Jimmy's Sissy, Part 1 free porn video

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"Alright, faggot. Wake up! I'm not leaving until you make my dick cum." That was the sound that reverberated around my freshman dorm room the night that my...let's call them troubles...the night that my troubles began. While not the absolute beginning, it was the point where there became only one possible ending. You see, there was a time when I wasn't a cock sucking sissy addict. That was the time before Jimmy, my high school bully, drunkenly barged into my dorm room with the urge to embarrass me by trying to make me make him cum. There were a lot of things that could have gone differently that wouldn't have ended with me begging Jimmy to suck his cock on a daily basis. I could have stood up to Jimmy that first time that he tried taking my lunch or any of the other 500 times that he fucked with me in high school. My high school guidance counselor could have told Jimmy that the information was confidential when Jimmy asked him what colleges I had applied to. He could have done the same when Jimmy later asked where I had been accepted, and he could have done it again when Jimmy asked the counselor where I had decided to attend. Instead of going to UW-Madison, I could have gone to Vasser where Jimmy hadn't been accepted. My freshman roommate could have sought tutoring help instead of failing all of his classes the first semester and subsequently dropping out, leaving me with a dorm room all to myself. I could have told Jimmy to go fuck himself when he barged in demanding my services. All of those things did happen and when Jimmy came into my room, he used that voice that he had perfected over the course of high school. That voice that instantly makes me cower and want, nay, need to be subservient.
So the only thing that could occur at that point did occur: I got out of bed with my head hung low, slinked over to Jimmy, unzipped his zipper, pulled down his pants and underwear, took his slightly larger-than-average cock in my hands and started stroking it. He shivered with what I think was surprise; shock and surprise that he still held sway over me and a realization that he could make me do anything. After a minute of this, he started in with the verbal abuse. "Holy shit, you really are a faggot. Were you always a faggot or did all of those years of me calling you a faggot convert you? How many men have you jerked off? None?!? I don't believe that, faggot. I bet you let thick Mr. Dresch fuck you in the ass. I bet I could drive a bus up your loose faggot ass." Mr. Dresch was our gym teacher and used to shower with the boys in his 6th period class. Guess who was in Mr. Dresch's 6th period class: me and Jimmy. Once, Jimmy caught me looking at Mr. Dresch's cock, which was fucking huge; it was like two coke cans stacked on top of one another. Jimmy then started all kinds of rumors about me and Mr. Dresch.
"Hey, faggot! What are you doing? Keep jerking me off." I had drifted off into memories of showering after high school gym class. I looked down and there was Jimmy's hard cock in my hand. Jimmy then said, "You know what? I'm tired of this handjob. They're fucking worthless." He then started rubbing my lips with his thumb and without warning put all four of his fingers in my mouth and stared violently fucking my mouth. He reached them far into my mouth and essentially tried grabbing the back of my tongue. Much to my surprise, I didn't gag or anything. Jimmy noticed this as well and I could feel his cock stiffen.
Using the hand in my mouth, he forced me down onto my knees. With one swift motion, he took his hand out of my mouth, grabbed the back of my head and pushed his throbbing cock all the way into my mouth. I should be ashamed to admit this, but when my nose touched his abdomen, I shot the biggest load of my life into my boxers. It was a massive wad of thick, urgent cum. As he fucked my throat, I could feel my brain chemistry change. I no longer felt ashamed; instead, I felt aroused and like I was doing what I was meant to do; like I had found my purpose. Jimmy was no longer the only one doing all of the work; I started moving my head back and forth with increasing vigor and need. I needed to feel Jimmy cum. I needed to feel the throbbing pulsations of his ejaculation. I needed to feel the warm, alkaline cum explode in my mouth. I needed to feel the fulfillment as I swallowed his cum. I had gone to an a****listic place and while there, I found myself and I was a fucking sissy faggot.
"Wow. You fucking like this, don't you, faggot? You've done this before, haven't you? I bet you're dying to eat my cum." I enthusiastically nodded up and down as I took his length in and out of my mouth. "Look at you. Jesus, you're fucking gay." I didn't realize it, but I had reached down and pulled my cock out of my boxers and I was jerking my cock with a rapidity that I didn't even realize was possible. Without any warning, he thrusted deeply and held me there as he came. I rubbed my tongue up and down his shaft as he filled me with what I wanted. He pulled his cock out of my mouth and backed up to look at me. Me crouching there on my knees, with saliva running all over my chin and my cock in my hand jerking vigorously. In that instant, I felt as if I was missing something and before I could really think, I lunged at him to try to get his cock back in my mouth. I needed it. "Back off, faggot. I ain't like you. I just came in here to humiliate you and it turns out that I didn't need to do anything. You humiliated yourself." What he said sank in and it was true. That realization made me cum for the second time that evening and this time it was truly a flood. It was almost as if I was ejaculating all of my pent up feelings and longings. I thought it would never end. I moaned and writhed and whimpered like a sissy as I shot a giant mess all over the hardwood flooring in my dorm room. When the last bit was drained from me and I slid down onto my ass, Jimmy said, "Lick it up." There was no hesitation; I got down and licked and slurped up ALL of my sissy cum. As I was licking up the last of it, I heard my door open and looked up in time to see Jimmy walk out of the door, with a final, "See you around, pussy."
He did see me around. He saw me waiting for him outside of his classes most days. Some days, if he was feeling generous, he would take me into a nearby bathroom and let me suck his cock in the stall. Other days, he would tell me to fuck off and slap me across the head. I don't know if he did it on purpose or not, but every time he slapped me, the longing to suck his cock would intensify and I would have to go find a place to jerk off and eat my own cum. One day, as he was coming out of his class, he was talking to another guy. I walked up and said, "Can I talk to you for a minute, Jimmy?" He said, "Whatever you're going to say, I want you to say it in front of Matt here." I begged, "Can we go find a bathroom so I can suck your cock?" Matt stared in astonishment and said, "You weren't k**ding. You really do have this pussy trained, huh?" Jimmy looked like he was going to say no, so I hastily threw in, "I'll suck Matt's cock too." Matt and Jimmy looked at one another and then walked off and beckoned me to follow. We went into the woods behind the economics building and Jimmy told me to get naked. I did so and they could see how hard my cock was at the thought of getting to suck them both off. Jimmy then said, "You're not going to suck my cock. You're just going to get to suck Matt's." I thought that if I did a good enough job, that Jimmy would change his mind, so I started to get down on my knees when Jimmy told me that I should bend over at the waist to suck Matt's cock. I bent over at the waist and found myself face to face with Matt's giant cock. I must have reacted because Jimmy laughed and said, "That's Matt Dresch. Mr. Dresch's son." My mouth watered and my cock started leaking copious amounts of pre-cum. I was going to get to suck Mr. Dresch's son's cock, which was just as big as Mr. Dresch's. As I was thinking that, Matt pressed the head of his cock against my lips and forced his way in. I tried my best to take it all, but at some point, my throat became narrower than Matt's cock and it would go no further. When I backed off of his cock, I could see that I had taken about 3/4ths of his dick into my mouth. Matt was fucking impressed. "Holy shit. Nobody has ever gotten that far before. And he didn't' choke or gag or anything. This is a really talented sissy you have here." Surprisingly, over the sounds my my slurping and gagging, I could hear Jimmy say, "I know" from behind me. A moment later, I felt something cold and moist press up against my asshole. Jimmy was going to fuck my ass! After much pushing and commands to bend down further or shift my ass, I could feel his cock slide into me. "I was wrong. You don't have a loose ass. You have a tight little ass." Jimmy pulled back on my hips and then pushed me forward and I knew what he wanted me to do. For a little while, they stood still while I moved back and forth on their cocks. As I shifted forward, I took Matt further into my mouth as I slid off of Jimmy's cock. As I shifted backward, I could feel Jimmy go more deeply into my asshole as the thick shaft of Matt's dick glided out over my tongue. Eventually, they took control and laid into me like I never thought possible. Matt tried, unsuccessfully, to make me gag and I thought that Jimmy was going to bruise his nuts from fucking my ass so hard. After about 5 minutes of using me like I wanted to be used, they both came at the same time, and as they filled me, I came as well. Matt's load was so large that much of it came out of my mouth and was wasted on the ground. Jimmy and Matt zipped up their pants and walked to their next class. I got dressed and as I walked back to my dorm room, I could feel Jimmy's cum leaking out of my now sore asshole.
After that first time getting spit-roasted, I spent so much time following Jimmy and Matt around that I stopped going to my classes. I eventually failed out of school, but was able to get a job in the campus cafeteria so I could always be available for Matt and Jimmy. Sometimes one or the other or both of them would come see me in the cafeteria and give me what I so desperately needed. I remember the first time Matt fucked me in the ass with his massive cock. We were in one of the bathrooms in the kitchen and I was shaking with nervous anticipation. I wasn't sure what was going to happen. When he finally penetrated my anus, my knees almost immediately buckled and it took all of my concentration not to cry out. He fucked my ass completely and fully and I couldn't make a single sound lest the other people working there find out I was a little sissy faggot. As Matt was nearing completion, he did something that Jimmy never did: he reached around and started jerking off my much inferior cock. When I felt his cock throb with the release of each jet of cum, I started to cum. Jimmy had trained me to catch my cum in my hand so that I could eat it for him and that's what I did then. When Matt left, I felt as though he had left a massive, eager hole in my backside. All of the cum that he had deposited pretty much came out of my gaping asshole all at once, though there was still a little left to leak out once I pulled my underwear back on and went back to work. I can't tell you how many meals I served with their cum leaking into my underwear.
When Jimmy graduated college, he got a job working for a bank on Wall Street. He didn't forget about me, though. With the money that he earned, he rented an apartment for me just down the road from his so that I would be available to fulfill his every need. But that's a story for another time.

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

3 years ago
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Sissy School Part 4

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

2 years ago
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My Daily Sissy Schedule Part 1

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

4 years ago
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Forever Her Sissy Chapter 5

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

2 years ago
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My Sissy Calling

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

1 year ago
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Sissy Farm Chapter Eleven

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

1 year ago
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Sissy Emma is turned

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

3 years ago
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My Sissy Schedule

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

1 year ago
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Forever Her Sissy Chapter 4 of 6

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

2 years ago
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The Sissy Contest

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

2 years ago
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Crowd Sourced Sissy 3

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

4 years ago
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Sissy Farm Chapter Eighteen

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

2 years ago
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Sissy Hypnosis Fun

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

2 years ago
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Sandys Sissy Maid

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

3 years ago
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Online Sissy Training

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

2 years ago
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A sissy called Jezebel

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

2 years ago
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Curiosity Spanked the Sissy Finale

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

2 years ago
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Sissy gets a black master

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

3 years ago
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I Now Own You Sissy

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

2 years ago
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My Sissy Secret

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

4 years ago
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Crowd Sourced Sissy 2

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

3 years ago
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Sissy Training at Last

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

3 years ago
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Sissy Farm 20

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

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