I Want To Be A Sissy, Part 1 free porn video

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Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or not! Please! Please! Please! I have tried so hard to improve my bust. "I must, I must, I must improve my bust!" Three months ago "my bust" would have seemed foreign to my ears. Times change. So do Sissies. ___________________________________ My name was Jim (Ugh!) and Mistress's name is, do I dare to speak it, Claire. I am 35 and she is 33. Well I was 35. Sissies do not have ages. They just are. So I am whatever Mistress wishes me to be in age. I hate diapers! We were both Trust Fund babies. No problems with money. Never had and never will. So convenient. Made our life easy, in most ways fun and carefree. Nice house on the beach in Malibu. All we could ask for. And we loved each other and were happy with our blessings. And the sex was good. Not good, Fantastic! We did everything possible without breaking our backs or any other part of the body. And we so enjoyed it. Doctor, nurse; Nurse, patient; most members of the Village People; even Priest, nun! One evening, after the studly fireman saved the sweet 16 year old Princess from the burning castle, we were lying, exhausted on the king sized bed. Claire rolled over to me and pinched my right nipple. "Oh, Jim, you were so strong! You saved me! I hope I thanked you properly?" I moaned: "Just what any red blooded sexual object would do, and yes, you did! Several times!" She tweaked my manly nipple. Hard! A few minutes later, Claire turned to me again and pinched the other nipple. "Jim, let's be serious for a moment. In all the love making we have done with each other, is there any one thing which we haven't done, which you would like to try? "Gee, Claire, I don't know. What can I say. You are marvelous and I think I make you happy. Is there something we are missing?" "Oh, I was just thinking that there is probably something that we haven't done, but maybe we are too embarrassed or too shy to even talk about." "There is not too much which embarrasses me, Claire." "Well, I am ashamed to admit it, but there is one thing I have always wanted to try, if only for a little while. "I would like to try being a Dominatrix! There I said it! Do you think less of me?" I was stunned. My little Claire as a Dominatrix! OH MY GOD! I surely didn't think any less of her. I was fascinated. "Claire, go for it! I will help you any way I can (grin grin)." I am not above a little kinkiness. "Well, what about you? Come on be a big boy. There must be something that you would like to happen to you, that you have been too embarrassed or too shy to tell me. Now is your chance. What ever it is, you deserve it. Go for it, Jim!" I was staring to sweat. What could I say? Could I say it? "Come on, Come on! We love each other, out with it!" Finally a small voice mumbled something. "What did you say? You were speaking so softly, I couldn't hear you. Speak up like a man! You can do it! Nothing will surprise me or make me think less of you." A slightly bigger voice said: "I want to be a sissy!" There was a long pause. Claire was very still beside me. Her fingers, which had been kneading my nipples, lowered to her side. I felt her breathing fast and deeply. Finally: "You want to be a sissy?" "Well, only for a little while. It is just something that has always fascinated me. And I have never tried it. Lord, no! And you said if there was one thing we had never tried before. So that is it." Claire laid there in thought. So did I. She spoke first. "You know if I want to be a Dominatrix and you want to be a Sissy, we could help each other tremendously. It wouldn't have to be something long term. Just a little while, like you said. And we have the money and the time and the place to be what we want to be. Why shouldn't we?" "I agree. I will do whatever it takes to help you be the Dominatrix of your dreams." "And believe me, if I am a Dominatrix, you will be a Sissy!" Claire thought some more and leaned over once again and came on top me and tweaked both my nipples at the same time, then smiled. "Let's do this right. Let's pick a date to start this fantasy. As of that date I will be a Dominatrix and you will be a Sissy. Before hand let's use our money and set up whatever we need to do the job correctly. I can see a spare bedroom becoming a discipline room and another bedroom becoming a beauty salon. I can see latex clothing and diapers and pinafores and handcuffs. This will be fun. Let's do it!" "OK, but how about I set up the stuff you will need to be a Dominatrix and you can get all that is needed to make me a Sissy. That way we will both be surprised when the day comes." "Excellent idea. It will be so much fun. Something new and quite different for us. I suggest one month from today that both of our lives will change, at least for a little while. And we will have fulfilled our deepest dreams." "One month!" ____________________________________________ Jim There is so much information and resources you can find on the internet. And if you have money, it can be yours. The next few weeks hurried by. I got into my part of the set up quite intensively. Boxes arrived of which Claire was not allowed to know the contents. I became quite adept at a screwdrivers and wrenches, because almost all the equipment I had ordered had to be assembled. It was a lot of fun. Even if I didn't have a complete idea about what some of this stuff was used for. I had to ask Claire for her measurements in order to order the proper couture for the budding Dominatrix. I think everything should fit her. Seeing the get ups, I am looking forward myself to seeing her in them. In the third floor bedroom I installed an enlarged closet to hold all her clothing, neatly hung. After hours of assembly, wooden benches and stainless steel tables were ready to receive a willing or unwilling body. There were stocks and racks with wrist and ankle restraints, bars from which to suspend or hang an unfortunate person. One wall was covered with accessories, such as; butt plugs, nipple clamps, leg spreaders, assorted hand cuffs and neck restraints, and an awesome display of every size and functionality of dildo the well equipped Mistress could wish for. One corner of the room held a steel barred cage the size and height of a kennel for a large dog. Inside the kennel were two steel bowls and a steel bucket. In the center of the room was a stainless steel adjustable operating table. It could be used flat or tilted or configured into a U shape and into an upside down U shape. There were three operating room lights hung from the ceiling over the table. Around the table were utility tables holding all manner of medical instruments, stainless steel and shiny. Also near by were Medical holding racks holding enema bags and tubes of all lengths and circumference. The most terrifying piece I had ordered was the Gynecological Exam Chair. That scared me. The operating lights would be able to be used on this apparatus also. My Claire would have all she desires for her fantasy of being a Dominatrix, provided by her loving Jim, unquestionably and somewhat nervously. ____________________________________________________ Claire Jim has been a busy little beaver, hustling around, building, measuring, painting, making the worst racket. He seems so happy. I have been busy also. It was so much fun to stand Jim up on a short stool and measure every inch of his body. Over the past few weeks I had read up on what being a Sissy actually meant. I was surprised to find out that I had choice as to what kind of Sissy I wanted Jim to become. I didn't ask Jim because I am the Dominatrix and he is the Sissy. Duh! There is the Baby Sissy. Complete with diapers, bottles, baby food, pinafores, high chairs, cribs and potty training I think not. Too messy! There is the Little Girl/Teeny Bopper Sissy. Complete with bows on pigtails, raging hormones, crinolines, petticoats, training bras, party dresses and first periods. I think not. I don't like teenagers, sissies or not. Too unpredictable, and they cry a lot. Then there is my choice for Sissy type. The Humiliated, Effeminate, Feminized, pseudo woman, pseudo man who cringes at his/her state but secretly wants to become more and more female while the Dominatrix keep him/her just past the humiliating edge of sissydom. My work over these three weeks centered on the bedroom on the second floor with the attached bath. The room was painted light pink with gold trim. The four poster bed was resplendent in sheer lacy white ruffled bed curtains. The sheets were water stained silk of the deepest burgundy with pink piping. There were fifteen ruffled pillows, all in pastels, piled high at the head board. There was a professional stage lighted make up vanity with three mirrors on one wall and on another wall were huge closets containing the frilliest and most ruffled frocks and skirts and blouses and the highest of pumps arranged by color. The bathroom I had converted into a complete beauty salon for my Sissy. Just the sight of the huge stainless steel, torpedo shaped, 1940's salon dryer attached to the ceiling and ready to consume any Sissy in sight, gave me the chills. Bows, rollers, perm rods, end papers, hair nets, bobbie pins, nylon capes, nail polishes, bottles of dyes and shampoos and conditioners filled every drawer in the shampoo cabinet. The styling chair, with numerous restraints to contain the nervous Sissy, sat under the dryer on a slightly raised pedestal. Next to the styling chair was a complete department store cosmetic counter. Everything that could feminize and humiliate a Sissy was there. There were also a few pieces of strange machinery placed by the styling chair. I will not describe them right how. I just needed a Sissy to wander by. I love my Jim. I am only too happy to make him the Sissy of his dreams. __________________________________________________ The month is up tomorrow. "Jim, do you think we will sleep tonight?" "I haven't slept for the past three nights. Are we doing the right thing? Do you still want to go through with our plans?" "Jim, darling, I know I still want to try being a Dominatrix. I think I will be a good one. But it seems to me that once I become one, you will bear the brunt of whatever activity happens from that time on. Are you ready to obey your Mistress and be humiliated and shamed and even be in pain because of your desire to be a Sissy?" "Claire, I love you and hope you still love me during the time I am a Sissy. But I want to experience what every Sissy experiences at the hands of a demanding Mistress. That is part of the thrill and the horror of being a Sissy. I will no longer be a man or a woman. I will be an abject Sissy and you will be my benevolent, but stern, Mistress. While you learn how to be a Dominatrix, I have to learn how to be a Sissy. No matter the pain or the humiliation." "OK, as agreed, this arrangement is for the period of one month. Unless, I, as the Dominatrix, want to extend your Sissyhood. As a Sissy, of course you have no say. It that correct?" "Yes, Claire, as of breakfast tomorrow, you are my Mistress and I am your Sissy!" "Let's go to bed now and sweet dreams, my love." "Jim, before you come to bed, when you go into the bathroom, please sit down on the toilet to relieve yourself!" ______________________________________________ I did sleep very well. I couldn't believe it. When I awoke I heard Claire bustling around in the Discipline Room which I had prepared. The vixen! She couldn't wait till after breakfast. But I guess being the "Mistress" gave you options not available to a mere "Sissy". But I was hungry. So I dressed quickly as I would any day. The kitchen was deserted as I expected. There was a note on the table: Good morning, sleepyhead. Breakfast is on the stove, enjoy! I will be down soon. And the breakfast was very enjoyable. Bacon, sausage, eggs and toast. Just as I was finishing the last bite, Claire was behind me and put her hands, very strongly, on my shoulders. "Jim, dearest, are you finished with breakfast?" I tried to turn around but she wouldn't let me. "Well, good morning, Claire. Yes breakfast was quite delicious!" "Then breakfast is over. You are mine, Sissy! Get down on your knees now! Don't say a word! Do as you are told and nothing else!" I dropped to my knees at Claire's harsh tone. She came and stood in front of me. My God, she was wearing a deep burgundy leather bustier over tight black leather pants and 4 inch black patent fuck me heels! "On all fours, pussy Sissy, kiss my feet, lick my heels and the soles of my pumps!" She sat, regally, in the chair that I had been using. I lay prostrate at her feet. A high heeled pump lowered itself to my mouth and my tongue at once leapt to embrace the dangerous heel. I kissed and licked each offered heel and when the sole was turned up to my eager tongue, I licked the soles of each foot. A pump clad foot came to my mouth and pressed on my lips, I had to open my mouth. And the devilish shoe slid inside my mouth. The tip on the pointed pump played with my tonsils. "I am your Mistress, Sissy! You may call me only "Mistress" or "Goddess"." "I will call you, Wendy Sissy!" "You are not to speak to me unless I allow you to do so. Do not disobey me in anything. If you do there will be severe punishments. I see that you have done a very good job on my Discipline room. You might not think that was a good idea after you have been punished, as all Sissies have to be. "I hope you enjoyed that breakfast because that is the last meat you will taste while being a Sissy. I will feed you what I choose, when and if I choose. If you displease me, that meal may be dog food and you will have to lick the dish clean!" "Now get up, wimp! Keep your eyes downcast and take off all your clothes. Good Sissy! "Now keep your eyes down but bring your wrists up even with your breasts and allow your hands to go limp. "Tuck your elbows into your side and wiggle your fingers. This position is your Sissy default position. Unless I have you doing something else, you are to maintain this position at all times; standing, walking, sitting." "When I approach you, you are to curtsey deeply. If you are wearing skirts you may move your hands to gracefully gather your skirts for the curtsey." "There will be many many more rules for a Sissy to follow but now I am growing tired of seeing a naked Sissy in front of me. We will have to do something about your nakedness. And also a Sissy should not have such a boyish chest. We will have to do something about that also. So the first things we will do to my new sissy is curl your hair (those sexy curlers will be all that is required at this moment to cover your nakedness) and I have a wild surprise to handle a Sissy's chest." "Turn, Sissy Wendy, and follow me into the quarters I have prepared for you. Sit in the styling chair and Sissy will soon have a head full of prickly wire mesh curlers. (Sissy Wendy) My mouth tastes like crap from the pumps in my mouth and from my tongue licking between Mistress' toes. As soon as Mistress opens the door to the Sissy Room, I see the ruffles and the mirrors and the complete Beauty Salon. This is my Sissy life for the next month, at least. My stomach turns. But Mistress is the Dominatrix she desired to be and I am the Sissy I asked to be. What an experience! Why do I think Mistress is going to enjoy this month a lot more than I. "Sit in the Styling Chair, Sissy Wendy. You may respond if I ask you a question." "Sissy Wendy, how tight shall I roll these curlers into your hair?" "Mistress, as tight as you can get them. I want to be the curliest Sissy I can be for you." "Well said, Sissy! Now lean back and I will shampoo my little Sissy. And then wind your locks as tight as possible because you will be wearing the curlers all day and all night. "How does that make you feel, Sissy Wendy?" "I beg for the chance to suffer pain and humiliation as my Mistress desires!" "Well, I can certainly oblige you in that. Here hold the box of curlers and pins and hand one to me as I need them. Sissies have to help in their feminization" (Mistress Claire) I like this! (Sissy Wendy) Oh, she is pulling my hair soooo tight. And she is not gentle when jabbing in the holding pins for the curlers. So this is what it feels like for a Sissy to get a wet set. So many curlers, soooo tight! It feels so good. I think she in done. What is that? A pink ruffled hair cap is being lowered over the curlers and tied in a bow at the back. Nice touch! Speaking of touch, here come her hands, pressing on the sides and the crown of my head. I experience the pain of the prickly mesh curlers being pressed into my scalp. She loves to press down hard. Now what! OH MY GOD! I see it coming! "Sissy, you are so cute with your hair all in rollers. But now I have to lower this antique 1940's stainless steel torpedo shaped dryer all around your curlers. It is rather frightening, isn't it?" "Mistress, it won't hurt me, will it?" "Such a cute question from a Sissy. So what if it does? You are just a Sissy, not a real woman under the dryer. I hope all the electricity is working well and is safe." "How does it feel to have that powerful machine all around your head?" "Mistress, I am scared. This has never been done to me before." "Well, it will be a daily occurrence for you from now on. But before I turn it on we still have to start doing something about your boyish chest. Sissies are not boys and they are not girls either. But they have to have Sissy breasts to be a real Sissy. Mistresses love to play with, and torment, Sissy Boobs. Guess what?! You are going to have breasts, just like a girl. I have a machine called a Male Breast Enlargement Vacuum Suction Therapy Device. It has been designed for the express purpose of enlarging Sissy breasts to whatever size the Sissy's Mistress desires. For you, Sissy Wendy, for the first month, I desire that you become a B- Cup. You will be attached to this machine three times a day, and during your drying under the dryer will always be a very good time to increase your bust. "Let me get my Sissy all hooked up to the MBEVSTD. It hooks on just like a bra. You will get very familiar with bras very shortly. Let me puts the straps over your arms and shoulders and hook in in the back. In place of bra cups, which are so soft and heavenly, we have two cone shaped cups with rubber gaskets around the open end and a tube leading to the compressor at the top of the cone. I will place the open ends over your breast area and tighten the straps so that there is a tight seal then I turn it on and, voila!, my Sissy's having her breasts pumped up over and over again. "Now, take your hands and hold the cups in place until a proper suction is established. OK, I will turn the MBEVSTD on! "WHOA! That sucker is strong! How does it feel? (Sissy Wendy) Like my chest is being torn off. Suck, pull, hold, release: over and over. Sometimes the hold part is for a long time. Sissy is having second thoughts about this whole thing. "Well that seems to be working well. Now I will turn on the dryer to very hot and I will see my Sissy in about 40 minutes. "Enjoy!"

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

4 years ago
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Sissy School Part 3

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

2 years ago
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Sissy tasks

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

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...

4 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...

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...

3 years ago
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Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

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...

3 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...

2 years 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...

4 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...

3 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...

2 years 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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