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Teaching the Sissy Maid Workshop at the MVP Chapter Five Day One of the Sissy Maid Workshop Comes to an End

Teaching the Sissy Maid Workshop at the MVP, Chapter Five: Day One of the Sissy Maid Workshop Comes to an End After lunch the ladies and their sissy candidates assemble in break-out groups where the candidates are stripped, shaved and locked in chastity as each of the pathetic males experiences new levels of shame and humiliation as they are displayed publicly and most for the first time. As the sissy graduates helped herd the male candidates into the appropriate classroom I...

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

The Reawakening of Sissy Jackson

The Reawakening of Sissy Jackson By Cassandra Morgan The memories came at night, when his consciousness was not on guard to stop them. A little boy, rushing across the playground to his mother. She laughs and picked him up, kisses him on his lips. He is a small boy, frail, too weak to play ball sports with the other kids. He plays on the swings...but not too high. He plays hopscotch. He plays jump rope. The mommy does not care. She likes having her little boy close to him, and if...

Andrew The Unsuspecting Sissy Part VII

ANDREW THE UNSUSPECTING SISSY PART VII [email protected] *** A NOTE TO ANDREWS' FANS: I DON'T GET VERY MUCH FEEDBACK, PERHAPS 4 OR 5 PEOPLE WITH EACH CHAPTER. WHILE I APPRECIATE THE SUPPORT FROM THOSE THAT ENJOY THE STORY, I CAN'T SEE CONTINUING THE TALE IF SEEMINGLY VERY FEW PEOPLE ARE INTERESTED. SO, IF YOU ENJOY THE STORY, OR DON'T, PLEASE LET ME KNOW! MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN...

Maid to Measure or Sissy Slave by Deesign Part 3

With Kind Proofing by Vickie Tern Maid to Measure, or Sissy Slave by Design, Part 3 By Mistress Kathrine The morning after Kathrine let Nikki sleep in the Master bedroom with her, she lay thinking about the things she still needed to train her pretty Sissy. Sissy Nikki didn't know anything about Kathrine's plans to marry her, and have a child with her, not yet. She decided it was time to wake her Sissy and get at least the wedding...

We got us some sort of sissy fag here

Check Your Taillights It all started pretty innocently, at least by my standards. For many years I have been a closet crossdresser and like most, I thought there must be something wrong with me. The usual bag of emotions and guilt. One day I did an online search to see if there was a forum for crossdressers and sure enough there was. My whole world changed. Not drastically but change it did. I found there were many others who felt and dressed as I did and I finally found out I...

Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

Submissive Sissy Slut Training

One time I got her to fuck me in my ass with a strap-on and I LOVED it! I moaned like a bitch in heat. She finally left me and told me that she thought I was gay and she couldn’t stay with a “man” like that. This caused something to snap in my mind. That has been 11 years ago now. I have never gotten into another relationship with a woman since. I have done a lot of jacking off, (almost every night), over the last 11 years and I have fucked my ass with a dildo a few times since then, after...

My CD Sissy story and 1st meet humiliation

I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very...

I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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....

Celia s journey to sissy slave

My first time with a guy, orally was a bit different than what usually happens with young teenage boys and their sexual experimentation, but not as much as it might seem. Growing up, next door to me was a pair of sisters, the youngest was 3 years older than me, which during this time in the story, I was 14 and she was 17 and her sister was 19. One summer day, we lost power in the neighborhood cause of a bad train wreck. Well, the sister's, their names were Cathy was the younger one and...

The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

Teaching the Sissy Maid Workshop at the MVP Chapter Four Daisy Training Prepares Her for the Workshop

Teaching the Sissy Maid Workshop at the MVP, Chapter Four: Daisy Training Prepares Her for the Workshop Synopsis: Flashing between Daisy's training before the seminar and the seminar's beginning, more is learned about how Daisy trained to be ready as Ms. Rebecca's sissy maid example and how the Sissy Maid Workshop is run to insure the transformation of the submissive male candidates into the sissy maids and cuckolds wanted by their owners. I loved the look on Daisy's face as...

Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

Punishment for a Sissy VII

Punishment for a Sissy VII By PJD Joan Cartwright glared at the broken sobbing sissy standing in front of her. As he cringed beneath her severe contemptuous gaze she thought, 'You don't understand the true reason why I intend to reduce you to a spineless snivelling sissy do you? No, you believe its because Wanda and I discovered you wearing her underwear If that were the true reason sissy. Wanda and I would have simply have paraded you in front of our friends, with a notice...

My sisters their friends and me their sissy Part 2

Part Four Jolt after jolt of electricity passed through my body. Each longer and worse than the one before it. I held my number two hole shut because I believed what Joy had said about losing any of the water. But the pain was becoming almost too much. I knew that in another jolt or two my control would be completely gone and even with the help of the big thing back there plugging me I was certain to lose that water. And there were two gallons in me making me look really pregnant....

Mommy s Dirty Sissy Slut part 1

Mommy's Dirty Sissy Slut part 1 by dirteesissy "Answer the door for me, Brother Dearest and make sure to greet my guests Properly!" I headed to the front door, shame filling my heart, as I tottered on 5" stiletto heels. Not the usual footwear for a 20 year old man, but I couldn't have looked less like a male dressed as I was. Chapter 1. Last week my sister, Alicia, caught me masturbating to stories on a website called Fictionmania. In most cases this would have been...

What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

I Want To Be A Sissy Part 3

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...

My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

Forever Her Sissy Chapter 3

Forever Her Sissy - Chapter 3 This is a work of fiction for your enjoyment, 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. We were driving west, the sun was shining and the morning was warm without being hot. Although it was a...

A Sissy Fantasy A Day And Night With Daddy

A Sissy Fantasy - A Day And Night With Daddy Daddy's Cocksucking Princess I awoke after falling asleep after last night's escapades, and the first thing I I notice is the chastitiy, it immediately reminds me of what happened last night. I wasnt expecting to be put in chasitity last night, Daddy had hinted at it, but I did not think he was have me in it so soon. I did not really want to have my clitty locked up like that, but I really want to please Daddy, so of...

Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

Andrew The Unsuspecting Sissy Part II

ANDREW THE UNSPUSPECTING SISSY PART II ANDREW'S SISSY EDUCATION BEGINS............ [email protected] Mother and daughter chatted while they ate their breakfast. Several sissies flitted about changing flowers and removing dirty dishes. "Mother," said Sarah. "How many sissies call the Manor their home these days?" "Hmmm," said Audrey as she placed her coffee cup in its saucer. I'd have to say with the school, the modeling agency, the internet dormitory, the domestic...

A sissy called Jezebel Part IV

Part IV - Jezebel's has been sent to the Head Mistress's office of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. Jezebel is inspected by the fabulously wealthy Matriarch of the Beauregard family for the milking ceremony later that night. The Beauregards and McCarthurs have been feuding for decades, but is there more to the story? (Author's Note: I had no intention of writing with such 'world building' detail when I started on this...

Becoming a Sissy Part 8

Tom makes a decision. It lists Mandy's help. And Sissy proves herself.Tom had already made his decision concerning Peter. He had thoroughly enjoyed his role-play with Mandy, but knew that having his best friend as his sissy would be even better. He trusted that what Peter wanted was to service his Daddy, and he knew from the way Peter (Sissy from now on) had serviced him on that evening, that he would do anything for his Daddy.He too had explored X hamster and was aware of the degree of...

Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

Young Sissy Ch 01

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.*I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck with needles,...

The Young Sissy Chapter 1

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. Chapter 1 I don't know how long I was under...days, weeks...who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and...

The Sissy Circus

Come One, Come Al, and visit the Sissy Circus "Welcome, Welcome, Welcome to the Zerchnod City Fair" The Barker bellowed. "Enjoy the Rides, Attractions, and State Pavilions." He continued "However, Friends, your Fair experience is not complete without visiting the "Sissy Circus" guaranteed you have never seen a more pathetic spectacle of sissyness. Enter my Friends and witness the "sissy Circus!!" The Barker pleasantly saw several dozen pay to enter the pink and white tent to await the...

sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

I Want To Be A Sissy Part 4

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...

My Sissy Submission Hell

I was just lying there on satin sheets, wrapped in beautiful lingerie, and...Well, let me start at the beginning, so you know what's going on, okay? I have always been straight, even though I had never had too much luck with the women. I have dated several young ladies, but not with the sort of regularity that I wished for. Never the less, I never, ever thought about men in anything close to a sexual way. At least until last year, that is. Allow me to tell you about myself: I'm...

Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

Sissy Farm Chapter Twenty One

Sissy Farm - Chapter Twenty One - 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; 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...

Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

My Sissy Rules

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it.I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for the rare occasions when I am rented out to others. This is my sissy life, and it makes me happy.Sissy's Training Rules- Sissy must wear...

Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

Neighbourhood Terror to Sissy pt 15

(If you like this story and want to read ahead of what's available so far, please consider following me on Patreon it's already on part 17. My Patreon also has A holiday special for Halloween up which also deals with a feminisation theme, revenge and a trans girl. It's a bit of a darker story, but it's for Halloween after all. There is also a first part of a story written for one of my Patreons as a tier reward online. Last but not least a commissioned drawing based on this part will go...

Andrew The Unsuspecting Sissy Part V

ANDREW THE UNSUSPECTING SISSY PART V [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM BRECKMAN: BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

What Kinda of sissy are your

Was written by othersStories Have sissy thoughts? Pt.1: What you need to know. If you are wondering whether being a sissy is for you, the following information will point out the many good things, and dispel any doubts or negative feelings you may have about becoming a sissy gurl. The rules are important, and obeying the rules will make you a happier sissy.Repeated reading of this and the subsequent entries will deepen and clarify your sissy state of mind: once you have freed yourself from...

Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

The Sissy Factory 2 Prep for School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

Trucker Daddy gets himself a New Sissy part 1 and 2

TRUCKER DADDY GETS HIMSELF A SISSY BY DEEWET It could easily be the lowest point in Denny's life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truck Stop. He almost jumped out of his skin when someone knocked on the window. Denny...

Rubber Sissy Panties Part 2

Rubber Sissy Panties Part II Clark woke up at work. He was dressed in the same clothes as in the previous day, shaven and the clothes were clean and ironed to perfection. He looked at the clock on his computer, and it was 7am, way earlier than anyone else would be hanging around. He raised himself off his chair and walked to the W/C, ready to relieve his full bladder. Not noticing his own behavior, he lowers his pants and sits down on the toilet, and points his sissy clitty...

Punishment for a Sissy III

Punishment for a Sissy III By PJD Mrs. Cartwright arrived at her mansion, the whimpering sissy trapped inside the dog cage saw the large iron gates open automatically. She hadn't spoken one word to the sissy in the entire journey from Wand's, the sissy looking through the rear window at the long winding drive, wondered what this silent dominant woman had planned for his future. As the car drove up to mansion four ladies appeared and strode towards the car. The sissy shook...

Have sissy thoughts Pt 1 What you need to know

If you are wondering whether being a sissy is for you, the following information will point out the many good things, and dispel any doubts or negative feelings you may have about becoming a sissy gurl. The rules are important, and obeying the rules will make you a happier sissy.Repeated reading of this and the subsequent entries will deepen and clarify your sissy state of mind: once you have freed yourself from thoughts of masculinity, you will be left with only the desire to please real men,...

Neighbourhood Terror to Sissy pt 13

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrupted by Linda, knowing the shop owner from his past experiences here. There was nothing he could do about it either. He couldn't...

Mistress Sarah makes Evie a Sissy 2

"Look at you Evie. You're so slutty in your teddy and stockings,” said Mistress Sarah. Then she looked down at my hard cock and said, "....and your clitty is so big. Excited are, you?" Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see that arse of yours." Ever since I had met Mistress Sarah online, I had dreamed of her fucking me in the arse....

Crossdressing

Pimped out Sissy Finale

The next text I received to worship Mistress Samantha came an agonizing month later. Once again it was short and to the point. I had to be at her place early in the morning, but this time along with my maids dress I had to bring something slutty. I had just bought a new purple PVC mini dress that I was eager to try on so I packed that and having made excuses to my wife left early for a day of servitude....and lots of pussy licking I hoped. I spent the day dressed as a maid...

Young Sissy Ch 02

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of rolling hills...there wasn't a soul in sight...and yet, for some reason, I didn't feel frightened or lonely like I usually do by myself. It was...

The Young Sissy Chapter 2

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of rolling hills...there wasn't a soul in sight...and yet, for some reason, I didn't feel frightened or lonely like I usually do by myself....

The Sissy Diaries 2 My Total Transformation

Dear Diary, Ever since Mistress Alexa and Mistress Kerri took control of my life, it has become both a wonderful sissy dream and a horrible sissy nightmare all at the same time. Initially, mostly the latter, as the first few weeks were probably the hardest. Oh diary, it's like when I was living at home under the control of my evil mother and two older evil sisters. Except not only am I dressed 24/7 in girly dresses and as a sissy maid too, but I'm being used like a sissy slut, and...

Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

Becoming a Sissy Part 10

Apologies for the delay. This is the final part of "becoming a sissy". Obviously, I have packed a lot more into this story, and I apologise if it got complicated with too many characters. I'm thinking of writing another story which will take up from where we are now, but I will make it more focused on one or two characters. It's my first story, so I guess lessons.Over the next five days a plan formulated in Tom's mind. As he thought about it he would have three submissive sluts vying for his...

SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

Owned sissy girl of dom couple Part 1

I met the mature dominant couple that I now call Mummy & Daddy on the internet. I am a 52 year old sissy who loves to be dominated, feminised and made to be a humiliated mincing sissy slut.Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for two weeks prior to my arrival - a daunting task to say the least...They answered the...

Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

The Sissy Girly Game

The Sissy-Girly Game by SissyKimmy1 Chapter 1 - Let's Play Ballerina I couldn't believe this was happening to me. I was still in shock. It was all my little sister's fault. She was always a little bitch but now she had ruined my life completely. I never thought she would take it this far. I couldn't believe she wouldn't come clean and tell our parents the truth. She was following behind me snickering as we approached my new home. My father rang the doorbell. "Dad! You...

Neighbourhood Terror to Sissy pt 7

Chapter 7 Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well at least it was his own cum. "So, I believe with this I have answered all your answers regarding your chastity cage....

Young Sissy Ch 03

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pure satisfaction of hot flesh filling my pussy. It made me feel...whole. Of course, it also pushed down my cum button and sent my body into...

Becoming A Sissy Slut part 2

I awoke Sunday morning alone in Kassy’s bed, still in the tight mini skirt, my ass was deliciously sore bringing back a flood of memories from last night. I had spent the evening in full drag dressed as a slut and serving my mistress’s rubber cock followed by swallowing my own cum. It was hands down the best night of my life, I had never came so hard, and the rush I felt while serving her was a high that I’d never known. I rolled out of bed and stood up, my wig had fallen off in the night...

Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

Lockdown Sissy part 1

Author's Note: Thanks to those who have reached out to me with story ideas. It's been difficult to get any writing done these past few months, but hopefully my head is finally back in writing mode. I hope you enjoy this nasty little fantasy. Please let me know if you have any thoughts or ideas--either here in the comments or directly at [email protected] xoxox Emshoninque Lockdown Sissy- part 1 I made a resolution to become a better sissy in 2020. It's something that has...

Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

Andrew The Unsuspecting Sissy Part IV

ANDREW THE UNSUSPECTING SISSY PART IV [email protected] MAY I SUGGEST THAT YOU READ THE EARLIER CHAPTERS OF ANDREW SO THAT YOU MAY UNDERSTAND WHAT THE POOR DEAR HAS BEEN THROUGH THUS FAR..... ANDREW NOW DREW: SISSY SUPERSTAR, SOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIALIST, WITH A PENCHANT FOR SISSIES AUDREY: DREW'S STEPMOTHER AND OWNER OF THE MANOR SARAH: DREW'S STEPSISTER AND TRAINER VALERIE: DREW'S DOCENT TRAINER DR ALICIA NEWMAN: MEDICAL DIRECTOR OF THE...

A sissy called Jezebel Part VII

A sissy called Jezebel Part VII - Jezebel has finished hir tour with the Head Mistress into the secretive dungeon/reform school below the fair walls of the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. But is the Head Mistress entirely done with Jezebel? Additionally, what ever does one learn in a 'sissy life skills' class? I require the gurls in my harem to crawl on the floor at home and in private at the office. So get on...

Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. 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 Three - Birth of a...

Sissy s She Cock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

Owned mature sissy girl

I met the mature dominant couple that I now call Mummy & Daddy even though I am 54 years old, on the internet. Their ad said they were looking for a full-time live-in mature sissy plaything. After we made contact they invited me to their house. I was instructed to bring any sissy clothes with me and to refrain from orgasm for two weeks prior to my arrival - a daunting task to say the least...They answered the door together - he was a tall very masculine mature man in a suit, his trousers...

Punishment for a Sissy VI

Punishment for a Sissy VI By PJD Miss Jones, on hearing Mrs. Cartwright command to enter, opened the study door. And led the naked, hairless, chained sissy into the room, followed by the servants. The two young maids following Panties into study, smiled at each other anticipating further punishment for the sissy, their tiny nylon panties already damp at the sissy's humiliation. "Bring her into centre of the room Miss Joans." commanded Mrs. Cartwright. The sissy was led into...

Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest

Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

My Uncle Wally s Sissy Boy Wife

Penned by: Miss Deborah (Debi) Leigh JohnsonOneI did not know what I could expect, as the Greyhound pulled into thebus station. I did not know a whole lot in fact, as I was a rebelliousknow it all, fifteen year old brat.My parents were pretty good as far as parents went. I had not locked aroof over my head, or enough food on the table, but I had alwaysresented the fact that my parents were not rich enough to give meeverything that I wanted. I knew in the back of my mind that this wasa pretty...

Paul the Sissy Cuckold

Paul the Sissy Cuckold Part One Sue sat at her kitchen table chatting with her friend Debbie while at the sink her husband, Paul, worked to clean the dishes from dinner. Sue and Debbie laughed and talked about how nice it was to be relieved of the burden of housework now that Paul had lost his job and was free to take care of the household chores. The two women sipped coffee and discussed the freedom this allowed Sue to go out at night with friends and enjoy herself. Money had never...

Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

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,...

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