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Head To Toe Players Jack as Julie. Clair, Jack's boss. Helen, Clair's secretary and a host of supporting cast. Synopsis A remark. A thoughtless comment to a secretary, and a young man's journey begins. His beliefs needed changing, his boss said, and sometimes it's better that the lessons don't always come from a book. He needed to change and sometimes those changes are head to toe. Fact From Fiction: Irony is something that has fascinated me a great deal. Sort of like chance in some ways. I've experienced both, enough times in my life, to appreciate each in my life. Much of this story is taken from those situations I look back on with that sense of irony, wondering if it really was just chance. Story Chapter One It was a remark right out of the fifties, Clair thought. Something her father might say only the voice younger and much less authoritative as his had once been. More a condemnation, and simply because of a person's sex. One half of an entire species subservient to the other half for no other reason than being born female, and it sent a shudder down her spine. She was furious by the time she reached her door, and it showed when she stood face to face with the young as Mr. Cater. His smugness changed slightly to a touch of fear, and he automatically took a half step back to regain his space. A trick she had learned long ago when confronting men. Get into their zone or space, and they'll retreat automatically. A subconscious act, but they'll grow uncomfortable having done so. "Another great weapon in the feminine arsenal." her mentor, once said. It was, and it always worked, and it worked now. "Mr. Carter, a word if you please!" She said fighting the urge to knock him to the floor. She was an expert in kick boxing, held a black belt in karate, earned a dozen awards as a girl gymnast in collage, and could have done just that without chipping a nail. It would have also brought her an intense amount of pleasure seeing his face looking up at her. Although she didn't. "The one big advantage of learning self defense isn't always the ability to defend yourself, so much as that confidence you gain in knowing you can!" Her teacher had once said that. How true that was now as well, as she allowed the young man past her. She hadn't moved enough, making sure he had to again violate his own sense of space to enter her office. Clair had one more advantage that few shared and it was her anger. She'd long ago learned to channel her fury into a way of using it. That adrenaline rush, for her, the same as pushing the gas pedal of a car to the floor. Her mind sharpened instantly, as did her focus, as she eased her door closed. "Would you like to explain that remark you just made to Helen?" Ms. Evan's asked standing, again, too close to the young man she stepped up to. "Ma'am?" Jack asked slightly confused and very definitely intimidated. Scared suddenly, as well, given that her fury seemed directed at him for some reason. "Are you slow Jack? Didn't you understand the question? Do you need another moment to gather your thoughts?" Clair asked moving her face another inch forward. "No! I mean, no ma'am. I... She... She made me miss a fax? I missed it because she used the last of the paper in the printer and... She's just a secretary, and she should known better... And she made me miss a fax. I... I was mad. I'm sorry. I honesty didn't mean it." Jack stammered in hurried little flows of jerky words. He was in a desperate attempt to defuse this situation he suddenly found himself in. His own words adding more insult to that woman's injuries, and worse, fueling the fire Clair felt flair again over those words "...she's just a secretary..." She took a few seconds to work her fury into her statement, but she kept it in her tone: "Jack, I want you to go quietly to your desk, take whatever is yours and, if you don't mind, on your way out, stop by personal to let them know that I've fired you. I'll include a two week severance check with what we owe you, and ask that you honor my gesture of good will by also apologizing to Helen on your way out!" Clair said. "Fired? I'm fired?" Jack said in utter dismay and total shock. It wasn't that bad as remarks go. He was the fair haired boy around here. A rising star! To fire him for that remark, and to a secretary of all things was... It was inconceivable. "You really are slow in some things aren't you Jack?" Clair said allowing his show of emotions to satisfy her own in those seconds. She got that rush often when she was fighting her way to the top of most things to do with men. That look of total defeat, on her opponents face, a second before their resignation and, shock over it, set in. "Ma'am, I didn't mean it. I honestly wasn't thinking. Please, I want this job, and I will apologize. Immediately! Gladly! Honestly it was said out of anger. Please! Give me this chance!" Jack said as the realization of his dreams began to shatter. He wasn't so high up, so critical, so important suddenly, and that alone weighed heavily on him in that instant. So did the prospects of walking out that door for the last time. Clair for her part regretted firing him. He was important, and would someday, she had felt, sit at the large oak table with her other stars, or would have. It was a damn shame and she felt it deeply. Although not enough to save him. She had less than a zero tolerance for a male chauvinist pig. A term she used from collage for those professors that said, in so many words back then, that a woman should focus on home and family. Years of that chauvinism had been both her curse, and her blessing as she moved through the ranks. Half again as fast as her male peers after twice the effort. Learning to overcome that view by working harder than they did. It had worked, and she now stood at the top, and if this young man only understood what it meant to be a woman in a man's world... Chapter Two It struck her like a bolt of lightning thundering down to a point just before the crack and that odd smell of ozone. If he did know what it meant to be a women? If he stood in Helen's shoes for even an hour he'd soon appreciate that there is no such thing as "just" as secretary. There were two kinds of people, in an office setting, that Clair admired most. Two unique individuals simply because they were the truest first image of a company: That receptionist that people first saw; and, that secretary that always finds order in the midst of chaos. She hired the best, and paid them accordingly. That thought came and went and another formed. "Jack! I don't think you meant it on a conscious level, but I do think you believe it on a subconscious level. That's bad! That needs to change! However, I am going to give you another chance or at least offer it. I'm going to offer you an alternative to this being your very last day. An option, but only because you'll have to decide for yourself if you can do this or not. I believe it's for your own good. You might not agree but again that's going to be your choice. Understood?" Clair asked. "Anything! Yes, I understand! I'll do anything!" Jack said as his hopes rose. A second chance from a woman that rarely gave second chances. He almost hugged her. Almost. You don't really want to hug a lioness that's upset with you. However, his job was facing him again, and yes, he would do anything. "Fine! This weekend my staff and I are meeting for next quarter's strategy and numbers. You're working on some of the material, or were, as a matter of fact. Helen is working that day, as well, mostly keeping the minutes for my presentation to our board. I was going to bring in a temporary to help her with meals and refreshments. For the sake of that remark, I want you to be that temporary and work for Helen. Do you think you can do that?" Clair asked being cleaver not to add the rest of it. A decision in small bites is often better than forcing them to take the whole thing and risk choking. It would be humiliating, embarrassing, and well beneath what he thought his station was, but yes, he could understanding at some level her intent. A penance of sorts. Okay, he could do penance. He could do that for this second chance. Punishment with a touch of justice to the woman scorned Jack thought. A tough decision any other time, but not this time. His job was on the line. Jack had a way back, and he wasn't about to let it slip through his fingers. "Yes ma'am. I could do that. I'd be happy to." Jack said making it clear he was both thankful and more than willing to work his way to her good side. "Excellent. I had honestly hoped you'd swallow your pride, and accept this. I still believe you are an excellent contributor to this company, and it would have been a shame to lose you. I'll let Helen know, and have her arrange for your makeover. Frankly I think a day or two in her shoes, in a figurative sort of way, will do you a world of good!" Jack didn't miss a couple of things beginning with her hating to lose him. He knew without a doubt that he'd of been walked and still could be. He was also slightly confused over that "... in her shoes, in a figurative sort of way..." coupled with that thing about his "...makeover..." One meant in a figurative way, that other literal? "Ma'am?" Jack asked and paused. "Yes?" Clair asked. "That thing about a makeover? I'm not clear on that?" Jack said. "Experience Jack! We learn by our mistakes! We gain experience by doing things twice at times. Once to get a feel for things, and the second time we do it better. Always better after we've gotten that feeling for things. Although sometimes our education can't be simply taken out of a book Jack. You've learned some things about women. They're wrong! Now you must relearn some things Jack! The right things. Sometimes our education... what we learn, actually has to be experienced to understand it. Do you understand that?" Clair asked. "Yes ma'am. It's just that I'm still not clear on that makeover part?" Jack said feeling confused over what she actually had said with a touch of dread growing down in his gut. "Makeover? Jack, a makeover is a makeover? Oh, I didn't cover that very well did I? Okay, first of all don't worry about the cost. I'll pay all of the expenses for that and, of course, you'll be on the clock the whole time. As for what we tell people about that? I've got it! We'll simply say that you've lost a bet to me, and that was the deal we made if you lost. Should be more funny than not, and while your ego is going to be badly bruised, you should weather the storm fairly well. Questions?" Clair said holding on to her serious face as Jack's changed. Chapter Three Jack suddenly understood what she meant by all of that mumbo jumbo she'd uttered and why he was getting a makeover... "You are asking me to... You want me... Are you suggesting..." Jack was talking as his mind searched for a way to ask what he was thinking. He was thinking the unthinkable. The unimagined was being imagined. The impossible was suddenly a prospect. She couldn't be serious? It was a joke! It had to be! "Look Jack! Let's play this out! It could be the worse thing that has ever happened to you, and, yes, the most humiliating experience you've ever faced. Or... Or, and think about this for a second, or, it could be the most fun you've ever had. Sure, you'll be teased, chided, poked fun of and all of that, but they'll also think you've lost a bet! You are also, most of the time, a pretty gutsy guy and people know that. I know that! It's why I hired you in the first place. Besides, those guys that get wind of this will be a little jealous over the attention you're getting, and no one, besides you, me and Helen will know otherwise. "Look, I'll talk with Helen and explain it, and, trust me, she's a good person. The best there is at what she does, which is why I got so angry at you. It won't be much different than if you did this at Halloween, and, for the record, I can name five guys that came into this office swishing on that day. In fact, if I remember correctly, you were one of them. "So come on Jack! Take this like a man, and you keep your job. If that's not possible... Fine! Then I am truly going to miss you. I will miss you, but I have no tolerance for what you did and that is simply that. However, if I'm right about you, and I think I am, you'll do this for all the right reasons, and be the better man for it. "If I'm wrong... If I've missed the mark completely... Well, then I'm wrong, and you can say so right here and now. Say so, shake my hand, and we'll still part on good terms. I still think you are one hell of an asset, and no doubt will continue to be where ever you go. So, what's it going to be Jack?" Clair asked. Jack stood there in awe that he was still standing there. He did want this job to continue but this... This was so odd, so impossible to consider that it was shocking that he hadn't said no. Although he also knew, without a shred of doubt, that he'd be out of work a second, at most, after he did said no. "So I would be paying off this bet with you, or something?" Jack asked. "Exactly! Well done Jack! You would be paying big time and, if that's a yes, we'll walk out of here laughing, In fact, I'll say something appropriate like 'I warned you not to bet with me!' or something to that effect to get the rumors started, and you can walk around and start telling those you think need telling what just happened. I'm betting you'll get sympathy, some small amount of empathy, and a whole lot of kidding. The thing is this won't be during the week, and this meeting is scheduled for off site as well. It's just me, with staff. Staff only besides Helen, Jack. My staff most everyone that is going to be there knows me, and some of the offbeat things I've done. "Plus, two of those women-want-to-be guys that showed up Halloween are going to be in attendance as well. So, indirectly at least, you'll have company as it were. Again, if that is a yes and I'd like to hear it from you, then that's that. If you do say yes then I also want you to casually ask Helen for her forgiveness when she comes in, and give her your best apology." Clair said smiling for the first time. "So what would I have to wear?" Jack asked. "Something pretty Jack! You know, tasteful, functional, feminine and above all pretty. Something that you think I might like? Something you might like?" Clair said laughing and then added: "Do I take that's a yes?" "Yes!" Jack said dropping his eyes. "Oh stop that! Look, I have never read that putting a man in a dress has actually killed him. However, if this actually does kill you then I'll promise, right here and now, to make sure you're buried in something pretty! Okay?" Clair said laughing again. "Thanks!" Jack said feeling the stress pass. As bad as it seemed, at first, it didn't seem as bad suddenly. It was a joke, or could be and she was right... If he handled this the right way he might even pull it off as such. "Ready?" Clair asked. "No! Can I have a drink first?" Jack asked. "Sorry, that's for the clients. Don't push it either. We don't drink on the job, remember?" Clair said as she walked to the door and opened it. Chapter Four "Helen? Can I see you for a moment?" Clair said as she leaned out. "Yes ma'am?" Helen said coming in. Jack got a look from her, but it was just a glance and he deserved it after what he'd said, and he took his cue from Clair. "Helen! That remark of mine was totally uncalled for, and I apologize sincerely. Will you accept my apology and forgive me?" Jack asked. Helen smiled. She was born that way, and immediately said yes. Jack extended his hand and said: "Thank you." "Speaking of which! Jack dear! We've still got that bet to deal with! How about I make Helen in charge of this so she can get even a little?" Clair said. "Do I have a choice?" Jack said smiling, as much as he could, but only doing so because Clair was. Helen was looking on in confusion but she too was still smiling. "What bet?" Helen said feeling the mood lighten and noting she join in and ask. "Well, Jack here was so cock sure of himself that he made a little wager with me, and being the superior being that I am I, of course, won. So my young man here has to pay up. He's going to need some minor bit of supervision and assistance though in paying. Anyway, I thought it would be appropriate, since we are going to be meeting this weekend, that he be your temporary help as part of that wager. You game? I mean if you think he can do this sort of work that is?" Clair said in mock seriousness. "Jack? I guess? I mean I was going to have the temporary agency send over a girl just to help serve and clean mostly. Nothing really heavy duty. Yes, I suppose Jack could do that?" Helen said with a curious look on her face, but it changed to a smile as she added: "Sure, he'll do just fine. Won't be as pretty I suppose, but he'll do." "Oh? Well... Helen, on that note, and why I need your help... Actually Helen, he could be! He should be! Helen, listen, part of the bet is that Jack here is going to spend some time in my shoes, or your shoes, or a new pair like ours, and I'm not being figurative. That was part of the wager. Think you could spend some time on Thursday or Friday shopping with him for something 'suitable' to wear for this weekend?" Clair asked. Helen looked between the two, and in an instant began to laugh. "Really?" Helen asked as she tried desperately to compose herself. "Really." Jack said looking down trodden and very forlorn. "Yes! Yes I could. Oh, what fun. I'd be delighted. What's my budget?" Helen asked. "Well, don't put us at risk of going bankrupt, but don't put him into something dowdy or plain either. If I'm going to be putting this young man into a dress, then I'd prefer it meet with our companies image. Right?" Clair said. "Right!" Helen said between snickers. "Helen!" Clair said, and then added when Helen turned back to her: "Head to toe if you know what I mean?" "Oh! Oh yes... Yes I do know. How wonderful this is going to be!" Helen said with genuine glee in her voice. Then suddenly it was gone slightly as she asked: "Hair? Nails?" "Head to toe, my dear. Head, middle, front, back, hands and toes!" Clair said and then added after her own snicker: "Use my salon, and tell them I want the works! The works Helen!" "I will!" Helen said and then asked: "Is that what you wanted to see me about?" "No actually, but I'm glad you're in charge of this. Anyway, I want to go over what we'll need for this meeting, and I'm going to need some foils made." Clair said as she started to usher Jack out. Chapter Five At the door she said in a voice that could be heard to the forth of fifth desk away from her: "No backing down now Jack! A bet is a bet. You lost, and you owe, so go find yourself a pair of nylons and take this like a man!" Clair laughed as she closed the door. "What was that all about?" Stan asked looking at Jack as Jack walked over to his desk. "Would you believe it? I lost! I was sure I'd win this one! I still can't believe I lost!" Jack said. "Lost what?" Stan asked. "That stupid bet with Ms. Evans, and she's serious about me paying up!" Jack said. "How much?" Stan asked. "I wish it was money!" Jack said feeling his throat tighten. "What did you bet her?" Stan asked with a serous look of curiosity on his face. "I've got to wear a dress! I've got to wear a dress, and serve her and her staff this weekend. Can you believe that? A damn dress!" Jack said blurting it out. "Not on a good day! Man, that's definitely not a bet I'd want to make or lose." Stan said. "Me neither, but I did. Stupid, I know so don't say it!" Jack said walking back to his desk. He fell into his chair dejected and exhausted. It felt like an eternity had passed since he'd walked into Clair's office. He was still sitting there as the rumors began spreading. "...Hey, did you guys hear about Jack's bet... That bet with Clair... Poor guys got to wear a dress and serve her and staff this weekend! Can you believe that?" One guy said to another. "Damn! I'd hate to be in his shoes!" Another added. Several laughed, and the guy that said it, got the joke. "Right! I get it! His shoes!" There were pats of sympathy after a short while. Some teasing, as well, from both the guys and the gals, and it was just as Clair predicted. The girls offering advice like "he's a Spring and should stay with pastels" or "this style of nylons is the best for the money" and etc. The guys gave him sympathy, but a lot more of that teasing, which included a few remarks about perhaps getting together some night for say a movie and dinner? And, more importantly, which bathroom was he using since he was now Clair's new maid. Which also led to a question on what sort of dress he would wear? One of those maid outfits was what most of the guys decided on. One of those little shortie black things with the ruffled panties. Ruffled panties along with handcuffs and a whip. A whip and a few other things that brought tears to their eyes. By days end it had mostly settled into "a rib poking" kind of thing falling into the background fairly quickly as work again took priority. Chapter Six Which would have been that, except for the fact that Clair and Helen had still been meeting when Jack left. "Helen, beside the fact that he's lost that bet, and has to wear a dress, he insulted you. I don't like that sort of thing. So, I thought I'd also teach our young man an important lesson as well." Clair said. "Like what?" Helen asked not sure exactly what her boss meant. She did hope, but then again... "Like don't put him into something too adult! Try and find something a little cuter. Younger perhaps. He's small enough, and frankly, I think I'd like him to do just a bit more penance for that remark of his to you." Clair said and added: "Think you can do that?" "Oh definitely! In fact, I've got just the place! It's adorable. They've got some really cute things there. I shop there for my niece on occasion. He'll hate it!" Helen said. "Excellent. Now then, we're going to need two projectors, some flips charts and..." Clair said changing the topic as Helen started writing. Jack meanwhile was just sitting down at his desk after that exchange earlier with Stan, as Helen smiled. It was a wicked sort of smile. There are good days, great days and days like this one! Helen thought to herself as she left Clair's office. Her boss, aside from this weekend to do list, had just told her, in so many words, that she wanted that horrid little man dressed as a little girl. How can you possibly measure such things? Chapter Seven Life is good! Helen thought as she tossed her handbag on the kitchen table and picked up the phone. "Mary?" Helen asked at the end of the forth ring and a hello. "Hi Helen!" Mary said recognizing Helen's voice. "It's my niece again! This time something's special!" Helen said. Mary laughed. It was always Helen's niece and it was always something special. "What sort of special?" Mary asked and added: "And how big is your niece this time?" "Very, very special! And she's off the rack! I'm guessing a twelve, maybe even a ten plus. How is your inventory this time of year?" Helen asked. "For off the rack? Honey, a twelve or ten plus size gets you a large part of the store's inventory. This isn't one of your boys is it? I thought you retired?" Mary asked. "No, no! No, it's not for one of my boys and yes I did retire. Actually this is for a young man I work with. Seems he's lost a bet although I don't think that's the exact case! Anyway, I get to dress him up as a little girl, or something close, for this weekend, and thought I'd check with you first for his outfit." Helen said, and then added: "It's a head to toe outfit! Shoes, dress, undies, the works." Her flashbacks began with Mary's question and her own statement. How wonderful those days were. She was a teacher back then. A damn good one, and the school private. Private, and stepped in tradition. It had been seven years ago, and as clear today as if only yesterday. Chapter Eight She bought her first dress from Mary in nineteen fifty seven. She'd said it was for her niece then as well. Mary had just opened her little boutique. Of course that niece was Mr. Rice and she smiled. Mr. Rice had been very rude to her. Mr. Rice learned very quickly, but not too quickly, what being rude to Helen meant. It was so wonderful that face on him as he stepped into his first pair of panties. By the time Mr. Rice went on to his next grade level, he was knitting his own little booties and sewing like an expert on his own little dresses. That was her first "niece". Her second came along almost at the same time, then a third, and before long too many to count. All of her nieces, became the most well behaved of little boys. Perfect if one could imagine such a thing. It was also difficult, looking at those pictures she still had, to even imagine those were little boys. A few, and poor Mr. Rice was one of those, wore diapers. That was her ultimate discipline back then. Nice thick cloth diapers, pretty little ruffled baby pants and something very cute and very little girlish, that didn't cover either. How wonderful life can be she thought again. When the school closed, and she found herself out of work, she discovered another career. It was so ironic that it would be Mr. Rice again as one of her first clients. Same sort of dress she now knew he favored, and always with his little diaper and cute little baby pants under it. He might me Mr. Macho to his fellow officers, but he was hardly that when she tugged his arm towards the nursery. Of course, for a hundred dollars an hour, she tugged gently but firmly. Little Ms. Macho, like many of her special boys, liked it when she tugged gently and firmly and she laughed. She laughed, stopped and closed her album. She laughed a short laugh, shook those images from her mind, and cleared her throat before asking Mary: "So where were we? Ah yes, so no problem with finding something suitable then?" Chapter Nine Helen, if you were casting a movie, was your classic image of a mom, schoolteacher or favorite aunt. That woman who immediately made you feel like a kid again smelling of lilacs, and you could imagine, fresh baked bread. She even had that ever present beaded link around her neck to hold her glasses. Glasses that often sat above an ample bosom she covered with a sweater. She was the perfect role and it was, a role. It was one of many images that Helen had perfected over the years. She had an excellent schoolteacher look, a very stern nurse image, and a few others that she found that boys liked. However, at work she was your classic image of stability and efficiently. Mom, many called her at work, including Clair when she was feeling slightly vulnerable. Mommy to those young men she took time to discipline still but only part time now. Nanny also, when it was diapers, or even ma'am when those that deserved it, got to their little pats with her spanking stick. She wasn't sure yet about young Carter. She wasn't sure which sort he'd be. How he'd see her. She was sure it would at least be a "ma'am". She was positive of that. She was also wondering how long it might take for her to train him into those adorable diapers and ruffled panties. She'd like that. He wouldn't, but she would. She suspected not long. He was too small as men go. He was no doubt too small as a child as well. She was sure his mother had also taken advantage of that blond hair when he was younger. She would have. Then there was Halloween. Guys that wear dresses on Halloween will wear them other times as well. Guys that wear dresses at other times will wear dresses any time Helen thought. They just needed good enough reasons. Helen was always great at finding good enough reasons. Besides, she thought, Mr. Carter was a bit too prissy for a boy anyway. A bit too high strung as well. All perfect traits for that young man about to step into his first dress. It wouldn't be nearly as much frills as she'd like, because that would take him past this joke, or bet, or whatever it was forcing him into it. It would however, be pretty, and most definitely sweet. The rest could come later she thought. If she thought she'd like him that way. She suspected she would, but then again she always liked boys "that way". Chapter Ten Her brother was first, and a big part of how she learned both trades. Her mother was a teacher as well. Also a good one, and petticoat discipline back then was more than a respectable form of punishment. Although not the diapers, or those rubber panties her mother insisted her brother wear for his bed wetting. Helen always enjoyed those moments. Her brother's diapering at night. It made her feel superior. So to those times watching him being dragged into her bedroom, and even more so when he emerged so sweetly dressed. She was younger, but heavier than he was, so her stuff fit him quite nicely. Helen was also the boss of her brother, next to mom of course. Some ways more so because of that ever present threat of "telling". Of her telling his friends what he wore at night. Or what he wore when he was "bad". Helen's brother always did as she said. She had also thought he hated it. Only he didn't. It wasn't until later that he confessed to his naughty little thoughts in her pretty little things, and before long he was doing what she wanted without any threats. If you consider withholding some things as a sort of threat. She did that, at times, if he wasn't a good little girl or sweet little baby for her. Most of the time he was. When he wasn't, he didn't get his reward. That became true of her older boys, as time went on. It was those experiences she took with her when school closed for the last time, which was just before Madam Helen began. Chapter Eleven How silly to give birth to a baby, she would say. All that work so unnecessary, when you could have almost all of the babies you desired. Babies, she would point out, that are so much more well behaved than real babies. She would note this often, to those who also practiced in this art but hadn't yet discovered diapers as a tool. Mary didn't practice those arts although Mary knew of them. Mary was Mary and her dress shop had been there forever. So Mary had become something of an ally back then. A resource like none other when Helen walked into that shop for her next "niece". Mary and she hugged for the first time in a long time before Helen introduced her to young Mr. Carter. Of course Mary took the hints, and treated him like the poor soul he was. That poor man having lost that bet, but she knew better, as did Helen. Mary also knew that it didn't much matter the reason for his girlish things, because all that often mattered was simply getting them into them. Once that was accomplished the rest, as they say, is simply nurturing. Nurturing is natural and men adapt quickly to it Helen knew. So did Mary. You nurture a young man while he's wearing his pretty things, Helen said, and before long he's forgotten he's a young man. You nurture him carefully enough, and long enough, Helen would add, and he'll never want to be a young man again. "Spare the rod, but not the dresses!" Helen's mother often said as she sat her brother down in the living room in her best Easter dress. Helen had learned that as well, as a young girl, but carried it with her all of these years. She wasn't a psychologist, by a long shot, but she knew what boys sometimes dreamed. She also knew that all boys dreamed those dreams at times. Some only once or twice. Others more often. A few all the time. She wondered if Jack had those dreams? She was sure he did. She was also sure he would. Chapter Twelve "Now what are we up to?" Mary asked after Helen introduced Jack to her. His face flushed when he entered, had remained flush right up to that point. Helen had asked to bring him in after hours. She was sure it was the only way Jack would have agreed. "He's going to need an outfit! Something suitable to help me with a conference this weekend. Something pretty, but not too fancy. Cute and functional. Has to be functional. Do you have anything that can match those qualifiers?" Helen asked. "Of course! What's your chest size my lucky young man?" Mary said teasing a bit. Mary, like Helen, always considered this as hardly punishment, as much as a process of discovery for males. That this was nothing more than a little breach in their facades when they stepped into their first bits of finery. As Mary had once put it to a mother watching another fitting her son with a dress: "If every man wore panties, and those panties were truly panties, then we'd have little need for armies or sedatives." A statement she also made one day when she helped two aunts and with a struggling young man into his first panties. A unique situation for him, thanks to his aunts, and for Helen there as a consultant as she watched his struggles subside till they diminished. Diminishing was almost always proportional to the number of layers that covered him. By the time that young man had left he was a demure as any little girl in her own new dress. Jack gave his chest size and Mary nodded and a slight wink passed between them as she moved off towards the racks saying: "There are dresses, and then there are dresses. My Daisy Kingdom dresses all come with pinafores so we can mix 'pretty' with 'functional' quite nicely." Jack was in front of Helen and didn't see the smile on her face. He did note the dresses he was nearing and turned around still walking and said: "I'm thinking of something older. Adult kind of. You know what I mean, don't you Helen?" "Actually I do. That's why I think these will be more than suitable. The others far too juvenile. Besides, you risk spilling or mussing your little dress without that apron or penny on. Right?" Helen said in as cheerful a voice as she could muster. She waited only a brief moment before adding: "Of course if you'd rather not do this..." "No! I mean no, anything is just fine with me." Jack said in a sudden panic. He'd fully expected to be in one of the major department stores rather than in a little girl's boutique. Although, he wasn't really clear on what to expect, since he didn't know a thing about girl's clothes. Then again he'd seen that style dress on girls and none of them older than pre-teen and why he needed that sort of dress wasn't clear at all as he said: "Don't you have something... You know, less... Without that lace stuff?" "Honey, these ARE the dresses with the least lace stuff. Are you talking about the ruffles? Or the flounce? These?" Mary said holding the dress up to show him the flounced hem. Lifting the skirt also showed off the self slip attached and he almost stepped back, except Helen was there. Mary always loved this part when Helen brought in a niece or two. It wasn't often, but when she did she loved that look on their faces. Girls adored lace, ribbons, bows, flounces and ruffles. For boys the opposite was true. The more lace, bows, ribbons and ruffles the more scared they got. The more scared they got the more delighted the two women became. As Helen once said to one of the boys she'd walked in for his little dress: "Honey, if it's not pretty, then what's the point?" Helen almost said it again but didn't. Jack was having second, third and forth thoughts as the women picked out a couple of dresses they liked. Not what he liked, but what they liked. It seemed, to Jack, that what he didn't like or disliked didn't much matter. It also seemed that they liked what he didn't like more. Although Helen, off to the side of them did lift one up that made Jack want to faint. It was a dress girls wear for the ultimate like pageants and such. So Mary was right as far as these being least frilly, as Helen lifted that one, she said, was something to die for. To die over Jack thought. He was almost happy when Helen hung it back on the rack. He was almost willing to wear the one Mary settled on. Almost. Chapter Thirteen His first try on dress was a mauve, almost pink and very classic Daisy Kingdom. Large flowers from the bottom of the skirt up to that flouncy thing, to the ruffled things on the shoulders. And that was without that apron or pina... coat thing or whatever it was. His dress zipped up the back and was made snug with a sash but neither was touched. Mostly the ladies wanted to get a "feel" for the style. Jack would happily be willing to give both a feel if they liked. He thought this as they moved around him like mothers around a little girl picking at the ruffles and deciding. What the hell was the weekend going to be like he thought as he moved a hand away from the skirt, till he thought better of it given how that looked. He didn't want to touch the skirt, nor did he want to look like he was posing so he folded his arms. "That's not very lady like!" Helen said. Jack bit his tongue to keep from saying what he wanted to say. It would have been a lot worse than what had gotten him there. He was in his third dress, and this one just slightly frillier than the second, which was slightly frillier than the first. Start them in muted tones, less frills and a nice cotton broadcloth and work them up to taffetas and lace if they are new to this. That's was Helen's advise to a wife who had caught her husband cheating on her. Which in his case meant he would start in satin's and lace, only wearing cottons when he cleaned. "It's the slips and panties that gets them hooked!" Helen also said during a seminar on dominating men. "They have no parallels to those fabrics in most cases." She'd noted that then as she was noting it now. Jack's third dress wasn't a Daisy Kingdom, but styled like one and the slip wasn't cotton. It was a bridal slip of sorts with a layer of taffeta nylon before a layer of tulle before another of taffeta. Very pretty, very noisy and very little girlish. A wonderful dress Helen thought before letting Jack know she'd actually decided on the first. Jack's relief was obvious, although Helen had seen his legs moving ever so slightly under that second slip. She so loved boys, and those little movements they often made while they protested. Of course that was the dress he was going to wear, but why spoil it for him. He had settled on the plain one and he'd sleep better thinking that. He also didn't get panties or his "underslip". A girl wouldn't need one with that sort of dress, but a necessity for a boy and his first girl lessons. Girl lessons are much better taught with girl clothes she thought. So too those panties she'd bring with her. "First panties" were rarely store bought! First panties simply had to be special. Special panties Helen like making for her special boys. Special panties were always two layers, with one silky layer out, and the other one facing in. Panties like those always capture their imagination, she noted more than once, and their fantasies she added. She really did know a lot about young men, and smiled at what she already knew about this one. Chapter Fourteen "I think we're just about done. He'll need shoes, of course, and socks so lets get the shoes next, and I'll come back tomorrow for everything else." Helen said before turning back to Jack and asking: "Unless you'd like to come back with me?" Jack nearly hurt himself shaking his head no. Her coming back alone was fine with Jack. Getting out of there was his goal, and if it took a pair of shoes then so be it. "Those are definitely for little girls!" Jack said as Mary brought over a pair of shiny black patent Mary Janes. "They're perfect with that dress!" Helen said making it sound as if that was that. Jack's tongue hurt from biting it again. They left an hour and a half after they arrived. Helen would be back first thing. He would wear that light pink one with the pretty slip at the meeting. Another full slip under that. A soft chiffon petticoat over that, nylons of silk, his training bra, shoes and the ruffled lace socks he hadn't seen. And those panties... A bit much for a girl and just enough for a boy. The two women hugged. It had been a delightful evening as Helen noted, while Jack waited out front, I've still got to put his little panties together. Mary understood, made her promise a lunch soon and smiled over her sale. Another Little Miss Priss in the making she thought as she closed the lights. Chapter Fifteen "You'll have to remove those!" The large woman said as Jack hung his pants on another hanger next to his shirt. "Excuse me?" Jack asked getting ready for his waxing. "Those shorts. You can leave them on if you really need to, but you'll have to role them down. I wax for bikini's!" The woman said as she moved a stick in a cup of goo just starting to smoke a little. "I don't wear bikinis!" Jack said feeling slightly miffed that the women might think that he did. "Okay! But I still wax for one, so roll those or remove them, or go tell the lady at the desk you've cancelled your appointment?" The large woman said. Jack rolled his shorts down till he was wearing a bikini of sorts. That first application of, the almost too hot, wax scared him the most. His ouch came quickly but the wax cooled just as quickly. Although another "ouch" came with a "damn" added, a second later, when the woman laid down a strip f gauze before ranking it off his leg. An hour of "ouch's" and damns' went by, but you could drag a piece of pure silk across Jack's body and not get a snag. Which was exactly what that woman was going as she worked at touching up this spot or that. It wasn't exactly torture that silk part, and Jack might have spent more time letting her doing that but he had other things to do. He'd been given a complementary silk robe in pink with the Beauty Boutique logo on it as "all the woman got" for his makeover. A head to toe, for a woman, was a luxury, and an event. It was just as luxurious for a man, but they didn't admit it, and it definitely was an event, but not as it was for the woman. Jack had rolled his shorts down and back up again when his waxing was finished, and wore the robe for the first time to his mud bath and spa. There are words to describe what silk feels like on skin made smooth, but Jack avoided thinking those, and simply gasped a little. A couple of times, silently, and he was thankful for that robe and the fact he still had his shorts on. Chapter Sixteen Clair had called her most favorite beautician leaving strict orders that her young man would get the works. Whatever else, she said, she wanted him walking out dizzy, confused and as pretty as was possible. Not just pretty but knock down, drop dead gorgeous. And, as young looking as Mildred could achieve. Mildred had laughed. Sometimes, that wasn't possible, she'd said, but when Jack walked in that opinion changed. So did the wig she was thinking of after talking with Helen about his dress. If he looked older than ten she said, she'd quit doing this for a living. She didn't say that to Jack, obviously, and there was still two hours before they had to be at the conference site. He was waxed, soaked, rubbed, buttered, basted, pampered and whatever else he thought of as he went though the process of being feminized. He actually was slightly dizzy by the time they began working on him in a chair. There was a woman at his feet, another on his left hand, and Mildred breathing in his face as she began his transformation. The guy, and clearly that could be a discussion worthy of note, was behind him adding sprays of pink ribbon into a wig Shirley Temple would have loved. Jack hadn't seen the wig, nor did he connect it to him when he did. There were a lot of wigs on that large shelf that were being worked on. His only one of them and none of them he'd wear he thought. He hadn't seen his outfit either, because that was in a bag. A very large bag, and another, smaller, Helen said held everything. His new purse was filled by Mildred with some of the colors she was using or would be. His new panties, slip and that little dress waited as Jack slipped slowly into a different world. "We blend, color and cover!" Mildred said as she moved about his face with this thing and that. One of those things was mascara and she waited as he blinked, another she said was blush, then liners for his eyes, lips and some stuff for highlights that he forgot what it was called. His hands were softened, his fingernails lengthened, and his toes were a very pretty pink when he looked down. Why he had to have his toes painted since he'd be wearing socks and shoes was a question he would have like to ask. He didn't. He did panic when that guy moved in too close, but he'd always had a bit of a phobia about guys like that. He also panicked over his new hair that guy was holding. There were ringlets. Curls and ringlets woven with tiny bits of ribbon that fell right and left of those curls. Long curls, short curls, and those images of girls in the South came to him. The image of Shirley Temple came to him and he almost cried. He could use the back room to dress in Mildred had said, and said it again, as the group began backing off. There was five of them waiting for him to stand and admire their handiwork. Five of them, and that guy smiling at him made it worse. Actually it was his wink that mostly scared him. Guys don't wink at guys like that Jack thought. Chapter Seventeen A thought, which went suddenly away when Jack turned. Guys do wink at girls like that Jack thought before closing that path. He actually looked back to see "her" in real life before that second it took to realize she was he. Or in this case he was now most definitely a she. There was nothing of Jack left that Jack recognized. Not the eyes that fluttered at him or those soft puffy lips that glistened in the light. Nothing. He was stunning or she was and that confused him some as he kept bouncing back between those definitions. Clothes do make the man! Jack thought and sadly, he noted, they can undo the man just as fast. How can "you" turn "you" on he thought with a touch of dismay. It was like looking at this cute little fox, getting all hot over her, registering all of that and on the one hand, while your brain kept telling you don't go there. Don't bother. She's not available you idiot, because she's you. That little fox is you! Little fox Jack thought. He felt that twinge of panic again if that was possible, since that first twinge was still there. He was a little fox. Jail bait! He looked like jail bait. Heaven help me! He thought. What would everyone think? What would those guys think? It's one thing to spoof a woman, and dress like one, but a whole different thing to actually look like one. And he was a step or two past that. Guys don't look like that even on Halloween unless they are guys like that damn guy still smiling at him. "Ready?" Helen said holding back some of what she wanted to say. "NO!" Jack said. "Good. Your stuff is all set!" Helen said completely ignoring Jack's "no" and the tone he'd used. Chapter Eighteen "That's not the dress you said I was going to wear that's the one with the... I mean that's the other one!" Jack said fighting back that comment about the silky slip on that one. It was a slipper satin Helen had said. Jack didn't know what slipper satin was, but he knew the difference between that one and the cotton ones. He'd felt them both. "I know. It's just that this one was so much prettier!" Helen said. Mildred, meanwhile, was gathering up Jack's clothes and placing them in a bag as Clair walked in. Jack, according to what he remembered, thought he was riding with Helen to the conference and in a way he was. Only Helen wasn't driving. She would be riding with her little girl in Clair's company car. Jack also saw the panties and that was the last straw. "Not now, not ever, and that's that!" He said folding his arms over the pink apron. He looked like a little girl pouting and Helen smiled. "Hey! You guys ready? We haven't got all day?" Clair said on the other side of the curtain. Jack's panic was evident, and Helen held a finger to her lips as she said: "Almost, he's just starting to dress!" Helen took that second to hand Jack his new panties, and Jack didn't say another word as he dropped his and put that pair on. He'd gone this far and it was too far but that job loomed over him still. His job. He did moan or thought he did, and worried over that, and was thankful he'd left his robe on as he stepped into the panties and brought them up under the rustle of his tunic. Or kind of thankful since the robe moved over the back of those panties enough to notice. The rest he did by the numbers as Helen made him leave the safety of his robe for his bra. A little girl's bra and a "B" cup if those little bits of foam meant anything. Which seemed so as she helped him into it. His full slip followed. It fell to his legs touching them as it settled. It moved across his stomach a bit then again over the front and back of his legs. He understood the advantages of smooth skin in an instant. Smooth skin and something silky. His socks followed and sitting had a whole different meaning in those panties and that slip. His shoes next and Helen helped with his straps. The full slip to his calves as he sat, teased them when he stood again, and the bellowing petticoat was next. Helen cinched it before gathering his dress in her hands. She would have preferred longer time for these things but there wasn't much time. "Getting there can be far more fun than being there!" she liked saying. She did toy with his last slip a bit but that was for her benefit rather than his. Finally she showed him how to hold his arms up so she could guide those layers over his hair and a second later they too fell around him. Around him he thought, and this time Helen did close the zipper. It was that lining of the bodice over the slip that teased the bra against him and he had no idea how sensuous fabrics could be. The dress, once on, had caught his attention which, till then, had been focused on the slip touching his legs, which drifted from his thoughts on his panties. He felt like one of those steel balls in a pinball game and Helen was using those flappers on his thoughts. She was in a way and had racked a lot of points in her favor when the zipper closed The sash again making it more intense as Helen fashioned the bow. There were noises coming from all over him as well. Swishing no matter how slight he moved and a couple of times he did try moving a leg a bit. The pinafore was last and Helen almost cried as she moved back around the front. He was so cute, and she said as much as she lightly pinched a cheek then spent a second smoothing his foundation back. Chapter Nineteen "Hey!" Clair asked. "Ready or not!" Helen said. "Oh my heaven's!" Clair said stepping back while a hand clutched her breast as she added: "This can't be! That is not Jack! That is some pretty little girl you've brought in to pose as Jack! Isn't it?" Those, to Jack, were not complements, but he smiled in spite of himself. There was a wall that jetted out a few feet in front of him. That wall was covered in mirror tiles and Jack was filling them. Or that little girl that had been Jack was filling them. He could, on one level, understand Clair's surprise, because he was just as surprised. So too everyone else who had formed with Clair waiting, and that damn guy again. Like mothers and aunts admiring a girls first time all dressed up and wearing nylons of all things. Did they feel like this? Jack wondered. "Jack! Jack! Jack!" Clair said and then added: "If you'll agree to a sex change, I'll pay for it and then adopt you!" Jack looked at her in panic. "Hey, just kidding!" Clair said but then added: "NOT!" "I'll get his purse!" Helen said looking at Mildred who stood frozen with her mouth open. Mildred didn't get the cue but said: "Damn! I'm good!" Helen was looking at her and suddenly she caught on. "Oh, right!" Mildred added. She had put lipstick, blush and a tiny bottle of Lov's Baby Soft spritz in it along with a hanky, and on Helen's suggestion, a small feminine product still wrapped. When Mildred had looked at Helen in that odd way Helen said: "For later, when he opens his little purse to freshen his lipstick. Scares the hell out of them." Mildred laughed and nodded and said: "Scared the hell out of me the first time I saw one of those!" "Come on or we really are going to be late!" Clair said as she took the little pink purse from Mildred and handed it to Jack. Jack took it and blinked as a camera went off. Helen had been taking pictures all through the process. She promised they'd be safe with her, and he would have his own set. Jack didn't want pictures. Chapter Twenty Barny stood outside in his black suit and cap and immediately moved to the curb side door of the car to opened it. "Ladies!" Barnie said that without a thought. Barnie didn't know Jack, nor that it even was a Jack and added: "Hello sweets!" Jack didn't answer as he followed Clair into the large open area of the back seat. He did have enough forethought to lift his dress up before taking that step. A gesture Helen noted as he did so. "Gather your skirts my dear!" Clair said as Jack turned to sit. Clair took his purse so he could do so. Jack sat between the two women as the large black car eased into traffic like a large ship leaving port. The group from the beauty parlor waving as they pulled away and that guy blew him a kiss. Jack hated guys like that as he moved his legs just a tiny bit to the right and left. The large sedan moved away from the curb and everyone was waving. A half dozen bi-standers stopping over the crowed that had gathered. A couple waved. One woman said to another that she wished she'd gotten an autograph. Chapter Twenty One "Hi everyone! Listen, I said it was okay for Helen's niece to join us. She's going to be helping Helen. Sort of a Bring-Your-Daughter-To-Work kind of thing. Hope you don't mind. Julie honey, this is my staff!" Clair said as she came into the large rented conference room. Jack was taken back by the introduction and not sure what to do, or say, and as he was thinking about it Clair laughed. There were six in the room when they joined them. Four women and two men and the women immediately moved towards Jack "What an adorable little dress! Daisy? Right?" The first said. "Actually it's like a Daisy Kingdom but not!" Helen said as Jack was still trying to figure out what Clair was up to or what to say. He did nod yes to her question. "Okay! Folks, I lied!" Clair said. The small group growing curious over it. "Folks, this is Jack! You remember Jack? My young assistant covering our Europe accounts? He's paying off a bet we made. He's learning what it's like to walk in my shoes as it were. That was the bet. Of course I haven't worn those kind of shoes for a while now. Anyway, we've got a lot of work to do, so just try and ignore the fact he's a guy, and let's get started." "That's going to be easy enough!" One of the guys said. "Careful Brad! If I remember correctly you came to work in a dress not too long ago, and I'm betting you've still got it hidden at home somewhere? What was it? Oh, that's right! You were Dorothy weren't you?" Clair said laughing lightly. Brad's mouth closed hard enough that you could almost here his teeth click. "Right!" He said after a second. The rest, if they had comments left them to themselves as they moved to find chairs. Helen touched Jack's elbow, a moment later, causing Jack to turn in her direction, and motioned him to follow. The conference room had a small serving area to the side filled with a continental buffet and Helen whispered for him to go ahead and start making plates for the table. Jack with the deftness of someone with long painted nails took up a pair of tongs and began picking out iced fruit to a large dish as Helen did the hot roles. Clair stood at the head of the room and began writing on a wipe board her goals for the next quarter. The guys took turns glancing over at Jack until Clair cleared her throat. It was just a tad past eleven. There would be a brunch at two, and if the meeting went past five, Clair promised dinner. Helen and Jack continued moving about the room with coffee, sodas when asked, and snacks as the meeting fell into the agenda. Jack was almost forgotten by then - almost. There was still that stolen glance on occasion and a smile, without meaning, from the girls as the day unfolded. Those guys didn't smile. Jack wondered about the one that had been Dorothy. He was sneaking glances at the lace below the hem of Jack's dress. Jack was guessing he'd like that guy at the beauty parlor. Chapter Twenty Two It was a working lunch and Jack, along with Helen, helped the two from the hotel serve the salads and sandwiches that had been ordered. It was the first time Jack had a chance to sit when Clair insisted they both eat. Helen didn't miss the way Jack sat, nor had she missed how he handled long painted nails. He would have done his mother proud were he a girl, Helen thought, then smiled as Jack moved a bite of something past his lipstick. He would be so easy to train. She also thought. By dinner the trauma, Jack had faced in all of this, had faded some. Not completely as they filed towards the reserved table, but some. There was some fresh panic when Clair insisted he and Helen join them at dinner. A bit more walking between all of those tables, but by this time Jack understood how he looked how he looked was exactly as he looked. He was a little girl among adults and almost felt that way as the waiter did the honors of bringing his chair back before pushing it in again. Jack played his part hoping that by doing so he'd go unnoticed. That worked for most, but not for Helen. Most men, when caught looking like this get more masculine acting. Jack, on the other hand, got more feminine. Delightfully so. Helen was already convinced that Jack would make a cute, and very well behaved submissive. He was doing so well as a little girl, and those subtle moves he made when he thought no one was looking thrilled her as much as it had be thrilling him. Dinner, for the most part was uneventful and Jack had almost fully adapted before nature called. There was that renewed panic at being so public in such a private need but he wasn't about to go the little girl's room by himself. It was Helen who stood before Jack did. Chapter Twenty Three "Need help?" Helen asked. "NO!" Jack whispered loudly as he locked the door to his stall. They were alone, and Jack did his duty as quickly as possible. He spent a few minutes making sure his layers were down and a couple of those moments making sure his panties were up. "Freshen up honey!" Helen said nodding at his purse. "What?" Jack asked. "Lipstick my dear! Needs a new coat." Helen said. "Oh!" Jack said understanding suddenly, as he opened the small clutch he carried. It was right at the top, that feminine product Mildred had slipped in. Jack felt total panic seeing that particular item and not expecting it. He didn't even want to touch it, but had to for the lipstick. "Just in case!" Helen said. "Just in case of what?" Jack asked just as a woman walked in. A stranger. She nodded, but didn't go to a stall, instead, joining them at the counter. She too was freshening up. She smiled at Jack, and Jack smiled back but frightened and panicked over her seeing the applicator in his purse. "Go ahead honey and just do like I showed you!" Helen said urging Jack on to finish his lipstick. "I was so thrilled when my mother allowed me to wear makeup. Isn't it fun?" The woman said before moving her lips together. Jack nodded, smiled lightly, but felt faint and quickly found the lipstick. He twisted it up after taking the top off and did the same thing she did. They all left together but the woman told Jack he was very pretty as she spun off in a different direction outside the door than Jack and Helen. Desert was on the table when they returned and Jack performed a perfect combination of moves to gather his skirts and sit. It was fluid and Helen's heart fluttered. Chapter Twenty Four "Drop these guys off first then take me home James!" Clair said to her driver Barnie as he opened the door. It was almost ten. Jack let out a sigh that left the women wondering if it was relief or the things he wore. "Jack! You're the man!" Clair said giving him a high five before she ducked into the car. It left Barnie watching with a curious look as Jack returned her gesture. Helen almost patted his bottom when he bent to join Clair in the car. "Jack, you're off the hook! I've got a good start on the numbers anyway, so I'm canceling tomorrows meeting. You did as promised and I'm proud of you. You may also keep that outfit, and if you don't mind I wouldn't mind seeing it on Halloween again. I'll also pay for your makeover again. Anyway, that took a lot of guts and you've got my respect for doing this!" Clair said as Helen and he left the car. It was the look on Barnie's face that made Clair add: "Long story! I'll give it to you on the way home. If you don't mind turning around, and taking me there!" Jack stood with Helen in front of the closed beauty shop and a thought struck, as he remembered not gathering his clothes before leaving. "My stuff is in there?" He said to Helen. Helen looked concerned. "Okay, don't panic! They'll keep it for you till tomorrow. Look, come home with me and you can use my guest room. You've got to get out of those things anyway and I'll fetch your stuff first thing. I can drive you home after you're dressed." Helen said. "Thanks!" Jack said letting another moment of panic pass. He didn't know that Helen already had his "stuff" in her car. She'd put it there as he was getting his wig on. She'd do just that in the morning but she wanted this time left of the night as they walked to her car. Chapter Twenty Five Jack stepped into the silk bottoms of Helen's pajamas. They were pink and satiny but after that day almost masculine compared to what he'd been wearing. There was even a twinge of regret as that little girl ebbed away with Helen's makeup remover. His wig still sat on her bed along with his dress, slips and those dainties. He wouldn't mind keep those either, he thought, as he slipped Helen's light nylon robe over his borrowed pajamas. Helen was careful of the process she was working through, choosing those pajamas as part of it. The kiss when it came was almost motherly before she said: "You really were a trouper! I mean it. And as cute as I've ever seen. So be honest with me - please. Was it horrifying or a little fun?" "Both!"

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What's the difference between wrong and right? Who makes the distinction, and who gives them the authority? Most people would consider what we did to be wrong. A few would say that it was right, but mostly out of prurient interest. A few others, those who have been through the experience themselves and understand the emotional impact, would claim that it's both. My son and I are certainly in that last category.This story rightfully starts in 1987, when I was thirty-seven and Todd thirteen. I...

2 years ago
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Mistletoe

I’ve been reading a lot of stories here – a LOT – and I began to think I could write one just as well. This is as true as I can remember it, so it wasn’t hard to write. I put this down in my Advanced Lit class this week, but it isn’t the assignment I turned in. I had that one written already. , ) I hope you like it. Jericho saw the car rocking as he stepped out of the brush, and he knew what was going on. ‘God DAMMIT, Kacey!’ he roared. I could hear him, even with Bunyan’s knees up against the...

1 year ago
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Mistletoe

I've been reading a lot of stories here – a LOT - and I began to think I could write one just as well. This is as true as I can remember it, so it wasn't hard to write. I put this down in my Advanced Lit class this week, but it isn't the assignment I turned in. I had that one written already. ; ) I hope you like it.Jericho saw the car rocking as he stepped out of the brush, and he knew what was going on. "God DAMMIT, Kacey!" he roared. I could hear him, even with Bunyan's knees up against the...

2 years ago
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BLAME IT ON THE MISTLETOE

Blame It On The MistletoebyIgnoble©It was Christmas morning and, like so many other families all around the world, the Ferguson's had risen early to meet it.Still dressed in her bathrobe and carrying a steaming mug of coffee, Polly made her way slowly through the house as she tried to shake loose the cobwebs. Why was it that the older one got, the earlier morning seemed to come? She chose to take the long way around her suburban home to give herself as much time as possible to wake up, but...

1 year ago
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Redheads

Reddit Redheads, aka r/Redheads! A lot of men choose between either blondes or brunettes when it comes to the kind of woman they want. They usually don't even consider the more important dimensions to weigh out, like, for example, neuroticism, openness, conscientiousness, and, of course, breast size and ass-to-waist ratio. But there are a million things to consider when picking women, and I bet that a lot of you don't even think about red hair when weighing those things out in your...

Reddit NSFW List
2 years ago
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Under the Mistletoe

“Get upstairs and make yourself ready for me. Do I make myself perfectly clear?”I nod frantically as goose flesh pebbles over my skin. He stalks towards me; graceful, panther-like. I mean to back away but remain rooted to the spot. He grazes his thumb over my bottom lip, dragging his finger to my chin before gripping it firmly. Leaning into him, I catch a whiff of his woodsy musk as he places a feather soft kiss behind my ear. I stretch my neck over to the side as he takes my earlobe between...

Spanking
3 years ago
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Under the Mistletoe

Based Upon the Real Life Experiences of my Online Friend Paul Previously Published Under the Pen Name Marcia R. Hooper What's the difference between wrong and right? Who makes the distinction, and who gives them the authority? Most people would consider what we did to be wrong. A few would say it was okay, but mostly out of prurient interest. A few others, those who have been through the experience themselves and understand the emotional impact, would claim that it's both. My son and I are...

4 years ago
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Headmasters Punishment Part 2

Andrea stood in front of Mr Garvey, her headmaster felling ashamed, worried and slightly aroused. He had seen the video of her sucking a fellow six-form members cock in the school toilets and had threatened to expel her however it seemed it he was willing to offer the teenager another option and she didn't think she would mind the punishment too much. She stood in her uniform green blouse, bottle green skirt, white socks and black court shoes listening to him speak. "Andrea you are well aware...

1 year ago
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Toenadering

She looked at the white-and-gray metal box with the big round porthole. Her arms were crossed and her brow was knitted.He glanced at her sideways, a small curl of a smile hiding in the corner of his mouth, underneath the full beard she wished he would shave off.“You know, it isn’t going to explode, love,” he said mildly.He saw her already straight back straighten even further, like he his words had zapped her with electricity. She always stood so tall and regal. Others would say – and, in fact,...

Seduction
1 year ago
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Enge Stieftoechter

"...Hallo! Aufwachen!..."reisst eine Stimme Julia aus dem Schlaf. Als sie durch ihre verschlafenen Augen schaut, erkennt sie ihre Mutter "Peter faehrtt mich jetzt zum Bahnhof. Du haelst die Stellung! Ich komme in 2 Wochen wieder heim. Peter holt mich dann am Montag wieder ab. Pass auf deine Schwestern auf," sagte sie, bevor sie ihrer Tochter Julia ein Kuesschen auf die Backe drueckte. Dann verliess sie das Zimmer und kurz drauf hoerte man die Haustuer. So das hiess also, dass Julia (gerade 19...

3 years ago
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A story I found in one of my sisters old ntoebooks

I've tried not to change too much as not to ruin the original story, but I've placed the correct terminology in places where it was absent. After reading through it, Ive come to the conclusion that it would be more enjoyable from a female perspective. That being said, anyone can read it. Anyway, hope you all enjoy it. If i find anymore stories, I'll be sure to post them. Also, the story just ends. I don't know why, but it does. So be prepared for it.I had always heard that sex in an act of love...

3 years ago
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Headmaster

David, my husband has an older brother, Steven who has two sons, Charlie and Miles with his wife Karen. At the time of this incident, Steven was serving in the British Army based out in Germany, both sons thanks to the Army paying some of the fees, had been educated at UK boarding schools since they were 8 years old, flying out to see their parents at full holiday times, at other times we were their legal guardian in the UK and looked after them on the half term breaks. Charlie is 2 years...

3 years ago
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headmaster pt 2

You were bent forwards now, legs splayed, your ass and pussy only just covered by your tiny gym slip, but not for long. I reached forwards and drew the skirt up - a finger gently tracing along the line between your cheeks - and left it gathered around your waist. I heard you cry out as you felt yourself exposed to me. By now you will have realized what a tough headmaster I could be and you must have been more than a little scared as to what was to come next. I stared at you, stroking my cock...

Straight Sex
1 year ago
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Under The Mistletoe

This story is a work of fiction.It was Christmas time and ever since Stan had turned 30 he'd been holding his own little dinner with a small gathering of friends every 22nd of December, before they all had to leave to go back to their families to spend what could be potentially an insufferable few days over the holiday.Every year he invited the usual friends, Bobbi, Mark, Jack and Sam, and whoever they were dating at the time, especially Sam who never seemed to keep the same boyfriend for more...

4 years ago
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Under the Mistletoe

Yeah, it's another Christmas story. This one is short but sweet, sort of like those crappy two-inch candy canes they used to give you in grade school. Only without the crappiness. Under the Mistletoe By Tanto Nick looked around the room as his family milled about. It was the annual family Christmas party, one that Nick dreaded every year. He seemed to be the only person in the family who was older than nine but younger than thirty, so he never had anyone to talk or even just...

1 year ago
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It Must Have Been the Mistletoe

It Must Have Been the Mistletoe Belladonna "Look at you, baby," Yasmin said with a smile as she stepped into Noel's home to hug her friend. It had been months since she had last laid her eyes upon him. She was amazed by how different he looked in such a short period of time. Yasmin shook her head as she said, "You look so thin." "I can't hear that one enough," Noel beamed, placing his hands on newly slender hips. Noel had been shedding pounds since his gastric bypass...

2 years ago
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Under the Mistletoe

The sounds of traditional Christmas music, intermixed with more conventional party fare, filled the air as the employee Christmas party at Hanson Brothers Auto Mall entered its fourth and final hour. As company parties went, this one was better than most, despite the fact that it was taking place in the temporarily emptied showroom, as opposed to one of the restaurants or rental halls that most other companies in town booked for the occasion. Hanson Brothers was a fairly good-sized business,...

4 years ago
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My Body Stretched on Tip Toe

My body was stretched on tip toe, in my 541 dollar leather merciless heels. My wrists, becoming tingly and deeper pink reminded me of what he was going to do to me tonight. I heard the leather roughly hiss through the loops in his trousers, like a snake on the charge for hard won prey. I felt the air shift as his breath drew in and his hand swung the tongue that would taste my flesh for the next hour. Repeatedly, slices of humanity were branded into my flesh, striping my breasts, thighs, belly,...

1 year ago
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My Three Sons 58 From Head to Toe

{Caveat: This story happens on an alternative world, not the one of the original TV series.} My Three Sons Chapters 5-8: From Head to Toe The Year of the High Concept By Ron Dow75 5) I Thought of Bugs Bunny Cartoon Titles "That is not the style," Miss Helga, the young mod salesclerk in the wig department, told the 'much older' woman. "That 'do' is so 'don't', it's not even a counter statement." The beige blonde in the tailored tweed dress suit with the blue trim adjusted...

Humor
1 year ago
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DO YOU SELL YOUR TOMATOES

I saw this story online. I really liked it so I thought it was worth sharing."I stopped for coffee at DQ this afternoon. After I sat down I heard a guy telling the cashier that he’d have to pick his tomatoes tonight as there was a frost warning. He sat down at a table behind me. I turned and asked him, “Do you sell your tomatoes?” He smiled and replied, “No. I freeze them and eat them all winter in soup and chilli. “Okay.” I said, “I don’t eat them but my wife does. Sorry to bother you.” ...

1 year ago
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Redheads really are hornier

I'm sure most of you are familiar with the show "Manswers". One episode was questioning the hornyness of Blondes vs Brunettes vs Redheads. I've always had an affinity towards blondes, but have always been attracted to pale redheads, but had never had the pleasure of ones company. As most of you would assume, I thought blondes would be the hornyest, but Redheads were determined to be more horny and more sexually active! "Yeah right" I thought, "Bullshit". It wasn't long after I saw this episode...

2 years ago
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Headmasters Punishment Part 1

There is a hesitant tap on the headmasters door."Come in" Mr Garvey repliesAndrea walked in, her head is slightly bowed a worried expression on her face as she steps forward to hand the headmaster a note. He takes it and quickly read the contents while she stands nervously beside the door. Andrea looks down at her black shoes before bringing her gaze upwards to her white knee length socks, bottle green skirt and pale green blouse. He sighs and look up at her "Let me have it then" he asks...

2 years ago
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Headmaster aar baba

Head Mridul babu master besh khato manush, tar sashtho khub valo, mukhe gof ache. Age roj bayam korten, tai shorirta ekhono thik ache. Mathar chulgulo pray sada hoye gechhe tar. Ei school e mastari korchhen onek din holo. Sobai take khub valobashe. Kao ke kono din boka den na. Sobaike manush hotey bolen. Sobai tai bipode apode unar kachhe jai budhdhi nebar jonno.tini biye koren ni. Asoley biye korar somoy tai tar konodin hoyni. Aj school er bangla teacher pratimadevi amake ke nokol korar somoy...

2 years ago
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Headaches and remedies or how I nailed my sister1

Mom had started suffering migraine headaches during the divorce process. The doctors told her it was psychosomatic but it didn't help moms headaches. Sometimes she would be awake all night with a headache. The doctors finally prescribed a sedative that was guaranteed to let her get some rest. The first time mom took a pill for one of her headaches she sleep the entire night. She woke the next morning rested with no memory of suffering from a headache. From then on when she felt a headache...

4 years ago
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Headcheerleader II

Anyways we are here at college with the good life. I forgot to tell you how I got Jimmy the scholarship? You see as the high school season went on it was beginning to look like our team was going to make a run for the State title. We went on to win every game the rest of the season. We even beat that team that beat us in regular season during the playoffs. College scouts started looking at Jimmy and some of the other boys real hard. Us girls in the cheerleading squad were glad for our boys....

3 years ago
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Goodhead Farm Pt 04

Chapter 6: Honeymoon Fun In the morning we woke, snuggling together in bed warmly as we touched each other, her smooth skin and the fresh memories of the night before making me hard. We took a shower together, cleaning ourselves up, and she sucked me a little while we showered. I noticed a bruise forming on her cheek where I’d slapped her a few times, but said nothing except not to cover it, because it turned me on. Her response was a simple, feminine, ‘okay’. Afterward I got dressed, and she...

2 years ago
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Goodhead Farm Pt 02

Chapter 3: The Last Night That night at dinner, her mother dropped a bomb. ‘My daughter seems to like you very much,’ she said with a knowing look. ‘She has visited you many times since you’ve arrived.’ I blushed, looking at Candi for a moment, who blushed too, looking a little sheepish. ‘No, I haven’t…’ Candi started, but was cut off. ‘Don’t worry,’ her mother said with a reassuring tone. ‘I’m not angry. I can’t blame either of you for it. No man can resist the women in my family, we are...

1 year ago
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Goodhead Farm Pt 03

We were married a month later, a small ceremony, with an unusual twist. The prenuptual agreement she signed had nothing to do with money, it guaranteed that she could never accuse me of raping her, that she would give in to me at all times, obediently, as a wife should. Tonight was our first night in the honeymoon sweet, she still wore her bridal gown, her tiara, coming straight from the wedding. We entered the honeymoon suite and she kissed me quickly, on the lips, before rushing off to the...

4 years ago
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Goodhead Farm Pt 01

Chapter 0: Introductions Farmwork was always hard, and never harder than at this place. Every day for a week, by evening I was sweating like a horse, hungry, and horny. The woman who employed me here, Mrs. Goodhead, was a widow who lived alone with her 18 year old daughter. The husband had passed away a couple years ago, but they still hired staff to run the place. I fixed things, and when there was nothing to fix, I did farmwork. Every night the woman made me a good meal, and I ate with her,...

2 years ago
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Headshot

Copyright Oggbashan 4 July 2004 The author asserts the moral right to be identified as the author of this work. This is a work of fiction. The events described here are imaginary, the settings and characters are fictitious and are not intended to represent specific places or living persons. ************************************************* I was shot through the head with an AK47. It was a mistake. I was with the international press covering a war zone but not as the intrepid TV reporter. I...

3 years ago
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StreetHeadChroncles 1

There are many whores, hookers, prostitutes, and e****ts, but I particularly like lowdown streethoes. Toothless, cracked out, nappy head streethoes. It all started when I was 12 years old. Dallas,Tx 1982-83. My mother was never around due to her d**g addiction but I saw her everyday. In the mornings before school, I would see her out on the corner. Usually getting in or out of someone’s vehicle. I lived with my Grandma and everyone pretended like it didn’t exist. At the time, I knew my Mom was...

3 years ago
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Headmasters Revenge Chapter Two

Shooting pains seared down my arms right from the shoulders, down to where the cheap polyester tie still bound my wrists together behind my back. One side of my face was pressed to the cold floor and I could feel his cum drying and flaking on the exposed side of my face. He was sat in his chair, head tilted back, leaning on the wall behind him with a look of utter bliss on his face. I pulled my legs closer to my chest, too exhausted and humiliated to bother trying to get up. The creaking of his...

3 years ago
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Headmasters Revenge Chapter One

The day the letter dropped onto the doormat and I caught a glimpse of my old school crest a flood of emotions and memories hit me. Bending down to pick it up I swept the hair from my face and let out a big sigh. Trudging back to the kitchen I put the envelope by the kettle as I started to make a coffee. I lit a cigarette, inhaling deeply as I tore open the envelope and began to speed read through the letter. My shoulders relaxed as I read. It was just an invitation, for ex-students to return...

3 years ago
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Headshots

There was a knock at the door. You walk over and open it to see a young girl who looks as if she has just turned 19. "Hi my name is Stacy, I'm here for the free headshots that are being offered" says the cute brunette wearing clear plastic set of glasses. "Yes right this way" you say as you usher her into the studio. "Would you like a free photoshoot as well?" you offer her. "Are you sure? That is normally quite expensive." she replies "Quite sure" You say as you walk over to get your camera...

4 years ago
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Headmasters Secretary Chapter VI

The following day Liz awoke a little disoriented, not recognising the view from her window at first but slowly she realised that she was indeed in a lovely country cottage tucked away in a hidden corner of England and it was blissfully quiet.Nevertheless, her morning followed its normal routine of showering, breakfast and dressing, this time putting extra effort into her selection. Today was black lace underwear; push up bra, delicate lacy panties and suspender belt with black seamed stockings...

Office Sex
1 year ago
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Headlocked in Thailand

"Headlocked in Thailand" by MFXslave [interracial, Fdom, femdom, snuff, rimjob, cunnilingus, anulingus, killing, handjob, headlock, BDSM, bondage, assassin]David Argyle shook hands with his Thai business partners in the downtown Bangkok Head office after all the necessary papers had been signed. He had closed the deal in less than four hours. His superiors had expected several days, if not weeks, of stalling and various unreasonable demands.He called his New York office, quickly briefed them...

2 years ago
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StreetHeadChroncles 1

There are many whores, hookers, prostitutes, and escorts, but I particularly like lowdown streethoes. Toothless, cracked out, nappy head streethoes. It all started when I was 12 years old. Dallas,Tx 1982-83. My mother was never around due to her d**g addiction but I saw her everyday. In the mornings before school, I would see her out on the corner. Usually getting in or out of someone's vehicle. I lived with my Grandma and everyone pretended like it didn't exist. At the time, I knew my Mom...

1 year ago
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  • 16
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Headteachers Punishment

As I lay on the cold hard pale blue tiled floor of the school's store-room, tied up helplessly by Kaylee and her mean little gang, with the humiliating 'Fart in My Face' sign she left by my head, I was visited and farted on by lots of the school teachers. Lucky for me, they were only the female teachers. I smelt lots of flavourful womanly farts that day, and it was finally coming towards the end of the school day.The end of my embarrassing torture, or so I thought...The very last visitor came...

3 years ago
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BONEHEAD SQUARE

BONEHEAD SQUARE Upon my arrival, there didn’t seem to be a lot of activity, so I stayed at the counter and conversed with the clerk. Few words had fallen before I heard footsteps, looked to my right to get a visual on a man walking toward me from the area where I should have gone right away. The look of longing on his familiar and handsome face as he walked toward and then past me with a nod of acknowledgment told me I’d arrived too late to attend to the needs of his thick and uncut seven inch...

2 years ago
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Doubleheader Games

Doubleheader Games By Deborah Edwards and Jillian O "You would look great in that," the friendly sales clerk said. "I'm sure we have one in you size." Obviously this teenage girl with the big smile was getting paid some sort of commission. "I can go to the back and check for you," she said with a question in her voice. "Ok, I'm a size 8, I'll browse while I'm waiting." I answered while she scurried away. I hadn't come to the mall for a wool skirt, but it wouldn't hurt to...

2 years ago
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Girdlehead

"Girdlehead" Brenda was a big girl, tall and buxom with wide hips and a pendulous bust but she wasn't fat. And she was attractive, always dressing in something feminine, a bit old style actually. She was always seen in dresses or skirts and blouses and after I started dating her I found out to my approval that she enjoyed the most feminine of old fashioned lingerie as well, including seamed hose, the frilly, lace trimmed full slips and the sturdy heavily paneled panty girdles...

2 years ago
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Headhunting For The Board

(Chorus) More than friends We will be lovers In the dark I change my skin One last kiss And it will be over May your sweet dreams Come to an end In this hideaway In the land of darkest night I'll take your breath away The pleasure and pain is mine If you'll be with me You will sleep forever Dream of an ecstasy The pleasure and pain More than friends We will be lovers In the dark I change my skin Change my skin 'Change My Skin', Christopher Franke, "Raven"...

3 years ago
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Skinheads

WALL STREET BLUESFuck, what a day thought Kerri.  Slamming down the pedal of her Beamer, radio up, sunroof open Kerri was ready to put this day of work behind her.  Being an up and coming Wall Street Investment banker had its highs.  The salary was great but some of the days were just draining as everything went downhill.  She should be working late but everything was so fucked up she left anyway.  Whatever! She thought. Texting Jimmy she made sure they were still on for mountain biking when...

3 years ago
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Headgirl as bhabhi 2

Deepti abhi bhi ro rai thi. Humne report li or wapas aane lage par vo chup hone ka naam hi nahi le rahi thi. Maine bike roki or uske gaal se aansu puche. Itna karte hi vo rahul bolkar mujh se lipat kar fut fut ke rone lagi. Maine aishe hi khada raha . Thodi de baad vo hati or mujhe sorry bola. Maine use hankey diya. Usne apna chera saaf kiya. Ab maine pucha deepti baat kya hai. Deepti boli 2mhare matlab ki baat nahi hai. Mujhe ghusa aaya or hum ghar jaane lage. Maine bike khadi ki or apne ghar...

2 years ago
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Headmistress Favorite Sport

Headmistress' favoritesport By 2NN Authors note: Be warned: Thisone is more than a little extreme. This story shouldnot be shown to, or be read by, minors. It is strictly adult material. Prologue The twins Joannaand Jocelyn watched their older brother, Dennis, with contempt. They boththought that he was a complete wimp, a weak little sissy. Being related tothe useless creep was embarrassing. Not only was he small and weak, his tinyhands and feet combined with his very fine features made...

2 years ago
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ShoeOnHead halloween party

Omg you are at this random Halloween party and you don't know anyone. You don't even know how you ended up here. It's then you see someone you recognize from across the room. You can't tell where from however, until it hits you! That's ShoeOnHead! What is she doing here? You look around and try to see if there are other youtubers around or if anybody else recognize her. It doesn't seems so, at least for the moment. She is hard to recognize in that slutty outfit though. She is usually quite...

3 years ago
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Headmasters Rules

Mr Dafydd Evans thumbed through the report on his desk. Five pages of misbehaving from two young girls both aged sixteen and born just one week apart; both of them just three weeks away from their seventeenth birthday. The reports were from Mr Gregory who taught Mathematics, Mr James who taught Geography and the worse report from Miss Thornton who taught Religious Instruction. It wasn’t a one-off.This report landed on his desk on the last day of the month, as it had done for the last...

Occupations
1 year ago
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Flathead

Thanks to the Hip and Knee doctor for editing assistance. Flathead-- From 1920 through 1969, Flathead Indians and Harleys were a major force in American motorcycling. Up until I met Candy, there were only two things in my life of any value: the 1946 Flathead that my father gave me, and the 1917 Navy Luger that my grandfather brought back after World War 2. I wasn't what you would call an ambitious fellow. I usually went with the flow and always took the easy way out. Now, don't get the...

2 years ago
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Bullhead City

A needed weekend getaway with an old flame. Loughlin, NV is a small town on the Colorado River, south of Las Vegas. On the other side of the river is Bullhead City, AZ. Many people from California have "vacation homes" in Bullhead City. Most of these are mobile homes. Many also have boats and pontoon boats (party boats) for water recreation. There are several hotels and casinos in Loughlin, and each has a "ferry" service from the Bullhead City shore of the river over to their establishment...

2 years ago
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Airheads

“Can’t wait to feel a hard cock shooting cum inside me.” I was trying to sneak past my sister’s bedroom door, but that phrase rang in my ears and rooted me to the spot at the top of the stairs. At sixteen, my older sister Jenny was an annoying sibling. Shallow, nosy and a tattle tale; she seemed to revel in any trouble she could get me in. So I always did my best to avoid her. It wasn’t too hard for me to get away from her nosiness, but I always had to be careful. The difference...

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