Online Sissy Training free porn video

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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 after week after week." I gulped. It was all true, but responses to my ads always went to a private Gmail account. This one had landed in my work email, and my company definitely scans our correspondence for inappropriate content. Nevertheless, I continued reading. I didn't seem to have a choice. "I would like to offer my services," the email continued. "I have taken great pleasure in turning several sexually frustrated sissies, like yourself, into cock-crazed whores. I think that you show great potential, and I would like to add you to my stable of sissy sluts." "If you are serious about finally acting on you sissy cum slut fantasies, then please contact me, and we shall begin your training." "Sincerely yours; Master David." I couldn't delete the email fast enough. I purged it from my system and prayed that IT didn't flag it. Although, in my sissy heart, I was hard as a rock thinking that I had finally found a real Master who would make all of my kinky sissy dreams come true. Well, as hard as I could get while locked in my chastity. I spent the rest of the morning throbbing in my panties thinking about what could have been. An hour later, I got another email. "Hello Sissy; I am waiting to hear back from you. As I mentioned earlier, I am fully prepared to turn you into the biggest sissy cum dump in town. When I am through training you, I promise that there will be a line of men who will be waiting every day at..." and he wrote out my home address, including the zip code and a Google map link to my house. I didn't read the rest. I deleted the email, and I purged my deleted folder for good measure. My heart was beating in my chest, and it didn't stop pounding for the next 30 minutes. Which is when the next email arrived. "Hello SISSY SLUT;" it read. "I am sending these emails to your work account because I know your IT department scans them, so they will be on the lookout for words like SISSY, CUM DUMP, FUCK SLUT, KID PORN, DOG FUCKER and so forth." And of course, they will automatically scan for any pornographic pictures, like the one I have attached here. I have collected several photos from your various accounts. I will start sending all of them to your work email if you don't respond within the next 60 seconds." And then my phone buzzed. I had received a text. It said "60." I was panicked. I grabbed for my phone and wrote back "Hello." The phone buzzed back with "45." I wasn't sure what Master David was looking for. I replied to my email. "Hello," I wrote. "What do you want?" My phone buzzed again with "That's not how you address your new Master, sissy." And then, "30." It was followed by a picture of me dressed up and sucking on a dildo from my Fetlife account. I started typing again. "I apologize Master. This is sissy slut Michelle and I thank you for agreeing to train me to be your sissy cum dump. I will do what you command me to do." My phone buzzed once again. "Good slut," it read. "Let's begin." Master David then proceeded to text me every one of the pictures that I had posted on my various online profiles. Every single one of them was watermarked with my name, phone number, email address and home address. "As you can see, sissy," he wrote, "I have collected all of your sissy photos and could absolutely destroy your life if I wanted to do so. Fortunately for you, I am a benevolent Master. I only want to help you become the sissy slut your truly are inside, and as long as you follow my orders, I won't need to expose you to your friends and family." He then proceeded to email me a list of my personal contacts, which included contact details for my boss, my brother and sister as well as my mother. I immediately texted him back. "Please, Sir. I will be a good sissy slut and do as you command." "Good sissy," he wrote back. "Wait for my instructions." And then he was gone. Needless to say, I didn't get any work done for the rest of the day, and I flinched every time the phone rang, thinking that it was IT calling to discuss my emails, or my mom calling to ask me about why her son was now a depraved sissy slut. It scared me to death. It also was super hot, and I was as horny as I have been in months thinking about what was on the horizon for me. At one point I realized that I was shaking with fear. My boss even asked if I was okay. I mumbled something about feeling poorly and decided to take a sick day. No sooner had I logged off of my work station than I received another text from my new Master. "Sissy," it read. "I will require several pictures every day that prove you are being an obedient sissy slut. Write today's date on a post it note, along with the words, 'sissy's pathetic clitty.' Then go to the restroom and take a picture that shows your sissy clitty--because we all know that it's certainly not a cock." "If you are true to your posts, I will expect to see your clitty locked in its cage and surrounded by some pretty panties. You will be punished if this is not the case. You have five minutes to send the picture." I practically ran to the restroom. I was wearing panties (I haven't worn anything else for almost a decade) and I did happen to be locked in my Jailbird chastity cage. I was so happy that I didn't let myself out last night, even though I had wanted to free myself for a quick jerk off session. For whatever reason, I had decided to stay locked up, and I was now very happy that I had done so. I sent the picture within 3 minutes and was rewarded with a text that read, "Good sissy. What time do you get off work?" I responded immediately. "I am usually home by 6, but have decided to take the rest of the day off." The reply text was immediate, and the beep from my cell phone was loud enough to make my heart skip a beat. "Good." It read. "Text me when you are home and naked and ready to begin your training." 20 minutes later I did as I was commanded. Master David demanded proof that I was home, and I texted him a picture that showed me standing naked, other than my panties and chastity cage. He then began to ask me all sort of questions. Did I have any current boyfriends? How many men did I serve on a daily basis? Was I taking hormones? What was the status of my sissy wardrobe? Was I very passable? What was I doing to lose weight? Was I an accomplished cocksucker? Did I have any kinks that I wanted to explore? His questions went on for almost an hour. I was still scared shitless, but I did my best to answer them all, like a good sissy slut would do for her Master. And, as per Master's instructions, I went to my toy chest and took out my biggest dildo. I quickly found myself bouncing up and down on the monster cock as I answered his questions. When he asked me to turn on my webcam, I did so without any hesitation. Master chastised me for not having any makeup on, I immediately excused myself and went to put my face on. I returned 30 minutes later fully dolled up with makeup, wig, dress and high heels. Master wrote back, "Good Sissy," and told me to get down on my knees and practice sucking on my dildo for the webcam for the next 30 minutes. I balked for a second, as the dildo had just been in my ass, but I decided that I had better do as I was instructed. The dildo had a suction cup base. I mounted it on the wall and proceeded to do my deep throat exercises for the webcam while Master watched from afar. Thirty minutes later, Master emailed me a link. It was my new Craigslist ad. It read, "Please help me train my new sissy cum dump." "I have recently acquired a new sissy slut, but I will require a small group of men who are willing to help train her to be a complete sissy cum dump. I will need a few men to stop by in the early morning, and a few more during the lunch hour. She gets home every night around six, so we'll need a few guys looking for a post work suck and fuck, and then some more who want to stop by late at night to feed her a midnight snack." "Each time you show up, you'll find her tied up and locked in a chastity and willing to serve you like a total sissy slut. All I ask of you is that you send me a picture EVERY SINGLE TIME that shows my sissy slut's mouth or ass stuffed full of cock or splattered with cum. I will be posting these pictures to her sissy Tumblr account." "If this piques your interest, and if you are okay with fucking this sissy slut when other men are present, because Lord knows that there will be a line of hard cocks lining up to breed this sissy, then let me know that you are okay with this." "Also," in ended ominously, "if you have any kinky fantasies that you want to explore, let me know. Water-sports, electro-sex, bondage, bestiality, you name it. The good thing about training a sissy slut is that she will do whatever you demand, whenever you are horny." And then he sent me a few of the responses. Master told me that there were already twenty men champing at the bit to use me, although it was early and he expected at least thirty more. My doorbell rang. Master texted me, ordering me to answer the door. He seemed to sense my hesitation. "Answer the door now, slut," he wrote, "Or I will fuck up your life for real!" I knew in my heart that he was serious. I opened the door. There was a young guy standing there, and he broke into a leer when he saw me. "So, you're the sissy slut who needs to be trained," he said as he walked into my house, grabbing my neck as he passed and shoving me to the ground. "Well?" he said, "Get to it." I did as I was told. I unzipped his pants, with my teeth as instructed, and fished out his cock. I did my best to suck him off, but at a certain point he just pulled it out and finished himself off, splashing his cum across my face. "Smile for the camera," he said, as he took a picture that showed my face plastered with his cum. Almost immediately, the doorbell rang. He dragged me to the door and told me to open it, even though his cum was still dripping down my face. I did as I was told and found two black guys standing there. They were quickly ushered inside. Within minutes I was being spit-roasted while the first guy stuck around to make sure and document everything with my cell phone camera. I was impaled on both ends with hard cocks when two more guys stopped by to help train me. I'd just started my sissy training and I already had five guys in my apartment. I kind of lost myself in a cock lust haze and did my best to serve whatever cock was presented to me. I know that each one of them came more than once, and that a few other guys stopped by before I was carried to my bedroom and one of the guys pulled out a roll of duct tape. He proceeded to bind me up, ankle to neck, with the duct tape. I was thrown onto my bed, with cum leaking from my sissy holes, and told to try to get some sleep as my next sissy cock trainer would be here at 5am. The man turned my phone on to a sissy hypnosis loop and put my headphones on me. I drifted off to sleep listening to a non-stop loop of the sounds of fucking while some sissy chanted a sissy sub mantra. "I am a sissy slut." The mantra chanted. "I live to serve cock. I exist only to make horny men happy by slurping down their yummy cummy. I am a sissy cum dump. I am two holes that need to be filled by hard cocks and cum. I am only as good as the number of men who use me on a daily basis." I was exhausted, and even though I was mummified in an uncomfortable position, I still managed to fall asleep, with this mantra looping on repeat all night long. I woke at 5am when somebody suddenly shoved his cock down my throat. I was still tied up, so I couldn't do anything other than have my face fucked. He came and flooded my belly with his cum. Then he pulled out a knife and cut open the duct tape so I could move. He dragged me to my bathroom and shoved me into the tub. Then he proceeded to shower me with his piss, all the while demanding that I open my mouth and swallow it while he took pictures on my phone. Another man walked in at this point and whipped out his dick. He shoved it in my mouth and proceeded to fuck my face while he also unloaded his morning piss down my throat. I couldn't take any more. I vomited. But that didn't stop my morning trainers. They simply flipped me over and began pounding my ass, and filling my bowels up with their piss until I felt like I would burst. That made them hard. After they came in my ass, they turned on the shower (as cold as it could get) and left me there in the tub, saying that they would see me tomorrow, and that they expected me to do better then. I lay under the cold water a several minutes, ultimately pulling the tape off of me. I turned the tap to warm and stood swaying in the tub when somebody walked into my bathroom. Another black guy. He was huge! His cock must have been at least ten inches in length, and honestly, I was excited to be used by such a magnificent cock! It's a good thing that I had been well stretched out as he dragged me sopping wet from the shower and plunged his cock into my sissy pussy without any warning. I cried out in pain. He didn't care. He fucked me mercilessly and flooded my pussy with his cum. Snap. He took a picture on my phone. Just before he left he told me that I had to go to the store and buy some tampons, so that I could keep his cum from dripping out into my panties during the day. I was so stretched out that I thought that I would need several tampons from here on out. My phone rang just before he left. It was my online Master, saying that I had been a good sissy slut on my first day, although I would need to work harder on my sissy cocksucking skills. Not to worry, he would make sure that I got lots of practice each and every day from here on out. He sent me the link to a sissy Tumblr page, my sissy Tumblr page that had been populated with twenty-three pictures that showed me sucking cock and being fucked and splattered with cum. All of the pictures had my name, phone number, email address and home address written across the bottom. This was the first time that I started to worry about what was happening. I started to wonder if I should just say fuck it and try to reclaim my life. Not sure how, but Master might have sensed my uncertainty. He sent me another text. "Good start, sissy," it said. "I hope that you are having fun. I know that I am. It will only get harder from here on out. And God help you if you ever disobey me, because I have everything I need to destroy you." I gulped and responded. "Yes, Master, I will obey like a good sissy slut." I went to work, but not before sending Master a picture that showed my caged clitty in my pretty panties, and a massive butt plug shoved deep in my ass. I was also wearing a cami and stockings under my boy clothes. I punched in at 8 and immediately received a text instructed me to run to the bathroom and prove that I was still caged and plugged. I did as instructed, adding the Post it with today's date and the words "Sissy Birth." All morning long I received texts from the men who had used me last night. They were all accompanied by pictures of my sissy depravity, as well as demand that I show them my clitty or ass in pictures form, and a message saying that they were looking forward to using me again as soon as I got off work. I didn't get anything done at work. It seemed like every 15 minutes I had to excuse myself and run to the bathroom to take a picture to satisfy one of my sissy trainers. I suppose that it should have freaked me out, but I must honestly admit that my sissy clitty was throbbing non-stop inside my chastity device. And then I got a phone call from our Engineering department. It was IT. I knew that I was fucked. I walked down the hall, certain that I was about to be fired. Sure enough, our IT guy told me to come in and close the door. He had seen the emails, and wanted to know what was going on. I was speechless. He surprised me by asking point blank if I was a sissy slut? I gulped and answered, "Yes." He smiled and said that everything was okay, but that I should strip and slip under his desk and start sucking his cock. I was so relieved that I did as instructed, and soon found myself stuffed under his desk with his cock stuffed down my throat. It was the first day of what would become my daily ritual. I now log in and head immediately to the IT department. I now have a key, so I just let myself in and tie myself up under his desk. The engineers usually show up an hour or so later and sit there, going over their emails while I lovingly slurp down their cocks. It caused some problems at first when I received texts from my trainers demanding pictures of me in my sissy slut mode. Fortunately, the IT guy was more than willing to send pictures of me stuffed under his desk, my mouth stuffed full of his cock, with a message saying that I was busy being a sissy slut right now, but that I would be free to respond in an hour or so. That's my life now. I wake every morning at 4am and give myself an enema so that I am always squeaky clean and ready to service any of my sissy trainers during the day. I move to my living room and le down over my coffee table while I play a sissy slut hypnosis file on my iPhone. I am always roused from my sissy slut hypnosis dreams by somebody stopping by to feed me my sissy slut breakfast of hard cock and cum. There are usually three or four men each morning. Some days it is as much as six. It doesn't matter to me. I will suck and be fucked by every cock that shows up at my apartment. I Send a quick picture to Master that shows how I will be dressed during the day, as well as another that shows my weight (I have to lose 5 lbs every week). Then I run off to work. I punch in and immediately head off to the IT department, where I spend an hour or so under their desks. Then it's five or six pictures for my sissy trainers before heading home for lunch. There is always a line of men cued up at my house, waiting to use me when I get home for lunch. I seldom get to eat anything--that's okay as my stomach is generally filled full of cum by the time I head back to work. They have also taken to giving me my daily sissy hormone shot. After a few months, it's hard to hide my budding breasts. Plus, with my forced sissy diet and being locked constantly in corsets or wait trainers, I have been developing a pretty sexy sissy figure. One of my trainers has taken to showing up at my work in the early afternoons and demanding that I accompany him to his car. I crouch down in the passenger seat and do my best to serve him while he drives around town. Once he has filled my belly full of his cum, he takes me back to work. By the time five o'clock rolls around, I am always the first one out the door. Some times there is somebody waiting to drive me home (and use me like a sissy slut along the way) but most nights I simply rush home and plop myself into the tub where I give myself a quick body shave and get ready for the horny men who will be showing up at my apartment. By now they all have keys to my front door, so there's nothing I can do to stop them. They simply walk in, force me to my knees, fuck me, tie me up and then leave me so that I am always ready to serve the next hard cock that walks in my door. I'm not quite sure, but it appears that I am serving 27 men at this point, with 12 of them using me on a daily basis on average. Master says that he is very pleased. It has been more than six months. He now has more than 1500 pictures that show me acting as a complete sissy slut. He plays his final card. He sends a photo of me sucking off the head of IT to my boss. She immediately demands that I come to her office. I know that I will be fired, so I don't bother to go into work. He also sends a picture to my mother, making sure that she knows that her son is now a submissive sissy slut. By now I have obvious breasts, and I have been trained to be such a depraved cock slut that there is now doubt as to what I have become. He also sends an anonymous email to my landlord, alleging that I am running a sissy prostitution ring out of my apartment. I am immediately served with an eviction notice. And if that's not enough, it turns out that one of my sissy trainers has maxed out my credit cards, signing me up for some expensive travel adventures. Which is how I found myself tied up in a wooden crate, loaded onto a ship and sailing across the sea to a Master who was looking to find a sissy slut for his own personal use in Germany. What happens next? I cannot say. Hopefully, I will be a bigger sissy slut in the future. I know now that this is what I was put on earth to be.

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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...

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,...

4 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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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...

2 years 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...

2 years 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...

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...

2 years 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...

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