The Sissy Show Finale free porn video

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Jessica and George Jessica sat contemplating George across the breakfast table watching him eat his pancakes and drink his spiked tea. At first she was not sure what to do with Barbara's suggestion on how to sissify him, yes he was a prude and insisted the lights were out when they had sex.....which was not very often. But what did she think dressing him as a hooker would achieve, hell his parents were devoutly religious he had had a life time of prudishness there was no way a drug was going to change that! And then it hit her, she looked around the room confirming her realization. The furniture in the house looked frugal which in fact it was. George did not agree with splashing his money on fancy furniture....but what applied to the house also applied to Jessica, her clothes were dowdy and well worn. She often drooled at the clothes Barbara wore and as for her handbags, George would have had a heart attack at the price of some of them. Jessica was given a budget for both the house and herself, even then she had to explain every single expenditure "Why did you buy a new bag this month?" "Because mine had a hole in it" "Couldn't you have fixed it" "No dear the seam is frayed" "Let me take a look" She sighed remembering her last conversation about money. The most galling thing of all was that she knew his bank balance had lots of zeros! It was for their happy retirement he said but she knew most of it would be spent on his parents keeping them happy. She had considered taking him down to the bank and drawing out all his savings but she knew that would have consequences. Besides she had had a much better idea thanks to Barbara. "George go upstairs, take off all your clothes then go and take a shower. In the shower I want you to shave off all the hair from your neck down......" she ordered "Yes dear" he replied simply. "When you are done stand in the middle of the bedroom and wait for me" "Yes dear" he headed upstairs. She finished her breakfast and then followed him upstairs When she arrived George was waiting patiently in the middle of the bedroom as ordered. She inspected him noticing there was stubble in a few places, she would have to send him out for some hair removal cream she realized. She opened the box she had been given and looked at the clothes inside, she sniggered at the scanty apparel. She took everything out and then began to dress George starting with the panties, red and transparent. At first she thought they were open crutch but then she saw the label and realized the hole would in fact be over his puckered hole! She giggled impishly. She helped him into them noticing as she did that his flaccid four inch dick fitted snugly into them. She fitted a matching bra and then dropped the rather large fake tits into the cups. They were obviously fake but that is the way many tranny hookers seemed to want to look. She fastened a red and black lacy suspender belt around his waist and after rolling fishnet stockings up his legs attached the suspenders to the stocking. On his feet she placed trashy looking red mules, open toed with a toes strap of fluffy red feathers. She helped him to slip into a diaphanous open front negligee that was edged at collar and cuff with the same fluffy red feathers, it barely hid his exposed puckered hole it was that short! The final item was a long blonde curly wig. She commanded him to sit at the dresser and made his face up. Heavy foundation to hide his stubble, blusher, eye shadow and attached long glittery false eyelashes, all in slutty shades of red. She slathered lots of "Mother Pucker" on his lips, a stimulant makeup that made them swell, then she applied "Cocksucker red" lipstick just as liberally. When she had finished she let him see his reflection laughing at the glint of fear she saw in his eyes. Not for the first time she wondered what he could be thinking. George was average build and thanks to his frugal character was not overweight from over eating so he did look passable as a female?a somewhat whorish female! "There you go the perfect hooker look...." she winked at the reflection. "But a hooker needs a hookers name....mmmmm" she watched him cringe slightly "Georgia....Georgia Guzzles Cox" she burst into fits of laughter. As if on cue she heard the door bell ring and contemplated sending him to go and answer it but realized it might not be who she was expecting "Stay here and come when I call" she ordered Georgia She skipped down the stairs and opened the door The woman at the door was tall raven haired and beautiful in a severe way. Jessica envied her but not for her looks, no it was the expensive clothes she was wearing. Beside her Jessica definitely felt dowdy. "Hello I'm Cynthia........Barbara sent me" she said with a smile "Yes.....Yes, come in" She took her to the living room where they sat "Barbara tells me you have a business proposition" she stated matter of factly "Yes as the owner of the local strip club I hear that you hire out booths" Cynthia raised an eyebrow and Jessica realized she must be wondering what a dowdy house wife was doing asking such a question "Well......unofficially" she answered "I want to hire a booth" Jessica stated nervously, charging ahead before she lost her nerve "For yourself!" again the raised eyebrow "No.....no.....let me show you.." giggled Jessica still nervous under Cynthia's gaze She definitely seemed to be a formidable woman but then she was the owner of several strip clubs! "Georgia!" The clip clop of heels could be heard and then the pathetic figure of Georgia appeared in the doorway. Her eyes flew open when she saw the other woman but it did not stop her from moving to the centre of the room and standing obediently head down "This is Georgia........my husband" "You want to pimp your husband!" Laughed Cynthia With that she stood and moved around him examining him as she did. "Okay sixty, forty in my favor of everything she takes" Cynthia stated business like "Sure.....sure....." gushed Jessica not sure of what she was agreeing to "Okay deal....." and they shuck hands Jessica smiled when she heard Georgia's nervous intake of breath "Let me get some publicity photos" smirked Cynthia With that she produced her phone and ordered Georgia to pose seductively. Unfortunately her idea of seductive was not very seductive! "No!.... more like a woman" Cynthia demanded She tried different poses "No, now you just look a man trying to look seductive!.......and failing abysmally!" She got out an iPad and began searching "Like this!" She showed Georgia a picture of a naked woman, back turned, looking suggestively over her shoulder. This did the trick and in this way she got several more pictures ending with one were Georgia was touching her toes flaunting her pussy that was scarcely covered due to the shortness of the negligee. "Go and make us a rum and coke" she ordered As Georgia was doing this she uploaded the pictures to the strip club website. When Georgia returned she took the drink and ordered her to massage her feet. Jessica was impressed with both Cynthia's dominant nature and Georgia's obedience. She realized that was exactly how she was going to treat Georgia from now on. "It seems we have a few takers already.....can you get her to the club tonight Jessica was shocked at how quickly things were happening "Sure......what time?" "Be there for six.....and make sure you lose the stubble" she quipped So the women chatted whilst Georgia massaged both their feet and then Cynthia took her leave a wry smile on her face. "What must she think of me" mused Jessica Then she remembered Cynthia's dress and went online to see how much it cost, whilst she was there she drooled over some handbags.....soon.....soon she mused. She sent Georgia to undress and shower and then she sent her shopping for hair removal cream and perfume. She also told her to swing by the local fancy dress shop and pick up as many women's costumes that would fit her. When Georgia returned she had her strip then coated her neck down with hair removal cream. Whilst this was working she had lots of fun sifting through the costumes Georgia had returned with. Maid, nurse, witch.....sexy witch, Amazon, mistress.....now that would be interesting, I think I will wear that she mused. Once all the hair was gone she ushered Georgia into a scented bath and then prepared herself some dinner, none for Georgia she was watching her weight. Jessica packed up all their things and drove them to the strip club where she was greeted by Cynthia and ushered inside. A couple of girls led Georgia away and Jessica followed Cynthia to what could only be described as a small cinema. There were large comfortable chairs all arranged around a big screen which currently showed an empty room. Jessica guessed it was the booth Georgia would soon be occupying. It was round with a padded bench all the way around the outside. In the centre of the room was a circular couch big enough to lay down on, Jessica was handed a drink and the women sat. On the screen she saw Georgia brought to the room and made to kneel. The resolution on the picture was so good Jessica could easily see the makeup that Georgia was wearing...and it was very slutty, in keeping with her outfit. Moments later a man stepped into the room. He looked just like a business man which Cynthia informed her he was, in town and looking for something different. "Actually he is a regular and tips well if he is pleased" confessed Cynthia Jessica watched in awe a strange feeling in her stomach as she pimped her own husband. Then she remembered all the times she had to virtually beg for money and she hardened her resolve "So you're the new.....girl" quipped the man "Yes Master" Georgia replied meekly Jessica smiled at this and Cynthia said "All my girls are obedient! Jessica watched as without bidding Georgia stood and began to undress the man, undressed Jessica noted he was average build with an average cock. However Georgia exclaimed that it was the biggest cock she had ever seen and began to suck on it. She was shocked at how readily Georgia had taken to the new role. She watched mesmerized as Georgia sat the man down and then knelt between his legs taking his cock deeply into her mouth. "I can't believe how eager she is "gasped Jessica "Oh I know all about Barbara's new drug.....let's just say the girls have been whispering in Georgia's ear whilst they were getting her ready" she sniggered. Jessica watched enthralled as Georgia expertly sucked the man's cock bringing him to a quick climax. Then salaciously licking her lips she climbed up onto the couch beside him and flaunted her sissy pussy. Needing no bidding he quickly buried his still hard cock into her eliciting a squeal from her. The fuck was long and slow and they changed positions twice. He finally shot his load into her with her on her back begging him to fuck her hard! When he had done Jessica was just as exhausted as they were from fucking and her own pussy was sopping wet. After Georgia much to Jessica's surprise had begged to clean his spent cock the man dressed and left leaving what looked like a very large tip. The girls came and collected Georgia and a maid tided the room "Is that it?" Asked Jessica "Oh no dear, Georgia will be taken to freshen up and given an enema.....we need her clean and fresh for the next client" she winked A short while later Georgia was returned to the room and the next client arrived. He turned out to be a black man of similar build to Leon. Remembering his rather large cock Jessica licked her lips "Hey white boy...." growled the man "I always wanted to see white faggots lips around my cock!" He grinned squeezing what appeared to be a large cock through his jeans "Oh my!" Gasped Jessica Without thinking her fingers drifted between her legs "Where are my manners....." exclaimed Cynthia "Do you prefer girls or boys?" She asked a bewildered Jessica "What?........oh.....Boys" Cynthia picked up a phone. "Send Max to us please" A few minutes later a young man entered the room, Jessica sighed at his athletic physique, which was clearly on display because he was only wearing a pair of skin tight amply filled boxer shorts. Without a word he moved to Jessica and knelt between her legs, gently moving them apart he started kissing his way up her thighs, Jessica groaned in delight at his ministrations. She dearly wanted to watch what was happening to Georgia but was mesmerized by Max's questing lips. She took a quick glance to find that George was now kneeling at his feet whilst he mashed her face into his crotch. Max found her panty covered pussy and her attention was drawn back to him. He licked avidly at her pussy through the panties and she wriggled in appreciation sighing, emboldened by this he reached up to take hold of her panties "Oh god I need your tongue on my pussy" she moaned Gently he pulled them down her thighs and then completely off before returning to his licking. As soon as his hot wet tongue hit her pussy she began to shudder and climax. All thought of Georgia was gone as she screwed her eyes shut and surrendered to the glorious feeling. Having filled her initial desire Max continued to lick but this time more gently, this gave Jessica time to recover and as she did she now noticed that the black man was completely naked and Georgia was sucking on his balls. Jessica watched the screen as Max slowly built her to the next climax and Georgia attempted to take the man's ten inch cock down to the balls, unfortunately he could only take half the length. "Mmmm looks like Georgia needs some practice" noted Cynthia The black man however would not be happy until Georgia had taken his full length so he had her lay on the couch with her head hanging off. He then slid his cock into her mouth much like a sword swallower. She did after a few attempts manage to take a few more inches but he could not fuck her like that. So because he was angry he made her kneel on the couch and slammed his cock hard into her making her scream "That's it white boi scream......scream for big black cock!" He growled Luckily he was far too excited to last too long and soon he was shooting his load into her sissy pussy berating he for being a faggot and calling her all sorts of humiliating names. To her surprise she noticed Georgia was also shuddering and realized she was climaxing! The black man noticed this and ridiculed her all the more! This caused Jessica to experience her second climax so she failed to see Georgia forced back onto her knees and made to clean his cock with her tongue. When next she looked at the screen Georgia had been taken to freshen up. After this Jessica was more interested in Max fucking her aching pussy to take any notice of Georgia's exploits. The next time she saw her was when she was getting into the car for the ride home. Once home Jessica checked her bank balance, two thousand added in one night! She marveled, she then opened a shopping website and started browsing. The next day Jessica dropped Georgia off at the club for practice and then headed into town to do some shopping, after all she needed some new clothes for when Max came to pick her up later. The sissy Show The four sissies stood nervously behind the curtain, outwardly they did not seem nervous but it could be seen in their eyes, all except one that was, in her eyes was a look of excitement! They were nervous because behind the curtain they could hear the murmur of many voices, and all it seemed female! Barbara stepped out onto the tiny stage that had been set up in her dining room. Before her sat around forty of the town's most prominent woman. On the front row where her friends beaming up at her. Barbara had a large house so although there was a large number there was room to spare in the dining room that could almost be called a hall. "Ladies I am glad you could all come, and I thank you all for coming. Tonight is going to be a real treat for you ladies and after the main show I have a proposition for you all..."she smiled There was a murmur of questions so she carried on "Yes I know I am being mysterious but all will be revealed after the show. So to the show, it is a sissy show....we have sissified four men and turned them into what they were destined to be...." she smiled a wicked smile at the murmur of surprise "But ladies I will not struggle to explain myself......let the girls do that" with that she beckoned to the sissies in the wings "Come on girls time for the show" With a nervous gulp the sissies minced into the spotlight Sissy hooker Georgia came first, followed by rubber bondage sissy Brandi next came sissy lesbian lover Daphne and bringing up the rear Sissy maid Francine. As they all minced onto the stage there was a gasp of shock, then a few titters, then laughing and clapping. Soon all the women were shouting and jeering as the sissies flounced across the stage like it was a catwalk. Barbara grinned seeing the audience quickly warming to the show. Finally Barbara had them line up across the stage. "Now girls step forward one at a time and introduce yourselves" she commanded Georgia the Sissy Hooker stepped forward first, she moved to the microphone and did a deep curtsy. Barbara smirked seeing the discomfort in her eyes, as she knew each girl had been coached by their Mistress on what to say. "Hello ladies my name is Georgia, as a man I only gave my wife sufficient money to look after the house and feed us, leaving nothing for her to spend on herself. If she did need money I made her demean herself for it and would not usually give her it anyway...." she paused as there were boos and hisses from the women "In the meantime I horded my own money intending to use it for my own needs and wants. Mistress showed me the error of my ways and now I am selling my sissy ass so that she can live the life she has always wanted" There was clapping and cheers from the crowd as once again she curtsied and returned to the line. Next up was Brandi the rubber bondage sissy, she mince and hobbled to the microphone. Barbara could see that despite the drug Brandi was enjoying herself and once again she was jealous of Chrissie. "Hello my name is Brandi and I am Chrissie's rubber bondage sissy..." She looked towards Chrissie and did a delicate bow, obviously the dress precluded a curtsy. "We love each other and recently we have both discovered a love for bondage and my passion for rubber..." there were sighs and clapping from the crowd "I now find that I adore her even more because although I did not want to be seen in public dressed as I am she pushed my boundaries and brought me here" she smiled happily As she minced back to the line there was a loud round of applause. Nervously Daphne took her place. "Hello ladies my name is Daphne and I am Wendy's lesbian lover...." There was a ripple of shocked gasps around the room. Barbara looked towards Wendy and saw she was blushing bright red. Well the cat was out of the bag now, maybe it was for the better. "As a man I married Mistress Wendy simply to further my career. I knew marrying her for her money would give me a better status with my family. I was not a good lover to her and have had two mistress and regularly pay for hookers..." This time there were hisses and jibes about castration. "Wendy has taught me that I am better as a sissy lesbian and now I am devoted to her. I am her girlfriend and lover" she smiled nervously before returning to the line. Last was Francine, she daintily lifted the hem of her uniform and curtsied causing a ripple of laughter from the crowd. "Hello Mistresses, my name main Francine. As a man I was a chauvinistic lazy pig. I did not lift a finger around the house and expected to be waited on hand and foot. I drank beer and watched football all day. Mistress Carla showed me that my true place in life was as her obedient sissy maid. Now I do all the housework and I am her personal pussy licker" At this there was a ripple of laughter around the room as she returned to the line and Barbara stepped up. "Well ladies you have now heard them all speak. Now it is up to you to decide which one of their wives, lovers or mistresses will get an all expenses paid two week holiday to the Bahamas, courtesy of my ex husband." she sniggered "As each sissy steps forward you will cheer, remember for the most deserving wife. The loudest cheer will win the holiday" "Sissy Hooker Georgia" There was a round of clapping and some cheers "Rubber Bondage Sissy Brandi" Although it seems the women loved Brandi's devotion the cheers were not as loud "Sissy lesbian lover Danielle" This time the clapping and shouting was much louder in fact some women stood to clap "Sissy Maid Francine" There was support for Carla but it was not as loud as that for Wendy who once again blushed deeply "So it would seem we have a winner.....well done Wendy....." the women clapped even louder "Oh hell they can all have a holiday.....after all my ex is paying "she laughed The crowd all started shouting and laughing and the girls all beamed at Barbara Barbara watched a look of satisfaction on her face. The girls came and hugged her and then led their sissies off the stage. "Okay ladies now to reveal my secret and announce the proposition I eluded to earlier. First the secret, how did I get those men.....girls to demean themselves as they did? Simple I used this drug created by my ex- husbands.....actually my pharmaceuticals' company" she flourished the glass file and noted she had the attention on everyone in the room. "Once given to the subject you have complete control over them....as you have seen" There was a ripple of laughter around the room. "My proposition is also simple, am willing to give you all a supply of the drug to use on your husbands. It's time the women of this town took control and showed the men how it's done!" The crowd burst into rapturous applause, Barbara however scanned the room to check for anyone not happy with the plan. To Barbara's surprise and joy they were all smiling and clapping, why not even if you didn't want to sissify your husband surely you would want to know his deepest desires and ambitions. Barbara stepped off the stage and engaged with the women answering all the questions they had. Over their heads she noted that Buttercup had started serving drinks. A short while later she saw that Francine had also started serving drinks and nibbles. Barbara smiled as Francine blushing soon became the centre of attention. Her panty covered ass was swatted causing her drinks tray to wobble and the women around her laugh. Checking that Buttercup was still serving drinks, Barbara took the chance to slip away and tour the house. The first room she came to was the games room, it did have a billiards table in the centre until recently. Now in the centre of the room was a bondage frame, and to it was strapped Brandi. Her hips were strapped to a padded bar and then her body was strapped to an inclined bench so that her ass was higher than her head. Her ankles were attached to a spreader bar which pulled the rubber tightly over her ass. Her head and hands were secured in stocks and a leather chair was pulled up in front of them. The women who was lounging in the chair had her legs hooked over the stocks which meant that Brandi's face was buried in her pussy. She could see Brandi's head moving rhythmically so she knew Brandi was licking her pussy. Chrissie was brandishing a whip testing it for flexibility and swishing it around. Barbara paused at the door to watch as Chrissie placed it against Brandi's rubber covered ass, she saw the ass tense at the touch of the whip. Chrissie reached back and then SWISH.......CRACK! A shudder ran down Brandi's body and she groaned "OH!" Exclaimed the woman "Again!" She demanded SWISH........CRACK! "Yes....yes....again....faster" the woman cooed Barbara left them to their fun noting the tempo of the strokes increase and as they did so did the woman's moans. The next room she came to was the study. She had not changed this room but when she looked in someone had. They had removed the table that sat between two leather chairs. In its place was Georgia, she was currently being fucked by a woman with an eight inch strap on dildo. At the same time she was sucking the strap on of another woman. Barbara noted Jessica sat in one of the leather chairs counting a wad of money. Between her legs was Leon eagerly lapping at her pussy. Jessica noticed Barbara and grinned. "Who would have known there were members of the PTA who wanted to fuck the head teacher in the ass!" She sniggered. "Don't ware him out I need him later" quipped Barbara pointing at Leon before moving on The final room she wanted to look into was the boudoir, a downstairs bedroom. When she felt the need for a fuck with Leon but did not want to go to the bedroom she would use this room. The only furniture it had was a large heart shaped bed. When she looked in all she could see was a tangle of female bodies. She noticed Daphne was getting her sissy pussy fucked, whilst her face was buried in a hot wet pussy. The woman fucking Daphne's pussy was Wendy, whilst she passionately kissed another woman! "Mmmm.....looks like Wendy has made some new friends" mused Barbara licking her lips. Maybe I will join them later she decided heading back to the dining room. As she walked she smiled like the cat that had got the cream. Now she had more women to test the drug, once she was happy that there were no side effects.......no serious side effects she would bring the whole town under her control, her pussy throbbed at the thought "Maybe I should re-claim Leon" she mused

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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...

2 years 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...

4 years ago
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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...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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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...

4 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...

2 years 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...

3 years ago
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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...

3 years ago
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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...

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...

4 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...

2 years 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...

4 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...

4 years ago
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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...

3 years ago
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The Young Sissy Chapter 3

I was running through an empty parking lot...looking for someone, or something, but I wasn't sure who I was looking for...or what. All I knew that was no matter how hard I looked, how far off into the distance I stared, all I saw was miles and miles of concrete. It was an oppressive emptiness, the vastness of the open space crushing me. I fell to my knees in despair. I don't know why I was looking anymore...everything I had seen up to this point was testament to the futility of hope. At...

4 years ago
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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...

4 years ago
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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...

2 years ago
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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,...

1 year ago
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The 150 Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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407am 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...

1 year ago
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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...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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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...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

3 years ago
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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...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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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...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

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

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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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...

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