How I Became A Sissy 01 free porn video

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She slowly prepared me for step one

Well, it all started way back…I was 25 years of age…single by choice for about 4 years…and I was wild. I lived alone…went out 3-5 times a week and I changed girls at least once a week. I was young, carefree and I loved girls and women of all ages…I had young girls barely 16, I’ve had mature women around 40 to 50…and everything in between. Well, I enjoyed myself and I felt free like a bird. And that’s when I met Karmen. Well, actually I have seen her before. She was the girlfriend of one of the regulars at the bar where I sometimes sang and played the guitar. But that night I really noticed her for the first time. She was alone at the bar and she wore a long, floating, white summer dress. From the right angle and her standing in front of a light, the dress was just a little bit see through, so I was able to catch some split second glimpses of her slender body with that long legs, sexy hips and firm tits. With her long, blonde hair, she looked like a very sexy angel. I couldn’t take my eyes off her and of course she noticed it. Now as a rule I never went fishing at local waters, if you know what I mean, and especially I kept my fingers from already taken girls there. I just didn’t like the drama. It was much easier to go to a bar at another town, get a girl there and then go to a different town the next week. But I had no rule against looking and a little flirting. So I kept on enjoying her sexy appearance and we even smiled at each other across the room from time to time. Then I went to get another drink and suddenly she just stood next to me. „Do you like what you see?“ She asked. But the music was pretty loud so I turned to her and asked back: „Pardon!?“ She leaned nearer to my ear and said: „You can’t stop staring at me. So, do you like what you see?“ I answered: „I really like your dress!“ She started laughing. „Oh well, I think you are way more interested in what is underneath that dress!“ I looked at her and said: „Ya well, if you wear a dress like that, you should get used to guys staring and wondering what is underneath.“ With a sexy smile she answered. „Oh, I am used to it. In fact, I quite enjoy it. That’s the whole point in wearing that dress in this lighting.“ I laughed. „I like your attitude. You’re quite bold for a girl your age.“ I told her and she answered with that sexy smile again: „Well, I’m old enough to know what I want!“ I didn’t know exactly then, but she was just 19 at the time. „ So it seems!“ I said. She looked at me and said: “In fact, I am meeting a girlfriend tonight. We are going to a club. And I want you to join us!“ I hesitated a little bit, because it was against my own rules to mingle with someone from my home town. But I figured it’s not like a date, there’s gonna be her girlfriend, so it’s more like just going out as a group. And there was something in the way she said it, so confident, not as a question, almost as an order. I just couldn’t resist.

So I agreed, and half an hour later I sat next to her in her car. „You already had some drinks, so I am driving!“ she just stated and I really had no chance to disagree. We went to pick up her girlfriend and when we parked in front of the house she said: „Get out, she’s not ready yet. So, we’ll have a drink at her place until she gets dressed.“ So, we went upstairs to her girlfriend’s apartment. When the door opened I was a bit surprised. Her girlfriend was about 30-35 years old. Very attractive, with short black hair, beautiful, big, dark eyes and a heart melting smile. She was gorgeous, just not what I expected. She was not a girl…she was a woman! „Hey, come in you two.“ She said and Karmen introduced us when we sat down in the living room. „Listen, you two.“ Diana said. „I already had a little bit of champagne and I’m really not in the mood for a club tonight. What if we just stay here, have some drinks. I’ll put on some music and we have our own little party?” Again I was surprised by the turn of events, but again I had no saying in the matter because Karmen stood up, went over to Diana hugged her and said: „Great idea! I love our little parties!“ And then the two girlfriends kissed. And I mean they really kissed, long, deep and passionate. And while they were kissing, their hands explored each other’s bodies. I felt like I watched a really hot movie. Then Diana said: „Okay, if it’s a party, I’m gonna dress up appropriately of course. You two just get started. Karmen you know how to put on music, dim the lights, oh, and there’s champagne in the fridge.“ Then she disappeared, Karmen put on music, dimmed the lights and went to the kitchen. She came back with a bottle and three glasses and put it all on the table. I just sat there and couldn’t believe what happened. „Come here, I wanna dance.“ She said. Of course I stood up and went over to her. She was already moving her sexy body to the slow rhythm and I again couldn’t take my eyes off her. She stepped nearer and before I knew it, she pressed her body against mine, her hands caressing my back and we slow danced. Of course my own hands started to explore her slender body, too. She felt so good, so hot and my hands wandered up and down her back, then a little lower to her firm, juicy ass and I started to feel some movement in my cock. „Nothing!“ she suddenly said. And I asked „ What, nothing?“ She grabbed my face, put her lips close to my ear and whispered: „You are wondering, what I wear underneath that dress. It’s nothing…absolutely nothing!“ Now my cock was hard. And since she was rubbing her hot body against mine, she knew it…in fact, she felt it.“Oh, look at you two. Already in the mood!“ suddenly Diana said. We glanced at her and she looked breathtaking. She wore a really tight and short latex dress, long latex gloves and stood on extremely high heels, all in shiny black. Her dark hair was combed back with a lot of gel and with her really sexy make up and dark red lipstick, she looked like a model in a fetish magazine. „Oh, come on!“ Karmen said. „Now I will have to change, too. Or you are totally gonna out stage me here. Take over here, I’ll be back soon.“ Then she let go of me, left for the bedroom and before I knew it, Diana took her place, dancing with me. And she rubbed her body on mine just as tight and close as Karmen did seconds before. I felt like in heaven. Her body felt sensational in that smooth latex and I couldn’t help but caress and rub all over her back and ass. She did the same and my hard cock was rubbing against her thighs. I lost track of time, but suddenly Karmen re-entered the room in exactly the same outfit as Diana’s, only in red. She joined us and we danced in a little tight circle. I had one gorgeous, sexy latex goddess in each arm. Then Karmen and Diana started to kiss again…right in front of me. I watched their tongues explore each other’s lips and mouths. Suddenly they let go of each other and I felt Diana’s hot lips on mine…her tongue started a wild dance in my mouth. After a while it was Karmen’s hot and passionate kiss I felt. At some point we kinda kissed all three of us at once. „You should get rid of your clothes!“ Karmen suddenly said. „They don’t really fit in tonight’s ambient!“ Then the two latex goddesses started to undress me. And they didn’t stop until I was completely naked. Karmen then put her right latex hand between Diana’s legs and started to finger her pussy. Then she came to me and put her middle finger straight into my mouth. I smelled and tasted Diana’s pussy juice…it was heavenly. Then after fingering Karmen for a while, Diana did the same with her latex middle finger. The smell and taste of Karmen’s pussy was just as intoxicating and I fell in kind of a trance. Everything happened really fast, or maybe I just lost every sense of time and space. But suddenly I was lying on my back, Karmen sitting on my face and I was licking and sucking her juicy pussy. Diana meanwhile sat on my cock and started a wild ride. When I felt Karmen squirting all over my face in her first orgasm that night, I couldn’t hold back anymore and shot my sperm in Diana’s pussy. Diana then stood up, sat on the couch and spread her legs wide. Karmen crawled to her and started to eat out her pussy. She sucked all of my juice out of her and I watched fascinated, how Diana moaned and screamed in an everlasting orgasm. Then Karmen stood up and started to kiss Diana. And they started to swap the hot sperm, Karmen just sucked out of Diana’s pussy. Suddenly they stopped and both looked at me. „We share everything.“ Karmen said and I had a grin on my face. Then they stood up, came towards me and Karmen continued: „ Oh, I mean we all share everything.“ And then she gave me a long deep kiss, during which she let my sperm slowly pour into my mouth. That was the first time I tasted my own cum. And it wouldn’t be the last time. We fucked, sucked, licked, kissed all night long and in all combinations. And we shared all of our juices a few times more. At some point we just fell asleep. The next morning, after a good shower and a little breakfast, Karmen drove me back to my car. „You did well.“ She said. „I might consider letting you join us again!“ I was speechless and still tried to wrap my head around what happened the previous night. „Call me tonight at eight.“ She said. „I’ll decide until then! Now get out, I need to go home and get some more sleep!“ So I got out of her car. She drove away and I just stood there. I leaned against my own car and lit a cigarette. As I was standing there in kind of a dream state trying to get a clear head, I suddenly heard a voice: „She’s not for you, you know!“ I turned around and saw her boyfriend, or former boyfriend. Well, I actually wasn’t sure, if she is still with him or not. I said: „What? Who? What, did you say?“ He looked at me with kind of a desperate look. „You can have every girl you like. I’ve seen you, changing girls like underwear. She’s gonna break you. Better stay away from her!“ Then he turned around and disappeared. Well, that was weird. I finished my cigarette and drove home. I wasn’t sure what to do, I just tried to relax, watch some TV. Just having a lazy Sunday. But images from last night just kept popping in my head and I started to smile. „Wow, that really happened!“ I said to myself. I mean, I had some great nights with other girls, but that was a whole other level. And I had the chance to do it again. I had to call her. That was simply too good to miss out on it. But then I remembered the guy. „She’s gonna break you!“ he said. What the hell was that supposed to mean? I thought about it and figured he was just jealous. She left him, he didn’t take it well and now he’s trying to get her back, or something. Well, I even understood him. Who would wanna lose a girl like her? If he had, what I had last night on a regular basis, then he would be crazy to just let it go. Well, he tried, but he couldn’t scare me off. At eight that night I called her. But she didn’t answer the phone. I tried again a little later and then again, but she didn’t answer. I tried again the next day and the day after, but still no answer. So, I figured she moved on. It was a fun night, thank you, next! Hmm, it felt strange to be on the receiving end of such a treatment. I mean, I’ve done exactly the same like a million times. So, I said to myself: „Don’t be a pussy. She moved on, so you move on. Everything is cool.“ I decided to go out on Thursday. You know, new week, new girl. Back to business as usual. But somehow it didn’t work out as planned. I mean, I went out, I found a girl, she was sweet and sexy and really into me. But while I was talking to her at the bar, I couldn’t help but think about Karmen. I took the girl home and fucked her. „Hey, I wanna come in your mouth!“ I said while I was taking doggy style. „Ya, okay!“ she answered breathlessly. And then I said: „But don’t swallow it, keep it in your mouth. I wanna share the cum with you.“ She seemed to be confused: „What do you mean, share it with me?“ she asked and I said: „You know, kissing and swapping the cum from mouth to mouth.“ In a split second she stood up and looked at me in disgust: „What are you? A freak? …. Or are you gay? Why would you wanna get cum in your mouth?“ I laughed and said: „Well, why do you take cum in your mouth?“ She almost screamed :“ Ya, but I’m a girl! Are you a girl? Or are you gay? Only girls and gays do that. And freaks!“ Then she started to grab her clothes, put them on and stormed out of my apartment. I didn’t go out that weekend; I just wasn’t in the mood. Another week later on Saturday my phone rang. It was Karmen. I answered and just wanted to start asking her, why she didn’t answer my calls. But she just said: „ Be at the bar tonight! Or better, wait in front of the bar at 9 p.m.!“ Then she hung up. Of course I was waiting as ordered, she picked me up, we went to Diana’s place and had another great party. During the next two month we spent almost every night together. Some with Diana, some at clubs, where we met other girls and took them home, but most just the two of us alone at my place. At some point I realized, that she kind of lived with me. It was great. Without really talking about it, we were in a relationship. In a very open and hot one, but in a relationship.

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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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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...

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...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

4 years ago
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how i got my start as a sissy

. Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one...

4 years ago
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how i got my start as a sissy

.Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one...

2 years ago
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  • 38
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how i got my start as a sissy

Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one...

2 years ago
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  • 21
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Richard the Sissy

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...

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