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WARNING this is part one of a multi-part Story that will include permanent extreme forced feminization, intense humiliation and forced sex acts, if you do not like this kind of story do not read. The events depicted are pure fantasy and have no place in real life. I am a complete novice author who has loved forced feminization for years, Cheryl Lynn is by far my biggest inspiration and influence but I also love Kate, Alice Trail and have borrowed ideas from them and other writers. -------------------------------------------------------------------------- Despite his families relative wealth Daniel McDonald was in many ways a typical American seventeen year old boy. The untimely deaths of his Mother and Father in relatively quick succession put him, as well as the family's business holdings, in the unusual position of being under the care and control of his only sibling his twenty two year old sister Kristen. Daniel lived in an expensive house in an affluent part of the West Chester suburbs with his sister Kristen and attended exclusive Jefferson prep- school. Daniel had a fair pale milky complexion standing at an average five feet nine with a slight but healthy body. He was inexperienced and lacked confidence with girls his current and thus far only girlfriend was Phyllis Stone. Daniel had known Phyllis as his next door neighbor his whole life and had acquiesced to be her boyfriend when it became clear the girls he felt he deserved to be with didn't even know he existed. Phyllis had a cute cherubic face but had a pudgy chubby physique. Not so fat that she was unhealthy but too much to explain away as puppy fat. She was sweet natured and good company in private giving Daniel his first kiss and spending much enjoyable time together. Two aspects of his relationships with Phyllis left Daniel agitated. Phyllis embarrassed Daniel immensely when in public often jeopardizing his attempts to become more popular. She valued her virginity greatly and would not go any further than kissing and light petting until marriage. She was a strong young lady with immense self-esteem and conviction but nothing about her activities, image or behavior could be considered cool amongst her peer group. She was President of The Schools abstinence club, a vocal school appointed LGBT ally and a lifelong Marching Band geek. In spite of his association with Phyllis, Daniel had managed to slowly break his way into the popular clique of boys in the school, his fleet footed performance as short stop on the baseball field that summer had won many of the jocks acceptance when he went back to High School that September for his senior year. The popular clique of boys insisted that to fully join their group he would have to complete an initiation, that first Friday night of the school term they were to take Daniel to the wrong side of the tracks and hire him a prostitute so he could lose his 'cherry'. From that Friday evening Daniel's life changed, the seedy motel he was in with the prostitute was raided by the police, he was charged with solicitation and possession of five grams of cocaine that he was holding for his team mates. Kristen was infuriated to receive the call that her younger brother Daniel was under arrest at the police station in the early hours of Saturday morning. They had never got on well and as Daniel reached puberty he was becoming increasingly a nuisance, his arrest would prove to be the final straw. Kristen found him sitting on the sparse bench next to the prostitute the Vice squad had caught him with. She was a bottled blonde lady perhaps in her early forties, she had certainly seen better days. Her hair was in a gigantic teased out dated style with black roots growing out of the blond and had her make up plastered on to hide a multitude of sins. Dressed in black wet-look leggings and a cheap looking strapless pink neon top its cropped cut showed a little bit of a pot belly and a caesarean scar. She had placed her cheap oversized faux lynx coat over Daniel's shoulders and was rubbing his back soothingly as he sobbed and shivered. "So this little fruit is your brother?" the Prostitute asked. "That's Buffy" the uniformed officer cut in "She's been in here more times than she can count but we felt your brother would be safer with her than the men we have here." "I gave him my coat, the little darling needed it more than I do, it's more than he deserves saying he couldn't get it up because I'm a 'gross old hag' and that his baseball team mates picked out the roughest looking call girl they could as his initiation? As if right! I think this little darling just happens to have a very unfortunate soft spot when it comes to the ladies. He can keep the coat if he's faggy in bed girls deserve a prior warning." Daniel was bailed quickly, the faux lynx still over his shoulders too dumbstruck to remove it and was pleased to get away from Buffy, he was utterly dejected he failed to lose his virginity, he had never seen his sister more angry and under the county's new zero tolerance drug and solicitation laws he was facing a likely term in Juvenile Detention despite having no prior record. There was a frosty near silence on the drive back home in the early hours of Saturday morning "you look ridiculous in that streetwalker's coat and you deserve to. Since when were you involved in drugs? You are very silly little boy who seems determined to drag our family's name through the mud. Hiring a prostitute honestly how could you do such a thing to Phyllis?". Kristen was a ball of anger, Daniel weakly attempted to defend himself but he was too emotional and dejected. The next day when Daniel was at school trying to find out how the rest of team managed to evade the police, Kristen met with a defense attorney Olivia Jackson. Olivia was a statuesque black lady, with sweet young face. Olivia was in her late twenties and dressed very professionally. She came with high recommendation from the family businesses senior legal adviser Elaine Goldberg. "I see the judge assigned to this case is Edith Hardwick, I know how to appeal to her to see she overrules the mandatory custodial sentence and hands Daniel a suspended sentence and community service. It's going to require a drastic change in image and lifestyle for the brat though are you willing to do that?" Olivia. "Oh absolutely he's become totally unmanageable since our parents died and mixing with the wrong crowd so I'm quite happy for his life to be completely overhauled but there is no way he could survive in Juvenile Detention he's a spoiled rich kid they eat him alive" Kristen clearly trusted Olivia immediately. As Olivia went over Judge Hardwick's preferences and world view, Kristen was amused and intrigued by the new life her unbearable little brother would soon be living. In a couple of evening's time Kristen had dosed Daniel with a sedative in the evening meal and had naired her brothers groin before applying the chastity device. That morning her allies in her brother's lifestyle change project had gathered to face him down on this pivotal morning. Finding Daniel's former Nanny Ms. Lawrence working with patients of Dr Munn, again recommended by Elaine Goldberg, had been a stroke of good fortune. Dorothy Phyllis's mother was all too delighted to agree to the marriage. After her husband had turned abusive and violent early on in her marriage she wanted to ensure her daughter had a domesticated husband she could control "I cannot wait to write the prenup" she thought with glee. Phyllis was elated at the talk of marriage and accepted their explanation of what would need to happen in the short term to keep her beau out of juvenile detention. Daniel awoke to find a very snug plastic chastity cage locked over his now hairless privates. He tore through the large family home searching for his sister boiling rage, stunned in his tracks he stood naked in the main lounge, he saw Kristen, Phyllis and her mother Dorothy, his Nanny from his infancy Ms. Lawrence and a young black lady he would soon know to be Olivia Jackson. Daniel was caught between trying to cover his privates and trying to unleash his tirade about what the device was. As he was swearing profusely at his sister, his long absent Nanny strode up to him and easily subdued him and man handling the naked boy and started to rain blow on his backside with her hair brush. Olivia and Kristen exchange detached satisfied expressions, whilst Phyllis and her mother giggled somewhat self-consciously. "Daniel that device is your chastity and it is staying on until your wedding night to Phyllis. I've made all the arrangements with her mother you have no say in the matter," Kristen spoke firmly. Daniel was dismayed to see his hated Nanny back in his life, the chastity belt was an injustice he couldn't begin to comprehend and the thought of marrying into Phyllis's family stunted all his future hopes and ambitions. "There's so much i want to do in my life. I can't marry the only girl I've ever kissed. I don't want to commit to the girl next door and be tied down for life and there is no way her bitter battle axe mother won't interfere unbearably. An arranged marriage in America in the twenty first century it's ludicrous". "Following Olivia's methods is the only way for you to avoid a prison sentence and you might find some of the things we will need to change a little embarrassing and undignified but believe me you'd end up a whole lot more girly if you ever went inside" Kristen spoke. Olivia picked up the thread smoothly. "The Judge has a noted preference and sympathy towards sissy boys and transgendered teens. We will create that image for you. But for it to be believable you are going to have to be immersed in it and you are going to have to live it. Your clothes, your hair, your physique, vocabulary, mannerisms, interests and school curriculum and whole image is going to have to change. We are going to make the whole world believe you are a weak flamboyant flaming sissy it's the only way for you to avoid going inside." "It's too much I won't do it...there has to be other options please?..." Daniel sobbed. "This is your only course you little pip squeak your family money can't get you out of everything," his reinstated Nanny jibed. "It will only be until the trials over Danny and then with Mommy we can start planning our life together" Phyllis added with much kinder intent but it still was far from what Daniel wanted to hear. Daniel was so frightened over going inside he was thinking he would have to go along with their plans his obedience at least in the immediate future was sealed when Olivia Jackson said to him with perfect conviction "If you follow this plan I personally guarantee you will not be sentenced by Judge Hardwick to Juvenile detention." "Well we've really got better things to do," his Sister said contemptuously, "but your Nanny is going to take you with your new fianc? and Mommy in-law over to Phyllis's bedroom. For a big makeover and for you to work on your new backstory. Ms. Lawrence will be running your day to day life from now on she is fully briefed on what is needed and how to do it. Don't you dare think of disobeying your Nanny or going over her head to me." "Yes Daniel my sweet boy, after you got your parents to dismiss me just because I made you wear smart little Velvet suits and wanted you to take Ballet and tap dance lessons instead of the same old dreary Baseball game after game. Well after that I managed to find work via a certain Dr Munn, she will be your new Doctor by the way. She put me in touch with families where I could indulge my passion for making boys a lot softer and sweeter. These boy's parents were insistent that I curb the unruly tykes into girly little poppets. Unlike your parents who were so wrapped around your spoiled finger you cost me my job because I wanted you to learn the art dance? Well I know a whole lot more about making boys well-mannered now thanks to Dr Munn's associates and methods. I've already put together the beginnings of your new wardrobe and lots of accessories and so on." "But I still have to wear my Jefferson school uniform?" Daniel asked nervously. Ms. Lawrence smacked his sore red rump sharply "You will address me as Nanny Dearest whenever you speak to me! Yes you will be wearing the uniform but we can make lots of little touches and substitutions to let everyone know you not exactly batting for the boy's team anymore. I've also got the whole expensive set of girly mind and behavior mp3s left over from the last boy I worked for, believe me little Florence as he's now known doesn't need them he couldn't get any more feminine. You'll soon be getting very girly and I'll be enrolling you in as many dance and female comportment classes as I can find. Your new motto will be 'have leotard will travel' no more rough boys sports for you!" Ms. Lawrence chuckled heartily. "But Nanny Dearest?" Daniel nearly choked on the words. "This is just until the trial is over right?" "Oh yes of course" His Nanny said inconvincibly she seemed to forgotten all about the reason she had come back into the Bratty Boy's life. "I'll stand by your side and support you Danny, you'll be so cute if a little silly. I don't care what people think as long as we have each other" Phyllis enthused she was secretly thrilled at seeing her boyfriend, or any boy naked for the first time. Ms. Lawrence wrapped the naked boy up in a white soft toweling dressing gown and put a pair of pink fuzzy sheepskin backless slippers of his feet, they are an uncharacteristically fussy and girly item of his Sister's. Dorothy placed a ladies engagement with a giant cubic zirconia on Daniels ring finger fixing him with a confident derisive glare. His future Mother in law and his Nanny held both his arms firmly as they walked him out of the house on the crisp dewy autumn morning. "You can call me Mommy from now on now you're as good as part of the family, I know you think you're too good for my darling girl but I'll see to it that became the perfect little house husband. Prostitute indeed? Disgraceful! I used to work as a beautician and hairstylist before I married into money, my skills are perhaps a little rusty but I still have plenty of equipment and can't wait to have a go at making you into the neighborhood Sissy." Ms. Lawrence beamed with satisfaction she had clearly found a kindred spirit. Phyllis waddled and skipped her chubby frame giddily in front bursting with nervous excitement as Daniel was lead into the house and upstairs to her perfect girly goody two shoes bedroom. A room where all Daniel could think about as he entered it was how he failed to get any substantial action whilst tolerating countless disgustingly childish or girly films like 'Hello Dolly' or 'The Little Mermaid'. Phyllis's room was set up with all manner of equipment for hair and cosmetics. Products and equipment he had never seen his girlfriend use before were arranged neatly but copiously all over her vanity. The most conspicuous item was the old fashioned bonnet hair dryer. Dorothy placed a pink cape around his shoulders seating him by the vanity "I'm going to get busy giving you a brand new much more sissy appropriate hairstyle, it's a treat that you keep it long lots of hair to work with. While Ms. Lawrence will explain to your new lifestyle, interests and opinions you'll represent yourself to have in public. Phyllis listen closely dear you'll have to help your little hubby remember he's a femmy boy now and get working on his social media pages no better way to spread the word quickly!" Dorothy had soon washed Daniel's hair with a very girly herb infused shampoo and was applying a thick fouling smelling paste to his hair from the root outwards. Dorothy has wearing latex gloves and a little plastic tool not unlike a mini spatula humming merrily. Daniel's domineering Nanny stood close by silently daring him to disobey them. Phyllis was working on something studiously on her laptop with the dorky Disney Beauty and the Beast cover that had always embarrassed Daniel when she used it in the school library. As the paste was tingling Daniel's scalp unpleasantly, Dorothy plastered his face vigorously with creams. "There these should stop any facial hair growth, a sissy boy wouldn't be caught dead with a five o'clock shadow, not that you've got anything much at all on your face. You don't look like you've even started puberty and you think you can get into my daughters panties?" "I'll see he gets a good face full of that depilatory every night Dorothy and this second bleach cream is even better. It will make our little cherub all milky white, the judge wouldn't buy a sissy boy with a ball players tan!" Ms Lawrence chuckled as Dorothy hustled Daniel over to the bathroom. In the shower stall she got rid of what body hair Daniel did have down the drain with a less powerful normal hair removal cream, one that had come from the chemist not the horrifying supplies of Dr Munn. Soon she was washing the dye out of Daniel's hair over the sink. "Oh Dear, Oh Dear," Dorothy clucked with insincere annoyance at the results "Oh no I was going for a nice California blonde, I must not have used nearly enough peroxide, I am a little rusty darling." Ms Lawrence chuckling held a hand mirror up for Daniel to see the transformation of his hair it had blonde highlights in a sporadic uneven fashion but was mostly a lurid artificial orange that surely only an aging lady of questionable taste would dye her hair. "Well it certainly makes a statement," Ms Lawrence revelled in the look of horror on Daniel's face. "You're just about cute enough to pull it off I suppose. What do you think of your fianc?'s new hair color Phyllis?" "Oh gosh, it's going to take some getting used to. Daniel you do look pretty silly. I said we should have used a proper salon Mom!" Phyllis said mostly joking. "I suppose some of kids at school might tease you pretty hard but it could be for the best we need to do whatever Olivia says to keep Danny out of a juvie right?" Phyllis voice was full of doubt but it was clear she trusted her mother's judgement. "Because That's just not an option for a boy so soft and sensitive." "Dorothy if you'll get working on that cut and our sissy's make up. I'll fill Daniel in on his new back story as there is a lot for the little imp to take in." Over the next half hour or so Ms Lawrence broke down a new lifestyle and public image that was the antithesis of everything Daniel believed in and wanted to be part of. His subconscious was asking could this really be better than Juvie but the spoilt rich boy was too much of a coward to find out. "From now on you're going to insist on people calling you Dolly, you'll say it's because yours and Phyllis's favourite movie is 'Hello Dolly'. You'll identify your sexual orientation as bisexual but primarily attracted to men, that will fit in well with why you couldn't perform with that call girl." Daniel interrupted in his voice a curious mixture of distraught tearfulness and impotent rage "There's no way in hell I'm telling anybody I'm into guys, how in the hell does that help anything?." "You've already told everyone, it's on your facebook and twitter pages very unabashedly, thanks to Phyllis," Ms Lawrence stated smugly. "Yeah Danny it's not like you even have to do anything with men, because everyone knows your mine only but you're going to need to be kind of flirty and ditzy around the boys if people are going to believe your story, plus if you are properly girly they'll be too embarrassed to beat you up. Nanny says she has some great mp3's that will help you behave like that more naturally otherwise I know it would be super hard for you. I can't believe all your social media passwords were 'Erin Kennedy' I know she's like the hottest girl in school but I can't help but feel hurt. I've changed them now to something you would never guess so I'll manage them for you now." "As for how this will help keep you out of custody," his Nanny continued. "If you stand in front of Judge Hardwick dressed up to the nines like you will be, Dolly claiming to be 'straight' she will only see a little boy who is not facing up to reality or taking responsibility for his own actions. As far as school goes you'll be dropping out of all those advanced classes. Instead you'll be doing home economics and secretarial classes. Advanced classes will just make you look like some stuck up book smart rich kid and those classes will help you assist your future wife whether it's as her little housefrau in an apron and curlers or as her cute secretary in a twinset and pencil skirt." "But I want to go to a Princeton University like all the men in my family," Daniel uttered in dismay. "It's only until the trials over Daniel, it's still our dream to go University together. You're more than clever enough to make up the time, it will probably be a fun break for you to do some typing and learn how to bake some yummy cakes! I wish I could have a break from these college prep courses, still it will be worth it in the long run when I'm earning enough to support my gorgeous husband," Phyllis said trying to cheer Daniel up. Daniel was finding Phyllis's Pollyanna like ability to find the 'positives' in his humiliating situation infuriating as he thought "I'm not going to University with you or marrying you, you na?ve fat sow. As soon as the trials over and I can get this damn thing off my dick I'm dumping you for good." "Yes quite it's just until the trial is over. Until then instead of team sports you'll be in dance and gymnastics classes instead, if you're worried about how you will need to act around boys from now on those should be ideal as there's barely another male in them, certainly none of the rough boyish boys. Phyllis as a gay ally great has links with the LGBT society at school and I insist you participate as much as possible, you haven't always been too nice to gay students I hear, so it's only right you make amends. Judge Hardwick will look very favourably on involvement in gay social activities and campaigning for gay rights. As far as your other extra-curricular activities it's just Dance, Dance, Dance! I've looked all over the city and local area and I've got you lined up for dance classes just about every week day and hopefully some in-depth tuition on weekends when possible. You'll be learning tap, ballet, jazz, modern, traditional Irish, ballroom and interpretative. It's so wonderful how open minded the dance schools mostly are nowadays. You're enrolled in all girl's classes happy to admit a gender confused teen like you. The ballroom classes have no problem letting you dance the ladies role with male instructors and Dr Munn directed me to some Dance and poise classes especially for sissies. It was always my dream to be a dancer and you're going to be making up for lost time. You should have just gone to the classes when you were a little boy instead of pitching a tantrum to your indulgent parents. I may have gone a little overboard buying you dancewear but you deserve the best of everything. You still get your obscene allowance but you won't be spending it on sneakers, video games, New York Yankees memorabilia and lame attempts to buy your way into the schools popular crowd. It's under my management now and it's all going to be going on girly clothes, cosmetics, beauty treatments and romantic treats for Phyllis. Dorothy would you like to show Dolly her new do and beauty touches before we go onto the new school wardrobe and accessories I've got Dolly with this month's pocket money," Ms Lawrence said as she wheeled in movable clothes racks and cases from adjoining room. Dorothy spun Daniel in front of a mirror he had a largely chic girlish bob stopping just around his jaw line, that the ends tucked under in a slightly dated fashion. The bangs had been cut a bit too short and bluntly, Ms Lawrence thought. They were almost on the verge of looking like a punky alternative girl. This subtle distinction was lost on Daniel. "Oh no way I can't believe I have to go to be a boy with a goddam set of bangs, I've beaten up and humiliated many of my classmates for so much less," he thought despondently. "No please I look ridiculous please can you cut it way shorter and dye it a boys colour? And what have you done to my eyebrows and lips?" Daniel pleaded looking to Dorothy and Ms Lawrence tears blurring his version and compromising his speech. "It's supposed to look ridiculous after all you are a boy called Dolly, your future mother in law has done a wonderful job and this will make a great statement. You need to completely change your view point the more effeminate and laughable you look the better. I was talking to your Lawyer about what life behind bars is like for a wimpy rich boy like you and she said that you'd be claimed by a prison Daddy, who'd get the other prison Mary's to do your hair up in curlers, nails, brows waxed right off, the works. There's just so much time to kill behind bars and you'd not be able to stand up to them" Ms Lawrence was thrilled to both scare and mock the boy. "Gosh Daniel you really should have got a smart boys cut one of the ten million times I asked you to! Then there wouldn't be so much to work with! But it has to beat Juvie. Olivia was saying some of the weaker boys she's handled she didn't even recognize them when visiting them for their appeal hearing it sounds like Prison Beauty parlour is pretty hardcore" Phyllis was being flippant she didn't particularly want Daniel to suffer but wanted to communicate the seriousness of the situation and she was testing out the boundaries of being on the front foot of the new relationship dynamic. "You're being quite a demanding little Madame. This is the first hairdo I've done in years but if you're really good for your first full week at school as an out the closet Sissy, I'll trim it into a cute little pixie crop and make sure the whole lot is a nice natural blonde," Dorothy teased. "That could be for the best Dorothy dear a shorter do will make it so much easier to get his wigs and hairpieces on for his Ballet and Irish Dance recitals!" Ms Lawrence observed. "Regarding your brows and lips, Ms Lawrence says there is some discretion for students about the level of make-up allowed with no clear distinction made for male or female students, I guess when these codes were drafted, boys like you who want to raid their girlfriend's makeup cases were not known as an issue! So we thought to ensure you can at least always make yourself look a good way towards your new image we'd dye your brows a nice thick dramatic black and shape them up. Your lips have been dyed a wonderful cherry red and the stain has the added effect of really increasing the pout" Dorothy delighted in revealing the details of this extreme treatments to Dolly she'd never had advised them to a real girl but they served him right in her eyes. "You mean I'll look like I'm constantly wearing lipstick? This is going too far and my brows look like something out of a silent movie, let me go to the bathroom I have to wash this off" Daniel was so off kilter and distraught, his self-image was being assaulted from so many directions. "No Dolly it won't wash off now, I gave them a very strong stain, just in case your trial gets pushed back better safe than sorry!" "You're are so lucky that your Mother In-law is willing to not only forgive you but help keep you out of a prison but we must press on with getting you accustomed to your fabulous new school wear." "New school wear? I told you I have to wear the uniform like everyone else," Daniel stated with irritation. "Yes baby but there's wearing the uniform and then there's wearing the uniform. Your loving Nanny has come up with all sorts of wonderful twists that just wouldn't do for a real boy" Dorothy laughed she and Ms Lawrence were getting on like a house on fire. ... Before Daniel could try on the school wardrobe, Ms Lawrence had devised, his Nanny roughly forced Daniel into a special pair of high waisted control panties, which flattened his tummy right down, pushed his caged genitals back between his legs leaving a very flat girly front. The hips and buttocks had a subtle but effective amount of gel padding creating the illusion of a plump feminine butt and wider womanly hips. The first pants Ms Lawrence had selected were horrifying they were super tight girls pants in the school approved black but they were verging on leggings, once on they almost looked as if they were painted on and the seat of the pants lifted and separated his buttocks like a wonder bra does to a lady's breasts. Ms Lawrence and Dorothy watched Daniel's new bigger butt wiggle with great mirth as they made him strut back and forth across the boudoir. Phyllis watched intently too she had always been reserved and prudish when it came to physical matters but Daniel fearfully observed that the expression on Phyllis's hamster cheeked face appeared to be lust. Further pants were unveiled by Ms Lawrence some were high waisted, some were of a light crepe like material cut into absurdly wide legged lady pants with giant flares. Not one pair had even the notion of pockets and they all zipped and buttoned at the back, Daniel struggled mightily with this new development but Ms Lawrence and Dorothy were all too eager to get him in his most unmanly trousers. "I can't wear these to school wailed" Daniel crushed by the appearance his pants and padded control panties created in the full length mirror. "You most certainly can and will wear them, I've checked Jefferson's School uniform codes and whilst you might be the only boy fashion savvy enough to wear this type of trouser they do not break any of the uniform standards. Now onto the blouses that will replace those dull starched shirts of yours." There were a multitude of thin lacy camisoles and vests for wearing under his new school blouses. They were nothing any self-respecting male would ever wear Daniel thought as he surveyed the lacy nonsense his allowance had been spent on, tiny thin spaghetti strapped shoulders or ruffled laced shoulder straps that looked like they belonged on a medieval princess. They served no practical purpose and covered very little of his body with their plunging neck lines and cropped cut covering none of his taught flat tummy. "Can I please wear some normal boys vests who's even go to see these?" Daniel pleaded pathetic whilst his Nanny has buttoning up the back of an absurd tulle ruffled blouse that shimmered and flounced with the cowardly boys quaking sobs. "A Sissy In a Wife Beater can you imagine?" Dorothy roared at Ms Lawrence who shared in the joke. "Dolly, you have to give up all thoughts of being cool, manly, and conformist or having any form of self-respect or dignity until we get you through this trial. Your whole prior wardrobe is going to be sold at the school yard sale it will do you no good to be around those boyish things." "Sell all my clothes what? What about once the trials over?" Daniel fumed. "Once the trials of over your fianc? can pick out a whole boys wardrobe suitable for my docile obedient son in law," Dorothy smirked smugly. Phyllis had simply the worst taste in fashion as they all well knew "Oh goody I'll get loads of smart little boy suits, adorable bow ties, no more uncouth sneakers some nice shiny buckle strap shoes oh I can't wait it will be so good to have a fresh start with your trial and would be infidelity behind us!" "That all sounds wonderful Phyllis Dearie but let's not get ahead of ourselves, Dolly will need all your help with his current school looks" Ms Lawrence cautioned "I mean his out of school wardrobe is no major worry with Kristen passing on his Mother's whole extravagantly feminine wardrobe to the little fop and maybe some generosity from the shopaholic Trophy wife's in this neighbourhood he'll have more than enough frocks and frilly things to wear out of school to let people know he's an incurable sissy bitch." "I'm not wearing my dead moms wardrobe that is too much" Daniel's outburst was met by a slap from Ms Lawrence so hard it sent foundation powder flying in the air and Daniel sprawling to the floor onto Phyllis's kitsch fluffy mauve sheepskin throw rug. Daniel's knew little of ladies fashion but knew his mother sense of style had been extremely extravagant dressing something like a cross between a drag queen, a Princess and a Hollywood Golden Age starlet. It was all bespoke Furs, gleaming handbags, ornate pearls and diamonds and Chanel suits not to mention the gowns and cocktail dresses. The only thing Daniel could remember his Parent's arguing about was how hard she hit the credit cards, though there was always plenty of money to go around. "I can't dress like Mom?" Daniel thought as he snivelled as Phyllis comforted him and helped him to his feet "And the other wife's of the neighbourhood giving me clothes? They'll have a field day." Daniel had never been cordial or respectful to them and knew they would relish in dressing him up like a clown whether they thought he liked it or not "How can I face my old friends wearing one of their step mom's old party dresses?" he thought morosely. Ms Lawrence had selected all very fussy and ruffled blouses. Some had big short puff sleeves ending high on Daniel's upper arms "Those will look so good once Dr Munn gets rid of what muscle he does have" his Nanny had thought when purchasing them, the others had too much sleeve forcing him to flap and manoeuvring his wrists in the most girly of fashions. The blouses contrasted notably with the plain mans stripped tie, there was no way round that in the school rules. His normal school sweaters had been replaced with super chunky and fluffy mohair and angora knits that just had no place on a boy and made him looked like he was trying to make some kind of misguided fashion statement. "I got you two ladies blazers at a vintage shop, it was no trouble to sew the school crest on to them, so there's no way the school can object" Ms Lawrence showed him the first it was of a shiny tuxedo style completely incongruous to daytime school wear it too had ruched up bracelet sleeves that extend into giant puffed sleeves of generously cut suit fabric. That one was bad the second one was some-how worse it was an eighties vintage ladies power dressing ladies blazer with giant shoulder pads. Even Phyllis couldn't help laughing as he was put in that "God those shoulder pads aren't much smaller than the football teams, what a power dresser! You're supposed look like a Sissy not a jock!" "Wearing this gorgeous faux fur lynx Buffy gave you to school will be fitting justice! I'm sure you'd like to wear one of your mother's masterpieces but they are far too valuable for Nanny to risk letting anything happen to." "You need to look as silly, unthreatening, fluffy, and as vulnerable as possible and these accessories should help you do that. I mean you can't throw a punch with your hands in this giant fox fur mittens, just think of them as Sissy boxing gloves if that helps dear and with your hands constrained in his oversized fur muff you can't even do Sissy cat fighting with your nails and what about these big fluffy fur earmuffs I've got you them in every color going a little childish perhaps but so cute and they'll may filter out some of the meaner comments." "I can't wear all this fur it's just not right for a boy and its only September I'll be way too hot!" Daniel clutched at straws it was too much to take in and he already feared the wrath of his Nanny like he was an infant again. "Oh proper girly sissy's like you love their furs and you girlies can never be warm enough. It will let people know you are fragile and delicate and can't handle the cold like a real man. Your shoes are going to be fluffy too for your first fortnight back at the school you will be only wearing fluffy ladies carpet slippers and house shoes I've picked out for you it will be symbolic of the fact that you little missy are grounded, Judge Hardwick will responded favourably if she she's that we are punishing you already. After that we'll get you in Ugg boots to match Phyllis, won't that be cute?" Ms Lawrence asked mockingly. Again Daniel, knew very little of ladies of fashion, how that would change, but he knew they must be going out of style when his dork of a girlfriend caught on to wearing them and the only boys he knew of who would even consider wearing them were the campest of the camp. Nanny brought the clothing and The Sissy back to the McDonald house with similar ease, after teaching Daniel a night time beauty regime and dressing him the vintage peignoir gown and robe Dorothy had 'kindly' donated, she was much too fat for it now, he was put to bed in the incredibly lavish master bedroom on the satin sheet covered heart shaped bed. His late father hated it but his mother knew how to use her feminine wiles to get her way. Ms Lawrence put the Dr Munn mp3 programme first volume into his ears and switched out the chandelier mounted lights. She could not wait for his Sissy debut at school tomorrow and then his first visit to the formidable Dr Munn. Ms Lawrence filed Dorothy in on the effect of the mp3 and just what Dr Munn could do for Dolly. She had big plans, too big perhaps for Kristen and Phyllis but she knew Dorothy was a fellow man hater who she could trust.

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1 year ago
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Beach sex with my sister

My sister, Jean, was widowed a year before these events. She lived about 30 miles from me. I am Andrew (Andy, my sister called me) and I divorced my wife two years before this. I had remained single since then and masturbated when necessary. Jean and her late husband and I and my ex-wife had been campers. On one of my visits to Jean we arranged to go camping in Scotland. I had been told where there was a nice beach. I would take my small tent and camping gear which included a two...

Incest
3 years ago
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Two for Tennis

Two for Tennis - Episode One – Discovering the unexpected On Wednesday afternoon, I usually take off to play some tennis with friends at the local sports club. It’s a nice group, we usually have lots of fun and its great to get the body in shape and fit again. One of the girls I play tennis with often is Elin. Elin is a beautiful young blonde girl, unfortunately straight. She lives together with a hunk of a boyfriend and they are having plans to get married and have some kids. One Wednesday...

Lesbian
1 year ago
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PornWorld Shalina Devine Sara Bell Horny BFFs Shalina Devine and Sara Bell DPd by Boyfriends

Shalina Devine and Sara Bell pleasuring each other in the kitchen when Sara’s boyfriend Kristof walks in to find out what’s going on. Although he’s shocked at first, he quickly joins the fun and starts fucking both his girlfriend and Shalina. Minutes later, the three are fucking on the couch when Shalina’s husband comes home to find Kristof’s cock balls deep in her pussy. From there, it doesn’t take long for his cock to join the mix and together he and Kristof take turns DP’ing the two sluts.

xmoviesforyou
3 years ago
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Neighbors Panties

So.I've had a lust for my neighbor for a long, long time. She's a single mother. Slim, fit with dark brown hair. I remember when I first developed a taste for her. One evening I saw that she was hanging her laundry out to dry in the backyard, and what piqued my interest was her underwear hanging on the line, in particular, a bright red bra and a zebra a****l print one. It was kind of racy to me, for a older mother to still be wearing these sort of things. Because as far as I had seen, she...

2 years ago
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Jacking Off with a Buddy and his Dad

This is a work of fiction. Jack off and enjoy!Every school has one. At my high school, it was my buddy Cameron. He was the institution’s sexual braggart. He seemed to know everything about sex and was always happy to share his knowledge with anyone who would listen. He claimed the most popular girls had given him blowjobs and that he had finger-banged one of the star football players (even though the guy continually swore he wasn’t gay). Cameron said his parents let him watch all the porn he...

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