the layers of that make up. His head bowed and he dropped the bra hastily into the basket. I motioned him over again. He hesitated and looked around nervously to see if anyone was watching. Slowly he walked over the grass in those wedge heels towards me. As he got close I could see under the exposed reinforced toes of his tights that his toe nails were painted the same shade of red as his finger nails. It was hard to look him in the face. Close up I could smell his floral perfume, and the tinkle of girly bracelets on his wrists as he nervously pulled at his dress. I forced myself to look up, and fortunately I didn't have to look him in the eye since his head was bowed again. "How you doing?" I asked stupidly. There was a silence during which I realised how dumb my question was. "It's...it's difficult," he answered in that creepy soft voice they enforced on him. "It's not good at all Dale," he said, his voice cracking as he tried to speak like a proper boy now. "Not good at all," he added his voice breaking a bit close to tears. "Yeah, yeah, the Matrons can be bastards, and you really pissed them off Jesse," I said sympathetically. "Stick in there man, it's just until the end of term!" I added encouragingly. He looked up at me and forced a faint smile. That was a little spooky him smiling like a girl in lipstick and stuff, but I forced a grin back. "Listen Jesse...." I said urgently because I couldn't "dawdle" there too long. "You'll get in trouble calling me Jesse," he interrupted in that voice now alternating from soppy girl to proper boy, as he struggled to speak normally. "It's just between us Jesse," I said. "Anyway, be careful, the snitches have been told they will be rewarded if they catch you doing something..." I hesitated, I couldn't say "unladylike" to him. "If...if that catch you not behaving properly. So so be careful." "Thanks Dale, I will." He smiled as best he could. "We're all on your side," I lied. A few of us are I thought. "Is there anything you need?" I asked automatically, and stupidly. "My boy's things back." We both laughed. "I better go," I said knowing I was in trouble if I lingered much longer. "I better too," he said, his voice almost normal now. There was nothing normal though about the slim figure, long slim legs in tights, and toes perched on wedge heels that tip toed back to the wicker laundry basket. I glanced up at the pristine white knickers hanging nearest to where I was stood. They were kind of small for Matron, and they had lace ruffles at the back, not really a grown woman's style. Then I noticed the tiny red "S" stitched into the front of the knickers, then a tiny red "S" stitched into the small white lacy bra next to that, and a white "S" stitched into the tiny black lacy panties beside that. I felt sick inside. I picked up the hammer and headed back to the field without looking back. I was glad I'd done the "decent thing" but shocked at just how far the poor sap had let himself fall into their trap. The next morning Sissy was back greeting us at breakfast. Sissy actually lifted up those heavy mascaraed eyes to wish me "Good Morning Master Dale." His "uniform" was like yesterday's but now in a shade of candy pink. I forced a thin smile back even though I couldn't stop wondering if he wasn't wearing that white lacy bra and frilly panties I'd seen yesterday, under all that stuff. I was disgusted to realise with near certainty that he was allowing himself to be dressed in something at least equally feminine and humiliating. Breakfast was the usual, eggs or porridge, so Sissy didn't have much to do, but some boys called her over just for fun I think. Or their idea of fun. I heard her pink Mary Jane's clip clop behind me a few times, with a waft of floral scent, a tinkle of bracelets, and a swish of petticoats. Afterwards I felt bad that I didn't once look up. It was confusing trying to be supportive of the kid when he disgusted me too. I did manage a faint smile as "she" wished us our "good days" as we parted. Her made up face screwed up a little in gratitude at my encouragingly smile. That was a bit creepy really, but I was glad I'd smiled at him really. He must be going through hell.

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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The hunting farm

The hunting farmSynopsis: Cody and Jenna rise and breeding a naked female livestock for hunting. The trainees of the naked animals with paintball-guns end up in a real business hunt.The story is only fantasy.By RotnebCap. 1Jenna gets married at her twenty years birthday with the hunter Cody in the spring and they settled down in his large family farm. Jenna had been accepted within her new family in spite of the fact she has been naked prey at the last championship. At this competition the...

2 years ago
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Theater sissy

This is a true story. No exaggeration, no BS. Hope you enjoy it.My ex girlfriend Tori and I had lived together for sometime. Our schedules were such that we had one day off together and one day off alone. I loved our together days but my alone days were porn days. And I LOOOVE porn.I would grab my case of beer, pack of smokes, a towel and head for the computer room. I would look up pics, vids, hop in and out of chat rooms. The whole nine. I was really getting into crossdresser vids at this...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

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