Her Sissy free porn video

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Her Sissy by Tiffany Scott 96' At the time I had no idea what my wife had planned. We had been married for three years and I thought we were both happy, but Kelly was getting itchy and restless. It wasn't that she was tired of me or the life we had created for oursleves, it was more that she wanted to be in control. That she knew what she wanted almost made it worse, because she didn't know how to go about getting it. Oh sure there were times when she felt the way she wanted to feel. She felt that kind of power and control when she would tease me so that I was almost ready to come, then she would make me beg her to let me fuck her. She had been thinking about those times when she had taken the dominate role and after a bit of thinking she started to realize just how easy it was for her to get me to submit to her. Kelly was a bright girl and she gave the whole thing quite a bit of mulling over. In fact she had even conducted a couple of experiments over the last two weeks. Once she refused to let me come until I had tounged her to numerous climax's. Another time she had pretended to be upset with me and after telling me over and over how bad I had been she got me to agree to letting her spank me. She couldn't think of a better demonstration of my submissiveness then to be bending over while I held my dress or skirt up around my hips so that she could spank my now defenseless ass cheeks, unless it was what she was planning on doing to me. She hoped that forcing me to listen as she told me how much she enjoyed punishing me would make me eager to let her do it to me any time she wanted. "Yes, I think that out of all of the things we have done together, I enjoyed spanking you ilke a naughty little girl more then anything else!" She told me. She smerked when I told her that I was glad that she enjoyed it. "Any time I can be part of something that you enjoyed doing I feel like I've done something nice for you." I told her, then I added, "If there's anything else that you think you would enjoy doing don't hesitate to try it. Just go ahead and tell me what you want me to do." "Really?" she asked, sounding as if she didn't believe me. "You just go ahead and tell me what you want me to do and I'll do it." I told her. She smiled and then told me that she wanted me to be her slave so that I HAD to do what she told me to do. "Then consider me your slave." I told her. "And I'll just assume that I have to comply with anything you want of me." She looked at me for a moment, then she ordered me to spread my legs so that my balls were completely accessable for her. I swallowed hard and then slowly moved my legs apart until they formed a wide Vee. She nodded as she slid her hand up between my upper thighs. "I love to think that they are hanging like they are and just waiting for me to decide what I want to do to them." She told me. "They are." I said. "You own my balls as well as everything else if I'm your slave." I told her. "That's right." She said with a smile. "And that would mean that I had a perfect right to do anything I wanted to them. Anything at all!" She closed her fingers around the two small nuggets. "What I want to do to my balls is make them hurt!" She said wickedly. She then crushed them aginst each other as she made her fingers form into a fist. I doubled up and groaned as my tummy was gripped by strong cramps. "Oh yes. I can tell that they hurt." She gasped as she squeezed them even tighter. My hands pressed into my tummy as I fought to catch my breath. "Spread your legs wider slave, as wide as you can!" She ordered. I heard her laugh when I opened my legs as wide as they could go. "Yes, now I can do anything I want to them." She said. "Even smash them under one of my knee's!" She added as she slid one leg up between mine. She released her grip, then raised up slightgly. When she lowered herself down I felt her hard knee start to flatten them under it. Once again I was doubled up from the way she was abusing my balls. "God, they feel as if they just flattened right out like squashed pancakes." She sqealed, then she lifted off of them. "If your my slave and I own your body, then I also own your asshole!" She exclaimed with a chuckle. But all and all she still wasn't sure how to go about doing what she thought she wanted to do. That is until my birthday started to get close. She had purchased a new monitor for my computer and she decided to hide it in the garage. There were a number of boxes of old paperwork and such and she felt that one more box wouldn't be noticed. The Friday before my birthday she got home several hours before me and she went out with the idea of moving things around so that she could stash her present in an inconspicuious spot. Most of the things were covered with dust and such and she quickly got fed up with trying to make it look like nothing had been disturbed. Finally she had had it and shoved several boxes to one side so there would be room for hers, but when they landed on the garage floor she was suprised by what spilled out. From her perch on the ladder she could clearly see all kinds of womens clothing. After a closer inspection she knew that these things weren't just a bunch of old discarded garments. Some of the blouses and other pieces were up to date styles. In fact she found a slip that she knew was part of Vanity Fairs newest line. With a growing curiousity she looked through the two boxes of lingerie, dresses, skirts and blouses. She even found a fair number of almost new high-heels in the second box along with a very complete collection of make-up. She was still a little confused when she picked up the small square booklet, but her confusion didn't stay with her very long as she glanced at the photographs that were inside. I had been crossdressing since the age of 12 or so and although I had tried to stop, I found that I couldn't. I had never told her about it and dressed up only when she was away. Over the years there had been some pictures friends had taken of me when I was completely dressed and made-up. She was not only suprised to learn about this part of me, but she was also suprised to see that I made a very good looking woman. As she glanced at the photo's a smile began to appear on her face, a smile that kept growing bigger and bigger. After putting the boxes back like they were she put the computer monitor in her car so she could return it. She had a better idea about what she should get me for my birthday then that. That weekend she went out of her way to be a tease. She would flash me her fanny and more of her breasts then she usually exposed and at night she would eagerly engage in fourplay, but we didn't seem to ever get around to having sex. She wanted me to be as fustrated and horny as she could make me when my birthday came. The same thing continued to happen that Monday and Tuesday and by Wednesday morning I had an almost permanent erection. I was just finishing my cup of coffee before going to work when she came into the kitchen and informed me that she had called my work and told them that I was sick. "In fact." She said gleefully. "I told them that you probably wouldn't be in until next week." Now it was my turn to be suprised as she took my hands and pulled to my feet. She led me into the spare bedroom, then told me take off all of my clothes. "I bought you several new outfits for your birthday." She said. Her playful attitude was contagious and I was starting to have a good time just getting undressed. She took each piece as I removed it, including my shoes and my watch. She told me to wait where I was, then disappeared through the doorway. I didn't know what to think when she returned empty handed, but she didn't give me much time to think about it because she stood right in front of me and started to take off her clothes as well. After slipping off her high heels she slipped her hands under her dress and skillfully pushed her pantyhose down off of her legs. She left them laying on the floor by her feet as she did the same with the pair of brightly flowered panties she was wearing. Only instead of letting them fall to the floor she made sure that they hadn't goten turned inside out and then she held them out in my direction. "I thought you might like to wear some of my things!" She said knowingly, then she added. "In fact I know that you would like to wear them!" She stared at me while she continued to hold her panties out for me to take. Inside I was almost out of control at the prospect of her dressing me up in her feminine garments, but I tried not to let it show. "I don't understand." I said as I took her panties into my hand. She planted her hands on her hips, then narrowed her brow. "Don't you give me any of that crap!" She said sternly. "I know all about you and I know that your nothing but a little sissy at heart." She swung her hips back and forth in an exagerated feminine movement. "And I also know all about your dressing up in girls clothes!" She said matter of factly. This caused me to almost go into shock and I stood and stared at her, not saying a word. "Now, you be a good girl and do what I tell you to do so I don't have to punish you!" She said. In a stern voice she outright ordered me into her panties. "Now put those panties on right now!" She stamped her foot just to make sure I knew she was serious. She wanted to jump with excitment when she saw me hold her panties open and then step into them, but she remained like she was as I pulled them up my legs and passed my hips. As soon as I had done that she unzipped her dress far enough that she could pull her arms free. "After you put on your bra your going to go into the bathroom and shave all that hair off of your legs!" She said as she unfastened the clasp so that the lace and satin bra slid down her arms. Just like she had done with her panties she held it out. I was still dazed as I gingerly took it from her. I pulled it around me and hooked it together, then pulled the straps up onto my sholders. She stepped closer to me and started to adjust the straps so it fit me. "I noticed you didn't have any trouble getting it fastened closed!" She said in a teasing voice. "You must have had plenty of practice." She added. Once she was satisfied with how she had adjusted the straps she pointed toward the bathroom. "Now go shave off all that ugly hair." She ordered, then she said. "Young ladies don't have body hair sprouting out all over like that!" She knew that she had made the correct judgement about me when she saw me start for the bathroom like she had ordered. In truth she didn't know how right she was because I became very submissive when I was dressed. Fifteen minutes later I was standing in front of her while she examined me. I had shaved my legs like she said, but I also shaved my chest, arms, armpits and had shaved around my now small triangular pubic area. "Very good!" She said after looking me over. "Your looking more feminine already!" She said in an obvious attempt to embarrass me and when she saw that she had made me blush her confidence doubled. "Go pick up the nylons I was wearing and put them on next!" She said with a nod. I didn't waste any time complying and after my legs were encased in her nylons she made me put on her high heels. In just a couple of minutes I was standing in front of her again. She let me stand like that for a little bit as she cupped and carressed her firm naked breasts. "Hmm. I like telling you what to do." She coo'd in a sexy voice. "It makes my nipples hard." She added. After a bit she lowered her hands to her sides and then lifed her dress a couple of inches so the lacy hem of her slip peeked out from under it. "Do you like my pretty slip sissy?" She asked, using that teasing tone of voice again. I told her that I liked it very much. "You want to wear it don't you panty-waist?" She taunted. Again I told her that she was correct. Hearing this she dropped her dress down so the slip was no longer exposed. "Then beg me to let you wear my slip sissy." She told me. "I want to hear just how much you want to wear it!" I slowly got onto my knees so she was towering over me. "Please Kelly let me wear your slip." I begged. "I love slips and I've never worn one that had been worn by you first." I pulled my panties up so that my cock was clearly visable under the front panel. I had been slowly getting harder and harder and now it was pretty close to being fully erect. "Just look at how hard my cock is from me just thinking a about wearing your pretty slip. Please let me put it on and I promise to do whatever you say. Please!" I begged. She stood over me smiling for a little while, then she nodded. "Ok, you may take it off of me and put it on sissy." She said, with a snicker. I gently reached up under her dress and carefully pulled her slip down her legs and then held it while she stepped out of it. Once she had I eagerly slipped my feet into the waistband and then pulled it up into place. The lacy hem came to just above mid-thigh. "Oh you look so sexy in my bra, nylons, panties and slip!" She said softly. "So sexy you make me wet. My little sissy makes my pussy wet when he does what I tell him to do!" She said in an athoritative voice. "I'm glad you think I'm a sexy." I said meekly, then added. "And I love it when you tell me what to do." She smiled when she heard me say that. "Good." she told me. "Because from now on I'm going to be telling you exactly what to do. Understand?" She asked. I lowered my head and then told her that I understood. She pushed her dress down so it fell in a circular ring around her feet. Daintily she stepped out of the center of it. She told me to pull it up into place, but added that I shouldn't zip it closed just yet. I worked the dress up over my hips, I had to tuck my slip back down afterward, then held it tightly around my middle. Kelly had busied herself with something in a box, but now she turned so she was facing me again. "These are what I got you for your birthday sissy!" She said, holding out a pair of silicon breast forms. They were so realistic that they jiggled like jello whenever she moved her hands. I felt them for a minute as I thanked her and after she handed them to me she pored a thick layer of super-glue on the back of each one. "You know what I want you to do." She said as she snickered. "I want you to push those breasts into place so they will be permanently glued to your chest." She reached out and pulled the straps of my bra down off of my sholders, then pushed the satin and lace cups so they were forced a couple of inches lower then they would normaly be. "Come on sissy." She ordered sternly. "Glue those titties to your chest. I know you want to!" I slowly raised both breast forms up toward my chest. "That's a good girl." Kelly said to urge me on. When they were about an inch away from where my own breasts would be, if I had any, Kelly placed her spread hands on the nipple side of each one. With increasing pressure she pushed them closer and closer until they were being firmly crushed aginst me. It only took a second for the super-glue to set. She pulled my hands away along with hers. I felt the expensive silicon breasts pull at my chest as they were allowed to hang freely on thier own. She began to knead them with her fingers. "I don't know how you would ever get them to come off." She said happily. "But that's ok, because this is how I want you to look." She ordered me to pull my bra back up and then gave me permission to zip up my dress. Once it was securly fastened closed Kelly stepped back and looked me over. She was now naked and I was wearing what she had been wearing just a short time ago. She spread her feet to about sholder width. "I'm going to put make-up on you because I want to make you into as much of a woman as I can. But now while your still obviously nothing more then a sissyfied male I want to watch you eat my pussy." She said forcing me to my knee's. "I can always remember what you looked like right now, because your never going to look this masculine again!" She added as she pulled my face tightly aginst her wet crotch. It only took a minute or so before she was grinding her pussy into my face. She continued to hump me like that through two climax's, then she pushed me away. "Go put on your make-up sissy so that there is nothing to remind me that you were once a male." She yelled. "I don't want to think of you in any way execpt that you are a woman." Without uttering a sound I went into the bathroom and made my face up so that the illusion of me being female was complete. Before going back into the bedroom I teased and brushed my hair into a feminine style. I stepped in front of her and curtsied. "Thank you for making me into a female." I told her. "What can I do to repay you?" I asked from by still bowed position. Kelly snickered and then pointed toward the foot of the bed. "You can bend over that footboard and let me be the first to use you like a woman would be used." She said. I rose and then bent over the footboard. The upper edge hit me right at my hips. "Get that dress out of my way and lower your panties bitch!" She ordered. I pulled my dress and slip up onto my back and then lowered my panties to the tops of my thighs. Seconds later I gasped when I felt a blunt object press against my tiny hole. I snuck a peek behind me and saw that she was wearing a strap-on dildo. "Oh your so small compaired to my big cock." She teased. "Are you sure you want me to take your virginity bitch?" She jokingly asked. "Please. Make me feel like a real woman." I told her. "Take me, use me." She didn't hesitate at all. She thrust her hips forward so that the head of her thick cock was driven right past my virgin opening. The pain was so intense my legs gave out, allowing all my weight to fall onto the footboard as I shreaked loudly. "You already sound like a woman!" SHe snarled as she thrust her pelvis forward a second time. Again I cried out from the pain and I almost passed out. Gasping several deep breaths I started to beg her to stay where she was until I got used to having her cock inside me. Her response was to ram her hips forward a third time. She kept applying more pressure until her hips were pressing firmly into my ass cheeks. "You took all of me cunt!" She rudely told me. "I love the way you look bent over like you are and with my cock buried as deep as it can go into your pussy!" I felt her grab my hips with her hands. "Now I'm going to show you what it feels like when you get a good hard fucking!" I was gasping and pleading with her to be more gentle as she moved her hips away from me so her cock was withdrawn from my tummy. But all of that stopped when she slammed it back into me, sinking all the way in with the one thrust. My legs were convulsing and my inner thighs felt as if they had been slashed with a sharp knife, but the stabbing, searing pain flooding out from my violated hole into my groin and cock was all I really felt. Several more times she plowed into me like that, which left me laying under her like a limp rag. I was slipping in and out of reality as she started to steadily pump her cock in and out of my once virgin pussy. I regained my sense's and was greated by the still painful sensation of her rythmic fucking. "Oh you take it good bitch!" She moaned. "Your so nice and tight, just the way I like them." She added. I felt her sink all the way into me and then hesitate for a moment, but then she picked right back up with the same ferious tempo. Several more times she hesitated like she did before. I was still finding it hard to move my legs and I moaned when I felt her take my cock into her hand. She bent it back between my thighs and then pulled my panties back up where they belonged so that the crotchband kept it like that. I could only gasp when she began to use both hands to stroke along the narrow strip of my panties that passed between my legs. She knew how to make the smooth nylon move over my imprisoned cock so that in less then sixty seconds I was almost ready to squirt my come right into my own panties. She sensed how close I was and she started to give my swollen cockhead a good working over. "Come on bitch!" She yelled. "Come in your panties for me!" She forced the head of my cock down between my cheeks. "Show me how much of a slut you really are cunt!" She shouted. A couple of strokes later she began to spank my ass cheeks with her open hand right through my panties. "I ordered you to come you little slut!" She said swatting me even harder then she had been. She wrapped her fingers around my shaft as far as my panties would allow, then she started stroking me from the front of my panites to back over the head. She saw my inner thighs tense up right before my hot sticky fluid started to shoot out of my cock. That gave her time to slip one hand under the waistband and shove her fingers in front of my cock. This allowed her to catch every squirt on her fingers, which she proptly shoved into my well fucked hole. In this manor she managed to force my pussy to be filled with my own sticky sperm. "Oh sissy!" She gasped. "I got hot thinking about your own come being forced into your pussy!" She said as she pulled my panties back down to my thighs. "So I'm going to have to fuck you again!" She said with a laugh. "Oh god, you'll kill me!" I cried out meekly, but I was suprised at how easily she sank into me. "Your come makes a good lubrication bitch, just like all women's pussy's are suppost to do." This time I actually felt myself pushing back to meet her forward thrusts. "Oh Kelly, fuck me." I begged. "Fuck my pussy good, fuck my pussy hard!" I gasped. "You can count on it slut!" She gleefully told me. "You can count on it."

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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...

2 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...

3 years ago
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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 attracted to...

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...

1 year 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...

1 year 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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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...

1 year 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...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

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