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Summer student ? by: Jennifer Stewart Chapter 1 - A Money Making Proposition Billy Chambers was a 19 year old student in the Department of Physics at Stanford. He was exceptionally talented and, would begin postgraduate work at an important national laboratory in two months time. His career was on track but he was wretchedly poor and had few prospects of raising his income to the point where he could enjoy some of the comforts of life that he had enjoyed when living at home. Billy's sister, Anne, was two years older. She had graduated from the College of Arts and was expected to do brilliantly as an actor. However, at this stage of her career she too was desperately poor. Billy and Anne had received money towards their living and tuition costs from their mother but she was now dead and, unexpectedly and disappointingly, she had left debts rather than assets. It was a difficult situation and, on the afternoon that the will had been disclosed, they sat together in a small French restaurant finishing a bottle of Chateauneuf du Pape, they speculated about their financial prospects for the foreseeable future. "Okay, your scholarship will only take care of tuition, and I can scrape by on my pay for the next three months run of the play, but what happens when the run ends?" "I hate to get a job. The first year at the lab will be really tough. If I have to sling hamburgers or work in a bar to live I will never be able to handle the workload. Mother was giving each of us a $1000 a month. That's a lot to replace. What on earth was she living on herself?" "I think it's obvious that she was literally starving herself to support us." "Poor mom. Well we have to come up with a way of making an extra $1000 a month each. At least you can sell your body," said Billy, giggling. "I know. I've thought about it." "Anne! I was kidding." "I know you were but it's not such a silly idea. I like sex and I have a friend who works for an upscale escort agency. I think she could get me in." "Anne, I don't think you should do that. It's dangerous." "Steph' said that this is a well run agency and the clients are very carefully checked. She has never had any trouble. She says she enjoys the work and the pay is fabulous. I could help you out until you get settled." "Anne! I would be living off the 'wages of sin.' I mean that metaphorically but still, what kind of a shit would that make me." "Oh, stuff the morality. We have a serious cash problem and we have to be pragmatic about it. After a year at the lab you'll start to make some decent money - but only if you do well. I am sure I can make enough from the agency to support both of us comfortably." "I don't know what to say. Ethics aside, I am really touched that you would do that for me." I leant over the table and kissed her. "I'll find a way for you to pay me back." Billy knew that was not intended as a threat. Three weeks later they met again in the restaurant. Anne was in the agency and starting to make money. "I make $600 for every hour I spend with a client and its straight cash. That means no taxes. I work every other night and, have no more than four clients. This weekend Steph, me and three other girls are going to LA to work a convention. I could make over $4000 for a weekend's work." "Wow! Shit! That's amazing." Anne smiled happily. Billy studied her, trying to picture her having sex with all those men. She was a pretty brunette hardly taller than 5' 2". Her slim, athletic slim body was bursting with energy and life. Billy worried that working, as an escort would dissipate that joie de vivre. "Don't worry. Sex is good exercise for the body and the mind and I really enjoy it. I have a group of regular clients who I really like and I still feel excited about meeting someone new. I'm learning some amazing new ways to do it. Anyway we have talked enough about me. What have you been doing since school ended." "Trying to find a job that will pay a huge wage for two months. There's not many out there. I'm feeling a bit defeated." "Good." "Thanks." "No, I'm glad you have reached this point because I have a proposition which you would otherwise probably turn down without thinking about it." "I'm not going to sell my body." "That's not what I was going to suggest." "Okay, what then?" "In the agency I hear about all kinds of unusual things going on out there in the big wide world that most people never hear about. Well next week there is going to be a private fashion show at a very exclusive club in Malibu. The models will be T-girls ..." "What's a T-girl?" "It's a transvestite or transsexual. Anyway, as I was saying, there is this private show and the organizers are looking for three models. Each model will be paid $3000 and get to spend a weekend at the club, which is in a fabulous mansion on the beach. There will be a lot of people from the T-girl magazine and video industry. All of the models will have all kinds of opportunities to get some very lucrative contracts. It's a great opportunity to get into the big time in this genre and make some serious money without spending a lot of time away from your studies." "And you think I should put on a dress and go spend a weekend with a bunch of weirdoes? I don't think so." "Wait. Just think about it. I am talking about making more money in one weekend than you could make in two months at one of the jobs you have so far failed to find." "I am not going to wear a dress." "For a good chance to make $3000, why not? It's just liked an acting job." "Because I'm not a fruitcake." "Oh god! Here we go. Let's get all the male hang ups out into the open right now and deal with them, then perhaps we can talk sensibly." "That's not fair. I don't see why my not wanting to wear a dress should be called a hang-up." "Of course it is. When there are people ready and able to pay you a lot of money to see you dress as a woman and you need the money and the best you can do is say you don't want to be thought of as a fruitcake ... Well I think that's just stupid." Billy hated it when she got mad. He could not think fast enough to answer her arguments, which meant that he usually lost. He also knew that he was on shaky ground because she was giving him half the money she was making from her escort work. "I just don't want to become known as a sissy." "No one will know. This is a very private club. They are all men who have a thing about T-girls. They think they've died and gone to heaven when they can watch a good-looking guy like you dress up as a woman. Believe me they will never tell a soul about you." "What kind of people are they?" "Mostly businessmen. Many are gay. Others are bored with their wives or women in general. The world is full of people with unconventional interests. If I walked into their clubhouse wearing a sexy dress they would not give me a second glance but if you do they'll give you three grand. Amazing eh?... But its true." That was a lot of money and Billy knew he had no right to turn it down and take her money instead. "Tell me what I would have to do." "First you will have to be picked. They are looking for very attractive males who can look convincingly female. And they have enough money to cast a wide net for the best." "What makes you think I would do?" "You would look beautiful in a dress. You wouldn't even need make-up. I'm pretty but you have a smoldering, sexy look that will knock people over. You have classical feminine features ... No, I don't mean that in a derogatory way ... In male clothes you're just good-looking but in a dress you'd be gorgeous. You're one of these people that looks great as a male or female." She made him feel quite proud of himself. It was true that his nose was straight and finely chiseled, his cheekbones were high, his eyes were large, dark and deep, his chin was small and slightly pointed and he had full red lips. When he smiled dimples formed in his cheeks, which his mother had always loved. "With a bit of make-up you would look fabulous." Billy's defenses crumbled. He found her quick arguments and praise irresistible. "Okay, what do I have to do to get picked?" "Take some lessons. There is a woman at the agency, who trains new girls how to make themselves attractive to men. She's very good. She taught me things about being a woman that I did not know about." "Will I have to have sex?" "No way. You don't have to do any thing you don't want to. Probably some of the models will and there are T-girls who work at the club and do that." "What about clothes and jewelry?" "I'll lend you some of mine and I can loan you some money to get some things of your own. Once you have been picked the club will supply everything." "You seem very sure that I will be picked." "I am. One of the organizers is a client and I showed him your photo. He can't wait to see you in a bra." She giggled and putting her hand on his said, "Just kidding. Don't look so serious. You might have fun. It's only dressing up. Remember how we used to do it when we were kids? You really liked wearing that satin bed jacket of mom's." "He remembered. The satin had felt extraordinarily soft and sensuous. It gave him his earliest hard-on." "Alright, I'll do it." "I knew you would come around. I'll call Jean tonight. Her name is Jean Waters. She's strict but I guarantee you'll fall in love with her. You'll have to stay at her apartment for a day or two. The auditions are on Thursday and on Friday you fly to Malibu. That means you have three days from tomorrow to get ready." She phoned Miss Waters when they got back to the house and arranged for Billy to go over there the next morning. "She has enough clothes and I will give her some money that you can use. You can pay me back after your weekend in Malibu." 2 - Miss Waters Billy arrived punctually at 9 O'clock in the morning. He knocked on the door of her apartment and it was opened by a tall, beautifully coifed and dressed woman. She was wearing a sleek button front, navy dress in a soft crepe. Her hose was nude colored with a silky sheen and on her feet she wore dress pumps in navy suede. A gold, marine link chain draped around her slender neck, gold hoops in her ears, a gold bangle on her right wrist and a gold watch on her left set off the elegant dress. Her make-up was the absolute minimum required to enhance her beautiful features without taking away from her soft, luminous complexion. Her face was framed in rich, shoulder length auburn curls. She was beautiful, sophisticated, elegant and radiated self-confidence. Billy was intimidated. "Hi. I'm Billy Chambers." She gave him a long, searching look. "Come in Billy. Let me show you your room and then we can get down to business. Anne tells me you have to be ready by Thursday. That's not a lot of time. How do you feel about dressing as a woman?" "Well I haven't got over the shock yet. I suppose I'll get used to it. I just can't believe that I'll be very convincing." "Don't worry. When I've finished with you your mother would be convinced she must have borne a daughter all along." "First thing we have to do is get you outfitted in something suitable so that we can go shopping." Her apartment was tastefully decorated and spacious with two bedrooms, a large living room, dining room and kitchen, a large airy bathroom and a solarium. It was decorated in an art deco style. The floors were highly polished hardwood with an exquisite Persian rug in the center of the living room. The two armchairs, a chaise and large sofa were upholstered in a dark gray antique satin brocade. The dining room furniture was a Scandinavian style polished teak. "This is beautiful." "Thank you. I like it too. Now, while I go and run a bath for you, I want you to go into your bedroom and get undressed. I'll get you a housecoat to put on." She showed him into the spare bedroom which had a double bed covered in a pink satin bedspread with a matching bed-skirt. There was a dresser and chest of drawers. On the dresser was a selection of cosmetics, an earring tree full of earrings and a jewelry box. As he was removing his sweatshirt, shoes, socks and slacks she came in a put a mid-thigh length wrap robe in white satin chemise. Billy put it on. "Take off your briefs. You won't need them for a while. I'm going to put your clothes in this drawer. From know on you will dress as a woman." "All the time?" "All the time, even in bed. Now are you going to take off your briefs?" She spoke with authority and Billy took off his briefs, blushing as he did so, because his pathetically small penis was exposed. "This is going to be much easier than I expected." "Why?" "Well, the penis is always a bit of a problem to hide but yours is quite small." "I know. I've always hated it." "Well, you can consider it an advantage for once. I want you to think and feel like a woman and a big penis will not be help. Think of it as your clitoris. Now get into the bath and I'll help you shave." Billy slipped off the robe and stepped into the hot scented water. After changing into a tracksuit she came into the bathroom and put a couple of razors on the edge of the tub. "I have made an appointment for you with a laser specialist to remove all your body hair but the traditional method will have to do for now." Most of his body hair was on his legs and there was not much of that. When she got to his 'pubics' and put lather on he objected. "Why is that necessary? No one is going to be looking there." "You can't have unsightly hair showing outside your panty line. I told you, I want you to act like a woman and feel like a woman. You must be conscious of your appearance in lingerie as well as in your outer clothes. Also, you will probably be wearing a swimsuit. Anne said you were going to be a model at the Janus Club's fashion show." "Yes, that's the plan." "Well, you will be wearing some very skimpy lingerie. You definitely need to shave your pubic hair." She shaved and trimmed his pubic hair leaving a small, neat oval just above his penis. He blushed as his penis stiffened when she held it to shave around the shaft. As she worked she explained the regime she intended to put him through. As soon as he was dressed she would take him to a beauty salon to have his hair done and to have a manicure and pedicure. He was also going to have a facial pack and his ears pierced. After that she would take him shopping. "Anne has provided the money. What's your shoe size by the way?" "I take a seven." "Oh, that's lucky. You may be able to fit into mine. Now here's a towel. Let's go into the bedroom." Billy dried himself and followed her into the bedroom. She had one of the dresser drawers open and was picking out articles of underwear. On the bed two breast-forms lay in specially molded containers on the bed. She picked one up and placed an adhesive tape on the inside and then pressed the prosthesis onto his chest. "Hold it while I do the other," she pressed the other into place. "Now slowly let go and see if it holds ... Good. Now put this on." She handed him a white satin push-up, under-wired bra. Billy slipped his arms through the straps and took hold of the two ends. Stretching them behind his back he fumbled with the hooks and eyes. Eventually, after a struggle he connected the two parts. She showed him how to adjust the bra so that his bosom was correctly positioned. "How does it feel?" "Stupid." So far he had accepted that he was to adopt a new role but he was not reconciled yet. His maleness was not yet subsumed. Putting on the bra and breast-forms brought out a small impulse to rebel. "I hate it." "That's not what I was asking you. I wanted to know if your bra felt comfortable. I can't help it if you're embarrassed dressing as a woman. I expect that as a male you will have all kinds of insecurities. But let me make one thing clear. I don't care about that. I am proud to be a woman and I have always thanked God that I am not a man. Whether you like it or not, while you are in my charge you will disguise your feelings and wear your bra with pride. Now put on these panties." Her strong personality, which had initially intimidated him, combined with her passion crushed his rebellion. He blushed and stammered an apology. "I'm sorry I did not mean to criticize you." "You don't have to apologize to me but I don't want to have to deal with any of your silly machismo. While you are with me I expect you to constantly strive to be a beautiful, well turned out woman." Billy stepped into the panties, which were made from a white stretch satin. They were high cut briefs and it was immediately obvious that if she had not shaved his pubic hair they would not have covered it. In spite of his embarrassment he was beginning to find the experience quite erotic. As he stood in front of her in his bra and panties he felt a frisson of arousal. The bra and breasts felt so unusual and unexpectedly appealing that his penis had stiffened and produced a very unfeminine bulge in his panties. Worse, a small wet patch appeared in the front of the panties as pre-cum began to ooze from the tip. Jean went into the bathroom and brought back a box of panty-liners. "Well, you obviously find the clothes a little bit interesting - No? You're going to have to remember to put one of these inside your panties or you will soil your clothes. Always keep a couple in your purse too." "Its weird. I have never put on women's clothes in my life, nor had any inclination to. But this is a real turn on." "Possibly as many as one in ten males are secret or overt cross-dressers. For some it's a fetish that may be confined to particular articles of clothing like panties or high heels. I think it's partly the excitement of exploring the unknown and the fact that cross-dressing is such a taboo. In many cases lots of men have strong feminine characteristics, which their stereotypical upbringings force them to repress. It's very common so I shouldn't worry about it. Okay, put on this slip." She was so sure of herself and took for granted that she would turn him into a woman that he gradually ceased being embarrassed. She handed him a white satin slip with lace appliqu? at the bust and hem. He slipped it over his head and smoothed the shiny fabric over his body. He had never worn anything satin before and this simply took his breath away. It was soft and smooth. It caressed his skin. It felt delightfully sexy. His penis was now throbbing stiff. He kept running his hands over the delicious fabric especially over his bosom. "Doesn't that feel nice?" "I have never felt anything like it. It's wonderful!" "Of course. See what you have been missing by being a male. All right, now its time to put on your stockings. Most women today wear pantyhose but I think stockings are much sexier and I think you will enjoy wearing them." She handed him a lace garter belt and helped put it on. Then she opened a package of black nylons. "You're going to wear a straight black, knee length skirt and a white ruffle blouse. You could wear nude or some similar shade but black is more assertive and much sexier." He pulled on the stockings and fastened the tops to the garters carefully straightening the ribbon on each clasp. She was right. Billy liked the way the garters stretched over his buttocks and the gentle restraining feel of the nylons sheathing his legs.. They were very sexy. His mood had changed. Gone were his feelings of doubt and embarrassment. When she handed him the white silk, ruffled blouse he put it on eagerly and his fingers trembled slightly as he did up the buttons. It was a very feminine piece of clothing. Again he noticed the soft tough of the material on his skin. He stepped into the skirt, which was lined and had a front pleated slit. It made a nice rustling sound as he slid it up his legs. He reached behind and drew up the back zip and closed the button fastener. Finally, she gave him a three-inch wide elastic belt with a big gold buckle, which drew in his waist and gave him and hourglass figure. "There, how do the clothes feel?" Billy paused and thought about it then said. "Sexy, definitely sexy but comfortable too. I like the silky feel and the way the skirt brushes my legs. The blouse feels wonderful." "What about your bra. Is it comfortable?" "Oh yes. I like it ... I like it a lot! It feels so neat and ... Er ... liberating." "Liberating? That's interesting. What do you mean?" "It's difficult to describe. I feel like I don't have to put on an act ... The clothes somehow feel right ... I don't know ... It's hard to explain." "Umm! This is going to be easier than I had expected. I can see we're going to have fun shopping. Now, we have to do you make-up." Billy sat at the dresser while she put on a light skin cream and brushed in some blue highlights on his eyelids. Carefully she applied a little eyeliner, mascara and lipstick, her own lips very close to his. He could feel the warm breeze of her breathe brush against his cheek. A surge of desire swept over him. He raised his hand and stroked it across her breast. She straightened up and quickly gave him a stinging blow across his face with the palm of her hand. It was so fast that he heard the crack before he felt the pain. He sat still in shock. "You dammed sissy! Don't you dare come on to me! I told you to act and feel like a woman. If there is any sex between us it will be you getting fucked. Do you understand?" Tears of humiliation and embarrassment welled up into his eyes as she spoke. "I'm s ...orry. Its just that you're ... so beautiful and ..." "I know why you did it but you're supposed to think like a woman. It's quite possible that a man will come onto you. It will be a giveaway if you react like a man. You must try to think like a woman." "Did you have to hit me?" "Are you feeling hurt and humiliated?" "Yes I am!" Tears still flowed. "Good. Welcome to the woman's world. Get used to put downs, petty snubs, and humiliations." As she talked she repaired the damage done by his tears. She was right, of course. He still burned with humiliation, which was compounded by the fact of wearing a bra. At the same time he accepted without question her dominance. As she removed the evidence of his tears with the make up brush his humiliation was replaced by a renewed interest in the transformation that he could see taking place in the dresser mirror. Jean finished his make up and styled his hair in a more feminine way. "I'll spend a lot of time with you showing you how to put on your make-up and when I've finished you'll be better at it than most women. What do you think?" He looked in the mirror and a very attractive 'woman' looked back. "Its very good. I look like a woman." "No. You are beginning to look like a beautiful woman. There's much more to do but it's a start. Try on these shoes." She handed him a pair of black dress pumps with two-inch heels. They fit comfortably. "They fit perfectly." Billy walked around the room, wobbling at first but after a couple of hints from Jean he soon walked steadily. "How do you feel?" "Feminine." "Good, but you look like a man trying to walk in high heels. Short swings when you move your arms ... hands spread out rather than clenched ... that's it. Move your bottom as you walk ... good. Billy spent an hour walking up and down until she was satisfied. We went into the living room and he learned how to sit on a sofa, an armchair and a dinning chair. He practiced feminine mannerisms like resting his hand on his bosom, brushing his hair back with his fingers, and a hundred others. When he made mistakes she snapped at him and when he slipped into his male persona she slapped his face hard, making him cry. She was merciless and he was constantly in tears. Each time he cried she would send him into the bedroom to fix his make-up. After three hours the lesson ended. "Alright, its time to have some lunch and then go to your hair appointment." She handed him a black leather shoulder bag. "Now what do you need to put in your handbag?" "Lipstick and gloss, mascara, eyeliner, eyebrow pencil, cream, and a compact?" "Very good. Go and get them." Billy sashayed into the bedroom and put the cosmetics into the bag. "What else will you need?" "A purse for my ID, money and credit cards." "Good. Use this one." She gave me a slim black leather purse. "Anything else?" "I don't think so." "You need a small package of tissues, a couple of extra panty-liners, and put a little bottle of scent in." When his handbag was complete she said. "Now come and watch me get ready." Billy followed her into her bedroom. This was a large airy room in a granite pink and pale gray damask. The furniture was a spare modern style in ivory. There were few feminine touches except for the cosmetics neatly arranged on the dresser. Her large walk-in closet was full of expensive suits, skirts and blouses but not many dresses. She quickly took off her tracksuit and microfibre bra and thong. Billy watched intently as she opened the dresser drawer and took out a black satin and lace bra and matching brief. She quickly slipped her arms through the straps and reached behind her back to fasten the garment. She expertly arranged each of her firm breasts with large brown nipples into the cups of her bra. Next she stepped into the silky briefs and pulled them up her long slender legs and over her buttocks. Billy noticed that her pubic her was completely removed leaving the lips of her vagina visible. He covered up a surge of desire by concentrating on smoothing his skirt. She sat at the dresser in her bra and panties and pulled on charcoal gray panty hose. She had the body of an athlete and radiated an absolute self- assurance. Billy watched as she quickly applied just a hint of lipstick, eye shadow and mascara. She went into the closet and selected a burgundy silk striped blouse and immaculately tailored dark gray leather pants. On her feet she wore gray suede pumps and, completed her look with gold hoops in her ears and a thin gold chain necklace. She put on a black leather thigh length coat and handed Billy a black silky, nylon jacket. "Are you ready to face the world?" "Yes, I think so." As they walked to the car she said, "Men are going to come onto you in droves. During the week I will teach you how to deal with that problem but for today I want you to ignore any stares, whistles or any approach of any kind. Act as though men don't even exist for you." We drove into the shopping district and stopped at a restaurant. Billy was utterly self-conscious as they entered and felt that everyone in the room was staring at him. As the waitress took them to a table Jean quietly told him to relax. "You look every inch a woman. No one has a suspicion about the real you." She insisted that he only eat a salad even though he was starving. "You will have to get used to smaller portions. Being a beautiful woman means always being hungry." The novelty of being in public dressed as a woman made him uptight and excited. "Relax. Try to look like you do this every day." "It's the clothes. I don't wear a bra every day." "How does it feel?" "I like it. This whole thing is a blast. I think I could dress as a woman all the time. Skirts are much more comfortable than pants and I really like the silky feel of this blouse." They chatted about feminine things and by the time they left the restaurant he was much less self-conscious. The beauty salon was across the street. Jean took him in and told 'Jerome' what he needed. Jean had told Jerome that Billy was a transvestite, which horrified Billy and brought all his embarrassment flooding back. But Jerome was familiar with the sensitivities of cross- dressers just 'coming out' for the first time and quickly relaxed him. Jean left him in his care and went off on some other business. Billy spent the next two hours being pampered while Jerome he gave him lots of advice about being TV. He explained that he too cross-dressed. He was wearing a blue silk blouse and tailored slacks and Billy realized that with a bosom he would look quite feminine. "I've cross-dressed for years and I would be wearing a dress right now except that most of our clients wouldn't like that." 3 - The backdoor Jean returned after three hours and chatted with Jerome about Billy's hair and nails. Billy's hair was relatively long for a male but not for a woman. He had shaped it into a cute 'bob' that had a nice 'bounce' as he turned his head. His ears were now pierced and sported two diamond studs in each lobe. His nails on his toes and fingers had been shaped, painted hot pink, and polished. Jerome had re-done Billy's make-up and was putting the finishing touches to the lip-gloss as Jean had returned to the beauty parlor. "You will need a more feminine name. What would you like to call yourself?" "Umm. I don't know. I like 'Claire' or 'Cynthia' or ..." "Why not Billie ... with an 'i.e.'? Then you won't have to remember anything." "That's very clever of you, Jerome. What do you think, Billie?" "I like it." Jerome took the cape off Billie's shoulders and said. "What do you think?" "Amazing! I look completely female." "Do you like yourself?" "Oh yes. This is neat. What do you think Jean?" "You've done an excellent job, Jerome. You look very pretty Billie." "Beware of men, Billie!" said Jerome as he patted Billie's bottom. Billie giggled and thought Jerome was joking but as he and Jean headed for the mall he was aware of many appreciative stares from men as they passed by. Billie found it intriguing and not unpleasant. He walked confidently and pushed his bosom forward. They looked for dresses first and Billie enjoyed trying on various styles. He was the center of attention and, unlike when he used to buy his male clothes, style and look were now very important. He even tried on a satin ball gown, which took his breath away. He knew that he looked stunning. After two hours they settled on a navy Jacquard dress with a mid-calf length flared skirt and long sleeves, a short-sleeved crepe dress with satin scalloped detail, and a sleeveless red georgette dress, which fell to just above his knees. "You'll need something for evenings," Jean said after they had purchased all the necessary accessories for the three dresses, which included a pair of black patent dress pumps with 3-1/2 inch heels and a pair of silver, 'strappy' sandals with 4 inch heels accented with rhinestones and some pieces of costume jewelry. They went to Jean's favorite formal wear boutique and after trying on three gowns they settled on a burgundy taffeta skirt with a strapless, taffeta corset top and a taffeta shawl. This dress was the beginning of his love affair with taffeta. He adored the stiff silky feel and the sensuous rustling sound of the fabric as he moved. They bought a pair of black ankle strap sandals with a velvet finish and a black satin evening bag. After a break for supper they finished off the shopping trip with a quick breeze through a department store beginning in the lingerie department to buy two bras, six pair of panties, an ivory satin slip, six pair of panty hose, two pair of stockings and a garter belt. Finally, on their way out they passed through the cosmetics department and bought lipstick, mascara, eye shadow, eyebrow pencil, nail polish and facial cream. Billie was exhausted when they got back to Jean's apartment. "God, we've spent a fortune. How much did Anne give you?" "Enough, but it will take you a while to pay her back. Tomorrow, we'll get you some skirts and blouses and you'll need some special underwear for the gown and your georgette dress." Jean lent Billie a satin nightgown and after a relaxing cup of tea he went to bed and snuggled between the satin sheets and folding his arms protectively over his bosom. As he drifted into sleep he reflected on how much he had enjoyed the day. It wasn't bad being a woman. He liked the feel of the clothes, the concern with his 'look' and the pleasant 'restrictions' placed on his body by his bra and the high heels of his shoes. He loved the clingy feel of his stockings and the way his skirt brushed against his legs. He had discovered a real interest in experimenting with make-up and liked the feel of lipstick on his lips. But most of all he has found the way men looked at him very stimulating. He spent the next morning learning more about make-up and trying different looks with some of Jean's skirts and tops. The time flew by as he became completely absorbed in how he could so drastically change his appearance. Jean found him a very quick study and gave him 'his head' to experiment. She had a selection of wigs and he had fun teasing the long hair into various styles with ribbons and clasps. That afternoon they shopped again and when they stopped into a cocktail lounge for a drink, he was thrilled when Jean went to the ladies and a man tried to 'pick him up'. It started him thinking about what it might be like to be kissed by a man. He told Jean what had happened. "What did you say?" "I just shook my head and he left but it set me wondering what it might be like to be kissed by a man," he giggled self-consciously. "Umm! I find it hard to believe that you haven't experimented with women's clothes before." "Why?" "Because you've taken to it so easily. You seem to have an almost permanent erection ..." "Oh God! Is it that noticeable?" "Only when you're undressed but I'm making an assumption." "Well, you're right. I can't help it. The clothes feel so sexy. For the first time in my life I'm glad I have a small penis." Jean laughed. "Have you ever had sex with a man?" "No. I haven't even done it with a woman." "Have you ever fantasized about doing it with a man?" "A few times ... Yes, actually, a lot. It has always bothered me. I never did until one time I saw Anne doing it." "Oh. Tell me about it." "Well, it was a couple of years ago. She was home for the weekend and had bought her latest boyfriend, a big black guy called Jess. He was on the football team. He just towered over her. Any way, I was out in the garden helping mother and went inside to get something. I heard Anne crying so I ran up the stairs and to her bedroom. The door was open and I could see her on her knees on the bed with Jess behind her. I was appalled at first. I could see his huge cock thrusting into her vagina. As his cock moved inside her I could hear a squishy sound as though she was wet inside. He was thrusting so fast and hard that his body made a slapping noise as his pelvis hit her bottom. I was fascinated by the way her buttocks bounced and her breasts swayed. And I noticed that she had big nipples. I quickly realized that her cries were not from pain. In fact, as I watched he pulled out of her and she moaned with disappointment but as he pushed his cock into her anus she gasped with a big smile on her face. The size of his penis just floored me. After my own, this was the first penis I had seen and it was three times as big as mine. For the first time, I felt inadequate as a male." "Umm, that's interesting ... Go on." "He fucked her anally for about five minutes then quickly pulled out of her. He flipped her on her back and put his penis into her mouth and came. I didn't see his cum but it was obvious she was swallowing it. I could not think of anything else all weekend. I never saw them do it again but I noticed the way she touched him and I heard them at night." "Did you imagine yourself doing to a girl?" "No. I just thought about what it would be like to be Anne." "That's interesting. Well, I think you will find out soon enough." "What do you mean?" "Well, you're going to Malibu, aren't you?" "If I'm selected but ...?" "You'll be selected and you'll be one of three beautiful young males wearing provocative lingerie and flaunting yourselves in front of twelve men who find women either unattractive or dull. And you'll be alone with them for a weekend. You're not being paid $3000 just for wearing a bra." Billie stared at her open-mouthed. "Don't tell me you didn't think of that?" she laughed helplessly. "Oh dear, oh my ... that sister of yours is quite the little minx." "She said that I would go for the afternoon and when the show was over I could leave. She said that I would not have to do anything I did not want to do." "Well ... I guess that's true. It's just that I can't imagine you not wanting to. You're such a sexy thing. Oh well, we'll see." She shrugged her shoulders. When they got back to the apartment, Jean decided he was ready for some more intimate feminization. She told him to put away the new purchases and then to come into her bedroom. When he had done as he was told he went into her bedroom. Jean unbuttoned Billie's blouse and slipped it off his shoulders bringing her lips close to his as the silky fabric slid down his arms. "You're trembling. That's good. I don't want you to let your male instincts get in the way. Be submissive and accepting." There was no fear of his male instincts taking over. He was completely intimidated by her. The bra, garter-belt and stockings he was wearing effectively kept his maleness thoroughly subdued. Her lips pressed onto his as she unfastened his belt and unzipped his skirt letting if fall around his ankles. She raised the lace hem of his chemise and cupped his genitals in her hand. His achingly erect penis strained against the restraining nylon spandex of his thong as she squeezed and stroked the bulge gently. Her lips moved to his neck and shoulders while her other hand cupped his buttock and squeezed it firmly. Billie moaned and sighed and placed his hands on her back stroking the soft satin of her blouse and tracing the outline of the back of her bra. "That's very good. You sigh like a girl being kissed. Now take off my blouse and slacks." Jean enjoyed the sensation of holding his slender, effeminate body, which trembled as his desire soared. Billie was only the second lady-boy she had worked. They were both so horny. She suspected that Billie would have a voracious appetite for sex once it was released. Certainly, his sister did. She was the agency's leading escort. Jean had done a few conventions with Anne and found her eager to try anything. Jean was hoping that the weekend in Malibu would show Billie to be like his sister. The agency desperately needed another lady-boy. The demand for them was huge. Billie was very beautiful and emanated a torrid sexuality that would drive the clients wild. With shaking hands Billie unfastened the buttons of her blouse as she kissed his lips and flicked her tongue into his mouth. With mounting excitement he felt the smooth, warmth of her breasts inside the white cups of her bra. His breathing was heavy and coming in uneven gasps. He fumbled with the button and zip of her slacks and eventually loosened it and guided the garment down her thighs. "Now take off my panties, Billie," she said between wet open-mouth kisses. He slipped them over her bottom but something was preventing them coming down. He moved his hands to her front and found to his shock that she had a strapped on dildo. He paused and she took over pulling her panties down and at the same time pushing him back on to the bed. He lay back passively as she spread his nylon sheathed legs and stood between them. She looked feminine but also masterful with the black rubber dildo jutting aggressively from her groin. It was about eight inches long and a perfect replica of a penis and testicles. There was an open pot of cream on the night table and she spread this on the dildo. "Now you're going to have an important feminine experience. She pulled aside the crotch of his panties and pushed the tip of the dildo against his anus. He felt it spread his opening wide and he gasped, scared that it was going to hurt. He gripped her arms as his anus stretched and cried out as the tip suddenly overcame the resistance of his tight entrance and thrust into him. Impaled on the dildo he had a feeling of utter helpless. The sensation increased as she began thrusting the stiff phallus deeper into him. He closed his eyes and relaxed his legs. She hooked one arm under his right leg and bent it back against his abdomen. When she had fully penetrated him, he felt her abdomen slap against his buttocks with each thrust. "Uugghh! ... Mmm ... Oh God!" he moaned and cried out. His own penis was stiff and rubbed against the fabric of his panties. He was quickly coming to a climax. Three more deep thrusts and two days of incredibly arousing cross-dressing and his penis exploded. "Oh! I'm coming ... Oh ... Oooh!!" Semen gushed into his panties. As he came she thrust hard driving the dildo deep into him. The pressure of their bodies squeezed the "testicles" attached to the dildo and squirted fluid into his rectum. She grunted like a man having an orgasm and collapsed on top of him jerking and thrusting. It was a very credible performance and as sticky fluid oozed from his stretched anus onto the inside of his thigh he felt he had been fucked. "That was great ... Ummm. Do it again!" "Go and clean up and change into something sexy then you can try to get me aroused again." He went into the bathroom and sat on the toilet releasing the fluid from his rectum and cleaned himself. He took off his bra, garter belt and stockings, and panties and went into his bedroom. He slipped into a pink baby doll in a thin satin and trimmed with a marabou fur at the hem. He pulled on a matching thong and slipped on a pair of pink satin mules with four-inch heels. After putting on fresh mascara and a bright red lipstick dabbing perfume onto various erogenous zones of his body he returned to Jean's bedroom. She was in the bed in men's satin pajamas. The dildo was still strapped on her crotch. Billie slipped into bed bedside her and just as he had seen the woman in porn videos he began stroking her and kissing her lightly. Slowly he worked his way down her abdomen and proceeded to suck the dildo, moaning and sighing. After a few minutes of this, while she stroked his hair, she pushed him back on the bed and went down on his anus probing with her tongue. She avoided touched his very stiff penis which was safely tucked inside his thong. He desperately wanted her to fuck him again and found himself encouraging her to use his body. Her tongue felt wonderful and he wiggled and squealed happily as her mouth sucked on his anus and her tongue moved inside him. Things felt deliciously warm and wet down there. "Ooh that feels lovely ... Uuumph! ... Mmmm ... Oh ye ...es! Oh fuck me ... Unnnn I want you!" Two days of intensive feminization had done its work. He wanted to be penetrated. As she entered him he clasped his legs around her waist and pushed up against her thrusting pelvis, moaning and begging her to fuck him harder. She roughly swung him over onto his knees and drove the dildo into him from behind. She fucked him hard for 15 minutes and then unleashed the fluid spurting it into his expectant rectum. He screamed as she spurted. "You are a hot little thing, just like your sister," she said this as she slowly moved the dildo in his flooded rectum keeping him in an inflamed state. 4 - Work After one more day of Jean's tuition Billie was ready to audition for the fashion show. So absorbed had he become in developing his feminine side and transforming himself into as feminine a person as was possible that he had not given any more thought to the implications of going out to a private club to exhibit his feminine charms to twelve men who took a sexual interest in males with such charms. His natural competitiveness had risen to the surface and he simply wanted to be selected to prove he could do it. Jean's 'sexual' instruction had also had an effect. He had never had sex or any intimate relation with a female before Jean. She was the first and he was infatuated with her. He had slept with her for the last two nights and she had fucked him several times during the previous day. He was completely in her power - her sex slave. All the previous day she had worn the dildo under her slacks. On more than eleven different occasions, whatever he happened to be doing, she would seize him, fondle and kiss his body roughly, pull up his skirt and pull down (and three times tear off) his panties and fuck him usually from behind. Twice while they were out shopping she took him into a cubicle in a ladies toilet and fucked him. He loved it. He loved the way she handled him roughly, just taking him when and where she wanted. Each time she approached him his anus dilated expectantly. The result of all this was that he became conscious not just of his feminine bent for pretty things and a desire to look pretty but also of a certain female sexuality. Significantly, these initial sexual experiences caused him always to associate penetration with sexual fulfillment. Jean took him to the offices of a T-girl magazine and he was conducted into a photographic studio. Billie had dressed for the occasion in a gold satin sleeveless dress with a fringe hemline, gold sandals and his sexiest underwear, a flesh colored satin bra, matching panties and nude stay up stockings. The photographer introduced himself. "Hi. I'm Dan." "Hi Dan, I'm Billie." "That's a stunning dress - or maybe it's the body inside it?" "Thank you." The studio was dominated by a king size bed covered in black satin bedding. Two klieg lights stood at the foot and to one side. Video and still cameras on stands were directed at the bed. Dan picked up a third camera and began photographing Billie giving him rapid fire instructions to walk, turn, bend, swing, pout and so on. After 20 minutes he told him to remove his dress and get onto the bed. Billie had a glorious time rolling and vamping on the satin sheets. A hitherto unsuspected exhibitionist streak kicked in. He found it erotic to recline on the bed in a bra and panties, spread his legs and display his buttocks lewdly in front of a stranger. When he was told to take off his panties his penis stood out stiffly. He took off his bra and false breasts and pinched his nipples as he knelt on the bed wearing only garter belt, nylons and shoes. Later when Billie saw the prints he was pleased at how feminine he still looked despite the absence of a bosom and a cock standing up like a flagpole. Of course, he was chosen to be one of the models and on Friday afternoon he boarded the flight for Malibu. His ticket showed him returning late in the evening. Whatever Jean thought, he was taking Anne at her word and assuming that he was not expected to stay for the weekend. But once he was on the plane he began to wonder whether he would stay. His mind flipped back to Jean's dildo. He already missed it. What would the real thing be like? He had dressed in a white silk, long sleeved blouse with ruffles, a short, above the knee kilt in the Stewart tartan, a black velvet vest, black stockings and black pumps. Jean had picked out the outfit and thought he looked cute. He felt cute and sexy. He looked down at his legs. They were crossed at the ankles and bent sideways in the elegant pose, which Jean had taught him. He recognized that they were beautiful. He stretched out his hands and admired the manicurist's work. He had long false nails painted bright red and shining with polish. He was now used to the 'clinging' of the false nail glued to his real nails. Jean had assured him that he was very desirable and that pleased him. If he stayed he would find out how desirable he was. He did not meet the other two models until he found the chauffeur holding up the Club's sign in the arrivals lounge. They were standing beside the man looking nervous but very pretty. They were the same build as Billie but one was Asian with long shiny black hair and the other was Afro- American with ebony skin and a shaved head. They introduced themselves. "Hi, I'm Billie." "Hi, Billie. I'm Frances." Billie shook the hand of the black model. "And I'm Suzie." The three lady-boys followed the chauffeur to the limousine pulling their wheeled overnight cases, their stiletto heels clicking on the pavement. They had been instructed to bring one change of clothing, their make-up and some toiletries. All the clothes would be supplied. Shyness and tension ensured that the 40-minute drive was silent. Eventually, the limousine pulled into a long driveway, which took them to a huge mansion on the waterfront. Inside a T-girl in a black taffeta maid's dress, high heels and fishnet stockings met them. They were each shown to a bedroom. The pink and slate blue d?cor of Billie's room was bright and cheerful. The huge bed was upholstered in a matching pink satin. The drapes were made from the same material. Billie unpacked his overnight bag arranging his make-up on the dresser, hanging the blouse and skirt that he intended to wear on the way back in the closet and putting his lingerie into one of the dresser draws. In doing so he discovered a closet full of gorgeous clothes and drawers brimming with heavenly lingerie. It was a cross-dressers dream. When he checked he found that the clothes were all his size. He forgot that he was leaving that evening and wondered if there was enough time in the weekend to try everything on. A new T-girl maid in a yellow satin maid's dress interrupted his reverie. "Hi, Billie. I'm Nancy. Is the room suitable?" "Oh yes. It's gorgeous." "Good. Well the guests will be here in an hour. Could you come with me and we'll have a meeting about the show." Billie followed Nancy down the stairs into a large room dominated by three racks on which hung some dresses, gowns and lingerie. Beside each rack was a large table with open boxes filled with jewelry, bras, panties, nylons, and a wide range of accessories. Frances and Suzie joined Billie. They looked at Nancy. "Welcome to the Janus Club girls. The fashion show will start in 90 minutes. This is the changing area and you will each be assigned a dresser. They will be along in a moment. Now through here is the lounge area where the guests will be sitting. They followed Nancy through some heavy drapes into a comfortable lounge with several circular mahogany coffee tables with armchairs and couches around them. One wall was made up of large French windows, which looked out onto the ocean. "Oh! This is beautiful!" said Suzie. There was a boyish quality about the pretty Asian, which came through despite his white satin blouse, black dirndl skirt, and patent high-heeled pumps. "Yes, isn't it. Now see the different colored arrows on the carpet?" "Oh yes." We chorused. "Well, you follow the pink arrows Billie, You're blue Suzie and you're yellow Frances. You will all go out together and if you stick to your colors you will pass by the largest number of guests at the same time without bumping into each other." Nancy made them do a practice walk. Frances bumped into Billie and they giggled. Frances was wearing a long, navy skirt and a white mohair sweater with a silk scarf. He was almost indistinguishable from a girl. They did the walk three times. "Good. Now girls, this is a relaxed social event so I would like you to take your time at each table, introduce yourself to the guests and talk to them. Be friendly and get to know them. Any questions so far?" "What if they want to do more than talk?" asked Frances with a smirk on his pretty face. "I don't think I need to tell you what to do, sweetie. Follow your instincts. Yes, Suzie?" "How many changes of clothes do we do?" "First you will all wear a gown in the color of your floor arrow. After that you will wear two lingerie outfits." "Then what happens?" "All the members have paid to have private showings. They will chose which of you they would like to be their model and you will go with them to a private room for the sessions." "Do we have to do that?" Billie was getting worried. "No. After the session in the lounge you can let me know that you don't want to do a private show. Of course, you will not get paid the full $3000 and you will have to return tonight. But I noticed that you were booked on a flight." "Yes. I'm not really sure what I want to do. I've never done this before." "Jean told me you were new. Don't worry. You don't have to decide now." "Now follow me and I'll give you a tour of the house." They sashayed after Nancy on their stiletto heels vying with each other in trying to look excessively feminine. There was a lot of 'Ooos' and 'Aaahs' as they went from one splendid room to another. Each guest had a large bedroom and en suite bathroom. The beds all had satin sheets. "This is what we call the 'playroom'" This was a large comfortable but dimly lit room with a fireplace. Heavy drapes were pulled across the windows. There were a couple of armchairs and a sofa but mostly just large satin upholstered cushions scattered around. Billie did not see any games. There was however a TV projector and a large screen in one corner. "Well, its time to get dressed. I'd like you all to go back to your rooms, shower and shave, if necessary, and put on your favorite perfume. You'll find a housecoat in your closets. Put that on then come down to the changing area. You won't need your breast forms. You're just wearing padded bras. Off you go." Full of excitement they hurried to their rooms. On the way Frances and Suzie said they hoped he would stay. "It will be fun. I was here six months ago and it was wonderful." "But did you have to have sex?" "Of course! I didn't have to its just they could not have stopped me. With your looks these guys will go crazy about you, won't they Frances?" "Definitely!" "I wouldn't know what to do." "You don't have to know. Just relax and let them do the work. You just enjoy yourself." Billie was the first into the changing area. There he found his dresser, Sherri, an attractive but quite obviously male T-girl. He was wearing maid's dress in a pink taffeta. It had a multi-layered, white ruffled petticoat and a fitted bodice with puffy sleeves. He was very effeminate. "I'm Billie." "Hi Billie, I'm Sherri. Ooh! You are a pretty sissy." He slipped Billie's black satin housecoat off his shoulders and hung it on the clothes rack. Standing in front of him he clasped Billie's buttocks gently. "Ummm! What a lovely tush you have, sweetheart." Billie did not move away from the touch. He liked the soft silkiness of Sherri's dress against his abdomen and crotch. His small penis stiffened and rose up into the organza folds of Sherri's petticoats. Sherri kept his hand on Billie's soft ivory globes causing our hero to blush. "Oh, I just adore working on pretty boys and you are very sensual ... Umm ... and your skin is so soft." Billie shivered, less from being naked than in response to the blatantly sexual fondling of his bottom. Instinctively he moved closer to Sherri crushing the stiff folds of Sherri's dress. His penis touched Sherri's ruffled knickers. As Sherri's lips touched his Billie closed his eyes. They kissed lightly and slowly with open mouths. Although, clearly not a woman, Sherri's lips, scarlet with lipstick felt like a woman's. Billie felt the telltale dilation of his anus and a familiar weakness in his legs. He embraced Sherri enjoying the feel of Sherri's satin dress. As they broke their kiss Billie heard whistling and clapping. He turned to see Frances and Suzie, already in their bras smiling at him. Sherri whispered. "You are a hot little number." "I couldn't help myself." "I could tell, Sweetheart." He handed Billie a white satin, under-wired bra and a thong. "Put these on. Now you are all going to wear the same style of dress for the first go round." He held up a pink satin dress with a long straight skirt, an empire waist, a square neck and short sleeves. A satin bow accented the center of the bodice from which hung two long satin ribbons. "What do you think?" "It's lovely. I can't wait to put it on," Billie smiled. "Stockings first and make-up." Billie pulled on nude stay-up stockings with lace tops and slipped on his housecoat and sat at the dresser. Sherri handed him a pair of silver, ankle strap sandals with four-inch stiletto heels. After helping him fasten the straps Sherri did his make-up and kept Billie feeling very aroused by stoking his neck and ears. "You're lucky to have short a small penis. Is it always erect?" They both laughed. "It usually has been since I started cross-dressing and right now I think it likes what you are doing to my neck and ears." "Umm! Well see how it likes this." Sherri kissed Billie's ear and nibbled at his ear lobe. It touched a funny nerve and Billie squealed helplessly causing the others in the room to look at them. "Oh God ... That was too much." Sherri kissed Billie's lips with some intensity. "You and I are going to need some private time together, sweetheart. Give me your hand." He took Billie's hand and brought it under his petticoats and, pulling down his knickers, he guided Billie's hand onto his rigid cock. It was far bigger than his own penis and Sherri's testicles felt huge. Billie grasped the shaft. It was the first cock he had ever held other than his own poor excuse. He felt the sexual potential as the blood pumped causing it to throb slightly in his hand. "Oh! Its big." "Wouldn't you like to sit on that? Ummh! ... Feel it thrusting inside you? How about that?" Sherri raised his skirts so that Billie could see the very big phallus in his hand. Billie was speechless and transfixed by the size of Sherri's member, the intimacy of holding another man's penis, and the enormity Sherri's suggestion. "Put it in your mouth." Sherri pushed Billie's head down to his cock. Billie was drawn towards it and afraid. He was saved by Felicity, a T-girl maid in a red satin uniform. "Hey guys, let's go. We have five minutes." Sherri kissed Billie's lips and said, "later honey." Billie breathed a sigh of relief as Sherri helped him on with his dress, zipped up the back, gave some last minute flicks to his hair and handed Billie a posy of pink carnations tied with a satin ribbon. Billie forgot about the dangerous moment with Sherri as he became fully absorbed in the feel of his dress. He adored the way the satin flowed around his body as he moved. Felicity gathered all three sissies together for a little pep talk before they sashayed out into the guest room. Frances and Suzie looked cute in the same style of dress that Billie had on except they were respectively in blue and yellow satin with a posy of flowers to match. "Off you go girls. Remember to be friendly." Billie walked into the guest room and saw two men in tuxedos sitting in armchairs at each of the six coffee tables. Following the pink arrows he walked to the first at which sat two good-looking middle-aged men, one of whom was black. Billie said his rehearsed introductory speech. "Hi, my name is Billie. I'm 19 years old and a college student. I've been cross-dressing for two weeks." "Hi Billie," said the black man, "that's a very pretty dress. Come and sit on my knee." Billie had been told this might happen and so very demurely he sat carefully on the man's knees. Immediately he felt the man's hands roam over his body feeling his curves under the satin dress. The man's fingers touched a sensitive point in the small of Billie's back making him jump nervously. "Umm! You're a frisky little filly. His hands explored Billie's buttocks and thighs. Billie squirmed. Being felt like this was very erotic and Billie felt surges of desire pulse through his body but he was also unsure what to do. "Check this babe, Jerry." The man lifted Billie off his knees and set him on Jerry's knees. Jerry's hands felt Billie's body and he kissed and nuzzled Billie's neck. Billie felt Jerry's handclasp his genitals making him gasp. Billie squirmed as his body responded to the squeezing and stroking and his dress rustled and swished as he moved. He was becoming very horny and reckless. As he got up off Jerry's knees to go to the next table he saw Suzie and Frances being felt and kissed. Frances was laid back across one man's knees while the other man was kissing him full on the lips. Suzie's guest had his hand up under Suzie's dress. Both sissies seem to be enjoying the attention so Billie decided to relax and enjoy it too. It was at this moment that, barring something unpleasant happening, he decided to stay At the next table he sat on one of the men's knees without being asked . Before he could finish his introductory speech he was pulled backwards and kissed on his lips. Four hands explored his body, this time under his dress. His sex was squeezed and stroked and his anus probed with fingers. As each man in the room felt, probed and kissed him he became more and more horny. It took 30 minutes to complete the circuit before he returned to the changing area with Frances and Suzie. "Oh! God! I'm so ready to be fucked," sighed Suzie. "There's some gorgeous meat out there. I don't think the weekend is long enough," said Frances. "I saw you really getting into it with that Hispanic stud, Billie. You were really squealing." Billie remembere . The man had managed to insert two fingers into Billie's anus and Billie had wiggled on the intrusion gasping and crying. "Yes, I know. I was shocked at what he was doing." "You sounded as though you had gone to heaven." "Have you decided whether to stay?" "Yes, I think I will" "Oh good!" said Frances, "I can guarantee you will have fun." They went to their separate dressers and changed. Sherri helped Billie out of his dress and into a blue satin corset, black fishnet stockings and black patent pumps with four-inch brass spiked heels. He did not wear any panties so his small penis stuck out stiffly from beneath the frilly lace hem of his corset. Sherri fondled and kissed Billie as he helped him repair his make-up. Sherri was extremely aroused and Billie sensed that he could easily unleash a storm of passion if he gave Sherri half an excuse. He looked at himself in the mirror. The corset looked and felt incredibly sexy. He ran his hands over the satin panels. "What do you think?" "Sexy!" "You look very fuckable. Are you going to stay?" "Yes." 5 - Pleasure As the three sissies went around the room a second time Billie was acutely conscious of his role as sex object. The twelve men wanted his body. This knowledge gave him a strange feeling of power. He felt the sexual need in their bodies as they kissed him. He kissed them back more actively, opening his mouth and letting them explore with their tongues. Billie fondled their ears and necked as they kissed encouraging them. With his penis exposed each man fondled and stroked the hard spear of desire. Several men kissed and sucked it causing Billie to moan with pleasure. Billie held and stroked all of their cocks. Most were between six and seven inches long but two where very long, at least nine inches. The black man had the longest. It was straight and hard. Some were curved up and three were too thick to get his fingers arou

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Schools are fun for most of the students. They study together, play together, eat together and learn all kind of things in school. And for some of them, the school become there unforgettable memory. The memory they would cherish forever. My memories of school are also unforgettable... but in a painful way. I was the an earnest student. 'Good in everything' this is what my teachers used to say. Academics, sports, curriculums, I was good in every field. Always the center of attraction. Always the...

1 year ago
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An Exchange Student

An Exchange Student By Paul G. Jutras In what was otherwise a typical peaceful block, there was one menace. Fourteen year old Chris Jones. As the sounds of his skateboard headed down the sidewalk, everyone in the way was moving aside as fast as they could. Some climbed street lamps and others leapt into near by stores. Those who couldn't make it were bowled over like a bunch of pins at the end of an alley. Those laying there looked up and saw Chris karate kick a garage can into the...

2 years ago
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The Teacher and the Student

A busy Thursday had found me in the library café, with what must have been the tenth cup of coffee I’d consumed that day. I was struggling mightily to focus my attention on a depressingly thick stack of books and material for my classes. It was my own fault for electing to write a thesis this year, I thought to myself.At least they kept the place nicely heated. Even though the harsh winter winds rattled against the windows, I shed my jacket, sweater, and long-sleeved tee, leaving just a tight...

Straight Sex
2 years ago
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The New Student

There is a theory that girls make better students than boys do. This the story of what happened to me when I started at college (OK - some details have been embellished here and there)... When I gained a place at University, my mother was worried about where I would live, and within a few weeks announced that she had arranged with a family friend for me to have a bed-sit. "Apparently there are a few other students in the house, so you won't be lonely," she explained. The weeks passed...

3 years ago
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My Teaching Sexcapades 8211 Pt 1 Seducing Shy Student

Hi all the good people of ISS, it has been a long gap since I wrote on ISS because of various reasons. I was having fun with my new role as a lecturer but the site was blocked so I couldn’t. But since we are back online, I want to bring you my new experiences as a lecturer and sex teacher. I am Kishan from Bengaluru and I am the hero of this story. This is only the first part of the series I am about to write. After working in a private sector for a few years, I got bored with the mundane life...

2 years ago
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My Affair with a Student

Jaime was so attractive that I knew she would be a distraction.I’m a thirty-year-old high school chemistry and biology teacher. Chemistry is a senior-level class, so all of my chemistry students are seniors, and around eighteen years old.This year’s chemistry lab was full, but there was an odd number of students. Since I always pair the students for the lab and the curriculum is designed for two students working together, that one odd student would have to work by herself and would come to me...

2 years ago
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Daniel Effeminate College Student

Chapter 1The BeginningDaniel, an Italian boy in his late teens is starting a fine arts program at a college in the US. He had been awarded a full scholarship as part of an exchange program with the international arts community. He arrives before classes begin and has to stay in a hotel at his expense as the residence on campus in not available for a week. He is happy to be there as this is freedom for the boy as he can now begin to express his true desires to be gay and effeminate. At home it...

3 years ago
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Sexy student

Hello ISS readers my is Divya & I live in Mumbai, I read ISS. And by fascinating I am writing first story of mine. I am 28 yrs old now widow and in search of sex partner, I am a lecturer by profession in one of the classes in Mumbai . My husband was a Govt. Servant & died two years ago. I first enjoyed sex when I was 18 with one of my student who was use to come for tuition at my home. I have lesbian experience with two female lecturers who are working with me in the same Classes. The story I...

4 years ago
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The Old Professor vs the Young Student

The Old Professor vs the Young Student By MinxGirl and billy69boyI had been teaching at the university for some 30 years, and I had never encountered such an intriguing vision as Soleil in all my days. She is a beauty, and an enigma. She was breathtakingly refreshing and very frustrating…beautiful, yet exasperating. I came to be rather obsessed with this 20 year old vixen from the first time I saw her in class, just something about her that caught my attention: she was half Thai, and half...

1 year ago
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Sex with madical student

I hear my name being called as soon as I set foot on the sand. It was a vaguely familiar female voice from a distance. I looked towards the direction and saw someone in the water with her head just visible. I walked closer and recognised her instantaneously. She was a medical student whom I have taught a few years ago."Dr Young, how nice to see you here! It is Fiona, do you remember me?" She said with a genuine warm smile on her unforgettablely attractive face.Of course I remembered her for she...

2 years ago
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One failing student

My name is Tonya, I'm 5'3 with C-cup breasts and red hair. I'm 28 and I teach math at a community college. I have one student who keeps failing quizzes. I handed back a quiz and he didn't do so well on it, but I came up with an idea on that Tuesday when I gave it back to him. “OK class dismissed,” I said to the whole class. Then he came up to me wondering about his grade. “I can't believe it, I could have sworn I got all this down,” the student, Jack, said. Jack was 22 and he was 5'11 with...

Straight Sex
4 years ago
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My Student

Class was over. All of the students (at least all that had bothered to show up on the day after the test) rushed out quickly. Dr. Vincent Prins knew that Math 090 was not a popular course, and the people who liked math never ended up in this class. But he strongly felt that introductory courses, even remedial ones, were really important. Let others glory in their upper level math whizzes, he gloried in every student who passed the course. On four of the tests, he had written ‘Please stay after...

2 years ago
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The Exchange Student

Her thick moist lips tightened around my shaft as I exploded deep in her mouth while I worked frantically over her clit with the tip of my tongue to...... Ah yes there it was, her trade mark gush of lady jizz, I took in as much as I could trying to follow the movements of her convulsing body so as not to waste a drop. “Time to get ready for school B” Trina smiled. What a way to greet the day, surely I was the luckiest man alive. Trina and I showered, dressed and drove to school together. At...

4 years ago
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The Ideal Student

The Model Student  The Ideal Student By themaneloco I have absolutely no idea what I was thinking!? I guess I could just go with the classic clich? ? it was a good idea at the time.? A good idea it was, but it certainly wasn?t my idea, at least I didn?t think it was.? You see, I am a first year student at a respectable university studying mathematics.? Of course, my parents are very proud of this, as am I.? They knew that I was destined for great things from an early age and, along with t...

2 years ago
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Mrs Greens Problem Student

Mrs. Green's Problem Student By Kelly M. Hello Kelly M. Here. I just wanted to say think you for the support you havegiven my via email I really appreciate it. I tried to return all the emailsthat I got. A few were returned to me because the address that I got were undeliverable.If you have any comments or questions I would like to hear from you. My emailaddress is [email protected] Thank you to Aria, Couture and DP for proofreading and editing. I really appreciateall you have done for...

4 years ago
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The First Male Nursing Student

The First Male Nursing Student Chapter one Hi! My name is Suman and this is my story. I come from a middle class family. During my school, I was relatively good in studies. So like any other good student, I dreamt of being a medical doctor someday. I finished my school with relatively good marks and started to prepare for the MBBS entrance exams. However, entrance exams were not something for me. Despite my best efforts and waiting for two years, I was unable to achieve a seat in...

3 years ago
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My favorite student

I figured out he was getting  an impressive sight of a brown big ass, eager to get fucked, bent over as I was now.  Those vagina lips were so big they hung down, like purple. I begged him to put his dick in there, but had to guide myself his cock head at the entrance, so this inexperienced, innocent young guy only had to thrust inside. Oh, how good it felt, until he cum into me! His hot cum made me feel a smarting sensation,  a sting inside my ass. Finally, we lay down there, exhausted, and...

Mature
4 years ago
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Seduced kitu my student

Hi iss readers this is manu from jaipur. I am 28 yrs old guy with good physique, and all skills and abilities to satisfy women’s sexual needs. I will give my contact further. Now my story starts when i was 22 yrs old passed out my engineering recently and i was trying for further studies so i was at home after the college. I was a good student specially, good at engineering drawing. Then my aunty told me will you teach a student in first semister of engineering and she is frightened by subject...

2 years ago
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Me And Chinese International Student

Hello friends I am big fan of Indian sex stories and I am sharing one of my experience. I hope you all will like this. My Name is Jolly Singh (name changed) and anyone wants to leave any comment they can do that on on messenger and I will reply on that. I am mature male 42 from Sydney Australia of course Indian settled in Sydney. This experience which I am going to share with you happened 12 yrs ago when I was 29 and virgin. I was international student here in Sydney and was also working in...

2 years ago
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Leaves Wife for College Student

Julian is a thirty five year old car designer living with his wife Michelle a thirty five year old receptionist who he has been with since they were both eighteen.Despite being together for s*******n years they started to have problems, Julian wants to have c***dren but Michelle doesn’t want c***dren at all. Julian has now been begging Michelle for a few months now for them to start a family however he starts to feel a bit unwanted around her and did consider leaving her at some point.One night...

3 years ago
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The Professor and Her Student

Elizabeth Mae Starr was a bit frustrated The Professor and the Student oliverc [email protected] Author?s Note:? This covers some familiar themes, but if you read it, I enjoy the feedback either through reviews or email.? I have incorporated some suggestions from previous reviews into this one, but ultimately it speaks to my fantasies.   Professor Elizabeth Starr was a bit frustrated.  She had not had any sex for three months since her lover left town for a new job in a...

3 years ago
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The Anthropology Student

Suddenly the sound of footsteps startled her and she quickly turned around. Just coming into the room was an older man with short gray hair and mustache. He was tall about 6'4” with an athletic build and tan weathered skin. Professor Hiram Jackson was the head of the archeological dept. in charge of this site. This dig in the middle of nowhere Wyoming seemed to be the home of a previously unknown tribe of natives. It consisted of himself, his best student Allison, and 20 other students and a...

3 years ago
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A Gift for the Gifted Student

Gifted student sounds a little not PC. But that is what we called ourselves. Accelerated student might be a better way of putting it. But none the less we were very smart k**s and the school district wanted to make sure we did not get bored and go some where else so they came up with these special events and classes and field trips for us. I mean there were only ten of us in the program. I was excited about this trip to the city for a week. We would get to stay at a fancy hotel and go see all...

1 year ago
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Bright Student

"Sir, I just can't understand this problem" Nisha walked in wearing a harassed but determined look she landed on a nearby chair. she was a charmer and the brightest student of my class, she is studying for prestigious IIT exam and i am proud to be her teacher, her sheer genious and a very determined personality is sure to bring great success in her career. "It is 10 PM, Dear can't it wait for tomorrow" I tried a feeble attempt of getting away, it was a long day and i am taking IIT coaching for...

Erotic
1 year ago
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My Hot Student

Hi friends Rahul again for all sex story readers. I am sure u have read my previous stories and like a lot, pls give me feed back at rahuldelhi.roy at gmail dot com, lets start the story. This in a story of my sexual interaction with my sweet and innocent student. I was a student of B.Tech final at that time and I use to teach accounting to girls at their home, as girls pay more than guys and offcourse a free fun with them which a hot guy like me never avoid. Rani is my student who is studying...

Erotic
1 year ago
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Sexy Student

Hi friends Dani again for all sex story readers. I am sure u have read my previous stories and like a lot, pls give me feed back at silent_magma [at] hotmail [dot] com, lets start the story. This in a story of my sexual interaction with my sweet and innocent student. I was a student of CA final at that time and I use to teach accounting to girls at their home, as girls pay more than guys and offcourse a free fun with them which a hot guy like me never avoid. Rida is my student who is studying...

Erotic
2 years ago
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The Cheating Student

His name is John Preston and he happens to be a professor at at top of the line school where the students practically teach themselves. Professor Preston prides himself on having some of the best students on any campus. On a warm and sunny spring day there appeared to be no clouds on John Preston's horizon until he was approaced by a test proctor. "Excuse me Professor Preston," the proctor said with a gim faced look. "I am sorry to say that I caught one of your students cheating on a...

2 years ago
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A Good Student

A Good Studentby Dr. MabeuseChapter 1Writing fiction doesn't pay much, and you give up a lot when you try to be a writer. Money, the things other people have, even family—you can pretty much kiss all that goodbye. But there are compensations. Your life's maybe not as wide as most people's, but it's deeper, and sometimes it’s more interesting. You're always trying to explain and describe things to yourself, and so you see things other people miss and feel things most people are too busy to...

4 years ago
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A Brilliant Student

Berkeley had even granted her her own personal lab (which she had partially funded herself) and offered her a special program that allowed her enough time for her research projects during her Masters. The lab was something to behold. Whiteboards filled with chemical formulas, Lewis structures and skeletal diagrams. Hundreds of containers and thousands of vials with all kinds of chemicals inside. Dozens of fridges and ovens and various specialized fume hoods, some even equipped with robotic...

3 years ago
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Mr Ks Favourite Student

Jen had been at the school for 5 years, she was a complete brain box, she knew the answer to every question, and every teacher thought of her as a model student. I joined the school in year 8; all that time ago, we barely knew each other, we’re not that close now, just good friends. It’s year 10 now, things are getting scary as we realise it’s just a year and a half left till we sit our GCSE’s. There was one more thing about Jen, she was stunning, not so much in school, so most of the boys...

3 years ago
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Sex With My Computer Student

Hi all to ISS readers and thank you all for giving responses. This is Kkb from Lucknow. This is my second story in ISS, hope you all will enjoying. Hoping you have read my first story ‘Sex in Computer Institute’. Here is my second real story. Yet another with my one of student. This instance occurred few months earlier my previous instance in Computer Institute. I was a computer teacher in my first institute. I am directly coming to the point. There was a student girl and having interest in me...

2 years ago
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The New Student

The New Student - Chapter One - Scarlett Green The weirdness started on September third, 2018. It was the first day of my final year of senior school. In the following May I would be taking my final GCSE exams where I would then hopefully go on to college to do A levels for two years before moving onto University. I had just arrived at school and about to enter registration before the day of lessons would begin when I got a text message from my mum. It was a group message that had...

3 years ago
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Gay sex with student

Hello, I am raghunath from andra pradesh, Hyderabad. I am now aged about 55 years. While I was 45 years, working at Vizak in private sector, this incident happened. As per the govt decision my organization started plantation of trees to make the city green. For that I approached to a junior college and met with the principal and expressed the matter and requested to send a batch of students to participate in plating trees. I have invited forest authorities also to participate in it so that...

Gay Male
1 year ago
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The New Student

My Wife’s Student It was already raining when I got home that evening so I headed straight to the bathroom on entering home. My wife was sitting in the living room with two ladies, one elderly and the other presumably her daughter. They wanted to learn some new art style and from what I gathered while taking off my shoes, the girl was going to join for Impasto knife painting. While passing them I had a cursory look at the ladies and I saw the girl staring towards my wet jeans. She must have...

Erotic
1 year ago
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My Favorite Student

Exams were done. Another graduating class had been sent off into adulthood. Now, I had about two months of summer to not deal with students. Don't get me wrong. I loved being a teacher. But summer vacation was always something I looked forward to. As I packed up stuff in my room, I thought about some of the seniors I had this year. There were always some very lovely ladies in my classes and while I very subtly watched them I never actually did anything with them. That didn't stop me from having...

Interracial
3 years ago
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Summer Voodoo

Continuing the Summer saga, this story picks up where "Summer is Hot in Cozumel" left off. "So, John, what's the deal with you sexually propositioning Aaron?" "WHAT?!" Grinning, Summer poked him in the ribs. "Don't try to deny it, you glorious freak. I heard you on Dave's phone call, trying to talk Aaron into helping you join the Mile High Club." John leaned back and laughed, "Oh god, you heard that? Okay, fine, Summer, you're onto me! My secret is out!" Still grinning,...

3 years ago
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Summers Story

The two of them walked through the double glass doors of the convenience store with a whoosh of wind following them, blowing through the center aisle way next to the service counter, magazines and pages flipping through the wind. There was no one else there but Jeff, the clerk working the register, who at the moment was using the customer restroom on the other end of the convenience store. The cameras were the only things that caught them at first.One was male, tall and skinny, seemed to hide...

4 years ago
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Summering in Femininity Part 12 Summers End Continued

The next morning, a Saturday, Taylor was awoken by a gentle knock on his door. He sat up to see Aunt Agnes waiting by the door. "Is something wrong?" Taylor asked, yawning. "I was about to ask you the same thing, Emily hasn't come by yet and I got worried," Aunt Agnes stepped into the room. "Worried? Why?" Taylor reached for his phone and realized that it was nearly noon. "Wow... She let me sleep in?" "Did you two have a fight?" Aunt Agnes asked. "No," Taylor replied. "I...

2 years ago
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Painted Student

Painted Student   Lunch time in the refectory can be hectic. Students and staff share the same facilities, queuing for hot meals or panini’s and coffee. It isn’t the largest room in the college so, the tables and chairs can become precious, especially when they are pulled out of their serried ranks into group patterns so friends can socialise while they eat. Today was just like any other at lunch, hectic. The place heaved with a mass of young people whose voices joined in a cacophony of...

4 years ago
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The Exchange Student

The Exchange Student By Robyn, the GIRL Wonder CHAPTER ONE: SATURDAY NOON ?Come along, Zoe, dear,? Renee taunted. ?Oh, yes...come on down, where we can all see you,? chimed in Tina. It was my sister Melissa, at the top of the stairs, that gave me a little push. ?Your public awaits, Miss LeMercier,? she giggled. There was nothing else I could do, you see...so I obeyed. Here I was, a fourteen-year-old boy, with curled blonde hair, in white leatherette high heels, wearing flesh...

1 year ago
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AGrade Student

desperate student wants to improve her grade, a dirty Professor is only too happy to oblige...The snow fell slowly that afternoon, drifting in flurries over the fields and forests, and settling in large, powdery drifts against the venerable buildings of the university. From his window, looking out over the manicured gardens of St. Stephen's Quad, Professor Lucas Wainwright watched the flakes whirl and settle, and he smiled. This, truly, was his favourite time of year - partly because of the...

4 years ago
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Painted Student

Painted Student   Lunch time in the refectory can be hectic. Students and staff share the same facilities, queuing for hot meals or panini’s and coffee. It isn’t the largest room in the college so, the tables and chairs can become precious, especially when they are pulled out of their serried ranks into group patterns so friends can socialise while they eat. Today was just like any other at lunch; hectic. The place heaved with a mass of young people whose voices...

First Time
2 years ago
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Summering in Femininity Part 1 A Bummer Summer

A Bummer Summer? It was the dream of every seventeen year old, during the summer before his senior year of high school to spend it miles away from all his friends and all his stuff. In case you couldn't tell, that was sarcasm, because for Taylor Hughes, that was the last thing that he wanted. Unfortunately, he had no control over the matter. His parents were going out of the country on business for the entire summer, and trying as he might, Taylor was unable to convince them to let him...

4 years ago
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Summer Is Hot in CozumelChapter 3

"Aha! I see you found the old tank top," Dave said, hugging Summer from behind as she stood at the kitchen counter chopping potatoes. Wrapping her arms around his, Summer smiled. "Did you think there was any chance I wouldn't? I'd already found it way before you left your phone message." "Well, I was right, you do look absolutely amazing in it." "Thank you, sweetie. I'm glad you like it on me. It's shorter than that little nightshirt you love so much, which at least sort of...

4 years ago
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Summer My Sisters Best Friend

This is a Summer Lovin’ contest story. Please vote. * Stephen’s love of his life is his sister’s best friend, Summer, a woman eight years older than him. Summer, I’m in love with Summer, my sister Christine’s best friend and I don’t know what to do about it. Love at first sight, it all started the first time I saw Summer in the summer of 1968. She was in the backyard with my sister in the pool. As if my sister was swimming with an angel, a woman with a model’s face and a porn star body, I...

3 years ago
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Summer Is Hot in CozumelChapter 1

"Jake, promise me that I'll never wake from this dream..." Sighing contentedly while pulling our light blanket over us, she hugged herself against my bare chest. Once she was all settled in, I wrapped my arms around her slender shoulders and kissed her forehead before giving my happy girl a gentle squeeze. Summer and I lay together on our back porch, staring up at the brilliant starry night sky of Cozumel. She was curled in my lap, purring like a kitten. Bathed in soft, warm candlelight,...

1 year ago
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Summering in Femininity Part 9 Three Cheers for Taylor

One of most annoying things about Emily, Taylor had decided, was her sleep schedule. So far, he'd been able to avoid her morning jogs, but she was always at the door right after, far earlier than Taylor would have liked. And unlike Logan, who unfortunately (or fortunately, given Emily's repeated hinting that Taylor had a crush on him, despite his objections) had other obligations most of the time, she was free to drag Taylor wherever she wanted to go, usually the mall. Taylor's happiness...

4 years ago
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The Older Student

It was the start of another academic year. I had been teaching the upper division courses but was asked to teach a College Algebra Class for this term. I was looking forward to doing so as I had heard how ill prepared the students were. Most of the incoming students must take remedial course work due to their low understanding of mathematics at the major university where I teach and I wanted to see just how ill prepared they were. I waited in the classroom for my students to start arriving to...

2 years ago
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summer 2

Lilly talked for the both of us asking each of us questions and going on about her day until I heard mom say (to Lilly) "did you hear about the new Nudist beach their building over in Balsam?" I swallow my anger and ask "how come their building a resort there,there's no beach on the lake except in the park right?" Mom looks at me and says "actually there's a sand bar on the side of the lake grandpas house is on" I chuckled and said bet the Ryersons be all excited about that" mom...

3 years ago
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The tutor and his student

Introduction: A middle aged tutor teaches his student more than just trig and geometry I was a adjunct professor at a local community college after switching career paths. Forty-five may seem like an odd age to change careers, but I was unhappy as a consultant and wanted a change. Adjuncts dont typically make a lot of money, so I tutored on the side. My specialty was math and prep for college entrance exams. It didnt pay great, usually about 25 dollars a session for an hour, but it helped out....

2 years ago
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Student

Our home in Kensington was realistically too large for the two of us but of course its all about image, I knew of a couple of neighbors that were struggling financially but of course they had to keep up with the Jones's. One of the neighbors knowing we had plenty of room suggested that we might take on a Uni student as a guest, the house had a guest room out the back so after talking it over we agreed it wouldn't encroach on our lifestyle so there was no reason we couldn't help out a...

3 years ago
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Stud student

Hi I’m Samuel a university student from Uganda in the first year of studying law, I came to this country because my country, does not have a great education system, arriving in England I set about getting lodgings close to my study area, applying for a room with a white family I went and viewed the room, Sandra was married with 4 c***dren Sam a fireman, Pat a postman, Carol a manageress at the large clothes store in town and Frances who lived in Australia, yer I know postman Pat and fireman Sam...

2 years ago
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Exchange student

It was my junior year of high school, there was an exchange student program between our school system and under developed countries. I was summoned to the front office and introduced to a student from nation of Liberia. He introduced him self as Omagelia Ado, it was his first trip to the USA and his second out side of his country of origin. I was to show him around the school and have him back at the office no later than the start of the last class. There was a car there to pick him up and...

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