I Want To Be A Sissy - Part 4 free porn video

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After my intense and strangely satisfying lipstick application initiation, all the women and young girls and the male pharmacist drifted off, allowing Judy to take control of her cute little pansy customer once again. I was dumbfounded that the woman I first saw coming towards me with what I thought was disgust in her eyes, was really a rougher, blunted extension of my darling wife, my Mistress Claire. Judy seemed perfectly happy to take command of me and my sissy needs. She proved herself nonjudgmental in my quest for the perfect sissy lipsticks but she was also stern with me in keeping me in my place, lower that even men in her female faultless estimation. It was like Mistress Claire had sent a guardian angel to watch, fondly and dispassionately, over her budding sissy property. Now that sniveling property had to get back to the task at hand, my humiliation and sissification. Judy was willing and able to drag me down that girlish path with me screaming like a girl. "OK, Sissy Wendy, you look a lot more comfortable now with your lips painted BubbleGum Pink. Isn't it amazing how just a little lipstick can make a girl or a sissy more at home with yourself? I know that when you came in the door, prancing and mincing and patting those relentless curlers, you were shaking in your little kitten heels. I bet you thought I was going to throw you out of this feminine domain. No, Sissy, I don't want to throw you out. I want to take you further on your journey. Now that BubbleGum Pink lipstick has given you a little more confidence, what is next on that mysterious list you mentioned?" "Mistress desires that I should buy a Home Permanent kit. I was to ask the sales girl which kit gives the strongest and tightest curl. And also for extra end papers and extra rods. She said you will know what she means. I surely don't." "We can take care of that item for you right over here in the hair beauty products aisle. Extra end papers and extra rods mean that your Mistress has a very intense perm in mind for you. Oh, my goodness, a man's first real woman's perm can be a terrifying experience. My husband can testify to that fact. Today I have to fight off his requests for more and more frequent perms. But his first perm, that was a different story. I had to tie him into our home salon's styling chair. Oh, he was screaming and fidgeting. He was not going to have his manly hair curled like some tartish bimbo. Oh NO! Each perm rod brought curses and threats. But each perm rod also brought him closer to my total subjugation. By the time he was totally rolled and netted and under the dryer, his wails had subsided to slow hot tears. He was so cute in his perm rods under that dryer that because I was so proud of him I just had to take pictures and post them on Facebook. Those pictures were a big hit at the bowling alley on league night. I assume that such will be your lot, too. So let's get the Perm Kit of your dreams. The faster we have the kit, the sooner you can be under the dryer like any effeminate sissy." I loved the story of Judy's husband. I wasn't the only man controlled by women to the point of lipstick and perms. That thought gave me some confidence that I could reach my hidden desire to be a Sissy. Not that it wouldn't be painful and humiliating but I now knew that I wasn't alone in my unmanly need to stop being a man and to become a hybrid, asexual, painted strumpet with a useless male hangydownthingy. "Here we are, Darling! I bet you didn't know there were so many different kinds and brands of Home Perms? I have always had the best luck with Lilt. That is what my mother used on me and my brothers when we were young. Though nothing can beat a salon perm, it is still a joy to sit at the kitchen table, your Lilt chemically curling your hair as you sit under a big pink bonnet dryer. Mother would do my nails as I sat there. My favorite part of home perming was when it was my brother's turn for their perms. Mother would be so proud of her young men, neatly rolled and doing each other's nails, while they took turns under the dryer. That was when they were in their teens. Now one is a Minister and the other is a Psychiatrist. They still come to me to purchase their home perms. Their wives do a fabulous job in maintaining their femininity. But I do think that they visit the salon more often now than doing the home version. "I use the Lilt Body Wave kit on my husband. I am not into having him in curls all the time but he and I both enjoy the actual process of perming more than the curls. But for you, dear Sissy, I think your Mistress would want you to purchase the Lilt Heavenly Curl Perm. If you will excuse the pun: this is no perm for a sissy! Shirley Temple would die for these curls. But I believe you mentioned your Mistress' goal was Doris Day? Can you imagine how many perms Miss Day had in her life? Well, I bet the same will be true for you, Sissy. "OK, that's another item off your Sissy Bucket List. Maybe I could come help Mistress do your perm. I would enjoy that." "Of course you may come! I am sure Mistress would appreciate all the help you could give. Buy I don't think you will have to worry about tying me to the chair like you did your husband the first time. Though that option does have its' "virtues". As a Sissy, I naturally enjoy all things involving being tied up." "What feminine delight is next on your list?" I blushed. This was the biggy. The sissy absolute must have that I dreaded contemplating the most. I lowered my eyes and a small sound came out of my newly lipsticked mouth: "I need Tampons and MaxiPads for my period." "Well, dear boy, of course you do. We all do. Even my husband has his grumpy time. But stick a Super Absorbent Tampon up there, nice and tight, and he is in pansy heaven. No need to be embarrassed by your curse. Tampons can be fun." "How strong are your periods, darling?" "Mistress says I am going into the late teen girlish gushing time. Light cramping and bloating but large discharge. It was so embarrassing the first time, just last week. Mistress didn't have the proper tampons available for a bloody sissy like me, so that is why Tampons are on the list. Can't afford to ruin any more virginal white panties." "Well, then, let's set you up with some Tanpax Super Absorbent Pearl Plastic applicator tampons. They have the new plastic applicator which is so much easier to insert, especially for a Sissy. The tampon enlarges and molds to your personal vaginal needs and seals against any unsightly drip. "Again, i think back to my brothers and to my husband. Strangely they didn't enjoy tampon training. At least at first. The first time with my husband was quiet stressful. The silly cow fought me. It made the whole insertion training process a disaster. HE thought he could get away with just maxi pads. Silly cunt! I knew what he needed. Just what you are going to get. A real woman's tampon pushed into your sissy vagina by first, your Mistress, and then by yourself. I know my brothers came to love the security and the fullness of their tampons. Soon my husband realized the benefits of proper female hygiene. It took several thorough cleansing enemas to establish his place in the female scheme of things but now he likes nothing better than to discuss the relative merits of douching vs. bidet usage. "Again, just like with the Perm, I would love to help your Mistress in your Female Personal Hygiene training. I have't lost a brother or a husband yet. Maybe Mistress will give you a "First Insertion Party". They are always a fun time, at least for the guests. You would be surprised how many grown men faint at a little ole tampon being shoved up their sissy vagina. And I am sure your Mistress knows that used sissy tampons or real used female tampons make wonderful attitude adjusters. You may find that a used soggy tampon inserted into your sissy mouth, and then having the mouth duck taped shut, will make a completely docile little pussy cat out of the most belligerent used to be male." I envisioned such an insertion party for me. Maybe I would faint. But my fainting would just make it that much easier to insert the tampon in me. But I wouldn't have the powerful experience of a real woman violating my personally private orifice. Doing it yourself is, like applying lipstick for the first time, a life changing rite. But having a woman do it, roughly or lovingly, is a statement of your servitude and your acceptance of sissy discipline. But after hearing Judy's stories about her brothers and husband, I am ready to accept my period and my need for a tampon. I will be honored to have a tampon inserted by my Mistress and by Judy. Again I don't want to ruin anymore panties. "Now what is the next item of sissydom you have to purchase?" "Mistress wishes that I purchase a pair of very feminine sunglasses to frame my sparkling eyes under my crown of curlers." "I think I see you as a Sissy who would choose white frames with a gold chain hanging around your slender next , ala Audrey Hepburn. We have just the thing here in the women's sunglass dept. Here, love, try these puppies on." I stood, transfixed, lipsticked, and confused, before the mirror, which was outlined with brilliant makeup lights. The sunglasses slid over my ears, under the curlers, nestling on my little girl pug nose. The gold chain hung like a necklace across the back of my blushing slender sissy neck. The pink of my lipstick and the glowing white of the glasses and the harsh silver steel of the ever present curlers created, unlikely or not, a most unusually feminine countenence. These were not my father's aviators. "Oh, Judy, thank you so much, these glasses are divine. Mistress will surely approve." Judy turned to some of the women customers who were near. "Girls! Look how darling our little Sissy is in her new girlish sunglasses!" I turned toward my audience and did a little curtsey and gave a girlish peek over the top of the glasses. There was a polite smattering of applause from the ladies, even some of the older women who were initially so judgmental of a sissy such as I. In my first partial day as a full blown sissy, I am starting to realize that a sissy can be accepted, or tolerated, by real women, if the sissy is respectful of the glorious femininity which is being bestowed upon him, like a bounteous gift from She Who Must Be Obeyed. They may find you queer or less than human, but they will respect you for following their demanding rules and mysterious rites. My Mistress, my wife, may be entitled to be severe and harsh with her abject sissy, but the rest of the female world can be your GG friend if you are properly in your place and willing to learn and obey all that the female of the species deems important for a lesser creature, like a sniveling sissy. "Is there anything else on your grocery list of starter sissiness?" "Just various types of hosiery. Mistress must want me to be ready for whatever the dressing situation may require. Control Top Pantyhose, Knee Hi's, Thigh Hi's, Dress Hose, I will be ready for any skirt length or no skirt at all." "My husband adores Control Top Panty Hose. He surely needs the control, very firm. My Lord, he was resistant at first. The little wimp! But a week in Panty Hose made him beg me to be allowed to wear them continuously. They do make his shaven legs look quite womanly. He really has become quite a sissy. But I love him. "Let's get you taken care of with your hosiery purchases. Should be no problem. You are not much in the way of a man so I don't think we will even have to consider Queen sizes. My cart filled with little egg shaped containers and sleek flat packages of sheer nylon torture for a male sissy. I envisioned a month to come, never exposing by spindly bare legs to the sun. I was to be the ultimate Pantywaisted, nylon clad, sissy male. "Anything else, Sissy Wendy? I have real women customers who should be serviced. My pity and fascination for your quivering self has just about evaporated." "The last item on my list is an item which must be of my own choosing, but still very feminine." "Hmmmm, Mistress has given you a choice. Very unusual! She must love you very much. "How about more makeup? " I am sure Mistress has all that I will be needing. The lipsticks today were a test of my willing obedience and my sissy need of humiliation." "How about a Salon Hair Dryer?" "Been there, done that." "Really, Judy, I was thinking about more intense Female Hygiene. Possibly enema related or Douching related. I am sure Mistress will love my concern that her Sissy be exceptionally clean for her uses and desires." "We have just the thing for a sissy like you. We sell a lot of these kits to mothers who want to train their daughters, or sons, in correct and thorough Feminine Hygiene. It contains a complete medical grade enema kit. That terrifies the teenage sons a lot. Those nozzles and bulbs and bags can be quite frightening to tender teenage male initiates. The kit also contains several types of Douches. Harsh medical douches and sweet smelling everyday douches. I am sure a douche will become part of your daily regimen of female hygiene. It is really quite soothing and adds a nice crispness to your vaginal parts, each and every morning when you douche. Your Sissy brain will be in heaven, knowing that your sweet smelling sissy vagina will not offend any real woman. It's 6:15 AM each morning for my husband, just as it was for myself and my brothers when we were growing up." "Sounds marvelous! I am sure Mistress Claire will surely approve of this choice by her Sissy husband. I will take it! Now I have finished my sissy list. That's a load off my little girly mind! "Thank you, Judy, for being so nice to a sissy such as I." "I enjoyed doing my job, sissy or real woman. Remember, Sissy Wendy, that even though real women may be nice to you, they still know what you are and they are laughing at you all the time. Just as I am now. Go, Sissy Wendy, as you came in, walking in the Sissy Way so that all who see you will know what you are and wonder how you became such a disgusting Sissy Nancy Boy. "Now, Girls, look at our Sissy! Be thankful that you are women! How dreadful to know that a creature could go through life being an pitiful, humiliated object such as Wendy Sissy! "Now, get out of this place so real women can get back to their business of being beautiful. Put your chest out, head and eyes down, elbows close into your sides, purse hung from your shoulder, wrists up to breast level (you will have large breasts shortly), wrists limp, fingers wiggling, short mincing steps, sway your girlish hips and be on your sissy way, back to your Goddess Who Must Be Obeyed! PAT YOUR CURLERS! And that is what I did!

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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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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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