Richard The Sissy free porn video

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Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a key, just in case I was at work when she found inspiration. I didn't think much of it. I only worked a few hours in the morning, cleaning up a local movie theater from the night before. The rest of the day, I had to myself. I tried to watch TV for a while, but quickly got bored. I tried to find some of the local boys, who liked to play football in my yard, but didn't like me. I was considered a wimp, especially since my sister was bigger than I was, even though she was two years younger. Mary was also a bully to everyone, including me. With no one to play with or no good TV shows to watch I went back into the house. For some reason I decided to explore my sister's room, so I went in to her room and start looking around. Her room was very frilly. She was also messy. Pants, skirts, panties, and her training bras were all over the place. I saw a pink, nylon, ruffled pair of her panties on the floor. I picked them up and examined them. They were very soft. I placed them up to my cheek to feel the smoothness of them. I wondered what they felt like on my cock, so I pulled down the front of my pants and underwear and rubbed them up against myself. I got an instant hard on. In fact, I had never been so stiff. I thought, I have all weekend; I wonder what it would be like to dress as a girl. I figured to get the full effect, I would have would have to shave what little hair I had on my body. I ran the bath water and put bath soap and baby oil in the water as I had seen my mom do on several occasions. I stripped naked and got in. I found my sisters shaver, lathered up my legs with soap, and started shaving my legs. I took my time, because I had heard my sister complain about nicking herself. When I finished my legs, I was amazed at how smooth they felt. I decided to trim my pubic area and shave under my arms as well. I had left a small patch of pubic hair around my still swollen cock. My underarm hair was gone with four quick wisp of the razor. The baby oil had made my skin very smooth. I just soaked for a while to feel the softness of my skin. I finally broke out of my fantasy and got out of the tub. I dried off and put my male clothes in the hamper, besides, no one was home and I could walk around naked, and no one would know. I decided I would stay in my sister's room for the weekend. I found the pink panties I had played with before. I pulled them up my legs. My cock became hard again as I adjusted them around my waist. I just stood there feeling my cock through the nylon material. I thought, "Stop, I have to put on a bra, and a?" I picked up one of her training bras. I put it over my shoulders and tried to snap it in place, but couldn't. I thought, "How does sis put this on?" I decided I could hook the bra and twist the bra around front, then pull up the shoulder straps. I tried it, and it worked. I decided I didn't want to dress all the way up, so I pulled out one of my sister's camisoles and put it on. I was really hard now. I closed her dresser drawers and walked out in to the living room. I twirled around feeling my body through the lingerie. All the sudden I heard a voice say, "What do we have here?" I froze with fear. It was Gina and she walked in front of me with a smirk. "I see with have a girlie wannabe here." I tried to say something, but just started crying. "Now, now you little sissy, what am I going to do with you?" I just stood there. I had never been so embarrassed. I tried to leave, but Gina grabbed my arm, "Stand right there, you little sissy bitch, I tell you when and where you will be, or I'll tell your family how the son is a sissy and likes to wear his sister's panties." I just stood there and tried to stop crying. While I stood in the living room I, Gina picked up the phone to call some of her friends. "Yeah, come over, I have something for you to see." I started to cry, "No, don't let me be seen by anybody, I'll be good." Gina held my face and said, "Shut up you sissy, my friends and I will have fun with you, and you will do as we say, or else." "Got it, you baby? I just shook my head in acknowledgement. Soon, Gina friends showed up. There was Karen, Misty, and Carol. The surrounded me and laughed and pulled at the panties I was wearing. Carol said, "Look at the sissy, he likes wearing his sister's panties." Misty pulled my bra strap and said, "He wears his sister's bra too." Gina told them, "Have your way with this sissy, he needs to be taught how to obey and serve." Karen, who seemed shy at first, pointed her finger in my face and yelled, "Kneel you sissy slut," and pushed down on my shoulder. I kneeled in front of her. She slapped my face so hard that my cheeks became red. I started to cry again. Karen then unbuttoned her tight jeans and pulled down the back exposing her tight round ass. "Lick my crack you stupid bitch!" I stuck out my tongue and just laid it at the top of her crack. She bent over and pushed he ass into my face. "I said, lick it fucking sissy!" I started licking her crack. She moved up, so my tongue would move down her crack. Soon I was at her hole. "Lick my ass hole you cry baby slut!" I hesitated, so Misty slapped the back of my head and screamed, "She said lick her ass hole you fucking cunt." I stuck my tongue out farther and stuck it into her ass hole. Karen reached her hands behind and grabbed my head and held it in place as I licked harder and harder. Then she moved away and Carol pushed me to the floor. She had her school uniform skirt on. She pulled it up. She was a wearing thong pantie. She sat on my face front ways grinding her mound into my face. "Open your mouth!" I opened my mouth a little, but she yelled, "Open wider slut!" I open really wide and she forced her panty-covered pussy into my mouth. She began to rub back and forth. Moaning louder and louder. Then she pulled her panties to the side and spun around so her ass was in my mouth. "Eat my ass you puke!" I stuck my tongue out and rimmed her hole, because I feared what was coming next. Misty started rubbing my cock through my panties. I became hard instantly. I heard her say as I was licking Carol's ass say, "I see this sissy really likes his panties and what is happening to him." The she slapped my dick, hard. I yelped, but was muffled by Carol pressing her butt hole on my mouth. Carol suddenly got up and yelled, "Get up bitch!" I started to stand, but she pulled me up quickly. "Stand there like a good sissy bitch!" I stood there with Carol's juice glistening on my face. I heard the voices of boys coming in the front door. I froze in shock as I saw Drew and Harry standing there laughing at me. "What is he doing," he questioned Gina. Gina replied, "We have ourselves a little sissy here." Carol looked at Drew and said, "I need you to payback a favor." Drew said, "Yeah, anything for you Carol." Carol smiled and said, "Go to the sofa and take off all your clothes." "In fact, both you and Harry take off all your clothes." Drew and Harry looked at each other and said, "No way, I'm not taking all my clothes off unless I get to see some tits and ass with a lot of cunt thrown in." Carol looked at them with the look of the devil in her face, "You will or I tell everyone about your little secret!" Drew started to take off his clothes. Harry thought for a moment of what could have scared Drew so much that he would start taking off his clothes. Drew looked at him and said, "Just do it, I'll tell you later." Harry thought, "What the hell," and started taking off his clothes. Soon both off them were completely naked and sat on the couch. Gina said to them, "Just lean back boys and enjoy it." Thinking they were going to get pussy, they leaned back. Their dicks were getting hard with anticipation. The Gina looked at me and said, "Get to it bitch, suck them dry." Harry and Drew started to protest, but Carol quieted them with a look. Misty slapped my ass and said get to it bitch!" I walked over and knelt in front of Drew. I stuck out my hand and touched his cock. He leaned back to grant me better access. I started stroking his cock. I felt it get warmer and harder as I stroked it. Just then, Gina yelled, "Don't feel him up, suck his cock you fucking slut!" "Start with his balls, sissy!" I held his cock as I looked at his balls. I decided I'd better get started, so I lower my face and mouth down to his balls. I stuck my tongue out and gave them a small lick. The taste was not like I thought, so I started licking them more and more. I then took one of his balls all the way into my mouth. His started to moan. I felt his cock get hard in my hand. I left the one ball and went to the other. I was getting into it. I wanted to have the taste of his cock in my mouth. I stared at the head of his cock and licked it with anticipation. I licked all the way down to the base. Then I took his cock into my mouth. Working the head in, then sucking all the way down. I started sucking up and down in a bobbing rhythm. I reached over to Harry with my hand and started to stroke him off as I was sucking Drew. Drew was started to force his cock into my mouth at the same pace I was sucking him. I started to feel his balls. He grabbed my head to keep his cock in my mouth. I felt his dick swell in my mouth. Then he shot his load to the back of my throat. Since he was holding my head in place, I had to swallow his whole load. He let go and slumped back into the couch. Misty yelled, "Next!" I knew what that meant. I started the same routine. I started with Harry's balls. Licking and sucking them, as I did Drew's balls. I started stroking him at the same time. Karen pointed out, "Our little sissy is still a virgin and needs her little hole fucked." Gina pulled me up and said, "Sit on his hard pole and get fucked as a sissy should be!" Gina then pulled my panties down and off. I straddled Harry facing him. Carol held his cock as Gina pushed me down on top of his rock hard cock. I felt a little pressure at first, but soon his cock, which was lubricated with my saliva, slid into my virgin ass. Karen said, "Pump up and down on his got you sissy!" I did as she said, feeling everyone of his thrust into my sissy hole. I pumped and pumped as hard as I could. I liked they way it felt as his manhood pushed in and out of my ass. My cock was getting really hard as well. I didn't know who was going to explode first, Harry or me. I found out I couldn't hold my load and shot all over Harry's chest. He kept thrusting into my ass harder and harder. The her grabbed my waist really hard and thrust me down on his cock as he filled my ass with his hot cum. I pulled off and put my panties back on. Gina said, "Your not done sissy, you need to lick up you mess." "So get to licking, bitch!" I leaned over to Harry and started to lick cum off his chest. When I was finished, Harry surprised me by grabbing face and started kissing my cum soaked lips. Carol, said, "I guess you all figured out Drew and Harry's secret, they love fucking and sucking each other." "I guess they have a sissy slut to include in their gay games." Gina said, "Don't forget, we own the sissy, and his parents and sister won't be home for a few days." I was ordered to clean up and put on fresh lingerie. The girls made me sit in a straight chair in the middle of the room while the planned what to do with me for the rest of the weekend. Gina has ordered me to stop writing for now, but she told me I would have to tell of all my humiliation later on. (the end)

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Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

2 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

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