My Roommate New Sissy Maid free porn video

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I been living with Gina who happens to be muscular and stronger than me I haven’t paying my rent for 2 months so one day when I meet her in the living room “you been not paying for months so I have idea for you to repay me so I got this” it was a pair of pink panties heels and black stockings and a maid dress “I decided to should be my maid until you paid me” I have no choice she is more stronger than me “whatever you say” I put the outfit and a chastity cage on and when I started working she always stare at my plump ass it jiggles every time until one night would change my life.

Same as My roommate new sissy maid Videos

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Teaching The Sissy Maid Workshop At The MVG Chapter Two Jaime Learns About Life As A Sissy Maid

I led Jaime from the garage to my master bedroom in the back of the house and told him to get in the Waiting Position as he had done before and to remain silent until he was told he could talk.  I smiled when he nodded his head up and down for yes since he had just been denied the right of speech.  Perhaps he may just become as valuable as he appears on first glance, but that was rarely the case and each sissy was a reflection of the woman who transitioned him from his maleness.  He was merely...

Femdom
1 year ago
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Mistress Sandy gets a sissy maid

I had been serving Mistress Sandy for about 6 months. I felt I had progressed well and felt Mistress had also. The fantasy of being a sissy maid had been one held for over 20 years, but not until the internet came along had I ever tried to actually find a Mistress or Master. Masters came easiest, but I quickly found they all wanted a sex slave, not a maid. However one of those Masters had a friend He felt I should meet. From the start Mistress Sandy admitted She had no knowledge of...

4 years ago
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From Husband to Sissy Maid

Jonathan had never really liked me, Jonathan being the step son of my wife Samantha. He was in his thirties married, so why he had taken such an exception to me marrying his mother I did not know. The only thing I could think of was he saw me as sponging off Samantha. She was a successful business women and me, well I tried but often failed so most of the time I was living off her. Jonathan was a successful cosmetic surgeon so I guess he saw me as a looser. His father cheated on...

2 years ago
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A Ladys Sissy Maid

A Lady's Sissy Maid By Steve Andrews Steve was single and it had been awhile since he was in a meaningful relationship so one Saturday afternoon he was aimlessly perusing a local fetish contact newspaper when a particular ad caught his eye. It read: Sissy Maid Sought by Refined Beauty Classy, beautiful and refined lady is in search of a sincere sissy to perform my household duties and become my personal servant. Applicants must be docile, follow instructions and have a...

3 years ago
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Sissy Maid

SISMAID.TXT by Cindy V. femdom, TV, humiliation This is the fourth fantasy story in a series of five written at the command of my creative mistress, inspired by page 46 of the January, 1995 issue of Cosmopolitan magazine, a pictorial entitled "In Search of the Perfect Bra." This story involves the model in the bottom photo - Padded. My mistress has a date tonight. First I am to dress as her "personal" maid. She took great care to emphasize the word "personal." Then I am to help her get...

3 years ago
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Sissy Slut Maid

"They'll be here soon, go and get changed baby" My boyfriend said to me. I knew straight away what he meant. Every time his mates would come over, they liked me dressed up as a sissy maid to serve them in any way they pleased including, fetching them drinks, food or just being their foot stool. Once they all felt the need, they would all fuck me at the same time. My boyfriend, Owen, loved to dominate me and share me with his mates. I headed up stairs to get changed. Found my maid outfit, and my...

2 years ago
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Sissy Sister Maids

You look at the maids dress hanging on the wardrobe and your sissy clit tingles. The hem is short and has a froth of petticoats that will make it lift almost to the horizontal. The waist is narrow so you are guessing you are going to have to wear the corset that is currently in your overnight case. The neckline of the dress is low and plunging so it will flaunt your fake sissy tits, once again your clit twitches. Finally the sleeves are short ending just over the shoulder. You love the...

2 years ago
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A Pretty Sissy Bridesmaid

A Pretty Sissy Bridesmaid Preface. This is my third attempt at TG fiction, following the first two chapters of my other story, The Dress Shop (third chapter is on the way soon, following an extended writing hiatus!), and another story which is (as yet) unpublished on FM. First of all, I'd like to address the fact that the story below is very much a 'genre piece'. That is, it knowingly contains many of the stereotypical plot contrivances that the majority of TG fiction...

3 years ago
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Becoming a Career Sissy Maid

I have been submissive for as long as I can remember. Growing up I adored my mother and would watch everything she did around the house. Eventually I would help her with more and of the cleaning, cooking and laundry. She playfully called me her maid when I was helping her and I began to refer to her as Ma'am. When I was 13, we decided that I should go to a friend's Halloween party as a French Maid. For some reason this really excited me! My first masturbation fantasy was imagining...

3 years ago
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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...

3 years ago
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Sissy Maid

I was just out of high school working at a convenience store. Two of my regulars were a nice gay couple, both were a little feminine but one was definatley fem always wearing pink shirts and revealing shorts in the warm months. One night while I was talking with my friend about coming up with the money to buy my girlfriend an expensive gift they came in and where listening to the conversation. After my friend left the more feminine one named Toni came back.He said I could not help hearing you...

4 years ago
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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...

3 years ago
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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...

3 years ago
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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...

3 years ago
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How I turned office newbie into sissy Part 2 Tru

As soon as I got home after dropping T off I got set to work, booked a semi-local hotel, set my alarm and got an early night. Woke up at 7am with the hardest morning glory I've had in a long time. Was tempted to have a wank but thought I'd save my cum for my sissy. Sent T a picture of my cock and he replied "Can't wait Sir, I'm so excited but nervous". I didn't reply. So I went out early to buy some supplies, went to the local adultstore to buy an enema kit, lube, lace thong and small butt...

1 year ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

1 year ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

3 years ago
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Sissy Gracie Life Begins Anew

sissy gracie As we all know, this is a work of fiction. Parts of this are true. The beginning premise did happen. True and played out by moi. A lot of the truth has been embellished. Enjoy. As a blossoming sissy and knowing and accepting what a good sissy does.... this sissy decided to pay a visit to the local ABS..That is an Adult Book Store. Located in a large city in South Fl. Once inside, and checking out the mags and dildo's, i walked into the private video area to...

2 years ago
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Sissy Julian Chapter IV A New Morning

Julian begins his new Lake Orenda regime as he is quite uniquely prepared for a day in the village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention very dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated R. ...

3 years ago
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Sissy Clinic for Bois Chapter One My New Sissy Client

Sissy Clinic for Bois, Chapter One: My New Sissy Client Summary: A young woman meets with a rather unconventional psychotherapist who offers a unique form of treatment aimed exclusively as effeminate young men. "I appreciate you taking the time to meet with me," Jaiden Chapman told me as my assistant Susan served us both coffees. "Professor Greene at Texas Woman's University recommended you," she continued. "Professor Greene, Kristen, is my thesis adviser -- I'm working on my...

2 years ago
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sissy cunts New Life Pt 1

sissy cunt's New Life - Part 1 The plane finally touched down in Cape Town. It pulled to the gate, and the tone sounded, signaling that we could stand and take their luggage from the overhead. Grabbing my purse, i slung it over my shoulder and stood, stepping out into the aisle. i ignored the disapproving stares of the other passengers, my face turning bright red. They could clearly see the business cards, condoms and make up through transparent sides of my bright pink purse. i...

1 year ago
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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...

3 years ago
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Sissy Clinic for Bois Chapter One My New Sissy Client

“I appreciate you taking the time to meet with me,” Jaiden Chapman told me as my assistant Susan served us both coffees.  “Professor Greene at Texas Woman’s University recommended you,” she continued.  “Professor Greene, Kristen, is my thesis adviser — I’m working on my M. Ed. in curriculum design, and when I shared my story with her she was certain you would be able to help us.”I recognized the professor she was referring to immediately from working with her several years earlier when I...

Femdom
2 years ago
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Teaching the Sissy Maid Workshop at the MVG Chapter One Training a New Sissy

I simply loved teaching the introductory Sissy Slave Classes at the Matriarchal Values Group, or MVG, and since the class is limited in size it is almost always fully enrolled and most people who take the course end up registering months early to make sure they will have a place secured for the upcoming class.The Matriarchal Values Group, or MVG, was a private society of like-minded, dominant women who believe and live our lives based on our individual interpretations of what it means to be a...

Femdom
2 years ago
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A new Master for sissy 2

I was shaking as I stood at the counter waiting to buy Master’s coffee. I knew I had taken a major step by leaving my mobile phone with Him, and that it was a complete leap in the dark. At this stage I was more scared than excited, already questioning my judgement, almost wishing I’d not been so stupid as to open my life up to a complete stranger, giving Him the power to control and ultimately destroy me. But it was too late for second thoughts, and as I took His coffee upstairs and walked...

2 years ago
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Roommatersquos pictures Turning me into his sissy

I sucked my roommate’s cock and swallowed his creamy jizz almost everyday after that first time. He had called me out alittle, teased me, saying that he knew I wanted his cock, knew that I wanted to suck cock. Of course he was right, but how did he know? How did he know I would so wonderfully, happily and eagerly slide to me knees and pleasure his beautiful dick with my mouth. How did he know that it would come so naturally for me?He had said he sent me these pictures of his dick by accident,...

3 years ago
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Masters Sissy Slave Chapter 7 A new game

Chapter 7 - A new game Again awaking in the morning in a simple straitjacket, Masters control was now so strong that I considered a straitjacket simple! In Masters arms I felt a huge sign of relief that my evening was over but again I had to resolve myself to the fact that this was my life now. My body was screaming in pain, the torture inflicted on my gorgeous breasts was beyond what I had ever imagined. It must have been a sign of my diminishing mind and need to please master that...

1 year ago
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New GF Trains Me to be a Sissy Slut

"That's it baby! You are such an amazing cock sucker!" I moan around the cock in my mouth as I bob up and down quickly. I feel hands on the back of head grab my hair to stop me from moving up and down the amazing 10 inch black cock. I've been kneeling for almost twenty minutes slowly working this monster. I've only been able to take just over half of the cock so far. "You are doing very well sucking your first dick. Though a good cock whore needs to learn to deepthroat and feel what it's like...

3 years ago
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Club Gomorrah The Sissy Saga Chapter 3 The New Girl

The headset was suddenly dead, it was only moments later when she heard a voice call out that she realised the moaning was her own. “I said that’s enough Slut.” Pain shot through her as the collar around her neck began to shock her. “Dumb slut. The fun’s over, your Master’s waiting.” The woman sighed, and the collar sent another shock. “That one was for making me wait. Clean her up and bring her to the viewing room, and don’t fuck around. The guests are waiting and I want them to see my new...

3 years ago
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"Life can't get much better than this," Jack thought aloud as he laid around his family pool. Jack was the heir to his family's vast fortune and constantly thought that this made him better than everyone else. This was especially true with regards to his younger sister. Jack was 19 years old and loved to threaten his younger sister, Jackie, about how if something ever happened to their parents she would find herself penniless and destitute. The thought of his 18 year old sister...

Horror
1 year ago
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Birth of a New Sissy Part III Completion

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3 years ago
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The New Maid

The New Maid By Emily Ross [email protected] Part One - Vicky's Story I hadn't seen my sister in three years while I had been working in Australia. Now here I was knocking on her front door. A maid answered. 'Miss Simmons? Come in. Let me take your suitcase. Would you like to go into the drawing room? I'll tell Mrs Hardy that you are here.' 'Thank you.' I went into the drawing room and sat down. A minute or so later my sister came in. I jumped up and gave her a hug. We...

3 years ago
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Newhart The Made Maid

"Stephanie, I never said you weren't pretty. I just said that some men prefer, well, different types of women." Joanna grunted as she lifted a sack of potatoes from the car. "You can't expect every man to drool over you." Stephanie continued to sort through the brown grocery bags, searching for the one with lightest load. "And why not, Joanna? You don't really expect me to believe those boys were looking at you in THAT way, do you?" Joanna, a tall, slim woman of about 40, pushed a...

2 years ago
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As a submissive and obedient sissy with a deep craving for humiliation I’d served a few online Masters during my 50’s, but when I hit 60 I started to crave the experience of serving a Master in real time. I knew that to do this I’d need to join a site through which I could contact local men, and so created a sissy profile on fabguys. I uploaded pics of me as a sissy, wrote a reasonably honest summary of my experience to date, made it clear that it was real domination I was after, and kept a...

1 year ago
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SISSY MOMMYrsquoS NEW LOVER

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3 years ago
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I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the answer to that! I'm sure as you were pathetically scowling the web to find things to excite your little...

Crossdressing
2 years ago
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Alice the New Maid

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Spanking
3 years ago
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A Sissyrsquos New Daddy Search

I couldn't sleep last night so I figured I'd fire up the laptop. Lately I have fantasized about being totally dominated and used by a real top daddy since my old one moved away. When I’m in this type of mood I usually will do a quick hookup, but I was in such a sassy state, I really missed having a man taking charge of me, to humiliate me. It was a good night, I was getting a lot of messages from guys interested in teaching a little sissy how to keep her daddy happy, and how my fat brown ass...

2 years ago
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2 years ago
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sissy Meets her New Daddy Ch 1

So I took the plunge and put out an ad on Craig’s List. I was travelling in a city about 120 miles from home and figured this was far enough to not be found and close enough to go back if I had success meeting a fuck buddy that could be longer term. I got myself all primped and wore a tight print dress, matching bra panty set subtle yet slutty makeup and my fave long blonde wig. The ad attracted immediate attention and I was sure to mention I was a sissy who wanted to be treated like a girl. I...

2 years ago
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My New Maid

My New Maid By Margaret Jeanette Sarah and Jim Toomey were enjoying a steak at their favorite steak house. He was looking all around and observing the other patrons. "What are you looking at?" "I am just observing all the customers. Do you notice all the men are wearing dark suits and all the women are wearing bright, colorful outfits? Look at the woman at the table next to us. She is wearing a bright yellow blouse with lots of ruffles on it. She looks so feminine. Look...

3 years ago
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2088 Its 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...

2 years ago
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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...

1 year ago
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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...

2 years ago
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The SissyMaster

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...

2 years ago
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The Sissy App

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3 years ago
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A Sissy called Jezebel Part VIII

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2 years ago
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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...

3 years ago
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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...

1 year ago
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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...

4 years ago
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Tweak Chapter Four Whats 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...

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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...

2 years ago
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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...

3 years ago
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Sissy School Part 3

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

1 year ago
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Sissy tasks

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

3 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

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