Sally's Little Sissy free porn video

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Sally's Little Sissy I'd been writing a regular piece for a woman's magazine on unusual marriages when someone in the office said I ought to visit Sally and Pete Kendall. They gave me a number and I rang one Tuesday morning. Sally answered and said that she was more than happy to be the subject of an article, subject to the usual anonymity. She could speak for Pete and she knew that he wouldn't mind either. I asked about the marriage and Sally just said that it would be better if I visited them in their house. She would try to answer any questions that I might have. I fixed a date for 2.30 the following Thursday afternoon. I wrote down the address and thanked Sally for her co-operation. So two days later I was driving through the leafy suburbs, my sat nav directing my to a quiet side street with large detached Edwardian houses, mostly with a couple of large cars on the drive. I was glad that I was formally dressed for work in my favourite black suit; black jacket and matching knee-length skirt. Sometimes I would just wear a pair of tight jeans and a floppy top. I parked outside Sally and Pete's house. Like the others in the road it exuded affluence; a large, old house in a large garden, a Mercedes on the drive, an immaculately maintained house and garden. I stepped noisily up a gravel path to the front door and rang the bell. I was half expecting a servant to answer the door but no, it was a smartly dressed woman in her late-thirties with a welcoming smile. I knew without her saying that this was Sally and that I was going to like her. I introduced myself and she beckoned me in and I entered a large hallway with high ceilings and a lot of wood panelling that I assumed was oak. Sally pointed to a door and I led her into a large room. Sally called it the drawing room. It was beautifully furnished with a deep carpet, leather chairs, oil paintings on the walls and art deco pieces around the open fireplace. "Do sit down," oozed Sally. There was no sign of Pete. We sat down and began 10 or 15 minutes of small talk. This is always the case when I am interviewing somebody. It's a bit like the opening of a chess match. I was sounding out Sally. I needed to find out a few things about Sally and Pete and I wanted to put Sally at her ease. I discovered that Sally and Pete had been married for 12 years and for the past eight years they had lived in this house. They had no children. They were obviously comfortably off - Sally has a job in finance. She wasn't very clear what she did but I gathered it was to do with stockbroking, normally a very male dominated profession. We didn't get as far as Pete's job but I got the impression that he was not the major bread winner. Eventually it was time to get down to business. "Is Pete going to join us?" I asked. "My husband will come in later," Sally reassured me. "Tell me about your marriage," I said, turning on my tape recorder. Sally stood up and walked over to the fireplace. On the mantelpiece was a small envelope. "Before we start, I think you should see this," Sally said. She took a photograph out of the envelope and handed it to me. It was small, perhaps four inches across. It was a photo of a cute little girl sitting on the floor with a dark background. She was wearing a short-sleeved knee-length gingham dress in pale blue with a white lace collar. She wore it with white knee-high socks and black patent leather Mary Jane shoes. Her dirty blonde shoulder-length hair was brushed into two pig tails, each fixed with elastic and decorated with two pale blue ribbons tied in a bow. She was cute and looked about eight years old. She was cute but something wasn't quite right. I remembered that Sally had told me that she had no children. The girl in the photo seemed to be wearing make-up which surely no eight year old would wear; pink lipstick and blue eye shadow. And the heels on her Mary Jane shoes were too high. No eight year old would be allowed to wear four inch heels. Her face was also too grown up... Then the penny dropped. "Is this...?" I asked not finishing the question in case I'd got it wrong. "Pete? Yes. That is my husband. Of course I always call her Penny now. Isn't she cute?" I had to admit that Pete or rather Penny did look cute. She looked pretty and the dress suited her. Sally passed me a second photo. It was obviously another photo of Penny, this time wearing a typical school uniform of white blouse, school tie, pleated grey skirt, again with white socks and Mary Janes. Under one arm she held a teddy bear. Again I had to confess that Sally's husband looked cute. And feminine. "And how often does Pete crossdress?" I asked Sally, expecting her to say once or twice a week. "Oh, all the time," she replied. "Penny is 24/7. I threw all Pete's clothes away a few years ago." "Isn't it humiliating for Pete to dress like a little girl in front of his wife?" "Yes I think it is. But that's she wants. She doesn't have to dress like a little girl. She chose that gingham dress. She often dresses like a little girl. Humiliating? Maybe but she likes the humiliation." I noticed how Sally referred to her husband as 'she.' "Really?" I asked. "Was it her decision to wear that school uniform?" I made a few notes on my reporter's pad. "Of course. Look she's a grown man. I couldn't force her to wear a dress. If she didn't like it, she would leave." "I suppose so," I said. "Yesterday she wore something much more humiliating. Look I've got another photo here." She sorted through the photos, found one and handed one to me. It's hard to describe what Penny was wearing but it looked like a very frilly, pale pink, adult size baby's dress with a sewn-in white satin and lace bib. Again the outfit was complimented by white knee-high socks and shiny black Mary Janes. In one hand she held a baby's bottle and in her mouth she had a pacifier. Sally was right. This was much more humiliating particularly as the dress was so short that it did cover a pair of very pink frilly knickers. And the knickers bulged out as if something padded was on underneath. I had to ask. "Is he, or do I mean she, wearing a diaper?" Sally replied, "Well naturally. That's what babies wear." I was half- inclined to ask if the diaper was used for, well what babies use diapers for and who changed the diaper. But I thought that perhaps this was too much information and not something the readers of my magazine really wanted to know. "And this was yesterday?" I asked. Sally nodded. "And today?" I asked. "You'll have to wait and see," said Sally mysteriously. "And she really doesn't mind being dressed as a little girl?" I laboured the point. "Mind? Of course not. She loves it. And she chooses what to wear. That gingham dress is one of her favourites. She does have more grown-up clothes as well." "But you said, you'd thrown all his male clothes out a few years ago." "Yes. In fact, Penny had been begging me to throw away all Pete's clothes for ages. They were just getting in the way. I thought that maybe he should keep a few. Just in case. But he said get rid of them and frankly he hadn't worn them for years so I took them all to Oxfam. I guess by then we were sure that she wouldn't be going back." "So it was a joint-decision?" "I think it's time for you to meet Penny. You can ask her if she wanted to hang on to those male clothes." Sally leaned to the left and pulled a cord that I had not noticed that hung close to the wall. A little bell sounded and within a minute the door opened. I must confess I had been wondering how she would be dressed. Little girl? Schoolgirl? Adult baby? Or something more mature. In came Penny. Little girl? Schoolgirl? Adult baby? None of them. She was dressed in a French maid's uniform; a short, black dress with a white lace trim, a white lacy apron, a white tutu petticoat that just stuck out below the dress's hem and a black and white lacy head band. She wore sheer black nylons and what looked like 4 inch black stilettos. Penny minced over to us, swinging her hips in a very feminine manner. From closer to I could see that she was wearing full makeup but it was subtle and feminine and she looked rather pretty. "You rang, Mistress Sally?" she said in a soft voice. I could have sworn she dipped in a little curtsey. "Yes, Penny. This is Rebecca Ward from Wise Woman magazine. She will be doing a piece on our marriage." Penny said nothing but nodded a hello in my direction. "I'd like you to make us all a cup of tea and then I want you to join us and answer any questions that Rebecca has for us." "Yes, Mistress Sally." There. The curtsey again. I was right. "Let's inspect you first," Sally said. "Do a twirl." Penny turned through 360 degrees on her heels. "Very good," Sally said. "That dress looks fantastic." "Thank you, Mistress Sally," Penny said. "Are you wearing a petticoat? Show me." We could both see clearly that Penny was wearing a petticoat but that wasn't the point. Sally was showing me that what she said was the law in this household. Without any embarrassment, Penny slowly took the hem of her dress and lifted it up to reveal the lacy petticoat. "Very nice. And your panties? Are they clean?" God this was humiliating for Penny but she didn't seem to mind, standing in front of her wife and a stranger, dressed as a maid following orders obediently and without a demur. And now she had to show us her spotless pretty white panties with layers of lace. "Good girl," Sally said. Penny let go of the hem and smoothed her dress down. She looked a little awkward being called a girl in front of a stranger. If she blushed it didn't show under her makeup. She curtseyed again and minced off to the kitchen. "Isn't she cute?" Sally said. "I love that maid's dress. It fits her like a glove and she always looks immaculate. Her seams are always arrow straight. Did you notice how she gives a tiny flash of petticoat as she walks? So-o-o sexy." "So Penny is your maid?" I asked. "Oh yes," said Sally proudly. "And she is an excellent maid. She cooks the meals and clears away; she does all the laundry and keeps the house spotless. I don't have to do anything which means I don't have to worry about housework when I'm at the office. I know when I get home the place will be like a new pin." I nodded a little enviously. "If I request any irregular items like spring cleaning the kitchen or turning over the mattress, she does it without question. She always does exactly what I say and she never forgets," Sally went on. "I am impressed," I said. "Only when she has finished her chores can she change out of her uniform." "Does she always do exactly what you say? Has she ever disobeyed you?" "Once," said Sally with a knowing look. Clearly, whatever it was, it would never happen again. There was an almost imperceptible knocking on the door and in came Penny carrying a tray. She came over to the middle of the room and put the tray down on a low table, bending her knees carefully in that short dress to avoid indecency. It couldn't have been easy in those monster heels but Penny didn't hesitate for a second. "Milk, Miss Ward?" she said. "Yes please. No sugar." She poured the tea, took the cup and saucer over to me and handed it to me with a curtsey. She repeated this for Sally before pouring a third cup for herself. She gave a little cough. "Sit down, Penny," Sally said pointing at a vacant chair. Clearly Penny was not allowed to sit down without permission or even allowed to ask if she could sit down. She picked up her cup and saucer and carefully sat down brushing her dress underneath her as she did so to prevent any creases. She crossed her legs in a very feminine fashion revealing a lot of thigh. She was beautiful. It was hard to believe that she was actually a man and I caught myself wondering if I found Penny attractive. I can't deny that I found the combination of pretty face, gorgeous long legs but masculine underneath and submissive attitude very alluring. "Fire away, Rebecca. Ask whatever you like." I put down my tea cup, picked up my reporter's pad and pen and tried to concentrate on the matter in hand and not the pretty sissy sitting opposite me. "Where did you meet?" I asked first. "In Canal Street, Manchester one February night. I was there with three other girls from work, "Sally said. " We were curious I suppose and we ended up in a place called Napoleon's. Do you know it?" "No," I lied. "It's a hangout for t-girls. Dancing, drinking, a bit of fondling in the toilets. Lots of mirrors. T-girls just love mirrors, don't they Penny?" Penny nodded. "The four of us went in there. There was a t-girl sitting on a stool at the end of the bar. All on her own. Looked like she had no friends. Betty no-mates. So I went over and started talking to her. It was Penny. The rest is, as they say, history." I wrote a few things down. "It's true," said Penny. "I had no friends. I'd only recently found the courage to go out dressed. It was probably my third or fourth night out. I was there on my own. I knew nobody but just to go out in a dress, heels, wig and makeup felt fabulous. I could feel the glamour, breathe in the atmosphere, hit the dance floor upstairs in the small hours before heading back home to being Pete again." "Tell Rebecca what you were wearing," Sally said. "I wore a blonde shoulder length wig, a pale yellow top, clip on earrings, a necklace, a pale blue denim mini skirt, white pumps with four inch heels," said Penny. "My makeup was rubbish. I have learned a lot since about what top goes with what skirt, what colour to wear with what, how to do makeup and so on." "She's right. She looked OK in the darkness of the club but she had a lot to learn. We still have a few photos from that night. I certainly didn't think it would lead to us getting hitched." Sally laughed. "So you met Penny that night. Did you meet Pete?" Sally replied, "I didn't meet Pete for a few weeks after we met. We swapped numbers. I didn't expect him to ring me so I rang him the next evening and invited him round for a meal the following Saturday night." "I remember asking Sally, 'as Pete or Penny?' and she replied 'as Penny of course.' I accepted straight away and made a note of the address," Penny said. Sally butted in. "Now I had some difficult decisions; what to cook and what to wear. The 'what to wear' was the hardest. I didn't want to look too conservative but nor did I want to look like a slutty. In the end I settled on a dress that was about three or four inches above the knee. I thought it might be a little too provocative until I answered the door bell and there was Penny in a spray-on, tight, arse-length sparkly skirt that left little to the imagination." "I had bought it specially," said Penny. "Really, all my skirts and dresses were a bit short for a first 'date' so I went shopping to buy something longer. But I saw this shiny micro skirt and fell in love with it. I think Sally's jaw dropped two feet when she saw me come into her flat in such a tiny skirt, a tight top, tights and six inch heels. But hey, I'm a t-girl. That's what t-girls wear." "We agreed to meet in Napoleon's the following Wednesday and for me to cook a meal for the two of us the next Saturday," Penny continued. "I couldn't decide what to wear for Sally's first visit to my flat but even in those days I liked French maid's uniforms. I had a couple which I wore for cleaning the flat; both were black with a white trim; one was PVC, the other was satin. So I decided in for a penny and wore the PVC one." Sally continued, "That was the first time I'd seen Penny in a maid's uniform and she looked as sexy as does now. I think I fell in love with her that night when I saw her in the PVC dress. I couldn't take my eyes off her. Or my hands." Penny laughed. Sally went on, "She needed to practise movement and how to sit down without showing her pretty panties but I really fancied her that night. Her makeup was still a bit rough at the edges so I gave her a few tips there too." "Sally was really helpful," said Penny. "A lot of her advice was very useful. My makeup was entirely self-taught and, frankly, although I'd got a lot of tips from the Internet my makeup skills were non-existent. Sally's advice was welcome particularly about shades of colour." "That night was really the start of our relationship," said Sally. "We slept together for the first time that night." "In the PVC maid's uniform, Penny?" I asked. Penny just smiled. "That's our little secret,"she said with a wink. "Weren't you dying to meet Pete? I asked Sally. "Yes," Sally replied. "I suppose I was curious but sometimes it is best not to rush things. It was a few weeks before I met Pete. We had a few drinks together in a pub and to be honest, I preferred Penny. She's outgoing, sexy and pretty. Pete is a quiet, balding, insignificant little man. Penny is a fun-loving extravert; the life and soul of the party. Pete is a bit of a wallflower. Yes, I definitely prefer Penny to Pete." "Do you mind that, Pete?" "Not at all. I'm a crossdresser. I like wearing feminine clothes," Penny said. "They make me feel good. They give me a buzz. I can't explain why but I do and I particularly like the sissy look; lots of lace, girly items, maid's dresses like this one, school uniforms, party dresses, baby dresses..." "Yes I've seen a few photos," I said. "But isn't it humiliating, dressing like that in front of Sally? I can appreciate that some men like to dress as women but to dress as a little girl or a baby... " "Well they say that there is no accounting for taste," Penny joked. "I like wearing frilly things. Sally likes me wearing frilly things. No it's not really humiliating. It's fun." "So you started dating," I said "Then what?" "We had been dating for about six months before Sally invited me to move in with her," said Penny. "As Pete or Penny?" I asked. "Or maybe both." "Oh only as Penny, of course," said Sally. "But under twelve conditions." Sally smiled. "Do you mind telling me what these conditions were?" I asked. Sally replied, "Not at all. I have them written down here to remind me. They were: 1. You will give up work - my job is very well paid - and dress as Penny 24/7 2. You will be called Penny or Maid Penny at all times 3. You will call me Mistress Sally or madam 4. You will wear make-up and a wig at all times 5. You will keep the flat clean at all times. 6. You will cook all the meals and clean up afterwards 7. You will do all the laundry and ironing 8. You will wear a maid's uniform when you are performing your cleaning, cooking and laundry duties but at other times you can choose your own feminine clothes. 9. You will not pleasure yourself at any time without permission from Mistress Sally 10. You will wear a pussy plug at all times 11. You will obey my instructions at all times 12. If you break any of these conditions, you will immediately be punished." "So, Penny, did you agree to these conditions?" I asked. "Of course I did. I hated my job. I loved being dressed and I loved being a maid. It was a total no brainer. I handed in my notice at work and moved in the following week. Within a few days I had forgotten all about Pete and was loving being Maid Penny 24/7." "What about the punishment? Did you really agree to that?" "Why ever not?" Penny asked. "Well I assume that we are talking physical punishment here," I said. "Do you let Sally pull down your panties and spank you?" "If Sally thinks it appropriate to spank me because I have broken the rules, then I deserve to be punished," Penny said diplomatically. "But it's degrading. Even more humiliating that dressing as a baby girl," I said. "You cannot be a transvestite without some humiliation, degradation and sometimes pain," Penny replied matter of factly. "I always think that dressing is similar to taking a drug. It gives you a real high. Some girls get their high from dressing like a slut. Others like dressing as a schoolgirl, a naughty nurse or a French maid. And for me the best high of all is to dress as a sissy. The bigger the sissy, the more the shame, the greater the high." "We'd decided on a one-month trial to start with," said Sally, moving the discussion on. "We agreed that if either of us was unhappy with the arrangement we would break the whole thing off. But we were both blissfully happy that we hardly needed to discuss it. The next stage was marriage. We agreed to wait another 12 months to see how things developed and we agreed that if we were as happy then, we would get married." "So did Penny propose on bended knee?" I asked. "Of course not," Sally said. "I proposed to her - on bended knee. She had to accept of course. Remember she must obey my instructions at all times." "And who was the bride?" I asked. "We both were," Penny said with a smile. "We wore identical outfits; white mini-dresses with lots of bows and lace, white stockings and suspenders, white shoes with a 4 inch heel. And, of course, veils and bouquets." "I have a photo here," said Sally passing me a photo of two pretty brides in rather short wedding dresses. "And I adopted Sally's surname," said Penny. "I rather like being Mrs Penelope Kendall." "And that was 12 years ago and I haven't regretted it for a minute," said Sally. "Nor me," said Penny. "You must have had some rows?" I asked. "Not one," Sally said. "Really?" Sally justified herself. "Of course. Remember the twelve conditions. Penny has to obey my instructions at all times and if she breaks any of these conditions, she will be punished immediately. Penny is a good girl. She always does what I tell her." "Oh yes. I'm a good girl. I always do what Mistress Sally tells me," said the sissy. "But supposing Sally asks you to do something you don't want to do?" I asked her. "It's a question of trust," said Penny. "I trust her to make the right decisions for both of us. If she tells me to do something it must be right." "That's why our marriage is so strong," said Sally. "Because we have a clear relationship and Penny will always do as I ask. We each have clear roles; me as the breadwinner. Penny as the maid. I just love being married to Penny." "Are you on hormones, Penny?" I asked. "No," she replied. "Not yet," said Sally. "Maybe some time in the future, I'll put her on a course of oestrogen. Can you imagine pretty little Penny with gorgeous little titties? You'd love that, Penny, wouldn't you?" "Yes, Mistress Sally," Penny replied but her body language suggested that this was not entirely true. Then Penny stood up and asked, "Can I make you both another cup of tea?" She curtseyed to both of us and when we accepted her offer, she went scurrying to the kitchen to put the kettle on. "I bet I know what you're thinking," Sally said when Penny was gone. "I bet you're thinking that you'd love a maid like Penny." "Well of course it would be great to have someone do all the chores around the house," I said. "I can't imagine my husband in a maid's dress." I laughed. We chatted a bit more before Penny the maid came back with more tea. She poured it and handed us both a cup. "Thank you, Penny," Sally said. "That's all for now. You can go and change if you like." Penny tottered out of the room in her heels and we continued chatting. "Can I ask you something off the record? Have you been unfaithful, Sally?" "Oh dozens of times," she replied without any apparent look of guilt. "I must confess I love hunky men. At present I have three boyfriends that I see on an occasional basis." "For sex?" "I think you can work that out, Rebecca, but don't look so shocked. I get turned on by strong, muscley, manly men who are well hung. The boyfriends can all offer me something that my little sissy husband can't offer." I wondered if the tape recorder had captured her comments about her husband and her boyfriends. "Does Penny mind you having sex with other men?" I asked. "Other men?" said Sally quietly with a laugh. "Penny isn't a man. She's a little sissy. And does she mind? Who cares if she minds? I'm her mistress. I make the rules." "Has Penny ever been unfaithful?" Sally shook her head. "Oh no. But the fact is that Penny needs a boyfriend; a hunky man who will deflower her tenderly. I'll let you into a little secret. For the past year or so I've been looking for a boyfriend for Penny. I've not found Mr Right yet but when I do Penny is going to really enjoy it." "Is Penny looking forward to being deflowered by Mr Right?" "I really don't know but if I can find two suitable men, we might even have a foursome," Sally announced openly. I smiled at the thought. The thought of Penny being deflowered aroused me a little. "Have you got enough for the story?" Sally asked. "I think so. Now I think that we agreed to use false names to protect your privacy." "Yes." "And would you be willing to have your photo taken for the article? We take photos from behind to hide your identity. "That sounds a good idea." At this point the phone rang. Sally quickly went into the kitchen to answer it privately. I could almost catch what she was saying. There was a lot of giggling and I guessed that the call was from one of her boyfriends. Finally Sally said, "OK then. See you in ten." She came back in with a smile all over her face. "Sorry but I've got to go out," she said to me apologetically. I was a little surprised but I had enough material for my article. "No problem," I said. "Can you see yourself out?" "Er yes." I started to pack up my things and put my tape recorder back in my bag. Sally left in a tearing hurry as if she had one hour to get to her boyfriend's house, have a quicky and get back home again. "Bye," she called blowing me a kiss as if we were old friends. "I'll email you a draft copy of the article. And the photographer will contact you. OK?" "Sure," she said. "Say goodbye to Penny." "I will." And she was gone. Just like that. In such a rush. I hadn't even finished my tea. I took a couple more sips and put my notepad in my bag as well. I checked my makeup in my little mirror and painted on a new coat of lippy. As I was about to get up and leave, the door opened and in came Penny. No longer dressed as the maid, she wore a short, tight mini-skirt, a tight stretchy top and even higher stilettos. Her makeup had been redone. There was a little too much black stuff around the eyes but like her long legs and her tight top, it was sexy. She minced over to me and sat down on a chair opposite me. Now I would never describe myself as having Sapphic leanings but I must say that I definitely found Penny sexually attractive. She came over and sat opposite me. With her stocking tops, suspenders and white silky panties showing, I must confess I was aroused. "Would you like to sit next to me on the sofa?" I asked her. "Sure," said the sissy mincing over next to me. "You are very pretty," I said as she sat down. She didn't seem to mind that the tight skirt rode up to reveal her stocking tops. "And so sexy," I added. "Thank you," she said blushing. "It's hard to believe that under your skirt you have ... you know ..." "Well I have. Do you want to see?" "Well maybe later," I said non-committally - but I did want to see. I adjusted my position on the sofa making sure that my knee length skirt rode up to reveal some of my thighs. Penny correctly took this to mean that I was inviting her to stroke my legs. She took the lead, rubbing my thighs while I put my arm around her shoulders. I had never had a girl stroke my thighs before and it was very arousing. Penny also found it arousing because I could see a bulge in her tight skirt. We kissed. Her lips tasted of sweet lipstick. Her tongue tasted like wine. I was loving it. "Have we got time? Have we got time before you mistress gets back?" "We have plenty of time, Rebecca. Come up to my bedroom." She led the way. I followed. Her bedroom was decorated in a very girly way. All pinks and pastel shades with lots of flouncy touches. I kicked off my shoes, pulled my jacket off and then my blouse. Then I took off my skirt and tights. I unhooked my bra and wriggled out of it and finally I pulled down my panties. I found a condom in my bag. Naked as the day I was born, I climbed into bed. Then I noticed Penny. She was naked too but she had the amazing combination of small but feminine breasts and an erection. She got into the bed. We couldn't wait. We were so aroused and a few moments later having exploded in orgasm, we both lay still trying to get our breath back. "We'd better get dressed," Penny said, "in case Sally comes back." I looked around. Picked up my underwear and tights and put them on. Then I redressed in skirt, blouse, jacket and shoes. I checked myself in the mirror and used my fingers to make my hair look OK. My lipstick had disappeared so I found my bag and redid my lips again. I looked across at Penny. She was getting dressed but she was not wearing the 'fuck-me' outfit she wore before. She was wearing the pale blue, knee-length gingham dress in with a white lace collar that I'd seen in the photo, together with white knee-high socks and black patent leather Mary Jane shoes. She had brushed her hair into two pig tails, tied in a bow. She was not as sexy as before but I still found her cute. Breathlessly we both went downstairs. "Oh Penny," I said. "When can we do that again?" I asked. I don't know," she replied. "Sally works at home a lot. But she spends time at the office and visiting her boyfriends. But she expects me to do my maid duties when she's out. But I can get the chores done quickly even you want to meet me again. I won't be able to ring you because Sally always checks the itemised numbers on the phone bill." "Haven't you a mobile?" I asked. "Sally won't let me have a mobile. What I can do is phone you from the pay phone at the supermarket. Give me your mobile number." I wrote it down for her. "I will buy a pay as you go mobile for you so that in future we can communicate by text," I said. "I'll have to hide it from Sally." "Yes." And so began my affair with Penny. It went on for a long time until we were caught in flagrante delicto by Sally. Still that's another story. To be continued?

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It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

4 years ago
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Sallys Holiday Part 6

The following morning I tried to draw Sally on what was in store for me, but she just smiled and said, ‘All in good time.’ We pottered about the house and garden for the morning, then, after lunch she led me to the bathroom. We showered and then she had me sit on the bed and watch while she put on a suspender belt, stockings, a pair of high heels and a flimsy shift dress which hugged her curves and left little to the imagination. While she dressed she set the scene… The events of the previous...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

2 years ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores 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 moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 39
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

4 years ago
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Sallys Holiday Part 4

Later that morning, Sally said she wanted to go shopping, I groaned, saying that I would rather not. She sidled up to me saying that we could have a little fun while we were out. I looked inquisitively and she said that she would wear something sexy and we could do a bit of flashing. Now she had my attention, we had done this a few times before and I just loved the reaction it got from other guys. I had readily agreed, so she went and changed and we headed out. She had put on some seamed...

2 years ago
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Sallys Holiday Part 1

Some time ago my wife, Sally, took up the offer of a couple of girlfriends to join them on a short holiday to Ibiza. The weekend before she went, we were shopping for bits for her to take when she asked my opinion on a skimpy bikini set, consisting of a thong, plunge type cleavage enhancing top and a little matching skirt. I love her showing her gorgeous body off, for a woman in her late forties she is firm and shapely, with gorgeous round tits – all natural, so encouraged her to get it. I...

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