Little Sissy Of Mistress (5). free porn video

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He was being ravaged and violated as rough as it could be and then suddenly he felt a dick knocking on his ass hole. He panicked as it forced his ass hole open. It was very big to say the least which felt as if it had torn his ass hole apart. He wanted to protest but his mouth was full of another monster dick. And then that dick forced his way inside his hole and started thrusting very wildly. He was being violated from both the sides now and they seemed to move in rhythm, one more vigorous and rough than other. This went on for almost 15-20 minutes and then the thrusting started getting more vigorous as the guys were nearing climax. And then suddenly the first guys shove entire length of his cock in his throat and stated shooting his cum. He was choking with the cum but was held tightly so he could not move, at the same time he felt the other guys shooting his cum deep inside his ass as entire 9 inches of that cock was buried deep into his ass. Both of the cocks emptied themselves deep inside his both the ends and withdrew. He was panting and gasping for breath but almost immediately his both ends were stuffed again with almost same size cocks and ravaging started again.

The guy fucking his ass was spanking him hard, really hard and the guy fucking his throat was slapping him hard and abusing him. He was feeling too exhausted to even react. After some time the guys switched places, the guy fucking his ass started fucking his throat and vice versa. After another round of about 20-25 minutes of abusing, they shot their cum in his both ends. As soon as they withdrew, another set of cocks replaced them. He was gasping for breath but was helpless. He was feeling as if he was in seventh heaven. This went on for almost more than three hours and in these three hours both his mouth and ass had been constantly violated. He was too sore from both ends but no one was having any pity on him. As he felt that all of the guys had cum and this was over. He saw a guy lying on his back on the bench. His dick was huge, almost 11 inches and very thick. It was pointing straight upwards as he was stroking it. This sight was very fearful and he got very scared. Suddenly two pairs of hands yanked him out of his spot and carried him near that guy. They placed him atop that man and positioned his cock on the entry of his ass hole. As they pushed him down on the cock, he felt as if a rod of molten lava had entered his ass, but surprisingly looking at the size of cock, still it was an easy entry. Hours of continuous fucking had made his ass hole so loose that it could take this enormous cock so easily.

One guy started whipping his back and commanded “bounce on this cock, bitch. Fuck your ass hole” as he started doing that, another guy position his dick in front of his mouth and forced his dick inside his mouth and started face fucking him. He was joined by 3 more guys, no sooner one guys took his dick out, immediately another dick took his place, at times he was being forced to suck two dicks at same time while being slapped hard in face by one guy, the other guy would be pulling his hair while someone was also pulling his ears, all the while the whipping never stopped.

He was sitting on that enormous cock and fucking it all the while sucking the cocks, suddenly one of the guys fucking his throat pushed his head down which caused his ass to move up and the guy fucking his ass adjusted his cock accordingly but did not let his cock pop out of the ass. As he was being deep throated, he felt tip of another cock on his asshole while the first one was still in his ass. He panicked and tried to move but he was held so tightly that he could not move an inch.

The second dick applied some force which made him cry out but that resulted in the cock in his mouth going deeper and then suddenly the second cock also gained entry in his asshole. Now his asshole was being fucked by two giant cocks that started vigorously thrusting inside his ass. The guy fucking his mouth withdrew and immediately was replaced by another cock and then one more cock. This bitch was now being fucked by two cocks at both the ends. He felt his asshole and mouth being stretched to maximum but there was nothing he could do as they kept violating his ends. Both of the dicks in his mouth climaxed with him drinking all the cum and almost simultaneously both the dicks in his ass also climaxed. As soon as they withdrew, he was carried and made to sit on another big dick and almost immediately he was pushed down as second cock entered his asshole. This process was repeated with his mouth also. They kept spanking his ass, slapping him and fucking his both ends for almost 20-25 minutes and then climaxed and immediately were replaced by another set of cocks at both the ends. He was now too shocked to even react but despite in being such pain, humiliation, something inside him seemed to enjoy all this. “what is happening to me” he asked himself but he did not care, he was just flowing with the tide. This double fucking went on for another 2 hours. He could feel that his ass hole had become very lose as despite his trying the lips of his ass were far apart leaving a big gape. The guys dressed up and left one by one while he lay on his back totally exhausted. This evening a bucket full of cum had been deposited in his both ends. He had been violated like never before. Cum was oozing out of his ass and depositing on floor.
As he lay exhausted, Mistress walked up to him and waited until the cum stopped dripping from his gaping ass hole and then said “bitch, take your position. Though he was exhausted, he could not dare to defy her so he immediately got on fours.

Mistress dragged him back until the cum which had oozed out of his ass hole was in front of his mouth and almost instinctively he knew what he was supposed to do. He started licking the cum out of floor. There was no more hesitation left in him. He was way past that. As he was lapping up the cum from floor, Mistress walked towards his back and said “ Slut all this fucking has turned your tight cunt into an impressive gaping hole, that is what suits a whore like you” as she started caressing his ass cheeks. She pushed 2 figures in his hole, then three and then four. She said “see slut your cunt can take all my fingers.” He did not say anything as he was busy licking cum of the floor.

Then he suddenly felt the whole hand up his ass hole. Mistress said “Whore, your cunt can take my entire wrist, that’s impressive” and she started fucking his ass hole with her hand and also pulling on his balls. He was feeling pain but more than the pain, he was feeling ecstatic. All what was happening was way beyond even his wildest dreams. He had secret fantasies but tonight Mistress had shown to him how shameless a slut he was, a slut with no boundaries. As he had the chances to move away but he decided to stay and endure all this and some part of him was very glad that he chose to stay. As he was still busy licking the cum and Mistress was fucking his ass with her hand, he was thinking of what could be next as this was still the first day of his slavery. He felt Mistress withdrawing her hand from his ass. She came in front of him and signaled towards her gloves covered hand which she had just withdrawn from his ass. Instinctively he started licking the gloves which had traces of cum deposited earlier in his ass hole. He thoroughly licked it clean. By the time he realized that Mistress was wearing a giant pink Strap on which was bigger than anything he had seen before. Even the big and thick cocks which had abused him that night would seem very small. It was at least twice the diameter of the thickest cock which had fucked him so far.

Mistress held him by his hair and shoved the cock in his mouth. It brought his mouth almost to breaking point. Mistress was fucking his mouth, shoving it in. forcing him to take it deep. He was gasping for breath but Mistress would have none of it and then suddenly she let go of him. He saw she was holding a giant ball gag in her hand. It was pink in color. Pink had almost become synonymous with Mistress. She clasped his nostrils which blocked his breathing and he had to open his mouth for air. No sooner he opened the mouth; Mistress shoved the ball gag in his mouth. It had leather straps which went round the face and closed at the back of head. She tied it very tight leaving his mouth full of the gag and this also made sure that no sound will come out of his mouth. He saw her walk up to the table and return with a big leather paddle. She walked behind him and almost immediately he felt a strong swat on his ass cheeks. This single one was harder than any spank he had received so far. This made him cry out in absolute pain but his voice was muffed because of the gag. Tears started rolling out of his eyes. The swats continued, each harder than the other. He was crying out in pain. He felt as if his ass was on fire. With each swat he felt as if he will pass out and then it stopped. He felt her hand caressing his burning ass cheeks and then suddenly he felt that giant strap-on enter his ass. His asshole was no doubt quite loose because of all the battering, but, this was Big. He cried out in pain and tried to move his ass away but was immediately silenced by hard spank on his ass and twisting of his balls. Mistress started fucking his ass in a rhythmic motion but very hard nevertheless. This was probably the wildest and most rough fucking of them all. The strap on had stretched his ass too much. Even the two dicks in ass would seem nothing against the pounding he was receiving from this giant strap on. She fucked his ass for close to thirty minutes and that thirty minute fucking was as hard as anyone could imagine and then she withdrew from his ass leaving him gasping and panting.

Mistress came in front of him, removed the gloves and then with one hand lifted his chin up and with her other hand started caressing his hair. Already beaten and battered over the events of the night, he almost melted in her hands. Tears started running down his cheeks. Saliva was drooling from his mouth from the sides of the gag. Mistress removed the ball gag from his mouth and kissed him on lips. She kept caressing his hair, moving her long fingers through his disheveled hair. She said very lovingly “You have suffered a lot for my pleasure tonight. Haven’t You?” He looked at Mistress with tears running down his cheeks but said nothing. Mistress kissed him again on his lips and said “But this is what you really wanted. Didn’t you?” he nodded. I gave you chances to walk away, but you did not, which shows this really where you wanted to be”
He nodded again. She once again kissed him on lips, this time more fuller and longer and then said “Now listen to me very carefully. I see that you have suffered a lot. If you feel that this is not where you intended to be, you are free to go now. I will not be angry at all. If you want to go, you are free to go without any fear of reprimand. Think about it and let me know”


As she got up to walk away, he latched on to her leg all the while crying profusely and said “Mistress, please don’t ask me to walk away. I do not want to go. I beg You, please humiliate me as much as You want, please beat me as much as You want but I beg You, please don’t ask me to leave. I cannot walk away now. I do not want to walk away now. I am ready to serve you in any way you want, but, please don’t abandon me. I beg you”


As he looked up, he saw that Mistress was smiling. She said “alright. So be it if this is you want. Now there is a bathroom towards your right. No need to crawl, you may walk if you want to. Go and take bath and come back” He started moving towards the bath room, but, instead of walking, the option which was given by Mistress, he was crawling on fours as if he did not know how to walk. It was not that she was not concerned for him. She wanted to push his limits to see how far he could go but his compliance and eagerness had her push the limits further. There were quite a few times where she was genuinely concerned about his safety but was surprised to see that he could take it all. This had convinced her that this slave had a great potential. She could feel that she had also started liking him very much. As she saw him walking towards the bathroom, she sat back in chair, content with the events of the day so far. As he was going towards bathroom, Mistress was smiling. She did not intend to repeat this intense torture anymore; this was to test the capacity of her new slave, willingness and devotion of her new slave. She was content; she knew this slave was not going anywhere. He was hers for keeps now. He was her sissy slut, her own sissy slut. The End.

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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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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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