Born A Sissy free porn video

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Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood her need to be young and flamboyant. I had no problem watching Timmy any time and having him accompany me to church on Sundays. I was often times alone anyway and cherished having the company of Timmy. I was very lonely back then. My husband of 26 years had left me for another woman shortly after Timmy was born. On top of that Timmy's father skipped town as soon as he learned of my daughter's pregnancy. I was devastated and was left with a lot of anger in my heart toward men. I had decided that I would dedicate myself and any love I had left to ensuring that Timmy was brought up right. I wanted him to be a kind, caring, gentle, and loving person. I wanted him to grow up just the opposite of his father and grandfather. In order to do this I had to introduce Timmy to feminine things and continually work to keep him emotionally in touch with his feminine side. This would require me to nurture him and teach him from a very young age. At about 9 he was making the turn toward becoming a rough and tough boy. He did all the things little boys did. He played with big metal Toy trucks, climbed trees, played in the mud, and wrestled and fought with other little boys. To a degree this behavior is necessary but I wanted to keep a watchful eye on Timmy's boyish development. I wanted to keep him grounded and not let him venture too far away from his feminine side. One of the first areas for me to easily expose Timmy too was talking. I had always had a soft, loving, girly voice that was ultra feminine. I often whispered softly to Timmy how pretty he was. I would softly tell him how much I loved and cared for him. I would call him things like sweetie, sweetheart, precious, honey, and cutie. I believe these tender words had a deep impact on Timmy's behavior and his personality. Timmy was easy to teach and displayed many natural feminine qualities and mannerisms. He was very cute and had high cheek bones, full bright red lips, and long beautiful eyelashes that looked more like a girl then a boy. His hair was the most beautiful strawberry blonde. He liked to wear it long and didn't mind having to constantly move his bangs out of his eyes. Early on I began to notice that some of his mannerisms were more girl like then boy. He sat with his legs together tightly and often crossed his legs or ankles while sitting. He flung his hands and arms far behind him when he ran. He often put his hands high on his hips when he talked. When he drank from a glass he would often have a pinky finger sticking out. He would tuck his hair quickly behind his ears like a girl would. When watching TV he would hold his chin in a girly way. And at times he would walk around with a limp wrist. He was very much swishy and displayed behaviors that could be referred to as very sissy. I think there were two parts to Timmy's early girl like behaviors. The first one being that genetics created them during pregnancy and birth. The second one would be that Timmy was always exposed to women. This included me, my daughter, my sister, and Timmy's two young female cousins. Everything that Timmy witnessed was feminine and he naturally learned to mimic and emulate female behaviors. I couldn't have been happier. Initially I worried a little bit about Timmy growing up gay. Over time I became more comfortable with that possibility. Being gay was much more accepted and many gay people I had come to know were very nice people. So if Timmy were to be gay I would be just fine with it and love him no matter what. So I continued to expose Timmy to female things and at the age of six Timmy began the journey into all things feminine. He was encouraged to be as girly as he wanted to be. My goal was to treat Timmy like a sissy. I wanted him to be raised as a girl in order for him to be a proper as a man. And I think Timmy was already a sissy when he was born. He loved being treated like a girl and I don't think he could have imagined his life any differently. Hi I'm Timmy and I'm now 12 getting close to 13. I'll never forget when I was little and all that I experienced and learned from my grandmother. She was the most loving and caring person in my life. I love my mother just as much but she was not the stable influential parental figure that Grandmother was. She was simply too young and had many things going on in her life. I knew at about age 5 that I was different then other little boys. I day dreamed a lot and preferred to engage in softer lighter activities. I often wondered what it would be like to be a girl. My two cousins Poly and Haley were only a couple years older than me. Poly was 7 and Haley 8. We would play together a lot. There were your typical little girls who played house while pretending to grocery shop and be mommies. I would always end up in some girly role that I was not always happy with. I was still a boy after all. But they were older than me and if I resisted I would simply be over-powered by them. With Poly and Haley being my main two playmates I became an expert on combing dolls hair and dressing them in all kinds of outfits. Poly and Haley often times played dress up and had made attempts early on to get me dressed in various outfits. During these times I would put my foot down and strongly resist. I would kick and scream until either Grandmother or Aunt Rachel came to my rescue. But as much as I resisted the more I wondered about what it was like to dress like a girl. I caught myself many times catching a glimpse of Poly and Haley's underwear as we all sat together Indian-style combing our dolls hair. They were pretty pastel colors, and most of the time pink. Not like my plain white cotton briefs. And then there were the tights they often wore. They encased their feet and legs and went all the way up to their waste. I thought about what it must feel like to wear full tights instead of plain white cotton ankle socks. Their tights were always either pink or white and they had that silky sheerness to them that made them very girly. Many times I would accidentally rub up against their legs while playing and the feeling of the tights was unlike any fabric in my boy clothes. And when they had their shoes off I would admire their cute pink painted toe nails showing thru their pretty tights. Yes I think I was fascinated by tights from day one. Poly and Haley also wore the prettiest dresses that were layered in lace and ruffles. They wore petticoats and leotards with them a lot and the fabric was so silky and soft. I especially loved the sheer sleeves and sheer bottoms of the dresses. They always made certain to wear matching hair bows or ribbons in their hair as well. They applied make-up to each other and painted their fingernails also. They were very much the typical little girls that wanted to be beautiful and older. The more and more I was around Poly and Haley the more I dreamed about being a girl. Aside from that I was constantly exposed to everything feminine around my Grandmother and Aunt Rachel. Sundays mornings before church were especially girly days. Everybody would spend hours getting all made up for church. For me I was ready in about 10 minutes and spent my time watching cartoons while they all paraded back and forth from the kitchen, to the bathroom, to the bedroom. Grandmother always juggled getting ready with making breakfast for everyone. She would walk thru the living room in front of the TV and on to the kitchen wearing nothing but pantyhose and a bra. Then later she would walk thru with a different color or shade of pantyhose and a silk or lace slip. Then she would walk by with at least two or three different dresses on. She was very indecisive but always ended up beautifully dressed. She was definitely all girl and pantyhose were a staple in every article of clothing she wore. Even when she had on pants she wore her pantyhose and open toed sandals. And she didn't wear knee highs either like many other women. She wore complete full control top pantyhose. I asked her why one time and she said that it makes her feel like a lady and that one day I would understand. Her dresses were all beautiful with lots of silk sheerness and lace. She had some gorgeous flowered dresses that were so pretty. So all morning between my cartoons I watched my grandmother, Aunt Rachel, Poly, and Haley getting ready for church. Aunt Rachel was quite the looker as well and she wore stockings with garters. Poly and Haley of course had their little girl tights on with their pretty swishy dresses on. Poly had this one pair of tights that were incredible. They were sparkly white with little pink hearts embroider on them. They screamed little girl all over them. And the smell of hair spray and perfume throughout the house was strong. I loved it so much. I couldn't wait for Sundays every week. It was entertaining and the energy was always so happy and upbeat. But every Sunday I found myself more curious and drawn to feminine attire. My very first experiment with women's clothing came on a Sunday when I was about six years old. Everybody was again getting ready for church. I was in my pajamas watching one of my favorite cartoons as usual and drinking my third cup of chocolate milk. Probably one cup too many because I had to go pee pretty bad. Aunt Rachel was in the bathroom just finishing a shower. I knocked on the door, "Aunt Rachel I have to go to the bathroom." "Oh Timmy, I just got out of the shower and I'm not even fully toweled off yet" Can't you hold it for a bit?" "I don't think so Aunt Rachel, I gotta go really bad." Just then the door opened to reveal aunt Rachel wrapped in a pink towel and another towel on her head. She still had beads of water on her. She huffed as she walked by me, "Ok make it snappy little boy...I need to get back in there." I was so happy she let me in. I was about to explode from all the chocolate milk. As I stood there peeing I noticed a pair of white pantyhose draped over the towel rack. I couldn't resist and ran my hand across them. They felt so soft and silky. Also hanging on the door behind me was a beautiful white satin mid calf slip. These were the items that Rachel was about to put on. She was just as girly as grandmother and rarely did she not wear pantyhose or slips. I started to think about what it would be like to put the pantyhose on and then the slip. I came very close to taking them down and trying them on, but I was afraid that I might wrinkle them and that Aunt Rachel would notice. To my right there was a tall clothes hamper. I decided that I'd take a look in there to see what I could fine. It just happened to be full of clothes. And right there on top was a pair of dark nude pantyhose. I picked them up and rubbed them across my stomach. They felt so nice. They still had a smell of perfume on them that I recognized as Grandmother's. She always sprayed a shot of perfume on each leg after she was dressed. While I was standing there with my pajama pants down to my ankles I couldn't resist the temptation. This was a great opportunity to try on the pantyhose. I quickly removed my pajama pants and sat down on the toilet. My hands were trembling and my heart raced. I could feel the blood rushing thru my cheeks. I stuck my first little foot in and pulled the silky pantyhose up my leg. Then I quickly inserted my other leg and stood up to work both legs up past my thighs. I was shaking like crazy and my stomach had butterflies. I pulled the hose up past my waste and snapped the elastic band. I could not believe what I had just done. I was shaking so bad and breathing heavy. The feeling was electrifying. I felt a feeling throughout my body that I had never felt before. It was like I was reborn at that moment. I felt naughty at the same time. And then it happened. I felt a tingling in my groin. Even though I was only nine I had gotten a rock hard erection. I didn't understand it but it felt so good and so right. I stood there looking at myself and almost faint. Wow I thought. The pantyhose feel so good and I love the way they cling and hug every part of skin they touch. Just then three loud knocks came on the door, "Timmy what's taking you so long, Hurry up! I need to get back in there young man!" "Ok Aunt Rachel, almost done." For one final few seconds I admired myself and rubbed both of my legs up and down. I was in sheer heaven. I then slowly and carefully removed the pantyhose and placed them back in the hamper. My excitement was still evident and I tried to think of other things to get it to return to normal. Luckily after a few seconds I was ok again. I quickly pulled my pajama pants back on and exited the bathroom. Aunt Rachel shoved me lightly out of the way. "Gees Timmy, you're as bad as a lady." My mind was still racing and I was going over again what just happened. I felt like I had done something very wrong and even at my young age thought to myself that what I had just done altered the course of my life. Just then Poly walked by wearing a pair of pink tights with a lighter pink slip on. My eyes were glued on her outfit and I scanned her up and down. But only from her neck to her feet. She noticed that I was looking at her clothes hard and didn't even make eye contact, "What, you don't like my clothes Timmy?" I swallowed and tried to focus, "umm, yeah, I like them. Your tights match your slip Poly." Yes they do, I so love wearing tights and slips. Mommy only lets me wear slips on Sundays for church." As Poly walked away my eyes followed her every move. After just having the pantyhose on I imagined what it would be like to have on tights and a pretty slip. My heart started to race just thinking about it and my excitement started to return down there. I quickly turned my attention to the television so I could prevent any further excitement. Just as soon as I was calmed down here comes Haley all dressed up in a beautiful pastel blue dress. It was full of ruffles and lace. She had on sheer white tights and a matching white bow in her long pinned back blonde hair. She was all girl and she knew it. She sat down by me on the couch and asked, "Whatcha watching Timmy?" "Oh just some cartoons." I couldn't help it but I kept glancing down at Haley's dress and tights out of the corner of my eye. "Timmy why do you keep looking at me? Do you not like my dress or something?" "No I like it a lot Haley." "Mmm alot huh? If you like it so much why don't you let Poly and I dress you up in it the next time we play house?" I started thinking about what to say and really wanted to jump at her invitation and tell her yes. But I was scared and said, "No way Haley! I'm not going to wear your stupid dress." "Ok Timmy, sorry, I was just asking." For some reason I think Haley saw my hesitation but I wasn't sure. She was pretty smart most of the time and picked up on things that Poly couldn't. Just then Haley left the room and went into Grandmas room. I thought nothing of it and figured she was just making the rounds hanging with the girls. Haley entered grandmother's room and saw her sitting at her vanity applying eye shadow. She was dressed in a beige silk slip, nude pantyhose, and her open toed slippers. "Aunt Jackie, can I talk to you for a second?" "Sure honey, what is it?" "Well it's Timmy, he's been acting strange lately. I've caught him staring at me and Poly's clothes more than usual." "Well Haley I guess he's just admiring how pretty you all are in your pretty dresses." "No Aunt Jackie, I don't think it's that. I think he feels left out and wants to feel pretty like us." grandmother turned away from her vanity mirror and crossed her legs and her arms. "So what, you think Timmy wants to dress up like a girl?" "Yes Aunt Jackie, I think he does. He won't admit it but I just know that he would if he could." "Ok Haley, thank you for giving me this information. Let me think about things for a while, Ok?" "Ok Aunt Jackie!" Grandmother sat and stared at the floor while thinking to herself, "I've was hoping this would happen, I've been wanting so bad to get Timmy into dresses but wanted him to meet me half way. I think it's time we get him started immediately. The sooner I can groom him then the sooner he will fall into the realm of gentle femininity." Grandmother entered the living room, "Timmy, come into my bedroom for a minute, I want to talk to you." "Ok Grandma." I followed her into her room and she told me to sit beside her on the bed. Her room smelled so sweet and there were slips and dresses hung everywhere. Grandma turned to me with her big beautiful ice blue eyes. She tilted her glasses down on her nose and peeked over them at me. "Honey, I've wanted to talk to you for a while now. You know you've always been the only boy around here and it's been tough on you having to be so different then all of us girls hasn't it?" "I guess so Grandma." "Well I know sometimes you feel left out and you need attention too sweetheart. I know that sometimes you especially feel left out when you see all of the attention that Poly and Haley get." "Yes grandma, sometimes I guess I do." "Don't you think that Poly and Haley wear such pretty clothes sweetheart?" "Oh yes grandma, they always look so pretty and everybody tells them how pretty they are all the time." "Well honey, how would you like to look pretty for a little while?" My heart started racing again and I was so nervous at what grandma my say next. I answered innocently, "But how am I going to look pretty grandma?" "Well I was thinking that just for fun we would dress you up in girl clothes just for a little while were at home. You can just stay in here with me while you're dressed and we don't even have to let the other girls know. What do you think sweetie?" Now my heart was beating very fast and my hands even went num. I was so excited I could hardly stand it. I tried not to sound too enthusiastic but I wanted to dress up so bad. "Ok grandma that sounds like fun." "Wonderful sweetie, you sit here and let me get a few things." Grandma went to her dresser and rummaged thru her top underwear drawer. She pulled out a pair of silk pink panties that has a little ribbon on the front. She also grabbed a pair of light pink pantyhose. i had seen her wear those lovely pantyhose before with her spring dresses. Next she opened another drawer and pulled out a satin white slip. I was so excited with what was about to happen. My cheeks again rushed and I even got a little light headed. Grandma came over and told me to stand up while she got down on her knees in front of me. "Ok sweetie, take off those boy pants and underwear." I quickly yanked off my stupid boy clothes and through them to the side. "Ok sweetheart, now grab on to the tops of my shoulders and step into to these pretty panties." I carefully stepped in one leg at time while holding on to grandma. "There we go honey, now let me pull them up the rest of the way." Grandma slowly and gently pulled up the panties way up over my belly button. She whispered so soft and quiet, "There we go sweetie, nice silky panties for my pretty little girl. They will be a bit big on you honey but you're only going to be in them for a little while. How do they feel sweetie?" "They feel so silky and good grandma." I tried everything I could do to suppress my excitement. I could feel myself getting bigger. Just then grandma got up and said, "Ok, come here sweetie lets get your sweet pantyhose on you." Grandma sat on the bed and picked me up like a baby and sat me on her lap. I could feel her own nylon encased legs on my bottom side and the smell of her perfume was so sweet and girly. "Ok honey these pantyhose are going to be big on you but we'll make them work." She held the rolled up hose in front of my first foot. "Ok sweetie put your little foot in here." I stuck my foot in the hose. Grandma's chin rested on my shoulder and I could smell her hair spray. She smiled and watched my facial reaction as I was putting the pantyhose on. She then put her mouth right up to my ear and with her warm breath gently whispered, "Ok sweetie here we go, on with your little girl silkies. There we go baby." She pulled the silky nylon up to about my knee and then switched over to my other ear. She was watching my face closely and could see how much I enjoyed this whole episode. She again whispered ever so softly right in my ear, "Ok little girl, let's pull on the other leg. There we go sweetie, nice silky little girl pantyhose for my pretty little girl." Once she had gotten the other leg on she said, "Ok let's pull your pantyhose all the way up now." She again turned to look at my face and smiled while saying, "Ok precious let's pull them all the way up high. Little girls wear their pantyhose way up high almost to their breast." She pulled the hose up to just about my under arms and they engulfed me. She snapped the elastic band and said, "There we go sweetie, your very first pair of little girl pantyhose. You are a pretty little sissy girl now." Well that did it, this whole experience and grandmas words burned an impression in my mind that would last forever. And my little pee pee was standing rock hard at attention. There was absolutely no way to hide my obvious excitement from grandma. She smiled at me and hugged me. "Well what do you think sweetie?" My voice was shaking when I answered, "I love them grandma and they feel so nice on me. But why did my pee pee get so big when you put them on me?" She smiled and giggled, "Honey there's a lot to that and when your older will discuss it more. But for now it just shows how much you enjoy being a pretty little girl. It's something that will never go away sweetie. Every time you dress like a girl or maybe even think about dressing like a girl you'll get big down there. You were born like that honey. I'm afraid you were destined to be a sissy. But it's a wonderful thing and we'll have lots of fun being girls together. I want you to be as girly as you want to be and just be happy honey. Now let's get your slip on you sweetheart." Grandma set me down off her lap and on to my feet. I just loved looking down at my stocking covered toes. The feeling of the silk panties pressed firmly against me from the pantyhose was wonderful. I was still embarrassed by my excitement but there was nothing I could do about it. It was like I was finally awakened and a necessary match was made between me and the clothes. "Ok precious, you're going to love this lovely slip. It is pure heaven. Hold your arms up sweetie. Here we go." Grandma put the slip over my arms and gently slid it over my head. From there it lightly fell almost to the floor. It was obviously big on my little frame but you could still see my nylon encased feet peeking out from underneath. The silky slip felt magical as it slid over top of the pantyhose. My heart was still racing and I felt like such a sissy now. "Wow grandma! I really like it a lot. I feel like a girl for sure now!" Grandmother smiled in approval and put her hand to her mouth and began to cry a little. "Grandma why are you crying?" "Oh honey, I'm just so happy you like these things. I've hoped for a long time that you would and I'm just glad it turned out the way it did. Ok, how would you like to put on a little makeup to make you even prettier?" "Sure grandma! I'd like that." Grandma had me sit on her lap at her vanity while she applied lipstick, eye shadow, eye liner, and some bright pink blush. I closed my eyes and became so relaxed as she brushed on the makeup. When she was finished she told me to open my eyes to see what a pretty little girl I was. "Well sweetie, what do you think?" When I opened my eyes to look at myself in the mirror it took my breath away. I looked like a real girl and couldn't believe it. "Grandma I look like a pretty girl! I look like Poly and Haley! Wow I love it!" Grandma again got a little teary eyed and said, "You sure do sweetheart. My goodness you're so pretty!" I was so excited and wanted to go all the way with my new look. "Grandma can you put a bow in my hair like the one Haley has on?" "Sure sweetie, hold on just one second." Grandma opened her vanity drawer and pulled out a fluffy pink hair bow. She pinned it right on top of my pretty strawberry blonde hair. This really made me look like a sissy little girl now and I loved it. "There you go sweetie, do you feel like a sissy girl now with your pretty hair bow?" "Oh yes grandma, I do. I feel very much like a little girl now!" "Ok my pretty little girl let's find you a cute dress." Grandma set me down and went over to her closet. She search thru a few dressed and pulled a couple of them out to get a good look. She put several back until she came across the perfect dress. "Oh honey here we go, this one will be perfect for you. I haven't been able to fit into this thing in five or six years. It will still be big on you but not too much." The dress was half silk and half polyester. It was bright white but had pink and purple flowers throughout. It was more of a mini dress but for me would be an ankle dress. grandma placed the dress over my head. My slip was longer and showing underneath. "Well your pretty slip is showing sweetie and normally that's unacceptable but were only playing dress up in here so it's ok." I stood in front of the full link mirror and just kept staring at myself. I couldn't believe how pretty the little girl was staring back at me. I had been totally transformed. I could feel the clingy pantyhose tingling my legs and felt the elastic band of the hose tugging way up high against my breast. It was reminder of how much of a sissy I was. My breathing had become more relazed and my arms and hands felt lighter. I twirled around in a circle like I had watched many women on TV do. My dress flung up and my wrist and hands got very limp. Yes I was truly a little sissy girl and I loved it. Grandma sat back down at her vanity and continued applying makeup. I just stood there watching her and learning the various techniques of making herself look beautiful. After a few minutes the door to grandma's bedroom swung open. It was Haley and Poly! Both of their mouths dropped and they both put both covered their mouths with both of their hands. Their eyes were as big as quarters. Poly was the first to shout out, "Oh my God Timmy! Look at you! What a sissy!" Grandma quickly got up and stood in front of me to block them from further inspection of me. "Oh Timmy I'm so sorry, I could of swore I locked the door! Don't you girls believe in knocking?" Haley then swung around grandma grabbing onto her leg while leaning behind her to catch another glimpse of me. "Timmy, I knew you wanted to be a girl. I just knew it!" Haley lifted up my dress to reveal my silk slip. "You even got a slip on!" Poly then ran around grandma's other side and quickly lifted up my slip. "And he's even got panties and pantyhose on. That's so funny!" Now Haley and Poly were laughing hysterically while pointing at my privates. Poly then screamed out, "Look Haley, his little thing is hard. He must like being a sissy!" I was so embarrassed. I was now bright red in the face and wanted to just go run and hide. But now it was too late and for some weird reason I actually liked being teased by them and called a sissy. Grandma shoved them both back away from me. "You girls stop teasing Timmy now. He just wanted to dress up to feel pretty like you two girls. He's just as much entitled to that as you. If you two don't pipe down I'll put you in boy clothes and take away your pretty dresses!" The girls instantly stopped laughing but still had apparent smirks on their faces. I could hear Aunt Rachel out in the hall way. "What's going on in there...What's all the ruckus girls?" Aunt Rachel entered wearing nothing but a pair of pantyhose and her slip. She still had a towel on her head. She was not even two steps thru the door when she stopped abruptly. Just like the two girls her mouth dropped, eyes got big, and both her hands covered her mouth in shock. "Oh my goodness! Timmy you're dressed like some kind of sissy! Jackie, what on earth!" Aunt Rachel approached me and walked around me in a circle. She lifted the front of my dress and stopped for a moment. "You even got a slip on child." She then proceeded to lift up my slip and immediately took in a loud shocking deep breath. I think my little pee pee was the hardest it had been. It was pulsating from the excitement and made a tent in the pantyhose and panties. "My lord he's got a...." Aunt Rachel quickly dropped my dress down and pointed to Haley and Poly. "Girls get out of here right this instant!" Poly and Haley did as they were told and ran out of the room giggling hysterically. "Timmy darling, why on earth are you dressed in women's clothes?" I glanced up at grandma and she gave an approving nod. "Aunt Rachel I wanted to feel pretty like Poly and Haley and grandma said I could dress up like a girl." "Is that so, well you go to the bathroom right now and get changed back into your boy clothes. I want to talk to your grandmother." I quickly picked up my boy clothes and ran to the bathroom to change. Aunt Rachel shut the door behind me. "Jackie, what in the hell is going on here?" "Rachel, you know how much I want Timmy to be raised properly and how much I want him to be respectful of women. By letting him explore his feminine side it will ensure that he grows up right Rachel." "So you want to dress him up like a little girl to do this?" "Yes I do. I think it is the absolute best way for him to stay in touch with his feminine side. The clothes will always be a reminder for him." "But Jackie, you're going to turn that kid queerer then a three dollar bill by dressing him like that! Did you see his little thing? He was hard as a rock! That's not good!" "Rachel, he was obviously born like this. No other little boy would get an erection like that if you put them in a dress. And any other normal little boy would fight like hell before you got them in a dress. For petes sake Rachel, you know how much Timmy acts like a girl most of the time. He has acted like a sissy from day one. We might as well let him be a full blown sissy and let him wear girl clothes. "Well I guess your right Jackie, he has always exhibited sissy behaviors. It's kind of funny watching him run around with Poly and Haley with those swishy little arms of his flinging like a little girl. Well we'll have to keep this quiet Jackie. And I'll explain to the girls that they now have a new sister!" Grandma smiled and clapped her hands quickly together in excitement. "Oh Rachel, it's going to be so much fun going shopping and buying him his own clothes. He is going to love being a girl!" "Let's get him back in here. Timmy please come back in here sweetie. Everything is just fine. Now come get up on my lap and let's get some pretty white tights on you. Haley! Poly! Please come back in." The girls ran in quickly still smirking and giggling. "Ok girls. Timmy is a sissy so he is going to be your new little sister. Here we go with some tights for the sissy." Grandmother pulled the tights up as high as she could while Timmy looked down sheepishly at his growing pee pee. One the tights were on grandma said, "Get use to tights sweetie. You'll be in them for now on and for the rest of your life!" To be continued>>>

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

3 years ago
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Saturday Morning Sissy

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

2 years ago
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Revenge of The Sissy

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

3 years ago
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I Sissy

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

3 years ago
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The Farm School Sissy

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

2 years ago
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Becoming a Sissy

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

3 years ago
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What is a Sissy

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

1 year ago
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I would be the Young Sissy

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

2 years ago
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I Want To Be A Sissy

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

2 years ago
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My sisters their friends and me their sissy

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

4 years ago
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Young Sissy

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

4 years ago
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Rules for sissy

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

2 years ago
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Raised a Sissy

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

2 years ago
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Curiosity Spanked the Sissy

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

2 years ago
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Tweak Chapter Three Birth of a Sissy

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

3 years ago
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Beth and Sissy

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

2 years ago
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The Making of a Sissy

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

2 years ago
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Andrew the Unsuspecting Sissy

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

4 years ago
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Sunday Night Football Sissy

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

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

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

2 years ago
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A Happy Sissy

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

2 years ago
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The Blushing Sissy

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

2 years ago
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Degraded Sissy

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

2 years ago
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How to Build a Better Sissy

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

3 years ago
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Checkerboard Sissy

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

4 years ago
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Trucker Daddy Gets A Sissy

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

2 years ago
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Saturday Night Sissy

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

3 years ago
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The Blushing Sissy

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

3 years ago
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Home Alone Sissy

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

4 years ago
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Be a Sissy

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

3 years ago
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Sissy On Sissy

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

2 years ago
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Mrs Grant and her new Sissy

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

3 years ago
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New Little Sissy

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

2 years ago
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Its Hard For This Sissy

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

4 years ago
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stepson becomes moms sissy

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

1 year ago
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My Sisters Sissy

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

3 years ago
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A Nasty Daddy gets a Naughty Sissy

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

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

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

3 years ago
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What does it mean to be a sissy

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

1 year ago
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What does it mean to be a sissy

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

2 years ago
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  • 29
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What does it mean to be a sissy

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

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

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

2 years ago
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The Misadventures of the Worlds Worst Sissy

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

2 years ago
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First time Sissy

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

Transsexual
2 years ago
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Im Not A Sissy

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

2 years ago
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Richard the Sissy

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

3 years ago
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The Lingerie Salesman Sissy

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

4 years ago
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son turned into moms sissy

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

3 years ago
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Cum Craved Sissy

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

2 years ago
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sissy

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

2 years ago
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From manager to sub sissy

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

3 years ago
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Irsquom my Wifersquos Sissy

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

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