I Want To Be A Glamorous Lady free porn video

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I Want To Be A Glamorous Lady By: Darlene LeQueene Written: 3/3/2010 "I'm done planting the flowers Mrs. Grant," I said. "Justin honey, I swear I have no idea why you keep coming over to do chores around here." "I am rich you know just like your Mother, I do have a gardener." "There's no need for you to do these things." "Not that I mind paying you, but you certainly can't need the money either." "I just like coming over here Mrs. Grant." She appraised him slowly now, was this a little slip, or was she just imagining things? Was he actually saying he was attracted to her? No that was silly, he was only 14 and she was 48, but his constant daily visits she wrote off to lonesomeness. His Mother was a divorcee jet-setter and in spite of his age she left him home alone often with a servant around. So he came over after school doing small chores for her. Recently his visits had extended to the weekends also. "Don't you have anything better to do darling, friends or whatever." He shyly hung his head and said, "They don't like me at school and I really don't have any close friends." "Why is that dear?" He hesitated and then decided she was nice and would understand. "They call me a sissy and a fairy and they won't talk to me other than to beat me up." "Oh dear, I see." "Well that's a sad explanation dear, but I understand, boys can sometimes be very mean." "Yea, I hate going there, I only do it because I have to." "But why come here darling?" Again he hesitated but decided to press forward any way certainly she wasn't going to beat him up and she was reacting nicely. "Well you're very nice to me and you're very beautiful too." "Beautiful?" "Darling how very sweet of you to say that but I'm just and old divorcee not unlike your Mother." "I'm surprised you think I'm beautiful." "Yes, at least I think you are," I replied. "Now she thought she really understood, he truly was a sissy he just didn't know it yet. But there were many kinds of sissies, she'd have to feel him out to see where his head was at. "Come darling Justin, let's get something to drink and make ourselves comfortable in the den in the nice air conditioning it's far too hot outside. Once he was settled on the sofa with his Coke and ice she slowly started to question him. "Darling if I ask you some questions will you tell me the absolute truth?" "Sure," he replied. "No I mean it darling it must be the absolute truth, pulling no punches, good or bad." "You must say what's truly in your mind alright?" "All right, sure I trust you Mrs. Grant." "Alright darling here we go, no cheating now." "Why do you think I'm beautiful Justin?" "Well you know, all the lady things, your makeup, perfume, clothes, everything, your just very ladylike and pretty." "I see, so you like my makeup, hairdos and clothes." "Sure they're pretty." "But surely there are girls at school that are pretty too." "No they're just as nasty as the boys, sometimes even worse." "And they look nothing like you." "Well I am quite a bit older that's why sweetie." "Well if that's the case then I think I prefer older." "Darling I hate to tell you this, but we are good friends." "Well, you really are a sissy." "No," he quickly replied. "Yes, you are darling, now when I say it, it's not like the boys at school." "I'm just telling you that you like certain girlish feminine things." "Which is perfectly all right with me." Well at least she wasn't yelling or carrying on like most adults, we was very calm and still smiling brightly so he decided to go alone with her. "Suppose what you said is true, would you still like me and want me to come over?" "Of course I would darling, in fact I'd probably like you even more." "Really?" "Yes, I believe I would." "Can I ask you some specific questions darling, promise to tell the truth?" "Yes I promise." "Well I do wear a lot of makeup, trying to hide my age." "Do you like my makeup?" "Yes I do Mrs. Grant, it makes you look, well very sexy and glamorous like a movie star or actress." "And you like my bouffant hairdos?" "Yes I do they're very beautiful." Well it was very clear now she had a full blown sissy on her hands, there was no denying it any longer, he had every sign. "Tell me darling, the truth now, have you ever wished you liked like me?" "No," he said much to quickly trying to hide it. "Darling I thought we agree to be honest with one another?" "Well, I mean, OK, yes the thought has passed my mind a time or two." She smiled just she thought. "Tell me sweetie, when you picture this in your mind do you look exactly like me or just like a young girl?" "Well, I sort of picture myself just like you." Well there you have it then, I understand perfectly." "I could of course make you look like me, if you wanted but you would have to keep it to yourself completely, never tell anyone." "Oh Mrs. Grant, be serious, I mean I fantasize about it but how could I ever actually look like you?" "You're a beautiful woman and I'm just a kid." "Well darling the things that 'Make' me a beautiful woman are all superficial." "Makeup, dresses, nylons, bras, high heels, etc. are all just things you wear." "Anyone could wear them if they wanted." "And you'd be surprised how much makeup can change the way you look." "Are you saying you'd actually do this," I asked? "Yes, if you wanted me to darling." "Only two rules, you never tell anyone else, ever and there are no half way measures you either want to look like me or you don't." "This is not something you just play around with." "I don't want you backing out if you think it's not going exactly the way you planned." "And you must obey me, at all times and learn from what I tell you." "I'm an adult and I know about many more things about this than you can possibly imagine." "Do you agree." "All right, I agree, and you won't tell anyone either?" "No darling this will be our little secret." "Your Mother is still away?" "Yes she'll be gone another two weeks I think, the chauffeur takes me anywhere I want to go if I need to go somewhere, and the maid cleans the house." "My Mother left me plenty of money, and I have a credit card to use too." "Well give the chauffeur the weekend off and tell him you won't be going anywhere this weekend." "The maid can stay at your house as long as she knows your spending the weekend with me." "So no problem there." "Saturday afternoon we'll do our thing darling." "Couldn't we do something tonight?" "No sweetie, I have to shop for some special things I'm going to need for you." "Tomorrow will be soon enough." "Go home now, and dream lovely sissy thoughts and tomorrow at this time you will look like me, I promise." She purchased all the things she felt she might need to feminize this young boy and turn him into a truer homosexual sissy faggot. He seemed to want it very badly and she was going to accommodate him. Of course she herself would have to look intensely wicked the next day when he showed up because she had to set a good example for him. The next day he arrived right on time and when she opened the door he nearly passed out in awe. She was dressed in a black chiffon blouse that showed her ample bosom encased in a black bullet brad underneath. Her skirt was skin-tight and also back, a hobble skirt although Justin didn't know that it was called that he just knew it looked fabulous on her and sexy as hell. Her makeup was the heaviest he'd ever seen. She had big long thick false eyelashes on and tons of dark eye makeup, crimson red lipstick and long red scarlet nails. It was the most stunning display of glamorous femininity he's ever seen or hoped to see. "Up to the bedroom with you sissy boy it's time to be feminized." He followed her to the bedroom and was ordered to remove all his clothes, everything. Fortunately being so young he had no hair, but she shaved his pubic area and plucked his thin brows anyway. The rest of his minimal brows she'd cover with foundation later. "Well darling let's begin, first off your clothes if your going to be a lady and not a boy we need a new name for you." "I've decided on Jessica." He made no reply just nodded his head still in awe of how sexy she looked. "Next I think calling me Mrs. Grant is a little formal for the intimate things we're doing here, so why don't you just think of me as 'Mommy' and call me that for our little game, alright?" "Yes alright," he replied, then added hesitantly, "Mommy." Do you know what this is Jessica," she held out a waist nipper type corset? "A girdle for a woman?" "Well actually it called a corset darling, this one is it black with red trim." "Do you know the purpose of this lady's garment?" "I think to make your waist look smaller." "Exactly dear, and while this might be a little uncomfortable for a young inexperienced boy it's necessary to get you looking like me." She began lacing him into the corset. She didn't want to scare him off the first time, but she managed to take him down 4" inches before he was whining about it crushing him. Next she added a black bra with 44DD breast forms that she's purchased yesterday at great expense. These were not the cheap kind but very expensive and weighed to simulate breasts of this size. They felt so heavy on his chest never having felt this feeling before, but he loved the sensation of wearing a bra. Next she produced sheer black nylons and slid them up his smooth young hairless legs. He loved the sensational feel of the smooth sheer nylon caressing his skin. He was beginning to like this process a lot even if she did call him a sissy. "Now we have something completely special for a girl like you darling, they're called sissy display panties." The sexiest lace and bows in black and red just like your corset and bra because women are always color coordinated darling." These are very special panties made just for sissies like you." She held them up and showed him the little hole in the front of the panties for his penis to fit through. She slid them up his hips and up to his waist pulling his hard erect penis through the little opening. It now stuck out dramatically through the ruffled lacy hole on display. She was as excited as he was at this sight. "Now you are beginning to look like a proper sissy." "Please Mrs. Grant, ah, Mommy do you have to call a sissy, it sounds so homosexual." Yes darling we do have to call you a sissy because that's what you are." "And yes it is very homosexual, because that's what you are too." "No Mommy, I swear I never did anything homosexual before." She smiled that wicked evil smile and in her current makeup and clothes that look was downright scary. "Not yet darling, but you will, oh yes you will, many, many homosexual things." He trembled at the sight of her, but dared not answer back. Basically she was in control now and he'd asked for this hadn't he? Besides he certainly couldn't leave dressed like this and his other clothes seemed to have magically disappeared. "Come along little sissy boy, it's time for lots of feminine makeup." To his surprise she grabbed him by his hard cock with her long red nails and lead him over to the lighted makeup table. "Just the brief period of her red nails wrapped around his penis made him even harder if that was possible. The thrill was intense and he'd do anything to feel it again. "Well darling first of all to look older your going to need lady's foundation makeup, I'd say several layers to give you a very made up look and hide your youth." She started applying layer after layer of liquid foundation makeup to his face. She paused in between each layer allowing it to dry before redoing his face again. After several layers she powdered everything with a big fluffy brush. He loved the feel of that brush so soft and the powder smelled so good. She noticed him enjoying the smell of the powder. "Yes darling, you love the smell of lady's powder don't you?" She placed a big helping on the brush and then held it under his nose. "Yes my little sissy faggot breath in that lovely feminine smell." She touched the tip of the brush to his nostrils. He froze, trying not to breath it in. "I said, breath it in you little sissy, or I will punish you right here and now." Let with no choice, he breathed in the lady's powder and it permeated his senses. He was intoxicating, it seemed to capture his mind in its grasp. "Yes lovely is it precious the smell of a lady wearing makeup darling." With his small plucked eyebrows now covered by several layers of foundation she was free to pencil in his new eyebrows. Black tapered and much higher and severely arched like a very sexy and glamorous older woman. She took her time making them perfect because the new eyebrows would be the most expressive and erotically feminine portion of his new older woman look. He tried to see what she had done it felt so strange, but she lightly slapped his face. "No looking darling until Mommy is all done and you see the new you." Now she started on the eyeshadows. First a very dark gray almost black, then lavender above then and finally white shadow underneath his new ultra feminine eyebrows. She worked hard blending them and shaping them to be perfectly made up. "Now one of the most feminine things of all darling." "I bought a dozen pair yesterday just for you." She produced a pair of very long thick lady's false eyelashes. She placed some white type glue on them and then carefully glued them into place on his lids. When she was finally satisfied that the glue had dried so told him to open his eyes. The weight of them felt so heavy, and even stranger for the first time in his life he could see his own eyelashes because they were so long and thick. He immediately liked the feel and weight of them. They made him feel so feminine and girlish. She only paused long enough to make sure they were in place and tightly secured before moving on to the black liquid eyeliner. His eyes were painted and thoroughly outlined in deep black. Such a sexy little sissy whore he made now, a lovely painted lady. She was so hot she wanted to play with her pussy but she dare not, not yet anyway. Bright red blusher was added to his cheeks and finally the most feminine of all things was coming. "Time for Mommy to put some very ladylike lipstick on you darling." "But first let's enlarge those luscious girlie lips with some lipliner making them bigger." She outlined his lips with some kind of pencil that looked like it was a dark purple almost black. He could tell from where she was drawing that his lips would be bigger, much bigger than his own true lips. "Now for your first lady's lipstick sweetie." "Get used to it because you're going to be wearing it a lot of the time in the future." She applied several coating of the deep crimson red lipstick to his lips until she was satisfied and then she surveyed her work. He was a true painted slut now, and it excited her, and better yet she knew it excited him too. She sprayed him all over with her Chanel No. 5 perfume until he was enveloped in a cloud of sweet feminine smells. "This is too good to pass up darling, let Mommy get some pictures of you." She added huge massive dangling rhinestone earrings to his eyes but reminded him not to look in the mirror yet. She produced a Nikon digital camera and began to take pictures of his made up face. He looked so bizarre with his short boyish hair and that heavily made up face and those big earrings. God he looked so sexy and wicked like that, but not half as wicked as she felt doing it to him. She was really getting off on this. She took dozens of pictures on his face from every angle to make sure she showed every detail and those incredible lashes. Then she took some more pictures at a longer length showing his corset, bra, nylons and of course those sexy sissy panties with his penis sticking out. Even like this it was hard to tell how young he was anymore. He looked like a boy all made up all right, but you could no longer know he was only a 14 years old boy. "Well enough of that you can't hang around in your bra and corset all day." "Let's get you dressed like a lady now." The sheer dark violet nylon blouse she placed him in did nothing to hide his black bra underneath, but God did it feel wonderful sliding over his smooth young body. He felt glorious wearing it. A skin-tight black leather mid-calf skirt followed very, very tight and it pressing his sissy cock against the slippery satin lining of the skirt creating a little bulge in the front. He of course was too young to understand the sexual significance of this, but she certainly did and was excited anew. She added a very wide black Patten leather belt around his waist pulling him in more tightly even then the corset. He was so concerned with the tightness that he never even noticed the big rhinestone buckle in the front that secured the belt around his now tiny waist. She led him back to the makeup table where she planned to add the final feminizing things. Next up was long red nails glued to his fingers. These nails were already painted a deep red so she simply glued the glamour nails onto his fingers. Now he had 2" inch long red nails, and of course he complained it was difficult to touch anything and they were hard to get used to. She reminded him this was how and older woman looked and to stop complaining this is what he wanted. Now for his crowning glory, the wig she had purchased. It was a very light blonde, but not quite platinum blonde. It was of course immense. It was actually two wigs together. The fitted wig was a big teased bouffant, and the wiglet that sat on top of it was lots of banana curls in the same blonde color so it look like all one. It was a massive ultra feminine updo that any drag queen would approve of. He looked sensational in it and she felt rushed now to finish him off. She added several big jangly bracelets to each wrist and a huge massive rhinestone necklace around his waist. She even added a shiny rhinestone ankle bracelet around his foot. She added 5" spike high heel pumps to his feet and strapped them on. She wished she could use 6" inch spikes, but she knew he's never be able to stand in them yet. So while she was disappointed she did have to face reality. No doubt even these combined with the tight leather hobble skirt would cause him enough problems. She helped him up and led the wobbling boy over to the full-length mirror. "Meet the new lady in town darling, Mrs. Jessica Grant." "Now just like me, Mrs. Veronica Grant." She wrapped a white ermine wrap around his shoulder and stepped back to show him the lady he'd become. It was incredible she'd actually done it, he looked like a 40 + woman, a very glamorous and sexy woman at that. The makeup was stunningly beautiful and he felt so glamorous and sexy wearing it. The jewelry was dazzling and very ultra feminine. The earrings were beginning to hurt his ears a little but he really didn't care about that anymore. "Do you like darling?" "Oh God, yes, it's incredible, I look just like a sexy woman, I never believed I could, I thought I'd look silly." "Nonsense darling, you're gorgeous and I know some homosexual men that would go gaga over you sweetie." There was that homosexual reference again he thought. But truly he was dressed like a woman now, and all made up too, perhaps she was right because the thought of some man fawning all over him made his cock bulge out even more. He wanted to look in the mirror to check if the bulge was visible and that's when he actually looked at his wide patton leather belt in the mirror. "Oh My God," he said. She laughed, "Yes darling I see you've finally noticed the belt." "It says 'Slut' spelled out in diamonds," he said. "Yes Jessica, well actually rhinestones darling, but yes it proclaims you to be a total slut." "Do you like it?" "Yes Mommy, I do." "You can't see your ankle bracelet because of your skirt and the high heels but that also says 'Cunt' in rhinestones too darling." "No, no, don't try to raise your foot honey, in those high heels you'll fall over." "Are you pleased with my work?" "Oh yes Mommy, I look wonderful and I feel so sexy, it's divine." She took hundreds of pictures of him posed and posing in various feminine ways and he was having a ball, he loved being a lady and acting like a super model, and she loved watching him. "Well now darling, I know being so young you haven't given much thought to this, but now that you've achieved your goal of looking like a lady have you given any thought to what you like to do with the cloned Mrs. Grant." Actually this surprised him, she was right, he'd never given it any thought, other than he wished he looked like her and he'd certainly like to kiss her and maybe feel her large breasts. He giggled mentally at the thought because now she could feel his too. "Well do you trust me darling, I mean will you obey me and trust me when I tell you, you will learn to love this?" "Yes, Mommy, I do trust you completely." "Even if it hurts just a wee bit?" "Yes, I guess so." "No, darling, no guess, you must say you trust me completely and you will obey me no matter what." "All right, I will obey you." "Good then let me make a phone call and I'll be right back." She helped him wobble over to a chair to sit. "Just relax darling, I'll only be a minute." "Look at your pretty makeup, hairdo and jewelry in the mirror while I'm gone and perhaps practice a little in those lady's high heels dear, but be careful, being a lady isn't always easy." She went off to make her call. Actually she'd planned this all alone, but she wasn't sure the boy would go through with it so she'd held off the call until he was actually fully dressed. "Yes Ron, she's ready and waiting come on over, just remember our agreement." "You obey me completely, and you leave when I tell you to leave and I guarantee you a real good time. Her friend Ron was homosexual and had a thing for drag queens too. He was perfect for the job and he'd agreed to do as he was told for a great blowjob from a fabulous queen in return. Of course he had no idea that the blowjob he'd be getting was from a 14 year old boy, he was told it was some regular queen that Mrs. Grant knew. She returned to the bedroom to find the little minx actually practicing walking in the high heels. Well he certainly was serious about wanting to be a woman. As she silently watched she realized he was actually getting better already. He really was trying hard in spite of the hobble skirt and the heels he was developing a good wiggle and swish to his walk. OK, he was a little shaky at times, but he was getting better already. "Enjoying yourself Mrs. Grant," she laughed as she entered. "I was just practicing as you asked Mommy, it's very hard isn't it?" "Yes dear, it is, it takes a while to walk how to walk in high heels properly." "Anyway, since you're all dressed up and made up darling, I thought there was no sense wasting it." "I've got a hot guy on the way over who would love for you to be his girl and suck his cock." "A guy, suck his cock, oh no please Mommy." "Now dear I thought we agreed you are homosexual and you are a sissy." "That's what sexy little sissy faggots do darling." "You said you would obey me and trust me." He felt trapped completely but he felt if he didn't do as she told him then she'd never dress him up again like this and that was a thought he couldn't stand. "I'm sorry Mommy, yes I did agree, and I'll so what you tell me." "Good, now she need to make one addition before your hot stud gets here for his blowjob." She helped him out of the belt and skirt and produced a shiny pink butt plug. "Bend over little princess, time for you to take some cock like a woman too." "We must begin your training as a glamorous slut just like you belt says." He made no further complaint, he trusted her and relaxed as she told him and with a little effort the plug slide into his virgin ass. "Just like a woman now darling with a cock inside you." She helped him back on with the skirt and belt because with his new long red nails he was all thumbs. When Ron arrived he was stunned by the physical beauty on this new queen. "And your name is darling?" Veronica interrupted, "Let's just call her Mrs. Jessica Grant darling, and say we're sort of sisters." "Ah, another Mrs. Grant, well Mrs. Grant, your as beautiful as sexy as the original." He kissed the back of her jeweled hand when she held out a nice limp wrist displaying her long red nails. "Thank you Ron," he replied. Sensing no resistance he pulled her into his embrace and held her a second and then kissed her. Oh, the feeling of kissing while wearing lipstick was wonderful and no longer was he teased or laughed at by silly little boys. Now he was desired by real men who lusted after him. He liked this role much better. "Caress his crotch right through his pants Jessica, see if he's excited to see you." Jessica did as instructed and caressed the front of Ron's pants with her long red nails and jeweled fingers and quickly discovered that Ron did indeed have a rock hard cock under there. "I think he likes you darling," Veronica giggled. "Ron she's ready for you, take off your clothes and show her what you have for her," she said. Ron needed no second invitation he quickly removed all his clothes. "Her too," Ron said, "I want to see her in all her glory, because it's hard to believe that a woman so beautiful is actually a man." "Are you sure that's what you want Ron?" "Oh yes Veronica I do," he replied. She helped Jessica out of her skirt once again and when Ron saw the cute sissy cock sticking out of the ruffled lacy hole in her fancy panties his cock started to throb. "Kneel and kiss his cock Jessica," Veronica instructed. Jessica now free of the confining skirt dropped to her knees the hard male cock only and inch or two from her mouth. "Hold it with your hand darling and kiss it." Jessica was a little hesitant but obeyed and grasped Ron's hard male cock and kissed it leaving a lipstick mark on his cockhead. "Go ahead girl you know what you have to do." With a whimper and a small sigh Jessica slide the lovely male cock into her waiting lipsticked mouth. It wasn't bad she though, very smooth and warm, and the lipstick made it feel so good so she started to suck in earnest now. It didn't take more than 5 minutes. The sight of beautiful Jessica's made up face with those long lowered false eyelashes and those red lips and long red nails soon had Jessica swallowing her first load of male sperm. She moved her head to pull back but Veronica was there to hold her head in place. Well her neck any way with her immense hairdo there was no place to really grab her head. "Well, well what a great job Jessica." "Did I not promise you a great blowjob from a beautiful queen?" "Oh indeed it was fabulous," Ron replied. "What club does she work at, I'd like to see her show sometime," Ron asked? "Perhaps we'll talk of that later Ron, but per our agreement, you've had you fun and now it's time for a little girl talk." "By the way Ron just between us," she asked, "How old do you think Jessica is?" "Oh I hate to guess women's ages," he said, "They get very mad if you guess wrong. "No darling it's all right go ahead and guess." "Well maybe 35 or 40," he said. She smiled, "Yes close darling, all right run along now." She showed Ron to the door and then returned to the bedroom. As soon as she shut it they both broke into laughter. Jessica was the first to speak, "35 or 40, close, oh my God I really had him convinced I was an older woman." "Yes you did darling, I told you with the proper makeup and hairstyle and clothes you'd look just like me." "However it would not be wise to ever let Ron know your true age dear." "He thinks you're a new local drag queen at one of the female impersonator club, let him keep thinking that." "Oh yes Mommy, I understand." "Well now darling, Ron has gotten his jollies for the day and it's just us girls now." "I'll just bet somewhere in there you've dreamed of me doing the same thing to you that you just did to Ron sweetie, haven't you?" "I never dreamed I could be that lucky Mommy, but now that you mention it yes, I'd certainly like that very much." "Well sweetie, I will give you your fantasy, but Mommy first dear." "In order for you to be a fully sissy you have to be fucked like a girl, and that's Mommy's job tonight." "If you submit to me darling then I promise you the prize will be yours." "Yes Mommy, I trust you in everything, you made me feel wonderful so far, I even enjoyed sucking Ron's cock." "So I guess I am a homosexual now and I might as will finish it off." "Yes darling, exactly, I'll be right back darling." She disappearing into the bathroom for about 5 minutes and Jessica was left with instructions to repair his makeup and redo his lipstick as best he could. Like all these other feminine things he adored he took these instructions seriously and tried very hard to do a good job on powdering his face again and redoing his lipstick. When Veronica returned from the bathroom she looked more wicked and evil then ever because now protruding from her crotch was a life like looking cock, which she called as woman's strap-on cock. "It's time for Mommy to have her pleasure darling." Jessica was bent over a chair and her butt plug removed. "And let's spice it up a little darling, Mommy loves a simpering, whimpering little sissy." Veronica gave her a pink nylon scarf to hold in her right hand and showed her how to hold it daintily between her long red nails. "Now darling, Mommy wants you to wave your scarf daintily up and down from a nice limp wrist displaying your long red nails and your lovely jeweled fingers." "I want you to whimper and squeal like a little sissy girl for Mommy and show me what a homosexual faggot you are." "You may sob and squeal all you like, but no crying sweetie we don't want to spoil your makeup." "Are you ready to become a real woman and get fucked?" "Yes Mommy, I love you." Veronica lubricated the strap-on and slowly eased it into Jessica ass. The butt plug had served to stretch her out a little bit so it actually went in quite easily. Veronica started to fuck her little sissy virgin in the ass now. Just like a girl now Jessica played her part very well for one so young and inexperienced. She whimpered and squealed in a high pitch girlish voice and daintily waved her pink nylon scarf up and down careful to keep her wrist limp and her nails extended. "Oh Mommy, Oh Mommy. I'm a woman now, please fuck me Mommy." Veronica was careful not to go too far with her, after all it was her first time. After they both recovered from all the physical activity Veronica said, "Well you've been a lovely sissy lover for me darling so I guess it's time for you to finally received your pleasure." Veronica redid her lipstick and then it was her turn to drop to her knees and suck Jessica's cute sissy cock. Unfortunately for poor Jessica it was all over in less than 30 seconds. The makeup, clothes, sex and all the other activities had taken their toll and poor Jessica was spurting as quickly as possible. It was so intense she almost fainted, but when she'd recovered she seemed disappointed that it was over so soon. "Don't worry darling, it was your first time, next time we'll do things to make you hold out longer." "I presume you enjoyed yourself and you'd like there to be a next time dear?" "Oh Lord yes Mommy," I quickly replied. "Well then you keep all of this to yourself, just you and me sweetheart and no one else and Mommy will teach you everything." "Shall we say next Saturday at the same time darling?" The End

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My sexual adventures with the five sisters living next door to Gloria and her sister Veronica seemed to create a magnet for Gloria to sample my big boy in various positions and with astonishing results we had never quite achieved before. I had started to think that my inability to foster a satisfactory orgasm in Gloria’s glorious tubes was entirely my fault due to some genetic problem or mental shortcoming in the consummation process. It was quite a shock for me to see her writhing in...

1 year ago
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Gladys

Farber, Underwood, Carruthers, Kinshaw, Young, Oswald, Updike is its city's first openly transgendered firm. Follow the lives of its partners, associates, staff and clients. Today we learn the history of one of its members. GLADYS By Eugene Webber "Have you called the agency, Heloise?" John Farber asked his office manager. Heloise Farber, John's sister, older by three years, was taking a week off to visit their parents. Their father had retired eight months earlier and...

1 year ago
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Hello LadyBoy

How many of you get off to fucking ladyboys? Well, if you know what I’m talking about, then you know precisely the kind of sexy people I’m referring to. But for those whose brains are melting at the term of ladyboys, let’s keep it simple for them. A ladyboy is an Asian transsexual. But then again, if you didn’t know that, you probably are not into this kind of porn in the first place!On the other hand, if you are or are curious, allow me to invite you to Hello Ladyboy. This series has been a...

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3 years ago
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American Ladyboy

American Ladyboy By Cassandra Morgan No matter where in the world you are, no matter languages are being spoken around you, calculus is boring, it seems they teach the subject so people will know how to torture spies. And so, half a globe away, Benjy Hawkins sat in his math class with his head resting on his arms, which were folded over his desk. The teacher droned on, his lilting accent punctuating his speech. The subject, and the speech, was more than Benjy could bear on a...

3 years ago
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JuniorChapter 18 Gladys

Attending Greg and Trisha's wedding was an obligation that could have been avoided; I wouldn't have been missed. On the way back to school, I reflected. This was a good time to make some decisions. Why had I pussyfooted around and let Charlie take advantage of me? I told myself it was because of his mother. She had asked me to look out for him. But really, I knew in my heart that I was afraid of losing my only male friend. I didn't correspond with anyone from C.M.A. and doubted they even...

1 year ago
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Fun With Mom And Landlady

Ishwar Lal had left his wife, Urmila in charge of everything. Not that he didn’t trust Punjun, but how is a boy supposed to have everything he’d need without wasting a lot of time? After all, this was a crucial year in their lives. Punjun had just turned 18 and decided to take a gap year to prepare for competitions. He had done well enough in school, even made the merit list in his district, but found himself well below the required level of college entrance exams. Despite the urge to blame...

Incest
2 years ago
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MY MAN AND I SHARE A LADYBOY

My man Roger and I have had sexual adventures that many people would be envious of: some incredulous of even. Around once a month I love having a second man to pleasure me and before I pleasure him while my man watches, and often he will pleasure my man: oral sex only – no intercourse is the rule. In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock. “Some of your...

2 years ago
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JuniorChapter 19 Gladys Sheila Gladys

Gladys wanted to stay in my room and I let her. I didn't know if she was afraid of Charlie or if it was for the reason she gave; she liked the way I fucked. "Did you mean what you said about my tits?" she asked, snuggling against me so I could feel her nipples bore into my chest. "Yes." "Charlie never says nice things to me the way you do." "I know." "You're sweet. But, God Damn, you can be mean, too!" "I know." "You're not generally like that, are you?" Remembering...

3 years ago
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Ladyboys Moving to Thailand and my first Ladyboy

After living in the Netherlands for 33 years I was ready for a big change. I had been toying withthe idea of moving to another country to get away from the stress of it all for a while.I had girlfriends in the Netherlands. Wives.I had one nighters and 2 nighters. I wasn't doing bad for myself.But, there was something missing on the girl side. I love variety. I think I've been withevery kind of girl I COULD be with in the Netherlands. I started thinking about other countries.Other girls. Other...

2 years ago
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The Landlady

THE LANDLADY by BobH (c) 2011 -1- "How do I look?" I asked Cate. "You look just fine," she replied. "Honestly, Mike, I don't know why you're fretting so much." "Hey, it's not every day a guy gets to meet his girlfriend's Dad and I want to make a good first impression." "I'm sure he'll love you as much as I do," she said, coming over and adjusting my tie before...

3 years ago
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Lookingglass Ladyboy

I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding a bargain, I asked myself, than a store that was having a going- out-of-business sale? The store offered everything you could imagine, in every condition you could imagine--sofas, tables, chairs,...

2 years ago
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His Dominant Landlady

Eighteen year old James Morgan was sitting across the desk from an attractive middle aged lady who was explaining to him that there was no accommodation in the Halls of Residence at the University of the Arts in South London. James had been delayed on his return to England after holidaying with his parents by striking French farmers and fisherman who had blockaded both the Channel Tunnel and the ports until their demands were met. Mrs. Heather Talbot was explaining that this year saw an above...

2 years ago
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How I Fucked My Sexy Horny Landlady

Well! let me go straight to the story. This is a story of how I got to fuck my landlady who was seeking a young and energetic dick. A few years back I enrolled for engineering in one of the colleges of Bengaluru. I didn’t get hostel at that college. So I had to stay as a PG in a house in Hebbal. There were only 3 people living in that house at that time: landlord, the landlady, and his son. His son was in the 11th standard. They also had a daughter who was studying CA in Delhi. Aunty, the...

1 year ago
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My Favorite Aunt and The Divorcee Landlady

My favorite Aunt and the Divorcee Landlady By Julie D Like most trannies it all started with a favorite aunt and progressed through a series of experiences such as sexy landladies. I have been an avid reader of FM for the last two years since I got a PC. I was told about the site from a fellow TV in one the London clubs I used to go to as Julie. I go into the site most days to see if their are any interesting stories as some are very rewarding when you are alone and feeling...

2 years ago
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Lost My Virginity To My Trusting Landlady

God did not bless me with looks, personality, features or riches which are all the pre-requisites for wooing women. But what he gave me as compensation were innumerable chances for satisfying my lust. I have had quite a few casual encounters of sexual intercourse with women. All women in my stories are above 26 yrs of age, quite beautiful with well-endowed feminine features. Today, I am narrating another true incident of mine, where I had a spontaneous sexual intercourse with a close family...

1 year ago
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ice cream truck lady

there is this lady that owns a ice cream truck that passes by my house. she is a hottie. mature old lady big tits nice ass omg i get hard thinking of her. a while back i went to go get a cone and when she was serving it she tippy toed to get some thing n her shirt went up and her pants went down a little and i saw her thong. any tips on how i can like flirt with her and get her to fuck???ima copy n paste so it can be seenthere is this lady that owns a ice cream truck that passes by my house....

3 years ago
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Glassy Eyed Little Old Lady

After John retires he starts drinking wine all day. His wife tells him that he is starting to look like a glassy eyed little old lady. She requires him wear the clothes of a glassy eyed little old lady if he continues to drink wine and eventually he becomes one. Chapter One John and Teresa had been married many years. They never had children but took in some foster kids over the years. Teresa had always been a stay at home mom for the foster children and became very involved...

3 years ago
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Adventures of Sonny Red head boss lady

For the last two years I have worked at an manufacturing company on the assembly line making components for cars. The product that my company produced fit several makes and models. We had some job security even if the talk about tariffs did take place.It was decent pay I had my own sutdio apartment in a quite upscale area. No c***dren or girlfriend at the time. I was just working and rushing home to do nothing. I had an up to date American built truck, that blend in well with my southern white...

2 years ago
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Soma8217s Milky Adventure With An Old Lady

Soma, a beautiful busty young girl, got married two years ago to a well-known family in Kolkata. Soma and her husband Paresh have been separated from the family since the marriage. And 4 months ago, she had the good fortune to be a mother. For Soma, a 26-year-old young mother, it became increasingly difficult to work and look after her family. So, Soma’s mother decided to hire a housekeeper. Soon she found one. The housekeeper was an old-aged woman. Her age was around 56 or 57, a thin and...

Lesbian
1 year ago
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Swappy Lady

Swappy Lady Olga Turlovna So, I'll start by saying I used to be a guy who secretly wanted to be a woman. The fact you've found this story means you're probably the same way and I don't need to explain my feelings to you. But I'm beginning with that admission to emphasise God didn't create all of us with female inclinations equal, and I never considered actually transitioning. I wasn't motivated to go through the ordeal of years of expensive hormones and...

3 years ago
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The Perfect Little Lady

"The Perfect Little Lady" I could hear my aunt downstairs at the kitchen door talking then heard the door close. I stood near the upstairs window looking out through the curtains and watched as my new friends walked across the back lawn talking, roughhousing and tossing the football around as they made their way down the alleyway and out of site. I then heard my aunt returning upstairs to her bedroom where I was instructed to wait for her. She entered the room with purpose and...

3 years ago
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Green Beret Loves Asian Ladyboys

Demonde Scott woke up early most days.. He leaned over and kissed his girlfriend’s forehead. He threw on some basketball shorts, a tank top, and a pair of multicolored Nike Joyride Dual Run sneakers. The 5’11”; 200-pound man headed out of his small house on the compound where Westerners lived while working in the Kingdom. He stretched then launched into morning 2-mile run. The air felt thick on his skin. It was around 65% humidity at present, but the temp was good at a little over 80 °F.He...

3 years ago
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That aint no way to treat a Lady

“A fucking lady? No way; how, why?” I babbled, shocked.“Lady, darling; the word is always capitalised,” Cyn, my girlfriend of four months, clarified, “I’m Lady Cynthia Fortescue-Smythe, second daughter of Edward, the Earl of Battersea."“And you are me telling this, why?” I asked, as we lay, post-orgasmic, in her Knightsbridge apartment wrapped in sheets which were, apparently, cut from Egyptian cotton of astronomical thread count.“Royal Ascot silly; we are going tomorrow, and absolutely...

Fetish
4 years ago
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To serve and soothe the Lady

Another short tale. But only because my a.d.d. keeps me from writing long tales. As always, feedback is not only welcome but very much desired. To serve, and soothe, the Lady. The hour was late, or perhaps early as it was now past midnight, when she - who was not a she on the outside - closed and locked the door after the gentleman left. She liked this man, for he was not cold and cruel as some could be and treated her as a person with feelings. A servant, yes, but still a person....

3 years ago
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Education of a Ladyboi

Ever since I can remember I have been a sissy. As a very young boi, I loved playing with dolls and other girlie things. I avoided the company of other bois my age because to be honest, they frightened me. They just gave off a threatening and hostile vibe that I went out of my way to avoid them. Instead I preferred the company of the girls. I took a lot of heat all the way through school, and after puberty I began totally embracing my femininity, by overt means, such as, wearing makeup, girlie...

1 year ago
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The Wonderful World Of LADYBOIS

Oh god - I'm just sitting here, thinking about how lucky I am to have been born a femme! I love everything about femmes. Of course, getting to where I am today - a totally sexy and girly ladyboi - took a long and sometimes circuitous route. Being born male, and coming from the time and place I came from, announcing to the world (or even to yourself!!) was probably not the wisest thing to do. All I ever heard growing up were extremely negative things about anyone who wasn't straight sexually. It...

3 years ago
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91 AVIS AND HER LADYFRIENDS

91 AVIS AND HER LADYFRIENDS My friend Carol called me up one morning and asked if I would like to meet for some shopping and lunch. Since Jon and I would have the day to ourselves, I agreed and we met at the local mall. Carol approached me and unexpectedly kissed me there in the entrance way to the mall. "Good morning" she said as I looked back in mild shock. "Did I shock you?" she asked. I said I was a bit surprised, but then let it go and off we went shopping. Around noon we stopped at...

2 years ago
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Married Black Mans Ladyboi

Torrance Denkins was completely infatuated with transsexuals. He watched shemale porn constantly. He was married to his second wife. In total, he had five c***dren - three by his first wife and two by the current one. Torrance was forty-eight years-old. His betrothed was only 29. The homicide detective walked out of the precinct and got into his personal vehicle. He drove a black 2014 Cadillac CTS. Once he got settled in the car, Torrance started it up and then sent a text message to...

2 years ago
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the barlady

After a long day at work and a meeting with my boss that ended badly. I decided to dive into the local pub the young guys at work always talk about. I walk in and plat myself by the bar. Greeted by a young black woman. I pay no attention with my head down. Whiskey on the rocks.. Make that a double!! She slides my drink over asking.. Rough day? as I take off my tie. I reply with a negative voice.. You can only imagine. And that's when I make eye contact with her.. A pure beauty. Tied up hair in...

4 years ago
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Sex With My Ladyboss

An awesome moment with the busty manager. Hello friends, I am from Kashmir my first story in ISS hope you ll like it. I have been an avid reader of iss. If any women who seek no strings attached fun, or friends with benefit fun can contact me on please be assured of the safety, women’s safety is my first priority. About me, I am a fair handsome looking guy I am a single guy have a decent tool whose sole aim to is to satisfy women, I’m on the heavier side, funny guy. This story goes back in...

3 years ago
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THE CLEANINGLADY

I was just about finished cleaning the house for Mr. Gustavsson, the whole house had been out of a womans touch for years. I had recently got my driverslicense and this was my first real job. I lit lighter and waited for the familiar cloud of Smoke that came when i cigarrette fires up, while Mr. Gustavsson leanedaround the corner and asked if everything was O.K. "No problem Mr. Gustavsson all finished," I said,as i wiped my hand with an old rag , "I'll be out in a minute!"After gathering up...

3 years ago
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You Ladygirl

You Ladygirl Preface If this were a true story, and it isn't, but if it were, I would need to protect the innocent. The innocent in this case is a culture rather than individuals. So to protect a fictional culture I have changed the fictional name of the fictional culture to "Chinese." Me, I am, like the protagonist, of European ancestry second generation on my father's side. I admit knowing little about Chinese culture. There is a high likelihood that this story is chock full of...

2 years ago
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Visit to Mistress LadyJulia

below is a real account of a visit I had to a professional Mistress. It was a bitter sweet memory that I will treasure for the rest of my life So here at last is the account of my first visit to a Mistress. That being Mistress LadyJulia. It is not as eloquent as I would have liked but I was trying to capture the emotions I was feeling. It has been read but not censored by my Mistress as I may have stated in my diary. She did not want to change my words but was concern I may have given...

2 years ago
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Second Visit to Mistress LadyJulia

My appointment with Mistress LadyJulia was at 11 again and I arrived on the dot flowers in hand. It was a strange feeling to be standing there again. All through the previous week I had berated myself for wanting this. I had even talked myself out of coming a couple of time, but I so much wanted this! So now as I stood waiting I felt calm and ready, tinged with anticipation of what was to come. I knocked at the door and stood back head bowed as ordered. Seconds later Mistress answered the...

2 years ago
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The Shack Ladykiller

The Girls of Hollywood Fort Leonard Wood, Missouri “Hey, Hollywood!” I was just bringing the micro van around the first set of barricades when one of the assistant instructors, Chrissie, jogged around the corner waving for me to stop, long blonde ponytail streaming through the back of her “Instructor” cap. I brought my vehicle to a stop. “Mac told me to tell you they aren’t taking it seriously. They’ve aced everything, but they’re getting cocky. It’s an all-female squad of Reserve MPs,...

1 year ago
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LadyboyGold

Ladyboy Gold! Good evening, ladies and gentlemen, boys and girls. Tonight’s sexual entertainment is full of beautiful ladies, and uh, hot boys? Sorry, no. I’m still a little fuzzy from all the Everclear and Cialis last night. LadyboyGold is a premium site that doesn’t specialize in ladies or boys, at least not in the traditional sense. I’m sure I don’t have to explain that to somebody browsing my list of shemale sites, though.LadyboyGold claims to be the number-one reviewed TS site in the...

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1 year ago
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LadyBonersGW

Since I know the majority of my public are the horny lads who are just looking for some delightful wanking, let me start this review by saying that r/ladybonersgw/ is not for everyone. If you did not get the memo, the name itself states ‘Lady Boners GW,’ where GW stands for Gone Wild. Now, I know that some of y’all might be expecting to see chicks with dicks, but that is not what Lady Boners implies.So, what the fuck is r/ladybonersgw/ all about? It is simple… it is a subreddit where dudes can...

Porn for Women Sites
1 year ago
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LadyBoners

Do you know what time it is? It’s time for ladies to show that they can have sexual tastes too and that they can get aroused just like men have. That being said, chicks like to keep it a bit classier when they are looking at the content, which gets their blood pumping. So, if you’re a girl who wants to get her groove on and explore her sexuality in an inclusive environment, then you’ve come to the right place. Today we are looking at a sub called /r/LadyBoners, and while I’m not someone who...

Porn for Women Sites
3 years ago
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Luck Be A Lady

Luck Be a Lady By Anonymous "Dealer showing three. Player showing eleven." The woman dealer was quite expressionless, as most casino employees were expected to be. It was obvious she didn't like me, particularly since I'd spent the last hour cursing her existence for the cards she was dealing me. I was down. Way down. Down to my last $20,000, half of which I had riding on this hand. I'm a professional gambler. Blackjack is my game. My luck has been less than...

3 years ago
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The Landlady

Just a silly story I wrote over a couple of nights. Completely fictional, hope you like it.NEW TENANTSJack started seeing Lorna and it became serious. Trouble was that Jack being eighteen was a little naïve regarding women and couldn’t see that she was basically selfish. They say that love is blind and it was in this case, fortunately Lorna wasn’t prepared to become tied down with marriage and suggested they merely live together. That would give her a get out clause when she tired of...

3 years ago
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My Landlady

My LandladyI had been having a bit of a problem, uncontrollable erections around my landlady! I am in my thirties and found myself needing to work in London though I live out in the country, so I got a Monday to Friday room let in a nice place with a family. I am in the attic so get left to myself and all was fine. I miss my wife through the week and get a bit horny so my eyes wandered a little. At first it was the landlady’s daughter but then it became the landlady. She is in her early...

2 years ago
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SHARING THE BATHROOM WITH MY LANDLADY

I fancied my landlady from the first time I met her. I had been wondering how I could orchestrate a situation where bye I could expose myself without making it too obvious and possibly being thrown out into the street. Then one morning my patience was rewarded….I was in the shower, lazily enjoying the sensation of the hot water spraying like rice grains on my swelling member which was resting in the palm of my hand. As it swelled I went into that world which is private to all except the one who...

1 year ago
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Saroj the Landlady

Hi ISS Readers. Here I am back with a real sex encounter I had just few days back with my Boss niece Landlady. My Boss has asked me to locate a good house for her niece. With the help of my friends I was able to locate a good house for her Delhi. After finalizing all the things my friend has arranged meeting with Landlady to complete the formalities like security advance, agreement etc. I went there and had meeting with Saroj (Landlady) who told that she is widow and her only son is doing B....

Incest
3 years ago
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To the Manor Born Part 2 Becoming a Lady

To the Manor Born Part 2: How to Become a Lady Chapter 1 - Changes I struggled toward consciousness, trying to shake the cobwebs from my drugged mind. I shifted in my bed (at least I assume it was a bed) and winced in pain. My backside hurt like heck, my throat felt like sandpaper, my stomach felt like I'd been worked over by the Hell's Angels, and it felt like a large animal was sitting on my chest. All of this came as a significant surprise to me. The last thing I remember was...

3 years ago
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A VIRTUOUS YOUNG CHRISTIAN LADY

Cathy Calusa, an exemplary teenage girl with high moral values, who took a vow to keep her virginity until she is properly married. She is an honor student at the Christian High School she attends. She loves tutoring young c***dren with their school work, and instilling them with good Christian values. Cathy is very thankful for her strict Christian upbringing by her mother, who taught her how to be a proper Christian lady. Cathy has been baby setting since she was twelve years old, so she...

3 years ago
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A Ladys

A Lady's by Nefertari CHAPTER 1- ANNIVERSARY "The eternal feminine draws us onward" Goethe The cab headed downtown, then west, windshield wipers flapping, a cold rain falling. From my current prospective, it seems like another lifetime in another world. I was a young accounting clerk in my first real job on the way to an important company social function that Friday evening. The firm had always been involved in importing and exporting and was easily the oldest commercial...

3 years ago
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Lake Lady

Lake Lady, by Armond "And there I saw mage Merlin... And near him stood the Lady of the Lake, Who knows a subtler magic than his own- Clothed in white samite, mystic, wonderful. She gave the King his huge cross-hilted sword, Whereby to drive the heathen out: a mist Of incense curled about her, and her face Wellnigh was hidden in the minster gloom..." -Idylls of the King, by Alfred, Lord Tennyson "And when I was fifteen yeere old, then was I...

2 years ago
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The Cleaning Lady

The Cleaning Lady Belladonna I had spent some of my weekends working as a cleaning lady in my own office from time to time for over 20 years. I began doing it not long after I started my company. No matter where the office was located, I always found time to go in and clean it up when no one was around. My company's office is currently situated in a building that the company owns. The office occupies a full floor of that four story building. I had built up the corporation...

2 years ago
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Dark Knight The Lady

This short story is a bit longer than my usual ones. But to take away events of the story to make it shorter, would take the integrity and true power of this story. Please read it careful and you wont regret it, this story means alot to me…it took me 6 months to write it, because I wanted it to be just right. thank you. London, England May 1785, Standing alone on the Stanhope terrace, Lady Georgia Kent watched, as the first ball of the season was in full swing. This was her coming out...

2 years ago
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LIQUOR STORE LADY

There is this liquor store in the mall where I usually do my shopping for groceries. I’ve been coming in there for several years every now and then to buy my booze. Most of the time when I came in the store, there was the same lady behind the counter, who really attracted my attention. She was in her early fifties, I guessed, not too tall and somewhat chubby. She wasn’t exceptionally beautiful. Her face was nice and friendly, with kind blue eyes and nice full lips, but rather plain...

1 year ago
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Boss Lady

Boss Lady by Tim Roberts Diane was the first female supervisor I had ever had. The first day she arrivedin the office I was stunned by how beautiful she was; early 30's, long brownhair and brown eyes, about 5'6", and slender with a great build. Yes, she wastruly very pretty. But what really turned me on was the way she dressed andhow she handled herself in the office. She managed to do a real good job oflooking business-like and sexy at the same time, wearing suits but with thedress cut short...

4 years ago
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My Elegant Lady

“Go piss off and walk your fucking dog!” My girlfriend shouted at mefor coming home drunk late last night. My girlfriend and I share a flat. A new place we recently moved into and a new neighbourhood for us. As you have gathered, we have, well it’s my dog. I had slept most of the day and it was around six o’clock Friday evening. Yeah I know, lazy bastard. Well we both had a few days off work for the move. It was Friday, and we had the weekend off. I was out with a few mates drinking, chatting,...

Mature
2 years ago
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A Portrait Of A Lady

"Lorenzo. So good to see you. I was wondering when you would be so good as to call."I am Lorenzo. I am an artist. I am Hispanic and my family have lived here in California for longer than any Anglos present here today. Only the Native Americans have been here longer. I am proud of my heritage. It had been a year's time since I painted Lady Gwen portrait. Always since then I had wished to come by her brothel and observe my work in its permanent home. My work is shown in many homes and salons...

Interracial
3 years ago
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The liquor store lady

When I came in on Saturdays, when it was always very busy, there often was a girl about sixteen or seventeen years of age with her. I always assumed this was the lady’s daughter who was helping her out, because there was a certain resemblance in both women’s facial features. They shared the same blue eyes and full lips. Otherwise the younger woman looked quite different, being quite slim and substantially taller than the older one as well as having much longer, curly blond hairs. Though she was...

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