Little Sissy Of Mistress (2). free porn video

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There he was in a barely covering Maid dress and in stockings. This was very humiliating for him but all this humiliation was making him excited and he was thinking what she wanted next.
“let’s complete the attire of this slut” Mistress said and motioned to open the second box. There were high heel sandals in the box and all pink in color.
“Put these on” Mistress said “and model for me”

The process was repeated again. All the sandals were ultra-high heels. He slipped couple of times as he had no practice in walking in high heels. Every time he slipped, he could hear the ladies giggling. He was feeling so ashamed. Finally Mistress zeroed in on 3 pairs of high heels including one he was wearing. He was waiting for direction of Mistress to remove the dress and change into his normal clothing but she did not say anything. Finally she spoke.

“Still not complete”

“Now what else is missing” he thought.

The lady motioned her assistant and the assistant slipped behind the door once again and emerged a few seconds later with a small box in her hand.
She came in front of him and opened the box. He was dumbfounded. He was looking at a big butt plug which looked like an inflatable type and was much bigger than what was currently in his ass, he could see nipple clamps and a chastity device. It also contained a pair of gloves and lubricant of some sort. Lets complete the attire of this slut” said Mistress, “ sweetie do what you are supposed to do” she said to the assistant.

The assistant slipped on the pair of gloves. She first took the nipple clamps. They had small bells attached to them. She attached one after the other to his nipples. Sharp stings ran through his body as the clamps bit into his flesh. Next she brought out the chastity device which was a steel cage. She fit it around his cock. It had a locking mechanism on top. After securing the cage she locked the cage with the small lock, walked over and handed the key to Mistress.

“Bend over” said Mistress and he did as directed.

He could feel the fingers of the girl fiddling with his asshole and the butt plug. She was turning it, twisting it, as she seemed to be enjoying it. Suddenly she yanked the butt plug out of his ass. He jumped with surprise as it took him completely off-guard. Almost immediately she inserted her fingers in his ass and kept them there, he felt fingers gently massaging his ass hole and stretching it. Then he felt something wet being applied to inside and outside of his asshole and suddenly he felt the plug being inserted into his ass. It was nothing like the one he had been wearing for past few days. It was filling to say the least. As he was getting adjusted to that plug inside his ass, he felt it growing in size as the girl started inflating it. She inflated to the extent it was uncomfortable and it was now impossible to remove it without deflating the plug. She then removed something and walked over to Mistress and handed over that to her. He could see that this was the pump attachment of the plug and without that the plug could not be deflated, so he was stuck with that as long as Mistress wanted. Suddenly he was feeling little scared but at the same time he was feeling very excited also. Now you see slut, your attire is complete. This is what you are wearing from now on.”

“Are You not forgetting something slut?” she said

He looked at Mistress, not sure what she meant.

“Don’t you have to say thank you to my friends, slut?”

“Yes Mistress, I am sorry”

“Thank You” he said to them.

“Well this is not what I meant” said Mistress

He looked at Mistress and then looked back. Both the ladies were naked from waist downwards and were sitting on the counter with legs spread.

“Go slut and say thank You to them, crawl, you are not allowed to walk” and he knew what he had to do.

He crawled over to the first lady, who was the owner of the shop and planted his lips over her waiting cunt. It felt very warm and juicy. He was feeling very aroused and excited and started lapping up the cunt like a dog. He could sense her arousal growing. She pulled him by his hair and pushed his mouth deep into her pussy to the extent that it was difficult for him to breath and then she climaxed and his mouth was filled with her juicy orgasm. He kept licking as she was still holding him by hair and then suddenly she pushed him. That was his signal to move to the other lady, who was the assistant. He started licking her pussy. This lady was more aggressive as she was pulling his hair, slapping him hard in the face as he was licking her pussy. Suddenly she pushed him on to the ground. There he was lying on the ground.

“open your mouth bitch, I want to ride it” he opened his mouth as commanded and immediately she sat on his face, plating her pussy on his mouth. She was pushing hard almost choking him, rubbing her pussy over his face. She was pulling on his nipple clamps which were very painful but he was too busy lapping up the pussy that he was not feeling that pain. Then she climaxed and warm orgasmic fluid was all over his face. Finally she got up.

“stay where you are slut” said Mistress. “Look at his face, such a mess, so dirty. It needs to be cleaned.” The two ladies perhaps knew what Mistress meant so each of them positioned themselves on either side of his face and suddenly he felt warm gush of pee coming out of both the pussies on his face. “ This will clean your face whore” said Mistress. When the ladies were finished they got up. “get on your fours whore” said Mistress. He got on his fours.

“What do you see?” said Mistress.

He looked on the floor, it was wet with mixture of pee and orgasmic fluid all around him. “It is wet Mistress” he said

“Well, that needs to be cleaned and you will clean it, USING YOUR TONGUE, so get on with it. He was way past hesitation. No matter how repulsive it was, he had to do it. So there he was cleaning the floor with his tongue like a dog. It took him almost 30 minutes before it was all cleaned. His back was hurting, his tongue was very sore. He wanted to go back home but knew that he was already past the point of no return.

He looked at Mistress for her approval.

“Good work whore, I think I can train you to be the perfect whore, Get up”

He got up. Put on your clothes. Whatever you are wearing remains. Keep your high heels on.

He complied as directed. The touch of fabric of his shirt with the clamps ran a painful sensation in his body. The clamps had made his nipples very sensitive. The butt plug was hurting like hell. The chastity cage was hurting his cock as it was not allowing it to be erect. He was not sure what was coming next. All this while Mistress had never even touched him but still he was feeling like he was under a spell and had to comply what was told.

Suddenly Mistress rose from the chair and walked towards the door. “Follow me” she said and he followed her. He was feeling ashamed to walk out of the door in heels but complied. Mistress got to her car and motioned him to get in the back seat. He climbed onto back seat wondering what was coming next.

The car moved a couple of blocks and entered a big double story house. The car pulled up in the parking. Mistress said “stay” and got out of the car. In about 10 minutes she came back. She opened the door and said. “ Remove these upper clothes whore, You don’t need these here anymore” He quickly glanced over to see if anybody else was in the yard and then immediately he felt a hard slap on his face. “What are you looking at whore?” the slap was so hard, it brought tears in is eyes. He immediately complied and removed his upper clothes. Here he was now sitting in the car with a slutty maid dress, clamps on his nipples, cage on his cock and butt plug in ass. As he looked at Mistress, she threw a collar towards him. It was also pink and had words “BITCH” affixed on it. Instinctively he knew what he had to do. He immediately put it on. Mistress said “You are a whore, a bitch and will be treated like one. Now crawl out of car” As he crawled out of the car, Mistress attached a leash to the collar. He was now being led into the house on fours and wearing a collar and leash. Mistress was walking very slow as if she was enjoying tormenting him. As they reached near the front door, Mistress tied the other end of the leash a pole and told him “stay here” and disappeared inside the house. He did not know what to do. Here he was in such a shameful state tied on the front door of a house like a bitch. He was dying of shame. What if anybody walks in from the gate? He was feeling so humiliated but at same time he was feeling very aroused.

Mistress was gone for about 30 minutes after which she emerged from the house, unhooked his leash from the pole and led him outside the house, around the house towards the backside of the house. She opened a door and led him inside. The room seemed to be prepared for the BDSM play. It had all the tools he could think and many more. Crops, whips, paddles, chains, whatever he could think of, was there. There was a bed also in the room which looked like to have been prepared for sole purpose of BDSM play. Leaving him in the middle of the room, Mistress walked over to a cupboard and brought out something. What it was he could not tell. She came behind him, held his chastity cage and slipped some tube sort of thing in the cage. He could feel coldness of some metal but what it was he could not tell as he was afraid to look back. The Mistress came forward in front of him and said Bitch, do you know what I have attached to your cage?”

he replied “No Mistress”

“I am sure you are eager to please me and are willing to do what I say”

“Yes Mistress”

“But I do not want you to spoil the fun because if you hesitate then you are useless for me and I have just the thing which will ensure that you cannot even think of defying me and have no option but to comply” she said and held out something which looked like a small transmitter with a small antenna. She pressed a button on it and suddenly he felt a jolt of electricity in his groin area, it was powerful to say the least. It just took his breath away for a second as he was not expecting anything like this. She turned a knob on the transmitter and pressed the button again which resulted in a more powerful jolt which made him almost jump. This shock was very uncomfortable to say the least and then she turned the knob all the way and looking at him she pressed the button again. this jolt was now too much of him and because of it he almost doubled over but the pulses did not stop. He was feeling strong pulses almost every half a second. His mind went blank. He was reeling on the floor in pain but that did not seem to affect Mistress. This went on for a minute and then suddenly it stopped. It was such a huge relief but he felt totally exhausted and drained. This was a nightmare and he knew that he would do anything to avoid these shocks again.

“I believe Bitch, now you know what will happen if you do not comply” Yes Mistress” he replied, trying to catch his breath.

At this point Mistress said “be on your fours Bitch” and he immediately complied. Mistress walked to his rear. He felt a hand gently caressing his ass. It felt soothing, it felt good. He felt the hand gently caressing for some time and heard Mistress say “Whore, you want to be my Bitch, right?”

“Yes Mistress”

“You will do as I say, you are my mindless Bimbo, right?”

“Yes Mistress”

“You are losing your authority to question your Mistress by your own will, right?”

“Yes Mistress”

“You are ready to be a slut, a whore for your Mistress, whose only objective is to please Mistress, whatever she desires, However depraved it may be. You will do it for pleasure of Your Mistress, right?”

“Yes Mistress”

“Whore, I know that serving pleases you, that is why you are here, but, I believe you know that anything you want, anything you desire always comes after my pleasure”

“Yes Mistress”

“My pleasure is foremost and you are never to question the ability of your Mistress, with an understanding that Mistress will push you far beyond your limits but will never put you in danger. Do You understand that”

“Yes Mistress”

“Do You trust your Mistress”

“Yes Mistress”

“Good, you seem likely to develop into a good whore”

That is what he wanted to hear, that is what he wanted to be. Immediately he felt a very hard spank on his ass which nearly took the wind out of him, but he clenched his teeth, ensuring that he did not cry out. But that was just the beginning. One after the another many spanks followed, one harder than the other. His ass was like on fire, and then he felt the caressing again, which felt very soothing. He felt the other hand caressing his balls, which had not been involved in the play until now. He felt the hand squeezing his balls. It was so hard that he let out a shriek. Almost immediately he felt the electricity jolt through his lower half as well as a very hard spank on his ass. He knew immediately that he was not supposed to do that and clenched his teeth hard. Mistress kept pulling and squeezing his balls and caressing his ass with other hand. Then he felt a rope being tied to his balls.

“I am attaching rope to your useless balls. I will attach weights to the other ends, it should stretch your nuts really nice and at least they will become of some use for my amusement.

“I am going to remove your butt plug and it will be replaced by something else. Stay where You are and move your head down and ass as high up in the air as you can”

He wanted to ask what Mistress was going to do, but, he dared not ask so he did as asked.

Mistress attached the pump to the plug and deflated it. As it was deflated, it felt good and he felt relieved but that relief was short lived as he felt another object being inserted into his ass which also seemed like a butt plug. It was bigger than before. Mistress walked in front of him, she was holding a high chair which she kept in front of him and sat on a high chair. “Look at me” she said. The chair was quite high and he was in a position where his face was on ground and ass was high up in air so he had to put a lot of strain to be able to watch Mistress.

He could see that the chair had a hole in center with a bowl attached to the hole. At the bottom of the bowl there was a tube attached which was disappearing somewhere behind his back, where he could not tell. He was perplexed as to what was happening. Suddenly Mistress rose up. Her face had no expression. She removed her pants. He could see Mistress was now naked from wait down. “I have drunk lot of water and need to relieve myself, but it is precious so it is not to be wasted. He could not understand what was going on and was perplexed. Mistress sat on the chair and the pee started flowing from her vagina into the bowl beneath the chair and from the bowl it started going through the tube. Almost at that time he felt a warm liquid filling his bowels and he suddenly understood. The tube was attached to something in his ass and that liquid was coming out of vagina of Mistress going straight inside his ass. It was much to say the least. He was feeling all full and the reaction of his bowls was to push the liquid out, but because of the butt plug it did not come out and kept filling him. As Mistress finished she rose up, walked behind him. She removed the tube and replaced it with air pump. He felt the plug expanding; it was becoming a very intense experience for him. The pressure of liquid inside and the fullness of the plug were very intense. It was inflated to the point, where he felt that it was nearly unbearable. May be Mistress also understood and stopped. She removed the pump, walked in front of him and twisted his clamps hard which brought tears in his eyes as the pain was too much. Continuously twisting them she said” Now You will hold this liquid and the plug will hold it in place and keep your ass stretched until I want to put it to another use. Keep on ground with your head down”. Mistress left him in this state and walked out of the room. He was wondering what was coming next for him.

In this state, he had almost lost sense of time. He may have stayed in this state for may be about 2 hours. The pressure in his ass was immense, the clamps were paining but he somehow was feeling content, after all this what he was looking for, may be not exactly in the way the things had turned out but nevertheless he was living his fantasy.

He heard the sound of heels, it must be Mistress he thought but he was very afraid to look. The footsteps came near him and stopped. There was no sound for few seconds which made him kind of nervous. He dared to move his head and suddenly he felt that strong shock in his guts again which made him double over in pain. The shocks were continuous and suddenly he felt a sharp string on his ass, it was very hard and continuous. He was in pain and cried out but neither the shocks stopped, nor the lashes on the ass stopped. Somehow instinctively he got back on fours and the lashes stopped, but the pain from shocks made him double over again. As soon as he fell on ground, the lashes started again and this time harder than before. He understood and got back in position and the lashes stopped.

The mild shocks continued. He understood he had to be in that position and bear the sting of shocks. It was very difficult but fear of lashes kept him in position. Mistress came in front of him. She did not say anything. She took the leash in her hand and started walking. He understood that he had to crawl after her. As he started crawling, he felt a jolt on his balls and suddenly he remembered, Mistress had attached weights to balls. They were heavy, it was very difficult to pull and the pressure on his balls was tremendous. He could not keep pace with Mistress and the leash was pulled out of hand of Mistress. As soon as that happened, his heart sank as he knew he was in trouble. Mistress did not say anything. She walked behind him and suddenly he felt as if someone had yanked his balls very hard. He cried out in pain “I am sorry Mistress, please forgive me” but the yanking did not stop and in addition to that the lashes started hitting his ass very hard. This all brought his heart in his mouth. He was crying loud, begging for mercy but Mistress would have none of it and then she spoke “You pathetic worm, How dare You?” The yanking did not stop, neither did the lashes.

He could feel the welts appearing on his legs, his ass, his whole back. His whole backside was in pain but Mistress did not seem to care and then it stopped. She walked again and held the leash. This time he was more than eager. As Mistress walked, he pulled hard on the weights, it stretched his balls to the point of very painful but he knew he had no option. He pulled with all his might and was able to match steps of Mistress. His balls were aching, they were stretched to maximum but he was crawling, led by Mistress on the leash and pulling the weights. Part 3 loading...

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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,...

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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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,...

2 years ago
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  • 27
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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,...

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