Military School Crosdresser free porn video

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MILITARY SCHOOL CROSSDRESSER By Kresha Matay PART 1 Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of Joe, his father. The father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim couldn't measure up to the desired image. Joe had expected his son to grow up to "be a chip off the old block" and when he didn't, his father felt "cheated". Tim might have grown up the way his father wanted if he hadn't contracted Polio at the age of eight. The youth was paralyzed from the waist down. Though he did completely recover the use of his legs through a long series of operations and physical therapy, the doctors felt his growth had been impaired. He would never be as big or as strong as he might have been. Due to his illness, Tim also missed a lot of school and was two years behind his age group. These shortfalls caused the father to ridicule his son whenever he failed to satisfy the man's absurd notion of what his child should be like. When this occurred, Tim sought consolation in the loving arms of Rita, his mother. Here he found the love and emotional warmth he so badly desired. This only added to his father's frustration and reinforced his resentment against both his "sissy" son and his "coddling" wife. This hostility was augmented by the "darts" Joe received from his macho chums at work whose sons all played Baseball and Football. His constant bitterness manifest itself in a pattern of physical, mental and emotional abuse against both the mother and son. As most often happens, the mother, protecting her only child, transferred her love from the husband to the son and viceversa. Tim, now in the initial confusion of puberty, misunderstood his mother's attention and developed a strong personal attachment to Rita, her belongings and more specifically...her clothing. Any personal item of his mother's became a symbol of the good things in life to the confused youth. Everything that belonged to her was pretty or beautiful or made him feel safe, "warm and fuzzy". Everything that belonged to his father was rough, ugly, caused him pain and got him into trouble. He rationalized, if he had been born a girl, he wouldn't have been expected to be knowledgeable about cars, guns, sports equipment or tools, all the things he hated. This eventually led him to secretly playing with his mother's personal items. One day, he took his mother's underwear from the clothes hamper. Dressing up as a girl, he fantasized he was Rita's daughter instead of her son. He so thoroughly enjoyed the fantasy that he repeated his actions every time he was alone. With each new incident of crossdressing his fantasies evolved till he developed a second persona as Sarah...his mother's daughter. As he grew older, Tim found he enjoyed the crossdressing more and more along with the emotional excitement he derived from it. One day while performing a surprise cleaning of his bedroom Tim's mother discovered an assortment of her recently "misplaced" lingerie hidden inside her son's pillowcase and between his mattress and the box springs. Realizing how they must have gotten there, she suspected he used the lingerie for purposes of arousal and masturbation. Amused and concerned at the same time, she decided to confront him. That afternoon, upon his arrival from school, she called Tim into her room. Rita, holding up the confiscated lingerie in her hand, said, "Young man, would you explain why I found my lingerie hidden in your pillowcase and under your mattress? I'd certainly like to hear what possible justification you might have that would explain how it got there, why you've hidden it there, and what you wanted it for in the first place!" Confronted with the evidence, the youth broke down in tears, admitted his crossdressing and explained the fulfillment he derived from wearing her clothes. Holding nothing back, he declared how badly he wished he were her daughter instead of her son. The intensity of his desire to be her daughter surprised Rita. His confession projected not a simple fondness for her clothes as she might have expected, but a sincere desire to change his gender. Rita, in an effort to discover how deep his desire ran, began asking a series of disguised questions. The answers ultimately convincing her of Tim's sincerity and more critically...his desire to be female. Assuming he would continue to borrow her clothes and crossdress no matter what punishment or corrective action she enacted, Rita decided that the best course of action was to allow him to pursue his crossdressing, but under her protective guidance. Afterall, she mused, "The remedy is more likely worse than the actual problem." She secretly "felt" he might eventually outgrow his fetish as the novelty of wearing her clothing with her consent wore off. Rita's decision was partially influenced by her absolute certainty as to what her husband's ugly reaction to Tim's crossdressing would be. She promised Tim she would keep his secret from his father, but warned him to be more careful in the future. Rita demanded his promise that he would crossdress only when his father was away from home and only in her presence. Tim enthusiastically agreed to her demand when Rita offered to teach him how to dressup and also offered part of her wardrobe to him as his own. Over the next three years, she kept her promise by presenting him with various feminine attire including dresses, skirts, blouses, high heels, a pantygirdle, nightgowns, breast inserts, panties, slips, nylons, bras, pantyhose, garterbelts, costume jewelry, makeup and even a long tressed blonde wig. These were kept in her clothescloset (by this time Rita and Joe were sleeping in separate rooms), with the understanding that they were really Sarah's to enjoy. As his secret crossdressing became a larger part of his life, his mother's involvement also increased. Rita came to realize how much happier both she and her child were when he dressed as her daughter. Deciding his life, as a boy was miserable enough, she began to encourage Tim to become feminine more often. The next level in her son's transformation was natural and easier...she assisted Tim in his attempts to mimic the gender differences. Now she used all their free time teaching him feminine mannerisms. She trained him in the art of applying makeup, coached him to speak with a higher, yet softer, and gentler voice, becoming his gender tutor. By the time he graduated junior high (at the late age of eighteen), he could comfortably pass as her lovely young daughter. Tim could mimic the way a young woman walked, talked and presented herself. He had mastered all the subtle mannerisms that differentiated the genders. When dressed in his feminine raiment, he truly became his alter ego Sarah. All this occurred without the slightest knowledge of his abusive father. His mother, who had always wanted a daughter, now found an answer to her lack of one. Whenever her husband left for an extended fishing, hunting or business trip, which was quite often, Tim would spend the entire timeframe dressed as Rita's daughter. As soon as her husband's car pulled out of the driveway, Rita would call Tim to her bedroom and transform him into the lovely Sarah. They would pass the whole time just as any other mother and daughter. As Tim grew within the role, they ventured outofdoors, taking short trips into the real world. At first, these were car rides late at night, with little chance of discovery. As they both became more confident with his ability to pass, they added short stops at McDonald's and other fast food restaurants. The next logical progression was running errands as mother and daughter. With each new success came more daring adventures. One momentous day Sarah and Rita decided to go to the mall for some shopping. The day was a total success! They shopped all the women's stores, taking great pleasure in Sarah's ability to "fool" the saleswomen. They tried on dresses, bought new lingerie, bought high heels, bought cosmetics, had lunch in the food court and took in a movie as they thoroughly enjoyed Sarah's newfound freedom. After this successful outing, they went everywhere as mother and daughter. No fears, no concerns, truly comfortable within their characters. Two females going to museums, art galleries, restaurants and theaters like so many other mother's and daughter's. If there was a good play being performed, that's where they would be found, dressed in their finest feminine attire, reveling in their joint womanhood. At home, in the evenings, adorned in their silky negligees, Rita spent hours talking about her life as a young girl. She told Sarah stories about her girlhood, her dates, her first kiss, her first love and the first time she made love. They sat for hours like other mothers and daughters, talking about clothes, hairstyles, makeup and how marvelous it was to be female. They would nervously giggle and laugh at the idea of Tim's father finding out about "Sarah". Their conversations included such topics as how his mother felt as a woman. What her dreams and fantasies were and had been. How she viewed men and how she felt about her marriage to Joe. Each time they chatted was another learning experience for Sarah. The information Sarah's mother related provided her with a superior understanding of the feminine gender, i.e., how the female mind worked, what were the "precepts" of womanly conduct and how his mother viewed her status in society. One evening, when Tim asked a question about female sex organs and how they functioned, Rita went to Joe's bedroom, opened her husband's dresser drawer and extracted a few of his "hidden" girlie magazines. Then using the most explicit pictures of the absurdly posed models she described all the erogenous areas of the female body and the passion women derived from loveplay. Having gone this far, it was a small step for her to describe the various techniques that excited a woman. She explained how most men expected their own sexual satisfaction without concern for their partner. This occurred because men felt superior to women and how stupid an idea this was in reality. "Women should always be treated with the greatest respect and should never be used as a sex toy! All the courtesies and culture that make up human civilization are the results of female efforts to make our lives more beautiful and more satisfying. I want you to always remember, almost any male can father a child, it takes a woman to give the embryo life, to nurture and carry the child in her womb as it develops and then when she gives birth the future of our civilization is guaranteed. That's why I expect you to always regard women with honor, reverence and esteem." While Rita felt totally comfortable discussing any topic with her daughter, she remained guarded in her dress. Though she assisted him in his transformation and at times they helped each other get dressed, she never allowed either herself or Tim to be totally nude in front of the other. They did, at times, walk around the house in panties and bras, but that was as risqu? as they got. Theirs was not a sexual situation, but one of love and understanding. PART 2 This closeness between the two and Tim's girlish traits didn't altogether escape the notice of his father. While their secret remained hidden from him, he now thought his son was turning gay. Joe decided that Tim needed discipline and physical training to "make him into a man". When Tim was eighteen, he was sent to a military boarding school to finish his last two years of high school. Rita protested most vehemently but to no avail. Now Tim's life changed dramatically. He was still the subject of daily ridicule, but now it was the other male students, not his father who mocked the wellbred boy. The other cadets instantly recognized and made fun of his gentle voice, mannerisms and polite attitude. In addition, he no longer was able to escape into his other persona...Sarah. As the days went by, he withdrew from all contact with the other boys at school. One Saturday morning, when most of the other students were home on weekend leave, he stayed rather than go home to his father (Rita was away). He decided to walk over to the main building to get change for the Coke machine. This was his first time inside the offices of the school. He had, of course, noticed the female secretaries when they walked to the cafeteria (all the boys had, since they were the only women around), but had never spoken to any of them. As he opened the office door, he was run into and knocked over by the two small sons of one of the secretaries. The woman ran over to see if he was hurt at the same time yelling for her kids to, "Stop!" "Are you hurt? No! Good! Please excuse my children, I brought them with me because I couldn't get a sitter and I have all this paper work to finish by Monday. I don't know how I'm going to get it done and watch them at the same time. Oh, I'm sorry, I'm Mrs. Kinzie and these two rascals are my son's Jeff and John." Tim introduced himself, then said. "It's a pleasure to meet you Mrs. Kinzie. If you need someone to watch the boys, I'll do it. I'll take them to the gym where they can run and chase as much as they want and won't be in your way, so you can get your work done." This offer was met with cheers from the boys and after a slight hesitation, grateful acceptance from their mother. In the course of further conversation, Mrs. Kinzie suggested he call her Jean, at least when none of the school officials or other cadets were around. When Jean offered to pay him, he graciously refused her offer. After Tim and the boys left, Jean returned to her desk, but instead of resuming her work, she thought out loud. "He's not like the other students in this school. They wouldn't have offered help to one of us secretaries. They're so stuck up and "macho" they only stare as we walk by while making indecent gestures behind our backs. He's different, more sensitive and much more responsible than the other students. I wonder how he manages to cope in this milieu? If he stays that way, he'll make some girl a wonderful husband and probably a great lover. Not like that insensitive bastard I married! I hope his new wife gives him what he deserves, a whip across his ass. That's just what he needs to teach him respect for all women!" Jean was a strikingly beautiful and sensuous woman of twentytwo. Her classically molded features, crowned by a mass of auburn hair, were complimented by the firm fullness of her breasts, flat stomach and carried by two lovely defined legs with finely turned ankles. While some of the other secretaries might have appeared sexier (they wore more revealing clothes), she was the one who constantly received requests for dates, but refused them all. Being a working mother, a surrogate father and raising the boys left her little time for a social life. Also, being "used" by another male was not a goal she desired. When sexual frustrations reached a peak she could no longer control, she shamefully fingered herself to an orgasm. Of late, it was getting more and more difficult to reach fulfillment, also her needs seemed to return quicker. Thinking of her EX and how unsatisfying they're past sex life had been, caused desire to intrude into her consciousness and a warmth began to build between her legs. Without realizing it, her hand crept to her rising breast, where she was surprised to find her hardened nipple protruding against the bodice of her peasant blouse. As she brushed her fingers against the cloth, she moaned in pleasure. Her conscience told her she should stop, but her fingers refused to obey. Leaning back in the chair with her legs splayed, she pinched the pouting nipple of her left breast. Almost out of control, the shock of passion that drove through her body caused her high heels to "rattatattat" against the floor tiles. Jean felt the wetness building in the crotch of her panties. The fire in her pussy sent her last inhibition up in smoke. Raising her buttcheeks, she drew her tight skirt to her waist and slipped her hand inside her panties. Using her middle finger she found the source of her passion. With her eyes closed, she fantasized a faceless young lover teasing her hardened clitoris. Each flick of her fingertip equaled the flick of her lover's probing tongue. She installed in her fantasy lover all the special qualities of sensitivity and lovemaking she most wanted from a man. As her emotions rushed towards orgasm, her fantasy lover raised his head. The shock of recognition brought her to a screaming, legtrashing climax. The most powerful climax of her twentytwo years. The face in her fantasy was Tim's! As her passions subsided, her shame and confusion grew. Her mind raced to find an explanation. None being available, she began to cry softly. "How could I play with myself, here of all places and why would that sweet boy's face be the one in my fantasy. Am I so horny I'm going to start seducing tender young boys? Have I no shame?" In an effort to compose herself, Jean straightened her clothing and proceeded to the ladies room. On the way back to her desk, she heard the laughing voices of her two sons emerging from behind the closed doors of the gym. Deciding to see how they were getting along, she reached for the door handle when she was struck with a concern. Checking on the boys might be construed, by as sensitive a youth as Tim, as questioning his ability. Not wishing to hurt his feelings, she turned and took the stairs up to the second floor. A fourfoot wide landing ran along three sides of the gym. Stepping quietly through the swinging doors, Jean found she was positioned directly over where the three boys were playing. They were obviously having a good time wrestling with each other on some foam mats left just for that purpose. In a moment it became obvious that it was her two sons paired against Tim and he was holding back, allowing them to "pin" him to the mat. Just then, they pushed him over on his back, one pinning his arms while the other sat on his legs. Tim's eyes momentarily met hers...she was discovered. In the same instant she realized he was no longer looking at her face, but was instead, staring up her skirt. As quick as she realized what was happening, that's how quick another fire grew in her womb. Grasping the open railing for support, she closed her eyes and again imagined young Tim's head positioned between her splayed thighs, stroking his tongue against her pussy lips, munching gently on her clit. A soft passionfilled groan escaped from between her clenched teeth. Jean, lost in her fantasy, didn't understand her next action. She found herself spreading her thighs even farther apart thereby exposing herself completely to Tim's view. Tim enjoyed playing with the two boys. He knew he could beat them because of his weight and size, but decided to let them win. When they pushed him to the mat he found their mother looking down on them. His eyes were quickly drawn between her legs and up her skirt. His position enabled him to see the exposed welts of her nylons and the whiteness of her naked thighs before they merged into darkness. He fully expected Jean, based upon his understanding of how a woman should protect herself from exposure, to immediately step back or at least tightly close her legs. When instead, her thighs spread even wider apart, he rationalized that Jean didn't know what she was "showing". His eyes ran up past the welt of her nylons and were only stopped by the thin strip of white lacy nylon covering her womanhood. Not able to tear his eyes away, he felt the dick in his shorts thickens and then push its way down his leg. Jean "felt" Tim's eyes on the center of her passion. With her eyes still closed, she immersed herself back into her earlier fantasy, "sensed" his trusting tongue against her trobbing clitoris and without touching herself, orgasmed profusely. Her legs violently shook as her pussy drenched her panties, her womanly juices running down her naked thighs. It was as strong and satisfying an orgasm as the last, all without any physical contact! Tim, unaware that Jean was in the grip of an orgasm and spurred by his fear of discovery, quickly admitted defeat to the two boys. Using the excuse of having to pee, he rushed off to the john, but not before Jean looked down and was pleasantly shocked to see the large hardon he unsuccessfully tried to hide. Not wanting to be discovered by her sons, she returned to the ladies room to repair the damage to her clothes, while Tim used his visit to the lockerroom to bring himself to orgasm, all the time remembering what he had seen. PART 3 Jean returned to her desk and spent the next two hours in the office trying to concentrate on her work. Eventually, she was forced to accept the fact that she wasn't accomplishing anything. Her mind kept wandering back to what had occurred earlier. Locking the office, she entered the gym where she was met by the enthusiastic reports of how much fun her children were having. Both Tim and she acted as if neither had been aware of the other. Since it was almost lunchtime, Jean suggested Tim join them in the cafeteria and he willingly accepted. During lunch, she questioned him in such a manner, that he revealed personal information about himself without being aware of how much he was openly divulging. She grasped his problems with his father, inferred his emotional attachment to his mother and now understood why he was so sensitive towards women. Halfway through lunch, they were joined by her boss, the Commandant of the Military Academy. In the conversation, she explained how they had met and how Tim was graciously watching her two boys while she worked. Jean explained her ongoing problem of finding a qualified sitter and asked her boss if she could avail herself of Tim's services on a semiregular basis. That is, whenever she couldn't find a sitter, could Tim watch the boys at her house? After further discussion, his complete approval was given. He even approved Tim, if necessary, being allowed to sleep over if she had a late date. Lying, she explained that this was the exact case tonight and her boss directed Tim to pack a bag and sign out into Jean's care. After lunch, Jean returned to work, while Tim went back to watching the kids. She "buzzed" through the mound of paper in record time. Making sure she was alone, she called her older sister Susan and asked if she would "take" her nephews to a movie that night. After Susan agreed, Jean hinted that she might have a male visitor at which point her sister offered to keep the boys overnight. Jean then went into a thorough explanation about Tim. She told her sister she had been so happy to get her boss's permission for Tim to babysit that she hadn't realized the complication his being there might cause. If he spoke out of turn, about her male visitor, back at the school, her job might be in jeopardy. She suggested that Susan not bring up her keeping the boys overnight and later, act as if the idea was a last minute decision based upon the lateness of the movie. Susan readily agreed. With her plans set in motion, she locked the office, found the three boys, waited for Tim to pack and then drove to her house. During the drive, she allowed her skirt to rise above the tops of her nylons and felt rewarded by the bulge that grew in Tim's uniform pants. After dinner, Susan showed up, asked to take Jeff and John to a movie saying nothing about their staying over. When Susan, on the side, asked her sister about Tim, Jean said she would return him to the school when she left for her date, explaining to The Commandant she wouldn't be out as late as she had originally anticipated. Susan wished her well, kissed her cheek and left with her nephews. Jean asked Tim if he minded being left alone until the boys came home while she was out. Tim, realized he would be alone in the woman's house for hours and as it had been a long time since he had the chance to play in panties, nylons or a slip, seized upon the opportunity and readily agreed to stay and wait for the boy's return. Jean cautioned him not to say anything to her boss about the change of plans, as he might not understand. Tim noted her concern and promised he wouldn't say a word about the change. Jean suggested he watch TV while she went and prepared for her date, which is precisely what he did. Leaving him alone Jean went to her room and changed into the sexiest outfit she owned. The dress was backless, made of polyester wool crepe, dyed black and did nothing to hide her charms. Under it she wore a black garterbelt, black sheer nylons and French cut, black sheer panties and no bra. Finishing off the effect she wore 3" black patent leather heels. Looking at herself in the mirror, she knew the reaction she would get from the young boy. When Jean entered the den, supposedly to give Tim some final instructions, she was rewarded by the look of desire in the youth's eyes. He could barely mumble his understanding as he riveted his attention to the exposed roundness and the tanned cleavage of her breasts. When she spun around to leave, a low gasp of youthful appreciation escaped from between Tim's lips. Jean's lowcut dress had exposed her nude back and the obvious fact she had no tan lines. It had not escaped Tim's attention that Jean must sunbathe in the nude. "Why thank you for that reaction. Now I hope I get the same from my date. Do you really like the way I'm dressed? It's not too revealing is it? Maybe I should change? You don't think I'm too old to run around dressed like this?" She coyishly asked. Assuring her she looked fantastic, Tim unsuccessfully attempted to hide the growing bulge in his pants. Pointing at his erection, Jean exclaimed. "Oh, I must really look good if I can cause that much of a reaction from a young boy! Tim lowered his head, truly embarrassed and began to apologize. Jean grasped his hand and said, "Tim, let's sit down on the couch for a minute and talk." As they sat down, she stated. "There's no need to be embarrassed, women dress this way on purpose. We do it to get men's attention and excite them. Why should you expect to be immune, afterall you're not that much younger than I am! If I didn't obtain a reaction from you I'd be disappointed. A woman likes to know that men think she's sexy, or we wouldn't go through all the trouble to look this way. The type of clothes we wear causes women to accidentally expose their bodies to men's perusal everyday of our lives. Think about it, every time we sit down on a chair and cross our legs, we expose at least our thighs. Getting up, if we're not especially careful, allows men to see up our skirts all the way to our panties. Women have become accustomed to daily exposures of their bodies so we use it to our best advantage. Most men don't realize we do it on purpose! We dress to tease men! A man's vivid imagination is a woman's greatest weapon in the war between the sexes. It gives us power over men. Almost every man I've ever met will 'break his neck' to see up my skirt. Sometimes I purposely let someone I really like look up my legs...like I let you this morning." Tim exclaimed. "You knew that I was looking up your skirt? Does that mean you really like me?" "Of course I like you, I like you a lot! I think you're very sweet! What happened today, started out as an accident. I was checking on the boys, but didn't want you to think I was checking up on you. When I stepped out on the landing I had no intention of even being seen. When you looked up and discovered me, I felt I might have hurt your feelings. Then, when I realized where your eyes were looking, it pleased me that you weren't upset with me and that you liked what you saw. I want to be honest with you, if you'll be honest with me? How about it?" Tim, afraid his voice would crack, nodded his agreement and Jean continued. "Having you look up my skirt excited me! That's why I spread my thighs so you could see even better. I wanted you to see more of me! I knew the effect I was having on you. It didn't matter how much you saw. We certainly weren't hurting anyone. What started out as just another accidental exposure, turned into two people enjoying the situation. I got just as excited as you did. Tim, as you grow older, you'll find most women enjoy being teases. A woman who's comfortable with her body isn't afraid to expose herself when the situation suits her. Maybe I shouldn't be telling you all our female secrets or maybe it's time you told me a few of yours. I know you got hard and then ran off to the john. Did you play with yourself? Did you come?" "Yes. I couldn't help it. I almost didn't make it! When I got there I couldn't believe how hard my dick was. Oh! I'm sorry, I shouldn't have said that word." "Tim, it's OK. You don't shock me, I'm an adult woman who has two kids. Honey, I definitely know what a dick is. How do you think I had those kids? Did you think of me and my panties when you played with your dick?" "Yes!" Smiling sheepishly as he answered. "Good, I'm glad, that makes me feel even better that my accidental exposure wasn't wasted." Kissing him on the cheek and then rising, she said. "Well, I've got to get going. If you get hungry, help yourself. I'll probably be late, so don't think you have to wait up." Tim, hoping to get another look up her short dress, walked Jean to the car and held her hand as she climbed behind the wheel of her Camaro. He was rewarded, with another "accidental" exposure, as Jean dropped onto the low seat, pausing with one leg in the car and the other still on the ground. Her short skirt sliding back past the tops of her nylons thereby again exposing her panty covered crotch to the youth's eyes. Thanking him for the helping hand, she commented. "That nice new bulge in your pants tells me I must have had another accidental exposure." Giggling, with a twinkle in her eye she smiled up at him and said. "I really must learn to be more careful! If I keep having these 'accidents' you might start thinking I'm doing it on purpose and you know I wouldn't ever do that!" she giggled. Then lifting her other leg in such an exaggerated motion that she totally exposed her panty covered crotch, while at the same time running her tongue across her moist lips, she closed the door, and drove off. Watching her drive away, all he could think was "WOW, what a sexy woman!" PART 4 He returned to the family room, tensely waited about 15 minutes and then headed for Jean's bedroom. He stood in the doorway and peeked inside. The clothes Jean had worn earlier were strewn about the floor and bed. So were several outfits that had apparently failed to make the cut. Stepping into the room, he immediately detected a hint of makeup, perfume and hair spray in the air. The room smelled so sexy, so sweet, and so delightfully feminine he felt his cock rising! Tim moved to the pile of clothes Jean had worn earlier that day and now lay discarded on the floor. Using the tip of his shoe to push aside the skirt, he uncovered her lingerie, including the tiny bikini panties he had seen earlier that day covering her pussy and ass. Bending over, he picked them up, brought them to his nose and inhaled deeply. The musky woman's scent permeated his senses. Placing them on the bed, he went to Jean's open dresser drawer. Inside were three neatly folded piles of panties. The styles ranged from tiny, sexy bikinis, more conservative hiphuggers and finally even more conservative brief style panties, the kind he and his mother usually wore. He carefully pulled a second drawer open and looked down at an array of bras, slips and camisoles. The third drawer displayed hose, both panty style and nylons along with the garterbelts to hold them up. The belts were much more feminine than those of his mother's. These had lacy little straps of elastic with bows on them and came in assorted pastels and rich colored reds and blacks. He pulled the last drawer open and found Jean's nightgowns. Running his hand through the silky material he tried to imagine Jean in the more revealing ones. Meanwhile, Jean had driven around the block, parked her car in a secluded spot and smoked a cigarette. Wanting to rush back home, she forced herself to wait, knowing any young boy as sensitive as Tim would hesitate before he began to snoop. Not really knowing what he would do, but guessing he would at least go through her lingerie drawers, she wanted to catch him "redhanded". Holding the threat of exposure over him would guarantee the youth's total obedience. When she could no longer wait, she crossed through a neighbor's yard and snuck up on her bedroom window. Before leaving for her supposed date, she had left the window slightly open. Using a long handled comb she quietly pushed the shade aside and saw Tim standing before the opened drawers of her dresser. Mentally congratulating herself on the success of her plot, she began to turn away to sneak into the house to confront the youth. At the last moment she changed her mind. Out of the corner of her eye she had observed Tim beginning to undress. Not wanting to miss this, she again positioned herself under the window. Inside, Tim quickly removed all his clothing. Standing before the fullsize mirror he stroked his cock and balls with Jean's discarded slip while inhaling the scent from her panties. His hand pounded his male organ as he furiously jackedoff. He was ready to spurt his hot cum across the bedroom carpet when he realized the mess that would be caused by the blobs of sticky cum. Rushing to the adjacent bathroom, out of Jean's sight...he climaxed into the toilet. Then using some tissues, he cleaned himself, making sure he squeezed every last drop out of his now softening organ. Jean, who felt cheated, rushed to the back door, quietly let herself in, snuck into the bedroom and hid in her walkin closet. All this occurred while Tim was cleaning himself. Her intention was to surprise Tim as he returned from the bathroom. She again changed her mind when he returned carrying additional articles of her clothing, obviously taken from the hamper. She didn't know what purpose they would serve, but hoped another demonstration would be forthcoming. Afterall he was a young boy and was probably ready to come again. What she couldn't understand was why he was carrying her strawberry blond wig in one hand. She decided to take a wait and see attitude. Tim lovingly laid out all the finery across Jean's bed, then picking up an emerald green garterbelt, he put it around his boyish waist, connected the clip, spun it around so the fastener was in back with the garters dangling against his thighs. Then sitting on the bed he carefully rolled a pair of sheer, black nylons up his legs and expertly attached them to the garters. Lifting one leg, he provocatively ran his fingertips over the sleek nylon, removing any looseness or sags. Doing the same to the other leg, she heard him say. "Boy, I sure wish I could wear these every day!" Rising, he carefully straightened the hose and expertly adjusted the straps for a better fit. Stepping into the matching emerald green satinlike panties, he slithered them up his legs, past the garters and shimmied his ass into the delightfully cool material. Pausing to accommodate his semiturgid penis back between his legs, he reached for the bra lying on the bed. By this time, Jean realized Tim was a crossdresser and a very adept one at that. He even exhibited the mannerisms of the feminine gender. Obviously, she mused, he had been coached, probably by his mother or some other woman! Jean, as she watched, used her free hand to stroke her nipples through her dress. This was even better than she could have hoped. Now, with this knowledge, he would have to obey her every whim. As she observed Tim feminize himself she became more and more interested, more and more excited and less and less concerned with the power she originally wanted over him. Now she desired him as a lover and not as a "plaything". Jean had always had a hidden desire to lie with another woman, but had been afraid to take the first step. In fact, it was rumored one of the secretaries at the office was gay and Jean had pictured the woman in her fantasies. However, not being brave enough to approach her, she now found herself with a solution to her craving. Raising her skirt, she slid the crotch of her panties aside, exposing her womanhood and began to gently stroke her tunnel of lust. Inserting two fingers deep inside herself, she used her other hand to masturbate the bloodengorged bud of her clit. Mentally she warned herself against losing control or emitting any sound of passion that might cause her to be discovered. Her mind reeling from the sensuousness of what was being enacted before her eyes she decided she preferred the direction towards which the bedroom scene was moving versus her initial plan of control over the youth. Tim, unaware of Jean's presence, had finished crossdressing. He had chosen an offwhite blouse with ruffles running down the front and a black straight skirt that zippered and buttoned on the side. The skirt was a bit long, as the hemline fell past his knees, but he had chosen it because it highlighted the round globes of his ass and the slit up the side displayed his nylon clad thighs to their fullest. Standing before the mirror he bent forward and placed the blonde wig upon his head. Adjusting it by running his fingers through the strands he stood there satisfied with his appearance. Oh, he knew he needed makeup, jewelry and heels but he wasn't sure if he had the time for makeup and the rest could be obtained easily enough. He relished the titillating feelings racing through his body. This was the first time since leaving home he felt gender correct. He realized, Jean's lingerie was even more satisfying than his mom's was. Also, dressing in the clothes of a woman who was a stranger increased the sensuousness he felt. Turning, he noticed Jean's jewelry box sitting on the dresser. He walked over to it, reveling in the feel and sound as his nylon covered thighs rubbed against each other. Tim opened the box and found a perfectly wonderful pair of gold and red enamel clipon earrings. After attaching them to his earlobes, he decided he really needed heels and proceeded towards the closet. Jean, seeing where he was headed and realizing the probable reason why, pulled her fingers from inside her pussy, dropped her skirt, grasped a pair of heels and pulled the door open just as Tim reached for the handle. "Are these what your looking for, Tammi?" Tim was stunned. The shock caused an immediate reaction in his panties. The blood rushed from his dick to his face, causing his member to shrink and his cheeks to blush. He was caught! Now his mind raced from one consequence to the next. Not only would he be thrown out of school, but also his crossdressing would be exposed to his father. Knowing his father's punishment would certainly be painful, he also realized his mother's involvement might be exposed. He couldn't let that happen, he loved her too much! Maybe he could convince Jean not to say anything. Before he could beg, she spoke. "Tammi, why don't we sit on the bed and have another little talk. Just us two 'girls'. How about it, sweetie, would you like that?" Confused by Jean's attitude, but afraid to refuse the woman, Tim nodded his head as he fought to hold back the tears. Jean took his hand and led him to the bed where she directed him to sit on the edge. Sitting next to him at an angle, she slid her right ankle under her left knee. He immediately noticed the space this opened between her thighs, again exposing the welt of her nylons. Even though he was scared, he still couldn't help himself and openly stared at the woman's firm fleshy thighs. "Do you like what you see? Good, you're supposed to! I told you women use the way they sit to tease men, its a way of getting power over them. Can you feel the power I have over you? If I opened my legs just a bit wider, wouldn't you do almost anything I asked? Of course, you're going to agree to anything I want anyway, aren't you? Otherwise I'll be forced to call the school and tell them about all this. I can just imagine what the Commandant and the other boys would say about you wearing panties and my bra. I can also guess what your father would say about nylons and a garterbelt. Is that what you want me to do?" The look on his face told her the answers to her questions without any verbal response. He definitely desired her silence and would do anything to earn her cooperation. "Tammi, that's going to be your new name whenever you're dressed this way, but before we go any further, you'll have to tell me everything you know about girls and/or women. I also want to know everything about your crossdressing. I want to know how you got started, how often you dressup and who taught you feminine mannerisms? I know you couldn't become so adept at wearing women's clothes without some expert help. I must have your total obedience and you must be totally truthful. If I catch you lying or hiding the smallest bit of information from me...we'll stop and I'll take you back to the school dressed in my clothes and tell the Commandant what occurred here tonight. I'm sure you don't want that, do you?" "No, please don't do that!" He begged. "Good! Now that you thoroughly understand the control I have over you we can continue our "girltalk". If you accept my terms and I don't see that you have any choice, I'll let you continue to come to my house, dress in my clothes and I'll even teach you more about being a girl. There will be other exciting things we can do together dressed as girls, things I'm sure you'll enjoy. All I've said can be yours if you agree to my terms. Well?" "Yes, I'll obey your every request and tell you everything." Now guaranteed of his complete obedience she told him to begin. As the story of his crossdressing, his desire to have been born a female and his emotional attraction to his mother unfolded, Jean found herself becoming aroused. The sexual heat she had experience earlier began to build again. Asking questions, she determined he was a virgin, but definitely knowledgeable about the ways of sex. It was obvious his mother had explained quite a lot. He admitted he had never seen a woman naked, not even his mother. Girlie magazines, his mother purchased for him were his only knowledge of nudes. When he was all finished, he asked. "What are you going to do to me? Should I start taking off these clothes? What about your date and when will the boys be back?" "Oh, those are my other surprises. I don't have a date and the boys are going to sleep over at my sister's. When I saw you staring up my skirt today, I knew there was something special about you and made up the whole story about a date. I also called my sister and made all the arrangements for us to be alone the entire night. As for the clothes, wouldn't you rather leave them on for now?" "Yes, the only time I'm really happy is when I'm a female!" "Maybe I shouldn't be telling you this. I like the way you look in my clothes. Of course you need makeup but even so you make a very sweet young lady." "Jean, if you keep my secret, I promise I'll do anything you ask!" Taking him in her arms, she kissed him. Then forcing his lips apart with her tongue, she taught him the nuances of "French" kissing. When they separated, he asked her in his best Tammi voice. "Are you going to introduce me to lesbian love?" "Yes," she answered. "Before the night is over I plan to teach you all there is to know about two women making love. I don't want you to hold back or be afraid to touch me, but you will listen to my guidance." Reaching out to each other, they began to kiss in earnest. As their emotions rose, Jean moved her fingers to Tammi's ruffled blouse. Unbuttoning it, she reached inside the cups of his bra, smiling to herself as she discovered the bunched nylons he had used to simulate female breasts. Slipping the straps off Tammi's shoulders she reached behind his back to release the catches. Cupping her right hand, she stroked his hairless chest as if he had real tits. Both were amazed at the puffiness that rose from his chest muscles to fill her cupped hand. The nipples elongated, actually reaching the size she remembered when her own breasts began to bloom. In addition, they exhibited the sensitivity of female nipples. Jean thought to herself. "Maybe he should have been born a female, he certainly reacts like I did when I was his age!" Using her tongue, she licked, nipped and sucked each ridged nubbin of flesh. Tammi's reaction was a series of soft mewing moans as he twisted his chest to obtain the greatest pleasure from Jean's playful teasing. Realizing he was getting too excited, too soon, she broke away and said. "Use what you've just learned to please me. Always remember, a woman's body is to be adored, there is no place for roughness, at least until she's ready to orgasm." Tim began his seduction by licking and kissing her neck and ears. Gently, he stroked her bare shoulders and back. Tim slid his hand to her breast and as gentle as a soft whisper stroked the rising nipple through the dress material. Gaining confidence, he gently laid her down across the bed, untied the neck of the dress behind her head and slowly dragged the material down to her waist, leaving her upper torso bare. Jean looked into her young lover's eyes, saw the amazement reflected within them and smiled up to him. A warm tender glow began to build within her soul. This was no longer just sex, she realized, this was a budding love affair. Cupping one of her tender breasts, she raised it to his lips, moaning as his warm breath fell across the pouting nipple. Tim took her offering and lovingly licked and suckled as he had been shown. Using his hands, he stroked and fondled her neck, shoulders, back, stomach and especially Jean's other breast. He learned what pleased her and that's where he concentrated his efforts. Every boy dreams of learning the act of love from an experienced older woman and he was one of the lucky few whose dream was coming true. When Jean pulled the nipple away, he knew to concentrate on the other breast. Jean lay back and basked in the pleasure her youthful lover was providing her. For a first timer, he was more than adequate, he was actually adept. As his confidence rose, her need to be in control lessened. This scared her. "That's enough of that for now! Stand up and undress me!" she roughly ordered. Tim obeyed immediately. He rose and then in a surprise and gallant move, offered his hand to assist Jean in rising. This attention was not lost on her. Where a moment before she had been concerned, no actually scared about controlling his level of obedience, this sensitive gesture quickly erased all fear. Now she could let herself go and if the need to take charge ever arose, she knew it was only for the taking. Tim was too tractable to ever cross her. Meanwhile, Tim had continued to tease her tits with both his fingers and his wet tongue. Turning her back and leaning against him, she said. "You did that very well! Now show me how you think two women would make love. Don't worry, I'll help you when you need it." Tim's fantasies about lesbian loveplay had prepared him well. Reaching up, he lifted the hair from her neck and "nuzzled" and kissed the short hair he found there. This caused Jean instant pleasure and subsequent "goosebumps". As she shuddered in delight, she felt his kisses move across her bare shoulders, down her spine and only stop when he reached the last exposed inch of skin at her waist. Grasping the zipper, Tim slowly pulled, enjoying the view as the dress parted before his lusting eyes. Jean's panty covered cheeks displayed their fullness. Then when she "shimmied" her hips, the dress gently floated to her ankles. The sound of his surprised gasp of appreciation brought a glow of pride to the woman's features. There the sexy young woman stood, naked to the waist, her garterbelt and nylons framing her pantycovered ass and her smooth, sleek thighs. Bending forward at the waist to teasingly straighten her hose, she was again surprised when Tim knelt down behind her, hugged her around the middle and ran his face across her asscheeks. Remaining in the position she spread her thighs even wider, thereby encouraging him to continue his sensual adoration. Tim used his stiff tongue to run the crevice between her cheeks. When he discovered the exact location of her pucker hole, he jabbed his tongue hard up against it. The moan of pleasure from Jean encouraged him to continue. Sliding and twisting backwards through her legs, Tim licked and kissed her pantycovered crotch. Looking upward between her soft thighs, he noticed how her swollen pussy lips had spread open inside her sheer panties, their outline in the now damp almost seethrough material plainly evident. Jean, realizing what his next move would be and not yet emotionally ready to have her pussy licked...stepped away from the youth. Turning and sitting down at the bed's edge, she said. "Tammi, why don't you slip out of that skirt and show me what else two girls in love can do with each other!" Quickly stepping out of the skirt, he caught Jean looking at the bulge in his panties. Not wishing to destroy the image of two lesbians making love, he adjusted his dick back between his legs, then knelt down before his lover's knees. Gently grasping her left ankle he planted a firm kiss on the exposed upper arch. As he kissed and licked his way up her nylon clad legs his eyes never wandered from the slit of black, sheer, silk covering her musky scented womanhood. Upon reaching her naked thighs he continued his kisses, sliding his hands up under her tush. Squeezing the firm muscles, he inched his lips ever forward. Jean's mounting passion finally manifest itself by her grasping his ears and pulling his face against her panty covered pussy. She knew her need was now too demanding to curtail. Twisting his head, back and forth against her panty covered clitoris caused enough pressure to set her off...and she doused her panties with her juices. Jean's strong orgasm excited the youth and he dove forward, causing a second series of sensual shockwaves to course through the young woman's throbbing lips of lust. As her vibrations slowed, Tim licked and sucked the sweet emissions through the material as moans of sexual satisfaction slipped from between the woman's lips. Jean lay back basking in the warm afterglow of her two orgasms. Tim knew that Jean had come and suspected it had been a multiple climax. Realizing she needed to rest, he slid next to her on the bed. Ever so gently, he ran his fingertips up and over every sensuous curve of her delightfully luscious body, being extra careful not to arouse the woman's passions any further. Snuggling up to her ear and in his best Tammi voice, he made verbal love to her. Recalling to his lover how excited Tammi had gotten from their mutual girlplay. Telling her about the flood of erotic sensations that had assailed Tammi's breasts and sopping wet "cunni". This whispered fantasy recreation brought joy to Jean's face and an understanding of their new relationship. Jean's initial desires had been brought about by pure lust, now that lust was replaced by feelings of tenderness for the young boy/girl resting his body beside her. Obviously some of her initial plans needed reconsideration. Maybe she should "talk" to his mother. "Tammi, remember your promise to tell me everything?" "Yes," he answered. "How would your mother feel about you spending some of your weekends at my house?" she asked. Tim, not knowing where she was headed with the question, asked. "What do you mean?" Jean spent the next hour discussing her ideas with him. When she finished it was agreed that she would write a letter, on school letterhead, inviting "mom" to attend a Mother's Tea and weekend visit. The invitation would explain that those invited women who lived far away were being offered lodging at the homes of female employees of the school. Jean had selected Tim's mother since her son was familiar to her. In the letter, Jean would explain how she had met Tim and how he was "sitting" for her kids. Tim encouraged her to hint there was more to their relationship. He suggested Jean comment on how much help Tim was in selecting outfits for her to wear and how they had gone clothes shopping together. He felt these hints would insure his mother's attendance. Tim was also to telephone his mother and if necessary also drop small hints. Tim felt sure she would accept, if only to get a weekend away from her abusive husband. After his "mom" arrived, they would explain the real reason...his need to crossdress. Depending how well "mom" reacted, they would explain everything. If his mother received this in a positive manner, the three "women" could come up with a plausible scheme that would satisfy both the administration and "mom's" husband. Their plans complete, they resumed their loveplay. Jean now decided that it was time he lost his female virginity. Removing her panties and gently cleaning her pussy lips with a warm washcloth, she proceeded to explain the inner workings of the female sex organs. Spreading the puffy outer lips of her pussy she tutored him as to how women satisfy each other with their flicking tongues and fingers. Stroking the bright red bud of her still swollen clitoris she explained it was as sensitive as the crown of his penis and must be approached with gentleness. "I'll show you what I mean!" she said. Reaching between Tammi's legs, she gently massaged Tim's cock and balls still encased in their satin pouch. Within seconds he was ready. Slipping the panties over his hardon, Jean stretched the elastic behind and under Tim's balls. This caused his male organ to stand straight out from Tammi's sparsely haired pubic bone. Cupping the sack, she teased the sensitive area behind it with her nails. Licking her lips, Jean lowered them to the purple tip of Tammi's pulsing penis. Parting her moist lips she engulfed his entire crown. With a slow, twisting motion and a swirling tongue, she sucked her way back to the tip. Tim couldn't believe the sensations Jean's mouth was causing. He had never gotten this excited, this quickly. He knew he couldn't take much more of her licking and sucking. When he felt his balls "tighten up" and the jism rise he tried to pull away, afraid he would upset Jean by shooting off in her mouth. Jean's lips however wouldn't let go. Her jaw muscles held him tightly as she pulled the cheeks of his ass forward with her hands. As she increased her strokes, she felt his organ momentarily swell and then spasm in her mouth. Using her cheek muscles to suck out every drop, she swallowed every last spurt. Using her tongue, she then licked the excess that had run down his shaft, hoarding it in her mouth she "Frenchkissed" him. Tim tasted his own salty warm fluid and was shocked to find out he enjoyed the experience. Rising, Jean left the bed area and went to the linen closet in the master bath. Fishing behind some sheets, on the top shelf, she found the large strapon dildo she had hidden there. She had purchased it, just recently, in the hope that the dildoe's size would resolve her masturbation problem. While she hadn't really needed the strapon device, that's the way it came. Slipping it on, she inserted the rubber cock through the opening from behind and positioned it so it "rode" against her clit. Grabbing a jar of Vaseline jelly from her vanity, she returned to the bedroom. Tim had assumed Jean had left to use the john. He had spent the time she was absent, basking in his own afterglow. When he saw Jean emerge from the bathroom, with the huge swinging dildo at her crotch, he was scared and confused. He hopefully asked. "Are you going to teach me how to suck a cock? It's not necessary, I'm only turned on by women!" "No!" she leered down at the youth. "Tammi, I'm going to make you a real woman, I'm going to take your virginity. You can't be a real girl until you've felt a cock inside your 'pussy'!" Immediately guessing what Jean had in mind and in fear of the dildoes size, he began to object. Then remembering his promise to completely obey the woman, he resigned himself to being "fucked". Jean had him assume the subservient position of leaning on his elbows and knees. His firm cheeks naturally spread for easy penetration. Then lathering both the dildo and two fingers of her hand she worked the lubricant around the squinting eye of his tush. Using first one finger and then a second, she coated the inner walls of his anal tract. Tim for his part, found he was enjoying Jean's fingers slithering up his ass. Surprised by the sensations that coursed through his genitals, he was getting semihard. Jean told him to relax his sphincter muscle and he found the finger fucking even more pleasant. When Jean felt he was fully primed she positioned the dildoes bulbous head at the pouting entrance and surprising him, pushed the crown portion into his surrogate pussy. Tim let out a loud piercing scream of abject pain and tried to pull away. Jean, anticipating his reaction, fell forward, using her weight and position to overpower his attempts to escape. Firmly holding him down, she seductively whispered in his ear. "Tammi, all women suffer pain the first time their cunnies are violated. It's part of being a woman. Just relax and the pain will go away. Be thankful I care for you, most girls are less lubricated their first time and suffer more than you." As the pain was already beginning to subside, Tammi relaxed even more and was reassured when the pain was replaced by a pleasant full feeling. Jean, aware of his condition, slowly began to inch more and more of the rubber phallus inside him. When she had all eight inches up his "pussy" she began fucking him in earnest. "Reach under yourself and stroke your "clitty", sweetie. When you get ready to come, stop and let me know." Tammi felt the passions building in his groin. Closing his eyes, she imagined she was on a date in the back seat of a car. She had allowed the boy to get her overly excited, had lost total control of the situation and was now being penetrated for the first time. The fact he still wore the garterbelt and hose helped his imagination "picture" the scene. Reacting to the fantasy, she began to push her "pussy" back to meet her male lover. Tim had always wondered what it felt like to be penetrated like a woman. Now he knew...it was wonderful! Aware he was quickly approaching orgasm, he opened his eyes and informed Jean. "I'm about ready to come!" Jean gave one more inward stroke, then pulled the dildo out with a loud sucking sound. Flipping Tammi on her back, she raised his nylonclad legs high into the air and reinserted the dildo in Tammi's "cunt". Spitting into her hand, she reached forward and grasped Tammi's swinging cock, encircling the crown between her middle finger and thumb. Then matching the thrusts of her hips to the twisting motion of her hand, she pounded Tammi's pussy with her false cock while she jerked him off. The sensations "rolled" between Tammi's cock and "pussy". She felt the inner muscles of her "cunt" grasping at the dildo with each outward stroke, trying to keep it from leaving and then spreading wide to meet the "boy's" hardness as it again forced entrance into the channel of her womanhood. No longer wishing to hold back...Tammi came. Her cum exploding in graceful arcs landing on both their bodies. Some even splattered their faces. Jean also achieved orgasm brought about by the direct pressure of trusting the dildo into her "lesbian" lover's "pussy". Exhausted, she pulled out and fell across her newfound lover. Reaching their moist lips to each other, they gently kissed and licked the spent juices from each other's features, giggling as young girls are prone to do when they have a secret. "Now you know how it feels to be a woman! Did you like it?" "Oh, it was wonderful, everything I fantasized it would be! But it was only 'good' because it was you taking my 'cherry'! Jean, I love you! I wish I could be your lesbian lover and live with you all the time!" Jean thought a moment, then said. "After we see how it goes when your mother visits, maybe we can work something like that out between us. I'd love to have a girlfriend like you. Let me think about it. Now I think it's time we removed these clothes, cleaned ourselves up, got into some sexy nighties and went to sleep. We need some rest before my sons come home tomorrow." They did exactly that, giggling and playing with each other as they cleaned up. Cuddling up next to each other, like two spoons in a drawer, they fell asleep. PART 5 Somewhere in the middle of the night, Tim awoke to the warm realization he was being fondled. Pretending he was still asleep, he peeped between his lashes and found Jean was slowly moving her hand across his panty covered ass. Deciding to "see" what Jean was up to, he continued to feign sleep. Jean had awakened, from a sensual dream and looked over at her young lover's body. Remembering what had transpired earlier, she felt desire again building within her. Realizing she still hadn't "taken" his male virginity, nor had she been "fucked", she slid her hand to his satin covered ass. Not knowing if he could perform yet, she rationalized he could at least satisfy her again with his tongue. Moving her hand under Tammi's baby dolls, teasingly up his stomach, she encountered his nipple. Stroking the tip, she was again amazed how hard it became. Lightly pinching it brought mewing sounds from the youth's lips. Assuming he was still asleep, Jean pulled her hand from under the nighty and gently slipped it under the elastic of his panties. Finding his penis fully erect, Jean surmised Tim was faking. Delighted to find him restored, she however, was not going to let Tim get away with his deceit. Cupping her hand around his sack, she began to gently but firmly squeeze his balls. She laughed as she spoke. "When you decide to stop faking, beg me to release your jewels and offer me something 'nice', I'll stop, but not before I get your promise." Not in any real pain, yet, he answered. "If you let go of my nuts I'll promise to eat your pussy." "Without my panties on?" She asked, exerting more pressure. "Yes! Yes! Only stop your squeezing!" Releasing him, Jean ordered him to remove his nighty and panties. As he complied, she removed hers and stretched out across the bed with her arms above her head. Bending her knees and letting them fall naturally open, she exposed her total womanhood. Tim lay down and positioned his head above her pussy. Placing his hands under her tush he raised her pelvic area to his moist lips. Gently kissing and licking her outer lips he used his tongue to open the inner ones. Now darting his tongue into her cunt, he "flicked" the inner walls. "Oh! Oh! Yes! Fuck my pussy. Stick that hard tongue all the way inside. Oh, that feels good! Don't stop!" Tim "bounced" his head between her open lips, mashing his nose against her clit. When he felt her thighs quivering against his ears...he did stop. Letting J

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Hi ISS readers, i am Raj, 24 yrs well built guy working for Indian army. My family lives in ooty. My father being a retired military officer wanted to settle in ooty to relax, lives there with my sweet little sister, Priya 18 yrs. I have lost my mother 8 years back. I was getting trained in dehradun for army, and i got a leave for one month after four long years so i thought of going to ooty to meet my family. I felt happier for getting leave than for the reason i am meeting my family because...

Incest
2 years ago
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Military Affair

MILITARY AFFAIR I am Renuka. I have recently happened to visit this site, which prompted me to share my experience with you. I am married to an engineer in junior commissioned officer rank in Army. I was 22 and just completed my MCA, when I got married to the handsome young man Karthik. It was an arranged marriage. Just two weeks after our marriage we came to Delhi as his leave was over by then. The past two weeks was wasted due to different reasons. Our first night was somehow foiled and the...

1 year ago
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Schoolgirl and schoolboy

This story is a two part. We did it my way, then her way. Enjoy The first part is about how a schoolgirl fantasy, that I wanted to do with my girlfriend. The second part is how my girlfriend did the same kind of fantasy, but she had a twist of her own to do it. It all started, when we looking up costume on what to be for her Halloween company party. She wanted to be something sexy because everyone in her office think it's kind of boring, and she wants to change that. We were looking online and...

Straight
3 years ago
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Romys Sexual Journey from Schoolgirl to Schoolgirl Part 2

The final day of term was mighty hectic. A lot of tears and taking of phone numbers, addresses, future education plans, ‘I’m sure going to miss you ladies. It’s been a real gas. We’ve had some fabulous times together and I just hope we’ll bump into each other sometime in the future,’ I said. And then it hit me! That’s what it was - Paul. I had really been missing him since our liaison and, stupidly I didn’t even know what his surname was! Later that day I would be even further away from him...

3 years ago
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Military Training with the Big Bar Maid

When I entered basic training in the Army in Southern Germany as a 20 year old high school graduate, I was no virgin. In my younger years I had been in an intimate relationship with a much older woman who used to live in our house. She was horny and aggressive, and I was mostly on the receiving end. The school girls were much different, giggling and shy. We did a lot of kissing and petting on dark park benches, but I never had the guts to go beyond that. In the Army, some of my comrades were...

Seduction
2 years ago
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Military Training with the Big Bar Maid

When I entered basic training in the Army in Southern Germany as a 20 year old high school graduate, I was no virgin. In my younger years I had been in an intimate relationship with a much older woman who used to live in our house. She was horny and aggressive, and I was mostly on the receiving end. The school girls were much different, giggling and shy. We did a lot of kissing and petting on dark park benches, but I never had the guts to go beyond that. In the Army, some of my comrades were...

3 years ago
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Military Reunion

I dragged my ass to a reunion finally and saw old mates from past military days. As we held it this time on the beach, there was plenty of hot young ass running around but not for me. I ended up finally working the bar giving a pal a break when a 30 something came up in a bikini and shawl skirt and I asked her for her reunion badge or ID. She laughed and said theres no room on her and I said I can think of a place. I asked her who she was property of and she said a guy from another unit I didnt...

3 years ago
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MILITARY BRATS

Eric Abbott was only 19 years of age and already he had seen just about every country anyone had ever dreamed of seeing. He had lived in Italy, Germany, France, Brazil, Hawaii, Russia, Australia, Canada, Japan and Israel. He had lived in so many places he almost forgot he was born in Florida. Eric had been to all these places because of the life his family led. His father was a General in the US Army and took his family wherever he was posted. Whenever General Paul Abbott was given a new...

2 years ago
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Military Engagement

Chapter 1:An Office Meeting Chapter 1?? :? An Office Meeting Hi! We?ve not really spoken before but you?ve probably heard a bit about me from Larry. I?m Sarah. Ooops, sorry, #06.085. I keep forgetting I?m only supposed to use my slave number. I?ve been doing secretarial work here in Clegg?s organisation for a while now and though lots of bosses like to think they have their secretaries as a sort of personal office slave, it?s only here that it?s literally true. I?ve been helping...

2 years ago
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Military DelightsChapter 3 Trouble

Soon after the Prince became Khan of Tirfil, the raids into Kobekistani territory increased dramatically. Whole villages were razed, their men killed and their women and children taken to Tirfil as slaves. Diplomatic notes were exchanged to no effect. Finally the Emir wrote personally to Khan Habib demanding that the incursions stop forthwith and threatening punitive action if they did not. Ghada Baroud, the Emir's diplomatic advisor was loth to show the Emir the reply, but his Master...

4 years ago
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Military DelightsChapter 4 The Emir Leads

"Master, I have never said this before, and I never thought I would, but ... No, Master! You must not do that." Kamal Qumsiyeh, the Head of Protocol nodded his reluctant agreement with Ghada Baroud, the Advisor on Foreign Affairs. Both men feared for their jobs, and possibly for their lives. Open defiance of an absolute ruler such as the Emir is not generally a career enhancing move; on the contrary, it can often be life threatening. They looked over to General Mustapha, the Military...

2 years ago
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Military DelightsChapter 21 Spoils of War

Jalile Shalabi, the slave dealer, had set up a special reception session in the town square for the members of the victorious Kobekistani army to offer their captives for sale. There were quite a number of women on offer but, to his disappointment, not many of them were either young or beautiful, and none were both. There would be a glut of second rate slaves, he judged, so the prices he offered would have to be very low. Among the less interesting offerings was Nahla, who was being sold by...

4 years ago
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Husband Wife and Schoolboys

THE HUSBAND, THE WIFE AND THE SCHOOLBOYSPart OneLet me explain. My name is Justin. I am a healthylooking 40-year-old married guy and in quite good shape. Not film star shape but I can still pull acompliment or two. I was lucky to marry an extremelypretty, little women called Carrie. She is still 30and we have been married for 10 years so you haveprobably guessed that she was 20 when we married. Iwas lucky, O.K? She has certainly stayed in shape andher slim body pert little upturned breasts and...

3 years ago
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Romys Sexual Journey from Schoolgirl to Schoolgirl Part 1

My interest in sex really started when I was about teens. One Saturday morning in the 1950s I was at home whilst my parents had gone out to visit my gran. The only other person in the house was my brother, Joe, who was just over a year older than me. I was doing my homework downstairs when I hit a snag. I needed a ruler and I’d left mine at school. I knew my brother probably had one and popped up to his bedroom to borrow one. He mustn’t have heard me coming up the stairs and opening his...

2 years ago
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Melody Smiths Schooldays

Melody Smith's Schooldaysby Eve AdorerChapter 15 – My Vacation Vocation Supremely aroused as I had become holding the divine Deneel in a tender embraceas the ultimate phase of Maiden Mead making had been given over to me,a long tepid shower was needed to lower the summit of my ardour and saveme from the evil compulsion to touch myself. My body came down from its peak of heat but very slowly. My mind continuedlost in the maze of lust for the remainder of the sleepless night through whichI...

3 years ago
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Amanda Joins The School Newspaper Chapter 2 of Schoolgirl Amanda Learns Discipline

“Finally I found you Amanda. I thought we were going to meet at the end of the school day and instead you just ditch me. Do you mind telling me why” Jenny said, the hurt clearly sounding in her voice. Amanda stopped and turned as her friend caught up to her on the street. They were a few blocks from school although not on the route they normally took home. Amanda looked at the sky but if she was hoping for divine intervention to whisk her away or at least inspire her tongue on what to...

3 years ago
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Miss Sue Sheri and Me Home schooling Part 1

This is a true story related to me by a long time childhood friend from a time when we were in high school. He told me this story one night after a few drinks and he knew I was writing a book about sexual experiences. I will not identify anyone by their last names. It involved 3 people. As I write this I will emphasize conversations between the parties as to allow the reader to better understand this story. MISS SUE; About early 60s, tall and average build, always short...

3 years ago
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When Good Schoolgirls Behave Badly They Are PaddledOn Guard

When Good Schoolgirls Behave Badly, They Are Paddled. Part 1, ?On Guard?Disclaimer:  Warner Brothers and their studio partners own the show and characters depicted in the show.   All similarities to persons living or dead are pure coincidence. .This story is a parody and the story begins with girls behaving badly.  Rory is accosted and pulled into an in prop meeting, coup held in preparation to remove Paris as editor of the school paper.  Her demands and constant re-writes have caused a mutiny...

3 years ago
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Catholic Schoolteacher

Catholic Schoolteacher I had been a schoolteacher for quite awhile and had even retired after thirty years of service but when Father Tom asked me to join the staff at the Catholic High School I did. He asked me to do so as a personal favor to him. He was not in the habit of asking me personal favors so I knew that he needed my help desperately. I soon realized why he was so desperate in the first place. The money was ridiculous, the classrooms were only half full, and they were...

2 years ago
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Nurturing Nubile NovicesChapter 11 Sues Sexy Schoolteacher

Posted: April 21, 2002 - 12:00:00 am All good things must come to an end and the college student's summer sojourn with his aunt and her nubile daughters was no exception. His amoral activities during his four-month visit did, however, have a lasting effect that went beyond the debauchment of his adolescent cousins and the first manifestation effect of this involved eleven-year-old Sue. Dear Dairy - I sure miss Bill. And Jan, too. Cept she's sposed to be home weekends. I think Mom guessed...

4 years ago
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Meeting My Schooling Friend

Hello every one i am Jona from Hyderabad. All the ladies and girls can catch me at Its a story between me and my school mate whom we met through school whatsapp group. The name of the heroine for this story is Priya. When we are in school, she was the dull student so no boy showed interest in her. But she is cute. All my class girls used to say that she had crush on me. I never care it as in childhood studies are more important. I saw her photo in Whatsapp Group members and she was stunning...

2 years ago
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Sissy Sisters Schooling

SISSY SISTERS SCHOOLING by Throne "You know, sissy husbands aren't born... they're made. You have to teach them to be what you want." Tanya looked at her friend for a reaction. "I suppose you're right," Chelsea said with a thoughtful nod. "Though it helps if they're weak-willed to begin with." "For sure. I mean, our wimpy husbands are perfect examples. They were just waiting to be turned into pansy boys. But it wouldn't have happened without us. They needed to be...

2 years ago
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School of blowjob schoolgirlssexporn stories

When Laura Becker landed a teaching job at Fitzmoore College she was delighted, although she was to be the only female member of the faculty. It was an all male institution, very much into sports and both students and faculty members were built for action. She figured if she couldn’t land a boyfriend in this muscle-bound oasis – then there was no hope. He first few dates were with an assistant football coach, and they always ended up in a sports bar. The last time he took her out was on her...

3 years ago
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Deeply Relished The Paradisaical Sex Trap Set Up By My Two Gorgeous Schoolmates

Hi friends. I am Arun and I’m 23 years old. I’m here to share with you my back to back absorbing sex encounters with 2 of my schoolmate beauties Poornima and Prathiba whom I met after 6 long years. I had no contact with them from the time we completed +2. Prathiba is a Malayalam babe, fair complexion, slim with some fat and flesh in her arms and thighs. She is a real beauty. Poornima is a brahmin, wheatish complexion, slim and a bit skinny. She looks too hot. In fact I used to see both of them...

4 years ago
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The Home Schooling Years

GREASING THE PISTONS AND LUBING THE RODS...Ross Barker heard unusual noises coming from the engine room. It sounded like the deckhand Marcus was being attacked by a wild bear. Making Ross' hero scream and squeal. The savage bear was growling and grunting like a heavy diesel engine. Pounding its way upstream on a fast-flowing river.The then 16-year-old Ross had just finished 5 years of basic nautical schooling. Learning a trade like his father. But after 5 years of education ashore, he...

3 years ago
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My Highschool Counselor

My highschool was same like all the highschool around the country. Freshmen sluts, popular groups, sports, and everything that you'd think to be in a highschool. I was a normal kid through out my highschool years. I had some relationship with girls, had good friends, and overall good memories. One of the best decision was that I was in my student government. I made many friends in there and planned exciting things for my students. But that wasn't the reason why it was the best decision in...

4 years ago
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Highschool Reunion

I’m a family man aged 24 My son is two years old and my wife is 22. We are of hispanic descent. My wife is 5’1′ almost a foot shorter than me. My dick is a thick 10′ long hose. After the kid, sex has slowed down as she’s too worried about Javier Jr to have sex. She has also gained a lot of weight since she had the kid. She wasn’t too thin to start out with either but in highschool my wife was a thin Latina with a rocking ass. I still workout to stay in shape but my schedule is less flexible...

4 years ago
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The Highschool Life of Ry Ch1

Introduction: Alright you guys, here is the complete version of this chapter as well as a promise from myself, that there will be many many chapters to come. to give you an idea, these first chapters will be apart of book one: Sophomore Year. I am planning to have 3 total books for highschool (sophomore, junior, senior) then the College life saga will begin. This will only continue through the positive feedback in the comments, I do not care about votes. I will say there is not sex here in the...

2 years ago
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Home Schooled Siblings

Home Schooled SiblingsBy: Londebaaz Chohan Sylvia was almost 6 years younger to me but growing up to be a very tight woman with just the right amount of meat at all the desired places of her body. Since the split of our parents; we both were living with the parents of our dad because our mother was a drunk bitch woman who fought tooth and nails to get the custody as against our dad but soon after she ran away with some of her lover who also did arrange for her smokes and drinks in addition to...

2 years ago
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Home Schooled

It was when I was in junior high that I realized that being home schooled, I definitely grew up different than other girls who went to public schools. I wanted to experience my 11th and 12th grade years with kids my age to you know go to Proms, and School football games. I know my grades were good enough to even apply to a good collage with out even going to a formal Graduation. The thing is, I would be going with out you know interacting with kids my age. I had a great friend who did go to...

2 years ago
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Military women dominate the best part 1

‘Why the hell are people knocking on my door this late at night?’ You asked yourself. You finally got up and went to the door and opened it. Surprise was one of many things that crossed your mind. “I’m about to ask you a favor that I could never imagine asking anyone, because you’re the only one I can trust to help me.” I whispered very seriously to you. “Umm I’m really confused right now. It’s almost past midnight, we have work tomorrow and we shouldn’t be in the same room vicinity this...

1 year ago
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Military Wife Blow Job Lessons

Introduction: My ex and I began to have some friends among the other jr officers After a while my ex and I started to have some friends among other Jr. officers and their wives. I found that they were in general, prudes, and that the husbands complained all the time about them not doing oral on them and a couple that did not care for any contact with their mouths to a cock My ex and I laughed about it a lot and then one day he came home and said, Hey, the guys wana know if you can teach the...

3 years ago
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Military Man Part 2

I was warm, content and relaxed. The dream I was having felt heavy and musky like a strong yet sweet perfume, consuming me completely. I felt weightless, floating softly in this cosy state. Slowly the dream began to shift and I started to grow colder, and I groaned a little as I felt myself waking up from this pure relaxation. I opened my eyes slightly, letting them adjust to the darkness around me. It can’t be morning yet, I couldn’t see any form of light except from the dim lamp outside. A...

3 years ago
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Military Man

I walked out of the train station, the bag at my shoulder beginning to weigh me down. I was over 2 hours away from home and had been travelling far too long for my liking. I shifted my heavy overnight bag higher up on my shoulder and steadily made my way down the concrete steps, careful not to topple over due to my sore feet. As I cautiously stepped onto the pavement, my phone began to ring in my pocket. Grumbling, I once again shifted the weight of my bag in order to dig around in the pocket...

2 years ago
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Military slut

Quick story ive just thought of.Kirsty is a slut in a uniform. She joined the army just so she would be surrounded by men. When choosing her role in the army she looked for a role where she would have access to more men with hardly any other women. She discovered that being a clerk (hr) would mean she could go to any unit in the country. Through basic training the men were hard to get to as she was with 23 other females. But her lust for cock had her sneaking out of her dorm room to go and bend...

4 years ago
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Military Strength

My wife Lauren is thirty-five and I'm thirty-four. She was a virgin when we married. She is four feet eleven inches tall and weighs ninety pounds, with a body you would kill for. Lauren and I have fantasized about her fucking someone else while I watched, but nothing like that has ever happened in the sixteen years we have been married. Recently we took a vacation together and enjoyed one wild time I'll not soon forget. A number of servicemen just happened to be staying at our hotel. They were...

2 years ago
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Military Man Part 2

I was warm, content and relaxed. The dream I was having felt heavy and musky like a strong yet sweet perfume, consuming me completely. I felt weightless, floating softly in this cosy state. Slowly the dream began to shift and I started to grow colder, and I groaned a little as I felt myself waking up from this pure relaxation. I opened my eyes slightly, letting them adjust to the darkness around me. It can't be morning yet, I couldn't see any form of light except from the dim lamp outside. A...

Straight Sex
3 years ago
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Military Man

I walked out of the train station, the bag at my shoulder beginning to weigh me down. I was over 2 hours away from home and had been travelling far too long for my liking. I shifted my heavy overnight bag higher up on my shoulder and steadily made my way down the concrete steps, careful not to topple over due to my sore feet. As I cautiously stepped onto the pavement, my phone began to ring in my pocket. Grumbling, I once again shifted the weight of my bag in order to dig around in the pocket...

Straight Sex
3 years ago
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Military Escort

It’s my first time in Newcastle Upon Tyne. My first time up north. I’d fallen in love with your accent but we’d never made it up here together. We’d always planned to. We’d said we’d come up, visit your folks and I could watch a match. I look out the window of the hotel and watch the hordes of black and white-clad men parading down the road from St James Park. The chants and songs rising up leave me in no doubt as to the paternity of the referee. I look at my watch. It’s almost 5 pm. I really...

Uniform
2 years ago
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Military Quartes

Our quarter had 4 small apartments, in each apartment lived an official. Now during my stay my dad had to go home due to an emergency, i was supposed to go with him but i didnt wanted to. I convinced him a lot to let me stay back. After a lot of persuasion he finally let me stay there. Since he was a high ranking doctor in the army he had two soldiers appointed for his protection, he asked them to take care of me and stay with me at all times. I knew these soldiers, Harry and Rob. They were in...

4 years ago
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Military DelightsChapter 1 Prince Habib

The first encounter between His Magnificence, the Emir Mahmoud Abdullah, may he live for ever, and the despised son of the Khan of Tirfil was at the celebrations for the tenth anniversary of the Emir's accession to the throne. A number of notables had been invited to attend the ceremonies, during which a competition was held to select a Special Concubine to the Emir. The notables were each offered the privilege of deflowering one of the losing competitors, and the Emir recalled with distaste...

3 years ago
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Military DelightsChapter 2 The Visit

It was with this background that the Emir was surprised to receive an intimation that the Foreign Minister of Tirfil wished to pay a formal visit to Ghada Baroud, the Emir's advisor on Diplomatic Matters, in Kobekistan. "Why are you asking me? It's you he wants to see," asked the Emir. "Master, it is forbidden for any Tirfilese to enter Kobekistan. Only two aircraft have tried in the past year, both helicopters, and both bearing the markings of the Tirfilese army." "What happened to...

4 years ago
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Military DelightsChapter 5 Sima And Tajwar

When they heard the soldiers rampaging down the street, Sima and Tajwar cowered in the unlit cellar of their small house. Sima was a widow whose husband had died only months after the birth of Tajwar, her daughter. In the ensuing fifteen years they had lived in the small house, and lived well, on the proceeds of selling his business and the large mansion he had owned. As was to be expected, Sima had led a completely celibate life, and Tajwar was a virgin. In three weeks time, she had expected...

1 year ago
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Military DelightsChapter 6 Jahiz And Siharn

Jahiz was too old and infirm to fight in the army, but he was determined to protect his home and his belongings, especially his only concubine, the delicious Siharn, forty years younger than him. He was no longer able to use her properly, but he enjoyed her mouth on his body, and did not want her defiled or enslaved by this invading army. He had his loaded jezail on his knees and the girl was well hidden in the linen chest on which he sat. When six dragoons burst in to the house he raised the...

3 years ago
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Military DelightsChapter 7 The Infantry

There were six of the infantry in the patrolling platoon who were ordered to clear any resistance out of a short street of small houses. Their orders were to take any men they found between the ages of fifteen and sixty to the town square as prisoners. It was not a street where they expected to find much in the way of wealth, and so they also expected little resistance. Any males they found would probably be deserters, and there wouldn't be much loot either. They went the length of the...

4 years ago
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Military DelightsChapter 8 Bukhari

Bukhari, a seasoned soldier, twenty-five years old, who had fought against the Tirfilese incursions in the desert for six months, was the first to finish one house, having found nothing of interest in the almost deserted hovel. True, there was an old woman there who swore at him, but he didn't bother with her, and after a perfunctory check of all the rooms he moved on to the next house on his search pattern. As he went into the first room there was a loud report from the rear of the house...

3 years ago
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Military DelightsChapter 9 Gadhi

Kicking the door of his first assigned house in the approved television manner of attacking troops, Gadhi entered cautiously with his rifle at the ready. The house appeared empty as he checked the ground floor, then he heard a small noise from the upper floor. Making his way very carefully up the stairs he found a woman in an abaya with two small children crouching behind her skirts. Other than some rugs on the floor for sleeping on there was no furniture and so nowhere for anyone to...

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