100 Sissy Points free porn video

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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 a story idea that you'd like to explore with me. Enjoy! xoxo-Sissy Michelle IRL. One Hundred Sissy Points The poor sissy was at the point of tears. She had been bouncing up and down on her boyfriend for the last two hours. Her "boyfriend" was a nine inch dildo that was attached firmly to the hard wooden chair in front of her computer. It usually has a lot of lube on it, but that must have worn off quite some time ago. She grunted as she bounced because her sissy balls were attached to the seat of the chair by a five inch chain. After much experimenting, I'd found that was the perfect length to allow her to enjoy bouncing up and down, while not risking the possibility of the dildo slipping out of her sissy pussy. She didn't know yet that I had ordered and new boyfriend for her to play with. This one was thirteen inches and substantially wider at the base. But that's a surprise for tomorrow. Today was the third Sunday of the month and my naughty little slut had only earned 99 sissy points this week! That's why she was bouncing desperately up and down on her dildo while I, and several other gentlemen watched her via the webcam. I had graciously allowed her to do some extra credit work, at the rate of one point per hour as long as she didn't stop bouncing and kept repeating her sissy mantra for the whole world to see via the internet. "I am sissy michelle," she grunted out through clenched teeth. "I am nothing but a submissive sissy slut. I am nothing but a collection of holes for horny men to use anyway they see fit. I am nothing but a sex slave for my Master to use and abuse however He sees fit. I promise to be an obedient sissy slut. I promise to be a horny sissy slut. I promise to be the best sissy slut that I can be, because I know that Master will destroy me if I ever fail." That last part was important. Sissy has been locked in her chastity for the past six months and she knows that part of me wants to weld the damn thing shut so she can stop dreaming about earning enough points to earn a sissygasm. I would have done it a few months ago, but I do like to remove her cage from time to time so that I can clean it and shave sissy's private parts with my straight razor. The look of terror in her eyes as I place the blade against her tiny little sissy balls is one of my favorite parts of this whole relationship. I text window popped up on my screen. It was SadoMonster18 informing me that "the little slut has stopped." Sure enough, the exhausted sissy had collapsed down on her boyfriend and was silently sobbing in defeat. I almost felt sorry for the slut, but then SadoMonster18 asked if he could come up with her "punishment." I was tempted, but I had my own plans for sissy. I've had plans for her ever since I fist found her watching sissy hypno videos, some eights months ago. I composed myself and turned on my webcam. It was pointed directly at my hard cock--that's all a sissy needs to look at. "Why did you stop, sissy?" I asked in my most forceful voice. She could barely muster the energy to respond. "Fine," I scowled into the cam. You have exactly two hours to compose yourself, then we will decide what your punishment will be." I typed my pass code into my computer and heard the audible click as sissy's Dreamlover vault opened on her end. She reached in and took out the key to unlock her chains. Then, as she'd been trained to do, she put the key back in the vault and closed it as I locked it from my end. Ain't technology great? I don't know how they used to train sissy sluts in the old days. Laughing, I got up to grab a beer and go check on Candy--the sissy I had tied up in my bed at the moment. I decided to give her a rough fuck while I thought about what was coming up next for sissy michelle. "Year two," I thought, as I shoved my cock in and made Candy squeal." Allow me to step back and explain. I give my sissy sluts a series of goals that they are required to meet or else they incur one of my punishments. The sissies quickly learn that I am not somebody to trifle with. My punishments are usually along the lines of getting another tattoo or piercing. Most of my sluts have so much ink and steel in them after a few years of service that they can no longer get through airport security. One particularly naughty sissy pissed me off so much that I had a weighted steel ring permanently secured to her balls. Then I tattooed my cell phone number on her ass along with a message that read "Any man, woman or dog may fuck this sissy whore, but please text a picture to this number so that I know she's being a good slut." Then I put her on a flight to Chicago, where one of her online admirers wanted to spend some time using her. I got four pictures sent to me from Airport Security. She was stripped down to her lingerie in a back room and stuffed full of cock and covered in cum. Unfortunately, the little sissy missed her flight, so I got a few more pictures while she waited for the next flight to Chicago. I decided then and there that I was going to make her take several cross- country flights each month. It's a nice way to thank our TSA officers for their service in keeping our country safe. Back to the story--I suppose that I should explain the point system. Sissy michelle has to earn 100 sissy points every week. She started out at just 50, but I like to add ten more points to the weekly requirement at the end of every month, whether she's been good or bad. After eight months with me, she is up to 100 points a week. If she is short points during one of the weeks, the difference will be added to her weekly requirements for the rest of the month. We meet on the first Sunday of each month for our review. I release her from her cage and then, if she has earned her 100 sissy points, she is allowed to stroke herself to a sissygasm while I fuck her. If she's short, she can expect to be punished. Let's talk points. Sissy is expected to wear her bra, panties, stockings and garter belt under her boi clothes at work every day. I text her at random times and she has five minutes to go to the restroom, disrobe in the stall and send me a picture as proof that she is properly attired. She has to hold a post it note up that has the day's date on it, along with the word of the day, so that I know she's being honest. When she sends me the picture, she earns one sissy point. She loses five points if she's late. Sissy is expected to rush home from work every night and doll herself up. I expect sexy lingerie and full makeup, jewelry and wig. Plus high heels, of course. She poses and sends me a picture. If I think she's put in enough effort, she gets another sissy point. She also spends time in front of her webcam each night. She has a group of horny men who like to chat with her. They pay a very reasonable fee for this chat session, which goes into a sissy transformation fund that I manage. The fund is doing very well, as I currently have 19 sissies who are in various stages in their training. I monitor michelle's chat sessions. If sissy works her ass off, she can earn up to one sissy point per hour, although I never give her credit for the full time served. That would be too easy. Of course the main way that a sissy earns points is by sexually serving men. A blowjob is worth five sissy points, as long as she sends me a picture that shows her whore mouth full of cum--splattered across her face also counts. It only counts if the man is satisfied and I can clearly see a post it note with the day's date and the "word of the day" clearly in the shot. I love the look on a sissy's face after she has spent an evening fucking four or five men, but doesn't earn any sissy points because of illegible handwriting on the post it note. They NEVER make that mistake twice. A good fucking is worth seven points, and if there is some element of kinky involved, it might even be worth ten sissy points if I'm feeling generous. Fill her mouth with your piss after you fucked her? Sure, why not? Ten points. Wrap her from head to toe in duct tape and then leave her mummified on the floor after you've had your way with her? Yes--ten points! I even had one instance when sissy was down on all fours blowing one of her studs when the guy's dog decided to get in on the action. The bitch was knotted so long that I was tempted to give her credit for a blowjob AND a kinky fuck, but then I thought I was getting too soft and went with the standard ten sissy points. There are some other ways to earn sissy points. A night serving in a glory hole is worth 25 sissy points--although it's not really fair to the sissy because she'd really be earning hundreds of sissy points every night that she's working the hole if we counted her efforts by each individual blowjob. Serving as a urinal slut is also worth 25 sissy points. Basically she spends the night tied up in a bathroom stall with an O-ring locked into her mouth. She's not allowed to swallow until she's told to flush, at which point she is expected to swallow everything down, lick her lips and beg for more hot piss. This one is also a bit of a trap, as I make her wear a sign around her neck with my cell phone number on it. It never fails. Somebody calls sissy customer service to complain that a drop of piss splashed out and got on their pants--something along those lines. I apologize and ask them to punish the sissy for me until we can get her in for some "advanced training." They almost always spank the sissy and then fuck her. When they are finished I tell sissy that not only will she not get credit for the fuck, but she will lose her 25 points, and another 25 should she get another complaint. I'm not kidding--one sissy came out of a urinal session owing me 475 points! And it was only the second week of the month, which means she had to earn 475 points to make up the difference that week, and the next two weeks as well. Then again, I had another sissy that was such a piss slut that people were calling sissy customer service to ask about renting her out for parties. I eventually sold the sissy to one of these men. I got a money order for 25K and sissy got a steady supply of piss and cock for the rest of her days. They lived happily every after. I know. I got a Christmas card that showed sissy trussed up under the Christmas tree while multiple streams of piss rained down on her. Back to poor sissy michelle. She reappeared in front of her webcam exactly two hours later. Her head was bowed and she was shaking with fear. The irony was that our official review wouldn't be until next week, but she had been short enough times in the past that I told her that she would be punished every time she was short from here on out. She caught the flu and missed the first five days of the week in bed recovering. I was nice enough to let her rest up until she got better, and then even helped her find some new boyfriends to stop by to help her make up the point difference. 100 sissy points isn't that hard for a sissy to earn. That's just twenty blowjobs a week. My sissies should all be able to earn 100 sissy points in a single evening! Still, michelle wasn't up to full energy, so she was short of her sissy quota and desperately begged for mercy. I extended the deadline by a few hours and set her to bouncing up and down on her boyfriend. If she could have lasted the whole three hours, she would be set. But she failed, so now she would be punished. What to do? What to do? I already knew that next week when I came into town for her official review I would take her back to the tattoo shop and have them permanently attach pink sleigh bells to her nipple rings and PA piercing. I loved the idea of making her jingle every time she moved, even while at work as a man, and I was especially looking forward to hearing the bells ring each time somebody pounded into her from behind. All things considered, that's not a very severe punishment. I'm saving those for later on when she's a little more adept--I've only been working with her for eight months so far. I usually train my sissies for three years before finding new homes for them. I've found that it's best to save the major changes for year two after the sissy has despaired of ever leaving the sissy lifestyle. Year two is when the sissy will get breast implants and be forced to go to work dressed fully as a woman. Sissy michelle would have some extra fun as her boss knew about her sissy tendencies as was allowing the office rumors to run rampant with the promise that next year she would become his sissy secretary and personal play toy while at work. Year two is also when we start tattooing makeup on her permanently. It's when she'll have all of her teeth removed so that there's never any chance that a man would nick his cock of her teeth. The advantage of this is a dentist friend of mine will fit her with regular looking dentures that can easily be removed, but they will come equipped with a special feature that allows them to be locked closed. The dentist has two sissies of his own, and their mouths are locked closed at all times unless he wants to unlock them for a quick blowjob. Those two sissies haven't uttered a single word for nearly four years now, which is exactly what the dentist wants. That will all be coming for michelle in a few months, along with regular nights serving as a sissy whore for a local pimp who likes to rent my girls while they are being trained. They don't get credit for the cocks the serve on these nights on the street, which makes it harder for them to find enough time fill their sissy quotas. That's exactly what I'm looking for. The sissy points start getting so difficult to achieve, and they earn so many penalties that the sluts despair. They are broken down and become mindless sexual play toys. I find that this is when hypnotic conditioning is most effective. Make no mistake, michelle has been staring at sissy hypno videos for several hours a day the entire time she's been in my service. That's what got her into the lifestyle in the first place, and I'm more than happy to let her goon out watching videos that will turn her into more of a obsessive sissy cocksucker. That's all just amateur hour right now. In a few months she'll be seeing a professional doctor who will implant some deep hypnotic suggestions. All of my sluts have a uniform set of commands that I can turn on or off whenever I get the urge. They will all become outrageous nymphomaniacs, practically humping the furniture like a dog in heat. Speaking of which, the doggie command is also quite popular. I know that a few of my buyers wanted sissies to keep in their kennels for the rest of their now completely canine lives. The bimbo option is the most popular. We can turn the sissy into the perfect mindless trophy wife who only thinks about shopping, looking pretty and sexually serving her husband and his friends. There are a lot of CEOs who will pay a pretty penny for one of my sissies knowing that he'll have the perfect bimbo wife to use at home so that he can concentrate on running his company the rest of the time. I must admit that one of my favorites is to teach the sissy a foreign language and then switch their language abilities on and off. One day they are an average kid from the Midwest, but a year later their English is completely gone and they only speak Spanish. If a sissy can't be sold (something that rarely happens) I can simply wipe her memories, leave her only with Spanish comprehension and then let Immigration Services catch her turning tricks in the barrio. They won't be able to identify her, so she'll get deported and who knows, maybe she'll be happy living out the rest of her life in Mexico? The memory wipe is the most important of these hypnosis procedures. Before I sell a sissy, I completely wipe her memories of me and my training. I can't afford to have a sissy out in the wild that could lead the authorities back to me. We wipe her memories and then wipe them again. All of my sluts are wiped five times. They end up with no past memories at all. They think that they sprung into existence as a sissy slut--which makes it easy for them to accept their fates. How do I know that the hypnosis works? That's the best part. The professional doctor who implants the suggestions is one of my sissies! Nobody knows that this respected pediatrician is a lynch pin in my sissy empire. She has access to some drugs that the CIA developed, and she knows the techniques that ensure the advanced hypnosis conditioning works. She also has a fully staffed office where my sissies can disappear for months at a time while they get broken down before being built back up to be the epitome of a perfect sissy slut. Plus, she has a staff of two geeks(also sissies) who help her create sissy hypno files that keep my girls motivated while they are being trained. They also have a few posted online where a randomly horny dude may occasionally stumble on the video and find himself getting hooked. That's what happened to Mike, now known as sissy michelle. She is openly sobbing now, ashamed that she has failed her Master (see the early conditioning videos really work). She doesn't know it, but I'm very happy that she's right on track. She's been watching bespoke sissy hypnosis videos for a while now, so many of the suggestions are planted and ready to bloom. That's even why she was sick earlier in the week. I make sure that my sissies keep themselves in good health, but a subliminal message in one of the files can make her think that she has the flu. And then the poor thing has to scramble to make enough points to escape her punishment. If you can't tell, I'm a little devious when it comes to trapping and training my sissies. This whole thing is part of my plan. The sissy fails enough and feels so bad that she starts begging me to punish her and make her into a better sissy slut. She is desperate for my approval. Every sissy goes through this and michelle is a little ahead of schedule. I punch up my camera and michelle immediately falls to her knees when she sees my cock appear on her monitor. "Master," she sobs, "I have failed You. Please allow me to prove that I am a good sissy slut. I'll do anything." I let that sink in for a minute before asking "Anything?" My cock twitches on cue, as if the words are coming directly from my groin. The sissy takes a deep breath before responding. "Anything," she promises, and then on her own accord comes up with a plan to prove her worth. "I need to be a better sissy slut," she cries. "100 points is not enough for me to prove that I am serious. I beg you to make me earn 200 sissy points a week from now on. I will work the glory hole every single night so that I can earn the points. I will post an ad on Craigslist begging men to come fuck me every single night. I will have them line up and breed me like a sissy cow that you will be proud of owning." I saw a new thought forming in her eyes. "200 isn't enough," she cried. "I'll do 250 sissy points this week, and 300 next month. Increase my total every week until my whole life is nothing a being a sissy bitch in heat, serving once cock after another." She raised her head and looked directly into the camera. "I promise," she said in a low voice, "I will never fail you again." I waited a minute before responding. I was jerking my cock on camera at the thought of how much fun we would be having as I accelerated michelle into year two ahead of schedule. "Done," I said as I shot my load and watched michelle mindless crawl forward to lick the computer screen, just in case any of the semen made it across the internet.

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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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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...

1 year ago
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Sissy Emma is turned

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

3 years ago
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My Sissy Schedule

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

1 year ago
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Forever Her Sissy Chapter 4 of 6

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

2 years ago
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The Sissy Contest

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

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

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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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

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

2 years ago
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A New Sissy Maid

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

1 year ago
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A New Sissy Maid

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

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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Classroom Sissy

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

4 years ago
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Sissy Velina

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

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Americas Next top Sissy part 5

Part 5 So Part 5 of my homage to 'America's Next Top Model' forced fem style lol ... hope you enjoy it and please comment. After a humiliating photo shoot the sissies wake up to another elimination. Jim felt better after a night's sleep, only to face wearing the overly feminine pink sissy dress he and the other sissies are forced to wear for the elimination. 'Getting eliminated, maybe that's the way out? At the very least I would get the satisfaction of denying these sick...

2 years ago
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Dr Cooks Sissy Clinic The Begining Jade and Deans Experience

Dr. Cook's Sissy Clinic: The Beginning and Jade and Dean's Experience. By dirteesissy I gazed at Jade's bottom, as she raped her husband's ass with a 10" strap on cock. Her pounding of her sissy maid's hole, bordered on the extreme, somewhere between love and hate, she punished that sissy ass with long powerful strokes. Jade, dressed in just red thigh high P.V.C. boots and gauntlets of the same material, was making mincemeat of her hubby's derriere and I looked on with pride at my...

1 year ago
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Cuckold Sissys First Meet Fantasy

This fantasy summary was sent to my wife and her prospective boyfriend to let her boyfriend know our fantasies and for me to know which bits got my wife and bf really wet? And feeling very horny? Which bits she really liked? And what they would you like to add to also?The text was sent to the prospective boyfriend's iphone with a picture of me on all fours showing my girlie soft pathetic knickered and caged boi-clit after he sent me a picky of his gorgeous cock which I had previously been lucky...

2 years ago
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I Want To Be A Sissy Part 1

Oh, my goodness! Today is going to be an exciting day. Mistress and I will find out if I can finally fill the C-cup brassiere she desires that I wear. I am so excited! A C-cup means so much to me. I adore my B's, the darling little girls, but a Sissy can be so much more of a Sissy when her cup size says WOMAN! As soon as I finish my morning toilette, Mistress will hook me into the cutest white underwire C-cup bra I have even seen and the moment will be here. I will fill the cups or...

2 years ago
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Andrew The Unsuspecting Sissy Part III

ANDREW THE UNSUSPECTING SISSY PART III [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 THUSFAR..... ANDREW NOW DREW: SISSY SUPERSTARSOON TO BE HUSBAND TO JIM JIM : BILLIONAIRE INDUSTRIAL 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 NEWMAN: MEDICAL DIRECTOR OF THE MANOR PENELOPE...

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...

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