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Sissy Stepson 10 Stepmother s Sissy

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

Motherless Incest

Incest porn has been a staple of pornography since the very first incel caveman realized that he couldn’t find fresh pussy out and about. He resorted to sniffing a whiff of his mother’s loincloth when she wasn’t looking, and beating his old cave meat into a leather sock.Now personally I’m not into the whole mommy-son dynamic – I’m a classy guy. But it’s no secret people like to get freaky when the lights go out, and if you’ve got a stiffy in your hand and you’re on Motherless, you gotta go...

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Sissy Stepson Part 4 Stepmother s Test

Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...

Dominatrix Hunting

Dominatrix Hunting By SevikaaIt was way, way too early to be dealing with stuff this weird...I was a fresh-out-of-Police-Academy officer working with the San Francisco Police Department, based out of Inglewood Station and with the misfortune to have to punch in at six in the morning. I was literally two minutes into my shift – not even long enough to make a cup of instant coffee – when I heard something of a commotion down the hall, a handful of my colleagues craning their necks to get a look....

My Stepmothers Sissy Daughter

My Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...

The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

The Passage of Chastity

The carriage jounced along the road carrying a young woman. She looked out the window and saw in the distance a great building. "Is that it?" she shouted up at the driver. "Yes, miss. That's it, Milford Hall." The girl gazed at the edifice. Three stories of red brick with oriental domes and heavy chimneys, the building had been built in the Elizabethan period. It was U shaped, with two massive wings extending behind. It looked frightening to her. The young girl settled back, nervous now...

Woman rsquo s Guide to a Fun and Exciting Male Chastity

Nine times out of ten, or maybe 99 times out of 100, it is the man who brings up the idea of male chastity and his fantasy of being denied.The woman’s reaction will vary…. from complete disgust…. to obvious disinterest…. maybe mild curiosity…. all the way to emphatic embracement.No wonder it can be nerve wracking for a guy to broach the subject of malechastity to his partner.Her reaction will make or break his day!Keep in mind that he would not have brought it up if it wasn’t important to him,...

Incestuous Harem s Passion 13 Teaching Incest to the Siblings

(An Incestuous Harem Story) Chapter Fourteen: Teaching Incest to the Siblings By mypenname3000 Copyright 2019 Note: Thanks to wrc264 for beta reading this! April 10th, 2027 – Catherine Nicholson My nerves had me trembling. Today was my first undercover assignment as a cop. I never thought it would be with my brother. But that was what made us perfect for this assignment. My hands smoothed down the skirt of the sundress. It seemed the perfect thing to wear. It was a nice Sunday afternoon....

Nate s Chastity

After a little encouragement, Nate's soon to be wife, Sophie, agreed to be his key holder on the condition that it would be on her terms - 'well fine, that's kind of the point' he thought. However, he did not anticipate how extreme she'd take things. Day 0, the day Nate first put on a chastity device: This evening (Friday: Day 0) was scheduled to be Nate's first time ever in chastity, something he'd waited a long time for. Sophie had ordered the chastity device she wanted him to wear...

Introduction to Chastity

Introduction to ChastityCarla and I had been dating for about three months. She was unlike anyother girl I had ever known. Where most girls are rather passive andsubmissive around men, Carla was just the opposite. She wanted to be incontrol of things. She was aggressive and dominant, and she insisted Iassume the opposite role. At first I was resistant, thinking somehow mymale pride was at stake, but the sex with her was so good that Isuppressed my normal male instincts and went along with...

Introduction to Chastity

Introduction to Chastity Carla and I had been dating for about three months. She was unlike any other girl I had ever known. Where most girls are rather passive and submissive around men, Carla was just the opposite. She wanted to be in control of things. She was aggressive and dominant, and she insisted I assume the opposite role. At first I was resistant, thinking somehow my male pride was at stake, but the sex with her was so good that I suppressed my normal male instincts and...

College Celebrations Chastity

“Double booked” said Chastity…. and for such tricky political double-speaker fuckers, they were unsure in the presence of sassy seeping sexuality. It only took one finger curling through her hair, two eyes flirting and three zips down and...Chastity was enjoying a puff on one of Bernard’s fags she had nicked recently. She was in the dorm ablutions, no smoke detectors. It was early, no one else was up. She needed a calming fag before her big day began. Multiple Awards to collect in the morning...

Step mother s Sissy School boy

One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

Chastity

On the day of Chastity’s birthday she snuck out of the house just before dawn to ride her horse Winchester. She put his bridle on and took off. She needed to clear her head and figure out what to do next. For she knew her parents were going to choose a man for her to marry. Riding Winchester always made her feel better, the wind through her hair always made her nipples hard; And the gentle rubbing of her clit on the bare back of a horse always made her forget for a bit, who she was and what was...

Chastity

If you are not of a proper age, don't read this. Keywords Use of Sex Toys High Heels Chastity Belt Categories Bondage Femdom Synopsis Jay and Janet were happily married until Jay.... Chastity By Janet Baker I'm twenty five, so is my husband. We met in college, married after graduation. I started to work, my husband Jay went on for his Phd in software operating system design subsequently starting to work in a neighboring city. His credentials and his...

Chastity

Keywords Use of Sex Toys High Heels Chastity BeltCategories Bondage FemdomSynopsis Jay and Janet were happily married until Jay?. Chastity By Janet BakerI?m twenty five, so is my husband. We met in college, married after graduation. I started to work, my husband Jay went on for his Phd in software operating system design subsequently starting to work in a neighboring city. His credentials and his drive moved him up in salary and gained the...

CUCK HUBBY IN CHASTITY

CUCK HUBBY IN CHASTITY Being locked in chastity can do plenty to a man. The longer he can't getfree, the bigger the changes. "What do you think of these?" Bella wanted to know. "They're called DatePanties. 'Cheeky' style. Because they leave my butt cheeks showing." The curvaceous woman turned around so her husband could see the rearview. He opened and shut his mouth, throat so dry he couldn't speak. Shewas extremely sexy, with her long red-brown hair, generous bust, fullhips, and gorgeously...

CUCK HUBBY IN CHASTITY

CUCK HUBBY IN CHASTITYBeing locked in chastity can do plenty to a man. The longer he can't getfree, the bigger the changes. "What do you think of these?" Bella wanted to know. "They're called DatePanties. 'Cheeky' style. Because they leave my butt cheeks showing." The curvaceous woman turned around so her husband could see the rearview. He opened and shut his mouth, throat so dry he couldn't speak. Shewas extremely sexy, with her long red-brown hair, generous bust, fullhips, and gorgeously...

Cuck Hubby In Chastity

CUCK HUBBY IN CHASTITY by Throne Being locked in chastity can do plenty to a man. The longer he can't get free, the bigger the changes. "What do you think of these?" Bella wanted to know. "They're called Date Panties. 'Cheeky' style. Because they leave my butt cheeks showing." The curvaceous woman turned around so her husband could see the rear view. He opened and shut his mouth, throat so dry he couldn't speak. She was extremely sexy, with her long red-brown hair, generous bust,...

Sissy Stepson Part 1 Stepmother s Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

Sarahs chastity

I saw her face light up as she took the handcuffs from the rack and turned them over in her hand.I said, "You look like you've used those before."She smiled. "They remind me of a boyfriend I had in college. I spent quite a few hours in them then. It was fun, but that was as kinky as it got."Wow. When I invited Sarah up to see my shop, I had no idea she was into this stuff. I wanted to find out more, but I didn't want to push my luck, so I proceeded with caution. "Well look around anything else....

Incestuous Harem s Passion 4 Naughty Mommy Incest

(An Incestuous Harem Story) Chapter Four: Naughty Mommy Incest By mypenname3000 Copyright 2019 Note: Thanks to wrc264 for beta reading this! April 23rd, 2019 – Clinton “Clint” Elliston II The backyard party at the Reenburgs' home was well underway. Their large house, verging on a mansion, had an impressive yard. Lights were strung across the bushes, lighting it up as twilight fell upon the world. It was a warm, April evening, the sky clear. Like when I'd done at the Reenburgs' party...

Male Chastity

Janice and Mike are a married couple in their mid forties. Married about twenty years. About ten years ago they started playing with a male chastity device and discovered they were having a lot of fun with it. They have been using it ever since.The device is a stainless steel or plastic tube about three and a half inches long and about an inch and a half in diameter with a forty-five degree bend in the middle of it. A steel ring is attached to the tube. The flaccid penis fits into the tube and...

Ginger Duck In Chastity

GINGER DUCK IN CHASTITY by Throne I sat on a kitchen chair, shifting my feet anxiously. My wife Desiree looked at me with barely restrained impatience, like she was dealing with a difficult child. Yet her green eyes held a hint of mischief. Those pale lips suggested the beginnings of a smile. I sat there trying to appear capable of reasoning with her, but that's not easy when you're dressed in a yellow top with a ruffled front and capped sleeves, and you're naked from the waist...

Incestuous Harem s Passion 22 Questioning Incest

(An Incestuous Harem Story) Chapter Twenty-Two: Questioning Incest By mypenname3000 Copyright 2020 Note: Thanks to wrc264 for beta reading this! July 22nd, 2027 – Jaiden Walsh I lounged on the couch in the small living room of the apartment I rented with my sister. Our neighbors thought she was my wife. None of them knew our background, where we came from, or that our mother had freaked out when she'd caught Alysha and me together in bed over a year ago. The AC kept everything cool,...

Crowd Sourced Sissy Spin Off Mother s Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

Dominatrix

But her attitude. Her attitude was all from her American father. Strong willed, head strong and fiercely individualistic. She was used to getting her way, every time, all the time. She wore a pair of black leather high cut, bikini style bottoms. Her small breasts were covered with a black leather halter exposing her toned midriff. A black leather cape adorned her slim shoulders. She stepped forward towards the kneeling female figure in front of her feet. The figure's head was...

Chastity

Chastity by TheVariableXChapter 1: My lifeChapter Codes: M+/f, f-self, enema, exhibition, incest, spanking, teen, chastity belt, HighSchool, consensual, Bondage, BDSM, humiliation, Rated R, My name is Alexandra and today is my first day in the 11th grade. I am naked and wet. My small wrists are tied to the metal bed frame above my head and a homemade spreader bar above my knees forces me to keep my hairless legs spread wide open. As usual I am also wearing a simple black blindfold and my...

Mother Son Incest In Japan

Leave your comments and opinions in Hi friends funrajrathode again I hope you enjoyed my last story, you already know all my stories are fiction but now I am going to say a real incest story so tune up. It’s a real experience of my colleague (my team leader),when I joined to IT field my team leader became very close to me, now after spending one years working together I revealed myself that I am posting sex stories so he wants me to post one of his experience, he is 38 year old now the story...

Incestuous Harem s PassionChapter 14 Teaching Incest to the Siblings

April 10th, 2027 – Catherine Nicholson My nerves had me trembling. Today was my first undercover assignment as a cop. I never thought it would be with my brother. But that was what made us perfect for this assignment. My hands smoothed down the skirt of the sundress. It seemed the perfect thing to wear. It was a nice Sunday afternoon. “You can do this, Catherine,” I told myself as I stared at my reflection. I snagged my purse and marched out of my room in the house the Sacramento Police...

The Day Of Chastity

The Day of ChastityThe padded jiffy bag arrived from Australia. I took it, hands trembling, managed to sign for it and opened it, removing the contents: a small keyless lock and a note, it’s simple message ‘Tonight’.Miss Jennifer had established my inability to refrain from wanking and had decided that chastity was the only option. I’d purchased a suitable device and had been practicing with it over the last few weeks, but tonight would be different, for the little lock was one controlled by an...

Incest story of my mother

Hope you may find my absolutely real story pretty hot! My name is ganesh (name changed) and I am working in a company in Chennai and native is Madurai Our family includes 4 members… my dad and my beautiful mom who is now a sexy, lustful mom craving for sex !!Again I am saying readers… this is very much real and it’s happening!! My dad is working in a bank and my mother is a house-wife and her name is Geeta. we are from a Brahmin family. Ever since i got to know about incest, i was reading about...

Mother s Sissy Teacher s Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

Chastity

ChastityRina was disturbed. Her son Ritwik, or Rik, could it spot it a mile away as soon he came back from college and sat down on the sofa that covered half of the living room of their tiny flat in Bowbazar, a part of Calcutta that had seen better days. Normally she would have had a million questions -- what was taught today? who did what? and said what? and so on while serving him his evening tiffin. But today, after a rather hurried hello, she had quickly retired to the tiny kitchen and Rik...

Penis Shrinking from Chastity

Penis Shrinking from ChastityAfter losing my GF Eva to her lover big black cock, I was pretty depressed. I knew that my 2 inch skinny penis was not big enough to satisfy any experienced women. Sure it was fine as a teenager fucking young girls, but in my mid thirties I figured pussy for me was likely to be rare.While reading pornography on the web I discovered stories about small penis humiliation and became entranced, seeking out more and more. Eventually I encountered stories about little...

The BEST vacation ever Mother Son Incest

0The plane had just landed. Palm trees and sand was everywhere. THe captain announced the arrival at the island and it was official. They were on vacationSarah and justin had been anticipating this forever. As mother and son they went on vacation often together as Sarah was never married. The plane began taxing on the runway towards the drop off point , while Sarah and Justin just smiled at each other in happinessAs they stepped off the plane and went to luggage check, Justin couldn't help but...

Dominatrix Special Moments

Coming of Age Dominatrix Special Moments! Midnightx.com/ TJ RyderIllustrated Femdom cuckold fetish stories for Adults Only! The shapely, mid-thirties woman addressed the class of dominatrix mothers. "So when does a mother know when her daughter is ready to doa male by herself?" "Well, it's a rhetorical question actually. In a femdom majority colony like Europa, dominance over males usually beginswithin the family. And the question can also be phrased...

Dominatrix Next Door

Dominatrix Next Door! TJ Ryder http://www.midnightx.com/ chapter 1 When Billy came home from school that Friday afternoonhe saw the note on the refrigerator from his momand sighed! Oh boy! She hadn't forgotten it after all. His beautiful mother had already left as she had plannedfor a weekend workshop and she had remembered to leavea note for the various chores he was supposed to do. That wouldn't be so bad except for that one...

I m a boy in chastity

When I was just a teenager, I recall my first sexual urges and they caused me to seek out any opportunities for sex and as it turned out helping others gain sexual gratification. This led me to eventually offer my close friend a very good deal, let me explain... We had shyly played around with each other’s cocks and eventually it escalated into mutual jerk-off sessions where we would masturbate one another and enjoy the wonderful new found sensation which we both agreed was even better when...

2088 It s a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

The Sissy Master

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

Forever Her Sissy Chapter 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. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

Tweak Chapter Four What s A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

Good Sissy Girl

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...

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...

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...

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...

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...

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...

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...

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,...

4 07am 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...

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...

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...

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...

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...

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...

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."...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

Sandy s 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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

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