I Want To Be A Sissy - Part 3 free porn video

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The car door shut on the cocoon of my last hope of safety from intense humiliation. My fingers trembled at the thought of what I would have to endure to be the Sissy of my desires. I placed my purse on the passenger seat and opened it to see the contents. One lonely and tempting Tampon, a pink cell phone I had never seen before and 200 dollars in cash, tied up in a pink ribbon. Oh, how I wished I would find just a simple lipstick to give me a chance at passing as a woman on my trip. It was not to be. I was what I am and what Mistress desired me to be. It was not far to the drugstore we always used. Which I had used as a man. Now it was to be my first public ordeal of my month of sissification. I am sure several of the clerks knew me by sight as a man. What will be their thoughts as they view me as a feminized Sissy? What will be my thoughts as I see them seem as feminized Sissy. I hoped that no police were near. My nervousness and my terror were making my hands shake on the steering wheel. And the my kitten heels, small though they be, were a new feminine variable that I have to account for on the brake and accelerator. The windows of the car have become a viewing portal for the world to see this budding Sissy. At least that was my overpowering thought as I was sure every driver anywhere near me was staring at my head full of curlers and my lavender spaghetti straps. At stop signs, drivers on either side of me were surely gawking at the ridiculous sight next to them. When I was almost at the store, my new cell phone rang. "Sissy Wendy, are you still in the car?" "Yes, Mistress!" "You know, don't you, that all the drivers around you are staring at you? They will have a great story to tell their husbands or wives at home. 'I saw a total SISSY today, driving down the street!'" "Yes, Mistress, I know!" "Those are people who have just fleetingly seen you from a distance. How do you think it will be when you are standing next to them, looking for lipsticks, or in the check out line, holding your Tampons and Perm Kit? "You will be a pile of quivering feminized jello!" "Yes, Mistress, I know. That is my lot for the next month and you have been doing a wonderful job of being a most skillful Dominatrix. I am experiencing all the Sissydom that I have ever dreamed of. "I am here, at the drugstore, Mistress." " Do not think of anything! Get out of the car. Don't trip on your new girlish heels. Walk in standard Sissy position, right now, into the store. Make those wrist go limp, wiggle those fingers, lovingly pat your curlers. Your first public nightmare is about to happen. You are going to be a SISSY among real people. Let them laugh at you, sneer at your sissiness. That is what you asked for. Enjoy it!" I was here. Super Malibu Drugs and Beauty. This was no ordinary drug store. This was Malibu and everything had to be fancier and plusher. I wasn't going to sneak up and down aisles, looking for my female booty. Here they had knowledgeable clerks in every section, especially in the Beauty and Feminine Hygiene section. I would be asked my needs and they would be taken care of. No solo shopping here, not even for quivering Sissies. I took a deep breath, wishing my top covered a well stuffed bra, opened the door, and watched as the cute ruffled hems on my capris rustled, teasingly, in the slight breeze, even before my Maryjane clad feet touch the pavement with a womanly high heel click. I made sure my curlered head avoided the unpleasantness of the car door. As I ducked to keep the rollers from inflicting more pain, the flounces of my chemise fell down straight and voluminous away from my braless chest. They caught the wind also, I am sure it felt good and sexy but I was too scared to notice. I grabbed my lipstickless purse and assumed the Sissy Position, took three steps, patted my curlers in a most effeminate manner, and went on my way to the humilation I had asked for. Silly Sissy Me! With my purse hung precariously on my shaking shoulder, I minced thru the self opening door into a world which would surely cause me pain and suffering and intense embarrassment. By asking to be a Sissy, this is what I wanted, craved. Now I had to endure it. As i stood patting the rollers on my head with a motion that gave the impression I was fluffing up my "do", time seemed to stop all-around me. The store was quite busy. Too busy for my liking. Excellent for Mistress' purposes. To my left were check out lines and ahead of me to my left were the normal stock of any drugstore. My sissy business was ahead of me to my right - Beauty and Feminine Hygiene. Sales women in pink smocks, floated and fluttered around the area, shelving stock, selling items, doing makeovers, whatever it took to get real women as beautiful as possible. Soon a sales woman would approach me, probably with a smirk on her face. The stoppage of time was over. Real time took hold of me. I was an unwelcome, ungainly sight to behold in a sea of freshly coiffed and precisely painted matrons and their female offspring. Heads around the area popped up from their quest for the perfect foundation, to see me, a blatant MALE sissy, trespassing on woman's turf. Older customers stuck their nose up or snickered behind their painted nails. Younger customers laughed out loud but then seemed to wink and say: Come on in, Fruit, you may be interesting. But they were really about their business which was to make themselves more beautiful for their man or for their woman. As I flitted down one aisle one young (24 or so) lady stopped me in my tracks and patted my rollered head. "You go, girl!" And winked at me. I heard one very young lady, possibly here for her first pink lipstick, ask her mother: "Mommy, what it that?" "That is a Sissy, love, I will tell you more later at home. Don't stare!" I was totally out of my depth, not knowing where to turn, wanting to avoid the laughter and the pointing. I don't know why? That is what I asked to happen to me. Boy, I was getting it! Just to have a fully coiffed head of hair would have made my day. I am sure Mistress will take care of that detail some horror laden day quite soon. Then there she was! Walking directly towards me, a pink smock encasing a no nonsense woman, a woman who radiated her femininity in a powerful way, which said: don't waste my time. I am woman, hear me roar. Her eyes were on me. I was her prey. I was the unknown bug, better to be squashed than to have invade her holy of holies. She stopped three feet in front of me and looked me over from head to toe. Taking an inventory of all that could be wrong with this strange critter. I knew that I was found wanting. I wasn't a woman, my God, I wasn't even a man! She spent an ungodly amount of time gazing at the myriad rollers perched upon my worthless head. Then she spoke to me. "Gee, sweety, that is a lovely brickwork pattern of rollers on your head. Did you do that? I'm Judy, by the way." Huh? I don't hear her roar! "Thank you, Judy, no I didn't. My mistress put my hair up last night. I am looking forward to her styling it when I get home. See, I am her Sissy. And she says she will make be look like Doris Day if I am a good Sissy and follow her instructions. That is why I am here. I have a list of items I must buy to help with my journey to sissydom and femininity. Can you please help me be a good Sissy?" "Well, my land, you have a very great Mistress if she can do a wet set like that! You are one lucky Sissy! Imagine having a Mistress who can give you any hair style she wants you to have. You just might spend the rest of your sissy life in well ordered rows of tight curlers. What more could a Sissy ask for. My husband appreciates a nice wet set and a quality "do" now and then. I have made sure of that. Most men need some strict and demanding feminine discipline from time to time. I know all about sissies. "What can I do for you, Sissy???" "I'm Sissy Wendy, thank you very much. Number one on my list are Lipsticks. I need three, but they must be colors that will make me more and more of a sissy. I do love the idea that Sissies adore lipstick." "I am sure you do, darling. Do you have any special color you know you want or your Mistress wants you to have." "I want to wear Revlon's lipstick color - Fire and Ice. I have heard that all sissies have to have that particular shade. It seems to be a rite of passage into Sissydom. Other than that one, I am sure you might know of colors that would work best for a sissy like me." "Honey, there are so sissies like you. Each sissy is different. Just ask my husband. They are all worthless or they wouldn't be sissies. I bet this is your first time out as a sissy and you are scared shitless. LADIES, we have a new sissy here! The first things he wants are lipsticks! Does anyone have any suggestions for this newbie sissy?" Many of the women who scared me as I minced into the store had now gathered around Judy and I. Most were now smiling. "My thirteen year old daughter just picked out a lipstick called BubbleGum Pink. What could be more "sissy" than that! I would love to see this little twerp with BubbleGum Pink on his lips." "Excellent choice, Madge. I remember when my 15 year old, football playing son was getting into all kinds of trouble. The only thing I could ever do to put a leash on him was to make him wear Candy Apple Red lipstick, 24hrs a day for a week. Geez, when that week was up he was so confused about his future he couldn't cause any more trouble. He finally hung up his cleats and went to Beauty School and majored in Makeovers." "Thanks, Ladies! So, we have Fire and Ice, BubbleGum Pink, and Candy Apple Red for Sissy Wendy's lipsticks!" "Wait a minute!!! We've got a real live Sissy here. I want to see the Sissy put on one of those lipsticks! I love to see men, and sissies, put on lipstick. Every time my hubby does it I get so hot! I think he might have a surprise coming to him tonight. I'll take one of those Candy Apple Red lipsticks myself!" It seems that there are a hell of a lot more men out there who qualify as sissies them I had imagined. And these women seemed to love making any man around into a simpering Sissy whenever the spirit moved them or them their clueless husband did something so horrible he would be encased in a corset for the next month. "OK, Sissy Wendy, this is your first time out in public as a sissy, right? Do you have any skill in lipstick application?" Oh, my God, how I had wanted so badly to be wearing lipstick when I came in this store! Now I had to put lipstick on in front of all these women and girls. I had no skill in putting on lipstick. I was a man before I became a sissy. My sissy training is certainly going into high gear, very fast. "No, I have no training in such a womanly action. But since I am a sissy and there are a lot more of you women than there is of this sissy, I will make my lips a pretty as I can." "What color do you want to try?" "My mistress told me to buy the most sissy colors I could. She said nothing about wearing any of them home, but I better follow her demands and go with the BubbleGum Pink lipstick." "Excellent choice for a Sissy. Here you go, sweety, I even opened the tube for you." She handed me a tube of sparkling pink, extended to it's fullest height. My fingers slowly wrapped around the the unaccustomed object. Then she handed me a compact with the mirror open. Both my sissy hands now held items I was totally unfamiliar with. But I had seen Mistress applying her lipstick hundreds of times. I ran a flashback of Her Highness seductively painting her beautiful lips through my little Sissy brain as fast as possible. I brought the mirror up in front of my face and saw there in the mirror a humiliating crown of prickly rollers positioned over the bland unmade-up face of a useless, clueless man. Then I slowly brought the shimmering tube closer and closer to my trembling lips. The intent group of real women and girls started to clap rhythmically, louder and louder, as I carefully brought the creamy silken confection to a point hovering just under my top lip. The chant became GO GO GO and I went went went. The lipstick came in contact with my virgin lips and I has gone. I had never felt like that before. Pink electricity surged thru me. Cream piled upon cream as my lips plumped up with the mass of BubbleGum Pink lipstick I was reveling in. As the color left the tube, millimeter by millimeter, my lips were transformed into the vision of Sissyhood I had always stored in the back of my brain, waiting for this miraculous tube to release my sissy completion. The compact mirror held delights for me to behold. At that precise time I was finally free to be the Sissy I wanted to be. Elizabeth Taylor had never done a better job on her lips than I did on mine. The women and girls cheered! Even though I was nothing but a Sissy, I had passed a test that few men would ever try, let alone succeed at. I had performed, and performed well, a truly womanly act. An act, which even though I was just a Sissy, they acknowledged as a first significant step for a Sissy into their Sisterhood. Each woman there with me in the lipstick aisle, came up one by one and pressed their hands on the rollers on the sides of my head (I was, after all, a Sissy and I had to accept pain from all women, not just my Mistress) and gave me air kisses. So far this Sissy stuff isn't as bad as I thought it might me. You just have to be the right kind of Sissy. I still had the rest of my pansy list to go. Tampons couldn't be anymore embarrassing that lipstick, could they?

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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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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...

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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