The Misadventures Of The World's Worst Sissy free porn video

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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 nothing else matters. After all, we are the remains of the boys you picked on in grade school, the ones who played hopscotch while the football game was being played, the ones who sang in the glee club and took ballet. We took home economics instead of gym. We took theatre instead of weightlifting. The truth is that this life is hard, even for the weakest of us who are inclined to live it. Take it from me, Calamity Jane. The worst sissy in the world. Okay, okay. I'm Janie Palmer. I used to go by Jake. Even then, I didn't beat my chest and claim to be a linebacker. I'm small, and I'm effeminate. I admit that I'm a sissy. I'm just not very good at it. I know, I know. You have read the stories of the sissies who take to it like oxygen. They cook, and it is as if Gordon Ramsay has visited their kitchen. They make elaborate meals, complete with sauces and desserts and baked breads. Me? I make a pizza. Sometimes, I don't even burn it. They clean, and it is as if they have turned into June Cleave. There are no smudges, no deposits. They never miss a spot. They are on a first- name basis with Mr. Clean. They're Donna Reed. Me? I try, but you certainly wouldn't want to eat off my floors. You might die a horrible death. I make the bed, and it is still so lumpy you would think there is a live raccoon underneath the covers. It's silly. Any Army soldier can make a bed. But I wash the sheets and I put them on fresh, and it still looks there was a wrestling match underneath. It is not neat. It is not delicate. I iron, and the garment doesn't look like it came from the dry-cleaners. It looks like it was wadded up and kept in the glove compartment overnight. The thing I routinely press is my left hand. Claire Huxtable never did that. And so it goes. I scrub a toilet, and there is a huge residue afterward that, for some reason, I did not see. I'm the sissy whose seams are always crooked, whose hair is always mussed, whose false boobs don't quite line up. I redo my makeup, and I end up with lipstick on my teeth. It's the reason that my mistress, Kelly, took to calling me Calamity Jane. I'm a splash of chaos, you see, with a dash of sloppy thrown in. As clumsy as I am, how did I get to be a sissy in the first place? Well, it wasn't that long a trip. I was always a little girly. But don't confuse gentle with graceful. Look, it's not that I don't like to wear dresses; it's that my hem is always out of kilter when I do. Our counselor has suggested that, even in the beginning, Kelly was looking for a relationship she could control. Maybe that's it. Like I said, I'm not the guy in the bar who you avoid in a brawl; I'm the one other wimps want to swing at. But it baffled me, too, one day when Kelly wanted to get coffee after our theatre group. She liked poetry, and we both liked Andrew Lloyd Webber, and before long, we were fast friends. I still thought she was out of my league, but one night she lifted my chin and kissed me. Her lips were soft and her perfume was sweet and she dressed in a swirl of colors and fabrics, and I fell in love with all of it. And things led to things, and she proposed at Moonlight Lake one night, and we ended up married. My mother was baffled. She thought I'd eventually get married to someone named Ralph. But she could see the strength in Kelly, too, and she knew that's where our strength as a couple would come from. Kelly and I were both into theatre, so we would act out plays, reading lines to each other. I could be Desdemona as easily as I could be Othello. I could be Marion as much as I could be Robin Hood. I could be Ilsa instead of Rick. Then one day, without saying a word, she started to apply makeup to my face. She worked on my eyes. She dabbed at my chin. She put lipstick on my face, thick, delicious, red lipstick. Then she handed me a dress, and our flip-flopped relationship took another step. And so we started role-playing. I still wasn't a transvestite, not really, not at that point. But it felt nice to be in lingerie, to be honest. I liked it. And we let our hobby take us over, as often happens in these relationships. It didn't feel wrong. It felt naughty. It felt different. It felt sexy. Some people take to things more than others. From the time I put on a dress, I liked wearing it. I just wanted to be Prince Grace instead of LaVerne, you know? Sissies are supposed to be dainty; I was the girl with the gravy stain on her maid's dress. Some sissies are Scarlett O'Hara. I was the girl who wobbled on her high heels. One day, Kelly brought home a new dress for me. It was a maid's dress, not fancy but functional. But I loved it. I got up and dressed the next morning, and I made her a breakfast she could almost eat. Runny eggs and burnt toast. Hell, I couldn't even fry coffee, as the saying goes. But she appreciated my efforts, and we started role-playing that way, too. I would call her Miss and she would call me Maid. We both smiled a lot over that. Oh, we weren't quite domme and sub. It was a play thing. I would wear the uniform, and she would "demand" a cup of tea and I would fetch and curtsy and she would wink. A notion seemed to be planted for us both, however. "Janie, you need to shave. If you shave, I'll let you wearing stockings. And if you wear stockings, you'll need a skirt so everyone can see. And if you wear a skirt, you'll need heels." Kelly said. I giggled. "Tell me, Janie, what is it about girls' clothes that you like so damned much." "It's a compulsion, same as any other," I said. "I like the feel. I like the way they caress your body differently than men's clothes. They hug you and make you feel...girly." Kelly smiled. "So what's your favorite. If you had only one garment to wear, what would it be?" I thought. I loved dresses, and the way the hems danced on your thighs. I loved panties, and the way they embraced you. I loved skirts. I loved heels. Finally, I looked at her. "The bra," she said. "Why the bra?" she said. "Nothing is more feminine," I said. "It holds in breasts, for those who have them, which is life itself. The straps are comforting. The lace on the cups is terrific." Kelly smiled. "You are such a pussy," she said, giggling. Hell, she should have thrown me away. Kelly is pretty and funny and adventurous, and even if she demanded control, she could have had whatever maid she wanted. For whatever reason, she wanted me. She thought my bumbling around and trying to be feminine was funny. Some women want to adopt the ugliest dog in the pound. Kelly thought I was the one who should wear her collar, so to speak. I was the worst sissy in the world. But I was her worst sissy in the world. So what if when I curtsied, I looked like I was a drunk falling over sideways? * * The night of the vampire: Look, if you want a testament to my awkwardness in this role, I can tell you this story. First of all, you need to know this: Kelly has a boyfriend. No, don't think less of her for it. She has a boyfriend because I suggested it, because I knew my little jellybean wasn't making her sing love songs, you know? I had read enough to learn of cuckold sissies, and I knew that if our marriage was going to last, she was going to have to find someone who could scratch her itch. It was just physics. At first, she wouldn't even talk about sleeping with someone else. But I convinced her that we were strong enough for this, and that it would enhance our feelings toward each other. Hey, what woman can say no when her husband, such as he is, is encouraging her to have sex outside the marriage? Any cuckold will tell you that eventually, she says yes. So Kelly met Scott at Lanahan's, a local bar, and they hit it off. They would go to lunch, or meet for a drink. It was all platonic in the beginning. But eventually, Scott wanted to step things up with Kelly. Kelly told him she was married, but it was an open marriage. She told him about Janie, and about our role-play, and about our interest in a third party. Scott was the first person outside my marriage who ever knew I was a sissy. Scott still wouldn't start anything until he met me. That was a good sign. He came over to our apartment one night -- we ordered out -- and he met me. I was in a soft blue maid's dress and my hair was in short pigtails. We sat and talked, about marriage, about vows, about cuckolding. He asked my sexual preference, and before I could think, I told him I was bisexual. I had never admitted that to myself, let alone to someone else. Kelly didn't flinch; somehow, she knew. He asked me to get him a whiskey and soda, and so I did. I got Kelly a white wine, and I brought them into the living room on a tray...and promptly spilled it on his lap. I tried to dab up the mess, then I realized I was rubbing his penis. He was gracious enough to laugh, probably because of Kelly. I looked down, and he was running his fingers over the back of her wrist. Scott and Kelly didn't sleep together that night. They had conversation and a light kiss or two, but it was obvious they were taking it slow. But I could tell Kelly liked him; hell, I liked him, too. That night, we lay in bed. I was wearing a black nightgown, and Kelly was wearing a blue one. "Are you sure about this, Janie?" she asked. "I am," I said. "Are you?" She nodded. "He's a very nice man," she said. "I'm not convinced I need a lover, but he'd be better than most." I twisted around. I missed her stomach. She scooted down on the bed and spread her legs. "You know what mama wants," she said. I nodded. I began to lick her gently. She grabbed my head and pushed it into herself more forcefully. She grabbed each of my pigtails, and she started to hump my head. "Ooooh, Scott," I heard her moan. Scott came over three times that week. He brought her flowers, and once, he brought them for me. It was as if he was wooing one of two sisters, and he had to take care of them both. Then, on Saturday night, Scott stayed. I could hear them thrash about in the bedroom, and I knew Kelly was no longer faithful. I decided I understood, even there was a rush of jealousy for a while. Then I heard Kelly call to me. I entered the bedroom, and they were naked. They smiled at me. "Clean me?" Kelly said. "Really?" "Please. I feel slimy down there." And so I swallowed hard, and I prepared to swallow harder. I climbed on the bed. I began to lick her, noticing the stronger taste of her vagina as their fluids mixed together. I licked for a long time, and my jaw began to to stiffen. Finally, she pushed me away gently. I was starting to rise when I felt Scott's hands. "Will you do me, Janie?" he whispered. And I did. I took him into my mouth, and I gently sucked, and it wasn't bad. It felt completely natural as I lay there, a dick in my face for the first time. But all the while I was thinking about the step I had just taken to being a cocksucker, and wondering what Kelly thought as she watched, and wondering what it all said about a sissy on her knees. And then I dragged my teeth against Scott's cock. It wasn't much more than that, a scrape maybe, something that barely broke the skin. But you know what men -- real men -- think about their penises. Scott screamed. He howled as if I was Dracula digging in his teeth, as if I was a cobra who finally caught a mongoose in its fangs, as if I was Eve taking a chomp out of the apple, as if I was McGruff taking a bite out of crime. Kelly gasped. Scott whimpered. Oops. I felt terrible, but not, I suppose, as terrible as Scott felt. I tasted a tiny bit of flesh in my mouth. I know you're suppose to swallow, but do you swallow that? Do you try to put it back and pat it down? What color wine do you drink with leftover foreskin from the penis? Oh, after his scab healed, Scott eventually forgave me. But it was a long time before he asked me to blow him again. I had to beg him, and I had to beg Kelly to plead my case. But in the days I lost my privileges, Kelly filled in just fine. ** The night of the midnight swim. It was in those early days, when my hair was growing out, that I wore blonde wig. In the right light, from the right distance, it meant I could pass well enough. Certainly for late-night at the pool. Officially, you were supposed to vacate the common pool by 10 p.m. but no one really paid much attention as long as you were quiet. Kelly and I would slip into the pool and we would steal a late-night swim, and maybe kiss a bit if there was no one there. On this night, there was another couple there. But there was plenty of room. Kelly and I went to the opposite end of the pool from them. After all, I was in a full women's bathing suit with my larger breast forms, and I didn't want to be discovered. But as time went on, we started to make conversation. I was lying on a pool float sipping a diet Dr. Pepper, and the couple -- Eddie and Cheryl -- were talking about Game of Thrones. Wasn't everyone? Anyway, Kelly decided that some horseplay would be fun. So we went underneath the water, and she rushed up and flipped my float. I went ass over elbows into the water. And I came up .... without my wig. I missed it immediately and grabbed my head. It was floating six feet away like a drowned muskrat. Evidently, I hadn't pinned it well enough, and now I was exposed. My own hair was matted down from the water, and my makeup was still on, and I looked like RuPaul at the car wash. "Is that ...a man?" Cheryl asked. "Is it some sort of fag?" Eddie asked. I stood there, waist deep in the water in a woman's bathing suit. My breasts were impressive, and I was sputtering. "She's....my husband," Kelly said. "It's cool. It's all right." Eddie stared at me. "Is it a he-she?" "Is it one of them," Cheryl said. "Guys. It's okay. She likes the clothes, that's all. Calm down." "Damn," Eddie said. "I'd fuck her." Cheryl harrumphed. "Well, I would," Eddie said. "But I'd fuck you first, baby. I promise." Somehow, that seemed to mollify Cheryl. She reached out and touched my breast forms. They came loose from my chest, and she looked at them dumbfounded in her hands "I might like to see that," she said. Kelly looked at me, as if asking a question. I shook my head no. "You know, we could have some fun," Kelly said. Cheryl giggled. "Why doesn't she suck your dick?" she said to Eddie. "Nah," Eddie said. "I want her ass. You never let me do your ass." He was touching my back now. He had heavy tattoos on his arms. I shuddered. All because of a wig I hadn't attached properly. Cheryl pulled down my shoulder straps. She worked the suit downward until I was naked. Kelly was now holding my breast forms to keep them from floating away with my wig. There, in the shallow steps of the pool, I had anal sex for the first time. Eddie was of average size, but he was eager. It didn't take him long to work it in. It burned a bit at first -- doesn't it always? -- but then it was delightful. I decided I like my off-ramp just fine. "Look at her little balls bounce," Cheryl squealed. "I think she likes it." I moaned. "I think she loves it," Kelly smiled as one of my breasts floated past. * * The night my boobs caught on fire: In the Sissy world, it is completely allowed for a girl to slave over a hot stove all day to make her confidantes dinner. But if that same sissy were to fire up a grill, there are men who would clear their throats and roll their eyes. Only real men can grill, the argument goes. Fortunately, Kelly didn't think so. It really wasn't that complicated to make burgers on the grills. Or steaks or chicken, for that matter. But in those early days, I was really, really into having big breasts. It's a weakness. What can I say? So there I was, grilling on the patio. And, yeah, you guessed it. I got to close to the flame. My breasts started smoldering, then smoking. Then there were flames, dancing in front of my face. Think of it: I had two towering infernos right on the front of my dress. I couldn't feel the pain, naturally, since my forms were artificial. But then there was heat, and I shrieked as sissies do. Scott tackled me there, and he rolled me in the grass beside of the patio. I suffered minor burns, but nothing more. After that, Kelly became convinced that I needed real breasts that I could feel, even if they were smaller. She took me to the doctor, and very clinically, he went over my options. Implants, which I couldn't feel as well. Hormones, which would drain my ability to get an erection. Scott had taken to singing "Smoke gets in your eyes" or "Fire." I had a hard time laughing. But I think it was time to turn me over. My front side was done. * * Then there was the night I needed an eyepatch: This happened before Kelly and I were married. I had the worst struggles with my makeup. I know, I know. Some of us are artists, and after a few tries some of us can handle makeup as well as their older sisters. But I felt like Bozo the Clown. My lipstick was always too garish. My eye makeup looked like I was trying to scare small children. One night, I was practicing. I was trying to have a lighter touch with my eyeliner, which looked like a punk rocker's. I was trying to master mascara. Kelly came in, saw me, and suggested I was so cute, I could end up with another guy up my ass that very night. "Maybe even me," Scott said. I jerked, and I jammed the mascara brush into my eye. You know the old saying that a particular discomfort is still "better than a jab in the eye with a sharp stick?" Well, I'm here to tell you that in most cases, they're probably right. My eye was red from blood the next day. I was cute, I tell you, with one devil's eye and one normal one. The doctor said I had to wear an eyepatch for a month. I felt as if I was signaling for a left turn. Kelly took to calling me "Maid Cyclops." One eye and half-sense. Worked for me. * * The night I laid an egg: Kelly wanted to show me off. Don't all mistresses? So she invited our theatre group, and some people from her work, and some of our casual friends, and she had a large dinner party. Guess who was serving? It made sense, Kelly said. This way, it would be like ripping off a Band-Aid. One uncomfortable moment, and everyone would know about me. One blush, and all of our friends, and some of our family, would know that I wore dresses. Don't get me wrong; it was daunting. There was no turning back. Forever, in the minds of those who knew us, I would be a sissy. Kelly tried to calm me down. She handed me a small, jewel-covered butt plug, thinking that would take my mind off of the evening. And it worked. It was jammed in good and tight -- Kelly referred to it as Thor, my boyfriend. But it felt nice when I walked, and it added a sway to my hips. Still, though, I was nervous. I was about to open the door to the world. Coming out is never easy no matter what your nature, is it? I was sweating. I was breathing too fast. I was dizzy. So Kelly relaxed me. I mean, she really relaxed me. She stripped off my panties, and she began to play with my dicklette. Again, I'm not as big as Scott, but it felt nice nevertheless. She played underneath the hem of my dress for 15 minutes until I came, then she took a wet towel and cleaned me just before the doorbell. I jumped up to answer the door. It was Millie and Andrew Roberts, from the theatre group. They cooed and commented, telling me that I should have been dressing for a long time. I smiled and crouched in my lame curtsy, looking like a chimp trying to give birth. The evening went on, and you know, it wasn't bad. I didn't know if Kelly had told everyone, or if everyone just figured there was something feminine about me. I served drinks and appetizers. I was happy. This was going well. And then it happened. My God, it happened. I was bringing a tray of drinks across the living room, and I felt it slip. My butt plug. Before I could rescue it, it squeezed out of my rectum and, without panties to stop it, it clattered to the floor. I stood there, shame-faced, with the plug lying behind my feet. "What is that?" someone asked "Is that a dildo?" "No. It's a plug. It goes in your ass." "Did that come from Janie? Oh, my God. It did." I was mortified. It was one thing to wear a dress, okay? It was something else to stuff an object up your ass and wiggle. It wasn't a carrot, or a candle, or something for which there are other uses. This was a plug, designed for the butt, and everyone knew it. My God, what a pain in the ass. * * The night of solitary confinement: As it turns out, Kelly was embarrassed, too. Part of it was that she had been the one to remove my panties. But the bigger part was me exposing part of my sexual activity to her friends. They might have figured I would have worn a plug, but no one was going to say it out loud. Not till it fell out of me onto the floor. So Kelly got it in her mind to cover me up. She bought a better plug, one that locked. And while she was buying lockable, she bought something else. It was a chastity cage, silver and bright. It fit over my penis like a mini-prison, locking away any thoughts of sexual release. It looked ... cute. Tiny and glistening. No matter how hard one tugged on it, or tried to remove the lock, it stayed put. Kelly put pink panties on over it. She wasn't going to have another butt plug incident. If I didn't think too hard about it, I liked the look of it, a little bottle cap covering mini-me. But I had read the stories; I knew about women who forgot about their men for weeks a time. You are supposed to unlock it every couple of days for cleaning, but some evil women seemed to like them to stay attached for weeks, even months. Of all of the dungeons in all of the castles all over the world, this might have been the worst torture ever invented. But I wore it the first day without complaint. I wore it the second without comment. But by the third day, my eyes were crossing. I needed a pardon. I needed to join the early release program. So I went to Kelly's jewelry box, and the key wasn't there. I looked on the ring with her car keys, and it wasn't there. I looked in her night stand, and it wasn't there. Where in hell could it be? I was going crazy by this point. If I could have, I would have cut it off (the cage, not the cock). "Kelly," I finally asked. "Where...um, where is my key?" She burst into laugher. "You lost your key? Scott! Janie lost her key. Her pee-pee is in prison, and the warden just went on vacation." Scott laughed. He had me pull down my panties so they could look closer. And there it was, shrunken and forgotten, a little piece of flesh in a tube. He flicked the lock. The No. 1 thing we all need, even more than food, even more than air, is hope. But without a key, there is no hope for a cock-cage wearer. You think about going to the doctor, and this is on your dick. You think about calling a locksmith, and the shark cage is on your pecker. You are part sissy, part machine, part Borg. "I wonder how long a guy can live while shackled," he said. "We might as well have made it a vagina," Kelly said. "This is too funny." And so the two of them sat around, making fun of my plight, calling me the Birdman of Alcatraz or the Man in the Iron Mask. The joking went on for most of an hour. At one point, Kelly took her cell phone out and began to take pictures. "I have to send this one to your mom," Kelly told me. "You've gone to Shawshank." I started to cry. Hell, I'm a cryer. Everyone knows that about me. But I felt lost, and abandoned. I was going to have to go to my doctor and have him cut it off. (Again, just so we're clear. I was talking about the cage, not the cock). Then I looked up, and Kelly had both keys, dangling them from her fingers. It sounded like a choir of angels. "You left them on the counter, Calamity Jane," she said. "I picked them up for you. It's just like you to forget something like this. What are you again? Oh, yeah. You really are the worst sissy in the world." I sniffled. I needed to blow my nose. Still, the key had been found. Hallelujah. Someday, some way, I shall be released. * * The night of the wedding singer: Scott's brother Todd was getting married to a sweet girl named Tanya. Scott was going to be the best man. Kelly was going to be the matron of honor. I was going to stay home where it was safe. But adults scatter, and Tanya had a bridesmaid back out on her. Kelly volunteered me, which I thought was a horrible thing to do. Still, I would get to wear a bridesmaid's dress. What sissy doesn't long to do that? And so we showed up at the wedding. Kelly had assured me that no one would know me, and that I could pass just fine, and we'd dance and laugh and tell stories. It would be like the wedding crashers if you ignored the fact I was wearing a dress. By now, however, you know the two stages of my luck: Bad and worse. Another usher for the wedding, Paul, kept looking at me. It was like he was studying modern art, but there was a part of the picture that didn't make sense to him. Finally, he grinned. He elbowed the guy next to him and said something. That guy looked at me, too. I had been found out. I approached Kelly and whispered that we had to go. She was drinking hard, however, and she laughed off my concerns. No one could know, she said. We were strangers. But, it turns out, Paul had gone to UC, and he'd had a science lab with me. And, despite the odds, despite the clothes, despite the makeup, he figured me out. It was just rotten luck. I wanted to hide. Paul, however, wanted to dance. So he grabbed my hand and he led me to the dance floor. "I haven't seen you since UC," he said. "You've changed." He looked at my breasts. "Are those new?" he said. "Paul, please don't cause a scene. It's Todd and Tanya's wedding." I whispered. "But how much fun would it be if they found out one of their bridesmaids was a really a guy?" Paul said. "I don't think they'd ever stop talking about it. It would the story of a lifetime." I sighed. "I'll do anything if you won't make a scene," I said. He grinned. "I've never gotten a blowjob from a tranny," he said. "Paul, that's a vulgar word," I said. "We're trans women, okay." He laughed at me. "You have tits and you're wearing lipstick and a dress and heels," he said. "And you want to lecture me on what I say?" "No, Paul," I said. "I'll be good." "So do you still have a dick?" I exhaled. "Yes, Paul. But it isn't large." "I wouldn't imagine so," he said. "Most guys with little dicks try to turn into girls, don't they?" "I ... I guess," I said. "Okay, here's what's going to happen. There is a men's room just outside of the reception hall. You're going to meet me there in five minutes. If you don't, I'll tell the world. I'll be the town crier." Was there a way out of this? I looked at Scott, who was across the room laughing with Kelly. I slunk out of the ballroom and walked toward the bathroom. I hung my head. Was there a difference between rape and coercion? Did it matter? I knew I had to do this. I wiped a tear. I had screwed up a lot. But this be my fault? It was just the wrong girl in the wrong place. I opened the door. I stepped inside. Paul was waiting, sitting on the counter, his pants around his ankles. In another life, in another place, Paul could have seduced me. He was young and good-looking, and he had that bad-boy grin that I loved. But this was wrong. I dropped to my knees. * The night my wife got engaged: It was Thanksgiving, and I was serving to Scott and Kelly and Todd and Tanya. It was a cozy dinner. Todd and Tanya still thought I was just the maid. Kelly and Scott didn't tell them different. I was serving the turkey on a large silver tray -- with a side gravy boat -- and the conversation continued. Tanya was talking about how much she liked having a husband. She asked about Scott, and whether he was a good husband to Kelly. And Kelly grinned and said that Scott was the best husband in the world. She said she hoped they would have many more years of married life. I felt the room spin. If Kelly was going to marry Scott, it meant that Kelly would have to divorce me. That meant I would be ousted so she could replace me. I felt dizzy. Then I dropped the turkey. The tray clattered to the floor, the stuffing and gravy splashing high into the room. I slumped to the floor in the mess, the tears flowing. "Janie!" Kelly gasped. "Janie, are you all right?" "There goes dinner," Todd said. "Clumsy maid," Tanya said. "Calamity? Are you all right?" Scott said. "You're... you're going to marry Scott?" I asked Kelly. "Whatever are you talking about, Janie?" Kelly asked. "You said ... you said you wanted to be Scott's wife for many more years," I said. "You're throwing me away." "Silly, I was just talking," she said. "In a way, Scott is my husband. He's both of our husbands. Baby, noone is going to throw you away. We're married. We're going to stay married forever. But I think of Scott as the husband in this household, and we're his wives. It's like polygamy, baby." Todd's mouth was open. Tanya's hands were on her cheeks. They were finally getting a glimpse inside the true dynamics of our relationship." Kelly kissed me on the forehead. "I phrased it wrong, Janie," she said. "But I swear, no one is being replaced. We're a family. I love you. Scott loves you. And I'd love it if you could clean the turkey off of the floor." I nodded. I was sitting on the floor in a pool of gravy with a ruined turkey in my lap. Scott picked up a dinner roll and threw it at me. I laughed. Scott softly kissed me on the lips, right in front of his brother and his wife. "You're not the third here," Scott said. "I am. But we need the other two to complete our circles, okay? We aren't throwing anyone overboard." I sniffled. "There are some steaks in the fridge," I said. "I can cook those." Scott chuckled. "No, you can't. You're Calamity Jane." "Typhoid Mary," said Kelly. "You're Mrs. O'Leary's cow," Scott said. "Maleficent." "Bloody Mary." "Cruella DeVille." The three of us were laughing now, while Todd and Tanya looked on with bewildered looks on their faces. Scott made the steaks. Kelly made a salad. Me? I made the mess. It's what I do. * The night of the Sugar Plum Fairies: Christmas was approaching now. Once again, Kelly wanted to demonstrate her considerable hold on me. So she went to Leather, a bar on the east side of Cincinnati. It wasn't hard to tell my preferences, if you want to know the truth. I was wearing a pink princess dress. Kelly was leading me by a leash attached to my collar. I had on high heels and a tiara. Rings were on my fingers and earrings dangled on either side of my neck. We moved through the bar. I was wearing my cage and my plug. Both were locked securely into place. A stranger lifted his glass to Kelly. "Mistress," he said. "Merry Christmas." Kelly smiled and nodded imperiously. She loved having her superiority acknowledged. "And to you, sissy boy," he said. I curtsied. I knew my place. Kelly sat on a stool, and I knelt beside her. I couldn't see over the bar, but then, why did I need to? "You here to sign up?" the man asked. "Sign up for what?" Kelly said. "For the parade," he said. "For the Nutcracker play later on." Kelly grinned at me. The thought of Calamity Jane trying to dance in step with other, more artistic sissies amused her greatly. Imagine a hippo in the middle of flamingoes. "Tell me," she said. There was going to be a Sissies on Parade in the Prize March earlier. There was going to be a play later on. Like all sissies, I was invited to audition for them both. But, the stranger said, sissies are almost never turned down. There was always room in a parade, They could always use another backup dancer. Kelly took down the information. "You're going to have so much fun, Janie," she said. My eyes were wide with terror. Hell, I knew what a klutz I was. Asking me to dance in heels is like asking a moose to ice skate. But, as always, it was my Mistress' call. I lowered my head and imagined the trouble ahead. As predicted, there was always room for another dancer, another marcher. I didn't win my spot with grace and beauty at either level. But on Christmas Eve day, I walked beside the float and waved to the straights in the crowd. I smiled as onlookers yelled "fag" at me. Then, that night, there was the play. Have you ever seen a kid's play where the one clumsy kid is a half-beat behind the others? That was me. I was a moose chasing a butterfly. I was in my tutu, dancing beside of all other girls. But they were elegant. I was clopping around like a rhino on acid. And you know what? It didn't matter! I was grinning as I danced, lost in the music and moment. It finally dawned on me that being feminine had nothing to do with grace. It had to do with self-identification. It had to do with attitude. I was a sissy not because of talent; I was a sissy because I wanted to be. I needed to be. Perhaps there are others like me out there, ugly ducklings in the middle of swans. That's okay. Nicer makeup doesn't make you girlish. The fact that you have to wear it does. I was a sissy. And it was glorious. Right up to the moment I knocked over the life-sized wooden soldier. © 2019 by Cassandra Morgan

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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...

1 year ago
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Mrs Grant and her new Sissy

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

3 years ago
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New Little Sissy

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

2 years ago
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Its Hard For This Sissy

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

3 years ago
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stepson becomes moms sissy

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

1 year ago
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My Sisters Sissy

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

3 years ago
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A Nasty Daddy gets a Naughty Sissy

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

3 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...

3 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...

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