My Sister's Sissy free porn video

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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 the disappointment when I had to put my boy clothes back on. I can also remember stealing a pair of plastic panties from a clothesline in the neighborhood when I was about 8 or 9, and my total frustration when I couldn't get them even close to all the way up. Yep, I was a sissy, alright. By the time I was 15, I had tried on all of my older sister's clothes, but really didn't like her style. She was 18, going to a good college, but luckily able to live at home. Her clothes tended to be trendy and little bit slutty, which worked perfectly on her. Linda lived up to her name, she was beautiful! Now Mary was my younger sister, but only ten months and a few days, and her clothes were a different story! She was a total girly-girl, and loved dresses that had lots of lace, satin panties, satin nighties, and to my everlasting delight, was almost the same size I was. Needless to say, I wore her things, a lot! What I didn't know was that both of my sister's knew I wore their things. They would find things folded just a bit differently, panties put back in the wrong place and such, and so, began to watch me, and found out my little secret in short order. One warm spring evening, just before school was out for the summer, they both came to my room to talk to me about it. Hmm, maybe just a bit of family background would be appropriate here... My father worked for a company that required lots of travel. He was usually gone for three or four days at a time, but sometimes for a week or two. My mother had passed away when I was ten, so it was just the four of us, and most of the time, just the two girls and me. That fateful evening, the night it all began, Dad was in Europe for a few weeks, and we were on our own. Linda and Karen trooped into my room about seven in the evening, and asked me to pause the video game I was playing, because we "had to talk." Linda started the conversation with the bombshell. "Josh, we know you wear our things, and we've known for quite a while, and we need to talk about it," she began matter-of-factly. I immediately denied the charges, all the while knowing that I had on a pair of Karen's pink satin panties that I had fished out of the laundry hamper not an hour earlier. "Please Josh," Karen continued, "I put a pair of my favorite panties in the hamper tonight as a test, and they're not there now. We know you have them, so please quit denying it." I deflated quickly, and just sat there on my bed with my head down. "Are you wearing them now?" Linda asked gently. All I could do was limply nod my head, and then I began to sob quietly. Both girls sat down on bed on either side of me, and put their arms around me. "Josh, it's okay, I guess, if you like to wear girls panties," Linda began, I mean, "everyone has their own thing, and..." she didn't get to finish because Mary put her hand on my leg, and urgently whispered, "Let me see them! Let me see you in my panties, please!" I looked at her in amazement, and after staring at Mary for a moment, Linda finally told me to stand up and take off my jeans, so they could really see what I was wearing. I know I was blushing from my toes to my scalp as I slowly lowered my jeans. As they fell around my ankles, Mary's pink satin panties came into view. They were beautiful things of smooth, silky satin that almost looked wet. There was pretty lace that surrounded the leg openings in the back, and an overlay of lace on the front. The final girly touch was a pink satin bow right in front. I loved them! Of course, there was more. I was also wearing a pink satin garter belt (No, it didn't match, but was as close as I could get, buying one from a discount store, crammed in among other purchases) and the garters were holding up white thigh-high stockings. Without a word, Linda grabbed my shirt, and started to rapidly unbutton it, to reveal a white nylon camisole, again stolen from Mary. I stood there, tears of shame rolling down my cheeks, as both girls just stared and giggled at their sissy brother. Linda tried several times to speak, only to be overcome by a giggling fit each time. She finally got herself under control, and told me to take off all the boy clothing I had on, and then come to her room. Taking Mary by the arm, they exited, telling me I had exactly 60 seconds to be in Linda's room, or I was really going to get it. I was scared, humiliated, and yes, turned on. My cock was doing its level best to tear the pretty panties that imprisoned it, my pulse was racing, and my breath was coming fast and heavy. Yep, I was turned on all right! In less than a minute, I was standing in Linda's room, wearing nothing but the purloined lingerie, with my cock tenting Mary's pretty panties, and my face red with shame. Mary just looked at me and to my surprise, told me that she didn't want the panties back, but that I had to take the training bra that matched them, and put it on. She held out the delicate garment, and I slowly removed the camisole and Linda instructed me on how to put the bra on, properly, not putting it on backwards. It took me several attempts, but I finally got it hooked behind me, and Linda then adjusted the straps so it fit better. I was told to put the camisole back on, as it was now mine, too. I looked in the mirror, and the lacy pink bra that showed through the semi-sheer white nylon of the cami made me look even more girly, and even more humiliated. I was to find out in just a few moments how much more humiliated I could be! I was handed a pair of Linda's white high heeled pumps, and after struggling to get the ankle strap buckled, was helped to stand up, and was made to walk back and forth across the room. I freely admit that I showed all the grace of a hog on ice at first, but with some coaching, managed to walk pretty well on the three inch heels, although not with any grace. The girls made me stand in front of them, and Mary reached under the pillow and pulled out a mass of pink ribbon. I was told to hold my hands out, and while Mary tied my wrists together with one ribbon, Linda knelt at my feet and tied my ankles tightly together. Next, my legs were bound together over the knees, and Mary tied another ribbon around my arms, just below my elbows. I was now in lingerie, and bound with feminine ribbons, just as tightly as with steel shackles. Linda pulled a chair up just a bit ahead of me, just to my left, and sat down. I wondered what was going on, when Mary suddenly pushed me, and I fell across Linda's lap. Linda's right leg wrapped around my bound legs, and her left hand was on the small of my back, pushing me down, hard. With me bound and securely held across her lap, she began to reign blow after blow on my pantied ass, each crack accompanied by a grunt from her, and a scream from me. After five or six painful blows, she stopped, and asked me why I was being spanked. Tears rolling down my face, I told her I had no idea, but begged her not to hit me again. A few minutes of me begging and pleading seemed to make her angry, and she told Mary that they would indeed need to gag the pathetic sissy. Marry clapped her hands and giggled loudly. She came up beside me and told me to open my mouth. When I refused, Linda told me that I had two choices. I could either allow Mary to gag me, or Mary would bring Linda one of Dad's leather belts, and I really would get my ass beat. I surrendered, and opened my mouth. Mary shoved a pair of nylon panties (clean ones, alas) into my mouth, and then used the last piece of pink ribbon to bind them into my mouth, and she was none to gentle about it. "Now (slap!) Sissy, (slap!) you (slap!) are (slap!) being (slap!) punished (slap!) for (slap!) stealing (slap!) our (slap!) panties!" Linda punctuated each work with a vicious spank to my poor bottom, alternating cheeks with each blow, and I saw that Mary was dancing around with a digital camera, recording my humiliation for posterity. My spanking ended with a flurry of blows that left me bawling and screaming into my panty gag, and her huffing and puffing with the exertion. They stood me back up, and as I stood there, still bound and swaying on the high heels, with tears still running down my face, Linda let me in on my future. I was informed that from now on, I was to wear only panties under my boy clothing, and that when I got home from school each day, and whenever they wanted me to in the summer, I would be wearing dresses. I would also be doing all the laundry, and would hand wash each and every piece of lingerie. I was also going to responsible for cleaning not only my own room, but Mary and Linda's, and would make each girl's bed each morning. If I failed to perform my duties properly, then I was told that the twenty-five or so pictures that the girls had would be instantly sent out over the net to all my friends, and posted on my Face Book wall. I was finally released from my ribbon bondage, but not my frillies. I was told to go to my room, and bring Linda the money I had been saving for a car. I only had about $750 saved up, and really didn't want to give it up, but I felt so small, so, I don't know, submissive maybe, that I meekly went to my room, and brought the old cigar box full of money to Linda without any protest. She told me that they didn't want me stealing and wearing their intimate things, so this money was going to be used to buy me my own things. Mary piped up brightly at this point, "Now Josh," she paused, looking at me, "First of all, from now on your new name is, let me see, Melissa! Yes, when you are dressed up, and anytime we are alone, you will answer to Melissa, or Missy. Is that understood, Missy?" I nodded, meekly. The next thing she said hit me right in the gut. "Oh, and Josh," she said sweetly," Linda and I went on your computer this morning, you have such and easy password! We found some of the sissy sites you looked at, and we know where we're going to buy your new wardrobe, you lucky little sissy!" I started to stammer out something to the effect of "I was just looking around, and found those sites by accident," but the fact is that every time I was on the computer, I went to Birchplace Shop, I Love Ruffles, Auntie Annie's Baby and Sissy store, and had several lingerie sites in my favorites on E-Bay. I have even spent hours looking at adult baby sites, and adult baby diapers, plastic panties, and beautiful satin rompers. "Gulp!" With a warning that if a baby sister lied to her older sisters (baby sister?) she would get another spanking, and have some naughty pictures spread around, I quickly shut up! I was told that I was to keep my body free of hair, except for my head, and that if Linda checked, and I had any stubble, it was spanking time. I was also told that since I only had one pair of panties, for now, Linda would give me another pair that she didn't wear, and I had to hand wash mine every night. I thought that was it, but Mary added another little chore. "Hey Sis," she said, turning to Linda, I think Melissa ought to clean our bathroom, too. I mean, she will be in there to get our dirty things every other day (I had to do their wash every other day?) so why can't she clean the bathroom while she's there? And since she's gonna clean one bathroom, why not the main bathroom upstairs, and the half-bath downstairs?" "Linda began to laugh. "Oh my Mary, you're gonna grow up to be a little dominatrix, aren't you?" The final indignation of the night was "The Measuring of the Sissy," as my arms, legs, waist, "bust" hips, thighs and head were measured, with the measurements recorded on a sheet. I wasn't sure I wanted to know what all the measurements meant. Three weeks went by before anything else was said or done. I got up an hour early to make my own bed, and to be showered and dressed by the time the girls were up and dresses, so I could make their beds. Monday, Wednesday, and Saturday I cleaned the bathroom that separated the girl's rooms, then I did the laundry for the whole family, along with hand washing my own two pairs of panties, and all of my sister's lingerie. Even when the girls wore just plain cotton panties, the rule was hand wash, so in order to keep those pictures off the net, hand washing it was. I do have to admit that I loved to handle their dirty frillies, and each pair of panties went to my nose, before they went to the sink! I changed their sheets twice a week, and even changed Dad's sheets weekly. He was amazed at how much I had "changed." He must have commented daily about me pitching in to help keep the house clean and do the laundry. He, of course, knew nothing about my panties, my hand laundry service, or making the girl's beds. All he saw was me cleaning the bathrooms and doing the laundry, which used to be the girl's jobs. School was finally out for the summer, and Dad was away again, this time only in Atlanta for a week. It was Saturday, and I was looking forward to just relaxing in bed. Wrong! At a few minutes past eight, I was blinded as Mary pulled the curtains open, and Linda whisked the covers off of me. I was told to get my sissy butt out of bed, take a shower, make all the beds, and to meet the girls in the living room. "Oh year," Linda added as she flounced out of my room, "You must wear your pink panties, and your bra. While you're at it, wear your white stockings and here are my white heels." She casually tossed them on the bed and left me alone. I climbed out of bed, and made my way to the bathroom. There was a note on the toilet telling me that I had to sit to pee, no more standing. I started to ignore it, then remembered that Linda was a computer whiz, and it would be just like her to have hidden a web cam in the room, or at least that's the reason I gave myself. I sat to pee, showered, ran the razor over what little hair I had, and went back to my room to dress. I pulled on the required lingerie, made my bed, and the minced down the hall and made Mary's bed. I kinda amazed myself that I was getting so good at walking in heels, even though I had practiced a lot in the last few weeks. As I went past Linda's full length mirror, I was surprised though, to see not a fifteen-and-a-half year old boy, but what looked like a twelve-year-old girl. I stopped, stared, and did a bit of posing before I came to my senses, and made Linda's bed. As I was finishing her bed, Linda yelled up the stairs for me to hurry my sissy butt along. I gingerly made my way down the stairs, my heels clicking on the wood, broadcasting my condition throughout the house, as if saying, "Make way for the sissy! Little sissy coming through! Don't worry, he's not a man, he can't hurt you! Make way for the sissy!" When I turned the corner into the living room, it looked as though there had been an explosion in a lingerie factory! Everywhere I looked I saw pink, lavender, peach, baby blue, and white satin. I just stood there and stared. Little did I know that I was to spend the rest of the day, trying on my new wardrobe, and becoming little Missy Melissa. Linda then did something that sort of surprised me. She handed me a tiny pair of white silky thong panties, and told me to go to the bathroom and put them on, then put my pink panties back on over them. Confused, I did as I was told, and found the white panties to be very, very tight, and until I got my penis situated, sort of between my legs, damn painful! I asked Linda what these panties were for, and was informed that they were called a gaff, and were designed to keep a boy's "pee-pee" from ruining the lines of "her" panties. "In your case, Sissy Missy," she added, "We just don't want to see our little baby sister's thingy while she's trying on her pretty new clothes!" I was first shown a pile of panties with matching training bras. Some were rather plain, although made of double-layer satin in sissy pastel colors. There were others that were dripping with lace, panties that I learned to call "rumba" style. There were bloomers, short and long, a couple of lacy, sissy thongs, and two that had lace-trimmed holes in the backsides. Hmm... After trying each matching pair on, and having my picture taken, I was told that the rest of the fashion show would be after breakfast, and some special preparation. Breakfast, I understood, and we were soon sitting down to some delicious cheese and mushroom omelets that Linda made. Still in my lingerie, I was told to put on some rubber gloves, and clean up the kitchen. Well, since Linda cooked, and Mary set the table, the least I could do was clean up. As though I had any choice in the matter... After I finished the kitchen, I was called back up to Linda's room, where I was sat down at her vanity. I was ordered to remove my shoes and stockings, and Mary sat down on the floor at my feet. I didn't have any time to wonder why, as she quickly grabbed my left foot, and went to work with clippers, a file, and some other tools. Linda had grabbed my right hand and was doing the same. Linda, though, after she had poked and filed a bit, grabbed a tube of something that smelled like super glue, and began to place long, fake nails on my hand. After she finished, she moved to my other hand. Mary, meanwhile, had finished with the tools, and was beginning to paint my toe nails a pretty pink color. Well, it would have been pretty on Mary, anyway. Linda soon began to apply the same color to my new finger nails, with a warning that for every nail I broke, I would get ten whacks on my bottom, from her hairbrush, not her bare hand, this time! Almost an hour later, I had two coats of paint on all of my nails, and was trying very hard to figure out what to do with my hands. Linda had grabbed her tweezers and was painfully plucking hairs from my eye brows, while Mary manned the ever-present camera. I was instructed on how to put on a little sparkly eye shadow, and pink lipstick to match my nails. I was shown how to line my lips, and how to put a sealer on them to keep them "kissing pretty." WOW! Now with pink nails and lips, thinned eyebrows, my longish hair was brushed and pulled back into a pony tail, not a boy's, but a girly one, starting high on the back of the head, and it was held in place with a big pink ribbon. With that final touch, I was led, barefoot, back to the living room. Once there, I tried on three dresses that looked as though they belonged to some toddler competing in a beauty pageant. One was baby blue, the other was pink, and the final dress was yellow with miles of white lace trim. All three were made of soft shiny satin, and had enough lace to make wedding gowns for a dozen brides! Of course, with each dress, I had to wear petticoats, the proper training bra and panties, there were matching nylon ankle sox with clouds of lace, and three pairs of shoes, that again looked like they belonged on a toddler. Three pairs of shiny patent Mary Jane shoes, pink, white, and black, each with a three inch heel were added to my wardrobe. I was glad I was wearing the gaff because I was as hard as a rock, and wanted to play with myself so badly, I'm afraid I would have done it right in front of my sisters, without a thought! I think I must have worn out the words "thank you" that day! Every dress, every pair of panties, every bra, every little accessory was so sissy, so girly, and just so beautiful! I even got five new nightgowns! Two were full length and three were little baby dolls nighties, and all of them were the sassiest, prissiest things that could be found on planet Earth. Linda told me that she and Mary had gotten so carried away that they even added two hundred dollars of their own money! When she told me that, I actually started crying! There I was, pink painted nails, make-up, wearing a long lilac satin nightie and a pair of 3 inch bedroom mules, bawling like a baby! Mary rushed over to me, and held me, and that even made me cry harder! I felt so little, so weak, so, so, sissified. I finally got myself under control, and then Linda asked me to take the baby blue satin dress, and the matching rumba panties, training bra, sissy socks, and the white Mary Janes, and to her room and put it all on. "Oh sweetie," she called out, "Don't forget to keep your gaff on! We wouldn't want your naughty little boy thingy to ruin your pretty girly clothes! I took the garments that I was handed, and made my way up the stairs to Linda's room, wondering if I would have enough time to play with myself. The answer to that was quick in coming. Mary followed me up the stairs, and told me that she was going to help me get dressed up, and touch up my make-up. "We wouldn't want anyone to see our little sister with mussed make-up, would we? She asked sweetly. Anyone to see me? NO ONE was going to see me! I mean, I loved all this sissy stuff, and wanted to wear it all the time, but I wasn't gay, and didn't want to be seen in public dressed this way! Well... While I was dressing, Linda ordered pizza, and we had a fine dinner. Mary had donned my new yellow dress, and even Linda put on a pale rose colored gown that she had worn as a bridesmaid earlier in the year. While waiting for the pizza to be delivered, we carried all my new clothes up to my room, and put them away. Linda told me that the dresses would find a place in her closet, so no visitor to my room would see them, and I could wear them whenever I wanted to. After we ate, we sat in the living room and watched a few movies until about six, and then Linda got up to get ready for a date. Mary also changed, as she was going to spend the night at a friend's house, which would leave me all evening to flounce around the house in my new dresses. After the girls left, I decided to change into the yellow dress that Mary had been wearing, as it was not only the prettiest one, but the prissiest by far. I put on the matching satin panties, which were a sort of bloomer style, and came down below the hem of the dress, ending in a puff of lace. I decided to borrow a pair of Linda's really high heels to wear with the dress, so I could practice with them. I dressed, and put on the white pumps. These had 5 inch heels, and little ankle straps, and looked so dainty and feminine, I almost passed out putting them on! I had some trouble walking, but spent an hour going back and forth across my room, and up and down the hall, and finally got the hang of them. I recalled Linda walking in heels, and sort of gyrated my hips like she did, and even though they caused my legs to hurt, and also the balls of my feet, I stuck with them until I thought I was getting pretty good. I also stopped in front of every mirror to gaze at myself, loving the sissy girly little thing that looked back at me from the glass. Since the girls were gone, I had taken off the gaff, allowing my little pee-pee to get hard as rock from the satin and frills. I was in sissy heaven! I gathered up all the lingerie from the girl's hampers, added my own panties, and headed for the basement to wash them all. I had a grand time, sniffing each pair of panties, and then washing them in the big sink and hanging them up on the line so they would dry. I was rinsing out the last pair of Mary's delicate silk panties when I heard footsteps on the basement stairs. I whirled around, and found myself face to face with my dad! I had nowhere to run, no place to hide. I just stood there, holding Mary's damp panties with both hands, and did the only thing I could do, started to cry. To my father's credit, he merely took the panties from me, and hung them on the line next to the rest of the lingerie, and then silently, motioned to me to follow him upstairs. We went into the living room, and he pointed at the sofa. I sat down, and he walked into the kitchen. A very, very long few minutes later, he returned carrying a glass of Pepsi for me, and a squat crystal glass, dark with whiskey, for himself. He sat in his chair, and just stared at me for a few moments, and then quietly asked me to explain what the heck was going on. "Uh, well, Dad, you see, uh, well..." was about all I could manage through my tears, and even that pathetic attempt at communication broke down into a full-fledged crying jag. I thought he was going to scream, to call me names, but all he did was set his glass down, and come over to the sofa, and sit beside me. He took my glass, and put it on the coffee table, placed his arm around my shoulder, and began to speak. "Son, I really want to talk about this. You see, I sort of know you have been sneaking around, wearing your sister's things, and I know you have taken a few things from Aunt Pat when she was hear for a visit. I guess you like wearing lingerie, don't you?" All I could do was nod, dejectedly. He finally helped me dry my eyes and ever so slowly the whole story came out. The only questions he asked were whether my sister's had forced me to wear this stuff, and if I had done anything "inappropriate" with either of my sisters. "No Daddy, NO!" I sort of whined. "Linda or Mary haven't even seen me naked, and I've never seen them! (Not really true, as I had watched both of them through door cracks, many times!) They were really sweet to me, helping buy all of these pretty things, and letting me play dress- up, and, and..." I broke down, and just sort of stared at the floor, wishing it would open up and swallow me. I finally got myself back under some sort of control, and told my father the whole story, start to finish. I told him about sneaking Mom's nightgowns from the laundry and cuddling with them at night, and how I began to actually wear my sister's things in the past few years, and even told him that I wanted to wear diapers! I don't know why I told him everything, but he just sat there, holding me, not yelling, not calling me names, just holding my like, like, like I was his little girl. I was so grateful for that. Finally, the story was all out, and Dad stood up, and held out his hand. I took it, and he stood me up, and asked me if I really, really liked dressing like a pretty girl. I nodded, and he told me to go upstairs and fix my make-up, and when I was ready, he would come up, and together we could look at all my pretty new things. I was flabbergasted! I ran as quickly as my purloined heels would let me, and began to wipe the smeared eye shadow and lipstick off, and to re-apply the best I could. I minced over to my room, and called downstairs for "Daddy." He came to me room, and together we went through all of my new frillies. One thing sort of confused me, and that was a box in my closet, all wrapped up in shiny pink paper, with the name "Melissa" written on it. I took it out, and Daddy told me to put it on the bed and open it, as it seemed to be for his new daughter. With shaking hands, I took the wrapping paper off, opened the box, and moved the tissue paper aside. Inside, I found three cloth diapers, pink diaper pins, two pair of plastic panties, one pink and one white, and then under the last piece of tissue were the most wonderful things of all! There was a lilac satin romper, or onesie, with snaps on the crotch for changing baby, a matching lilac satin bonnet, booties, and fingerless mittens! Dad told me to look in the bottom of the box, as there might be something else there. I did, and found a card. On the front of the card was a picture of a baby's nursery, and when I opened the card, it said, "I know in your heart, you want to be a little girl, and these things will help you to be a very pretty little girl. Love, Daddy" Now I started bawling again, but this time for sheer joy. Daddy held me while I cried, softly whispering, "It's okay, Melissa, shh, it's okay. I now have two beautiful daughters, and one part-time daughter who is just as beautiful." I think my crying mechanism finally rusted from all the tears, and the river slowed to a trickle, then to a drip, and finally stopped. Daddy wiped my face with tissues, and then began to help me out of my dress. When he had all my clothes off, he told me to lay down on the bed on my back. He produced a shaker of baby powder, and powdered my bottom and crotch, then told me to lift my little bottom like a good baby girl. When he slid that diaper under me, and began to tightly pin it on, I started to shake from the emotions. When he slid those crinkly pink plastic panties up my legs, and tucked them into place, I went into orbit from the feeling! He finally helped me sit up, and slid that heavenly romper on over my head, tied the bonnet in place, and slid the mittens onto my hands. He tied the ribbons at the wrist, and then laid me back down so he could fasten the poppers at the crotch, and slide the little satin booties on. He then took my hands, and told me to stand up and waddle to the mirror. Waddle I did, as the diapers had an huge center section which in no way would let me close my legs! He led me to the mirror, and let me see the prissy baby sissy I had been transformed into. It was a dream come true! My Dady and my sisters had made me into a beautiful sissy princess, and I loved it! As I was standing there, Daddy turned and opened the door, and there stood Linda and Mary! It suddenly hit me with full force that this had all been planned! "You guys planned all of this?" I managed to splutter out. "You, you, you al l knew?" Mary started to laugh, and then ran to me and wrapped her arms around me. She felt so soft, smelled so wonderful, I have to admit I had a hard on buried somewhere under all this satin, plastic, and cotton. "You silly girl," she giggled, "Of course we knew! You didn't really try so very hard to hide it now, did you? I mean, you would actually walk down the hall to the bathroom wearing panties, or one our of nighties, and you think no one saw you? We know what websites you visited, we know you like sissy things, and yes, sweetie, we even found the torn pair of plastic panties you tried to hide in your trash can. You see, Melissa, we know who you really are, and we are here to help our new sister." With that, Daddy scooped me up, and put me into my bed. To my lasting joy, I saw that my usual white cotton sheets were now pale pink satin, and as Linda pulled up the covers, Mary reached down and popped a pacifier into my mouth, and tied off the ribbon behind my head so it wouldn't fall out. I fell asleep, secure in my diapers, and secure in the love of a very extraordinary family. PS: If there is any call for it, I could make a part two, in my usual humiliating, kinky, and sexually explicit manner. Missy

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

2 years ago
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Saturday Morning Sissy

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

3 years ago
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Saturday Morning Sissy

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

2 years ago
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Revenge of The Sissy

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

3 years ago
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I Sissy

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

3 years ago
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The Farm School Sissy

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

2 years ago
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Becoming a Sissy

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

3 years ago
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What is a Sissy

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

2 years ago
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I would be the Young Sissy

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

3 years ago
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I Want To Be A Sissy

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

2 years ago
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My sisters their friends and me their sissy

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

4 years ago
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Young Sissy

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

4 years ago
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Rules for sissy

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

3 years ago
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Raised a Sissy

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

2 years ago
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Curiosity Spanked the Sissy

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

2 years ago
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Tweak Chapter Three Birth of a Sissy

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

3 years ago
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Beth and Sissy

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

2 years ago
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The Making of a Sissy

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

2 years ago
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Andrew the Unsuspecting Sissy

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

4 years ago
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Sunday Night Football Sissy

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

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

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

2 years ago
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A Happy Sissy

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

2 years ago
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The Blushing Sissy

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

3 years ago
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Degraded Sissy

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

2 years ago
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How to Build a Better Sissy

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

4 years ago
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Checkerboard Sissy

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

4 years ago
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Trucker Daddy Gets A Sissy

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

2 years ago
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Saturday Night Sissy

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

3 years ago
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The Blushing Sissy

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

3 years ago
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Home Alone Sissy

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

4 years ago
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Be a Sissy

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

3 years ago
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Sissy On Sissy

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

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 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...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

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

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

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

4 years ago
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What does it mean to be a sissy

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

2 years ago
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  • 44
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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...

2 years ago
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Miss Lindas sissy

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

2 years ago
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The Misadventures of the Worlds Worst Sissy

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

2 years ago
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First time Sissy

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

Transsexual
3 years ago
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Im Not A Sissy

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

2 years ago
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Richard the Sissy

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

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...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

3 years ago
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Irsquom my Wifersquos Sissy

My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so...

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