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THE COCKY SISSY By Rhayna Tera, copyright 2019 Warning: Humour. Author's Note: None. Disclaimer: This is a work of fiction. Names, characters, businesses, places, events, locales, and incidents are used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. RT THURSDAY AFTER SCHOOL Rick was fuming. "I'll show them! I'll really show them one day, those nasty meanies! One day. Maybe not tomorrow though..." The tiny, petite, scrawny, frail-looking, 15-year-old wimp stormed into his bedroom and threw his teddy-bear against the wall. He dropped his school bag (the Hello Kitty one) on the floor alongside his lily-coloured jean jacket. It had been another really tough, long, painful day of bullying at Capital City High School. Biff, Thor, Rex, and the usual others had pushed him into the girls' washroom. The day before it had been the girls' locker room. And the day before that the female staff washroom. And the day before the previous other day before that, they had held him and written "Sissy" on his forehead with the fuscia magic marker he always carried in his fanny pack. The girls at school were even worse. They were the girlfriends of the various Biffs, Thors, Rexs, etc. Madge and Mabel. Hazel and Mavis. Wanda and Janet. Kate and Cindy. Crystal and Candy. Betty and Brenda. These were the girls, the principal girls, of the high school. And Sara Collins too; she was profoundly stupid and immensely dumb. Anyway, there was the time the girls bleached his hair. The time they stole all his clothes from his locker during gym class and left a pink shift dress and flats in their place. And no one could forget when they had connived to have him present the human biology lecture on menstruation. As he took off his mauve blouse and matching denim jeans, he wondered why his classmates always picked on him for not being masculine enough. As he put on his floral-print, long sleeve t-shirt and black capris, he wondered why he was disrespected for his looks. As he sat at his vanity mirror with the glamour lighting strip and brushed his hair, he wondered whether he would ever be accepted by his classmates as the young man that he was. He tied his long hair into a low ponytail and went to make himself a tea. He thought better with tea. Chamomile tea. From France. He sat on the love chair and petted his mommy's cat, Ms. Pussykins, sipped his tea, and sucked his thumb. He'd get them back! He'd make them pay! They'd see! They never bother him ever again He became very excited. This is how real men plot revenge and other ne'er-do-well adventures. It was so exciting just thinking about revenge as a concept! He'd show them; he was so clever to have thought about revenge! After 45 minutes, he had no cunning ideas, and so he put on his fuchsia apron and readied to help his mummy prepare dinner. FRIDAY AT SCHOOL Rick was walking down the hallway toward his next class when he suddenly found himself surrounded by Biff and his cronies. Inwardly, he cringed in fear. But, outwardly, well, he cringed in fear there too; he was pathetic. "Rikki, would you like to be our friend?" Biff ingratiatingly asked. "Yes, please, Biff," Rick murmured. Behind Rick's back, Biff and his cronies smirked and sneered. "Okay then. Remember that everyone who has ever joined our esteemed circle of godliness has had to survive a couple of initiation rites. Rikki, you're no different. You have to undergo two initiation rituals. One is by us and the other is delivered by the girls, you know, Wanda and Janet, Betty and Brenda, and so on. Those are the girls, the principal girls, of our high school." Biff put his hand on Rikki's soft shoulder and steered him toward the boys locker-room. "You probably remember that every one of us here has, at least once, served lunch to the other members of our most distinguished collective in the school cafeteria." Rikki had no such memory but continued to be guided by Biff's hand. "Well, Rikki, you are going to keep that tradition alive for us today. You are going to serve us our lunches in the school cafeteria." Biff smiled at Rikki who replied that he had served Biff and his friends many times before, and so it would not be a problem now. "But," Biff interjected, "you're gonna be the first to do it in a French Maids uniform!" Biff opened Rikki's locker. The cronies had already gained entry to it. Hanging on the hook, next to his Little Pony jacket, was a French Maid costume in a Halloween package. Looped over the package was a pair of bright pink girls' running shoes. "Stop sniveling, Rikki. You have to prove your manliness to us. It takes a lot of guts to wear an outfit like that. Only the bravest of the brave. You know it takes a real man to wear a dress and a true hero to be a maid. Here's your chance to show us what you can be; are you just a man or can you be a hero? Show the school who you can be. Do it, buddy. Do it for your team; do it for us!" The falsity, treachery, diabolically evil duplicity of Biff's silver- tongued words would have been obvious to any other person in the world except Rikki. The lure of social acceptance blinded him. Plus, he was stupid. Rikki took the shoes and the costume and headed to a bathroom stall. Biff and his cronies stifled their laughs. Their snickering had to be suffocated when La Petite Rikki emerged. That fucking idiot, they thought: what a fucking loser. And thus lunch unfolded for Rikki. He stood in line for his new friends, got each of them a lunch tray, and waited until they were done eating before taking the trays back. He also wiped down the table before and after lunch. And he got some of them extra drinks, which he paid for himself. They easily confused his sissy brain, smiling at him or laughing with him as they continually eroded his wretched masculinity with damning faint praise. "You're doing great, dear." That sort of stuff. They complimented him relentlessly, making him associate compliments with his subservient behaviour. Because he was so stupid and so blindingly fixated, he failed to notice how everyone in the cafeteria was sneering or leering at him. They scoffed as he walked by or as he straightened out his pantyhose. The grade 7 boys pissed themselves laughing when his pink shoelace came undone and he gingerly kept his legs together as he bent to tie it. As Rikki had been serving lunch, Biff had a chance to talk to Wanda and Janet, two of the girls, the principal girls, of their high school. Wanda and Janet were neighbours. Both of their parents would be gone for the weekend. Only the girls' elder siblings who didn't care ("just don't do anything illegal") would be in charge of them. Party time. "Make sure he's at my house at 10 a.m.," Wanda said. "We can have a full day of fun turning him into a complete and irrepressible sissy." She and Janet immediately left and gathered the other mean, mean, mean girls to plot and plan. Goals were identified. A budget agreed upon. Orders were issued. Tasks were assigned. Operation Sissify Rikki took shape. SATURDAY AFTERNOON WITH THE GIRLS Biff and Thor escorted Rikki to Wanda's house. Rikki was dressed as instructed: a white t-shirt, an old pair of jeans, a pair of white cotton briefs, and an older pair of running shoes. "Rikki, the girls get into some outdoor adventure stuff. So, you're dressed and ready to rough-and- tumble with them." Frankly, the girls petrified Rikki; Biff's explanation mollified his fears --- a bit. Cindy and Candy greeted them at Wanda's front door. Biff joyously announced Rikki's arrival to the girls. Rex and Thor and the other cronies cheered Biff's speech and jeered Rikki onward into the house. The girls' little paws grabbed at Rikki and drew him in further. The baying of female wolves started growing louder the further he got inside. Unnoticed, Biff and the boys drew away and left the house. The front door closed behind them, and they walked the few blocks to Big Joe's house. They lounged around and waited for the college football pre-game shows to start. Friends started dropping by. Snacks and pop (for now) started to get consumed. The first e-message appeared. It was from Hazel: a picture of Rikki getting his hair washed. He was wearing a pink salon cape. The guys started chuckling. A second e-message appeared. This one was from Jackie-O. It was a picture of Rikki with a processing cap on, getting his hair coloured. The colour looked like ripe avocado. One could also see two of the girls working on Rikki's fingers. The guys were laughing. Later on, another e-message. Rikki was naked from the waist up. The girls had completed his facial makeup. Rikki looked rather pretty if one thinks that effeminate boys can look pretty. If one doesn't then, Rikki looked like a young sissy. Biff and gang roared. Another e-message showed the ear piercing. The first one. Another e- message showed the hoop earrings and studs. Then there was henna tattoo on his neck: two brightly coloured butterflies, one on each side of his Adam's apple. Then came a picture of a nipple piercing. Then another. The last picture before halftime of the 'game of the week' was of Rikki, poor, pathetic, pusillanimous Rikki, naked from the waist up, his hair permed and almost fluorescent green, his eyebrows high, arched, and thin, his eyes lined and tinted, his cheeks bright and pink, his lips fluffy and cherry red, his earrings sparkling in the daylight, his nipple and belly button piercings sparkling too. His white, pale skin reflected the lights. His face did not smile. In fact, he looked quite sad. What a riot! Biff and the gang rolled on the floor in tears. The first game ended. The second game began. Someone got out a beer. Then another beer appeared. The teenage boys got into the beer. Soon, there were chips on the floor. The telephone rang; more friends came over. Everyone wanted to know how the girls were doing with Rikki. When they saw the pictures, they laughed; what a fucking loser. SATURDAY NIGHT Biff got the first call. "Hi, sweetie. It's me, Crystal, one of the girls, the principal girls, of our high school. Look, I know we were talking about taking Rikki downtown and showing him off to everyone... Uh... Err... But there's just so much to do to him! So we're staying to... uh... finish our project. We can't just leave Rikki with Wanda; that would be so wasteful. So, I'm sleeping over here at Wanda's tonight with the girls and will catch a raincheck on our date. Love you, little boy." Biff thought he heard her chuckle. She hung up before Biff could say anything. Thor got a similar call from Hazel, Rex from Betty, and so on. And so it happened that the boys hung out together and watched the Saturday night college game. The Rikki jokes continued unabated. The guys joked about what the girls were up to. Surely they had shaved his legs by now. Was it possible they had already de-pubed him as well? They laughed and snickered and chuckled. But there were no more pictures or texts from the girls. Their evening wound down. In small groups, they headed home. Each lonely teenage boy eventually made his own lonely teenage boy way to his own lonely teenage boy bedroom wherein he performed a lonely teenage boy pleasure act before going to lonely teenage boy sleep. SUNDAY No one heard anything from the girls on Sunday. Nothing. Zero. But that was okay because Sunday was real football Sunday. Between the non-stop coverage on the football network and the more outlandish pre- game, mid-game, and post-game coverage on the other networks, there was much for the guys to watch and talk about. From a gender perspective, it was completely explicable that the guys did not call their girlfriends during football. Indeed, Biff et al would rather be watching football on Sunday than doing anything else. That included, arguably, hanging out with their girlfriends or, gasp, having sex with them (except during half-time for a quickie) Biff got ready for bed. It was late, but the Sunday night game had been worth watching in its entirety. Tom Brady, the miraculous 57-year old quarterback for the New England Patriots, executed another fourth quarter game winning drive. Another thrilling game from the ageless wonder. Even more thrilling, he devilishly thought to himself, would be tomorrow at school: seeing the super-sissy the girls would have turned Rikki into this weekend. Biff couldn't wait. MONDAY MORNING AT SCHOOL. Biff and his minions huddled around the school's main entrance, waiting for the girls to show up. "Here they come!" Thor cried. The jeering and cheering built up. "Let's see what the sissy looks like!" Rex shouted. The milling, topsy-turvy swarm of girls slowly approached. It was hard to distinguish who was who. There were so many ponytails. All of them had bright makeup on. The sun glistened off the earrings, all of their earrings. Dresses everywhere; no shorts, no pants, just dresses and shiny, smooth legs. Beautiful dresses flowing in the wind. Legs that men would start wars over. And shoes too. No running shoes here nor any casual boots. Just seductive, enticing strappy high-heeled shoes accentuating polished, perfect toenails. The boys were mesmerized by the collective beauty. "Where's our little sissy boy?" Biff giggled. Wanda and Crystal emerged from the swarm and approached Biff. They weren't giggling. They weren't laughing. They weren't even smiling. "That's not funny," Crystal said seriously. Biff jolted up. "Rikki is our dear, darling friend, and we will not let you mistreat him in any way at all anymore. Rikki, sweetie, please come forward," Crystal turned and beckoned a small figure who was in the middle of the swarm. The small figure approached. Biff could finally see it was Rikki. Green hair. Ridiculous curls. Overdone makeup. Grotesquely wrong earrings. Tattoos all over her or his neck and arms. A nose ring. CSL to dream of. A frilly satin pink blouse with a pastel blue skirt and white high heeled strappy shoes. Several bangle things that guys just don't understand on his or her wrists. Rings on each finger and most toes. A small tattoo of a unicorn was on Rikki's left ankle. "Rikki, baby," Biff taunted, "don't you look so manly." He laughed. Thor laughed. Rex laughed. All the other cronies laughed. "Go ahead and tell them, Rikki," Betty put her arm around his shoulder. Madge and Mavis walked up to stand next to him; they looked disappointedly at the boys. Biff was thrown off. He was not sure what was going on. "Thank you for the opportunity you gave me this past weekend," Rikki calmly stated to Biff and all his lackeys. "You tried to humiliate me in the cafeteria on Friday, Biff. You succeeded. You tried to humiliate me during the class trip to the petting zoo last month and you did; I'll never look at sheep the same way ever again. And you tried to humiliate me this weekend when you delivered me to Wanda." Rikki sniffled. Mavis stroked his arm soothingly. Betty petted his head. Madge nodded her head in encouragement. "Tell him, Rikki. Tell him like we told you to tell him." Rikki spoke. "You wanted me to get to know your girlfriends so much better. So I did. Biff, Thor, Rex, Byron, Launcelot, Matthew, Edgar, Herbert, Killin' Millen, Horace, and Steve, I deeply appreciate what you gave to me. I had never had sex before. Yet I've lost my virginity to the very best-looking girls, the very best-looking principal girls, in our high school. Your girlfriends. And I thank you for that," Rikki humbly mumbled and withdrew back into the swarm. And he disappeared into it. Thor laughed. "Did my Hazel do you with a strap-on?" The cronies pissed their pants laughing at Rikki and the image racing through their minds. Hazel had had enough of this. She knew a good thing when she felt one. "No, Thor, I did not do him with a strap-on. Honestly, I lay on my back, spread my legs wide, and begged him to fuck me hard, to fuck me like a real man would fuck me. And he did." Pause. "And it was so fucking good." Her voice carried conviction. Hazel slowly moved toward Thor. "That little sissy, as you have called him for years, has got a ten inch cock that is thick, juicy, and indefatigable." "What does that mean?" Thor asked with despair. "Indefatigable?" Hazel stared at him with scorn. "It means it doesn't fail on him, that he can keep it up longer that you can, that he can hit me in pleasure spots that I didn't even know I had. And these truths, these facts were gloriously demonstrated to me time after time this past weekend." She hissed at him: "I've never had so much cum in my life and I loved it! And he gave it to me, you didn't!" Madge seconded Hazel's opinion. Jackie-O agreed. Kate and Brenda each joined in: "Five times," per Brenda and "Seven," said Kate. "That's how it was," Judy said. "A broadening experience," Joan added. "You little boys are so dickless," said Zelda derisively. Lancelot started to cry. Matthew bent down to the ground and started to tie his shoelaces repeatedly. Herbert shoved his hands in his pocket and kicked the floor. "Babe?" Biff pleadingly asked Crystal. She didn't answer him. She stared at her toenails, all bright and colourful. She looked up at him, began to patiently explain a new life to Biff, and gazed languorously toward the sky. "Rikki is not to be touched. Ever. Our perfect little sissy will always dress up like a sissy, will always hang around us so we can remind him that he is a sissy, and will always do what we want him to do. He is harmless to you but gives me, us girls, so much pleasure. None of you need to know any more about our relations with Rikki." Her eyes had a distant look, as though she was remembering something joyous, rapture-filled, and incredibly wonderful. She shook her head out her daze and glared at Biff. "If you ever want to put your little spiffy-biffy in me again, then you will go along with this. We girls get Rikki. And all of you? You can ask us --- I mean 'beg us' --- for a good fuck. Or a BJ, Or a quick hand-job, assuming you haven't bored us. If we feel indulgent, then we might let you cum." She paused. "On our command." She sneered. "Like a good little sissy would." She looked at her boyfriend's crotch and snorted. "Little Biffy." END By Rhayna Tera, copyright 2019

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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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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...

1 year 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...

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...

1 year 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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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...

3 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...

3 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...

1 year 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,...

3 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,...

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...

3 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...

3 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...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

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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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
2 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....

1 year ago
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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...

2 years ago
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Theater sissy

This is a true story. No exaggeration, no BS. Hope you enjoy it.My ex girlfriend Tori and I had lived together for sometime. Our schedules were such that we had one day off together and one day off alone. I loved our together days but my alone days were porn days. And I LOOOVE porn.I would grab my case of beer, pack of smokes, a towel and head for the computer room. I would look up pics, vids, hop in and out of chat rooms. The whole nine. I was really getting into crossdresser vids at this...

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