Aunt Brenda's Sissy Girl free porn video

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I was raised by Grandmother and my Aunt Brenda from about the time I was six and a half years old. My mother was very young when she had me and my father was nowhere to be found. My mother had good intentions of raising me but she was very irresponsible and just wanted to party all of the time. From the time I was born my Grandmother and her sister, my Aunt Brenda constantly baby sat me because my mother was out doing other things. My earliest memories of dressing in womans clothes were when I was about six and a half years old. I remember wetting the bed a lot by accident and my Aunt Brenda teasing me telling me I was too big to wet the bed. One day my bed wetting had finally sent my Aunt Brenda over the edge. She made me strip my wet underwear off and told me to sit down until she returned. When she came back she was holding the frilliest silk pink panties. "Get up young man or should I say little girl. Since you've gone and wet the bed like a little girl you will be treated like a little girl." I remember that she spoke firmly but gently at the same time; almost in an encouraging way. "Get up and come over here to Aunt Brenda sweetie." I got up and walked over to her and she swung me around by my shoulders until I was facing away from her. "Ok sweetie these are Aunt Brenda's panties and they are going to be big on you but we will make them work. Now lift your leg up honey and step into these." I stepped in one leg at a time as she helped each foot thru the very silky satin panties. While she was pulling them up slowly she turned her head around at my level so she could watch my expression. She smiled delicately and whispered slowly in my ear. "There we go honey, see how nice and girly those feel. Little girls wear their panties way up high over their belly buttons, almost to their bobbies." I remember looking down as she was pulling them up and I new it was so girly to be wearing panties. I could smell her perfume and her soft whispering in my ear was mesmerizing. I was looking down at my little feet next to her pantyhose encased feet while feeling the panties on my penis. She and my grandmother always wore pantyhose with slippers around the house. They were both divorced and in their mid 50's. They were both so feminine and had the softest squeakiest voices that were always so comforting. I know I was only 6 ? years old but my little penis was harder than a rock and that is the honest truth believe it or not. I knew I was being punished for wetting the bed but I was very much enjoying the whole experience. It was like slow motion as it all happened and I could feel the blood rushing to my cheeks. "Ok sweetie how do you like wearing panties?" I put one finger in my mouth and looked up to her and said, "I don't know Aunt Brenda." She then got down on her knees, grabbed me by the hips with both hands and looked me in the eyes. "What do you mean you don't know sweetie? Panties are for girls and not little boys. You are supposed to not like them honey. So are you telling your Aunt Brenda that you like wearing the panties?" Before I responded I looked down at the panties again and noticed my little penis was rock hard and making a little tent in the panties. Being only 6 ? years old it wasn't much but it was noticeable. I didn't know what to think. For fear of getting into more trouble I responded with, "No Aunt Brenda I don't like wearing them." She then cut her eyes and gave me a hard look as if she knew I was lying. She didn't say anything about my obvious excitement and got up and grabbed my hand. "Come on dear let's go show Granny what a little girl you are." She dragged me down the hall and into the living room where my grandmother was propped up on the couch reading a book. She had both legs up on the couch in a kneeling position with her dark nude pantyhose encased legs supporting the book. She had a very pretty pink twin set sweater on and a lace white skirt. She was always so prissy even in a casual atmosphere at home. As we approached my grandmother on the couch my Aunt Brenda pulled me behind her. "Judith, we have something to show you." My grandmother looked up slowly and rested her reading glasses on her nose as she tilted her chin down to look over her glasses to see what my aunt wanted. "What now Brenda, I'm really into this book, can't it wait?" "No it can't. Your grandson has wet the bed for the fourth time in one week. I'm sick of washing sheets on a constant basis. For Pete's sake Judith his little three year old cousin Heather stopped wetting her bed when she was barely three. So I've come up with a plan. If he insists on wetting the bed like a little girl then we'll treat him like a little girl." My aunt then stepped quickly out of the way and grabbed me by the tops of my shoulders. There I stood pouting with my head down in nothing but big pink satin panties. "Oh my God Brenda what have you done!? Jason come over here to Granny." I walked over slowly and she grabbed me by the waist and spun me around inspecting me. She chuckled and looked back at Brenda. "Isn't this a little extreme Brenda?" "I don't think so Judith, little boys don't like being teased and dressed up like little girls so maybe after a few days of wearing panties he'll get the message and start peeing in the potty." My grandmother was still smiling at my embarrassment. She grabbed both sides of the waist of the panties and pulled them up even hirer then they were. She then took one finger and raised my chin up and looked at me. She too had the sweetest smelling perfume and the pinkest finger nails. Her lipstick was just a pink and her baby blush cheeks were so pretty. She then whispered, "Honey what do you think about the panties, do you like wearing them?" Again I knew the best answer was just to say no but I was so confused. My little stick was still raging hard and making an even bigger tent. "No granny I don't like them." My grandmother then leaned back on the couch and rubbed her pantyhose encased legs back and fourth like she'd always done when she was thinking. "Are you sure Brenda? He looks so sad." Brenda sighed and said, "I'm absolutely sure!" My grandmother looked at me up and down again and I noticed her eye movement fixated on the bulge in the panties. She looked back at me quickly hoping I didn't notice. "Well Jason your aunt Brenda is right. We can't have you wetting the bed almost every night. You're too old for that sweetie. Let's keep you in panties for a few days and see how it goes. If you stop wetting the bed we'll let you take the panties off. Does that sound fair honey?" I shook my head yes. "Ok we'll run along and get ready for bed." She then kissed me on the forehead and I ran off to my room. "Brenda I'm worried about this whole thing. Did you see how hard his little thing was?" "Yes I did but I don't think it's any reason to worry at all. Little boys get erections all the time brushing up against things. The silk fabric is soft and it got him aroused briefly. No big deal. For peat's sake Judith he's only six and half years old!" "Ok if you say so, but we need to get him back into mail clothing as soon as possible. You know what happened with your ex husband remember?" Brenda's husband of 24 years tuned out to be queerer then a 3 dollar bill. She had always suspected things but never thought it was true until she walked in on him and another man one day after she came home from work early. He or should I say "she" was down on her knees sucking off some guy passionately. I know this because she told me the whole detailed story when I was 16 years old. That comes later in the story but basically she had dressed up in pink tights, a very frilly white silk lace long sleeve dress, and had lace white gloves on while she held this guy's huge dick with both hands down on her knees. She had perfect makeup on, pink painted nails, and very girly jewelry on. My Aunt Brenda watched the whole 30 minute session thru a crack in the doorway. She let things go on because she was already not in love with him anymore and wanted to see just how gay he really was. I remember her telling me every detail about how much her husband enjoyed it and how absolutely sissy gay he was. She said that she was on her knees and she kept her legs together so tight and girly. She propped up so sissified occasionally putting one of her lace gloved hands on her pink tight encased knees. She even tilted her head sideways exposing her diamond earrings in a very feminine girly way. She said he was born to give blow jobs because men get off by not only being sucked by a woman but by the feminine girly things they do while their sucking their man. Thinks like quickly tucking their hair back behind the ear and sticking out a pinky finger as they jerk off a big cock. My uncle did all of this and even cooed and moaned like a little sissy girl. My aunt even remembers what the guy was saying as he was being sucked by my uncle. "Are you my little girl who likes sucking cock on her knees? You like wearing pretty pink tights and silky dresses don't you baby? You're a sissy and I can't believe you even have a wife. You suck dick better then her I bet." My uncle was such a sissy and my aunt could not believe how gay he was. She wanted to see this hairy man he was sucking cum all over her disgusting husband's sissy face. The man was grunting hard and getting close. My uncles little pink encased toes were curling up in anticipation and his pinky was poking out just like a little girl. "Ok sweetheart here's what you been waiting for." He grabbed my uncle up under her blonde curly wig and cuffed her neck to take control. "Here ya go sissy, tell me you're a sissy in pink tights who likes sucking dick." As my uncle was jerking him off faster in a girly moaning tone my uncle says, "Oh I'm such a sissy in pink tights and a dress and I want your cum on my face." The man squirted cum all over my sissy uncle's face and on to her dress and tights. She moaned and twitched just like a little girl. She placed both white lace gloved hands on her knees just like a prissy little girl. Cum dripped down her chin and onto her tights. The man said as he breathed so hard, "That's a good girl. We're going to have to wash your pretty tights because you got cum all over them." My uncle looked up to him with a very girly over-bite smile and said, "Am a good sissy?" The man said as he stroked the back of her head like a little girl and played with her pink hair bow, "Oh yes you can never go back to being a man. You are a sissy little girl who will be in tights and panties for the rest of your life." My uncle then stuck one finger in her mouth and bit down like a little sissy and said, "I want to always be your sissy. Can we buy me some pantyhose so I can be a big girl?" At that point my aunt walked in right past my uncle and the man. My uncle was in such shock that he didn't even move or let go of the man's cock. He knew it was pointless. My aunt walked over to her dresser and grabbed an unopened pair of white pantyhose and two very filly pink hair scrunches. She walked over to the both of them and tossed the pantyhose onto my uncles cum covered knees. "Here ya go sissy, they're not sissy pink but glittery white is pretty damn girly." She then took the back of my uncle's blonde wig and put the pink scrunche on to make a ponytail. "There now you're a good little girl who won't get cum in her hair next time." She took the other scrunche and put it on the man's now limp cum covered cock. "Ok so you two sissies are made for each other. Frank I always knew something wasn't quite right with you. I'm not mad I'm relieved. And yes you do suck dick better then me. You're such a flaming sissy. I knew you were wearing my clothes. My pantyhose have been stretched out for years because of you. God look at you on your knees in pink tights! You got your wish Frank. You can be a sissy for now on! Now both of you disgusting fags get the fuck out of my house and never come back." That was the end of the marriage right there. "Oh yes how could I forget that Judith. Thanks for brining that back up. I'm not going to turn my nephew into some sissy." "Ok Brenda I trust your judgment, I just want to monitor the situation that's all." When I went to my room I stood in front of the mirror gazing at myself in the mirror. I ran my fingers all over the panties and touched my penis. It felt so wonderful. I was too young to have an orgasm at that time but the feeling was still incredible. The next morning when I woke I immediately examined myself. I had not wet the bed and was very proud of myself for staying dry. My granny entered my room wearing her usual long pink nightgown with her hair in a white hairnet. "Well good morning sweetheart how are we this morning?" "I'm fine granny. I didn't wet the bed!" "That's wonderful darling! I'm so proud of you!" "Let's go tell your Aunt Brenda!" Granny grabbed me by the hand and led me into the kitchen where Brenda was sitting eating a bowl of oatmeal. She was a little more dressed then my granny as she was getting ready to go shopping. She had on a satin white slip with pink flowers around the breast. She had on sheer white pantyhose and you could clearly see her pink toenails shinning thru. She always dangled her feet up and down when her legs were crossed and it always got my attention. "Brenda guess what? Jason did not wet the bed last night!" "Well that's a first in a long time. I guess the panties worked huh sweetie?" I was still very embarrassed to be standing in front of these two ladies in panties and I bashfully replied, "Yes Aunt Brenda I guess they did." "Well we will just have to keep you in them until we are absolutely certain that your bed wetting has stopped." For the next 4 nights I was put into different colored panties, yellow, blue, and white; they were all as silky as the first pair too. It was Sunday morning and I had now gone four entire nights without wetting the bed. Aunt Brenda entered my room half way dressed for church. She had on a black full slip and sheer black pantyhose. She sat down on the bed as I was waking up. She always wore the strongest of her perfumes on Sunday's and the aroma was heavenly. "Well good morning sweetie. How'd we do last night, did we go 4 for 4?" She pulled the covers down and to both of our surprises I had not wet the bed again. My penis was getting hard again however and making a very noticeable lump in my panties. "No Aunt Brenda I stayed dry again! Can I have my boy underwear back now?" "Well not just yet honey. I want you to wear them today under your clothes at church today. You're always so fidgety at church and I think the panties will help you behave. After church I'll let you change back into your big boy underwear." I let out a big sigh and pretended to be upset. "But Aunt Brenda you said..." "I know what I said young man and I'm saying right now that you'll wear panties today at church and later I'll let you back in your own underwear. And there's one other thing I want you to wear with the panties." "What's that Aunt Brenda?" Just then she reached down and grabbed my hand. "Here give me your hand." She took my hand and placed it on her pantyhose encased leg and started to rub it back and fourth. "You see how smooth and silky my pantyhose feel. Wouldn't you like to wear some pantyhose just like your granny and Aunt Brenda?" At that moment I was so nervous but getting so excited about being able to wear pantyhose. I responded, "Ok I guess so." "Good sweetie I knew you'd say yes. Stay here and I'll be right back sweetie." When she returned she carried a very light pink sheer pair of her pantyhose. I had seen her wear that pair with her spring dresses before. "Ok here we go." She lifted me up and placed me on her lap like a little baby. She reached over me and started to put one foot into the pantyhose very slowly. I could feel her own pantyhose encased legs on my own legs and her perfume smelled so girly and sweet. She got right in my ear with her warm breath and she whispered oh so sweet and softly. "Ok here's the first little leg slipping into these little girl silkies." She started to pull them up past my knee slowly. "Ah yeah beautiful pantyhose for my little sissy girl." She continued with the other leg. "You're gonna feel just like a pretty little girl with these on under your pants sweetie." She lifted up my bottom and pulled up the pantyhose oh so high over my little chest. Now my little stick was the hardest it had been yet. "There we go all the way up high just like your granny and Aunt Brenda now. Wiggle your little girl toes for me. She had sheer and pretty they feel! Now you can walk around the house in silky pantyhose and be pretty." It was at that moment that the words burned an everlasting impression in my mind. I had officially been sissified and would never be quite normal again. As the years went on my Aunt secretly dressed me in panties, slips, nightgowns, pantyhose, tights, and dresses. When my granny wasn't there I would often ask Aunt Brenda if I could be her little girl. We played dress up constantly and she taught me everything feminine. How to sit, walk, talk, and all the feminine girly things that girls do. As I got older I dressed as a girl as much as I could and Aunt Brenda knew how excited I got. She would tell me to go to the bathroom whenever I got too excited and let out my sissy juice. She said the more that I became a sissy girl that the more juice I would have to let out and that the more juice let out that the more of a little girl I would become. We bonded thru the years and she encouraged me to be a sissy and knew I would end up being some man's little sissy some day. When I was 16 I had my first sexual experience. I dressed up in a pink dress with white tights and a pink bow in my hair. My granny was on vacation out of town and Aunt Brenda did all of my makeup. When my date arrived my Aunt Brenda left. It didn't take long before we were in my bedroom and I was down on my knees. It felt so right to be so submissive for this good looking strong man. I don't think he was quite gay all the way. He knew I was a little sissy and he was turned on big time by that. I must have sucked him for a half and hour before he said these words, "Ok sissy this is the life you are choosing, a life in pantyhose and slips and dresses down on your little knees. There's no turning back once I cum in your mouth and you swallow it like a good little girl." I let out a sissy moan and begged for his cum as I held him with both hands with my white lace gloves. "Ah AHH AHH, I'm cumming sissy I'm cumming!! Oh God I'm cumming all over you sissy bitch!!!" Mounds of creamy white cum splattered in my mouth, over my lips, onto my forehead and down onto my pretty white tights. I moaned and licked all around his huge cock. I felt so much like a girl at that moment. "There ya go sissy. You're officially a sissy little cock sucking girl." Later that night my Aunt Brenda and I sat on the couch together. We were both wearing pink nightgowns and white pantyhose while painting our fingernails matching pink. I asked her, "Well do you want to know how our date went?" She smiled and said, "Please don't be mad at me sweetie." "For what Brenda?" "I couldn't help it. I ended up watching you and that boy having sex." "Oh my God I'm so embarrassed Brenda!" "Please don't be sweetheart, you've always wanted to be a little girl and now you've become one. He was hot too! Now let me tell you a story about my ex-husband....... The End

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

4 years ago
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She Found a Sissy

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

4 years ago
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100 Sissy Points

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

4 years ago
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Welcome Your Now a Sissy

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

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...

2 years ago
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A sissy called Jezebel Part II

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

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...

4 years ago
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Aunt Fionas Girls

Hi. My name is Britney Burris, and I'm from the tiny suburban community of Apple Valley, Washington. My best friend growing up was Jessi Nolan, and during our teenage years we both had huge girl-crushes on her Aunt Fiona, whom we both thought to be the coolest woman on the planet.Perhaps I should tell you a bit more about Jessi & myself before continuing. While we're the same age, we had our differences. I'm tall, blonde, and slender, while she's a bit shorter than me, but also very...

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...

3 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...

2 years ago
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Aunt Fionas Girls

Hi. My name is Britney Burris, and I'm from the tiny suburban community of Apple Valley, Washington. My best friend growing up was Jessi Nolan, and during our teenage years we both had huge girl-crushes on her Aunt Fiona, whom we both thought to be the coolest woman on the planet.Perhaps I should tell you a bit more about Jessi & myself before continuing. While we're the same age, we had our differences. I'm tall, blonde, and slender, while she's a bit shorter than me, but also very...

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."...

2 years 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...

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...

2 years 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...

2 years 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...

2 years 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...

2 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

1 year ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets 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. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Jamie Peregrine's...

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