A Very Sissy Love Story free porn video

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A Very Sissy Love Story by: Missy Satinpanties I guess I've always been bisexual, if not completely gay. I mean, in high school, I lusted after the right girls, and wanted to get into their panties like every other boy, but when I looked at the porno mags we had, I always gravitated towards the girls who looked kind of innocent, and were wearing soft, lacy lingerie. And yeah, I did wonder how all that soft, slippery lingerie felt. A naked girl really didn't grab my attention, at all. And, if there was a picture of a guy getting ready to have sex with some hot chick, I also quietly, but thoroughly, checked him out. At first, there was no fixed idea in my head that I wanted to have sex with a man, but that came on strong later. My first experience with a man came when I was a Junior in High School. I had joined the swim team at the local Y, and just sort of kept going, even though I wasn't any kind of star, and it changed my life totally. I was seventeen years old, would turn eighteen in January. Because of when I started school, and the fact that I took some courses at the local community college, this could be my last year in high school if I wanted to graduate early. On the swim team, I was the guy who never won, but could usually be counted on for a third or maybe a second, and a few points. I really wanted to do better, and asked for some help. The assistant coach asked me to stay after practice one chilly Friday in November Friday in order to work on my stroke. He had me swim a length, and he would criticize and correct, I would swim another length, he would again correct. Finally, Coach Norton jumped into the pool to try to work on my kick. He had me hold onto the gutter, while he manipulated my legs. His hands on my thighs brought about a reaction that I usually reserved for glossy porn magazines. After a few minutes, he "accidentally" brushed my crotch, and made some joke about the bulge. He brushed my crotch at least 4 more times, each time moving his hand a bit slower. When I didn't object, he got much bolder, and cupped my erection through the thin nylon Speedo suit. Just a few minutes later found me naked in the trainer's room, lying on the padded table with Coach Norton giving me my very first blow-job! I was in heaven as he kissed and licked my balls, ran his tongue up my shaft, and then took me into his mouth. I came almost immediately and also felt very guilty. We both dressed, silently, and then Coach Norton and I talked about what had happened, and we both finally agreed we wanted it to happen again. Each Friday, I stayed late at the pool, working with Coach Norton, and while my stroke did get better, it was the sessions in the training room that really saw my "stroke" increase. The first few times, I was just a passive recipient, but the third week, I became an active participant. On the table that night, my right hand seemed to move on its own, and gently cupped the coach's balls. I ran my hand up and down his shaft, feeling the heat radiating from his cock, feeling it grow in my hand. I looked into Coach's eyes, and he just nodded. I slid from the table, and dropped to my knees in front of him. I just stared at my first cock, and then slowly wet my lips and took the head into my mouth. As soon as I did that, a switch seemed to go off in my head, and I pushed forward, wanting to swallow as much of this cock as I could. After much gagging and adjusting, this wonderfully warm, hard cock was sliding in and out of my mouth. Coach Norton held my held gently, caressing my hair, and giving me encouragement. I felt his cock swell in my mouth, and instead of caressing my head, he grabbed it, forced his cock down my throat, and filled my mouth and throat with his cum. Afterwards, he gently lifted me to my feet, and then kissed me on the lips. I wasn't sure about this, but within seconds, my arms were around his neck, and I was eagerly kissing this man, finally setting in concrete the fact that I wasn't bi, I was very gay. The next Friday saw a shift in our pattern. During the week, I thought about our encounters, that hard cock in my mouth, and that kiss. I thought a lot about that kiss. While he was holding my head, and then when he stood me up and kissed me. I felt so...well...like a girl. I felt submissive and girly, At Thursday's practice, Coach Norton casually, but quietly asked me if I wanted to go to his house after practice the next night. He asked me in passing, and about 5 minutes later, I told him yes. That night, I gave my mom a BS story about where I would be, and spent all day Friday with a hard-on and barely paid attention to the world around me. Once in the locker room after school though, we were told that something was broke and the pool heater was dead, so no practice. Our head coach left for home, and Coach Norton asked me if I would help him move some things in the office. The rest of the team left, and after being sure that we were alone, I went out the front door to my car, while Coach Norton went out the back and got his. As I slid into my old Civic and pulled out to follow him, I had the feeling that a whole new chapter in my life was about to open! I knew that Coach was divorced, and that he had a 19 year old daughter who graduated last year. I also knew that he taught the advanced computer programming class, along with a few general computer courses at the school. That was really all I knew about him. We got to his house after about 20 minutes, pulled both cars into the garage, and got out. He unlocked the kitchen door, and again, without any talking, he held the door for me, and we went inside. Once inside, he gave me a kiss on the cheek, and asked me if I wanted a tour of the house. It wasn't a large house, but it was nicely decorated with a big flat screen TV, large comfy leather chairs, and a sofa in the living room, and a small, but very tidy kitchen with a small table and 4 chairs. Next, he showed me his neat and tidy bedroom, and then his daughter's room, or at least the room his daughter used when she was here. It turned out that she was here every other month or so, when she wasn't in school. It was also the room she grew up in. Unlike the rest of the house, though, tidy was not the word to use here. Posters were stuck up on the wall in a chaotic fashion, and even though she had not been there in weeks, there was a pair of jeans draped over the chair, and various pots and tubes of makeup spread across the top of the dresser, and the bed was a rumpled mess. But, what seemed to catch my eyes was a pair of pale blue panties draped casually over the bed post. I wanted to touch them, to feel them, to sniff them, so badly. We then went back out to the kitchen, where he ordered a pizza to be delivered, and then poured 2 glasses of red wine. He told me that if I didn't like it, he had soda, also. I tasted the wine, and found it dry and it kind of made my mouth pucker, but I told him it was fine, and by the time the pizza arrived, and I had been though 2 glasses, it was very good. During the time we spent waiting for the pizza, we talked. We talked about swimming, his daughter, the house, and finally, about us. I admitted to really enjoying my first blow job, but that what had really sent me into orbit was how submissive and feminine I had felt when he held my head and forced his cock to the back of my throat, picked me up, and then kissed me. I blushed, and told him I wanted to be his little girl. Coach just laughed. "I don't want a girl, I want you! But, maybe you could be my little sissy?" "What do you mean," I asked. "Finish your dinner, and I'll show you," he replied. Soon we were done with the dishes in the sink, and without another word, he lead me to the living room. "Now, Mike," he began, "I have been thinking of this night now for a month, and I want to know if you are willing to go along with my little fantasy. I think I can make a few small changes, to what I was planning, and that will make us both be very happy. Shall I explain?" Eagerly I told him to go on! "Okay," he began, "I'm gay, and like to be in control, and since you have told me you like being submissive, that should work, right?" I nodded my head, not really sure where he was going with this. "I want to make love to you while you are tied up and gagged, do you understand? I thought for a moment, swallowed, and slowly told him to go on. I think the bulge in my pants would have answered for me if I hadn't said anything, though. He then took me by the shoulders, kissed me gently on the lips, and told me to take off all of my clothes. Even though it was warm in the house, I began to shiver as I slowly removed my pants and shirt, as though I had no will of my own. Once I had all my clothes off, Coach just looked me up and down. Here I was, a skinny kid with longish hair, but barely any hair on the rest of my body, and a stiff cock, standing naked in a man's living room, knowing, or at least thinking I knew, what was coming next. Coach reached out, and took my hand, looked me in the eyes and gently told me to call him Tom, and then led me to his daughter's room. There, he told me to sit on the bed, while he rummaged around in the dresser, and then in a large box on the floor of the closet. While he was rummaging, I picked up those soft panties, and ran them through my fingers, and across my cheek. They were heavenly! Finally, with a triumphant, "Aha!" he stood up, and turned around. I quickly dropped his daughter's panties, hoping he hadn't seen me. "These things were my daughter's when she was about 12 or 13, and they should fit you nicely. The last time she was here, we went through her stuff and threw out a lot, and this box was to go to the dump, too, I just never got around to it. He then held out his hands, and showed me what he had found. I was staring at a pair of pale yellow satin panties, with ruffles around the leg openings made of the same material, and three rows of white lace across the bum. He also had a matching bra, with some lacy touches, and a little white satin bow in the front. He laid these on the dresser, as he explained further. "My daughter was in a state fair pageant, and this was one of the outfits that she wore. Instead of swim suit and evening gown, they did swim suit and fancy square dance costumes. I think these should just about be perfect for a little sissy like you." He smiled, blew me a kiss, and went back to rooting in the closet. He stood up a moment later with a pair of white high heels, set them on the dresser, and then dove back into the box, and pulled out a pair of little white nylon ankle socks with a cloud of yellow lace trim around the top. I stood up, and moved across the room in a daze. I picked up the delicate satin panties, and ran my hand over the soft material, then rubbed them against my face. "Would you like to try them on?" Coach, I mean Tom asked gently. Again, in a daze, I could only nod my head. I sat down on the bed, and slid those soft, heavenly, and feminine panties up my legs. I stood up again, and pulled them up around my waist, reveling in the tight softness around my waist. Tom then came to me, and told me to hold my arms out. He slid the bra up my arms, turned me around, and fastened the catch at the back. I was now wearing a bra and panties that really looked better suited to a 6 year old in one of those beauty pageants you see in the documentaries on the Discovery Channel. Tom asked me to sit back down and told me to point my left foot, and slid a slippery nylon anklet and a shiny white, high-heeled shoe on my foot, and then buckled a little strap across my instep. He repeated the process with my right foot, and then helped me to stand. The shoes had rounded toes, and looked like the black shoes that a little girl would wear. Mary Janes, I think they're called. They were rather tight, and even though the heel was only about 3 inches tall, I could only stagger instead of walk in them. Now, Tom handed me a sheer white robe that he said had belonged to his wife. I decided quickly that this robe wasn't designed to conceal anything, or to keep you warm. After I practiced walking a bit, and could navigate without falling down, Tom took me by the hand again and led me out into the hallway, and then to his bedroom. As I made my way to his room, I was aware of the bra straps digging into my shoulders, the ruffles around the legs of my panties tickling my thighs, the soft panties as they rubbed against my bum, the tight, restrictive shoes, and the diaphanous gown floating over all. I think I was walking two feet above the carpet. While I stood at the foot of his bed, he went into his own closet, and brought out a box. "I hope you like these, Mike, I bought this all especially for you, not even knowing if you would consent to wear it for me." He said. "But, you know, we have a little problem," he went on," I can't call a cute little sissy like you Mike anymore, can I? I think maybe Michelle, or "Missy" for short would be a good name, what do you think?" I nodded eagerly, and looked at the box to see what kind of goodies he had for me. The first item looked like a pair of white mittens. In fact, they looked exactly like a pair of white satin mittens, with no thumbs. He took each hand, told me to hold my fingers together, and slid each mitten on my hands, and then buckled them onto my wrists, with what looked like two white leather straps from a lady's watch. I now found that there was a layer of thick material between the inner and outer layer of satin, which made my hands completely useless. There was also a shiny silver hook on each one that confused me as to what they were for. I was soon to learn. Next, Tom brought out a white patent leather collar with white lace trim top and bottom. This he buckled around my neck, not tight enough to hurt, but I knew it was there. Finally, he took each hand, and brought it up to my neck, and then I knew what the hooks were for, as he fastened each wrist to a ring at about the seven and five o'clock position (assuming the front of the collar is the twelve o'clock position) I was now in lacy little girly lingerie, heels, with my hands immobilized in satin mittens, buckled to a collar around my neck. I was scared to death, excited, and curious, all at once. But most of all, I was turned on. Tom gently took my face in his hands, and kissed me on the forehead. He told me that if anything happened that I didn't want to happen, I was to either say the number three, snap my fingers three times (In these mittens??), or stomp my foot three times, and everything would stop. As he held me, I told him I understood, but really, could think of nothing except that I was now a sexual object, here to fulfill this man's sexual desires, and it was all out of my hands. I was helpless, submissive, and never wanted this to stop, no matter what happened next. He began to kiss me, first on the forehead, the light little kisses on my eyelids, and cheeks, finally kissing my lips. At first, they were gentle little kisses, but then they got more urgent, until finally he was holding my head, and pressing his lips hard against mine, his tongue exploring my mouth. I almost passed out with the pleasure of it all. He stepped back, and slowly took his shirt off, revealing his strong, hairless chest and stomach. Ever so slowly, he kicked off his shoes, and lowered his pants, now just standing in front of me in a pair of black cotton bikini underwear. I could see his cock bulging the front of the bikinis, and thought about this thick, 8 inch cock, and how good it felt in my mouth. Tom walked over to the bed, and came back with a pillow, which he placed on the floor in front of his feet. Slowly, but firmly, he placed his hands on my shoulders, and pushed me down, until I was kneeling on the pillow. "Missy," he began, "You are now mine. You are my lover, you are my slave, you are my slut!" Show me how much you love me, and kiss my cock through my underwear!" Earnestly, I began to kiss and lick him through the cotton, kissing the skin of his thighs, and nuzzling his crotch, inhaling his musk. After a few minutes of this, he lowered his bikinis, and his erect cock sprung up and slapped my chin. Without any direction, I began to kiss his cock, and to lick the shaft and his balls, using my tongue and lips with all the skill and passion I could muster. I took the fat, purple head into my mouth, and swirled my tongue around it, and then began to suck as hard as I could, releasing, and then sucking, each time taking a bit more of that wonderful cock into my mouth. When my face was jammed against his stomach, he took my head in his hands, but this time, instead of holding me, and fucking my mouth, he pushed my head away. I just looked up, and asked him what was wrong. Tom didn't answer me, just took my arms, and stood me up on those unsteady heels. Kissing me again, he told me to stand very still, and not look around. He went to the box again, and took something out. I felt his hand on my ankle, as he told me to spread my legs. A cuff of some kind was wrapped around first my left, then my right ankle, and then something was clipped onto the cuffs. "What I've put on you, Missy dear, is a spreader bar, that forces you to keep your legs spread." I had no idea of why he wanted to do that, but I have to admit to really being turned on by the whole scene of being feminized, and completely helpless. Well, not completely I guess. I mean, I could still use the safe word, tell him to stop, scream for help, I suppose, if I really had to. He was now standing behind me, stroking my hair, running his hands over my butt, and stroking my nipples through the yellow satin bra. I had never known how sensitive a boy's nipples were, but what he was doing felt sooo good! He would gently pinch and twist them, then stroke them, and I never wanted him to stop! Next, he moved his left hand up to my face, and began to stroke my cheek. His finger went into my mouth, and I began to suck on it, Then, he put a second, and a third finger in my mouth, and gently pried it open. As he did this, he brought his right hand around and forced something large and kinda soft into my mouth. Quickly, he grabbed the straps that dangled from this thing, and buckled them tightly behind my head. I was now bound and gagged, in lingerie, with my legs held open. I was scared! While my tongue explored this intruder, Tom came around in front of me, and told me that I now had a rubber, penis shaped gag in my mouth, and he could do whatever he wanted to me, as I could neither yell out, run away, or use my hands. I was getting more scared by the moment. He then told me he could whip me, use a cane, or do whatever he wanted, as I was his slave. Now, I was crying! Tom began to laugh, and told me not to cry. "Isn't this what you wanted, Sweetheart?" he asked me softly. You wanted to be a helpless little sissy-boy, and I have wanted a submissive little boy for so-o-o long! But don't worry; none of those terrible things will happen to you, at least not tonight!" With that he unhooked my wrists and ankles, and then unbuckled and removed the gag from my aching jaws. With that, he took me into his arms, and hugged and kissed me, stroking my hair, and nuzzling my neck. I was very confused, but could only respond to his loving ministrations. After a few, too few, minutes, he held my shoulders at arm's length, and told me wanted to talk, seriously, for a moment. After removing my satin mittens and the leg spreader, he took hold of my hand, and we went back out to the kitchen, with me still toddling awkwardly on my heels. He sat me down at the table, and busied himself making some coffee. When it was ready, he asked me how I liked mine, made us each a cup, and sat down opposite me. "Mike," he began, "I want you to be my Little Missy, if you want to be. Now, before you answer, let me explain a few things to you. If you agree, you will be bound and gagged whenever I choose." "I wasn't sure about the lingerie, but find I love it on you, and will be buying some outfits of your very own. I want you to understand that you will wear what I want, when I want, both inside and outside of the house. I also want to tell you now that you WILL be spanked. Not because you deserve it, but because it turns me on. I will punish you, bind and gag you, dress you like my personal Barbie doll, humiliate you, and degrade you. But most of all, I will love you. Now, I'm going to give you while to think about the whole idea." He then directed me to remove the lingerie, and put my boy clothes back on. "I don't want your thinking colored by anything. This is something that you have to really think about. Think about how you felt when we were kissing, when you were sucking my cock, but also, think about being helpless, truly helpless, and thinking you were going to be hurt. I'm going to go into the bedroom and read for a while, let you sit here and think. It's now five after six. Say, I give you until six forty- five? At that time, you can pick up the panties, bra, and the peignoir, leave, and there will be no hard feelings, and I will understand completely. Or you can put them back on, along with your little socks and heels, and come into the bedroom. It is your choice, Mike, but remember, it is an all or nothing choice." I sat there for a few minutes, sipping at the coffee, and thinking. I ran my hands across my jeans, feeling the rough material, and contrasting that to the delicate softness of the satin panties that were sitting on the counter, and which had so very recently covered my little sissy bottom. I thought about the panic that I had felt when Tom told me I could be caned, or beaten, and could do nothing about it. I thought of the pain in my jaw from the gag, the soreness from the tight shoes, and of having my wrists pinned to a collar around my neck, and weighed all of this against the softness of the panties, and made my decision. IN THE BEDROOM: Tom heard the kitchen door going into the garage open and close within about 5 minutes of leaving the kitchen, and he sighed. "My Missy is gone," he thought to himself. Mike was such a beautiful boy, and the thought of him restrained and dressed in sissy lingerie made him so hungry. But, he knew the decision was Mike's, and while he hated the choice, he had to respect it. He just sat there on his bed, an unread magazine in his lap, and a glass dark with whiskey in his hand. He sat there for another ten minutes or so, and was just going to get up, and put the coffee cups in the dishwasher, straighten up the kitchen, and watch some television, when he heard the garage door open and close again. He listened, wondering whether he should call 9-1-1, or what he should do, when he heard a wonderful sound. The sound of high heels clicking on a tile floor carried clearly though the house, and then the bedroom door opened, and Mike, his own dear Missy, was standing there in his new lingerie and heels, smiling shyly at the older man. Setting his glass down with shaky hands, he started to get up, but just sat there, not daring to move, lest this vision of loveliness disappear again. ME AGAIN: I had indeed made my decision, and made it quickly. I had stepped out into the garage to privately practice walking in these shoes a little bit. Now, I walked, no, I minced, over to Tom, and knelt down beside him, draped myself over his knees, smiled up at the confused man, told him I was ready for my first spanking. Tom's hand landed again and again on my poor pantied bottom, and I squirmed and wiggled, trying to avoid each smack. After about 20, not very hard smacks with his bare hand, I was crying and trying to get my hands over my sore bottom. Tom had grabbed my arms, and held my wrists together in one hand, while he delivered a few more blows, and then it was all over. He stood me up, and held me like a lover. I wrapped my arms around his neck, and whispered in his ear that I was his Missy, forever. We ended up in bed, cuddling and kissing for the longest time, and then worked our way into a 69 position, and brought each other off. I didn't want his dick out of my mouth, I wanted to hold it there, forever, but all good things must end, and it was soon time to take a shower, and go home. As I was getting dried off, Tom brought me a little present. He handed me a small, blue rubber object that I soon learned was a beginner sized butt plug. "Now, Missy, I want you to wear this at least one hour a day, for the next two weeks. If you can, leave it in for two or three hours, but no more than that. When you take it out, wash it in hot soapy water, dry it off, and hide it." Then he handed me a small bottle of Astro Glide, and told me that it was a lube to use with the plug, and to make sure no one saw it, either. Finally, he handed me a pair of pale blue nylon panties, with lace panels on either side of the front. I looked at the label, and saw they were Victoria's Secret brand. They looked expensive and very pretty. "Missy," He said, "These are for you to wear when you come over a week from next Saturday. I have to go out of town next weekend, so it will be two weeks until I see you again here. Now pay close attention. You WILL be here no later than nine o'clock, and no earlier than five minutes of nine. You will wear those panties and your new butt plug under your clothing. You will walk around to the back of the house, where you will find a set of instructions. Follow them exactly, and you will not be punished. Make a mistake, and you will be punished. Is that clear?" I told him it was very clear, and he kissed me long and hard, and then told me to get going. That Saturday was a long, long. long-g-g-g way off. I tried the new plug that very night, and realized that it was going to take some effort. I tried several different angles of insertion, and several different positions, until I found that if I lay down on my back, and lifted one leg high, I could get an angle that allowed me to get it passed my sphincter. Getting is past without pain was another thing, and I finally understood that it was going to hurt, gritted my teeth, and pushed it home. I almost yelled out with the sudden pain, but managed to keep quiet. It felt alien, and even though the fat part was inside of me, it still hurt, and gave me a burning sensation. I managed to leave it in for about fifteen minutes, then with another burst of pain, pulled it out, smuggled it into the bathroom, cleaned it up, and hid it in the toe of a pair of dress shoes I hardly ever wore, with the lube in the other shoe. The panties went into a lidded, tankard-style mug that sat high on a shelf, and was only moved to dust. Each night, I would get home from swim practice, frustrated because I was so close to my, well, what I now thought of as My Loving Master, but could say or do nothing. As soon as dinner was over, I would rush to my room, race through my homework, put on my pajamas, and insert the plug. By Wednesday evening, I could get it in without pain, and on Thursday, I put it in right after dinner, did my homework wearing it (although the hard wooden chair pushing on it felt funny), and then left it in while I sat downstairs watching TV with my parents. That was kinda weird, but neither of them could read minds, so I was safe. Finally, it was Saturday. And I mean it was the Saturday! I woke up early, and took a long, hot shower, using some of my younger sister's flower scented shampoo to wash and re-wash my hair, and one of my mother's razors to remove what little bit of hair was on my legs, my underarms and after some trepidation, the sparse hairs on my crotch and my balls. After I got out, and my hair was dry, I brushed it until it shone, and went back to my room to finish getting ready. I had already told my Mom another story about where I would be, so that was covered. My dad had left us, although he sent a fat check every Friday, so no problems there. Mom had taken my sister to the church to practice for the Christmas pageant, so no one was around to comment on my washed and brushed hair, or the quick spritz of my sister's perfume, which was the same flowery scent as the shampoo. I jumped in my 12 year old Honda, and left home for Heaven. I sat around the corner, studying my watch. When it was exactly 4 minutes of nine, I drove up the drive, and walked around to the back. There, I found a small box and a note. It read: Missy, as soon as you get this note, ring the doorbell, once. then, reach into the box, and take out the towel that you find, and place it on the step. Take off all of your boy clothes, put them in the box, and stand there, in just your pretty panties and plug. Shivering in the early December cold, I stood there, hoping no one would see me, and hoping the door would open soon. I needn't have worried, because I only stood there for less than a minute, before the door swung open, and Tom stood there in a black kimono and slippers, smiling down on me. He reached out, and lifted me up, swung me into the kitchen, and into his embrace. We stood there, kissing like long lost lovers for what seemed like an hour, but was really only a few minutes. I felt so warm, loved, and needed. I was ready to do whatever this lovely man wanted me to do. Finally breaking our embrace, Tom reached over to the counter, and handed me a pink satin robe, and a pair of soft pink slippers. I slipped then on, and sat down at the table with him, and enjoyed a cup of coffee and some chit-chat. I have to tell you, that I felt like nothing other than his loving wife at this point, a feeling that I never wanted to go away. He finally told me that he had a surprise for me, no, several surprises, actually. "First of all, my little sissy lover, since we last met, I have been on the internet, and have spent quite a bit of money on some clothing and some, toys for my little love." I blushed, and stammered thank you. He continued, "I think you will love most of what I have bought, and will come to love the rest. I also want you to know that before this weekend is through, you and your cute little ass will be in for huge surprise!" At that, I know I turned a bright red, and could only stare at the floor. This was going very fast, and even though I wanted to do this, it was still so very new to me. Also, I had brought up to believe that someone who was gay was somehow less of a person, someone to ridicule and belittle, yet here I was, falling in love with a gay man, dressing like a girl for him, and being gay myself. I was so conflicted, thinking one thing when I was dressed in jeans and a flannel shirt and with my friends, but thinking completely different thoughts when I was laying on my bed, a butt plug inserted in my bottom, and my hand wrapped around my young cock. Finally, I looked up at Tom, my face warm, and told him, "Tom, I am yours and yours completely. Whatever you want to do and whatever you want me to wear is okay with me. If you are happy and satisfied, then so am I. I just want to be with you, to feel your body next to mine, and to love you." With that, Tom just beamed a 500 watt smile across the table, and told me that from now on, I was not to call him Tom, or Coach, unless we were in school. From now on, I was to refer to him as either "Daddy", or "Sir." I would know when to use which name, he was sure. "Yes Daddy," I replied grinning. "Now, come with me to your new bedroom," Daddy told me, and we got up and walked hand-in-hand to the spare room. There was a deadbolt lock on the door, and as he opened it, I just stood there and gasped out loud. Instead of the bland spare room I had seen just weeks ago, there was now a perfect girly-girl's room! A white canopy bed with pink satin coverlet, and sheer pink and white netting over the top, white dresser and make-up table, and a pink rug in the center of the room would surely win the heart of any prissy little girl, and it certainly won mine! He ushered me in, and opened the closet door, and again I gasped! There was a frothy pink satin dress hanging there, along with another dress of some kind in black satin, and at least three or four blouses and skirts. On the floor were three pairs of heels, one shiny black with very high heels, a pair of pink pumps, and the white heels that I had worn the last time. He then opened the top drawer of the dresser to show me that it was full of panties, all in soft satin, nylon, and the prettiest, softest pastels. I just looked at this wonderful man, and all I could say was, "I love you, Daddy, I love you so much!" With that, we were back in each other's arms, his face in my hair, stroking me though my robe, and both of us crying for sheer joy. "I love you too, my little sissy, I love you too," was all he could say for several minutes. We finally broke apart, and he told me that he had another surprise for me, and that surprise would come after dinner that evening. Then, he told me to sit down on the bed, and he would dress me for a little "scene," as he called it. I went to the bed, and sat down, not really knowing what I was supposed to be doing. He walked over to me, and knelt down in front of me. He removed my slippers, and told me to point my left foot. I did so, and he rolled a delicate white stocking up my leg. I shivered as the soft material encased my bare leg. After both stockings were on, he slipped the white heels on my feet, and buckled the little straps over the instep. He then told me to stand up, walk to the foot of the bed, and stand facing it. I did, and he came up behind me and slipped off my robe, and gently pulled my pretty panties down my legs. Reluctantly, I stepped out of them, now standing in just hose and heels, waiting to see what Daddy had in mind. He then went back to the dresser, and pulled out something that was pale blue with a white lace overlay, and had strings hanging from it. It took me second, but I soon realized that this was a corset! I had seen them on women in the magazines, but had never seen one "for real," and never thought I would be wearing one! He stood behind me and wrapped it around my waist, pulling it snug. It was then back to the dresser, and this time it was nylon wrist cuffs with Velcro closures. He wrapped them around each wrist, and the clipped the cuffs to eye bolts I had missed, on each of the bed posts. With that, he grabbed the lacings, and pulled them as tight as he could, causing me to gasp that I couldn't breathe! I was told to breathe shallow, and to relax, as he pulled them even tighter, and then tied off the strings behind my back. He knelt behind me, and started kissing my bottom, and toying with the rubber ring of the plug with his teeth. After a bit of this, he pulled my stocking tight, and clipped them to the garter straps that hung down from the corset. Next, he told me to pick up one foot, and then the other, as he slid my pretty panties back up, and settled them on my butt. Out came the familiar ankle cuffs, but this time, he didn't attach the spreader bar. He took my wrists, and unhooked them from the bed, and then hooked them together behind my back. "Soon, Sweetheart, I will have you in an arm binder, and will pull your little arms back until your elbows touch! But not right away, and not this weekend, so you don't have to worry your pretty little head, yet," He chuckled, but not in a pleasant way, and again, I got those shivers of fear running up and down my back. Now he lead my down the hall, and back into his room. It was dark, and the only light came from about 20 candles burning around the room, giving it a romantic feel. He told me to crawl up onto the bed, and stay on my knees. With my hands behind my back, this was difficult, but I finally got onto the bed. Now, he pushed my legs apart, and put the spreader bar between my ankles. Coming around in front of me, he told me to open my mouth, and close my eyes. I did so, and the penis shaped gag filled my little mouth once more. I had no idea of what was coming, and was scared, thrilled, worried, and not a little turned on! He shoved a large, rolled up duvet in front of my knees, and pushed me down onto it, My hands were cuffed behind my back, my legs were spread, and I was gagged with my ass up in the air. I began to wonder what was coming, when, WHAP! He landed three solid blows with a leather strap on my unprepared bottom, causing me to scream into the gag, and try to jump and move. No luck, as his other hand was on the small of my back, making avoiding the smacks impossible. Three more slow and hard smacks had me crying and screaming, although all he could hear was grunting and muffled noises coming from me, and could feel my body heaving with the sobs`. He finally quit, and pulled my pretty blue panties down off my bottom, gripped the ring of the plug, and with a little pop, pulled it out. In the last week, I had worn this plug a lot, and felt sort of empty without it in my little sissy bottom. I needn't have worried. He gently probed my bottom hole with his finger, and then smeared more lube up there. "Now Missy, this is probably going to hurt, so if you want me to stop, just tell me, okay?" This line was delivered with another lewd chuckle. "Oh, I'm sorry, you can't tell me, can you? Well, we'll just have get over that, won't we, Sweetie?" With those words, I felt something hard at my bottom hole. He pushed and twisted, and it hurt worse than when I first tried my beginner plug. "I'm inserting a much bigger plug, now that you are used to that little beginner's toy. I really think you will like it!" Daddy now placed one hand on the small of my back to hold me down, and gave my new plug a very hard push. I screamed as loud as I could into the gag, tears running freely down my cheeks, my feet kicking those few inches my bondage would allow. I felt as though I couldn't breathe because of the gag and corset, and now my whole body was being split in two from this huge (I thought) and impossible plug! "Hush, my Sweet Angel, and breathe through your nose," he advised. "Just relax, and soon, the pain will go away. I used a light anesthetic cream with the lube, so the pain shouldn't be as bad as it sounds. At least I hope it doesn't hurt that badly!" He was right. After a few very, very painful and torturous minutes, the pain subsided to a dull ache. Daddy must have noticed that I had quit squirming, and was breathing easier, because he began to stroke my back, and rub my bottom through the panties. Without any conscious thought, my cock reacted, and was trying to rip a hole in my new panties! He increased the pace of his strokes, now reaching around to rub and tweak my nipples, poked out above my corset. I was stiff, my jaw ached, and my bottom was still on fire from the spanking and the plug, but I was as turned on as is humanly possible! Suddenly, without any touching at all, I felt the bliss of orgasm, and spurted cum into my panties. I lay there, the intruder still in my aching backside, dressed in a corset too tight to breathe in, gagged and bound, and I realized that this is what I wanted. I wanted nothing more than to be completely under another man's control. I wanted to be told what to wear, where to sit and stand, and when and how to have sex. I was in total submissive sissy heaven! As these thoughts were crossing my mind, Daddy was helping back up on my knees, and unlocking the spreader bar from my ankles. He helped me off the bed, and I stood there on shaking legs, wondering what was next. I didn't have to wait long, as he unbuckled and removed my gag, and the slid my cum filled panties down my legs. I stepped out of them, and he brought them to my mouth, and told me to lick my cum out. There I stood, still cuffed, and in a corset, heels, and hose, licking my own cum from my panties, and loving it. After a moment or two, he tossed the panties in the corner, and took off my cuffs. He kissed me gently, and told me to take a bath, and remove the plug in the tub. So a few minutes later, I was sitting in a perfumed bath, with Daddy washing me with a soft washcloth, and together we pulled the new plug out of my sore little behind. I was surprised at how narrow it actually was. I had had visions of something the size of a telephone pole up my backside, and this was just a bit bigger than my thumb! "Don't worry about it, Honey," Daddy told me, "you'll get used to the feeling, and then, your Daddy will fill you with the real thing!" I couldn't wait! He helped me out of the tub, and dried me with a soft pink towel, handed me the pink robe that I worn earlier, and we walked back to my new little girly room. I sat on the bed, and he sat on the little stool in front of the make-up table. "Remember when I told you about some clothing you may like, and some you may not?" I nodded. "Well, what I'm about to show you may be in both categories. He then went to the closet and produced a pink satin dress that was the most beautiful thing I have ever seen. It had a peter pan collar (although I didn't know then what it was called), short capped sleeves with a white satin bow on each sleeve, and was trimmed in white lace. He laid this creation on the bed, and produced a little nylon top that ended in a huge mass of ruffles. "This is a pettiskirt, and you wear it under your pretty dress," he explained. He then pulled out a pair of little nylon anklets with pink lace, and black, patent leather Mary Janes and laid them on the bed next to the rest of the outfit. "Where are my panties, Daddy?" I asked. "Hmm, I think we will get to those in a moment, okay?" He then helped be put on the socks and the shoes, buckling them tightly onto my feet. He told me to lie back on the bed, and to raise my legs. I did, not knowing what to expect. "Now Missy, whatever I do, I want complete silence, or I will gag you for the rest of the day and night, and you won't get any dinner." I resolved to be silent, no matter what. He took my new plug, and after applying lots of lube, pushed it into my backside. I thought it was a different plug, as it didn't hurt very much at all, but he told me it was the plug that I thought was going to kill me just a short time ago. Now he took something from under the bed, and slid it under my bottom. As he folded the material over my crotch, I realized that he was putting me in a diaper! I almost said something, but stopped just short. After pinning it very tightly on me, he slipped a pair of plastic panties up over my legs, and then I felt something strange. The waistband was pulled tight, and I heard a loud click, as he told me that my plastic panties were now locked on me, and would not come off. He followed this by sliding on a pair of pink satin panties with lots of lace on the bum that covered the pink plastic ones. I then stood up, and realized that I could not bring my legs together as the diaper was way too thick! Daddy then helped me pull the petticoats on, and I was amazed at how they stood out from my waist, and at how short they were. Finally, it was time for the dress. He floated it down over my head, and smoothed it out over the petticoats, then went behind me and zipped it up. After the zipper was up, I heard a little metallic click, and he told me that I was now locked into my pretty new dress, too, and only he had the keys. I told him that he also had the key to my heart, and got a soft kiss on the cheek. I looked in the full length mirror, and saw a little girl looking back at me. My satin and plastic covered diapers were on full display under the too short skirt, and I wasn't really sure about where this all was going. I was determined, though, to ride this road all the way to the end. I loved my Daddy, and I trusted him, and would do whatever he wanted of me. The final touch was a matching satin baby bonnet that he tied under my chin, and the satin mittens that again made my hands useless lumps. I took Daddy's hand, or rather, he took mine, and I waddled into the kitchen with him. He sat me down and asked me what I thought of the day so far. I looked at the clock on the wall, and was surprised to see that it was only just after one o'clock. So much had gone on, that I was sure it was late evening! We talked for a long time, Daddy drinking coffee, and me drinking apple juice from a plastic sippy cup. Daddy told me I was so-o-o cute like that. I could only blush. I told Daddy that I really didn't like to be hurt, but it felt so good when he made it feel better afterwards, that I didn't mind it too much. This also brought about the subject of the butt plug that was beginning to hurt as I sat on this hard chair, even though the padding of the diaper. "You have to get used to the feeling of something up your bottom, Dear One (I loved his sweet names for me!)," he said. "When I finally make love to you, I don't want to hurt you, but then again, I don't want you to be too loose!" He laughed as said this last, and I chuckled along with him. Finally, I got the courage to ask him why he dressed me as a baby. He told me that a baby was the ultimate in dependent. A baby did not talk, did not feed itself, could not use a toilet, and had to rely on his parents for everything, and that since I wanted to be submissive, and feminine, this was the pinnacle of sissiness. "And remember, little one," he went on, "you are mine to dress and to do with as I please. If I want you as a baby girl, or as a French Maid, or hogtied naked in the closet, that's what will happen, do you really understand?" Again, it felt as though I was being given an option to leave, and I sat there, thinking about that for a long few moments. I put down my cup, and ran my satin covered hands over my legs, then over the dress, feeling the soft material, and hearing the rustle of the petticoats, and the soft crinkle of the plastic panties. I stood up, and walked over to the living room, and looked at myself in the mirror over the fireplace. I was a boy, as my hard on seemed to prove, but I was standing in a man's living room, dressed in pink satin like a baby girl, willingly allowing myself to be a slave, or play toy, or I really didn't know what! After a final glance in the mirror, I waddled back into the kitchen, and sat down. I took a sip from my toddler's cup, noticing the Winnie the Pooh motif, set it down, and looked at my new Daddy, and then back down at the table. "I know I'm young, and a lot of people would think I'm too young to make such a decision, but I have made one, anyway." I started, "I have only really known you for a short while, and most of that time has been spent with sexual pleasure. I thought at first, I just wanted the sex, but I have really thought about it, and, Daddy, I love you. I don't love you as a father, but the way I think I would feel about a girl that I wanted to be with. I am yours, and want to be yours until you don't want me anymore." I looked up again to see Daddy in tears. "I love you so much, little Missy! I'm so glad to hear that you love me too! Now, I have just one question to ask you." I looked at him, sitting there in his black kimono, so masculine, and then thought of me looking so sissy, and wondered what new question he could ask me. I didn't have long to wait. He stood up, came around the table, and removed my satin mittens, and then knelt down beside me. He reached into the pocket of his robe, and brought out a small box. He opened it up, displaying...displaying...Oh My God, an engagement ring! "Missy," he whispered, "will you marry me? Will you be my bride? Will you be my beautiful sissy bride?" I just sat there, stunned. My emotions swirled around in my head colliding with questions about my family, my future, our future, and on and on. I looked this wonderful man in the eyes and said the only thing I could say, "Yes, I will marry you, and be your sissy wife." He slipped a diamond solitaire ring on my finger, and we hugged and I cried for the longest time. He led me back to his bedroom, where he took off my dress and diapers, and helped me to change into a beautiful peach silk baby doll nightie, and we crawled into his bed to talk. We lay there, listening to Bach on the stereo, talking for hours. I learned that he had been working on some application programs for a popular piece of consumer electronic gear, and had sold three to the company who made it, and for very good money indeed! They, in turn, offered him a job that was many times better paying than public school teaching. Along with the money from the sale of his house (It was sold, he was actually renting it until the end of the school year from the new owners!), and what he had in the bank, we could afford to move out to California, and when I was of age, we could married legally. For now, we would have a private ceremony, and as he said, "Be married in our hearts, if not in the law." Finally, we came to the point where we had to talk about my parents, and what and how to tell them. My parents were getting a divorce, and my dad had already moved out, so really, all that was left was to tell my mother, in such a way that she wouldn't freak out, call the cops, or worse. After a while, I told Daddy that I knew how to do it, and explained my plan to him. We also decided that I should remain a "virgin" until our 'wedding night'" Sundays at our house are quiet and peaceful. My sister is usually at a friend's house, and Mom has the day to sort of relax. Now, my mom is a very easy person to talk to if you have a problem, and I counted on this to get me through the next day or so. I had packed a bag of some things when I left Daddy Tom's place on Saturday evening, and left it in the trunk of my car until I could retrieve it privately. Mom was sitting in the living room, reading the paper, when I called down to her, "Mom, are you busy? "No Honey," she called back, "What do you need?" "I have something very important to discuss with you, and need to have a serious talk. Do you have time, now?" She sounded concerned when she called back up to me to come on down, she would be in the kitchen. What is it about kitchens that make them the default place to talk? Anyway, with shaking knees, I went downstairs and into the kitchen. I had prepared for this by bringing some clothing home with me, and was now wearing a semi-sheer white satin blouse, with ruffled bodice, sheer sleeves, and satin cuffs. Through the material, you could clearly see my white satin training bra. Below that was a gray wool skirt, white thigh-high stockings, and my slightly too tight white heels. I had my hair brushed out, and was wearing some pink lip gloss that I borrowed from Daddy's daughter's room. I was as scared as I have ever been. I walked into the kitchen, and Mom was sitting in her usual seat with her back to the hallway. She half turned when she heard the sound of my heels, and when she actually saw me, she stood straight up, and held both hands over her mouth nd sort of squeaked. I just stood there, not knowing what to do next. She finally took her hands away from her face, and with a quiet voice, asked me why I was wearing such pretty clothes. Not, "Why are you dressed like a girl?" Not, "What in the hell are you doing?" No hysterics, just a calm question. I ran over to her as well as I could in those heels, and wrapped my arms around her, telling her that I loved her. She told me that, no matter what, she loved me too, and please, sit down and tell her what the heck is going on. I told her all about Coach Norton, well, not all about him. I mean, she didn't need to know about the bondage, the butt plugs, and the rest. I told her that I was gay, and that I was in love with him, and all about the possible move to California, and then finally showed her the ? carat ring on my finger. This was the longest conversation I have ever had with my mother. We sat down in the kitchen around two in the afternoon, and only when my little sister called about seven thirty that evening to tell Mom she was coming home, did I go upstairs, and put my boy clothes back on. I don't think that Mom was "cool with the idea," although I think she understood that it was something I was going to do, with or without her approval. She finally gave in, and told me to invite Coach Norton over for dinner on Friday night, and she would make sure that my 12 year old sister was somewhere else for the night, so we could all talk. Friday, it seemed, would never come. My mother surprised me on Thursday night though, by asking me what I was going to wear for dinner. I was confused, but she continued, "I know that little outfit you wore on Sunday is the only bit of female clothing you have, and I have to tell you, it is too, shall we say, revealing for dinner. Now, go get in the car, and we'll head up to the mall in Raleigh, to find you a proper dress and shoes for tomorrow night." To say I was stunned would have been an understatement! At my Mom's urging, I ran upstairs, and put on my white panties and the bra, along with a pair of jeans, a shirt, and a sweater. Mom also asked me to bring down the heels that I had worn on Sunday. She looked them over, and asked me if they hurt to walk in. I told her the heels were fine, they were just a bit too tight. She looked at the size, and told me that I was getting new shoes, too. Three hours later, we walked out of Macys with a royal blue dress, black stockings, matching black panties and a 34 A bra, a black slip, (Mom told the lady that the dress was a surprise gift for my sister, and since we were twins, if it fit me, it would fit my sister!), and gorgeous pair of navy blue sandals with a 3 inch heel. Mom looked at me, and asked me if I was really, really serious about this. I just looked at her, confused again, and told her that, yes, I was very serious. With that, we took the dress, shoes, and lingerie out to the car, and she walked me right back into the mall. Mom made a bee line for a chain hair styling salon, and told the lady that I wanted to have my hair cut and styled in a very feminine style, but one that could be brushed out after the "costume party" on Friday. While I was having my hair washed, cut, and fussed with, Mom said she would be right back. I guess it was about 45 minutes later that she returned, with some more shopping bags. My hair was done, and I thought it was very cute, and so did my Mom. I now had bangs, and my blonde hair was now about collar length, with a flip to the bottom. The lady had put in some highlights, and it looked as pretty as any girl at school. Mom paid the lady, and added a tip, then drug me down the mall to the bathrooms. We went into the "family" room, where a mother could take a young boy, or a father a young girl. Mom told me to get undressed, down to my lingerie. She then handed me a pink T-shirt, a denim skirt, and a pair of pink tennis shoes. She told me that my jacket was one that either a boy or girl might wear. Once I was dressed, and also completely embarrassed by having my Mom see me in panties and a bra, we went back out into the mall, where we stopped in an accessories shop, and had my ears pierced, and a small pair of gold studs installed, and then it was on the nail salon, where I had a set of not too long nails applied, and painted a pale pink color. You could have knocked me over with a feather! Mom told me that if this all meant that much to me, then we had better do it properly! Mom came to the mall with a son, and left with what looked like a daughter, and I don't think I have ever been happier! So much had taken place so quickly, that I felt like I was in a blissful dream, and was afraid that at any moment, I would wake up. I stayed home from school on Friday, as the earrings, hair, and nails would have been very hard to explain. Mom strayed home from work, too, and spent the time teaching me how to walk in heels like a lady, how to sit, stand, and get in and out of a car, without showing my panties to the world. Finally, I got work cleaning the house, while Mom got dinner ready. She had started her homemade spaghetti sauce early that morning, and the house was full of the aroma. At six, my Mom shooed me up the stairs to get a bath. She told me to call her when I was dry and had my new panties on. I did, and she used body talc on me, helped me to put on and adjust my new bra, put on my stockings and finally zipped up my new dress. she sat me down and brushed my hair, and applied a little eye shadow, and some pale pink lipstick that matched my nails, and pronounced me ready. I stood up, and looked in the mirror, and saw nothing but a 12 or 13 year old girl dressed for a party! I twirled and turned in front of the mirror until my mother burst out laughing. "Well, if I had any doubts before, they're gone now!" she chuckled. "You preen in front of that mirror like a proper girl!" When the doorbell rang just a few minutes after seven, I answered it, and there stood Tom, or Daddy, or Coach, wearing a pair of gray wool slacks, black loafers, a black turtleneck sweater, and a gray tweed jacket. He looked beautiful! He took me by the arms, and held me, just running his eyes up and down, and finally kissed me gently on the lips. I won't bore you with the dinner and the conversation that went on until well after midnight. Suffice it to say it covered a lot of ground, from legal issues, to morals, to finance, to social concerns, and more. Around ten, the conversation turned to a more practical matter, our wedding. Mom and Tom (We had decided to dispense with "Daddy" in front of my mother) eventually agreed that we would rent a small wedding chapel in Raleigh, and that a friend of Tom's would serve as the presider. We decided to use the Methodist service, but leave out a lot of the religious aspects, and wherever the word lawful or legal was there, replace it with the word loving. At the door, Tom took me in his arms and kissed me like there was no tomorrow, right in front of my mother! What could I do, but wrap my arms around him, and kiss him right back! It was going to be a long winter, waiting for the school year to end, and my beautiful June wedding day. Christmas came, and both my Mom and Tom bought me lots of beautiful clothes. By now, my younger sister, Stephanie knew, and she promised to keep it a secret. Tom and I did not see each other as much as we wanted to, as my mother wanted us to keep a low profile. I did wear a girl's nightie to sleep in every night, and Tom brought over my pink robe and slippers, but that was about the extent of my girly dressing. Mom spent the time teaching me to wash, iron, cook, and clean for my new husband, and often had me working in high heels to get used to them, as Tom had told her I was not going to be allowed to wear other types of shoes. When I went to Daddy's house, I always wore the most beautiful lingerie, and nightgowns, and when we went to dinner (way out of town) I always wore at least panties and stockings under my slacks. The only other dressing that was done in our home was trying on all the pretty things I got for Christmas from Daddy, and even some lingerie from Mom, and a beautiful ivory colored, baby doll nightie and perfume from my little sister! Mom kept all of "Michelle's" things in the spare room closet, ironed and in plastic bags, ready for my honeymoon and new life. The winter dragged on and on, and finally, it was spring and school was over, and the day was right around the corner. Mom and I had bought my wedding gown on-line, and one of her good friends did the fitting as a quiet favor. It was a dazzling white silk dress, off the shoulders with ? length sleeves, and a full skirt with layers of crinolines, all dripping with lace and a few well placed seed pearls. I decided that I would wear a traditional veil, and carry a bouquet of pink roses arranged with baby's breath. The day dawned clear and warm, with none of the humidity that eastern North Carolina is known for. We made it to the chapel in plenty of time to get dressed, in spite of traffic and a fender bender blocking the road. My sister was my maid of honor, and wore the most gorgeous pale green taffeta dress, that really set off her hair and eyes. Mom wore a very nice dress of ivory silk with a muted pattern of climbing roses, and she never looked more beautiful. Under my dress, I wore my white satin corset with the baby blue lace overlay, as something old and something blue, white satin panties with ruffles and a ribbon at the back that laced up the middle, and kind of hugged my butt crack. Thigh high stockings with a lace pattern adorned my legs, and under my dress I wore some things that Daddy insisted on. Six inch stiletto heeled pumps meant that I could not walk, only mince, and a tight, knee length hobble skirt that ensured that I "couldn't run away!" To complete the "wedding party," one of Tom's good friends stood up as his best man, and wore a bow tie that matched my sister's dress. It was all so perfect, that I wanted to start bawling before the ceremony even started! I don't remember the details of the wedding at all. I do remember Tom slipping the ring on my finger, and then lifting my veil for a kiss. And, I don't think any couple, no matter what the gender, ever kissed with that much love and passion. It was a time of pure magic. We had our pictures taken by another friend with a good digital camera outfit, suffered through a very short reception, and we were finally alone. I do remember one detail from the reception that really got a few laughs. My sister, Stephanie, after everyone else had made the required toasts, stood up, told us that she hoped we would be very happy, and then announced, "When I get married, I want to wear the same dress my brother is wearing, and I hope I look as beautiful in it as he does!" Tom had hired a white limousine, and the driver was so sweet as he helped me get my skirts into the car without getting them dirty! On the short drive to the hotel, we could not stop kissing, and I'm sure the driver was watching. Boy would he have been surprised to learn that both the bride and the groom were sporting hard-ons! We swept up to the reception desk. Tom looked so suave and masculine in his black tuxedo, and on his arm, a blushing bride in full regalia, just basking in his manliness. I know my legs got looked at as I held up my dress to walk a bit easier. Of course, the very tall silver heels attracted attention, and the fact that I had to take little, tiny steps allowed everyone to get a good look! Again, what would they all have thought if they knew what was under the bride's satin panties? Into the elevator, into the hall, and there it was, the door to the Bridal Suite! This was too perfect, too storybook to be real! The bellhop unlocked the door, Tom gave him a tip, and then without any warning, picked me up as easily as if I were a baby, and then we were behind closed doors, as man and wife, or at least as man and sissy wife. Daddy told me to go into the bathroom, and remove only the hobble skirt, go to the "potty" if I needed to, and come back out. I complied, and came back out to a bottle of champagne on ice, and my darling husband standing there, his jacket and vest off, bow tie undone and hanging loose in his collar, and looking so handsome! I felt like the luckiest girl, or I mean luckiest boy, I mean, well, I was so lucky! He swept me into a passionate embrace, holding me tight to him as he kissed me, hard. He then began kissing my cheeks, my forehead, lightly brushing my eyelids with his kisses, and I in turn, just melted on the spot. He broke away to pour us each a glass of champagne, and we toasted each other. He handed me his empty flute, picked up the cooler, and motioned me to precede him into the bedroom. There, he once again wrapped me in his arms, kissing me and caressing me. Finally, his hand went to my back and slowly lowered the zipper of my gown. It swished to floor, and then the crinolines followed, and I stood before my new husband in corset, panties, hose and heels. Without a word, I began to undue to studs on his shirt and cuffs, removed the shirt, and then dropped to my knees amidst the folds of my wedding gown, and slowly unbuckled his belt, undid the catch, lowered the zipper, and then all that was between me and his wonderful cock was a pair of black silk boxers. I kissed and nibbled his thick hard member though the material, and finally released his monster into my waiting, pink painted lips. I never wanted anything as badly in my life, as I wanted that cock in my mouth! I kissed and licked him, sucking the head into my mouth, and swirling my tongue around it, feeling the heat, and the soft, velvet hardness of it, and then took it deep into my throat, relishing the feel of it filling my mouth. I wanted him to cum in my mouth, to taste his salty man juice, but after a few moments, he pulled out, and lifted me to my feet. "Missy, my dear bride, it's time I ended your virginity and made you my wife! I wanted that too, but I was scared. I knew that the plug I had been practicing with, and often wearing for hours at a time, was less than half as thick as Daddy's cock, and not nearly as long. I was sure I would be split in two by him! I had a realistic rubber dildo that I used to practice sucking, and to "deep throat" without gagging, but I was forbidden to use it on my bottom, or anything bigger than the plug that Daddy gave me. It was "crunch time". "Missy," he spoke again, breaking my thoughts, "I know you want your first time to be special, but so do I. You know that in all things, you are my slave, my servant, and my submissive. You're first time will be in bondage, because that's the way it has to be." I nodded, having already figured out that little detail. He led me to the bed, and told me to turn around, and open my mouth. He stood behind me, and inserted the penis gag into my mouth, buckling it tightly behind my head, then lowering the veil I still wore down over my face. I was placed in my satin mittens, and they were buckled onto my wrists. He told me to put my arms behind my back, and then I heard him rummaging around in a suitcase. He then placed a leather sleeve over both wrists, and I felt him lace the sleeve loosely over both arms. I grunted in real pain as he pulled the laces tight, forcing my arms together behind my back, my elbows almost touching each other. my ruffled white leather collar was then locked around my neck. My Daddy then added a new wrinkle. He produced beautiful little silver clips, and proceeded to place one on each nipple, causing me to gasp in pain. I was told to get onto the bed, and kneel, which he helped me to do. The cuffs were placed back on my ankles, and the spreader bar once again held my legs spread. He placed two pillows under me, covering them with a towel, and told me to lay down over them. The final touch was a strap that he hooked to my collar, and then ran back behind my knees, and back up to the collar, pulling it tight, forcing me into an even tighter crouch, pushing my poor bottom skywards. I could not move an inch in any direction, could not move my hands, or even use my fingers, and calling for help was right out of the question. My nipples were on fire from the clamps, and my shoulders and arms ached already. Slowly, he caressed my pantied bottom, and then pulled on the little satin ribbon that laced the two halves of the panties together, exposing my virgin asshole, without taking off my girly panties. With exquisite slowness, he fingered, and then licked my rosebud, sticking his tongue between my cheeks, almost causing me to cum right then and there. After a long, sweet time, I felt him stick his finger up my bottom, and could feel the cool lube being applied. He then did a curious thing, and stepped away from the bed. I heard him fumbling with something, and then was blinded by the flash of a digital camera, recording my bondage and vulnerability. Daddy took at least 10 pictures before he put the camera down, and once again, stood behind me. With soothing words, he placed the head of his cock against my virginity, and without any warning, rammed it into my bottom. I screamed and screamed into the gag, trying desperately to wiggle free of this horrid thing. I knew there had to be gallons of blood pouring out of me, as he ripped me in two! He just stood behind me, not moving at all, his hands rubbing my shoulders and my ass, reaching around to touch my still hard cock, and then to tweak my burning nipples. The pain began to subside, and with it, my attempts at freedom, and he began to rhythmically fuck my bottom, sliding his huge cock almost out, and then ramming it home again. I could feel his balls slap me as he came forward. Faster and harder he fucked me, and I found I was attempting to meet his thrusts by pushing back with my ass, although I had only millimeters of movement allowed me by the bondage. The pain in my nipples and arms, blended with the wonderful feeling of that cock sawing into me, and I suddenly realized the connection between pleasure and pain, and relaxed into the experience. I felt Daddy tense up, his cock swelling even more, and then he filled my bottom with his wonderful seed. At almost the same time, I filled my panties with my own cum, and I knew that I was now Daddy's wife, his slave, his personal slut, and wanted nothing else in this world than to continue. I could feel his cock soften, and finally, he pulled out of my bottom, leaving me feeling very empty. He kissed me on each cheek of my ass, and then, leaving me hog ties and gagged, went into the bathroom to clean up a bit. A minute or two later he came back to the bed, and began to let me out of my restraints. First he released the strap to my collar, and helped me back to a kneeling position on the bed. Next, he removed the arm binder, and massaged my shoulders and arms until the circulation started back. The ankle cuffs came next, and he helped me to stand on my feet, and held me until my rubbery legs came back to life. He told me to stand very still, and to relax, and released my nipple clamps, which hurt worse than putting them on, causing me to scream into my gag yet again. With infinite kindness, he gently kissed and licked each nipple until the fiery pain subsided. At last he removed my veil and took that huge rubber penis out of my mouth, and I wrapped my mittened hands around his neck, kissed him, and told him how much I loved him. He led me to the bathroom, and for the first time, I noticed a huge whirlpool / Jacuzzi tub, that was already filling with hot water. While it finished filling, Daddy lovingly undressed me, removed my mittens, and helped me into the tub. He got in, sitting behind me, and turned on the bubbles, massaging and rubbing my aching body, all the time telling me how much he loved me. The only jarring note for me was that in the tub, devoid of my feminine trappings of satin and lace, I was just a boy. I wasn't special any more, at least to my eyes. Sure my finger and toenails were painted pink, and my hair was done in a very feminine flip, but to mind, something was missing. My symbols of being a sissy were strewn on the floor between the bedroom and the bathroom. He told me not to worry, that he still thought of me as his sissy slut wife, and that made me feel much better. Once we finally got out of the cooling tub, he helped me to dry off, and then presented me with a white satin teddy, with ruffles around the leg openings, and panels of lace and pretty white bows. There was a matching sheer bed jacket, and at his urging, I put on a pair of white thigh high stockings that had rubber around the inside of the tops to hold them up, and put my silver wedding shoes back on. I fixed my hair, redid my lipstick and eye shadow, and sat down while Daddy called room service for dinner. While we were waiting, we cuddled and kissed, and finished the champagne. A very short time later, there was a knock on the door, and I jumped up to hide in the bedroom, but Daddy put a hand on my shoulder, and told me to sit right there. When the waiter came in, he had no trouble identifying me as a boy dressed in lingerie, and living with a man in the bridal suite. I was so embarrassed, I could feel my cheeks heating up, and could only stare at the floor. Right in front of the waiter, while he was setting up the dinner, Daddy told me to go into the bedroom, and hang up my wedding gown, which I think caused me to blush all the way to my knees! I could feel the waiters eyes following me out of the room, and then heard Daddy chuckle and say, "She does have a cute little ass and nice legs for a sissy boy, doesn't she?" I dashed as fast as I could for the safety of the bedroom and closed the door, and just started to cry. I felt so violated and exploited. Why did he do that to me? I already knew he owned me, I was his! Why this display of macho power when he just had me, trussed up, powerless, and willing? I just stood up in a wedding gown, and publicly professed my love for this man, and now this? I was hurt, and angry, and sad. Daddy knocked on the door, and quietly came in. "That upset you, didn't it my precious?" He asked quietly. I just nodded. "Remember, Sweetheart, you are now my property, and even though I love you, and want you with me always, you have to understand your place. That was just a small lesson for the rest of our lives. Remember this lesson, and you'll do just fine. Forget, and you will be sorry. That overpaid busboy is a nobody. Sure he'll gossip, and within the hour, everyone who works here will know that you are a gay sissy, and that I married a sissy. But who cares? We will be here for a few days, and then it's on to our honeymoon, and on to our new lives together, twenty five hundred miles from here. Now come and eat, my love." I dried my eyes, went back to the bathroom to fix my makeup again, and joined my husband for a dinner of lobster tails, shrimp, oysters, and more champagne. Over the next few days, we sucked and fucked like minks. Sometimes I was bound, others, I was just dressed in a nightie, and free to explore my Daddy's body, and he to explore mine. It was three days of bliss, marred only by a few other public displays of his new sissy bride. The first was the next morning, when he had me dress as a fantasy French maid, complete with locked-on high heels, and my gag. My outfit consisted of a black satin dress with a white satin pinafore style apron tied in a big bow in back. The dress itself was way too short, held out from my body by multiple layers of crinolines which showed off my black satin panties with white lace trim. You could also see my garters and black seamed stockings. I also wore the mandatory white ruffle of lace around my throat, and white lace cap. The finishing touch were the black pumps with 6 inch heels, and short silver hobble chain that went from shoe to shoe to make sure I took little "lady-like" steps. When the maid came in for room service, Daddy told her that he had a sissy boy maid who was going to help her, and that she was to tell me what to do. The maid was a chunky Hispanic lady, who thought the whole thing was a hoot (She had heard about the sissy in 614, and now she knew it was true!). She had me clean the toilet and dust, all the while bending from the waist, and not the knees, so my pantied ass was on display. She also made me go out at least three times into the hall to get something off the maid's cart that she "forgot." Then, as she made me vacuum the suite, she kept swatting me on the ass, and telling me that I had missed a spot. I was totally, thoroughly, and completely humiliated. She even asked Daddy if I still had my "boy parts, and he made me stand there, and lower my panties so she could see my shaved cock and balls. What surprised me was that as humiliated as I was, I was as hard as a rock! The maid left, laughing at the sissy in the maid's dress, and Daddy was so turned on that he pushed me over the back of the chair and with just a little spit for lube, took me right there in the living room. When he was done, he spun me around, knelt down in front of me, and gave me the best blowjob I have ever had. There was something to this whole humiliation thing! My final piece of humiliation for the weekend came the morning we were packing to leave. He reached into a dark plastic clothing bag that was hanging in the closet, and pulled out my pink satin sissy baby dress. It was back into that thick cloth diaper and pink plastic panties, covered with those beautiful satin sissy panties. I was dressed, and locked into the dress, and he handed me a little baby doll to hold. He placed a large NUK pacifier in my mouth, tied it behind my head, put on my bondage mittens, my pink satin bonnet, sissy anklets and black Mary Janes. The final indignation was when he produced a harness and leash made of pink leather, just like you might use for a toddler in a mall, put it on me, and then called downstairs for the luggage to be picked up. It was at that moment that my mother and my little sister came to the suite to pick up my dress to be cleaned and stored. They obviously thought we had already left. I found out later from Daddy that he planned on my mother seeing me this way, to make sure that everyone "knew the score." She just looked at me, looked at Daddy, kissed me on the cheek, and wished me luck. I'm sure she was shocked, and curious, but kept her questions to herself, at least for the time being. Stephanie, on the other hand, walked all around me, touching the dress, lifting the hem to see my panties and diapers, giggling loudly. She even stuck her hand down the front of my plastic panties to see if "baby was wet!" I felt very low right then. The bellboys got there and picked up the luggage laughing at me in my dress, and Daddy walked out with them. I started to follow, but he told me to wait. I stood there in the open doorway for a moment, and then a woman got out of the elevator, and walked up to Daddy. He handed her some money, and she walked up to me and without a word, took the leash, and led me to the elevator. She was tall, with long brunette hair, and very pretty. She was dressed in a white blouse, and a gray jacket and skirt that looked like a business suit, but with a short skirt and very high heels. I wondered if she was a business woman, or a friend of Daddy's, or what. Turns out, she was a business woman, if you count the escort business! She led me off the elevator, and into the lobby. It was Monday, and the place was busy with businessmen and women, and the whole place just stopped, stared, and then began laughing as one. As if the over-the-top sissy dress, oversized pacifier, bonnet, mittens, and sissy panties on display weren't enough to incite laughter, the back of the harness had the words SISSY BABY BOY written in rhinestones! I froze in the middle of the lobby, and without a word, the lady sat down on the edge of a stone planter, and pulled me across her shapely legs, and proceeded to spank my diapered butt. It didn't hurt, but it was so embarrassing! With each smack, she yelled, "I (whap!) told (whap!) you (whap!) that (whap!) I (whap!) would (whap!) not (whap!) put up (whap!) with (whap!) your (whap!) silly (whap!) sissy (whap!) nonsense!" She stood me up and I was crying from the sheer humiliation of it all, but she continued in loud voice, "I just can't believe a boy like you wants to dress up like a baby girl anyway. Now look at yourself, crying like a baby, and I'll bet you even wet your diaper like a baby. You disgust me!" With that, she jerked the leash, and walked me to the waiting limo, my head hanging down, and my cheeks hot with shame. But, in spite of myself, I could feel my cock trying to tear its way out of its cotton, plastic, and satin prison. Daddy was waiting in the limo, and it took us to the private side of the airport, and pulled up next to a sleek white private jet that Daddy had chartered, and my further exposure to the world was mercifully short. Once on the plane, I was allowed to remove my dress, but sat there in my diaper, bonnet, and mittens. After a while, Daddy unbuckled his belt, and we sat together on a leather couch, and cuddled and kissed, Daddy finally forcing me to my knees and, while I might say I gave him a blow job, the truth is that he rather forcefully fucked my mouth. He then told me to get up, and go the bathroom. There, he told me to sit on the toilet seat, and open my mouth. He then admonished me to not spill a drop, stuck his cock back in my mouth and began to pee! I was shocked, but he would pee, cut off the flow, and I would swallow, then he would do it again, until he was dry. It tasted horrible, and I never wanted to do it again, but he told me I was being punished for not walking across the lobby like a good little girl, and for making a scene. I was mad, and wanted to tell him that the "scene" was engineered, and not of my own doing, but I realized that it was all part of his plan, and that I would have been "punished" anyway. Daddy wanted to, Daddy liked it, so Missy took it. He finally took off my baby things, and I was allowed to brush my teeth. Then I got dressed in a pretty peach silk dress, with white high heeled sandals, and what Daddy called my "outside bra." Instead of a training bra that did nothing but emphasize my flat chest, this bra had inserts that gave me a B cup bosom, and did a lot to hide the fact that I was a boy, not a girl. Daddy told me that the vitamins that my mother had been giving me were actually a low dose hormone, and that with some special cream that I was to start using, I would develop little titties of my own. Not too big, Daddy warned, because I was still his sissy, and he wanted a sissy slut for his wife. The rest of the way to San Francisco, we discussed what we would do and see, where we move to after the honeymoon, and all the things a newlywed couple would discuss. I knew that I had some lessons to learn, and would have to come to terms with my new status, but I also knew I was loved, and needed, and wanted my Daddy's cock up my boy pussy and in my mouth for the rest of my life.

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I opened the door. She was there, wearing her chocolate-colored long raincoat, pearl choker and earrings with brunette curly wig, made up and right in front of me. I smiled like the cat who had the cream (and I was hoping to have that soon!) and stood back as walked in. I was in my sheer pink nightgown with red bra and panties, stockers and garters, tottering in shiny black heels. "My own sissy!" I said to Regina and we kissed, our lips slithering against each other, smearing our...

2 years ago
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Meinen Mann zur Sissy erzogen

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

1 year ago
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Sissy spit roast sleep over

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

2 years ago
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The SissyMaster

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

2 years ago
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The Sissy App

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

3 years ago
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A Sissy called Jezebel Part VIII

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

2 years ago
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Adult Sissy Little Girl World

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

3 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

1 year ago
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Training Sissy Michelle

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

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

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

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

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

2 years ago
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Good Sissy Girl

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

3 years ago
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Sissy School Part 3

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

1 year ago
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Sissy tasks

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

3 years ago
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She Found a Sissy

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

4 years ago
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100 Sissy Points

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

3 years ago
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Welcome Your Now a Sissy

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

3 years ago
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Femocracy A Sissy Maids Tale

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

1 year ago
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A sissy called Jezebel Part II

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

3 years ago
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407am Sissy

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

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

2 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

1 year ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

1 year ago
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99 Sissy Stories

99 SISSY STORIES by Throne I've read about things like this happening but never thought I would experience it. My wife Grace discovered my stash of TV magazines and all the pictures I'd clipped out of her discarded catalogs that showed fashions I liked. She had me trapped with no way that I could deny my guilt or convince her that I wasn't attracted to wearing those things. She sat me down on a footstool in our den and stood in front of me. She has a sweet girlish face and an...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

1 year ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

3 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

1 year ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

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