Forever Her Sissy - Chapter 2 free porn video

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This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 2 (By Purse Sissy) The drive home was uneventful and quiet, when we arrived I carried her bag in as usual and Karen went straight to the bathroom leaving a trail of clothes, shoes, and panty hose in her wake on the way to the bathtub. I heard the water turn on as I was gathering her things to take to the laundry room. Still holding her bag I began straightening up the kitchen. I had way too much nervous energy to settle down and rest. I heard her calling my name from the master bath so I ran quickly to her. "Oh honey, did you pick up my clothes that I left on the floor?" she asked, while testing the temperature of the water with her toe. "Yes ma'am, I took them to the laundry room." "Such a sweet sissy, be a dear and run to the hamper and bring me the panties that I wore tonight if you don't mind." I quickly went back to the laundry room and dug into the basket and retrieved her panties. They were a pink color with a pretty floral appliqu? design of lace at the front and a little bow at the waistband. They felt so silky and smooth in my hands, feeling a little guilty I took a quick sniff and gave the little cotton crotch panel a quick kiss before running back to the bathroom. She was slipping into the sudsy water as I entered the bathroom giving me just a quick peek of her temple surrounded by carefully manicured hair. Karen's body never failed to take my breath away, I was sorry that she had put bubble bath in the tub, the thick layer of suds was obscuring her beauty. Her voice snapped me out of my thoughts. "Take off your clothes honey" she said, sliding deeper into the warm soapy water, "I want you to put on those panties. I think that a sissy should wear panties, not boxers. Don't you agree?" "Yes ma'am" I stammered and began to remove my kakis pants and shirt. Sliding her panties up my legs was insanely sensual; they were so silky and smooth. I had to lift the waistband over my very erect dick, though in truth it wasn't that big, even when hard and it actually fit in her panties fairly well, just a little tent in the front poking out the lacy fabric right below the bow on the waist band. I stood before her, wearing her worn panties and still holding her purse over my shoulder. After her threat tonight there was no way I was going to put it down without her permission. "Kneel," she said, "and hand me my phone.." I knelt on the towel by the side of the tub and pulled her phone from her purse, carefully handing it to her, not wanting it to fall in the water. She lifted bar of soap from underneath the water and began to wash her arms but quickly stopped and sighed. "I am so tired, I just want to relax, and the water feels so good." I started to answer her but she put her finger to her lip and in a reprimanding way shushed me. "Open your mouth sissy," she said. When I did she placed the pink Oil of Olay beauty bar in my mouth. "Just hold that right there for me, don't move, don't make a sound. Right now you are nothing more than a panty wearing, purse carrying soap dish." The soap tasted awful but I didn't dare move a muscle or make a sound. Was this my punishment for tonight? I didn't know but it was wonderful to watch her relax in the water and flip through the screens of her phone. She turned towards me, lifted her phone and snapped a picture of me. I must have looked ridiculous. Then she began typing and she giggled as the whooshing electronic sound of a text being sent went off. My stomach dropped. Shortly after that there were a series of 'dings' indicating incoming text messages, more typing, more whooshing sounds and quite a bit of giggling from my beautiful wife. After about ten minutes of texting she locked her phone screen and handed it back to me to return to her purse. For the next twenty minutes I was simply a soap dish. She would pull the bar from my mouth, lather up her washcloth and then put the bar back. Finishing her bath she stood up, suds still clinging to her perfectly curved body. Ashamed of myself for staring at he beauty I quickly averted my eyes downward to her feet. Rubbing her body with a fluffy white towel she turned and pointed to a pink razor on the side of the tub. "Shave everything that is below your eyebrows, do you understand?" I nodded since I could not speak. I hesitantly removed her panties and set her bag by her side of the bed, then returned to the bath and began to shave. I did not remove the soap from my mouth, which I think was the right thing to do since Karen had not given me permission to do so. Not being accustomed to shaving my legs and being very, very careful with my balls and penis it took a long time to finish the task. The water had begun to get chilly which made my already little wennie seem just tiny. When I was done I dried off and put the panties back on. The soap was really getting frothy in my mouth and I had to swallow the lather now to keep it from dribbling out and making a mess. I was hoping that as soon as Karen saw I still had it in she would tell me I could take it out and that I was silly for leaving it in while I was in the tub but that was not to be the case. She looked up from the paper she was reading, the Wall Street Journal and with a devious smile told me to come to her. When I did she lifted her purse and took out her large matching Michael Kors wallet and a large silky pink hair tie. She handed me her purse to hold and then reached down and pulled the waist of my panties down, exposing my little dick and balls. Lifting my balls Karen began wrapping them tightly in her hair tie. When she pulled the panties back up my balls had been carefully positioned so they were tightly held in the front of the panties and my little dick had been tucked out of the way. "Well, I guess we need to get this punishment started don't we?" she said while tapping her large, heavy wallet in her palm. With the soap in my mouth all I could do is whimper and keep drinking lathery saliva. "Now, this is going to hurt, which it should because it is punishment. I don't want you to move, just concentrate on sucking on your soap and think about how much this hurts so you will remember it." With that she took her wallet and slammed it into my bound balls, the pain was immediate. Normally I would have fallen to the ground but I remembered her warning and concentrated on the soap in my mouth. Nine more times she slammed her wallet into my balls, every time hurt more than the last. After the tenth one she told me I could go take the soap out of my mouth and come back to her. I walked back into the bedroom a bit bow legged but did not complain, I was afraid to talk to I just stood before her. "Kneel," she said, "you may kiss my wallet and thank me for your punishment now." Quickly I knelt and pressed my lips tenderly against her black wallet, the instrument that delivered so much pain to my swollen testicles. "Thank you so much Mrs. Karen for taking the time to punish me and help me learn. Thank you for smacking my little balls with your pretty wallet, thank you so much." "Very good sissy, now its time for bed." I lay there for a long time and couldn't go to sleep. Laying very still my mind just kept replaying the events of the day over and over, so much had happened and so many things had changed in just a few hours. My balls ached horribly and I was a nervous wreck wondering if she had sent my picture to anyone and if so who (but I knew better than to ask). Finally I must have drifted off to sleep. I usually wake up quite a bit before Karen, well I always wake up earlier than her on weekdays so I can go over her clothes for the day with a lint roller, iron them, give them a quick spritz with her favorite fresh scent and make sure that her shoes and purse are clean. I must have been exhausted because my wife kissing me while rubbing my still tender balls awakened me from my sleep. "Good morning sissy," she said pulling her lips a little away from my mouth. Her kiss had been very forceful and her tongue had found its way deep into my mouth. "Just lay still," she commanded as she pulled down my panties, once again I saw the dreaded pink hair tie in her hand. With one hand she quickly wrapped my poor balls tightly in the soft pink hair band and positioned them so they were front and center of the panties. Looking down at them they were bulging up under the pretty lace fabric. "Let's get this morning started on the right foot shall we sissy, I want to make sure that you are in the right frame of mind for our day" she said with a huge smile. She lifted up her heavy black wallet to my lips, "Give it a kiss and ask me to hurt you." I reverently pressed my lips against the front flap of her wallet, kissing the gold emblem on the front. "Mrs. Karen, I was very ugly last night and I want to thank you for punishing me by spanking my balls. Would you please spank them again this morning to help me understand my place, please hurt my balls with your pretty wallet. Please don't have mercy on me. My balls aren't much use for anything other than being a good place for you to hurt me." She began rubbing the wallet firmly against my bound balls. "You know honey, the real reason that I am doing this is simply because I had such a good time punishing you last night. This may come as a surprise to you but my pussy was soaking wet by the time I was done. This morning you are going to endure ten more wallet slaps on your balls from me, and then I am going to relax and watch you slam the wallet into your crotch ten more times for me, and I want you to really hit them hard. I want to see you cry. When you are done with that I am going to lock your chastity cage on and then you are going to spend some quality time between my legs." "Yes ma'am," I whispered. "You know what?" she said. "I like it when you use Mrs. Karen and yes ma'am. For now on you may only address me as Mrs. Karen and you will use ma'am. In fact all women, no all females no matter their age or position in life will always be referred to as Miss or Mrs. and answered with yes ma'am or no ma'am. Do you understand me purse-sissy? Now spread your legs a little so I can really smack those worthless little balls, let's see if we can get the to swell and change colors!" "Yes ma'am Mrs. Karen," I said while opening my legs for her. "Ah ha!" she exclaimed reaching for her purse which was on the floor next to our bed. She dug around for a bit and came out with an Always Overnight maxi pad; the sight of the feminine maxi pad in its purple plastic wrapper transfixed me. "Open wide sissy," she said and then stuffed the purple maxi pad deep into my mouth. "That should keep the noise down to a minimum, after all I want to hear the sound of that wallet slamming into your bound balls, not you crying and moaning." With a wicked smile she lifted her wallet high and brought it slamming down against my crotch. Whether my balls were already sore from the previous night or she was swinging it much harder this really hurt. Over and over she smacked my tightly tied testicles, the whole time she was telling me how sweet a sissy I was and how this made her so happy. After what seemed like an eternity she leaned over and kissed my cheek. "You did so well sissy, you're not even crying hard but we are going to change that." She handed me the wallet and looked directly into my eyes and in a very serious tone said, "Now it*s your turn, I want you to pound your balls brutally, I want you to hurt them bad, I want to see you cry. I will tell you when to stop, until I do that you better impress me with how much you want to please me." I took the wallet into my shaking hands and watched as she fluffed up her pillows and comfortably reclined against the headboard of our bed. I noticed that her hand had slipped under the sheets and I could see a little bit of motion where she was slowly rubbing herself. Biting down against my maxi pad gag I raised the wallet and brought it down as hard as I could against my bound mound of swollen testicles. The pain shot through me but without thinking I raised her wallet and struck myself again and again. I don't know how many times I did this because in the pain I lost count. I couldn't see her anymore through the welling of tears that ponded in my eyes but I kept raising and striking my balls for her, hoping that she was getting as much enjoyment from this as possible. All I could think of was pleasing her. Finally I felt her hand press down on the wallet, keeping it against my groin. "Nicely done sissy, look at your cheeks all covered in tears. Next time we do this I think that I will put eye makeup on you so I can watch the mascara run, don't you think that would be a nice touch to add to your wife's enjoyment?" I couldn't answer, my teeth were still clenching the maxi pad she had put in my mouth. With a smile she leaned over and kissed me on the forehead, then pulling the pad from my mouth she kissed me hard on the lips, her tongue thrusting forcefully into my mouth. She owned me and I was beginning to understand this. With her other hand she continued to rub her wallet hard against the front of my panties, accentuating the pain in my poor testicles. She lifted away from me and lifted something off of her nightstand. I could feel her pulling down the panties but my balls were in so much pain I could not feel her removing the hair tie. After fiddling around with my privates for a bit she pulled the panties back up and gave me a quick peck on the lips. I reached down and was surprised to feel that she had fitted a chastity cage on but it didn't feel like my little silicone rubber one we always used. I pulled down the waistband of the pink panties only to be greeted by the sight of a very sturdy looking steel cage with an internal lock. Karen giggled and said, "Surprise honey! I got you a new cage! This one is very secure and is designed for very long term use; the manufacture says it can be worn permanently. It has some nice features, since it is medical grade stainless it is very strong, the lock is a set of tumblers that is inserted internally to hold it together so it doesn't click and clack like a padlock and cant be cut off, it is also lock pick proof so only this key can remove its, and a urethra tube that comes with it. It can be inserted into your urethra and locked into place, basically taking away your ability to control your pee. I can see you looking at this beautiful key. I am going to wear it on an anklet most of the time, a dainty thin gold chain that could easily break. I am sure that I can count on you to keep an eye on my ankle to make sure that it doesn't get lost. I gave the other key to the nurse at my OBGYN doctor's office. Oh that reminds me, you will start having regular checkups there as well to ensure that everything is ok down there, well everything but your little balls because those are always going to be broken." With that she rolled over onto her back and slid her panties off exposing her beautiful mound, so pretty and neatly framed by a little tuft of fur. Without needing to be coaxed I excitedly slid my face between her open legs. "Go slowly, take your time sissy, I want to enjoy this for a while" she moaned as I positioned myself below her. "Yes ma'am Mrs. Karen" was my muffled response. I began by softly kissing her monds, the little bit of very neatly manicured hair tickling at my nose. She was already drenching wet from rubbing herself while I punished my balls with her wallet. Gently moving around her labia, kissing her soft lips and running my tongue in short, soft streaks around the inside of her lips, just touching her vagina she began to squirm a little. I slowed my pace because she seemed so close to orgasm already. Was her taking control of me and hurting my balls this much of a turn on I thought to myself. She began to softly murmur to me, "sissy you do such a nice job down there with your mouth, Mmmmm you know I am going to get orgasms any time that I want them but you my little sissy are locked up and don't have a key now do you? What do you think of that sissy? I think it is wonderful...ohhhh ugggg, mmmmmaaaahh, just thinking of it is making me drip. I own your little cocklete and I have no intentions of letting I out any time soon." I knew better than to answer her, it was my duty to concentrate on her pleasure. She was on the verge, poised to tumble off a cliff of pleasure, carefully I maneuvered, keeping her as close to the edge as possible for quite a long time, then I felt her hands on my head, pulling me in closer. I knew this meant she was ready for her release. Now my efforts began to include her clitoris, circling it with my tongue, gently licking the skin directly above it, and in-between there were gentle sucks on her little magic knob. Now I was in a steady rhythm, not fast, not slow, just where I knew she liked in, circling and licking. Her hips began a slow pumping and her hands were dragging my face deeper into her, I had to time my breathing with the thrusting of her hips just to get air, then it happened. I felt her begin to shudder and a long low moan began to well up from her, then little girly sounding yips as she thrust harder her whole body shaking. There was a flood of fluid from her pussy, I was careful to catch and drink all of her nectar. She began slowly stroking my hair with her nails, now it was easier to get air but I wasn't sure she wanted me to stop. I began circling her labia lips again gently as her hip thrusts slowed down then with a sudden ferocity that took me by surprise she drug my face back into her and began humping her groin into me again, forcefully thrusting, she was fucking my face, riding me owning me. This time her orgasm was huge, with what seemed like a pint glass full of fluid gushing out. I worked hard to capture it, which was hard because she was shaking so violently, and pulling my head into her so hard. I gave up on trying to take a breath and just concentrated on my job. As this orgasm, the most powerful one I had ever seen her have, began to crest and wane she slowly started to breath more normally, her panting was becoming less pronounced. "Oh my sissy, that was just wonderful, now go make me some breakfast and start working on your chores" she said while rolling over. "Don't forget to hold my purse and go ahead and stick that maxi-pad back in your mouth to remove the temptation of you talking and disturbing me." After breakfast and chores I got in the shower and cleaned up, her juices had dried on my smooth face and even got into my shoulder length brown hair. I had to wash it twice to get it clean. In particular I washed around my new chastity cage. It was very secure and there was no way it would be coming off without the key, this wasn't the plastic toy we had used before. By poor balls were swollen and they were actually bruised a deep blue, it hurt to touch them so I soaped very gently and rinsed. While I was showering Karen stepped into the shower room and set some clothes down on the top of the commode lid. "Just brought you some clean undies for today honey, we need to go out and I can't have my sissy husband going around with smelly panties on" she said in a cheerful tone. "The maxi pad goes in the front, you are probably going to leak pre-cum while wearing the cage long term and I don't want your panties getting messy, understand?" I turned off the water in the shower. "Yes ma'am Mrs. Karen, thank you ma'am" I said, reaching for the towel. I dried off and stepped out to find a pair of light pink panties and a maxi pad laid out for me. I slid them on, the feeling even more intense that before as they glided up my smooth, hairless legs. Looking down at my freshly shaven legs and panties the effect was a bit startling. I was a small guy, maybe a hundred and forty pounds but I kept myself fit, well at least well toned. The effect of my thin legs without hair and a pair of panties was very feminine. If I didn't know that I was a guy it would almost seem that the lower half of my body may have belonged to a woman. It was also a little weird wearing the maxi-pad, Mrs. Karen had picked one of the big overnight ones, like she had gagged me with, and I could feel it rubbing against my crotch and inner thighs, just another reminder that I wasn't in control. I stepped out of the shower room into the bathroom and saw my beautiful wife at her makeup table fussing over her face. Without stopping her work she glanced at me and smiled. "Those look very nice on you sissy, we are going to do some running around today, I laid some clothes out for you on the bed." Looking over to the bed the first thing I saw was a white t-shirt, one of the thin comfortable ones, I pulled it over my head and it fit but a little snug. It was what was next to the shirt that made me do a double take, a kaki pair of shorts that I didn't recognize as mine, lifting them up and looking at the tag it read 'Dillards', these where a pair of Karen's shorts! I picked them up and very timidly walked back into the bathroom. I didn't want to disturb or make Mrs. Karen mad because I was afraid of the hair tie and wallet but I knew that there had to be a mistake, these were women's shorts and the shirt was too tight, almost form fitting. I approached her and just stood there, in a snug white t-shirt, pink panties, holding a pair of her shorts. I didn't know what to say, and I definitely didn't want to disturb her so I just stood there about four or five feet away watching her finish her eye makeup and then apply her lipstick. When she noticed me standing there she turned towards me, still holding the open tube of brownish red lipstick in her right hand. "Yes honey, what is it?" "Ahhhmmm, well, I mean, are you sure these are the clothes you laid out for me Mrs. Karen ma'am?" I stammered. The whole time the only thought in my mind was please don't make her mad, please don't punish me. "Of course those are the clothes I set out for you, a little purse- sissy cant be in control of important things such as what she wears when out in public with her wife can she." Was it my imagination or did my wife just refer to me as a female using the pronoun 'she', I was so confused. I didn't say anything about it, mostly because I feared another ball beating. "No ma'am, they just seemed a bit odd, I don't think that they are my clothes." "Well, I am tired of going out with you wearing old raggy-baggy clothes, you look like a homeless person sometimes. If you are going to be my husband and my sissy carrying my purse around then you are going to start dressing with a little more style. Besides, I like your tight little butt and those shorts will show it off a bit more, I can walk behind you and watch it wiggle a little," she said with a giggle. "Oh, I set a new pair of sandals out for you too, your old ones smell bad." I looked over by the bed and saw a pair of white sandals that definitely didn't look masculine. They were very feminine with poofy tassels and slender straps and buckles. "Honey, is there a problem with what I chose for you to wear today, do you have a problem with me taking control of your wardrobe? Penny told me last night that she expected you to dress better than you usually did for the office, I like her quite a bit but she seems like she could be a very demanding woman to work for." She just sat there looking at me, holding the lipstick. "Honey, are you deaf, I asked you if you had a problem with the clothes I picked for you?" Her voice had gone from sweet and happy to very serious. "No ma'am, no problem, I was just checking." "Well I think that you were showing some disobedience and I didn't like the way you barged in here while I was working on my makeup!" Oh shit I thought to myself, this is going sideways fast, what surprised me even more than my mental reaction was my physical response, my knees actually began to shake and I started to cry a little, why was I crying? I knew why I cried when she was punishing my balls but this didn't make sense, but here I was, standing in front of my wife trembling and crying because she was talking sternly to me. "Come here," she demanded. Without hesitation I stepped forward and knelt down in front of her. "Please ma'am, I didn't mean to be disrespectful, this is all so very different for me. Please, I am trying to learn but I keep making mistakes. I really love the clothes you picked out for me, thank you so much." It all came out in a gush, some of it was because I feared for my balls but some of it was because I felt that I had disappointed her in some way. That was odd, I had never been truly this concerned about making her unhappy in any way or coming up short of her expectations. "I understand that this is going to be difficult for you honey but you have got to relax and trust me more. Yes, there have been some changes but we have just begun, there is a lot more to come before I will be completely satisfied. You must understand that even with such a sweet little apology and you down on your knees that I am going to have to punish you so you will learn.." "Yes ma'am, would you like me to go get your hair tie and wallet?" "Oh, that is so sweet but no, well at least not right now, later on tonight if you ask very sweetly I will play with your little balls. I think that I need to come up with a more fitting punishment for your issue with the clothes." She smiled so kindly while brushing the back of her fingers against my cheek. "Honey, you must learn that the only person you should worry about pleasing is me. Don't concern yourself with what others may think when they see you and for goodness sakes don't concern yourself with what you might think because that doesn't matter one little bit. You must learn that your humiliation is for my enjoyment and that is much more important than your pride. Now go get dressed." I quickly hopped up and slid on the kaki shorts, they fit quite snugly in the butt. There was also a narrow white braided belt that she had laid out. The sandals finished off the outfit. Looking down I realized how evident it was that my legs were shaved and that I was wearing women's clothes. To be honest, it was more androgynous than women's clothes but there was definitely something very effeminate about the whole thing. As I was standing in front of the full length mirror on the back of the closet door I heard Karen come up behind me. "Mmmmm, yummy" she said, "turn around for me." I slowly turned so she could see my front and side. "Oh no, that wont do," she said, "I was afraid of that." With that she began looking through her panty drawer and came out with what looked like another pair of panties and handed them to me. "Honey, your little clittie cage is making a bump in the front of the pretty shorts I picked for you and that just will not do, these are a pair of firm control panties, they have a tight panel in the front that will mush that little bulge into oblivion." I took them from her, removed the shorts and pulled them up my legs. These were very tight and I had to pull them up over my already pantied chastity cage. She was right, the new undergarment smooshed my little thingy down flat and when I pulled up the tight kaki shorts my front was perfectly smooth. "That is much better, we will buy you many more girdles, corsets and such to keep you flat, I don't ever want to see that bulge again, do you understand me sissy?" "Yes ma'am, I understand," I replied without truly understanding what I was committing too. Mrs. Karen seemed very happy with the shorts now that the front was smooth and showed no signs of a 'naughty bump' as she referred to it. I was looking at the strange visage of me in my new clothes in the mirror when my wife came up from behind and wrapped her harms around me. "Mmmmm, you are such a sweet husband," she purred while giving me a firm hug and turning me around to face her. She began to gently kiss my lips and nibble at my ear lobes. "You know I love you very much," she whispered into my ear, her warm breath accentuating the words. Her hands were kneading my butt cheeks, which were very tightly held by her kaki shorts. All of this attention felt good, I returned her kiss and gave her butt a squeeze in return. "You see sissy, if you are a good little girl then mommy will reward you, it's not just punishments all of the time. Today I want you to be happy, cheerful and bright. Just accept what happens as what will be and should be." She followed up with a very sensual kiss, her tongue darting into my mouth, finding mine. I was so excited; her kisses, her hands, the smell of her lipstick, makeup and perfume were all so much. My little man down there was trying to get hard but in the tiny cage and crushed down by the panty girdle all he could do was strain painfully against the cage and leak. Now I know why Mrs. Karen insisted I wear a maxi pad, I could feel pre-cum leaking out, it would have caused a very embarrassing stain in my shorts if it weren't for the pad. I got a little nervous, was this going to happen all the time? But remembering my wife's words I calmed myself and focused on relaxing and trying to enjoy her attention. "Now go get my purse, make sure that there are at least four of the big purple overnight maxi-pads in there and let me finish getting dressed. You can sit in the car and wait for me with my bag in your lap" she said, spinning me quickly around and giving me a hard slap on the butt to hustle me on my way. I was sitting in the passenger seat of her car waiting for quite a while but I knew better than to rush her, Karen liked taking her time when getting ready. When I did see her it almost took my breath away. She was wearing a very short peach colored sundress, the fabric was so light that it bounced and flounced around with every step she took. It looked marvelous against her light olive complexion. She had on a pair of cute, flat sandals with thin straps across her toes, which were painted a darker beige color. There was a gold toe ring on the second toe of her right foot and around her right ankle was a fine gold chain with a small key dangling on it. My heart stopped when I saw how delicate the anklet chain was and all I could think was "please don't break." She slid into the driver seat and gave me another wonderful kiss and I handed her keys to her from her purse. While she was driving I would occasionally lick my lips, both to taste her lipstick she had left on me which was very erotic for me and to try and remove it from my lips without her noticing.

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Heathers Sissy

Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...

3 years ago
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Forever Her Sissy Chapter 1

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 1 It was It was quite an opportunity to be on this special team dedicated to a multi-year market research...

3 years ago
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The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

2 years ago
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Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

4 years ago
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Sissy Mission 4 Southern Belle Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 4: Southern Belle Sissy By Cheryl Alison Mistress believes in community service. So when she dropped the ad on my desk at home, I knew that I would be a faithful community servant within a short while. The ad read: Southern Belles Needed The Ladies' Auxiliary needs...

3 years ago
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Mothers Sissy Teachers Pet Part 3

Mother's Sissy, Teacher's Pet, Part 3 "Sandy's Diary" By Sandy Brown January 15th, 2012 Dear Diary, This is my very first entry! When Mom bought me this diary for Christmas, well, to be honest, I thought that only girls wrote in diaries. It didn't help that you are pink. Mom told me it's just a pale red, but you look pink to me. She also told me that lots of boys write in diaries, but the only kids I know who have...

3 years ago
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Sissy Therapy

My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...

3 years ago
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My Stepmothers Sissy Daughter

My Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...

2 years ago
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Forever sissy

This story is based on something that really happened to me. Yesterday i cam out of the shower and, as always, looked at myself in the mirror. i always get pleasure looking at my soft little impotent cock resting on top of my ball sac. My fat titties bulging out to the sides and my rolls of flabby fat!! i've always said i look like i'm pregnant!! My pubic hair is gone and my underarms are smooth too. However my wife will just not allow the rest of my body to be smooth. Anyway, getting back to...

3 years ago
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Stepmothers Sissy Schoolboy

One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
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Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

3 years ago
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Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
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Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
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My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
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My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

4 years ago
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A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

2 years ago
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Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Four Daisy Training Prepares Her for the Workshop

Teaching the Sissy Maid Workshop at the MVP, Chapter Four: Daisy Training Prepares Her for the Workshop Synopsis: Flashing between Daisy's training before the seminar and the seminar's beginning, more is learned about how Daisy trained to be ready as Ms. Rebecca's sissy maid example and how the Sissy Maid Workshop is run to insure the transformation of the submissive male candidates into the sissy maids and cuckolds wanted by their owners. I loved the look on Daisy's face as...

1 year ago
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Preachers Daughter Chapter 13 and Preacher Sucks

My wife, Charlotte, thought it was very nice and thoughtful for Jaimie, the 23 year old preachers daughter now moving with us, and unknown to my Mrs, Jaimie was carrying my baby, "Jaimie, thank you for all you did around the house today, but you know, you are not our slave, are our guest!" If my wife only knew, that Jaimie was "my slave" and number #1 cum slut.Charlotte was always wild in bed when alone or away in a hotel or when our k_ds were not home, date night always got me plenty of hot...

2 years ago
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We got us some sort of sissy fag here

Check Your Taillights It all started pretty innocently, at least by my standards. For many years I have been a closet crossdresser and like most, I thought there must be something wrong with me. The usual bag of emotions and guilt. One day I did an online search to see if there was a forum for crossdressers and sure enough there was. My whole world changed. Not drastically but change it did. I found there were many others who felt and dressed as I did and I finally found out I...

4 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

2 years ago
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Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing
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...

3 years ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
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Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

3 years ago
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My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

2 years ago
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A sissy in her early 20s begins a cyberrelationship with a Master

It started innocuously enough with what seemed like a harmless exchange of private messages on a friends- based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some forced feminization and even surgical “enhancements.” The young sissy, April, responded openly and eagerly, and the conversation developed into one in which more and more of the sissy’s fantasies...

3 years ago
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An Online Sissy Lives Her Dream

(Dedicated to a hot little sissy here on xhamster, Sluttish, whose looks and fantasies inspired this story. Her fantasy name is April. That’s where this story starts.)It started innocuously enough with what seemed like a harmless exchange of private messages on a friends-based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some forced feminization and even surgical...

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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Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

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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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

3 years ago
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How my girlfriend turned me into her sissy bitch

Her Perfect Ass And Evil Sexy Dirty Looks Mind Fucked Me Into Wanting To Be A Girl Rather Than Fuck One......as this naive, innocent, christian, bible believing 20 something gave me the best sex of my life with a reach around, as I would cum, she would whisper "Not bad for a cock sucker. LOSER!" and then push me away, stand up, look at me in disgust with those evil sexy eyes that would become so powerful as she threw me the meanest, 'fuck you, loser' look ever, then she would leave, her perfect...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

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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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

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