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IT'LL BE FUN By Persephone © 10/31/16 A tale of an old trunk, an old dress, an idea for a Halloween costume party, and a job contract that all conspired against Jack to keep him in skirts and dresses. And if he wins will he lose or if he loses will he win? Read and find out. This started out as a short simple Halloween story but it turned into a monster before I had finished. I hope you like it. Feedback appreciated. Chapter One Jack and Casandra (Sandy) met in college at the end of their sophomore year and dated during their junior year. They moved in together during the summer break after their junior year. After graduation they rented a small apartment for a couple of years and then, as Sandy moved up the corporate ladder and Jack's consulting business grew, they decided to buy a house together. They found an old house built about 1900 that suited their needs and taste. Marriage had been mentioned many times but just didn't seem to be necessary. It was something that they planned to do "later" when things settled down and they were ready to start a family. But buying the house seemed to bring out the domestic side in Sandy and she hinted until Jack finally caught on and popped the question. They got married in a small civil ceremony with just a few friends present. Then Sandy continued to pursue her career and Jack concentrated on growing his business. Kids were not in the formula yet. They both still enjoyed their freedom for vacations, hobbies, and other interests. One of Sandy's hobbies was buying and restoring antique furniture. Usually the smaller things like end tables, nic-nac shelves and such. She loved to go to estate sales and rummage through the lifetime collections of things that families sold off after the passing of a family member. Jack didn't like picking over "the bones of the dead" as he called it but he did appreciate the beautiful old solid wood furniture that she refinished and reupholstered. It made their house very "homey" and gave him a comfortable feeling. She had even learned how to crochet doilies to add to the feeling. Jack was busy in his home office one Saturday cleaning up the last few things on one of his contracts when Sandy returned from a day of "bone picking." He heard her car door and then shortly afterwards she poked her head in his office door. "Can you give me a hand unloading the car?" she asked. "Sure. Be right there." Jack went outside and found Sandy's Ford Explorer backed up to their detached garage. She was just opening the back when he arrived. "You won't believe the beautiful old wooden steamer trunk I found. It's locked up so I have no clue what's in it but I plan to refinish it and use it as a coffee table in the den." Jack tugged the large trunk out of the back and set it on the garage floor while Sandy was rummaging through her tools. "There it is," she exclaimed as she held up a tool that looked like a bent awl. "This is a pick that I use for cleaning out carving on furniture. It should work to open that lock." "Well I'll leave you to your treasures." "Aren't you curious what's inside? Stick around for a few minutes." "Okay. Probably just a bunch of old junk though." A few moments later Sandy triumphantly announced, "There! That's got it! Now let's see what treasures we have." Jack let out a small sigh as she raised the lid. The top drop in tray was filled with small things. Sandy held up lace handkerchiefs, silk stockings, garter tabs and other very old bits and pieces of a female wardrobe. She also found a jewelry box containing necklaces, rings, bracelets, earrings, and broaches. There was also an envelope with a letter inside. It was addressed to just, "Augusta." Sandy pulled out the letter and read aloud, "Dearest Sister Augi. It was so wonderful of you to visit us for the wedding. We thoroughly enjoyed having you here. Too bad you couldn't stay longer but your tickets didn't permit change. Sorry your trunk didn't arrive at the dock on time for the sailing but Albert arranged for it to go on the next ship sailing for New York so you should have it a few days after you get home. All our love, Your sister, Hazel. Kidderminster 1893. "I wonder why she never unpacked her trunk?" Sandy questioned. "Who knows," Jack answered. "Maybe she didn't need what was in it." "I doubt that. She'd have wanted the jewelry at the very least. Let's see what's in the rest of it," Sandy said enthusiastically. Jack sighed again as he lifted out the tray. Sandy started going through the clothes. She pulled out an old whale bone corset and looked at it. "Check this out. What a torture device but it's really beautiful. Look at the brocade panels," she said as she held it up. "Wow! It's huge. She must have been really tall but with a great figure." She laughed at the next item as she held it up for Jack to see. "What's that?" He asked. She stood up and giggled as she wrapped it around her waist. "It's a small bustle," she said as she turned so he could see it poking out behind her. "Extra padding to enhance the female caboose." "I guess nothing really changes. Now women use tight pants and padded bras," Jack said shaking his head. "Yeah but it's a lot more comfortable than squishing your waist with a corset and walking around with this thing poking out behind you. At least this is a small one. Back around eighteen-seventy or eighty they were huge and stuck out about a foot. This one was just a bit of an enhancer," she said as she continued pulling out blouses with mutton chop sleeves, long skirts, slips, nightgowns and other undergarments; all of them high quality silk and satin. Then she came to a long formal evening gown. She stood up and held it in front of her. It was beautiful. It was all flowing draped folds and layers from the waist of a pale blue ending at the hem with a wide white ruffle of lace. It was trimmed everywhere with gorgeous white lace. It had a sort of square cut neckline that would show ample cleavage with wide lace trimm over the shoulders. The long sleeves ended with more wide white lace and it had what looked like an apron around the waist but it was in the back and hung over rear end with a large blue bow. "Damn! She was a big girl. Especially for that time period. She must have been five, nine or ten. About your height Jack. And by the look of the corset and the bodice of this dress she had tiny waist and an ample bust too," Sandy said as she moved over to Jack, turned the dress around and put it up against him. "You know, as thin as you are, I bet this dress would fit you perfectly if we used the corset." "Well we'll never know because I'm not about to wear a dress and I certainly am not going to be wearing a corset," Jack answered smiling. "Now don't dismiss the idea out of hand, Jack. Halloween is coming up in a couple weeks and we have to attend the annual executive Halloween party. This dress would be an absolutely perfect costume. Who knows, it might even win a prize." "Fine. You wear it," Jack responded. "I already have mine, you don't. I'm five foot six. This dress is way too long for me but it should fit you perfectly." "What about that "ample bust" thing you mentioned? I certainly don't have that and I don't want to go out in public in drag. I'm no queer!" Jack returned. "Jack. It's a Halloween party. A lot of guys dress as women on Halloween. I'm going as a high class call girl and you thought I looked hot in my costume. Does that mean I'm actually a prostitute? Do you think that's what I really am just because I dress as one for Halloween?" Jack knew he was between a rock and a hard place. "No. Of course not. But I just wouldn't feel right or comfortable in a dress.. Everyone at the party would laugh at me. A guy in a dress. I'd be embarrassed, humiliated." ""Hmm. Okay. So it's a fragile male ego thing is it?" she asked. "I wouldn't put it that way but if it works for you, okay, blame it on my male ego," Jack responded a bit testily. "So what you're saying is that you'd do it if no one at the party knew you were a guy in a dress. Right?" "I'd know." "We weren't talking about you. You said 'everyone at the party' would laugh. But if they didn't know you were a guy in a dress, they wouldn't laugh, right? And if they didn't laugh at you then you wouldn't have any reason to feel uncomfortable, embarrassed, or humiliated any more than any woman wearing that dress would and your male ego would remain intact. Right?" Jack was getting a good dose of why Sandy was so successful in her job as a contracting officer negotiating contracts with the people they did business with. She was boxing him into a corner. He could feel the walls getting closer but gave it another shot. "Yes. If they didn't know, that would be true but there is no way that they wouldn't know. I'm five foot ten. I have facial hair, a deep voice, no hips or butt, and a flat chest. If you put me in a dress I would look like a guy in a dress. There's just no way around that," he said confident that he had presented insurmountable obstacles for her to overcome. Sandy had a small smile at the corner of her mouth which gave Jack cause to wonder if he was right. "First off, your just barely five, nine. Second you shave once a week and even if you don't all you have for facial hair is a light downy fuzz. Third, you voice is hardly what I would call deep. I know women that have a deeper voice. With the right tones, inflections, and breath, you'd have a beautiful sultry contralto or alto voice. And fourth, women have been using strategic padding like forever. Enhancing your figure to add what you lack is the least of the problems. But let's not debate the fine points. Why don't we get down to the brass tacks and..." Her point by point breakdown hurt a bit. "Fine," Jack cut in. "And just what are those brass tacks? I know you. I recognize your negotiating voice. You have a proposal so get to it," he said. He had a feeling that he was almost firmly lodged in the corner now. He'd been there before and knew the feeling well. In his mind he thought, 'At this point it's best to just quit arguing and let her present her proposal.' His mind smiled as he thought, 'Yeah. And then I give her whatever she wants every time.' Jack leaned back against Sandy's workbench and waited. "You're right, of course. What I propose is that you give me this week to make the plans, put things together, and get you ready. You do as I say without bitching or griping and then next Saturday we get you dressed up and see how you look. You will cooperate with every step and when we finish we will have three judges evaluate your appearance. You choose two and I choose one. All five of us get one vote. If I'm right, you wear the dress to the party. If you're right, we find another costume. That weighs the vote in your favor with yourself and two friends to myself and a friend. Does that sound fair?" Jack stared at her thinking, 'Of course it sounds fair. She always sounds fair but she always has a kicker in the deal somewhere that that sneaks up and bites me in the ass. But I can't see it. I never can.' "Okay. I agree that it sounds fair but you're devious and always stack the deck in your favor. That's one of the things I both love and hate about you. It seems I hardly ever win, and when I do, I get the feeling that you planned it that way. Now who the hell am I willing to let see me in a dress?" "How about Bill and Todd?" she suggested. They were their neighbors on either side. "I'll even give you Mary and Louise. You're way closer to all of them that I am what with you working out of the house and me being at work or on business trips so often. That gives you five votes to my two. What the heck, I'll even give up my two votes. How's that for a deal?" Now Jack knew he was in trouble. She was seemingly giving him a guaranteed out. 'How could I possibly lose if I have all the votes,' he wondered. 'The only way is if she can actually do what she says and they agree but I'm sure that's impossible.' "Okay. It's a deal." Sandy held out her hand and he shook it sealing the deal. His gut turned. He just knew he had been played but had no idea how or to what extent "Great! Now help me pack everything into the house so I can sort it out. I'll have to get the dress to the dry cleaners and wash and iron the rest." A little later Sandy left to take the dress to the cleaners and do some shopping. Chapter Two Jack was busy in his home office working on another contract when Sandy finally arrived home from work. She had called at noon and told him she was leaving work early but would probably still be late because she had a lot of stops to make on the way home. "I wonder what new torture she has in store for me now," Jack said aloud smiling. He got up from his chair to go greet her and wobbled briefly. He cursed under his breath the high heels that Sandy had bought for him the night before. That morning she had him put on a pair of knee highs and the black patent pumps with the two inch heels. She told him he needed the practice before Halloween. Jack walked out to meet Sandy with the heels clacking on the hardwood floor of the hallway. He met her in the entryway as she was hanging up her coat. "Well, I see you're still wearing the shoes. How's it going with them? You seem to be doing pretty good." She said as they moved to the den. "Oh just dandy. My calves are killing me, my toes are cramped and smashed, and these damn stockings are pulling the hairs out of my legs. Other than that, I just love them," he answered sarcastically. "Well just be glad I started you with only two inch heels. I bought you some three inch heels tonight for when you master those. The retro style shoes I ordered for you to wear with the dress have three inch heels so you'll be the right height. As for the cramps, you'll work through those as your legs get accustomed to them. And, I told you to shave your legs so don't whine about pulled hairs if you won't do as I say. "You said no bitching or griping, so whining is allowed," Jack responded with a smile. "Now what else have you got in those bags besides shoes?" "Just a few other things to help you practice and get used to moving and functioning while being dressed as a woman." Jack groaned. He had thought this whole thing was just for Halloween but it was looking like he was going to spend the next several weeks "practicing" for his role at the party. "Oh come on Sandy. This is getting way to serious and complicated. It's just for a couple of hours at a Halloween party." "Now hold on Jack. I'm doing this for you. You're the one that said you didn't want to be laughed at and that you wouldn't be comfortable in a dress. I've thought a lot about that and realize that you were right. I don't want you to be laughed at either and the only way to prevent that is to make you comfortable while impersonating a woman." "Okay, I can sort of see the shoe thing. I don't want to fall on my ass at the party but other than these damnable heels, there can't be all that much more to it. Can there? I mean what more could there be?" "A lot! You have no idea," She replied. "There's a lot to learn before you'll be comfortable and at ease. You've never had to manage a long dress or skirt for starters. You don't know yet how to walk properly in heels and the dress only complicates matters. Then there's sitting, turning around with the train, going up and down stairs, going through doors and getting in and out of the car. And then there's boobs. You have to learn how to handle boobs..." Jack cut her off with a lecherous laugh, "Heh, heh, heh. Oh I know how to handle boobs. I'm really good at handling boobs as you well know." "Mmmm. Yes I know," Sandy answered smiling. "But you've never handled them from the other side, Dear. You're going to have quite a pair to deal with. At least a very full C, maybe a D cup projecting out from your chest. You aren't used to allowing for them like in tight spaces or even raising your glass to take a drink. You'll suddenly find an obstruction in your way." Jack took a step back. "Now wait just a minute. You're not planning on me wearing a long dress and falsies for the next two weeks, are you?" "Very astute, Jack. That's exactly what I have planned plus a bit more. Ever since we met I begged you to let that gorgeous hair of yours grow out and you have but you always wear it in that darn low ponytail. I want you to let it loose and learn to deal with long flowing hair about your face, down your back and over your shoulders and chest. You have an appointment for a trim, style and body perm tomorrow afternoon. After the party you can go back to your ponytail with not much noticeable difference." "Whoa there. A perm? Are you serious? I don't want kinky, curly hair. How will that not be noticeable?" "A body perm, Jack. It just gives your hair more body and a bit of a wave. Not curls. It'll be fine." "I suppose there's more?" Jack asked worriedly. "Just a few small things I have in mind," Sandy answered and Jack groaned again. "Oh hush! It's nothing big but still you need to learn to deal with it. While you're at the salon they will wax your legs, do a manicure and pedicure and give you a nice set of acrylic nails. They're also going to give you a complete make over and teach you a bit about makeup and what colors you should wear. You'll need to practice doing your makeup for the party so you can do touchups." Jack backed up again and fell into his easy chair. "A few small things? You call long fingernails, having my legs waxed and a makeover a few small things? That's not small. None of this is small. By the time you're done I won't know myself in the mirror. You're trying to make me look totally like a woman." "Exactly!" Sandy responded "And how is this not going to embarrass the hell out of me at the salon?" :Well you know Janice that owns the salon, right? I talked to her and told her everything and she understands what we're doing. She also understands you don't want to be embarrassed so we're going tomorrow because she is closed on Monday and Tuesday. It'll be totally private. Isn't that perfect?" "Look Honey, I love you dearly but this is getting out of hand. I don't want to spend the next two weeks in drag learning how to be a female. It's just a Halloween party. I went last year as a pirate. We can find a different costume. Seriously Dear, I really, really don't want to do this." "But you agreed and we shook on it. That's like a promise," she pouted. 'Oh god! I hate it when she does that!' Jack thought. "But I really don't want to do this." He repeted. "Okay, Dear. I know you don't want to so I'll release you and let you go back on your word," she said sullenly and still pouting. "We'll think of something else." At this point Jack felt like a shit. He knew he had shook on the deal and he never went back on his word. His discomfort was turning his stomach sour and he knew he wouldn't be able to live with this. Seeing her like this and knowing he had let her down was killing him. Sandy saw his discomfort and knew her words and actions were having the desired effect. 'He's going to break. I know he's going to give in,' she was thinking and she slumped her shoulders and turned to walk away. "I'll go start dinner," she said and took a step. "Oh jeeeze! Okay, okay! I'll do it! You're right! I gave my word and I'll follow through." Sandy straightened up and smiled. She had won again. "Yippee! Thank you Dear. I know I can always count on you doing the right thing but seriously, I will let you out of it if you really want me to." She threw that in as an added guarantee. She knew he would reject it. "No, no. I said I would do it and I will. Just do me one favor please?" Jack asked. "Sure. What?" Sandy responded. Don't make a complete fool of me." "I'd never do that Honey. Not a complete fool." She answered smiling. "Now let's get dinner and then I'll tell you all about what I got for you on the way home" Jack and Sandy sat at the kitchen table eating dinner and discussing her plans for the next few weeks and the party. Sandy itemized each of her purchases and enthusiastically explained to a completely unconvinced Jack why each one was necessary and would help him. He was not buying it. "I know I said I would do this but I also think you are going way overboard for a simple Halloween party." "Okay Jack. I'll be completely honest with you. As you already know, since I was promoted to the executive offices I have had to vastly improve the quality of my wardrobe and upgrade my appearance. Last year was the first time we were invited to the annual Halloween party and I didn't realize just how much the quality of the costumes mattered. Our "over the counter" pirate and barmaid costumes were far less than acceptable and I was informed several times after the party to "up my game" for next year. I've also been reminded several times over the last few weeks." "Damn! I'm sorry. I thought you looked great as an eighteenth century barmaid. I guess my pirate outfit was a little cheesy compared to other costumes I saw but I didn't realize it mattered." "At the lower executive level 'Everything' matters. It's not just job performance but also appearance, what clubs and organizations you belong to, who you know and who knows you. There's a lot of pressure on stuff like that. That's why when I saw that dress I was so excited. It's unique and very high quality. It will be a standout at the party. And that's why you have to be a perfect looking debutant from the eighteen nineties, or at least as perfect as we can make you. I don't want you to be a caricature of a woman in that beautiful gown." "Okay. I understand. I promise to do my best and make you proud of your husband, or wife, or sister, or whatever I am in that dress." Sandy laughed, "After the hard time you gave me I should introduce you as my sister or sister-in-law! It would serve you right. But seriously, you'll be my husband and we'll amaze everyone at midnight. Now come and see all the neat things that I picked up for you on the way home," she said picking up the bags and heading for the bedroom. When Jack finished clearing the table he went to their bedroom. Sandy had everything spread out on the bed ready for him. "Now, because you weren't with me and couldn't try everything on, you'll have to do it now. I can return anything that doesn't fit. We'll start at the skin and work out so strip." "Naked?" Jack asked as he started taking off his shirt and kicking off the heels. "Yep. Now first, here are some CDs that I found online today. They had a local supplier so I picked them up on the way home. They are instructions on how to impersonate a woman's voice. tonal inflections and mannerisms. There's five of them double sided and if you do one CD a day you should be pretty fair by Halloween. You can even listen to them while you sleep or work. At least that's what the sales literature says." As she looked up at Jack he was just dropping his boxers. "You always could undress fast in the bedroom," she giggled. "Now put these on. They're strategically padded panty briefs to give you a little help in the hip and butt area. Oh, you also have to tuck little Jack back out of the way between your legs. And I read online that his buddies should tuck up into your groin and then the brief will hold it all in place." As Jack struggled a but getting them on he said, "You read how to hide a guys package online?" "Yeah. You'd be amazed how much information there is about crossdressing on line. That's good. Now stand up straight and let me put this around your waist. It's a waist cincher and will give you a bit more curve." "Damn, Sandy. That's tight!" he complained as she pulled the laces again then tied them off. She grabbed a tape off her dresser and wrapped it around his waist. "Great! Twenty-five inches. We need twenty-four for the dress but the full corset should do that easy. It's a good thing you're so skinny. Your twenty-eight inch waist was easy to reduce. I was hoping to get twenty-six tonight." "I'm not skinny. I'm slim. And this thing is cutting me in half. Do I have to wear it?" Jack asked with a grimace on his face. "Yes. It's the only way to fit you in the dress." "So now what?" Jack asked fearing the answer. "Put your arms out," Sandy said as she picked up a bra and slid it up his arms. He groaned again as she fastened it behind his back. She picked up a box and opened it and as Jack watched, she pulled out... a breast! And then from another box, another breast. She carefully inserted them into each cup of the baa and stood back to have a look. "They look great. Perfect fit. They can be attached to your chest with adhesive but not now. Maybe after Janice is done with you tomorrow." "Attached? To my chest? I can't go around for two weeks with these things stuck to me. Let's forget about the glue." "Okay Honey. For now. Here, put on this slip." She watched as he put it over his head and let it fall down to his ankles. She smoothed it and adjusted it around his waist as Jack ran his hands over the smooth nylon material and smiled. "Feels nice, huh?" Sandy remarked smiling. "Here, put this on now." She said as she handed him a long sleeved white silk blouse. "I tried to get things that were close in type and style as what was in the trunk. All of them are at the cleaners but you should be able to wear them after I pick them up." Sandy watched and smiled as Jack fumbled with the small pearlescent buttons. "Here. Let me do that. You're not used to such small buttons and on the opposite side too. Okay. Now for the skirt," she said as she finished the four buttons on each cuff. "Put your hands up and slide the skirt down to your waist." Jack did as she said and Sandy fastened the hook and button at the back and then zipped it up. "A perfect fit," she proclaimed as she checked the length and waist. Then she wrapped a wide leather belt around his waist and kneeled on the floor to help him with his shoes. She slipped on some stocking material booties and then the shoes. "These are called peds. They're for when you're not wearing pantyhose or stockings. You still need something on your foot. I'm trying the new three inch heels to see how you do with them. Alright. Now sit on my vanity stool while I brush out your hair." When she finished with his hair she removed the small studs that he usually wore in his ears and put on a pair of inch and a half gold hoops. "Okay. Now stand up and do a slow turn and let me check you out." Jack stood up carefully and walked a few steps into the middle of the room and did a slow turn. Sandy smiled. "I think this is going to work out just fine. You look fantastic and we haven't used makeup or done your hair yet. Take a look at yourself," she instructed as she pointed towards their mirrored closet doors. Jack turned and looked. He was stunned for a moment then took a few steps closer. He stared at his reflection for a bit and then turned from side to side. He finally turned around and looked over his shoulder. "My god Sandy. Except for my face I look like a woman. I have curves. You were right about that strategic padding. Holy shit! This is scary." What Jack saw was a woman with a great figure dressed in a a classic styled long sleeved white silk blouse that draped her ample breasts. She wore a dark blue floor length A-line skirt with a wide leather belt that emphasized her small waist and wide hips. Her long flowing hair fell over her shoulders and came to rest atop her breasts. Even his face seemed to take on a somewhat feminine appearance. "You do look good Dear, and don't worry about your face. Janice will take care of that tomorrow. We'll dress you the same way tomorrow morning. I'm taking off at noon again so be ready to leave here by one o'clock." "I'm not going there dressed like this am I?" "Of course you are. You just said you look like a woman and when you leave the salon you will definitely look like a woman from head to toe, literally. You wouldn't want to leave there in your male clothing, would you?" "No. I guess not." "Right. Now let's go watch TV for a bit before bedtime." Chapter Three The next morning Jack took a shower and used Sandy's shampoo and conditioner as instructed, Sandy blow dried his hair back brushing it while he was bent over. "This will give your hair a lot more fullness and body and it will flow better. You need to get used to dealing with it loose." She explained. She dressed him in the same outfit as the night before and reminded him that she would be back early to take him to the salon to see Janice. When Jack saw himself in the mirror with his hair full and flowing over his shoulders and down his back he came to really believe that she could pull his off. His face had become only a minor distraction on an otherwise totally feminine appearance. They had breakfast together and Jack began to realize what Sandy meant when she spoke about learning to deal with his hair being loose. He was annoyed that he had to keep brushing back over his shoulder th keep it out of his face and his food. Sandy laughed and told him, "You'll get used to it Dear. Just watch me and other women and copy their actions. Soon you won't even notice yourself doing it." Jack spent the morning working on some of his contracts and dealing with his hair, the long skirt, the heels, and the boobs. When Sandy got home she asked him how his morning went. You don't really want to know," he replied. "Of course I do. I want to help you work through all of your problems. After all, I have a lifetime of experience to share with you." "Okay fine. You asked for it. The hair is a pain in the ass. It's always falling in my face as I work at the computer. These tits get in my way and block my view of the keyboard. This skirt is a pain too. It gets hung up on everything as I walk and when I sit the chair wheels roll over it plus it gets all bunched up under my ass. And speaking of my ass, I feel like I'm sitting on a pillow and it pokes out and hits the back of the chair. And that brings me to another point, namely my hips. They barely fit in my office chair. So, is that enough? Sandy was laughing almost uncontrollably. "Oh you poor dear. You've had a female life thrust upon you without the advantage of a lifetime to grow into it. But don't worry. We all deal with those things every day and I'll teach you how. Just a couple of pointers for now and then we have to get going. I've seen you at your desk. You're always hunched over your keyboard so naturally your hair will fall in your face and of course your breasts will block your view. That's why women sit up straighter. Try it. You'll see the difference. Okay, so lesson one complete. Grab the purse I gave you this morning and let's get out to the car. It's best if I drive or you be having another new experience; driving in heels." At the car, Sandy had to instruct jack on the fine points of entering and leaving a car in a skirt. They arrived at the salon on time for Jacks appointment and Janice greeted them at the door. Once inside she locked the door and turned to look at Jack. "Damn Sandy. You said he looked good and you weren't kidding. Okay Jack. Into the back and remove everything but your panties. We'll start with the waxing and get the bad part out of the way first." In the back room, Jack stripped down with Sandy's help and then Janice did a once over. She checked his face, back, chest and abdomen, underarms, and legs. Jack was totally embarrassed and could feel his face getting hot. "Well this is going to be easy. This isn't meant as an insult Jack, but you're almost as hairless as a ten year old. I have a facial depilatory that will take care of that fuzz. It should last about a month. If you keep using it the hair will quit growing back after three or four months. Then you'd never have to shave. Okay, now get up on the table face down." During the next half hour, Jack had what little hair he had on his legs ripped out and had the downy fuzz on his face removed and his pits denuded after which Janice told him put on a robe and move to a chair at the back of the main salon. "Ya know guys, I think I've had enough. This is beginning to seriously impinge on my manhood. I mean, in my teens I was embarrassed by my lack of body hair and now in a short time you've removed what I spent a lifetime growing." "Oh sweety. It'll grow back. Besides, do you know how ridiculous that sounds? You saying that you're upset because becoming a woman is impinging on your manhood? Of course it is. Now just sit down and let Janice do her thing." Jack sat and the chair was leaned back and his neck was fitted into a cutout space in the sink and Janice washed his hair. He immediately relaxed as the warm water and her long nails massaged his scalp. "Now this I could get used to," he told her. When she finished she wrapped a towel around his head and raised the chir back. "Okay. Now come with me to my station and let's get started on you." Jack sat in her chair and she draped a cape over him and fastened the Velcro tab around his neck. She removed the towel from his head and started to comb out his hair. "Sandy said you had nice hair and she was right. It should be truly beautiful when we're done. Now just hold still while I fit this cap on your head." "What's that for?" Jack asked. "Well, your hair is a beautiful chestnut brown but is rather monotone. I'll pull a few strands of your hair through these holes and then use a some medium blonde color on them. Then when your hair is done you will have what looks like natural blonde highlights. It's totally natural looking unlike the ones done with the foil strips which leave wide blonde streaks in your hair." "Blonde highlights? I don't know about that. Can we just skip this part? Where's Sandy?" "Sandy had some shopping to do and no, we can't skip it unless you want to explain to her why. Besides, after Halloween I can always dye the highlights back to your regular coor if you want." Jack thought about it for a bit as she started to pull strands of hair through the holes. He decided that as long as she could undo it afterwards, it was better to just go along than to have to explain his reluctance to Sandy. "Okay. Go ahead," he said. "I thought so," Janice said smiling. "Trust me. You'll love it Jack." And she continued until she had hair pulled through all the holes and then she applied the blonde coloring to his hair. After it finished working she rinsed it out and removed the cap and then fixed the color. Afterwards she put his hair in rollers and added the perming solution. Then she wrapped his head and led him to the dryer. "With that head of hair you have, this is going to take a while so I'll do your nails. Just lean back, close your eyes and relax while I work." Jack did just that and had soon dozed off into a half sleep. When the timer went off, Janice lifted the drywer hood and checked his hair. "Good. Looks like your done. Let's go over to the wash chair and I'll rinse the solution out." She rinsed and neutralized the solution and then took out the curlers and tok him back to her station. As he sat down he noticed a strangeness in his fingers. His nails specifically. He pulled his right hand from under the cape and looked at the long nails on his hand. They all extened a quarter inch past his fingertips and were a super high gloss dark red. "Holy shit! What'd you do to my nails? "It's the latest in acrylic nail technology. They are virtually unbreakable and are bonded to your natural nails so there's no chance of fungus or infection between the acrylic and your nails." "How do I get them off?" "You don't. They're permanent. You have to wait for them to grow out but after Halloween I can remove the polish and file them back to your normal length so don't worry. Now relax while I put the larger curlers in your hair." "Sandy said it wouldn't be a kinky curly. It won't, will it?" Jack asked. "No. This is just a body perm not the heavy duty perm you're thinking about. This will just give your hair more body and a soft natural wave." When she finished she said, "Okay Jack. Time for the dryer again. This time I'll do a pedicure so just go ahead and relax again." Some time later she shut down the dryer again and tested his hair. "Great Jack! Back to the other chair." "This is like musical chairs," Jack said as he glanced down at his feet and saw the ten dark red toenails. He let out a sigh and thought, 'Well at least they're not longer.' He sat at her station again and she told him, "I'm going to work on your face while your hair cools down so I'm going to lean the chair back a bit. I'm going to explain every step and show you what I'm using so you can practice between now and Halloween. Sandy wanted you to be able to do this pretty much by yourself so you can do touchups alone at the party but first I'm going to clean up and neaten you brows." Janice started plucking his brows and he got worried again. "Hey! Take it easy there. You can't fix them if you take off too much." "Relax Jack. I;m just cleaning up stray hairs and shaping them a bit." When she finished she said, "Okay Jack. Listen carefully and try to remember as much as you can. What you forget, Sandy can help you with but you need to know this. I'm using colors to compliment your skin tones and will give you everything I use to take home with you." She then carefully explained every step from blemish cover to foundation and blush. Then lip liner and lipstick and on to his eye shadow, mascara, and eyeliner finishing with the eyebrow pencil. Jack was completely confused. "I'll never remember all that," He said. "Don't worry. Sandy will be teaching you every morning and on the weekends. You'll be good enough to hold your own at the party. Now we'll sit you up for one last thing before we take your hair down." "There's more?" Jack asked. "Yes. One more thing. Sandy wants me to pierce your ears." "My ears are already pierced. She conned me into doing it when we were in college." "Well now she wants them pierced again for the party. She said that you can just take them out afterwards and they'll heal up but for the party she wanted them pierced again." Jack let out a large sigh and groaned, "What the hell! With all the rest you both are doing to me what's two more holes in my ears," but he wasn't prepared for the second sting in his right earlobe. "Hey! How many are you doing?" he asked. "Just two more in each ear." She said as she did the same to his left earlobe. "There. That's done. Now we'll get those curlers out of your hair." After removing the curlers she brushed out his hair and trimmed a few places and declared him complete and removed the cape. Just as he was about to get up and look in the mirror, Sandy came through the back door carrying several bags. "Don't look yet Honey. I want to get you completely dressed before you see the finished product. Come into the back room." Jack swore under his breath but followed her into the back wondering what she had in the bags. He tried to get a quick glance in some of the other mirrors in the salon but they were all at the wrong angle. In the back room Sandy explained, "Alright Jack. First thing is to lay face up on the table again." "No more waxing! I've had it with that." "No dear. Janice is going to attach the breast forms with adhesive and use makeup to hide the seams. That way you can get used to the feel and weight on your chest." "Glued on? For how long?" "Until you see Jenny, my daughter, on the day of the party. She is going to make you an appliance that will look totally realistic for Halloween," Janice said as she removed his robe and guided Jack to the table." "Your daughter is in on this now? Pretty soon the whole town will know. Why does she have to know?" Jack asked. Sandy smiled and said, "Jenny is a professional makeup artist for TV and the movies. She specializes in making appliances to make the actors look like monsters and zombies and such. She's going to measure you this weekend and then make an appliance that will make your breasts look so totally real that even you won't be able to tell they aren't real. These forms are good but hey won't bear close scrutiny and I guarantee that the guys at the party will be giving them a lot of close scrutiny." "Oh joy. Now I'm going to have guys ogling my boobs. Wonderful." "Welcome to our world, Jack," Janice said giggling. "Now up on the table and lay down." She then carefully cleaned his chest and then located and marked the placement of the form and glued them in place while working the edges down. After they had set she applied a long lasting theatrical makeup. "This stuff wil last for several weeks and you can shower, swim, or hot tub with no problem. Okay, you're done. Now Sandy can get you dressed." Sandy got up from her chair as Janice left the room. Okay Honey. I heard you loud and clear earlier about your clothes, hair, boobs an so on. I already told you that if you stand and sit straight, it will minimize those problems but I can also tell you that with boobs your size, forget about ever seeing you feet other than in a mirror," she said with a long giggle. Then continuing, "As for the long skirt, I did some shopping and bought you some knee length skirts and a couple nice dresses. I hope they fit okay. I think you'll like them. You'll still have to practice with the long skirt but these will give you a break now and then." "The liking is all relative. Frankly I don't 'like' any of this but you've got my word until after Halloween so let's see what you have." She handed him a pair of pantyhose and instructed him on putting them on. He was surprised at the different feel now that his legs had been waxed and moisturized. "Wow. Now that feels different." "Kinda nice, huh? Try running your hand over your legs and then rubbing your legs together," Sandy suggested. "Mmmmm. Yeah that's nice too. So now where?" Jack asked. "The waist cincher." Jack groaned. "Do we have to? Couldn't you have bought larger stuff so I wouldn't have to wear that damn thing?" "Nope. We need to train your waist and you need to get used to the restriction. Now turn around while I tighten it." She pulled and Jack grunted and groaned until she tied off the laces. "Now you can handle the rest. Put on the bra, blouse and then your skirt and shoes that I have laid out over there. The skirt is lined so you don't need a slip." Jack was struggling with the bra until Sandy stepped in and helped him. "Thamks. I'm not used to these things being attached and my arms don't bend around my back like yours do." "That's okay Honey. You'll get used to it pretty quick. And they're not "things." They're your breasts. Okay, now here's your blouse." Soon Jack had the white cotton long sleeved blouse on and stepped into the knee length black pleated full skirt. Then he slipped his fet into the pair of black pumps with a three inch medium heel. "Is that it? Or do you have more surprises in store for me?" Jack asked. "Oh there are definitely more surprises for you but that's it for clothing right now," Sandy said as she stepped closer to Jack and fluffed his hair a bit and smoothed his skirt. "There. You look fantastic! I think it's time you got a look at yourself." She took his hand and led him back into the salon. "Okay. Close your eyes and I'll guide you. I want this to be a complete surprise when you first see yourself." Sandy guided Jack over to a triple paned full length mirror and Janice stood next to it with her camera at the ready. Sandy positioned Jack and said, "Alright Honey. Open your eyes." Jack opened his eyes and his first reaction was to look around for his reflection. (flash) That was when it hit him that the woman in the mirror was mimicking his movements. Her head was twisting from side to side and her long waves of hair were flowing back and forth in time with his motions. (flash) That's when he stopped searching and just stared. He looked at what she was wearing and confirmed that it was his reflection and his mouth dropped open. (flash) "Oh my god! What have you done to me!?" he asked. And Janice's camera flashed again. "You're a knockout Honey. You have an amazing figure. You're going to look amazing in that dress on Halloween.," Sandy enthused. Janice stepped closer and said, "You really do look good Jack, or should we call you Jackie now? Your facial features are a tiny bit broad but they still fall within the normal bounds for a woman. With a nose job, brow lift, cheek and chin work you would be gorgeous. But with makeup I was able to compensate for most of that and Sandy can show you how to do it." "Ah, yeah, thanks... I think. And it's still Jack and always will be. This is just until Halloween." "Well I have one more gift for you. Actually it's from my daughter. Close your eyes and open your mouth. Okay, now take a deep breath in through your mouth," Janice instructed. As Jack breathed in she sprayed into his mouth from a small canister like a breath freshener. Jack choked and gagged and was about to speak when she put her hand gently over his mouth and said, "Don't say a word until I tell you. This spray will temporarily raise the pitch of your voice by tightening you vocal chords. It lasts about eight to twelve hours and then you can use it again. I gave Sandy six more for you. Okay, give it a try. Say something." Jack cleared his throat and said, "That tastes like... Holy shit! My voice! I sound like a girl! You're sure this is temporary, right?" "Absolutely. And with those voice CDs Sandy told me about to help with your inflection and vocabulary, you should sound about perfect by Halloween." "Oh Honey you sound wonderful. No one will ever guess you're anything other than a genuine woman. Now we have to get going. Thank Janice and I'll help you on with your new coat." Jack turned to Janice and said, "Thanks, Janice... I think," and turned to see Sandy holding up a long coat for him. He sliped into the coat and Sandy told him to put his hands behind his neck and pull his hair out from under the collar as she demonstrated the action. He did and she buttoned the coat and did up the belt around his waist and then handed him his purse. "Okay. Now hook your thumb under the strap and hold your fingers up like this," she instructed demonstrating with her own purse. "Now put the strap over your shoulder while sweeping your hair out of the way with your fingers. See? That keeps you from getting your hair caught under the strap." Jack followed her instructions and the turned to the mirror again to stare at the young woman standing there in her coat with her purse slung over her shoulder. He was impressed with his appearance but scared at the same time. Between the two of them, Sandy and Janice had made all vestiges of his male self disappear and created this good looking woman. A thought ran through his mind, 'If it was that easy to make me look totally like a woman, how much did I look like a man to begin with?' Sandy broke him out of his thoughts when she took his arm and said, Alright Jackie. It's time we got going and let Janice go home." She turned to Janice and said, "Thank you so much. You did a fantastic job on Jackie." "It was a pleasure. I'll see you both again on Halloween when we do your makeovers for the party. And don't forget, Jenny will be at your place this Saturday to measure and mold Jackie for her appliances so she can have them ready for the party. Good luck you two." Chapter Four Jack and Sandy left the salon but instead of going to their car parked in front, Sandy steered Jack down the sidewalk. "What are you doing? The car's right there." "It's dinner time. We're going to Guido's. I feel like some Italian. My treat." :Are you nuts? I can't go in there like this." "Like what?" "Like this!" he said indicating his clothing. "Dressed like this. Like a woman." "Jackie. You saw yourself in the mirror. You heard your voice. If it looks like a woman, walks like a woman, and talks like a woman, what will people think it is? Now relax. You need the exposure so you act and feel natural on Halloween." "Argggg! You're killing me here, Sandy! Okay. Fine. Let's go." "Just remember to do the things I've told you. Small steps, smooth your skirt when you sit, smile, speak softly and watch me. Try to copy my actions." Halfway down the block they reached Guido's. As they entered the lobby, Sandy removed her coat and draped it over her arm. Jack followed suit switching his purse from one hand to the other just as she had done. The hostess greeted them and Sandy asked for a table for two and they followed her to the table. He watched Sandy's every move like a hawk and did his best to imitate her movements. "You're doing great Honey but try to not stare at me so hard. Be more relaxed and casual. You'll draw less attention," she said quietly. "Relaxed and casual!" Jack said in a strained whisper. "I'm a guy sitting here in a restaurant with a bazillion people all around me while dressed in a skirt and blouse and wearing makeup and you say to relax? I'll be lucky if I don't have a heart attack!" "Calm down! Or do I need to slap you like the hysterical woman your acting. Take a deep breath and look at the menu. The waitress will be here soon and you need to order." Jack took that deep breath and several others and did eventually calm down a bit and by the end of desert he was actually beginning to enjoy himself. Sandy's casual banter about their plans and the meal helped to distract him. He was even able to follow her to the ladies room to freshen up after the meal. The fact that no one seemed to notice anything out of place did a great deal to bolster his confidence and it showed in his more relaxed demeanor. He realized that Sandy had been right and that he did look good enough to pass in public. But he still didn't like it. Not one bit. Back at home he spent the rest of the day dressed and tried to do a little catch up work for his time lost that afternoon. The long nails drove him crazy when he used the keyboard but Sandy helped when she told him to use the tips of his nails. It worked but was still a bit awkward. "You'll adjust to it, Daer." After dinner, Sandy led him to the bedroom where she revealed some more of her shopping purchases. "I thought that you might like this. It will sort of keep you in the right frame of mind all night," She said as she held up a baby blue satin nightgown with white lace everywhere. Then she pointed to the bed saying, "I also bought you some nice satin panties to sleep in and a robe and some mules with a short two inch heel that match the robe. Aren't they beautiful?" "Yeah. Beautiful. But you're getting way too carried away with this whole thing. You must have spent a small fortune buying all this stuff today not to mention the salon trip and just exactly what is Janice's daughter going to cost? For crying out loud, Honey. It's a freaking Halloween party! Even if it is an executive competition thing. All this money for what? Clothes and shit that I'll never use or wear again." Jack complained. "I really haven't spent that much. Not when you consider that some of the other costumes at the party will cost upward of a thousand dollars or more and we got the dress for free. And who says you'll never wear them again? I really enjoyed lunch with my girlfriend today. Maybe we could do it again every once in a while," Sandy said with a big smile. "Oh no. Not happenin'.My promise ends when we get home after the Halloween party and I can guarantee you that I will never let you wangle me into anything like this again. Ever!" "We'll see what the future brings. But for now, strip and put everything on. Then we'll get that makeup off your face and have a nice night drinking some wine and watching a movie I picked up. And then, who knows what might happen." The rest of the week went as well as can be expected. Sandy went to work and Jack worked on his contracts, albeit rather uncomfortably. Even though Sandy had bought him shorter skirts, she insisted that he wear the long ones during the day as 'practice' for the party. Plus he was still dealing with the long hair and breasts, although more successfully, and with the long fingernails. He was also having to deal with the restriction of his waist, which Sandy had tightened down to twenty-four inches by the end of the week. On Saturday just after lunch, the doorbell rang, and without thinking, Jack answered it. By the time he was standing with the door wide open it was too late so he just said, "Can I help you?" to the young lady standing on the porch. She smiled and put out her hand and replied, "You must be Sandy. I'm Jenny. My mom told me about your husband and I'm here to get measurements to make his appliance for the Halloween party." Jack was a little flustered that she thought he was Sandy but let it slide and said, "Oh, yes. Please come in." After she was in he guided her to the kitchen as she requested and then he called out for Sandy. "Honey. Janice's daughter is here. We're in the kitchen." When Sandy walked in and introduced herself, Jenny was visibly confused. "You, you're Jack? That's amazing. I'd never have guessed and I spend my days making people look like somebody or something else. Wow! You're a natural." Jack wasn't sure whether to be pleased or upset so just responded with, "Thanks," and a smile. "Well. I best get started," Jenny said. "You should strip to the waist so I can get a look at what I'm dealing with. I'll get my stuff set up here on the table." Jack reluctantly unbuttoned his blouse, removed it and stood there for a bit. Jenny looked up and said, "Bra too honey. I can't make a form with it on." After he removed his bra she checked him out and held up some color swatches to match his skin color then said, "Great. We can leave the forms on. Mom did a great job. You can go to the bedroom while I mix up a few things here. Spread this plastic sheet on the bed and lay down. No pillow. I'll be right there." Jack nodded and she handed him a large plastic sheet. Jack grabed his clothes and the sheet and went into the bedroom to wait. Jenny was soon there with a large pail. She rubbed something all over his chest she called a release agent and the started to put plaster in a thick layer all over his chest and up over his shoulders and the front of his neck. She then laid a layer of what looked like a gauze cloth on it and started in again with the plaster type stuff. When she finished, Jack had over an inch of the stuff on his chest. "This won't take long. It sets up hard as a rock in about ten minutes. Then I'll lift it off and you can clean up and get dressed. I'll use this as a form to make your chest appliance that I'll put on you on Halloween. No one will ever know it's not all you," She said smiling. After Jenny left, Jack was cleaning up when Sandy came in and said, "I laid out some clothes on the bed for you to put on when you get finished there." "A different outfit? What for?" he asked. "We're going out to dinner." "Do we have to? I don't relly feel all that comfortable going out like this." "My point exactly. You need to get comfortable before the party so get dressed. And if you're a good girl I'll let you take me to a movie too." When Jack glanced at the bed he saw a black dress and it didn't look to him like there was very much to it. "Isn't that a little bit ahh... Well it doesn't look big enough. I mean like there's not much to it." "Every girl need an LBD Dear. A little black dress. And this is yours. Can you believe I found it in Goodwill and it still had the sales tags on it! It's brand new and in your size for only six dollars!" "Okay. That's it. I know I promised and said I would go along with your crazy scheme but that didn't include a little black dress. I'll go out tonight but in a normal skirt and blouse. Okay?" "At least try it on. You'll see it's a very modest LBD. The hem is only a few inches above your knees and the top has cap sleeves and shows very little cleavage. It's quite modest and proper for a night out to dinner. Please?" "Alright. I'll put it on but I'm not going out," Jack said as he removed what he had on and started to get dressed. He put on the black lace trimmed panties over his padded brief and then rolled the shear black stockings up his legs. Sandy helped him with the garter belt and to attach the tabs to the stockings. Then he put on the waist cincher and she tightened the laces. Then came the black lacy bra that matched his panties and then he let Sandy help him into the dress. She zipped it up the back and handed him a pair of patent leather stilettos with a four inch heels an ankle straps. "Here. Put these on and then we'll do your hair and makeup." After jack put the shoes on he sat at the vanity, Sandy draped a cape over his shoulders and pulled his hair back. She removed his makeup and then started to reapply a much more dramatic look with dark eye shadow, heavy mascara, and full red lips. Then she did his hair in a semi-updo with strands strategically left loose and hanging down that she used her curling iron on. A pendant necklace, dangling earrings, a bracelet and several rings and he was finished. "Alright Honey. Stand up and take a look in the mirror." Jack walked a bit unsteadily in the new heels but made it to the mirrored closet doors and stared at himself. He turned from side to side and smoothed the skirt of his dress. He played with the curled strands of hair and checked out the exposed portion of his breasts. "Damn! This is amazing... and scary as hell." "why scary? I think you look wonderful. Very pretty. That dress shows off your figure and legs beautifully." "That's it. That's exactly what's scary. God Sandy, I look in the mirror and I can't tell that I'm not a woman. With the other clothes they covered enough that it never really... well I never really looked so totally..." "Like a beautiful woman?" Sandy finished for him. "That's what I wanted you to see Dear. You have no need to worry about going out and you can see that the dress does not over expose you and the skirt is flirty but plenty long enough for modesty. I dressed while Jenny was working on you so grab the clutch purse on the bed and we'll get going. I made reservations." It was at that point that Jack first noticed that Sandy was dressed similarly and was looking totally hot. He was defeated and outmaneuvered again so he silently picked up the purse and followed her to the front door but when they reached the living room he was shocked when a group of voices all shouted out, "Surprise!" It was their neighbors, Todd, Louise, Bill and Mary. Jack was dumbstruck. Bill was the first to speak. Looking at Sandy he said, "Is that Jack or did we ust blow the surprise? Cause if it is Jack, he just lost the bet big time." "Oh it's Jack alright. Or maybe Jackie until Halloween. Depending on your votes," Sandy answered with a smile. "Damn dude. You look so fuckin' hot. I'm afraid you just lost my vote," Todd said Bill spoke up again, "Hell yeah. Shit man, I came here to vote for you but there's no fuckin way I could get away with it. You're one hot piece of..." "Enough Bill!" Mary cut him off. "Watch your mouth! There's four ladies present and we don't need to hear your foul language." She turned to Jack, Sandy and Louise, "Sorry girls, and especially you Jackie, but you know Bills mouth." Jack knew Sandy had set him up with the makeup, hairstyle and especially the dress and heels. He knew he had lost any chance of getting out of wearing the old dress to the party so he gave up gracefully. He smiled and said, "I guess I'm going to te Halloween party in a dress." "Damn! You even sound like a chick," Todd said and everyone laughed. They all talked for a while and then Sandy announced that they had reservations. "We'll be late if we don't get going. See you all there." "Everyone's going?" Jack asked surprised. "Yep. It's Jackie's birthday," Sandy answered. "Oh well. They say misery loves company. Let's go," Jack said smiling. They put on their coats. Jack remembered to remove his hair from under the collar and check himself in the mirror. He just shook his head and followed Sandy out to the car. He found that the four inch heels weren't all that bad after wearing the three inch ones the last three days. They had a pleasant evening for the most part. Jack did feel a bit uncomfortable with his buddies and some of the guys in the restaurant giving him the once over but reasoned that in their shoes, he would be doing the same thing. He decided that this was just something that women learned to live with and he thought, 'And what the hell, as long as they are leering and not yelling about a man in a dress, I guess I look pretty good.' It was a definite boost to his confidence, if not his male ego, which was Sandy's plan all along. She knew that if all went well and she could make him feel comfortable, it would make her plans for Halloween work out perfectly. After dinner their friends left for home and Sandy and Jack went to the movie which was anticlimactic after everything else that happened. Sandy was very pleased when Mary and Louise had confided in her that Jack was amazing and that his voice and mannerisms were almost perfect. So, after the surprise party and their night out it was very little problem for Sandy to get Jack to go out shopping at several outlet malls and stores on Sunday and during the rest of the week. She even convinced him to do the grocery shopping and do a few errands like picking up the dress at the cleaners. It all provided more training and she was sure he would do great on Halloween. On Saturday he went to an appointment at the salon and Janice touched up his hair, hails and another waxing, just to be sure," and more beard removal cream. She generally checked him out completely o make sure he was ready for Monday night. Sandy took Monday off to prepare and to be there when Jenny showed up to do the final fitting of his appliance for the party that night. The house was awhirl with activity. The dress and all accessories were brought out. Jack took a long hot bubble bath with sweet smelling bath salts and Sandy powdered him with similarly scented talc and had him put on his padded panty briefs, robe, and mules. He was declared ready just as Jenny rang the doorbell. They went to the bedroom where Jenny once again laid out the plastic sheet on the bed and had Jack remove his robe and lay down. She removed the forms and cleaned his chest, sides and back with alcohol wipes and then laid the appliance on his chest. She carefully marked the boundary and then removed it and applied an adhesive. After a few minutes it dried and she had him roll over and marked his back and applied more adhesive. She explained that the appliance already had adhesive on it as she pulled a thin plastic sheet from the back. Then carefully, starting at the marks on his side, she worked her way across his hips over his waist, up his chest and over his shoulders and then around his neck. Jenny then had him roll over and worked across his back at his waist and up to mid back. After that she pushed and poked all over until she was satisfied and then worked the edges. After sealing the seams and blending in the edges with makeup she declared him finished and had him sit up. As Jack sat on the edge of the bed he glanced in the mirrors and was shocked once again. The forms had looked okay but this was unreal. The skin tone was a perfect match and the breasts looked totally real. As he sat there he began to feel a tightening sensation around his waist. It was like the waist cincher crushing his middle. He put his hands to his sides and looked up at Jenny questioningly. "Getting a bit tighter?" she asked grinning. " No shit! It feels l

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WE attended two funeral services together, Mary and I, one low key in terms of attendance but deeply emotional, on one morning and followed that by another higher profile one the following afternoon, that was more for public show than anything else. Mary insisted I attend by her side for both funerals. How could I deny her my full support at them both? To be honest, I wanted to spend every moment of our shrinking allotment of time we had together. Mary wore the same black outfit for both...

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Living With Erectile Dysfunction

I had flown half way across the country to see my lover. We had not been together in three years; each home with our respective primary partners. Our relationship was open. It was very sexual. When one of us arrived and we were initially together, G was normally a little nervous. Once in our room, we would take our clothes off. We would hug and kiss reasonably briefly, and with a little sexual touch, I would be quite aroused. G would relax as my cock entered her and we would have a...

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Impregnation game using a funnel

Impregnation game using a funnelIt is just so very slutty to get impregnated from a funnel, especially with multiple guys contributing sperm. I love the videos our avid members have found and contributed. I hope there are more posts and videos coming.A SEXY PREG RISK GAMEWhat I think would be sexy is a game at a swingers club or at a breeding party.Everyone signs waivers saying no one else will be held responsible for any results and it is fully consensual. STD test results can be exchanged or...

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The Fundraiser

”Welcome, ladies and gentlemen, to our marathon charity show for the victims of the dreadful earthquakes in Nepal.”Paul Sumner, late night talk show host, newspaper columnist and stinking rich philanthropist, was hosting a huge televised charity event being beamed to millions of homes worldwide."Everyone has seen the shocking images and heard the heartbreaking reports, and tonight we,” — and he pointed directly at the camera — “that is you at home and those of us here in the studio, are going...

Exhibitionism
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Fundraiser

Fundraiser A drabble by Karen Hansen The gavel fell, then clapping... Lance, now Lynnette, stepped carefully down the stairs. Cuffed, he couldn't catch himself... led past the people... "How wonderful 'she' looked enfemme..." "What a 'nice' gesture..." Lance couldn't see the last bidder. Mistress whispered, "See you in 48 hours." Winking. It couldn't be too bad... different Mistress... new chores... it's what Mistress wanted... to help out the...

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Masculine Funk

One Wednesday evening, as I was sitting at the bar in a coastal city that renowned for its humidity, I was enjoying the balmy atmosphere as I sipped on a beer. I was very happy that a colleague had recommended this ‘arty’ area to me.The guest lodge I was staying in was charming, and all the shops and restaurants in Roper Road, as the area was referred to, had a lovely vibe. Of course, of special interest to me was the gay flag that I had observed hanging from the first floor of one of buildings...

Gay Male
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Malfunction

Malfunction The 3 laws of Robotics: 1. A robot cannot harm a human being, or through inaction, allow a human being to come to harm 2. A robot must obey the commands of a human being, except where such commands would counter Law 1 3. A robot must protect its own existence, except where such protection would counter Law 1 or Law 2. Matt, the engineer assigned to fix me calls me Abe. That's when he isn't using profanity. My official designation is ABEVE - 2110...

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Die Stckelschuhe Episode 1 Gesucht und gefunden

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All Systems Functioning

 Earth date 1st April, 2121. Time 12h03m56s GMT. Space Station Alpha 69. Geostationary above Mars. Unmanned. Nothing to report. All systems functioning.*Earth date 2nd April, 2121. Time 15h05m23s GMT. Space Station Alpha 69. Geostationary above Mars. Unmanned. Nothing to report. All systems functioning.*Earth date 3rd April, 2121. Time 10h23m19s GMT. Space Station Alpha 69. Geostationary above Mars. Unmanned. Nothing to report. All systems functioning.*Earth date 4th April, 2121. Time 16h02m45s...

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The Fundraiser

I had to raise money for my school track team by selling candy bars. I was crafty and had the perfect sales pitch for every crowd to would show it to. The parks for the sugar hungry k**s after school, and other places i had up my sleeve that other team mates wouldnt think to try. My sales were going excellent and i had almost sold all of my chocolate bars, however, 23 boxes remained. I went to the police station and the fire house, gave a sweet lil sales pitch and sold 8 of the 23 boxes. I had...

2 years ago
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Four Funerals

(This story isn’t true, but it’s based on some real events. I just put them together.) Tottenham Court Road on a busy Friday lunchtime is not the tine to start playing Frogger for real but the young woman in front of me obviously didn’t realise that. I was moving before my conscious brain kicked into gear, my hand shooting out and yanking her back by her shoulder as the taxi swerved to avoid a bike courier weaving in and out of traffic. It happened in slow motion, the taxi screeching into the...

1 year ago
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Weddings and Funerals

Weddings and funerals are the only time our whole family gets together. It is like a reunion. I mean they come from all over, the extended family from both sides. So this story takes place at a wedding, I can't remember who got married but I remember the important parts. My family arrived several days early as did most everyone. The first day we all went to the golf course and drank. Uncle Carl and Aunt Beth were ready to go and made me the designated driver. I loved being around Uncle Carl and...

2 years ago
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A Fresh StartChapter 141 Funerals

After that, I left the podium and exited out a side door. There wasn’t going to be any schmoozing in the aisles tonight. Once outside the chamber, I sent somebody in to find the Commandant of the Marine Corps and ask him to see me for a minute or two. I smiled as I considered that. Once upon a time if a senior officer ‘asked’ me to do something, it was really an order. Now I was the one doing the asking. My, how Second Lieutenant Buckman had grown up. Marilyn and the kids showed up about a...

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Probability Dysfunction

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4 years ago
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Freddys Family Fun2

Josie's job was quite near the mall where he intended to go so Freddy decided to accompany his sister on her bus ride to work. On the bus the boy would sound out his sister's views on sex in general and perhaps sex with her brother in particular. The teen wasn't so sure how to go about it. He knew subtlety was needed but that wasn't his strong point. Well, he would just have to play it by ear. "You're looking sexy this morning, sis." A few compliments never hurt to start out Freddy...

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Freddys Family Fun1

"Huh? What!" Freddy was deep in sleep. Oh shit! Was the place on fire? It was his cousin, Nina. "Move over. I'm going to sleep with you." Freddy knew he wasn't hearing right. My brain must not be in gear yet he thought. It sounded like Nina was going to get in bed with him. How was that possible? The bed was barely large enough for one. "Why? How?" Freddy just wanted Nina to go away so he could get back to sleep. The fact that she was a cousin whom he'd lusted over for years...

3 years ago
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Eastern Funday

It was Easter and my best friend Zack was going over to the apartment of his long-term girlfriend, Ashley. When he arrived at her place, she greeted him with a kiss and they headed straight for the bed room, not waiting to get down to their usually dirty business. Ashley was still wearing her pajama clothing, which consisted of soft pajama pants and a light shirt with no bra underneath. As soon as they made it to the bedroom, she unzipped his pants and pulled them off his legs. Ashley then...

4 years ago
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Double the Funn

My friend, Jill, and I had been friends for a long time.   She and her husband lived down the street and she was a big comfort to me during my recent divorce.   Last month, my divorce became final and Jill said that we should go out and celebrate.   She said, “Girl, you are single again and need to start getting out and meeting some guys”. And knew that Jill sometimes played around on her husband and so I thought to myself that not only did she think I should get out but that she wanted to go...

3 years ago
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Fundraisers

"Here's the problem my friends," the mayor was saying. "Here in Texas, we're living in a cesspool of human tragedy. We have an influx of immigrants, squatters and the homeless. As you all know, they need clothes, food, and shelter. Many children need medical attention. Our community is doing all it can to help, but our resources are limited. In a month or two, we will have spent our entire budget for the year. Most of you have contributed through your church or through the Red Cross but...

Teen
3 years ago
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Shemale Funpark

You go to a Funpark in Miami, Florida where you are supposed to meet your Friends. You really like them and drove all the way out here just for them. Right as you enter the Funpark to get to the meeting point, your Friends call you in a groupchat. They tell you that their Car broke down a long time ago but their Phones had no Battery and they were in the middle of nowhere. They could only call you now to tell you that they sadly can’t come to the Funpark. They say that you have to go on the...

Transsexual
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Die Unterwerfung

Der Kontakt war über eine Kleinanzeige entstanden. Werner hatte die Annonce aufgegeben und sie war die erste, die geantwortet hatte. Er sehnte sich danach, nach langer Zeit endlich etwas Besonderes zu erfahren. Ein wenig Nervenkitzel, ein wenig Spannung. Der folgende Mailverkehr faszinierte ihn enorm. Er mochte sie sofort und konnte das erste Treffen gar nicht abwarten. In dem Moment, in dem er ihre rauchige Stimme am Telefonhörer vernahm, war es um ihn geschehen. Täglich rief er sie an. Und...

BDSM
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My first time in Jamaica part onecoupleforfunnyc

Ok so of you read my previous stories you know about Darrel . Dave also knew about Darrel and wanted us to try swinging together . We booked an adults only resort in Jamaica because it's was one of the cheaper ones . As we arrive they are giving everyone drinks at the airport and the guy handed it to me and says your going to have fun here ! .I thank him and continue to our transportation to the hotel . We see a sign and we stand with the rest of the crowd but we realized everyone was a bit...

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Funfair

It was a warm hot summers day at the fun fair Sun kissed freckle faces and messy hair Dribbling ice creamspinning round and round on rides so fast The thrill of the roller coaster making my belly flip as you’re zooming around The wizz making you feel horny as hell. Day time slips into night time Bright lights hairspray and the fairgrounds still open flashy lights loud musicAdults onlyI’ve had a couple of glasses of wine and my mates playing ClaweeOnly the stuffed toys have all disappeared And...

2 years ago
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JoggingFun

A few months ago I notice that I gain some kilos. So I decided to do jogging and lose weight. I bought some lightweight jogging pants and top and sports bra. Near our home is a track where lots people jog especially at evening when hot sun goes down. After work I drove there one evening. Oh there so many cute guys there and it fun to watch their buts when they run. I could not run all way around track and so I walk some and jog some. I try go there about 3 times week. I began recognize some...

3 years ago
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Friday Funday

Friday, and the efficiency at the office where Laura was working was winding down, most of her colleagues were thinking of the weekend and the plans they had made, but Laura had been buzzing with a restless energy all day long. By lunch time she had made a decision, she was going to clock off early, thank God for flexible working hours. In a very uncustomary way she caught a taxi home instead of the bus, and was almost running up the stairs to the small house that she shared with her partner...

3 years ago
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Joes geile Mutter 1719 Netzfund

Am Freitag dieser seltsamen Woche lernte ich dann auch Sues neuen Freund Dave kennen. Nicht direkt, aber irgendwie schon. Die letzten zwei Tage waren in Langeweile verlaufen, denn Mom hatte im Büro wieder viel zu tun, kam spät heim und war dementsprechend müde. Manchmal fragte ich mich, ob sie wieder das Penishöschen tragen würde und dann lief ich in ihr Schlafzimmer, durchwühlte den Kleiderschrank und fand diesen Slip regelmäßig, verborgen unter einem Stapel alter Wäsche, ganz hinten im...

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Aumlgyptisches Viagra funktioniert

Vor einer Woche sind mein Mann und ich vom Urlaub aus Ägypten zurückgekehrt und obwohl Ägypten ja nun nicht gerade ein erotisches Urlaubsland ist, möchte ich euch von einem Erlebnis berichten, das insbesondere mir viel Spaß bereitet hat. Auch, weil mein Mann nichts davon mitbekommen hat.Unmittelbar nach unserem Flug wurden wir per Bustransfer in unser all inclusive Resort verbracht, wo wir unser Zimmer bezogen. Die Anlage war sehr weitläufig aber gepflegt und wir waren zunächst mit unserer Wahl...

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FunAtBeach

, you know I like to have fun in the beach. But now I tell how much fun!! Hope you not get upset for me not say before to you. I and my cyberlover decided to meet in Boracay. He is lawyer in US and his name is Joseph and he looks gorgeous at his early’s 50 based on webcam. You see him on cam and know we like sex together on cam. We had not yet seen each other in person. He had a lot of fantasy in bed which made me surprise as I did not have any idea about his fantasy. I was really curious...

4 years ago
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Nadjas Schlachtung Teil 2 Netzfund

Mein Name ist Nadja. Ja das hatten wir schon. Ich bin 175cm gross, habe weibliche Rundungen, einen klasse Arsch und mit 80c auch ordentliche, feste Brüste. Mich ziert langes rotes Haar und ausser meinen Augenbrauen ist das auch schon alles Haarige an mir. Von daher wurde ich auch mit der Güteklasse A- ausgezeichnet. Das Minus da ich leider ein paar Probleme mit der Leber habe. Nichts gefährliches, aber die Leber ist entsprechend nicht zu gebrauchen. Auch das hatten wir schon.Was wir jetzt aber...

1 year ago
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Nadjas SchlachtungNetzfund

Darf ich mich vorstellen? Mein Name ist Nadja. Ich lebe in der wunderbaren Zeit 2078. Warum wunderbar? Weil wir auf der Erde mittlerweile 17 Millarten Menschen haben und keine Hungersnöte mehr.Das Ganze fing 2022 an. Aus den Vegetariern wurde eine Bewegung, dann eine Partei und letzten Endes kam es sogar zu einem Krieg. Dieser war jetzt nicht so Blutig wie die Weltkriege, aber letzten Endes führte sie zur Gleichstellung von Tier und Mensch. Nun dachten sich die Vegetarier wahrscheinlich, sie...

2 years ago
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Mit Mama in der Sauna Netzfund

Da meine Mutter Geburtstag hatte, und sie mit mir was unternehmen wollte, schlug ich vor in eine Sauna zu gehen. Eigentlich waren wir noch nie in einer gewesen, aber da wir es Beide ausprobieren wollten, nahm sie meinen Vorschlag an. Meine Mutter wurde 40, aber sie war stellenweise wie ein verspielter Teeny. Dafür dass sie bereits so alt war, sah sie immer noch gut aus. Sie achtete sehr auf ihr Äußerstes und sie pflegte ihre langen schwarzen Haare. Dazu war sie schlank, aber ein wenig breit...

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SaipanFun

Honey, the trip to Saipan last month great. You know my company sent me there for almost a week for training and meetings. They make reservation for me to stay at Resort hotel—great view and beach! Work was intense and stress. So one night I wear tight jeans and halter top under blouse and sexy bra and went to the street bazaar, like in Manila for relax the stress. Many stalls, locals, and tourists. I got thirsty and hungry and sat alone at nearby small restaurant/bar. Then I observe...

3 years ago
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Sex With A Widow Mature Lady Whom I Met In An Func

Hi friends am a great fan of the sex stories, after a lot of courage this is my first sex story which was encountered with and am still enjoying with that sweet lady.Let me quick jump into the story. Well am Raj (name changed) and am 31 years old married with good body, 6’1 height with 75 kg weight well built.The story begins like this, I had been to a function with my parents there I met a lady she must be around 45 but I must say she does not like she is her 40’s she looked like she is 30yrs...

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Ich will zur WM Netzfund

Vor einigen Wochen beschloss ich mal wieder Urlaub zu machen. Ein klares Ziel hatte ich zuerst nicht vor Augen.Bis ich die Tageszeitung aufschlug und mir eine Annonce ins Auge sprang:"Fußball-WM 2010 in Afrika, wer jetzt bei uns seinen Afrika-Urlaub bucht bekommt 2 Premium-Tickets zugesichert."Da ich ein großer Fußballfan bin und ich von der WM 2006 wusste wie schwer es war an Tickets zu kommen, ging ich mit mir einen Kompromiss ein. Ich dachte: "Dann warteste eben noch nen` Jahr auf deinen...

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Just Another Sunday Funday

So I just got back from one of my favorite days: Sunday. Most people hate it because it's the day people go to church. But that's exactly why I like it. You see, every Sunday, one of my oldest and dearest lovers invites me to his home while his wife is at church. He also invites several of his friends…who invite their friends…and who invite their friends ;-) We call it "Sunday Funday".While I usually travel very discretely, these men want me in full drag, in the sluttiest outfits and...

2 years ago
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Cum Funnell

This story is purely fictional.It was a long winter and I had been working overtime every week for the last few months when i decided i deserved a vacation. I purchased a ticket down to Miami where I knew the weather would be nice and looked forward to a change of scenery.When I got off the plane I rented a car and was driving out of the airport when I noticed an adult book store. Since I was affraid to travel with my toys and needed a bigger dildo anyway I stoped in to look around. The place...

3 years ago
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The Funhouse

Boonville. An aptly named town, as it's about as far in the boonies as one can get. The typical routine is one of sleep, work, sleep, any and all excitement kept to a bare minimum in this town of 2,000 people, who are mostly concerned with keeping the stoic tradition of boredom alive and well in their families. However, for one week a year everything changes. Bright lights, laughter, and visitors from all over flock to Boonville for a single reason - the Carnival. Not the most...

2 years ago
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Eastern Funday

It was Easter and my best friend Zack was going over to the apartment of his long-term girlfriend, Ashley. When he arrived at her place, she greeted him with a kiss and they headed straight for the bed room, not waiting to get down to their usually dirty business. Ashley was still wearing her pajama clothing, which consisted of soft pajama pants and a light shirt with no bra underneath. As soon as they made it to the bedroom, she unzipped his pants and pulled them off his legs. Ashley then...

Bisexual
4 years ago
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Infuntration

Cascadia University was a busy place, Always crawling with students and teachers and mentors of all kinds and shapes. There was only minimal campus security and the campus itself was luxuriously outfitted, with an attached spa, pool, and recreation rooms. It was a normal Tuesday morning in all respects, and a stream of students entered the building, packing the front hall of the building before spreading out in to the many, many other rooms that made up the building. In the midst of this...

4 years ago
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Double the Funn

My friend, Jill, and I had been friends for a long time.   She and her husband lived down the street and she was a big comfort to me during my recent divorce.   Last month, my divorce became final and Jill said that we should go out and celebrate.   She said, “Girl, you are single again and need to start getting out and meeting some guys”. And knew that Jill sometimes played around on her husband and so I thought to myself that not only did she think I should get out but that she wanted...

BDSM
3 years ago
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THE FUNHOUSE

THE FUNHOUSE College girls on spring break take in the sights.  Safety in numbers, they room together near the beach, party together at night.  Hooking up with a local and letting him hang out with them a couple times, they accept his offer as a group to spend a couple hours at a nearby traveling carnival.  Entering the funhouse, lost in its maze, their exit’s not what they expected. Chapter One        Making their way through the carnival funhouse, nervously giggling, huddling together, the...

4 years ago
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Friday Night FunTime

     Friday Night FunTime!A Femdom Family-Slave Story!        TJ Ryder     http://midnightx.com/fpage/fpage.html        Buxom Ballbusters Illustrated StoriesGestapo Mistress, Dommy mommies, femdom cuckolding!     Illustrated Fetish Stories for Adults Only!**************************************   "Hi Billy!"  The 38 year old said to the teenager who he had met thefirst time he came here to the newcomers group.   'Hey Tim, everything okay?"   "Well, its been an experience,(smile)!"   "What's...

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Maspalomas funshine

Life is way too short for monogamy!I’ve been married to the most incredible slut for the last five years now.Krissy is 26 years old. She has the most perfect figure with ample tits, tiny waist, big hips and a gorgeous booty!She also has a voracious sexual appetite that keeps me in shape.I’m 28 years old. I’m told that I’m good looking with dark hair and blue eyes. I work out constantly to keep my ripped, lean body in shape for my sexy woman. I am also blessed with a mighty thick and long...

2 years ago
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Sunday Funday

Sunday Funday By Selene Victoria [email protected] It was one of those days where I didn't wake up until the sun streamed across the bed and into my eyes. I hadn't had a particularly late night, nor a hard one, but given the rare opportunity to sleep in, I took it. Sunday was my only day off that week, and I had been swamped with projects and deadlines since practically longer than I could remember. My wife Catalina was already awake next to me and, judging by the...

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Opus OneChapter 35 Finale Langsam Ruhevoll Empfunden

The moon was overhead when the first hint of eastern glow touched the horizon. Jupiter was close by, accompanying the hemicycle as it fled from the coming sun. Closer to the earth, strains of music tentatively began to sound; quiet hours were coming to an end. All around, the Wexford dormitory was stirring. The banal sounds of students trudging to the restroom to bathe were merged with the footfalls of early risers, who were already headed to the conservatory to find a better practice...

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Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

2 years ago
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A New Lease on LifeChapter 15 Malfunctions

It’s mid-October, and the Fall Dance is getting close. It’s basically the homecoming dance but with a different name and always fall themed. I told Danny that I would take him and Beth out for this dance. My streaming tips have been great over the last month, and I’ve been saving up since school started. Danny tried to argue and say he can take us both, but I shot him down and he eventually relented. The twins, Cindy and Mindy were going to go with themselves again this year, guess Jake can’t...

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Gaia Mother Earth Book 3 of A Thousand Years of PeaceChapter 10 The Planet Funston

“Looks like we are ready to go.” George said. “Okay everybody. Stand in a line. We come back here for lunch. Okay? Stay with your buddies now. If you get lost, then transport to the front gate. Now I have some money. Remember the silver may be worth more than the gold here.” John handed out a silver coin and a gold coin to all the kids. He handed out 3 silver and 3 gold to all the Marines and Sally and Bobby. He handed out 5 coins of silver and gold to Vid, “If you buy with my money then I...

2 years ago
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Age I Of The United StatesChapter 10 Malfunctions

There were words carved into the polished stone, but they were in a language that Tara didn't understand. She traced them with her finger and once more felt a surge of power rush up her arm and through her body. She also noticed a stylised carving of a man's head. There was a shout from across the pit and Tara turned to see Sigurdson and another of the troopers waving. She hurried across to see what was up and found the navigator and the trooper standing over a pair of skeletons, the bones...

1 year ago
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Tenchi Muyo All Good ThingsChapter 81 Funaho

Lady Funaho had changed little since Mihoshi had last seen her. But then, she had 'changed' little in the last thousand years if the truth were told. One did not bring such matters up around the queen of Jurai However, if one wished to remain in good health. "I would say that this is an unexpected pleasure." The queen politely intoned. "But of course we know that would be untrue." Kiyone stood staring, uncharacteristically mute. Mihoshi however, having met the queen on more than one...

3 years ago
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Sunday Funday

"Oh yeah? That's awesome, I for sure wouldn't recognize a celebrity if I randomly ran into them. Ha! Well cheer's thanks for the drink!" James said as their glasses clanged. A shot of Fernet on a Sunday morning, James thought with a smile. It was only his second month being in a new town and being able to converse with new people over a simple football game felt nice. "I'm Rodge by the way." The man shifted his arm over. "Jim, nice to meet you," James said reaching out and feeling the...

1 year ago
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Strygans Funhouse

No one is ever sure how they end up at the gates of Strygan's Funhouse, and you are no exception. You stand in an eerie yellow-green spotlight, surrounded by swirling opalescent mists. Strygian's Funhouse towers over you, its endless stories disappearing into the dark clouds above. A giant grotesque scowls at you, it's open maw a portal to the rooms within. The air smells faintly of smoke, and somehow sinister sounding calliope music escapes from the portal before you. A disembodied voice,...

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