Caught Crossdressing By Aunt Sharon free porn video

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Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I should probably talk about before you leave. Your nephew is somewhat different from what you might expect from the average sixteen year old boy. Sharon, you haven't seen him in over a year, he's changed. He doesn't spend much time with the other boys in the area, he seems to be more a loner." Rita and Sharon were sisters. Rita, Brad's mother was thirty-five, married to Tom and lived the unsatisfied existence of the average house wife. She had been a lovely girl in her youth, attracting quite a bit of attention from all the boys. In her senior year, she fell in love with Tom Hennesey, the high-school football team's star quarter back. After the victory dance, convinced that Tom also loved her, she agreed to go to a local motel with him. Tom, typical of most boys that age, had been neither gentle, nor concerned with her needs, only interested in his own satisfaction. She'd lost her "maidenhead", suffered considerable pain, was not sexually satisfied, and needless to say was confused by Tom's selfishness. Even worse, she became pregnant with Brad. Tom and Rita discussed their alternatives, agreed to marry and with the help of both sets of parents, set up housekeeping. Over the years, all her dreams of the good life went out the window. With nothing to look forward to, Rita eventually slipped into a casual attitude towards her appearance. She gained thirty pounds, wore less attractive clothes and became exactly what she looked like...an average mother/housewife. Rita was secretly jealous of her sister Sharon. Not because Sharon was younger by seven years, but because her life was more interesting and exciting. Sharon was the real beauty of the two sisters. She had enjoyed the attention her looks brought her, but was wise enough not to get trapped as Rita had done. Boys, and later men, never became so important in her life that she sacrificed any of her goals for them. Sharon was 5'9" tall, perfectly proportioned (possibly a bit too large in the chest), with long dark hair. Her features where chiseled in the classic mold of a young Liz Taylor. Every man or woman she met was immediately struck by desire or jealousy...sometimes both. Sharon had started working at a bank right after graduating college in a management training program. This meant she started out as a low-paid teller and if she did well she would move up the ladder. It was the typical way banks were able to get college educated women to work for them at low salary levels. Her work performance and beauty got her noticed by the President of the bank, who made her his administrative assistant. After the first month in the new position, her boss came to her and asked her out to dinner, supposedly to discuss her performance. For the next twelve weeks he courted her lavishly, showering her with gifts, then asking for her hand in marriage. Sharon thought long and hard before reaching a decision. He was a nice enough man and offered her the opportunity of a wealthy lifestyle. Even though he was thirty-five years her senior, she felt that was of little consequence. Sharon was worldly enough to understand why he wanted to marry her. She didn't love him and they both knew it. Therefore, when he promised to be less than demanding...sexually, she was tempted to say yes, but she still hesitated. What finally convinced her to marry him was his offer of a pre-nuptial agreement. The agreement guaranteed her a large settlement, after seven years of marriage...or his death, whichever came first. For three years her life was a whirlwind of parties, expensive clothes, cars and travel. As far as intimacy, he kept his promise. Sex to her husband was the typical "slam, bam, thank you ma'am, once a month event". This was more to reassure his aging male ego, than for any other reason. She "suffered" through those nights bolstered by the knowledge that the marriage would end in seven years and she would be set for life. When she was notified of the commuter plane crash and his confirmed death, she shed not a tear. The fact that she inherited everything "helped" console her and when an out-of-state bank offered her a huge price for her controlling bank shares, she found she was now a twenty-five year old widow with more money than she had ever dreamed possible. Sharon had offered a large piece of the inheritance to her sister, but Rita's husband had refused to accept any of the "blood money". This refusal caused an uncomfortable split between Sharon and her brother- in-law. She only visited when she was sure Tom was away on business. Rita in order to keep peace couldn't even call her sister since Tom checked the long-distance phone bills. This didn't stop Sharon from calling and keeping in touch with Rita and Brad. Whenever she did visit, she would insist on taking both of them shopping and then out to dinner at the most expensive restaurants and stores. This was her way of making up for not being there on a regular basis. Brad, of course, loved when his Aunt came to visit, what young boy wouldn't. As he grew older he began to realize that she never visited when his father was around. This hurt him deeply. His Aunt was the person he loved the most. Tom, Rita and Brad didn't have a peaceful homelife. Father and son felt no warmth towards each other. Brad had not inherited his father's physical prowess and was a definite disappointment to Tom. This worsened the home situation even more, to the point that Brad began to "hate" his father and Tom, in response, further ignored his son. Rita was confused by her love for her son versus her love for Tom. This sent mixed signals to Brad. Because he received no emotional satisfaction at home, Brad replaced a child's normal affection for his parents with affection for his Aunt and wished he lived with her. He turned this desire to live with her into a fantasy in which he was her son instead of Rita's. As many young boys do, he began to use her image in his sexual fantasies. After his first fantasy, in which she seduced him, he was hit with guilt induced tears and promised himself he would never again view his Aunt as a sex object. However, the next time he got the urge to masturbate, Aunt Sharon again appeared as the sensual woman in his fantasy. With each fantasy re-enactment his guilt lessened. Tom felt that Brad was the reason he had been "trapped" into marrying Rita. Oh, he assumed he loved his wife, but still wished they had waited to marry till he had sown a few "wild oats". Besides, Rita no longer looked like the woman he had married and no longer excited him. More and more, he found himself thinking of having an affair with a secretary where he worked. These frustrations manifest themselves in the form of mental and physical abuse towards Brad, who sought refuge in his confused mother's arms. This strained situation continued till one day Brad, in a fit of anger, shouted at his father. "I wish I could go and live with Aunt Sharon so I could get away from you!" His father was just as quick to answer, "If she'll take you, you can leave right now!" Rita, realizing where this was heading, stepped between father and son and quickly suggested Brad "visit" his Aunt for the entire summer. Then when summer was over, everyone would sit down and talk the situation through and come to a resolution. She hoped that this cooling off period would bring about a reconciliation. That's why Sharon had come, to take Brad back to Columbus to live with her. Rita was also concerned by changes she noticed in her son's behavior. At first, she suspected what every parent fears...drugs. But after reading about the symptoms and realizing they weren't present in Brad's behavior patterns, she accepted Brad's behavior as the outward effects of puberty. Rita had caught her son looking up her skirt, down her blouse and peeking through the bedroom keyhole. While this made her uncomfortable and she criticized his actions, she secretly enjoyed knowing he found his mother attractive enough to spy upon. Brad's spying made her feel wanted, now that her relationship with her husband had soured. In addition, Brad showed interest in feminine clothing, especially women's undergarments (he used his mother's panties to bring himself to orgasm). She discovered unexplained runs in her pantyhose and misplaced articles of her lingerie. While she didn't understand all the actions, some were easily explained by the fact he was "growing up". One day, left alone in the house he decided, "If the panties feel so good against my dick, I wonder how they'd feel if I wear them?" This was his first step into crossdressing, but only the first. From that moment, whenever he was alone, he would sneak into his mother's room, carefully open her lingerie drawers and borrow a bra, panties and hose. His mother never kept her drawers neat, so she never discovered his temporary thefts. He continued dressing up in the borrowed feminine clothing, experimenting and actually becoming relatively adept at wearing his mother's attire. He also practiced feminine mannerisms in front of a full-length mirror. When dressed and standing before the mirror he created fantasy conversations speaking in a girlish voice which he managed to develop with practice. Once tempted, his young mind became obsessed with women, their clothes and their bodies. He became an expert on lingerie and foundation garments. He discovered the purpose each item fulfilled towards enhancing a woman's figure. Matching his mother's lingerie labels against the descriptions in the catalogs he learned to distinguish the subtle differences of each material. Using this same method, he studied dresses, skirts and blouses. Diligently applying himself, he soon became expert enough to determine what a woman was wearing and the material from which it was made. Hearing a noise, both women looked up as the front door opened and Brad walked in. Seeing his beloved Aunt, he rushed to her and leaned over to give her a hug and kiss. In his excitement to see her, he lost his balance and fell across her lap, his right hand falling between her nylon clad thighs. Sharon's instinctive reaction was to close her legs, thereby trapping his hand against the firm flesh of her upper thighs. The absurdity of the situation became immediately apparent and the women began to roar in uncontrollable laughter. This gave Brad the opportunity to extricate his hand and right himself. Embarrassed, he offered profuse apologies to both women, but especially his Aunt. "It's alright Brad," she stated. "I know it was just an accident, it's better it happened here, instead of in the presence of strangers. Besides, it's been a long time since I've had that much fun with such an aggressive young man," she teased. Brad was embarrassed. Not knowing what to say, he stood there trying to hide the blush plastered across his features and the erection in his pants. Rita, seeing the bulge in her son's pants, realized her son's predicament. Catching her sister's attention, she silently communicated the situation, as all grown women are able to do. Sharon understood immediately. Rising, she threw her arms around Brad and whispered, "I'm only kidding, don't be embarrassed, nothing serious happened and no damage was done. After all, I'm your Aunt. If you're going to live with me this summer we'll probably have other accidents around the house. Don't let what happened embarrass you. It doesn't bother me, so don't let it bother you. Now give me a big kiss to make it all better." Brad kissed his Aunt and asked, "Am I really going to live with you all summer?" "Of course, it's all decided. In fact, since I have a dental appointment tomorrow, we're driving back right after lunch. That way we'll have time to get you all settled in. Are you packed?" Rita started laughing, "He's been packed for two days, you'd think he 'hated' being with his mother", she chided. "Oh mom! It's not you, I'll miss you, it's just...well you know." "Yes dear, I know. Don't worry I understand. Now let's have that lunch, so you two can get going." After lunch they loaded the car, said good-bye to Rita and headed out of Chicago. Aunt Sharon explained that the drive normally took seven hours, but they would stop for a break in Indianapolis. Sharon spent the next hour or so asking questions of her nephew. At first he was evasive, not wishing to disclose anything about the situation at home, but as he became more comfortable with his Aunt, he opened up to her. She learned about Tom's abuse and Brad's closeness with her sister. She discovered that Brad, within the last 18 months, had also discovered the female gender. Unfortunately for Brad, it had arrived, just as his relationship with his father had worsened. After an hour of driving, Sharon turned south on I-65 towards Indianapolis. This stretch of road is considered one of the most boring in the mid-west. Flat farm land as far as the eye can see, the exit signs being the only breaks in the monotony. Traffic was extremely light so she settled back, in the most relaxed and comfortable position available and set the cruise control to the speed limit. Her body adjustments caused her 18" skirt to rise above the welt of her nylons. She could have easily tugged the hem back in place, but instead, chosed to ignore it. This was the manner in which she normally drove and decided she wouldn't change her entire lifestyle because of Brad. Sharon said to herself, "He's only a teenager and probably thinks of me as a second mother. In fact, I'll suggest that he views me in that light. If that works, It'll mean fewer changes in my lifestyle." Glancing over at her nephew to determine the effect of her exposure, she found him curled up...asleep. Smiling to herself, she returned her attention to the road. Brad wasn't really asleep. He had chosen to avoid further questions by playing "possum". Peering between his drawn eyelashes he became aware of his Aunt's exposed thighs. Mumbling softly, as if asleep, he adjusted his position in order to obtain a better view and at the same time, moved his hands in order to cover his crotch. Sharon, hearing him moan, again glanced over at Brad, then smiled down at him as a thought ran through her mind. "I hope it works out between us, I think I'd like Brad to live with me on a permanent basis. I've always wanted my own child. I would've preferred a daughter, and I wish he were younger, someone I could better relate to, but having a son like Brad would be wonderful. Of course I'm going to have to make some adjustments in my lifestyle...especially Sandy." She smiled to herself as thoughts of Sandy, her lesbian lover came to mind. After her husband had died, Sharon found she felt no need to become romantically involved with another male. Unfortunately, her sexual needs still existed. She and her roommate, during their college years, had played "girl games" in the secrecy of their apartment and had "discovered" each other. Though, she never spoke about those "old" days, she had enjoyed the sexual experimentation and tender satisfaction they had shared. Sharon, remembering those blissful moments decided it was time to try the gentler sex again. After a few embarrassingly un-successful and pathetic attempts, she resigned herself to masturbation. That's when Sandy came into her life. Sandy was the bank examiner involved in the audit when Sharon sold her bank shares. The two women immediately saw something in the other's eyes, had lunch together, admitted they were strongly attracted to each other and became lovers. Within a short span of time, Sharon had invited Sandy to move in with her and Sandy agreed. Sandy's job caused her to be away for extended periods. Whenever she was in town, she spent every available moment with Sharon. Sharon's realized how much she missed the "bitchy" blond who shared her bed. Sandy's current absence, over three weeks, caused sexual desire to creep into her thoughts. She soon realized, that thinking about Sandy was causing her pussy to become damp with desire. Slipping her left hand to her inner thigh, she gently stroked the warm flesh above the welt of her nylons. Stretching her long nailed index finger under her drawn-up skirt, she found the tip of her nail was barely short of her panty cover crotch. Adjusting her hand an inch closer made all the difference in the world. Now she could "tease" the silky smooth material holding back the puffy entrance to her womanhood. Drawing her nail slowly upward caused the tightly drawn nylon panty material to sensually vibrate against her moist opening. Enjoying the ever increasing exhilaration that came with each finger-stroke caused her to softly "mew". Still not fully satisfied with her position, Sharon thrust her hips forward. Now the nail tip located the demanding bud of her blood-filled clitoris as it pushed against the now soaked crotch of her panties. Back and forth, slowly, moving only the last digit on her finger, she flicked the now protruding mound of flesh, fantasizing it was Sandy tongue instead of her own finger. Building her passions to the impending brink of orgasm, she paused, remembering where she was and who sat next to her. Realization was a bucket of cold water. There was no doubt that her impending climax would wake Brad. Disappointed, but also adult about the situation, Sharon chosed the respectable course. Giving herself a last firm flick, she forced her hand away, hiding her actions by an adjustment of her skirt. With a last look at Brad, to reassure herself that he was still asleep, Sharon returned her mind and eyes to the road. Brad, had seen everything! Disappointed and ecstatic at the same time. He could now add a touch of sensual realism to his fantasies. Remembering what he had just witnessed, he really fell asleep, dreaming of future voyeur episodes he might experience while living with his Aunt. The rest of the trip was uneventful. They stopped in Indy, had a snack and continued their journey. They arrived in Columbus, shortly after sunset. Sharon gave him the grand tour of her home. Brad was truly impressed. While it wasn't quite a mansion, it was the largest and most luxurious house he had ever been inside. When she showed him her master bedroom, he became sexually excited. It was so ultra-feminine, with its frilly curtains, lace bedspread and pastel walls and lamps. The room was dominated by the large "four poster" king-size bed with it's sheer drapes tied back at the corners. The pictures on the walls were definitely well suited to the color scheme, if not a bit strange to his youthful mind. They depicted beautiful naked women, alone or in pairs, sensually reclining upon couches and beds. The women's genitals scarcely hidden by a crossed arm, raised thigh or perfectly placed pillow. Brad was tantalized by the suggestive nature of the paintings and made a mental note to sneak back into his Aunt's room to further study the prints. Hiding his erection, he asked, "Where will I sleep?" "You can have your choice," his Aunt answered. "There are two other bedrooms to choose from. Actually there are three, but the one next to mine is used by a friend who visits me whenever she's in town. She keeps some clothes here and rather than move her things, I'm sure you'll be satisfied with one of the other two. Let me show you." After being shown both rooms, Brad picked the more feminine of the two. When his Aunt pointed out he might be more relaxed in the other since it was "neutral", he stated he particularly liked the feminine bedroom because its attached bath room contained a spa type bathtub. He explained he preferred baths over showers. This explanation more than satisfied his Aunt, who then recommended a possible redecorating. Again he assured her it was fine. "It doesn't bother me, let's not change it until we find out how long I'll be staying with you." "Well, if that's all settled do you want me to help you unpack?" she asked. "No thanks, Auntie, I can manage. Besides you must be tired from the long drive, why don't you relax and I'll join you after I'm finished putting away all my stuff." Sharon admitted she was tired, wanted to change into more relaxing clothes and would see him downstairs in the den when he finished unpacking. Before leaving she said, "Brad, I'm very happy you're here and I'm sure we'll get along very well. However, I want you to understand that it's been a long time since I've lived with anyone, so I've come to like things a certain way. I'll expect you to respect and comply with my wishes as if they were your mother's. In a sense, during your visit, it might even be better if you think of me that way. You'll have some chores just like at home, nothing difficult. This is a very large house, but since I like my privacy, no servants. I have a cleaning lady twice a week who handles the 'big' stuff, but picking up after yourself, etc., is your responsibility. We'll talk more about that in the morning. Now if you don't have any questions, I'm going to clean up a bit and go relax. Any questions?" Brad assured her he would do anything to please her, wouldn't be a bother and thanked her for taking him in for the summer. Throwing his arms around her, in a surprise move, he hugged and kissed her. The kiss was just a hint longer than Sharon expected and the hug was also more familiar. After a few more "thank-you" and "you're welcome" comments...Sharon left the room. Brad spent the better portion of an hour unpacking. He had declined his Aunt's help because he didn't want her to see some of the items in his suitcases. Along with his normal clothing, he had a cache of feminine "pretties". These included panties, a bra, a garterbelt and a pair of nylon hose. He had to find secure hiding places that would not be discovered by either his Aunt or the cleaning lady. Finally, he decided to leave them in his supposedly empty suitcase which he stored in the back corner of his walk-in closet. Satisfied, he removed his clothes, changed into a pair of blue cotton pajamas and went down stairs to find his Aunt. Meanwhile, Sharon had also changed into a pair of pajamas. Hers however were white satin lounging pajamas with baby pink and blue designs at the collar and cuffs. Normally, in the evening, she wore diaphanous peignoir sets around the house, but chosed the pajamas since her nephew was there. Realizing, with regret, that changes were indeed necessary, she again hoped they could be minimized. Sharon was a woman who enjoyed being feminine. All her lingerie was the finest, most expensive available. Oh, it wasn't all that exotic... just sensual. One of her pleasures in life was the freedom to express her sensuality in the privacy of her home. One of the great joys of her existence was the thrill of being feminine. The only disappointment of her sensualness was she couldn't let anyone other than her lesbian lover know how much pleasure she derived from secretly expressing her femininity through her lingerie. As Brad entered the den, Sharon said, "I thought you might be hungry so I've prepared a lite snack. It's just cheese, pat'e and some crackers. If you don't care for pat'e we can order a pizza or something." "Pat'e sounds wonderful! I am a little hungry and that will just hit the spot. I like pat'e. Mom introduced me to it two Christmas's ago when you sent that gourmet basket." Brad moved to the couch and sat next to Sharon. They spent the evening enjoying the snack and each other's company. Every now and then, as Sharon reached for a morsel of food, Brad caught a glimpse down the throat of her satin pajamas. He couldn't see much, just the beginning rise of his Aunt's right breast. He tried to be careful, but thought she caught him staring at least once. Since she said nothing, he wasn't sure. Sitting there, next to an adult woman (the woman his fantasies were built around), in her sexy pajamas, smelling her perfume and observing the raised "pock" marks her nipples made on the material was more than he could handle. Thinking about what was barely hidden behind the material got him excited. Brad developed an erection! Trying his best to adjust the folds of his pajamas, he dropped a cracker into his lap. Sharon had definitely caught him staring down her pajama top. Realizing he couldn't have seen anything, she excused it as boyish curiosity and made no effort to adjust her clothing. When she caught him staring at the nipple marks however, she decided that he needed to be taught a lesson. When he attempted to adjust his clothing, she realized he was sporting an erection. Amused, surprised and curious, she watched as the cracker fell onto his lap. Acting quickly, she reached her hand into his lap as if to pick up the cracker before it fell to the carpet. Instead of the cracker her hand encircled his maleness. It was much bigger than she had expected. Just as she prepared to release Brad and sternly criticize him for his "pee king" ...he moved. Brad was caught by surprise...to say the least! When his Aunt's hand grasped his dick, he pushed his shoulders back against the couch, his heels into the carpet and his hips up off the seat. This, instead of helping the situation, made it more embarrassing. His Aunt's hand reacted, holding him tighter! His pajamas outlined his hard-on so that neither he nor his Aunt could make-believe it didn't exist. Not knowing what to do, he froze. Searching his Aunt's features for a hint of direction, his mind raced. "How could I be so stupid! Aunt Sharon must realize I was peeking at her tits. She'll probably send me back home and tell mom. I'll be grounded for life! Before he could apologize, she released him, then spoke, "Well, I think we'd better talk! I want you to tell me what you were doing to cause that erection. We can't have you in a constant state of arousal just because you're living with me. I'm not going to dress like a nun, just because you're here. I expect you to tell me everything young man, and it better be the truth! What have you got to say for yourself?" With his head down, Brad began. He explained he had really been awake and had observed Sharon "playing" with herself in the car. He stated it was the first time he had seen a woman tease herself and he not only became excited but also came to realized his Aunt was more than just his Aunt, she was a very sensual woman. Now, he admitted, he was sexually turned on by her. Next he told Sharon how he had stolen looks down the top of her pajamas and while he hadn't really seen anything, just knowing what was there, caused his dick to become semi-erect. Then, when she had leaned back and he saw where her nipples were pushing against the material, he had lost control. His dick became rock hard as his mind visualized the pouting nipples hidden behind the material of her pajama top! After admitting all, he said, "Aunt Sharon, I'm really sorry! I didn't mean for this to happen, it just did. I can't help thinking about women and their bodies...and yours especially. Your the prettiest and most sexy woman I know! I love you! Please try to understand, I can't be the only boy or man that has stared at you, you're so absolutely beautiful, men must stare at you constantly. Even before I came to live with you, I would fall asleep and dream you were my girlfriend. Whenever you visited I would be in seventh heaven. I love the way you look and smell and especially how you hug me. I know I shouldn't get sexually excited when I'm near you because you're my Aunt, but sometimes I just can't help myself. If you let me stay, I promise to control my feelings and I won't try to 'peek' at you. I love you, even more than mom. Please give me another chance?" Sharon didn't know what to say or do. Her plan had been to embarrass her nephew and maybe even punish him for his actions. After hearing his reasons, she realized she was also at fault. If she hadn't exposed herself in the car and "played" with herself, maybe he wouldn't have changed his perception of her. It was obvious, he had a "crush" on her. On top of everything else, she liked it! Sharon realized her nephew was in the throes of puberty and remembered how strong her own emotions had been when she went through it. "He actually thinks I'm the prettiest and sexiest woman in the world!" she mused. "I've got to do something, I can't let this continue all summer, but what?" Looking at Brad, she began, "Brad, what you saw in the car was wrong. It wasn't wrong that I did it, it was wrong that I did it when you were there! Women masturbate as much as men. We have sexual needs also. So, for what you saw me do in the car, I apologize. But you had a responsibility, as my nephew, to not look, or to 'wake-up'. Tonight, you compounded the problem by your peeking at my breasts and by thinking of me as a sex object. Women are not 'toys' for men to play with or to use. I believe you're sorry and will try not to let this happen again, but you must be punished. If you agree to a serious spanking, I'll forget this incident and give you one more chance." Brad interrupted, "Oh Aunt Sharon, if you give me another chance, I'll take whatever punishment you think is fair!" "Don't agree too quickly, this will be a serious spanking. I can't and won't allow you to think of me, your Aunt, as a sex object. Also, I want you to re member this spanking so that if you get tempted again... you'll change your mind." Lowering his head, he said, "Aunt Sharon, will you give me the spanking I deserve?" "Since you asked so nicely, yes. Now, go upstairs to my bedroom, take off your pajama bottoms and wait for me." Brad was stunned, he hadn't expected a "bare-bottom" spanking, but from the look on his Aunt's face, he knew better than to protest. Realizing he had no other option, he headed for his Aunt's bedroom. Why Sharon had decided to administer a spanking she had no idea. It had flowed out in the discussion and at the last moment, she realized that the embarrassment of it being on his naked butt would go a long way towards curbing his desires for her. She also decided to wait about ten minutes to heighten his fear. Lighting a cigarette, she remembered the spankings she had received as a child. The last one had been administered by her mother at sixteen. Her mother had caught her smoking behind the garage. She had enjoyed the spanking, even though it was painful. Putting out the last of her cigarette, she went upstairs. Entering her bedroom, she moved to her vanity and sat with her back to the mirror. Not saying a word, nor looking anywhere other than at Brad's face, she motioned him to place himself over her knees. Brad had used his hands and the tail of his pajama top to cover himself so his Aunt wouldn't see his crotch. Moving to her satin covered lap, he positioned himself across it. His cock and balls falling into the opening between her satin covered thighs. The shock of the first slap was a surprise. His Aunt wasn't holding back, as he had hoped. With each succeeding fall of her arm the pain increased, but he soon realized, it was also exciting. To be spread across a sexy woman's satin covered lap, with her in total control, made him momentarily forget the pain. Now he felt his dick rubbing against her satin covered thighs. Feeling his cock become hard he began to take pleasure in each stroke, since her thighs moved in response to the swing of her arm. Sharon had initially intended 10 slaps, 5 on each buttock. As each stroke fell she realized she was enjoying herself. Then when she felt his hardness between her thighs, she understood he was enjoying it also. She knew she should stop...but her own sense of enjoyment wouldn't allow it. It felt exciting to have her nephew under her total control. She was now treating the youth as a sex object for her own satisfaction. When her arm began to tire and she sensed his needs rising, she stopped. Reaching behind her, she grabbed the jar of Noxema from her vanity. Unscrewing the lid, she inserted two fingers, scooped out a generous amount and began to rub it into the flame-red skin of Brad's butt- cheeks. Explaining to him that this would help "cool-down" the pain. It would also give him enough time for his cock to shrink, thereby eliminating her having to recognize the punishment hadn't worked. Sharon had decided Brad would receive more spankings in the future and didn't want him to realize she had noticed his enjoyment. When she no longer felt the hardness between her thighs, she released him. He stood before her, both hands massaging the cheeks of his ass, no longer concerned about his nudity. Sharon, risking a look at his equipment was impressed that one so young was so well endowed. When she asked him if he had learned his lesson, she received his promise and then sent him off to his room, but not before she took a final look at his cock. After he left, she shut the light and brought back the memory of Brad's spanking. With a smile on her lips, she fell soundly asleep. Brad, left her room, not even bothering to put on his pajama bottoms. The first thing he did upon entering his room was to stand before the full-length mirror and examine his rosy-red ass. Touching the tender skin, he said aloud, "Boy, when she gives a spanking, she's serious about it!" Then thinking back on what had occurred, he smiled and said, "It's a good thing Aunt Sharon never saw my hard-on, I can just imagine what that would have cost me." Deciding to try to sleep away the burning pain, he stretched out across the bed. Not bothering to cover himself, he lay there going over the exciting events of the day. The last thing he remembered, as he fell asleep, was his hard-on rubbing between his Aunt's satin covered thighs. The next morning they both slept late. Sharon made them a quick brunch and all was well again between the two, the events of the previous night forgotten. Sharon, during the meal, explained his new duties around the house and asked how his butt felt. After being assured that the pain was mostly gone, she stated she had a few errands to run before her dentist appointment. When she returned, she planned on taking him shopping. She explained, "I'm sure you didn't pack enough clothes in those two suitcases, so let's get a late lunch and go to the mall and get you some additional clothes to last through the summer." Brad asked if he was to go with her on her errands? Aunt Sharon said she usually had to sit and wait at the dentist's office, so if he didn't mind being alone, she would come back and get him after she finished at the dentist's. This suited him much better. When she left, he went to his room and began collecting his feminine attire. Then a thought came to him, "Why don't I take advantage of Aunt Sharon's absence and do a bit of snooping. She said she wouldn't be back for about three hours. If I don't find anything interesting I'll still have time to change into Lynn (his alter ego)." As he walked towards his Aunt's bedroom he passed the spare bedroom where Sandy kept her stuff. Trying the door, he found it unlocked. He decided to investigate that room first. If he disturbed something in the friend's room, he rationalized, it was less likely to be noticed and/or questioned. Opening the door, he discovered the room was almost a duplicate of Aunt Sharon's, as feminine, just done in different colors. Opening the door of the walk-in closet, he found the light switch and flipped it on. It was not what he expected! The closet was half-filled with dresses, skirts, blouses, etc. He had expected only a few outfits, just enough for his Aunt's friend to get by on when she visited. The woman could have lived here for a month or more with all these clothes. Looking at some "built-in" shelves, he was again pleasantly surprised. They held four or five different wigs, all in different styles and shades and a collection of sweaters. The sweaters were packed in clear plastic zipper bags. In addition, there must have been twenty pairs of shoes, mostly high heels. "This is going to be wonderful! I can dress-up and Auntie will never realize it!" Stripping to his shorts, he select a dress and held it up against his body. It looked to be almost a perfect fit. Maybe a bit long, but heels and my false breasts will raise the hem, he mused. Replacing the dress, he selected one outfit after the other. Picturing himself in each, he began to get excited over his new-found treasures. Where before he had had a few outfits to change into, now he realized Lynn had, for all intents her own complete wardrobe. Each succeeding outfit raised his level of excitement. The different colors, designs, materials and the variety were overwhelming. "I wonder what lingerie Aunt Sharon's friend left here?" he said aloud. Deciding to "see" what was available in the dresser, he carried the dress with him and returned to the bedroom. There he lovingly placed it upon the bed and moved to the dresser. Standing before it, he slid open the top drawer. It was full of multi-colored bras and panties. He immediately realized that the owner must not be concerned with neatness. The contents had obviously just been tossed haphazardly into the drawer and "pawed" through when she needed something to wear. No matter how he left the "pretties", he would raise no suspicions. "What a delightful situation!" he said aloud in his best Lynn voice. Sliding open the next drawer, he found it contained slips and nightgowns. This lingerie was of course much neater, but still not necessarily sorted. Emptying the contents onto the top of the dresser, one at a time, enabled him to study the items. The night gowns were made of the sheerest and most diaphanous material he had ever seen. "When this woman wears these she doesn't hide much," he thought aloud. Unfolding a couple of items, he discovered the method the woman used to fold both nightgowns and slips to be the same and simple to duplicate. He knew he would have no trouble replacing everything just as he found it. The third drawer was filled to the brim with nylons and pantyhose in different shades and colors. These were again just stuffed in as were the contents of the first drawer. The bottom drawer held a panty girdle and various garter belts. Moving to the three drawer vanity he found make-up, false eye-lashes, brushes to apply cosmetics and in the second drawer, under some socks... a vibrator. The bottom drawer held two book-like objects, both covered in hand-tooled dark leather. The first was a locked diary. It would take some careful work to get past the lock, but Brad knew he would find a way. Maybe he could find the key to it hidden somewhere. The idea of reading a unknown woman's inner thoughts was too strong to resist. Opening the second book he found it was a photo album. It held 20 vinyl pages, each page able to hold two pictures on each side. It was about half-full. The first page, an unknown woman (he supposed it was his Aunt's friend), dressed in garterbelt and nylons, had her head buried between the thighs of another woman dressed in the same manner. The other woman's identity became clear in the next photo... It was his Aunt! Brad couldn't believe his eyes. Here was his naked Aunt, the same woman who had spanked him for staring at her while fully dressed, involved in lesbian sexplay. After the spanking, he had assumed his Aunt wasn't interested in sex, now he knew better. "Boy, was I wrong about her!" Quickly turning the pages he found the two women displayed in various sensual positions. He found scenes he had never even imagined. He could see the look on Sharon's face was one of wanton desire. After rushing from one picture to the next, he came to the last one. Having been in such a state of excitement, he hadn't really had time to study each shot, he decided to go through it a second time. Flipping to the front page again, he now looked at each photo in detail. Both women were obviously pretty and had gorgeous bodies. Not being able to "stand" anymore, he rushed to the john, grabbed some tissues and after just a few strokes, came in his hand. Cleaning himself up, he then returned to his discoveries. Looking at the clock on the nightstand he decided there was plenty of time to try some of the outfits before his Aunt returned. Going from drawer to drawer he made his lingerie selections. Removing his shorts, he began the change from the male Brad to his other persona, the female Lynn. Placing a black lace garterbelt around his waist, he slipped the hook into the loop and spun it around. Then balling the sheer, black nylons, he alternately inserted one foot after the other into the re-enforced toes. Grasping the balled-up material at the toe of his right foot, he "slinked" it up his out-stretched leg and attached it to the dangling garters at his thigh. Repeating the process on his other leg. French- cut white silk panties with bone colored lace and a matching under-wire bra, each cup stuffed with two additional nylons, followed. A red polyester full slip and black and white trimmed coat dress were next. Within a relatively short time he was fully dressed as Lynn. Returning to the closet, he selected a pair of black and white spectators which matched the dress he had selected. Turning towards the shelves, Lynn decided upon a shoulder-length, honey-blonde wig. Placing it on her head, she moved to the vanity. Brushing the borrowed wig into its pre-shaped shoulder flip until he was satisfied that it laid just right. Deciding on which lipstick and eye-shadow took but a second or two. A little blusher, to highlight his cheekbones and a pair of clip- on earrings completed the transformation. Perfume was too dangerous, he decided. Peering into the mirror...Lynn felt very satisfied. She actually was quite lovely. Her natural small features went a long way towards her "passing." Standing, she raised her hem and re-adjusted each nylon. Holding up the skirt portion of the dress to her waist she smiled... no revealing bulge. Lynn had become quite adept at controlling her hard-on whenever she wanted, last night being an exception. She had thought about this ability. In the beginning, she got hard whenever she crossdressed. Now, she no longer got overly excited by the gender transformation. Lynn still desired crossdressing, but didn't get a hard-on just because of it. She wondered if it was possible she should've been born a girl... but wasn't sure if that was the answer. "Oh, right now it doesn't matter. All that counts is I can change my gender whenever I please. After I grow-up and go out on my own, I may look into the possibility of a sex change operation, but for now, this is enough. Now I think I want to take a walk through the house." Loving the way the feminine clothing moved as she walked, Lynn left the bedroom and proceeded to walk the hallway. Back and forth she swished the entire length of the hall. The clothes and heels fit perfectly! This was going to be heaven living with his Aunt! Deciding she was thirsty, she turned, walked to the circular stair case and lightly grasping the railing, she made her way downstairs copying the style she had seen in an old Lorretta Young movie. Halfway down, she heard a noise and the front door opened. Caught, she had nowhere to hide! In walked Aunt Sharon. She saw Lynn immediately. A look of surprise, followed by one of confusion, recognition and finally amused anger. "What are you doing? You're wearing Sandy's dress. What's the meaning of this? Come down here, right now!" Brad always knew his secret would someday be discovered, but still tried to stammer an explanation. His Aunt would have none of it. "I said get down here, now! I guess the punishment you received last night didn't leave much of an impression." Brad meekly followed his Aunt into the den, where Sharon sat down on the couch and motioned him to stand before her. "Now young man and I obviously use that term loosely, explain yourself." Brad explained all the crossdressing details of the last eighteen months as his Aunt listened in growing astonishment. Noticing the bemused look on Sharon's face, Brad took heart. Maybe she wasn't as mad as she projected? He continued the story of his feminization and brought her up to this morning. Sharon stopped him at this point in the narrative and said, "Let's go up to your room where you will show me the female clothes you brought along with you. That way I'll know if you're telling me the truth." Brad led the way up the stairs and down the hall to his room. Sharon, walking behind him, marveled at how well he mimicked the mannerism and walk of a young woman in heels. She had to admit to herself, "If I didn't know she was my nephew I'd swear she was my niece! Look at the way she gently rolls her hips as she walks and she really has great legs and a fine ass! Lots of young women would love to look that good from the rear! Of course she doesn't look bad from the front, either. She needs help with her tits, they're a bit off center and one is slightly lower than the other. Plus her make-up needs work, but in total, she's actually quite pretty. With my help, she could easily pass as my niece." Then realizing what she had just said...Sharon began to softly giggle. Brad unpacked his suitcase and displayed all the female clothes he had brought with him. When he saw the satisfied smile on her face he thought he might get away with not having to explain his crossdressing in Sandy's clothes, but that was not the case. Sharon, realizing the look of hope his eyes projected and what the look implied, dashed his hopes and demanded he continue his story. Detail after detail of this morning's snooping was admitted. At the last moment he decided to hide his discovery of the diary and the photo album. Maybe he could use them to bargain with. His silence about Aunt Sharon being a lesbian had to be worth something, he reasoned. Finishing his story, he asked, "What are you going to do about me, Auntie? Please keep my secret," he pleaded. "I need some time to think this through. Let me understand this, you would rather be a girl than a boy. It's obvious your adept at acting as a female and I don't suppose anything I do or say will change your desire to crossdress. Even if I expose your crossdressing to your mother it certainly won't solve anything. All it will do is make my sister's life more miserable because she'll have to tell your father and we both know what his reaction will be. I'm not sure that I can do that to her or you. Maybe you're right, maybe you should have been born a female. Be that as it may, the question still remains, 'What do I do about it and what do I tell your mother?'" Brad had a solution, but, wasn't quite sure if his Aunt was ready to hear it. Deciding to take a wait and see attitude, he shrugged his shoulders as his only response. After all, he still had the photo album as leverage. Aunt Sharon continued, "Right now, I'm going to let you stay dressed as a woman for the day. Obviously, we're not going shopping. If I'm going to allow you this gender switching you may not need more boy clothes and I'm not taking you shopping for female clothes, at least not just yet. Also, I'm not ready to be seen with you dressed as a girl. I will allow you to spend the entire day showing me how well you can pass. If I'm satisfied you're that 'good' maybe we can both have some fun with your desire to be a woman. It might be fun to have my niece visit me for the summer instead of my nephew. That doesn't mean I'm going to forget your snooping, or that you borrowed my girlfriend's clothes. But we'll discuss that later. Now, what is it... Lynn, let's go downstairs and have some lunch." Over lunch Sharon explained that the dentist was called to the emergency ward of the local hospital to assist the doctors. An accident victim had been brought in whose face had hit the windshield and who needed immediate dental attention. This caused the dentist to cancel all his office appointments. When Sharon was informed of these events by his nurse, she decided to return early and pick-up Brad. Through-out the meal, Sharon carefully observed Lynn's movements, when they went back to the den she told Brad she liked what she had seen so far. "I'm halfway to accepting you as Lynn. There are, of course, some needed improvements in your appearance. We'll work on those this afternoon, but before we get to that, we need to talk. Why don't you sit here on the couch, next to me." Lynn moved to join her Aunt on the couch. Placing her hands under her skirt she gracefully sat down. Crossing her knees and placing her hands in her lap, she turned towards her Aunt. It was obviously done to Sharon's satisfaction, since she smiled at Lynn, then said, "If I agree to your becoming Lynn on a full time basis, our relationship is going to change. First of all, you'll have to become my niece to everyone with whom we come in contact. You won't be able to switch back and forth between genders. That would be confusing to both of us and too dangerous! Since I haven't told anyone about your visit, I'll just change the story a bit. Therefore my niece instead of my nephew will be staying the summer. However, I'm going to expect a higher level of obedience from you. Some of the things I might have excused from my nephew, I won't from my niece. Brad, this is your big chance to take on the lifestyle of a young woman over an extended period of time. It's definitely your only chance to do so with the help I can offer you. I am going way out on a limb for you and I expect absolute compliance with my wishes. Any variance will be dealt with in a serious manner. That's not to say you'll be harmed, but you will be punished, like last night." Brad quickly responded, with a mischievous sparkle in his eye, "Auntie, help me to REALLY transform myself into a woman, make me your niece and I promise the only time I'll need a spanking is when I want to be placed over your knees." "Aha! So you enjoyed last night, I thought so! Well, since you are being so honest, I'll be just as honest. I enjoyed giving you that spanking. I guess you may get more spankings than I anticipated. Are there any other secrets you'd like to admit? If we're going to change our lifestyle we need to be perfectly open with each other. You go first and then I have something to tell you." Brad surmised he knew what his Aunt was alluding to...her secret life as a lesbian. He now had the perfect opening in which to admit what he knew about her sexual preferences. Because of what had already transpired, he had decided not to blackmail Aunt Sharon. Without further hesitation, he told her about finding the diary and the photo album. He told her he hadn't read the diary, but had seen the pictures. Watching the reaction on Sharon's face change from shock to smiling embarrassment was wonderful. As I've said, Sharon's initial reaction was one of shock. She had been about to admit her lesbian tendencies to Brad. She had realized that when Sandy showed up next week, their secret would have been revealed anyway. What shocked her was Brad seeing the pictures of their love- play together and the acts they had performed which obviously exposed their nakedness. Explaining to her nephew she was Bi-sexual was certainly different than letting him see her in the act of eating another woman's "pussy". Realizing there wasn't much he hadn't seen, she asked. "What do you think of me, are you disgusted?" "Oh no!" he stated. "I thought the pictures were beautiful. Beautiful and very, very sensual. It made me wish I was the lucky woman in bed with you. I think you're the sexiest woman alive. I would have given anything to join you in those scenes. Auntie, I think I better explain something. I'm not interested in males, even when I'm dressed as Lynn. I'm not gay in that sense. I want to be a woman with other women." Sharon said, "Brad, I think you better explain what you mean, I realize you have a crush on me, but I'm confused." "You wanted us to be honest with each other, well I can't be more honest than I'm being now. Even before I saw those pictures I fantasized about making love to you! You're the only woman I've dreamed about going to bed with, sometimes as a boy being seduced by you and other times as a young woman and your equal. I've pictured myself, hiding under your long skirts, totally hidden from view, as you carried on a conversation with another woman. What I would do to you would make your legs shake and your voice crack. Other times I saw myself sitting next to you, with your hand inside my blouse, teasing my tits, while your other hand teased circles upon my nyloned thigh. You would un- button your blouse and let me suck your breasts. There, I'm sorry if I've offended you, but I finally had to tell you how I really feel. I'm tired of hiding those feelings from you!" Sharon was momentarily taken by surprise. Her mind raced as Brad declared his love for her. The feelings Brad had for her were obviously stronger than she at first realized. Sharon was not one who squandered time when a quick decision was needed. Her decision made and without explaining her decision to Brad, she acted upon it. "Honey, let's take this discussion upstairs and get to work on improving your feminine appearance." The next few hours brought about a major change in young Brad's appearance. He was told to strip, whereupon his legs were shaved for the first time, his pubic hair was trimmed and shaped and the hair under his arms was also removed. Then Sharon inspected him for facial and chest hair. To Brad's delight, no beard plucking was necessary. He suffered through having his eyebrows formed and shaped and also his hairline was slightly contoured into a more feminine style. Through all this he remained nude. His hair, long for a boy, was still too short to shape into any feminine style. Now came the "dressing-up". Sharon had laughed uproariously when Brad had removed his nylon stuffed bra. Telling him to take a scented bath, she grabbed her car keys and purse and drove to the drugstore. Before she left she warned him against playing with himself. Within a half-hour she returned carrying a large paper shopping-bag holding her purchases. Entering the master bathroom she encountered Brad just after he had stepped out of the tub. Seeing him, a smile came to her lips and putting her hands together, she gave the youth an ovation. Brad stood before her with the bath towel wrapped around his chest and a second towel around his head in the form of a turban. The effect was one of a flat-chested girl. Seeing his features unencumbered by clothing and framed by the towels, she realized how easy this transformation would be. Dumping the contents on the bed she turned to her dresser. Searching through the drawers she selected articles of her own for him to wear. Handing him the selections Sharon coached him in getting dressed. When he went to roll both nylons onto his toes, she corrected him with a slap across his bare tush. "That's how teenage girls in a hurry get dressed. A woman takes her time and enjoys the sensual feel of the nylons on her toes, ankles, calfs and thighs. She never rushes getting dressed! Let whoever is waiting for her...wait a bit longer. Getting dressed-up, for a sensual woman, must always be erotic, or what's the sense of being female. Now do it right this time." Brad, following her direction, was amazed how much more he enjoyed the sensations. He realized it was partially due to taking his time, but also because his legs were now clean-shaven. Attaching the clips of the powder blue garterbelt to the nude colored nylons, he paused long enough to slid his hands over his hose covered legs. Telling Sharon that she was correct brought a smile to his Aunt's lips. Inserting his legs into the matching lacy panties, he "slinked" them up and over his thighs and "snuggled" them into place around his ass, again taking his time and enjoying the feel of the material as it enveloped his form. Tucking his penis back between his thighs was the only way for the panties to fit properly. This he accomplished with difficulty, since he was sporting a semi-hard erection. When he finally succeeded, Sharon came over and adjusted the fit. Handing Brad the bra that matched the panties and garterbelt, she watched him as he clipped it in front, twisted it around, inserted his arms and pulled it in place. As Brad bent over to pick up the extra nylons (to fill the cups), Sharon again slapped his now pantied ass. "That's not how a woman bends to pick something up. She either squats, remembering to always keep one leg slightly back of the other, knees close together, or she bends from the waist keeping her knees locked. You must always keep in mind, it's not the clothes that will give you away, it's acting or moving in an improper or un-lady-like manner. Here let me give you another example; Take a look at your nails." Brad did as instructed and again received a slap on his pantied ass. "See, that's what I mean, males curl their fingers into their palm to view their nails. Woman stretch their fingers and hands away from themselves, like this. We want to see the overview, the backs of our hands and the polish on our nails all at the same time. See the difference, good! Now, instead of balled up nylons, slip these into your bra. These are your new tits. The medical term is prosthetic breast sacks. I picked them up at the medical supply store next to Walgreen's. They are used by women who have had breast removal surgery. They'll give you the natural look, weight and feel of real breasts and will move with your body as you walk." As Brad went to insert one his Aunt began laughing. "Not that way, it's up-side-down, here let me help you." Brad stood still as his Aunt inserted and adjusted the gel-filled devices. Sharon cupped her hands and lightly bounced both sides of his form-filled bra, adjusting the straps until just the right tension and jiggle was achieved. Satisfied, she stepped back admiring the effect. Immediately, Brad felt the difference. There was an added weight pulling on the bra and the straps formed the slightest indentation at his bare shoulders. He brought his hands up under both cups and fondled each cup in turn. "I have tits!" he boldly announced. "Oh, this is definitely much better than the nylons. They really feel like they're a part of me!" As he turned he felt the momentary delay in their movement and the correcting sway after he stopped. Taking a few steps, he felt how they "jiggled" and bounced. "These are wonderful! So much more lifelike. Look they even have nipple marks you can see through my bra. Oh, thank you Auntie. This is wonderful!" "You're welcome, now let's work on your make-up." The next hour was spent trying different shades of base, mascara, lipstick and eye shadow. Sharon did all the work as Brad listened and watched attentively. When she was finished, what she had accomplished was a work of art! No longer was he just pretty, he was beautiful. Sharon's skills had enhanced his original, somewhat feminine facial features, to a new level. Looking at himself in the mirror he saw a younger version of his Aunt. It was now obvious they were related. Sharon, satisfied with the result of her handiwork, said, "When you learn to do as well by yourself, nobody will be able to discover your real gender just by your looks. I have another surprise for you, give me your hands." Extending his hands, Sharon began attaching the false fingernails she had purchased. After they were set, she filed them into shape, brushed them with several coats of red nailpolish which matched his lipstick. Leaving the room for a moment, she returned carrying a handful of assorted costume jewelry. These were tried until the effect she desired was accomplished. He now wore a thin gold chain hanging from his neck, with a Kremetz Rose resting just above the rise of his breasts. A pair of matching earrings, two cocktail rings and a thin gold watch completed the fashion statement. Stretching her hands out as she had been taught, Lynn marveled at how different they now looked. Training Brad how and where to apply perfume came next. This was followed by teaching him the different ways to step into a dress and also how to step into high heels. For the first time in eighteen months Brad realized he had been putting on his heels like a boy, with one ankle over his knee. The final step in his transformation was the wig. Sharon went to her closet and selected a light honey-brown, long tressed hairpiece with a flip. Placing it upon his head, she then brushed out the snarls. The finished effect was outstanding! Walking to a full-length mirror Brad stood there with the sweetest of smiles. Turning to his Aunt, with misty eyes, he ran to her open arms and expressed his gratitude. Sharon was just as pleased. When she had agreed to the transformation, she had done so with some misgivings. She no longer felt any doubts. Brad definitely looked better as her niece than as her nephew. Thinking aloud, she said, "I always wanted a daughter...now I have one in the form of a niece." The rest of the late afternoon was spent practicing feminine mannerisms. As Brad became more adept, Sharon decided to discuss how their new lifestyle would work. It was decided to pass Lynn off as an eighteen year old. The manner in which her Aunt had transformed him, helped Lynn to look older anyway. As the light began to fade, announcing evening, Aunt Sharon asked, "Would you like to go out to dinner and maybe a movie?" Lynn's response was immediate, "I would love to go out with you! Does that mean your comfortable being seen with me in public?" "Yes! I have no doubt you'll pass. I know a wonderful little Italian restaurant near the mall. They have the best pasta in town. After dinner we can see a movie if the timing is right or we can 'window shop' for a while. Let me freshen up a bit, first. My outfit is too casual if your going to go dressed like that. Why don't you join me in my room while I change? I think it's time you see what a real woman looks like!" Brad couldn't believe his ears. If what his Aunt was saying was true, he was going to see her naked! Quickly following, he entered Sharon's room. There she motioned him to take a seat on the bed. She began to strip. When she removed her bra, Brad gasped in astonishment, bringing another smile to the woman's lips. Wasting little time Sharon selected new lingerie, a different dress, a pair of heels, repaired her make-up, brushed her hair, added perfume, jewelry...all under Brad's attentive and never wavering view. Within forty minutes they were on their way. Lynn had been given a black shoulder bag, a lace trimmed hanky, tissues, a hair brush and make-up to be carried in the purse. Her Aunt also coached her as to the proper manner to carry a purse. When they got to the restaurant, they were informed there would be a forty-five minute wait for a table. Deciding to wait in the lounge, they left Sharon's name and proceeded into the bar. Others had had the same notion and there were no seats available. Before they could decide on a new course of action, they were offered places at a small table by two men. Lynn was reluctant, but was forced to follow her Aunt's lead, when she accepted their invitation. Sharon introduced Lynn and herself and the men did the same. They gave their names as Bob and Tony. They were in town for a convention, had been bored with the drunken antics of their fellow conventioneers and had set out on their own. A cabby had suggested the restaurant and here they were. They offered to buy the ladies a drink, which was accepted. It was obvious the guys were hoping the women would join them for the eveni

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This happened a long time ago. I was assistant manager in a fast food restaurant in rural Ohio; Sharon was just one of our hostesses and just of high school. I was maybe 28 years old. We were both unhappy. Our employees were all just kids. Some in high school, others in college, and a few were out of school, working class kids with no skills. Sharon had just started college, but went part time. Most of the kids knew her, having gone to school with her. She was a gawky kid with glasses and a...

Masturbation
2 years ago
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Showing Off Again with Sue and Sharon

A surprisingly hot May Friday in New England, Memorial Day weekend. Sharon had been coy about the purpose of the visit, but Sue felt that any visit to Sharon's was time well spent. A good friend with whom you could share your thoughts, commiserate, share and trust. After breakfast she showered, toweled off and dressed. Cutoffs, a cotton camisole and sandals. The ninety-minute drive to Sharon's went quickly; the holiday traffic wouldn't hit until afternoon, and when Sue pulled into...

3 years ago
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Robbies first time with his sister Sharon

I’ve wanted to fuck my sister since the first time I jerked off when I was twelve years old. I would peek through the door jamb at her and my mom when they’d get in or out of the shower. I would pretend to be asleep on the couch with my hard cock sticking through the fly of my boxers when my sister would come home from dates at night. I was obsessed! This is the retelling of the first time I finally got to fuck her. It was the summer of 2009. I had just turned 29, my sister, Sharon had just...

Incest
4 years ago
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Robbies first time with his sister Sharon

I’ve always wanted to fuck my sister. I would peek through the door jamb at her andmy mom when they’d get in or out of the shower. I would pretend to be asleep on the couch with my hard cock sticking through the fly of my boxers when my sister would come home from dates at night. I was obsessed! This is the story of the first time I finally got to fuck her. It was the summer of 2009. I had just turned 29, my sister, Sharon had just turned 32. I was dropping her off at her house and had no...

Incest
4 years ago
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My horny sister Sharon

I thought I would share my humble experience as well with you wonderful people. My name is RYAN. This story about me but about I one day found heaven on earth in my own house.my little sister, Sharon just turned 18.i need to mention here that at this age shes as hot as a full grown woman as she has that perfect body anyone would die for.i have been noticing sharon’s beauty for a long time now and whenever I had a chance, would try to feel it.one day our parents decided to spen some time with...

Incest
2 years ago
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With My Slutty School Teacher Sharon

Hi readers, this is Sarfaraz Khan back with another story. Hope you remember me. If you haven’t read , you are missing many things, kindly give a read. I’m a 23-year-old male from a South Indian city. I love sex, which is smooth and seductive, never forced. So coming straight to the story It is about my slutty elementary school teacher. Her name was Sharon. Let me describe her here. Back in school days, she was a darling of everyone’s eyes and a sure eye candy for all staff, including peons,...

3 years ago
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Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?This is a real life story of a crossdresser caught in the act!This happened around when I was 15 yrs. old.As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my...

4 years ago
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My first Forced Femme Crossdressing experience wit

Forced Femme CrossdressingForced Femme Crossdressing had never crossed my mind. Certainly not that day.  I had been lounging in my PJs one evening early last December. My fiancé Melissa was working 2nd shift rotation. When her best friend Dawn showed up at our front door. She invited herself in when I opened it. When Dawn and I are alone, she always teases me about my bisexual tendencies. It was my own fault for letting them slip one night when I had way too much to drink. Which Melissa had...

1 year ago
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Brenda and Sharon

My name is Brenda. I came to the university on my own. Parents gave me some money but I was working getting loans and grants for the rest. I had lived off campus with a dude who turned out to be a douce. He tried to put the moves on me and I wasn’t interested, for whatever reason. He just didn’t do anything for me. Anyway, I decided that day that I needed to move out and find a new room-mate. I couldn't afford a place by myself. But this time I was going to find a female room mate. So I checked...

Lesbian
3 years ago
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Like A Virus Shannon And Sharon

AUTHOR'S NOTE: This is part of a series of stories, all set in the same universe. Reading the story "Puzzles and Solutions" will make things in this story make a lot more sense. Andy Meeker pulled around and stopped in front of the grocery store to pick up the milk and bread and such that his wife had asked for when he had called. He stepped through the front door, and the first person he saw was Jason, a sixteen-year-old boxboy, on his way out the door, pushing a shopping cart full of...

2 years ago
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Sharon

Prologue I really love the taste of a man's cum. Really! The smooth feel of it on my tongue, the sloshing around of it in my mouth, the easy way it coats my throat on the way to my stomach. And yes, the awesome knowledge that my mouth, my tongue has given such pleasure to another human being. (I also love the taste of pussy; we'll talk about that later.) But after all these years, after all the gallons of sperm that I've ingested, deep down I know that those little soldiers swimming...

1 year ago
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Paul and Sharon

‘Are you fucking that little bitch?’ ‘Pardon me? Who? Of course not.’ ‘Are you sure?’ ‘I assume we’re talking about Sharon. Look, she’s your friend, you’re the one that suggested the two of us play tennis together on Saturday mornings since you don’t really enjoy the game. They live in our neighborhood and it’s a very small neighborhood. You’ve got to be kidding me.’ ‘I see the way you look at her.’ Said my wife of eight years. ‘Honey, she’s hard not to look at, particularly in those...

1 year ago
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SEX PARTYSHARON

The organised party was going really well and the Ladies that had chosen to breed had selected their stud for the evening. The Madam released the boys from their 2 weeks of chastity and allowed there weapons back into the public again!!! I was a little surprised that a pretty, tiny and slight girl with mousy hair called Sharon was standing nervously in the breeding Ladies line up? We spoke and she explained that she had had a couple of white lads, but said they were not up to much in bed and...

2 years ago
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SEX PARTYSHARON

The organised party was going really well and the Ladies that had chosen to breed had selected their stud for the evening. The Madam released the boys from their 2 weeks of chastity and allowed there weapons back into the public again!!!I was a little surprised that a pretty, tiny and slight girl with mousy hair called Sharon was standing nervously in the breeding Ladies line up?We spoke and she explained that she had had a couple of white lads, but said they were not up to much in bed and she...

2 years ago
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My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

3 years ago
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My Ex Girlfriend Sharon

Though I am 40 Yrs young, married to a beautiful woman, father of a son. I feel that I am not living my life as per my heart. It was late in the evening and suddenly there was a call on my cell. I couldn’t recognize the number and was in a hurry to leave the office. I picked the call nevertheless, curiously thinking about the caller.A sweet “Hello” and my brain went into a rewind looking for matches. The moment my brain flashed the matching face near my eyes, I slumped with astonishment and...

3 years ago
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Stoned Sharon

Stoned Sharon By Solon Plorry The man shouted at the attacker! He had beaten me so bloody and laid one last hard kick at my head before he went away to join his girlfriend, his soft shoes making a welcome squishy noise as he faded out. I lay in the fetal position, almost afraid to breathe. I had been beaten to within an inch of my life, I think, and all I could do was moan. My chest felt caved in, and pain flooded my senses. I wanted to die! A calloused hand was on my...

1 year ago
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My crossdressing fantasies Free Sex Stories and Adult Erotica Stories

I had an affinity towards women’s clothes and have a lot of crossdressing fantasies. The soft silks, shimmery fabrics and bold colours – I loved them all. But I was a boy and all my friends would laugh if ever a boy wore a pink shirt. And I loved hose colours. I wanted to raid my mom’s closet, wear her dresses, put on makeup and strut like the diva that I was. But I held this in me for many years, until one night I saw my parents. They had dressed up in costumes I believe. My mom was a...

Cross Dresser
2 years ago
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Sharon

This is a true story of how I met and had a hot sexual relationship with Sharon;First some prelude: I was stationed in Germany with the U.S.Army, I was assigned as the operations NCO for a Signal Company, My duties revolved around ensuring the Company was trained and ready for deployment if necessary, I also took over as the Company First Sergent when he was absent for extended periods of time, I was performing these duties when I met Sharon, She was a transfer from state side to our company,...

4 years ago
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Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

2 years ago
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A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

Humor
1 year ago
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Slave Sharon

 CHAP 1 Here I was, a sexually attractive female who had naively allowed herself to be striped of everything and was finding many reasons to feel ashamed of the loathsome things which I now did while groveling at the feet of another woman. My intrepid infatuation had come with a somewhat unpretentious and rather carefree understanding of how truly submissive I could be made to be. Our relationship started innocently enough, the very casual although sensual neck and shoulder massages...

4 years ago
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An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

Crossdressing
2 years ago
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First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

3 years ago
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First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

3 years ago
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Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

3 years ago
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Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

2 years ago
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Lover To My Widowed Aunt Pt 1 Alone With Aunty

Dear friends, I am writing a story about my past after a very long time. By the way, I am Rajesh (changed) aged 45 years and currently residing in Bangalore. Ladies, girls and unsatisfied married women can contact me on to talk about their sexual experiences. Maybe I can give some sex advice which I have learned from my past. This incident happened when I was studying Engineering and was around 19 years old. My dad asked me to go to Madras (now Chennai) to his sister’s house to give her...

Incest
2 years ago
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Lover To My Widowed Aunt Pt 2 Fingering Aunty

Dear friends, I am writing a story about my past after a very long time. By the way, I am Rajesh (changed) aged 45 years and currently residing in Bangalore. This incident happened when I was studying Engineering and was around 19 years old. My dad asked me to go to Madras (now Chennai) to his sister, Mandhira aunty’s house to give her company for a few days. Still blushing, Mandhira aunty turned to move away from me, but I just moved closer to her and held her hands and I could feel the heat...

Incest
3 years ago
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Caught Being Naughty by my Aunt

I enjoy being naked. When I'm alone that is. When my wife goes away for a few days, if the weather is nice, I spend most of my time nude. I water the garden, hang out in the house cooking and cleaning, and just generally hang out undressed. Recently when my wife was gone on a trip for a week, I was laying on the couch naked of course, watching a spanking video on the flat screen TV. I had my lap top connected to the internet and plugged into the TV. I was was enjoying the video and just sort...

2 years ago
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An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

Crossdressing
3 years ago
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Crossdressing Domina gets a new slave

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

Crossdressing
4 years ago
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Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

3 years ago
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The Seduction of Sharon

When I think back and recall all the trouble I went through to seduce and take Sharon, my neighbor Jerry’s wife, to bed, I shake my head and wonder how blind I was not to see the big picture. Not that I did not enjoy making love to Sharon. I still do, in spite of everything that happened since that first time and the whole scene, blurred in the beginning, came into focus with a bang, literally, one sunny afternoon. But I must first write about the seduction, of which I am quite proud of before...

1 year ago
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Kim or Sharon

It is Saturday afternoon and you are just finishing your neighbor's lawn. My dad says since I am 18 that I have to pull my own weight so I mow the lawn of my 40 year old neighbor Sharon. Sharon is of great interest to me becuas she is about 5'10, about 135lbs, 32c breasts, a perfectly slim and trim body, with brunette hair. But even better is her daughter Kim, the object of most of my fantasies. Kim is 20 years old, but decided to put off college for a few years and live at home with a basic...

4 years ago
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THE MIND OF DIRTY SHARON

THE STORY OF SHARON CANE.................. I AM SHARON CANE, A 18YR OLD TRANSVESTITE SCHOOLGIRL WHO DUE TO MY BAD BEHAVIOUR HAVE BEEN SENT TO MANY REFORM SCHOOLS, OF WHICH EVEN WITH FREQUENT FIRM DISCIPLINE HAVE BEEN EXPELLED FROM MOST OF THEM FOR MY DIRTY WANKING HABIT. MOST OF THE SCHOOLS I ATTENDED WERE BOARDING SCHOOLS WHERE I MET OTHER TRANSVESTITE GIRLS & WAS INTRODUCED TO FULL TRANSVESTITE SEX BY OLDER GIRSLS. WHAT USED TO MAKE ME WANK SO MUCH?... JUST THE SHEER JOY OF BEING DRESSED...

2 years ago
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Letter to Mistress Sharon

Mistress Sharon Director Christian Feminization Academy [address redacted] [address redacted] [address redacted] Dear Mistress Sharon, My name is not important, but I want only to be Stephie. Please consider me for a position in your next intake into the Christian Feminization Academy. I have not been a good Christian up until now, in fact I have really not been a Christian at all, but I promise you that I will be the very best Christian woman that I can be if you will show...

1 year ago
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The Late Crossdressing Husband

THE LATE CROSSDRESSING HUSBAND by enduringshades Edith and I had known each other since we were teenagers. We went shopping together and often met for lunch or coffee. Friday night used to be our Girls Night Out when we dressed to the nines and headed for our favourite bar. Then we got married (not to each other!) and stopped going out together. Edith was still a party girl, but I stayed at home with my wife, Betty. I never told Betty that I was a crossdresser. I missed being...

4 years ago
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CAUGHT jerking OFF by my AUNT PEGGY

CAUGHT jerking OFF by my AUNT PEGGYI was about 13 years old and as all you guys know, at that age, all you think about is girls, football and getting off! I would spend lots of time at my aunt and uncles place on the lake in the summer and when you see young girls running around in bikini's, etc. You HAVE to have some relief!Being that age, you can't really just walk up to a highschool girl who's HOT and ask her to fuck you so you do the next best thing..JERK OFF!!I had a secret hiding place at...

3 years ago
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Stefanies Crossdressing Memoirs Vol 6

I've decided to switch the category for these over from blog post to sex story, as at this point in my adventures as a gay crossdresser, I had pretty much hit my stride dressing up and finding men and other crossdressers online to have sex with. So I guess you could say my posts moving forward will be a little more "action" oriented. Plus at this point it is hard to remember all of my experiences chronologically, and for the most part that's really kind of irrelevant. If any of you are...

4 years ago
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Lover To My Widowed Aunt Pt 3 Seducing Aunty

Dear friends, I am writing a story about my past after a very long time. By the way, I am Rajesh (changed) aged 45 years and currently residing in Bangalore. This is the next part of my story. I woke very late in the morning and came out from the bedroom stark naked not bothering to dress up as I knew we are alone in the house right now. I saw Mandhira aunty in the kitchen fresh from her bath, wearing a white kurta and white leggings. I went behind her without her noticing me and pressed my...

Incest
2 years ago
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Crossdressing Hooker and the Creampie

I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already. I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm. I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair...

3 years ago
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An Introduction to Crossdressing Pt 5

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...

Crossdressing
3 years ago
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Girlfriend Catches Me Crossdressing

At this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...

4 years ago
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Duped Into Being a Crossdressing Bull Part I

During my second year in college I was in between girlfriends and at the time I was greatly indulging in my crossdressing fantasies. I spent a lot of time in lingerie sections of stores buying bargain panties and bras since that is all that I could afford. The pickings were fairly slim for a big guy, so I developed a love of granny panties because those are so easy to find at a store like Walmart or Target. Craig's List and similar websites did not yet exist at this time (including Fet-Life)...

3 years ago
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JOANNE SLAM A LIFETIME OF CROSSDRESSINGhellipAlmost

JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...

3 years ago
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First crossdressing experience 3 cocks in1 hr pa

I started with crossdressing a few month ago, first just panties or strings when i had a wank over videos and pics of other crossdresser getting taken or dominant trannies and women humping devot men.By now i wear black stockings and suspender belt, a white lace string, black shiny mini skirt, white blouse, 4" black heels and a blonde wig.I also had an extreme urge in me to feel a real cock in my arse, to satisfy these needs i began to visit adult cinemas in my area, first just with stockings...

3 years ago
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The story of how i began crossdressing Part 13

Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She told me she’s looking for a slave to entertain “them”Thought it was a spelling mistake (since it was german its not really much of a difference)So i agreed...

2 years ago
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first time web hook up crossdressing dominatrix

crossdressing has always been my secret pleasure I even had a cache of out fits make up wigs and heels. it started when I was younger but evolved as I got older, now as I got older ive refined my skills and abilities and can pass as a girl when dressed. I had fooled around with guys before but I had never dressed for one only indulging in self pleasure with toys and my fingers. when I got off work on friday I was excited for the up coming three day weekend going home to get dressed up maybe go...

3 years ago
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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be therei did think it would be nice to have it up here as well though :)Entry #1:I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :PI decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there) She...

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