Maid To Measure, Or Sissy Slave By Design, Part One free porn video

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(Note from Author - This final more polished version would not have been possible without the very kind help I received from Vickie Tern. Thanks again Vickie) Maid to Measure or Sissy Slave By Design, Part One [by Mistress Kathrine] Nick It was early on Monday morning when the CEO himself knocked on Nick's office door and asked if he was busy? Nick had never said anything more than hello a few times to the man. What was this all about? Had he been fired? Was the company being restructured? Nick just mumbled a "No, come in," trying hard to smile. Meanwhile he mentally stuck on hold the list of things he had spent the entire weekend carefully organizing in his mind. Things he was just about to tell his secretary, and the order they should be done in today. In an attempt to get his department back on schedule. "Nick I realize you're busy working on sorting out that raid 5 glitch in the latest Upgrade for the Thunderbolt series. But I have a very unusual special favor to ask. You don't have to do it of course" (Yeah as If!!! Nick thought) "and you're going to think I need to be checked into the nearest funny farm for even asking," (Most Likely) "However it is something that is a request from my best and brightest. They believe you're the one with the level of knowledge that can talk them through, and answer a lot of technical questions they have. They seem to be convinced the techies under you can't tie their shoe laces without your guidance." "Well that's very flattering Sir, what is it they need?" "Call me Rob, please" said the CEO with a warm smile that greatly lightened the level of stress that his arrival had given Nick. "Do you know my VP for Global Marketing Kathrine Gilbert?" "I don't believe there is a person working here Sir, sorry Rob, that doesn't at least know of the supermodel working upstairs," Nick said with a big smile. Rob began to chuckle at this statement before continuing. "Yes I've often wondered why she worked so hard through Uni and the high stress world of corporate life, given her looks. But we are all different, and I guess she wants to be appreciated for what she has on the inside. Instead of what she has on the outside," Rob moved slowly to the chair opposite Nick's desk as he spoke and took a seat. "What does Miss Gilbert need from me, Rob?" "Well she is Upgrading to our Flag Ship PC at her home office. It's obviously well out of most people's ability to set up, and she seems to have it firmly set in her mind that no one but you, is going to be able to set the system up properly," Rob was looking Nick squarely in the eye as he said this. "Well Rob it might be out of most people's ability to set the system up properly, that's true. However it's a walk in the park for even a first year Computer technician. I will do it of course, but I just hope you realize that will slow down my department with our investigation on the Thunderbolt issue," said Nick. "I realize that Nick and I really appreciate your understanding, helping me out with this. One of the harder parts of my job is keeping my key personnel happy so they can stay on the top of their game. I certainly will remember this sacrifice Nick, and you can rest assured I will take extra special care to help you anyway I can in the future. I like to reward my staff who go the extra mile for me," Rob added, as he slowly began to stand up and lean forward, with his arm outstretched to shake hands. Nick stood up smiling and shook Rob's hand as they said their goodbyes. Then Nick wondered what he had done to get the attention of the supermodel? Nick had known from as early as grade school that he wasn't a boy that would attract any girl's attention. He'd always been small, skinny and more interested in reading than playing sports like the other boys. He was certain that the reason for this attention from such a desirable coworker was of a purely business nature. However, it's nice to dream, he thought. Nick did a lot of dreaming in his own time. That's because when Nick was alone and in the privacy of his home, he had a special secret. When Nick got home from work each day, he'd usually follow a regime that removed the business man Nick, the Computer Geek, and put on Nikki the good time girl. Nikki had been born while Nick was at home in his teens and left alone to do the family laundry, one weekend while the rest of the family were all out for the day. His older sister had started buying grown up ladies underwear. But it was not like his mum's. These articles were so very silky and soft. So pretty and small, they fascinated Nick. Idle little hands do the devil's work, and before little Nick knew what he was doing he was in his room dressed in the satin pretty little nothings and furiously beating the small appendage between his legs as if everything was its fault and Nick needed to punish it. It would give him such a wonderful feeling at the end, when it spewed forth its token dribble, after having been wrestled between his clenched fist and the silky panties. That deposit of future possible little Nicks was simply the price he knew had to be paid. As he matured so did his relationship between his appendage and those pretty panties. He began to introduce close family members of the panties. Bras, camisoles, slips, skirts, short dresses, high heels, stockings, garter belts and sexy form fitting gowns were the immediate family. However,. As with all other families, it wasn't too long before distant relatives started showing up in Nick's secret life with those panties, in the form of jewelry, make up, and wigs. While Nick dearly loved to spend time with his secret extended family, while he was at university he kept them all in a hideout. It was only after Nick started working and could afford to move out on his own that he could freely invite them all to come and stay with him. This was when his Nikki came out and asserted herself as the lady of the house. During Nicks working career he found the internet a wonderful playground for Nikki and the family. Nikki found lots of kindred spirits all eager to share experiences and recipes. She had her own Blog and organized little outings for a very select group of kindred spirits. At work Nick got along with everyone he worked with. They all thought Nick was a bit of a loner and felt a bit sorry for him. His small stature and slightly effeminate looks were why his secretary Betty, who was older than Nick, thought it was her social duty to comb the office and an extended pool of friends to try and find a date for her boss. She looked on him as a surrogate son. He was certainly small enough and cute enough in her eyes. Nick secretly got a warm feeling from Betty's mothering attitude, and he basically let her run the office however she felt it should be run. This, Nick told himself, gave him more time to focus on getting the work done. He felt this was how a man showed his ability to delegate. After Ron had left, Nick buzzed Betty and asked her if she could contact Miss Gilbert's office and arrange a suitable time for the installation of the company's equipment. Also to get him the address and a contact phone number. Betty instantly had one hundred and one questions about this lady her sweet boss was going to visit. Betty of course knew the lady in question and was thrilled for Nick, that he was going to be spending some time with the most beautiful woman at the company, a woman who was still single, just like her boss. Later that day Nick was given the address and instructions to head over to Miss Gilbert's house as soon as he was able, as she was apparently already waiting for him. All of the equipment had been delivered the previous week. Nick told Betty he would probably be gone for at least a couple of days. Although the work wasn't technically difficult, it was time consuming due to its bulk, the enormous amount of adjustments that needed to be made during setup. As Nick drove over to Miss Gilbert's home he wondered why she was having such a large state-of-the-art computer with huge multiple screens set up in her home. This computer was really a geek's wet dream computer, and the last thing Miss Gilbert looked like was a geek. As Nick turned into the street he was amazed by the size of each front fence surrounding the house blocks. At a rough guess he surmised they must be half-acre house blocks. Well, Miss Gilbert sure had privacy, that was certain. When he turned into her driveway he was again surprised, he couldn't see the house at all. The drive snaked its way between tall pine trees on either side. He proceeded up the drive for what he guessed to be four or five hundred yards before it turned sharply into a courtyard with a fountain in the middle. On his right he saw that the drive continued on to a large garage that looked like it could accommodate at least ten cars. To his left there were very wide white marble steps that went up to a wall of glass. The house was completely finished with floor to roof glass. There was also water rippling down the walls from the roof. Not very much, just enough to obscure a view of whatever was on the other side of the glass. A small area in the middle of the wall did not have water flowing down it and he noticed a shiny very large chrome handle. Must be the front door, he surmised. Kathrine It had been a difficult week for the beautiful and intelligent young lady. She had been to another counseling session, which she considered a complete waste of her time. She could never and would never open up to anyone like that about the true nature of her relationship with her recently deceased parents. She was so indignant at the do gooders for creating such a fuss, that she ended up going to a counselor just to get them off her back. They had been unlucky enough to board an ill-fated flight earlier in the year and Kathrine was missing them both deeply. She needed all of her self-control to stay focused and continue the life plan that she and her mother had planned together years ago. Kathrine's mother was a dominant woman and had brought up her only child to follow in her footsteps. For Kathrine the example her mother had given her was one of pure female empowerment. Her mother was in fact a dominatrix and her Daddy was the most beautiful and kind Sissy that Kathrine had ever known. She adored them both and from very early on had eagerly spent as much time with them as she could. Her mother would often let Kathrine see to her Daddy's punishment in order to help her build confidence for when she would have her own Husband. Her mother had on many occasions sat down with Kathrine and carefully explained the reasons she should punish her Daddy. Daddy would also sit down with Kathrine and explain the reasons why he loved her mother so dearly and was pleased to see her enjoy the company of other men. There was one part of her parents' relationship that always stuck out in Kathrine's mind, the one she felt placed their love for each other above every other couple's Kathrine had ever known. That was dinner time, when her Mother would sit down at the dinner table with her, and her Daddy would take his place lying flat on the floor, with his face under her Mother's specially made chair. Her mother would then remove the diaphragm she had inserted in her pussy, and allow her daddy to receive the dinner that his Mistress had so considerately collected on his behalf from her daily bulls. She explained to Kathrine that one of the reasons they were so happily married was that they each gave the other what they most deeply and intimately needed. For Kathrine's mother it was a male who would assume the feminine role and give her a way of expressing her strong dominant nature. While for her daddy it was having a woman he could hold up on a pedestal and worship while expressing his submissive feminine nature. So she explained to Kathrine that they were both outcasts from main stream society but had found in each other a perfect complementing partner for life. Having been brought up this way, Kathrine did not look at men the same way her friends did. She loved having sex with both sexes just as her mother did. She also fully enjoyed big strong virile men plowing their hard man meat deep within her, just like her mummy did. But she too was of a strong dominant nature and found that those big strong virile men were really only good for one thing. When it came to spending time with someone for company, these men left her cold. She adored the sweet sissy ways of her daddy. How quickly he would jump to serve her and her mother, chatting about everything from hair styles and women's fashions to sexual techniques for sustained orgasms. Her daddy was like the closest of girlfriends. She fondly remembered his reassuring winks when she was a little concerned she might be hurting him while placing him in restraints, or paddling his bottom at the direction of her mother. She marveled at the discomfort he would welcome to please her and her mother. She realized early on in her upbringing that she needed to find a very special partner. Someone just like her dear daddy. She also realized that just like her mother, she was going to need to train her little princess when she found Him. Then while attending university she was sitting in the main cafeteria reading and pondering while just watching the other students coming and going, when she noticed something out of the ordinary. It was a boy, he was around her own slender build with blonde hair like hers, and he kind of reminded her of her dear daddy. She decided right away she would find out everything she could about this boy. She would tell her mother about him and ask her what she thought. Fortunately for Kathrine, while her daddy wasn't practicing his first love, worshiping her mother, he was a very successful international banker. The question of money never reared its head in their home life. So when Kathrine mentioned this promising boy she had seen at university to her mother, her mother's first reaction was to pick up the phone and call her personal private investigator. He was mostly used for checking out business associates and clients, but now and then she found it useful to use his services for more personal matters. Later that month Kathrine was given a folder by her mother containing every little detail about her mystery boy, right down to his dress size. She read every word the file contained. Twice. Her mother was in agreement with her, that he was indeed very promising and worth her time to pursue. The tricky part was going to be getting this little princess around to her way of thinking. She noticed in the file that he frequently went online to a favorite chat room that was linked to a cross dressing blog he would go to. She then decided she would try chatting with him, first under different nics, playing different characters, to see if she could draw him out. This ended up taking a few months. But well before her parents' fatal day, she had managed to share some wonderful times in the chat room with her mother and her little princess. She and her mother playing tag team on him, both using femme dom nics. He was naturally oblivious to the scheming that was already in full swing around him. During this early time her mother helped her form a strategy to execute. This was the plan Kathrine was still working on, her main focus since her parent's untimely death. In a way Kathrine now saw her molding of her little princess as a way of keeping her parents and their life style alive in her memories, and this helped to console her in this time of healing. The plan allowed some time before they would meet face to face for the first time. She needed to appear in his life as a figure to be worshipped from afar. Someone out of reach of someone such as himself. This would make any interest she might bestow on him later all the more powerful in its effect on his psyche. Her mother was the one who explained to Kathrine that the best way to accomplish this would be to work in the same company he works in, when he finds employment, but from the start to seriously outrank him. Then from his first focus on her, he would be looking at her the right way, up! Her dominance over him would be among his very first thoughts about her. He must only ever see her as unobtainable. Then with the use of the internet and the chat room, she could coax his mind in the right direction, patiently, day by day, manipulating his mind into not just accepting female superiority, but worshipping it. He must come to revere her first, before they met face to face, without realizing that that's what he was in fact doing. Then as she took him into her life as her life partner, he would always keep her on that high pedestal, even while watching other men's cocks sliding in and out of her body. Kathrine well-remembered her 17th birthday party. Her mother had spent a week making the preparations. It was an incredible day of pleasure and learning that culminated in her being laid comfortably on her big bed. Her mother was seated in a chair next to her in the role of director. Then one after another bodybuilders with cocks no less than eight inches but some as large as twelve would enter the room, mount Kathrine, pump until she climaxed, then release their load and leave. All-in-all there were ten men. After five however, she needed to empty herself, and this was where her daddy played his part, lying on the floor next to the bed at his wife's feet. Kathrine's mummy explained what to do. "Now baby just watch you slip your hand over your pussy before you swing your legs out of bed. Cup your hand firmly against your pussy. Then watch you don't step directly on your Sissy as you get out. Place one foot on either side of his head and with your hand still firmly in place, gently lower your pussy to his mouth. It's up to you how you feed your Sissy , you can just quickly remove your hand and let your sissy handle the flow with his mouth but I've found my Sissy is very eager, and I enjoy making him fight a bit for it. First by letting him only get what slips between my fingers, It lasts longer that way and its more fun watching him get all excited when some thicker more creamy bits slip out. Then after a while I like to tease him by taking my hand away and giving him a mouth full then digging my fingers between his lips and mine and stopping him." Her mommy laughed at that point. "But sweetie it's your birthday and he's your sissy to use today so just do whatever you find most enjoyable" she finished with. Kathrine squatted down over his face, facing her mummy for further coaching on how best to feed the Sissy his meal. She looked in her mother's eyes and gave a big smile as she felt her daddy's tongue flicking between her fingers and cleaning her as he went. Kathrine, felt wonderful that she could enjoy such intimate moments with her parents. She understood this sort of behavior was frowned on by the majority of society but she didn't care what other people thought, as long as her Mummy encouraged her. Her daddy did very well that day, and brought Kathrine off to a number of climaxes with that first load. She then had the next five men service her before trying a different way of feeding her Sissy that mummy borrowed her. Instead of holding it in with her hand, she wanted to watch her daddy Sissy climb on to the bed and get behind her. She kept her head on the bed in the doggie position as she lifted her pelvis high into the air and told him he was going to need to suck it out of her this time. She could feel his warm breath and his nose in her crotch diligently working away, flicking up and down the crack of her bottom. Every now and then she told him he needed to get his tongue deeper into her rosebud to massage her insides with its tip. Then if he did well she would reward him by letting him resume sucking at her pussy, as one climax after another washed over her. At one point she looked to see where mommy was, and saw she was fingering her pussy with her legs resting on the bed, watching all the action from her excellent vantage point. Ahhh yes Kathrine would always remember that birthday. Her mother made a point of insisting that Kathrine exercise her abdominal and pelvic muscles daily, by doing things like lifting pens sitting in a glass on the floor, grabbing hold of the pen with her pussy lips, using her vaginal muscles as she then stood up, pen still tight in her pussy. It was by doing things like this that Kathrine, could control all of the pleasure she and her lovers received during intercourse. Once a man had experienced sex with Kathrine, they were ruined for life with other women. Her power over men was formidable. Her mother's instructions and training combined with her natural beauty, made Kathrine a force to be reckoned with. As Kathrine looked at the monitor that showed the driveway camera, she was thinking about how long it had taken from the first time she saw Nickolas, her sweet soon to be Sissy slave. She thoughtfully pondered the steps she had planned out with her mother's help to get to this point. All of the training her mother and daddy had given her was now about to be put to the final test. Would she be able to convince Nicky to give himself completely to her as her Sissy sex slave and Cuckold life partner. Technically, she realized, the world would see him as her sissy husband. But in her mind she was really going to be the husband when they were married. At this point she suddenly burst into laughter as she realized she was thinking about marrying a man who at this point in time didn't know she already knew everything about him. In fact he would be thinking they were almost complete strangers. This was going to be so much fun, she giggled to herself, still eyeing the monitor. When the car finally did appear Kathrine's first thought she said out loud to herself, "Show time Folks". She began the walk from the security room to the front door, and reached the front door just as she saw Nick looking left and right of the door for a button to press. Of course there was none. Kathrine opened the door and welcomed Nick with a big warm smile. "Hello you must be Nick from work, don't worry looking for a door bell, my parents had this house custom built and deliberately didn't have a door bell fitted. They just hated interruptions and would always wait to welcome people they invited." "Oh hello Miss Gilbert, yes I am from the company, I hope you haven't been waiting too long?" Nick said trying not to stare at her beauty. "Come in, and please, just call me Kathrine," She said this while thinking at the same time, the title she would soon have him trained to address her with, would make the formality of Miss Gilbert pale by comparison. That thought made her welcoming smile even broader. Kathrine was wearing a long rose colored satin dress robe that was closed at the top tight up against her neck and all the way down to her knees, where it opened and allowed just a glimpse of her stocking-covered legs as she walked. "You're probably curious to know why I pulled some strings to have you come and fit this system". She said this as she turned to walk away from Nick and back deeper into the house, expecting Nick to come in and follow her. Which Nick did, with a quick hurried step, turning as he walked through the front doorway to close the door behind him. When he turned back to follow her she had quickly opened up a distance between them. Nick just couldn't help but stare at the interior of the house as she walked off. This place was out of this world, Nick thought. The ceilings were high and everything was white. It was difficult to see where the floor met the walls and where the walls met the ceiling. Nick couldn't make out any lines or fixtures. Not even lights in the ceiling. He wondered if there were any. Nick wanted to look closer but had to hurry to catch up with Kathrine. "Well, Rob explained that you have great confidence in my technical ability but none in my coworkers. I don't know why, Kathrine, as I don't believe I have done any work in front of you to date," Nick said still looking around in all directions with a look of bewilderment. "Come this way" Kathrine said as she led Nick into a room that he thought must be the lounge. Well at least it had a couch and coffee table in front of it, so that was enough to make that assumption. "Please have a seat while I get us something to drink. You must be thirsty after your drive here," she said. She didn't wait for him to reply and left the room. Nick walked over to the couch and sat down. He started studying everything in this room. It also had one wall that was completely made of glass and had water flowing slowly down its full length. He listened and noticed how quiet it was. There was not a sound, he could hear only his own breathing. There were some paintings on two of the walls, postmodernist impressionist was Nicks guess. He didn't recognize them. The couch was made of soft black leather and was very low and close to the floor for sitting. The rest of the furniture in the room was a little sparse. The coffee table was also very low and painted piano black. There was what looked like a wall unit of some kind, again black like the coffee table, but it had no handles or doors that Nick could see. It was relatively large, taking up half of one wall, and it was opposite the couch. Perhaps it held the entertainment system? Nick made up his mind not to be nosey and just wait for Kathrine to show him if it came up. Kathrine returned with two glasses in her hands and handed Nick one. He thanked her as she informed him it was pineapple juice. "Mmm my favorite" Nick said. "Really?" said Kathrine with a sly smile. "Wasn't that lucky?" She sat down next to Nick, so close she was actually, literally rubbing shoulders with Nick. "You know Rob never said how cute you were Nikki" Kathrine said as she faced Nick with her lips only inches from Nick's. Nick felt his face begin to burn and he knew he was seriously blushing. This just fuelled Kathrine's resolve. "Is everything alright Nikki?" Kathrine said sweetly pretending she didn't realize which name she was using. "Umm I think I should probably get started", said Nick as he made a move to get up. But Kathrine just placed her left hand on Nick's shoulder, firmly pushing him back down to the couch. "My, my Nikki, are you going to ignore my hospitality? I think I might be offended" she said with mock indignation. "Oh I'm sorry Miss Gilbert I I I mean Kathrine I didn't mean to offend you," Stuttered Nick. "Well Nicky I don't know...Hmmm are you really sorry?" It took great self- control on Kathrine's part not to burst out laughing at the very obvious discomfort she was inflicting on Nick now. Nick was in serious inner turmoil. This beautiful woman was seeming to throw herself at him and it frightened him so much he just wanted to run. Why he was reacting this way he had no idea, except that a little voice told him it might have something to do with the way she was addressing him. "Yes I am truly sorry Kathrine, you are a wonderful hostess, I don't know what got into me. I'm just a little nervous that's all," said Nick while looking into Kathrine's deep blue eyes. Kathrine let just a hint of a smile cross her lips as she lifted her left hand up and slowly inserted three fingers into Nick's hair, then began to run them ever so slowly back while she said " You know Nikki, I would love to believe you. But I seem to be having a difficult time doing that. I get the impression you don't like me," She was still focused on her fingers in his hair and spoke slowly in a soft voice almost absent mindedly. Nick's little appendage was fighting his slacks to get free, and he began squirming around in a vain attempt to relieve how awkward he felt. Desperate to convince this goddess she was wrong, he blurted out, "No Kathrine, it's not true, I think you're the most beautiful woman I've ever seen." Kathrine did smile now and quipped, still speaking softly, "Well I'm glad we established that, but how are you going to make it up to me? What are you going to do after hurting my feelings by your terrible behavior?" she teased. "I would do anything for you Kathrine, anything at all," Nick said without so much as a second thought. Ahhhh yes that's what Kathrine needed to hear. Giving poor naive Nick her puppy dog eyes, she said, "Well Nikki, why don't you finish your drink while I think about that," She said it with a very sly smile, her face still only inches from Nicks. As Nick brought the glass to his lips again he began to wonder why he felt so light-headed. Could it be the arousal of being so intimately close to this sexy beautiful woman? Or, could he be coming down with something? Kathrine casually glanced at her watch and wondered how much longer the tranquilizer in Nicks drink would need to take effect. She thought she could save a little time and effort now by leading him to where she physically wanted him before he lost consciousness. "Nikki Sweet Puffs, why don't I show you where you will be working while I consider what you can do to prove to me I am wrong about your not liking me," She said this with a soft smile as she stood up slowly and took his hand. Nick really wasn't feeling the best and then it hit him - the endearment Kathrine just used. "Oh my God," he thought, "that's the way Mistress in the chat room addresses me," The Mistress he had been secretly submitting to online for over two years. He had never seen her and would often wonder - when doubt clouded his mind - if she were even a real woman. Looking back down at Nick, Kathrine could see in his eyes that the wheels were turning after she'd used their online private room endearment. She felt a rush of power over him so strong in that moment, as their eyes bore deeply into each other's, that it made her pussy wet. She just smiled at him, holding his hand still without moving, savoring this very moment. She knew now his mind would be reeling. However, this feeling of power over him was so intoxicating she had to prolong it for all it was worth. "Come on, follow me, Nikki Sweet Puffs," She now firmly pulled him to his feet and began leading him to a doorway he had not been through yet. He followed her mutely, unable to string coherent thoughts together. Then as they passed through the doorway he noticed that this hallway was just like the foyer. His head was really starting to feel fuzzy now. "Kathrine, I'm not feeling all that well I think I need to sit back down," he said. SHE DIDN'T SAY ANYTHING BUT HELD HIS HAND FIRMLY AND PULLED HIM AS QUICKLY AS SHE DARED THROUGH TO THE ROOM SHE HAD PREPARED. NICK SAW A STRANGE LOOKING COUCH IN THE MIDDLE OF THE ROOM THEY ENTERED THAT HAD NO BACK ON IT. IT REMINDED HIM OF A MASSAGE BENCH. HE USED ALL THE EFFORT HE HAD LEFT TO REACH IT BEFORE EVERYTHING STARTED TO GO DARK.THE LAST THING HE HEARD WAS "THAT'S MISTRESS KATHRINE TO YOU FROM NOW ON SWEET PUFFS" End part one

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Chapter 7 - A new game Again awaking in the morning in a simple straitjacket, Masters control was now so strong that I considered a straitjacket simple! In Masters arms I felt a huge sign of relief that my evening was over but again I had to resolve myself to the fact that this was my life now. My body was screaming in pain, the torture inflicted on my gorgeous breasts was beyond what I had ever imagined. It must have been a sign of my diminishing mind and need to please master that...

2 years ago
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Sissy Slave Requirements

Minimum Sissy Slave Requirements:A SISSY GURL IS KEPT IN CHASTITY: A sissy must be ‘permanently’ locked into a chastity device at all times, (except during supervised cleaning), her orgasm’s denied and any discharges graciously granted will be 100% controlled by her key holder and under the proviso that the sissy will consume them. The sissy no longer has a penis; she has a “clitty” and will always refer to it as such, the “clitty” is for her Alpha owner to control and use as their...

3 years ago
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The Slave and the Sissy

She had always been very rough with him, the big woman, but this morning was exceptional, and different.  She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or had him lick her till she grunted out yet another orgasm, before serving him with cane or whip.  Now morning was here she face sat him; her...

4 years ago
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The Slave and the Sissy

She had always been very rough with him, the big woman, but this morning was exceptional, and different. She had come home late from her usual soiree with other local mistresses and had whipped him mercilessly for no apparent reason; she had woken him during the early hours several times, tormented him and had her arse licked while she applied her dildo or had him lick her till she grunted out yet another orgasm, before serving him with cane or whip. Now morning was here she face sat him;...

3 years ago
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Sissy fucksow slave Denise the three gifts from her Mistress

And talking about her, you can hear now a familiar sound. Yes, she’s coming because as a good sissy submissive you know the celestial / infernal sound of the High Heel shoes on the floor, so you open your eyes as in front of you some soft lights begin to turn on. You see her coming in a way you have never known before. Yes, she’s coming towards you, but OMG! She is absolutely naked now, except for those High Heel shoes you sometimes hate and sometimes love, but you still not surrender yourself...

2 years ago
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Masters Sissy Slave Chapter 3 Broken

Chapter 3 - Broken For the following days and weeks I settled into a routine of Masters design. With my resolve to comply with the commands of my Master and see out this month I surprisingly found satisfaction in the simplicity of being a slave and following orders. I had worked so hard to follow all of Masters rules and apart from a couple of unconscious misdemeanours, that Master accepted were not malicious I had found myself enjoying the life. I mean I would have preferred my...

4 years ago
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Masters Sissy Slave Chapter 1 The beginning

Master's Sissy slave by llatex39 The beginning "Welcome to you new life" Stirring slowly I opened my eyes to see my Doctor Marcus standing over me. I was at a loss... where was I? what had happened last night? I could remember having a couple of drinks after going to Marcus's house and then nothing. Everything felt off, my skin felt weird - feeling trapped and constrained, I tired to sit up but had no power left in my limbs. "Don't worry Jessica," Marcus said, "you'll get the...

2 years ago
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Celias journey to sissy slave

My first time with a guy, orally was a bit different than what usually happens with young teenage boys and their sexual experimentation, but not as much as it might seem. Growing up, next door to me was a pair of sisters, the youngest was 3 years older than me, which during this time in the story, I was 14 and she was 17 and her sister was 19. One summer day, we lost power in the neighborhood cause of a bad train wreck. Well, the sister's, their names were Cathy was the younger one and...

3 years ago
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Masters Sissy Slave Chapter 6 Penitence

Chapter 6 - Penitence Waking up in a latex straitjacket with masters arms around me in bed, I felt a huge amount of relief. Master was here to take care of me. Waking slowly I remembered the ordeal that had been my first full day as Masters slave. The warm embrace helped sooth and recover me but deep down I still had intense and mixed feelings about what had happened. Clearly a number of people had known me at that club, some were shocked at my transformation others clearly weren't. ...

4 years ago
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Sissy Boy Slave and His NEW Playmate Sadie

sharleesisterboyYes, Sadie, I am a 'Lil Slave Bitch' for My Big 'brother's Cock use, when He and His friends get in the Mood for Young Sissy Boy meat to strip and abuse on the livingroom floor, inside the 'Big House'! I'm f******n and have been His Secret Sissy, Piss-Whore Slave since He traded for me five years ago when I was Nine! He KEEPS Me Locked Up in a rusty, smelly old trailer, parked inside a dark, Old Red Barn. I'm Locked up inside and I sleep on an old, Urine Smelling, Stained...

4 years ago
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Sissy Slave

Joanne, my wife, has for many years insisted that I wear lingerie and girly things under my male clothes when at work as part of my sissy training. At home I am a sissy slave.“Sally” she said “Today we are going to make you feel more aware of the pretty things you wear”. After years of taking hormones my breasts are a nice 38C with dark brown shades round my nipples and Joanne had arranged for me have my balls and sac removed when we went to Thailand one year. Despite this and though my cock...

3 years ago
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Sissy Slave To Master Kamal 8211 Part 2

Hello Masters , Thanks for your comments , Small recap – I’m arvind , who was sexually excited after reading feminine , boy to girl transformation ,BDSM , Sissy stories . To fantasize he found guy called kamal on chat . Kamal treated me as sex slave and kamal’s girlfriend came up with a idea to transform me to completely a girl . Here part 2 starts , As per my masters and mistress wish accepted the transformation , they told me sign a agreement , it has few conditions .. they’re , 1 . I...

Gay Male
4 years ago
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Sissy Slave To My Master Kamal

Hello master and mistress , I am your sissy slave Arvind alias Ananya . I am novice in story writing so please ignore my grammatical mistakes . I am working in a private firm , I am a regular visitor ISS . I really fond of gay story and submissive and feminine character story . Read many stories related to above topics and loved to be sissy sex slave to any man (masters) and women (mistress) . Let me come to the story , due to this interest I started chatting with guys to be my master and treat...

Gay Male
1 year ago
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The Slave and the Sissy part Four

Pepper and I knelt on the silky sheets of the bed and studied each-other in disbelief; our cocks rigid and ready for relief. I took her sweet sissy cock in hand as I sniffed and licked at her face and neck; her skin as white and silky as the sheets. She thrust her slippery little sissy cock back and forth between my fingers as I teased her glistening little pink bell-end. Pepper panted with anticipation as she unhitched her crop top; her sweet little breasts stood firm and inviting, my cock...

2 years ago
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The Slave and the Sissy Part Eight

Slave kissed Pepper’s pretty face to reassure her before they were both shackled and then gagged, and sat on a prominent open seat on Ayesha’s carriage, their hands bound in front of them; Ayesha loved to display her power and ownership of slaves, and would always ensure other people were made aware of it, even if the chattels were only hers to borrow. Slaves cock was in an erotic quandary as he felt the closeness of his soft sissy; bound and submissive and thinking only of how she could...

2 years ago
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The Slave the Slut and the Sissy

John was on his way to a conference, and had been driving North for at least four hours. The rain was pouring down on his windscreen as he continually wiped his eyes. 'I've got to find somewhere to stay', he thought to himself. After about ten minutes he came to the next exit on the motor-way. He found himself hopelessly lost in the dark countryside. 'Yess!' John had just discovered the sign for a bed and breakfast. He decided that staying the night there then getting his...

3 years ago
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Woman Turns Boyfriend Into A Sissy Slave

I actually began this with my boyfriend during our junior year in college. I became interested in feminization, and later sissification because my older sister’s husband is a doctor who has done some work with transsexuals. I began reading books and gathering information on websites and got started by crushing up Feminique and Triple Strength Mammary and putting them in Mark’s food and drinks without his knowing. Mark had a body I knew would convert with relative ease, average weight and...

3 years ago
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The Slave and the Sissy Part Seven

Honey was viewed like a new toy by her new master’s people as she was led whimpering to the ominous looking padded pole, the males jostled to fondle her soft white bottom and rubbed their erect cocks against her sweet little body at every opportunity; the womenfolk smiled with eager anticipation at the prospect of seeing a whipping; the sissies looked on with blank faces, having tasted the whip before. The males at the front howled with wicked derisory laughter as they viewed Honey’s little...

4 years ago
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Our Sissy Slave 2

Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that. A hard fucking does wonders for a sissy's attitude. You moved in a week later, and I knew you were ready for the next step. We...

3 years ago
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Sissy slave to my house hold servant

Sissy slave to my house hold servant.       It’s all gone with in a year, coming back to start point? I am weight 51kg comparing to my height 5.11 inch you can assume my week personality. I am working with software programmer I am earning 5 digit salaries per month; with my experience in work area I am expert in web programming and hacking websites database. I have my own flat, car every thing more for a bachelor. Sorry I forget to say my where I am from- I am from India, I am single in my flat...

4 years ago
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Maid to Slave

Maid to SlavebyWildfire427©“Come here, slave, and light my cigarette.”I move over to the girl and do as I’m told.“And get us some more beer. This party is just getting started. Right guys?”Yes it was getting started. Visions of uncertainty filled my head. However, at the same time, my pussy was throbbing with excitement. I bring back the beers and deliver one to my husband, Tom, my son, Mitch, and my son’s new girlfriend, Alicia. I had become accustomed to serving my husband. I had been doing...

3 years ago
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Masters Sissy Slave Chapter 9 Reward

Reward The next morning I woke up in my bondage jacket with Masters gently pumping in and out of me. After a slow but loving morning fuck Master came inside me and let me get ready for the day. As I was walking out of the room Master told me what I had been waiting for. "My Jessica, your performance was fantastic yesterday and you have earned your reward. I will allow you to orgasm this evening during our training session. Now go get that sexy ass ready for the day." My heart...

3 years ago
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Two Mistress Dominated Sissy Slave

From the last story I got good reviews and many interested mistresses contacted via mail. Below is one special story for slave lovers. I got a mail from one of the mistress after reading my story. She mailed me asking that “can I become her slave for 2 day”. I saw that mail next day, I replied for that mail saying “yes mistress”. After that next day again I got a reply about asking my details, I sent all my details. After that she asked me for a contact number. I sent her my contact...

2 years ago
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Sissy slaveboy gets trapped blackmailed Pt 1

I had been a submissive with ever more disgusting fantasises for several years now and had acted out a fair few of them over that time.I was a manly, muscular lad who everyone looked up to and would think was the textbook "normal man".I held a professional job, steady girlfriend and a good standard of living, to the outside world, the perfect existence.Behind closed doors i had harboured a strong, submissive streak which i could simply never satisfy and a desire to be controlled and humiliated...

4 years ago
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My Girlfriend madd Me a Sissy Part3

Here's the 3rd part of my story, I hope I didn't make you guys wait toolong. Hope you enjoy, its best read one handed ;-)My Girlfriend Made Me a Sissy - Part 3-------------------------------------------------I lay on Jess' bed waiting for her and wondering what would happen forages. She was in another room getting ready for her new lover, I wasalready dressed up. Pale blue, see through panties and matching bra, ashort black skirt and a blue vest top. With my make up done to show off mypretty...

3 years ago
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Sissy slave weekend part 1

Weekend is over, but what a weekend! I’d agreed to be a sissy slave for a friend of mine, her name is Candy. I’d spent 24 hrs getting ready, full body wax, painting my nails, buying sexy lingerie and heels for the occasion, I’d never been a slave before, I would be at the mercy of Candy all weekend.I arrived at Candy’s and she was smoking hot as always, she had a perfect figure, standing 6’5 with 36” legs, wearing a red basque, black stockings and red heels. She immediately put a collar and...

4 years ago
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My girlfriend made a sissypart1

Hey guys this is my first story ....hope you all like it ...When I was 18, in spite of my shyness and not being in anyway incrediblyattractive, I somehow landed myself a girlfriend 2 years older than me. Iwas quite short for a boy then, around 5'7 and very slim having not yetdeveloped much muscle. I had shoulder length brown hair and bright greeneyes and I simply couldn't believe my luck in getting this girl. She wascalled Jess, a beautiful redhead with a body to die for and an appetite forsex...

3 years ago
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How I Became a Sissy Slave Chapter 1

This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a few months now I've been exploring my feminine side. Actually, I haven't been "exploring" so much as diving right in. After a bad breakup I had last year with my ex girlfriend I went on a self exploration binge and discovered I was pansexual. Shortly after coming out, I began to discover more and more about myself, such as how fascinated I was by...

3 years ago
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Sissy slaveboy get trapped blackmailed Pt 3

It was a tough morning....I got up and walked around in a bit of a daze wondering what i had done and what would happen next.I hoped the whole scenario was a lesson for me concocted by Empress and Saskian to mind fuck me and make me realise how stupid i had been.I made tea, popped in some toast and sat uncomfortablly to watch something i can't recall on TV.About 11.15am my mobile shook violently on the table next to the sofa and beeped loudly jolting me to my senses and scaring me so my...

3 years ago
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Virgin Boy Turned Into Slave With A Sissy

Hello everyone ….. Vaibhav from Delhi……First of all huge fan of iss been reading erotic stories for 2-3 years…Any lady or girl, married or divorced basically any female who wants to make me their slave or any other fantasy can mail me on all the emails will be replied….I am decent boy, well mannered, educated, neat and clean and obedient slave…I love being dominated by someone and moreover if the female is much older than me and turns into a full super dominating bitch… The story I am going to...

3 years ago
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Turned into sissy cuckold slave

Glen always got k**ded about how young he looked. Even on his wedding day, three months ago, someone had called him 'the baby-faced bridegroom'. He took it all good-naturedly. After all, he was quite short and slender, and really did appear to be in his teens. At 21 he still got carded in liquor stores. He didn't get carded in bars because he never drank there. Even the neighborhood place, which was completely tame, seemed too rough to him. Maybe that was why he felt so comfortable with Leesy,...

2 years ago
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Sissy slaveboy gets trapped blackmailed Pt 2

When Empress had finished taking pics and videos and collecting enough evidence to ruin an army, let alone one guy she sat at her laptop and downloaded all the images onto her hotmail account and sent a copy to Mistress Saskia who was sat with her."There sissy, now they are safe in our hands and there is NO WAY you can get to them or more importantly, get rid of them. You are one fucked little whore boi"Her words echoed in my head... she was right... i was screwed over...Empress rose to her...

1 year ago
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Sissy Puppy Fifi Part2

Chapter 2 I tried as best as I could to get comfortable curled up in the corner of the room. At first I kept squashing my tail which either caused the vibrations to start or pushed the plug further inside. I had eventually worked out the best position to lie in when Mistress appeared. "Time for bed Fifi," she said as she attached the pink lead to my collar. I was then led through the house and up to her bedroom. This was a strange feeling to enter her bedroom not in my usual maid's...

2 years ago
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The Slave and the Sissy Part Two

Ella smiled with wicked anticipation as she ordered me to sniff her pussy but not lick, not yet. She teased her moist and shiny labia with a long slender finger, bringing the scent of her arousal to its aromatic maximum, then touched my nose and had me lick her finger. I ached to service her, and for release from my cage. My cock hurt, it was so tight in its trap, and dribbled sticky pre-cum much to my new Mistress’s delight. She giggled wickedly.“I’m so pleased to be able to have you at my...

4 years ago
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DaddyDorsquos Sissy Slave

Arrived at Master’s house , as instructed at 10.30am wearing black lacy lingerie under my normal clothes and waited nervously and excited for him to answer the door. Master soon appeared and showed me into a darkened room. Sitting, he watched as I stripped down to my undies and paraded before him like the Sissy I am, desperately seeking his approval. Knowing he would not be pleased if he saw my small girly clit getting hard inside my panties. Standing up, Master told me to pull my panties...

3 years ago
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SISSY DANI PART3

CHAPTER THREEMistress Jennifer and Mistress Susan's plans to create an entire"harem" of transformed men and boys continued apace. The lure ofTeasing Tammy (the transformation name of Susan's teen-agedbrother Tommy) proved quite effective. Each of the young men (theyoungest just 14, the oldest 22) the little tease brought back tothe home we all now shared was turned into a different kind offeminized sex-toy, all designed to please the Mistresses andtheir dominant friends.The little...

2 years ago
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Blackmailed Sissy Whore Part one

Blackmailed Sissy Whore Part 1 It's amazing how quickly life can spiral out of control. One moment your enjoying what you think is just a little harmless indulgence in your submissive crossdressing fantasy life when, out of nowhere, your life is turned upside down. It was a Saturday morning in February, 2020. I was a single guy, living the dream. I had a really good job and was living in a 2 bedroom apartment in an upscale complex a few miles South of Pittsburgh. I had transformed...

3 years ago
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Big African Cocks Banging Sissy Slave8217s Ass

Hi all ISS readers. This is bustybitch. This is my real life story and please leave your comments at my email. I provide services to both gay males and straight women and also open to a relationship. The story begins. I came into the business of gay male due to my school professors who used to bang me during my school days. I was their personal sissy slave and I was given rough treatment from them. Anyway, soon I came to realise that there were many and men out there who wanted to fuck...

Gay Male
2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

3 years ago
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Our Sissy Slave

Let me remind you how you came to be in this situation before you refuse. I’ve been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little...

3 years ago
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Our Sissy Slave 1

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my...

4 years ago
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Our Sissy Slave

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little...

Crossdressing
4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

2 years ago
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Andrew The Unsuspecting Sissy Part IV

ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

4 years ago
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My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

2 years ago
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Mommys Dirty Sissy Slut part 1

Mommy's Dirty Sissy Slut part 1 by dirteesissy "Answer the door for me, Brother Dearest and make sure to greet my guests Properly!" I headed to the front door, shame filling my heart, as I tottered on 5" stiletto heels. Not the usual footwear for a 20 year old man, but I couldn't have looked less like a male dressed as I was. Chapter 1. Last week my sister, Alicia, caught me masturbating to stories on a website called Fictionmania. In most cases this would have been...

1 year ago
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Trucker Daddy gets himself a New Sissy part 1 and 2

TRUCKER DADDY GETS HIMSELF A SISSY BY DEEWET It could easily be the lowest point in Denny's 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. 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 Truck Stop. He almost jumped out of his skin when someone knocked on the window. Denny...

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