The Sissy Exchange Program Ch. 01

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Mistress Kristy finds her mark.
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Part 1 of the 14 part series

Updated 06/12/2023
Created 06/07/2022
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Note: While there's no crossdressing in chapter 1, there will be in later chapters.

Kristy worked for The Matriarchy. It sounded more official than it really was. Like it was a 'New World Order'. It was actually club run by women who specialize in certain services that men pay handsomely for. It could be called prostitution under certain definitions, but most services didn't involve any kind of intercourse. Not without a strapon, anyway. The truth was, The Matriarchy was larger than a club. It was an organization with chapters in twenty-eight states in the U.S. and twelve more spread across Europe.

So many men fantasize about a dominant woman taking control. Restraining them. Whipping them. Degrading them. Wanting the Mistress to focus much of their attention on what's hanging between their legs. Less the aching and neglected penis and more on the sensitive orbs beneath it. CBT: cock and ball torture.

Men can be such pain sluts.

Kristy understood how a little pain during sex can heighten the experience, but she wondered how and why men would enjoy CBT, given how even the lightest flick of the finger could elicit feelings of pain almost on par with period cramps.

Oh well. As a Matriarchy Mistress, Kristy would inflict as much pain as she was paid to do.

She had begun her training as a Mistress at her local Matriarchy at the tender age of just nineteen. She had always enjoyed dominating and controlling her male partners (though, half of them had been turned off by it) and had found her calling. Now she was twenty-six years old with plenty of experience in the subtle arts of domination, bondage, sadomasochism, and even psychological manipulation.

She was trained by an older Matriarchy Mistress named Kelly, who had been a fine teacher and mentor and a good friend. Her and her husband, sissy Tori. Kelly had taught her everything she knew. And that night, Kristy's skills in psychological manipulation were going to be put to the test once again. Not that it was difficult when one seeks out the right type of guy.

Young enough that most women would ignore him in favor of older, more experienced, and more successful men. Slender enough that most women would think him too effeminate to be strong and protecting. And short. The average man in the U.S. was 5'7", so that was the maximum height she would go for. Young, slender, and short. The top three things the average woman found unattractive in a man. Being a virgin would be a huge plus, but it wasn't required. The perfect combination for a man with low self-confidence. The perfect combination for a guy who was thirsty for female attention.

The perfect combination for Kristy.

The perfect combination for The Matriarchy's 'Sissy Exchange Program'.

Kristy stood at the bar of a nearby club called Ray's. It was just a regular dance club like any other except that its minimum age was eighteen. The only other club in the city Kristy knew of that allowed eighteen year olds was a place several blocks away called 'Snowbunny'. It was an exclusive club and she'd been there several times with her friend and fellow Matriarchy Mistress, Jayla, who was a member.

Good times.

Unlike Snowbunny, Ray's provided fluorescent-colored paper bands around the wrists of eighteen to twenty year olds to indicate to the bartender not to serve alcohol to them. And to show Kristy who was within the ideal age range she was searching for. All she had to do was find one who was short and slender.

Kristy took a drink from her strawberry daiquiri and set the frosty glass back on the bar top. She stood at 5'6" barefoot but was standing at 5'9" in her black, strappy heels. She went to the gym almost every day to maintain her athletic figure and give her nude (or in most cases, semi-nude) body the appearance of superiority for her role as a Mistress. It wasn't a requirement for working at The Matriarchy, but she enjoyed her workouts.

Her firm legs were only covered near the top by her denim skirt and her black t-shirt was skin-tight, showing off the results of her hard work from the gym. She had firm abs, but her feminine pooch, however small, stubbornly remained. Like most women, she simply didn't have the body type to completely get rid of it no matter how hard she tried. Her shirt's neckline swooped deeply downward, revealing ample cleavage from her natural c-cups, and would be the first thing a man noticed about her. And that was one of the few drawbacks from working out at the gym: those c-cups had once been nearly double-d's.

Her face was between lean and soft, her lips full, eyes blue, and hair a natural blonde. Cut long enough to naturally hang down to the middle of her back, but that night it was tied in a braided ponytail. Her fellow Mistresses jokingly called the style 'the Mistress braid' because it was a sexy look that kept their hair out of the way while being their femdom selves.

Her makeup was light, as it usually was, but she applied a dark eyeshadow to highlight her blue eyes and added a light spread of sparkling beige eyeshadow over her exposed cleavage to further help draw a young man's attention. And she had her usual mascara. Long eyelashes were always sexy, man or woman. She usually wore red lipstick for her job, but she opted for more of a girl-next-door shade of pink.

With her beauty and physique, finding and successfully approaching a man who was thirsty for female attention would be as easy as breathing, but the fending off of guys she wasn't looking for was a chore that was quickly becoming tedious. She always thanked them and then politely declined their offers to buy her a drink, saying that she was wasn't interested. Then she had to get more assertive for those who refused to take the hint, thinking that she was just playing hard-to-get. There was even one guy whom she may have been interested in any other night. Then he thought he could win her over by flexing his right bicep muscle for her, which only made her laugh at the jock douchebag, grab her drink, and walk away to a table.

Part of her wanted to pick up guys like that and subject him to The Matriarchy. Especially the 'Sissy Exchange Program'. But his body size and type were just too wrong. Too muscular and too masculine for the exchange program. She needed a young, slender, and short man. Effeminate.

The best body type for a sissy.

After another hour, one such young man walked through the front door.

He had a neon pink paper bracelet to tell the bartender he was too young to drink, and he was a few inches shorter than the guys around him. No more than the national average height. Probably less. It was partially dark in the club, apart from the randomly moving white spotlights roaming the crowd and running up the walls and back again, so she couldn't tell if he was slender or if he bulked-up at the gym to compensate for his shorter height.

He did have a smooth-shaven face and longer than average hair for a man. About three or four inches long. That much she could see. As she continued watching him, he walked through the section of tables, moving sideways between the backs of two or more chairs toward the bar. He was quite graceful in his movements, suggesting he was more slender than muscular.

A very good sign.

The jock douchebag caught her eye as he was talking to his friends, his hand raised above the table, leveled flat, and then lowered it a few inches, like he was saying, "It's this high compared to something else". He and his friends laughed and then looked at the short young man. He had probably said something more like, "I knew a girl this tall and that guy is only this tall". That young man had probably been made fun of his whole high school life. That kind of thing made short men sensitive and unpleasant to be around. Especially when trying to convince them to be a good little sissy.

A thought occurred to Kristy and she smiled.

Time to show the jock douchebag what he can't have.

She stood and carried her drink to the bar, standing next to the short young man. He looked over at her and his eyes first took in her breasts. Understandable, given the low-cut neckline and sparkling makeup down there. Then he looked down her slim abdomen to her shapely ass and firm legs. He had to look up to make eye contact with the stunning woman who stopped and stood next to him.

Definitely shorter than the national average.

She turned her gaze at him and looked him up and down.

Definitely slender.

She smiled. "Hi there, cutie."

He hesitated for a moment as if he wasn't sure she was talking to him.

Definitely inexperienced with women, and therefore thirsty for female attention.

"Hi there, beautiful." he finally replied, smiling and feeling lucky.

"I'm Kristy. What's you're name?"

"I'm Vic. Come here often?"

She smiled. Nice to meet you, Vikki, she thought. "Only sometimes. How about you? Do you come here often?"

Before he could answer, the jock douchebag walked up and slid an arm between them, facing Vic. "She's taken, short-stuff. Take a hike."

Leaning over the bar and looking into Vic's eyes, Kristy said, "She's not taken and she wants to grab a table with you." she looked up at the douchebag. "Why don't you take a hike? And don't hit your head on the light fixtures on your way out."

The bartender came back with Vic's non-alcoholic drink just as the douchebag turned around. "What could you possibly see in a wimp like that?"

"Go back to your idiot friends and leave us alone." Kristy said, loud enough for the bartender to hear.

"Do we have a problem?" the bartender asked, glaring at the douchebag first, and than giving a soft glance at the attractive young woman with the t-shirt with the low-cut neckline.

Kristy continued to glare at the douchebag until he finally said, "Bitch." And then he went back to his table.

Kristy muttered, "Steroid-using bro-dude..." and then she turned to the bartender and said, "Thank you." He nodded and she turned to Vic who was leaning on the bar top and looking down into his drink, deflated. "So...how about we get a table?"

He looked over and softly asked, "What do you see in a guy like me?"

She slid closer, bumped her shoulder to his, and smiled. "Not a jock-wearing douchebag, that's for sure."

He looked up into her eyes with a hurt and vulnerable expression. "I'm serious." he paused. "What would any girl find attractive about me?"

Kristy turned toward him. She rested her left arm on the bar top and put her hand over his. Her right hand was on her left upper forearm, causing her right forearm to lift up her breasts and squeeze them between her upper arms. It caught his attention.

"Sure you're not six feet tall...sure you're not big and muscular..." she leaned in closer, her breasts slightly pressed against his left upper arm, "but you'd be surprised how many people would be interested in you. You just have to keep an open mind."

His eyes glanced down at her sparkling cleavage for a moment, then he looked into her pretty blue eyes. A smile forced its way across his face and he said, "Ok. Where were you sitting earlier?"

She smiled. She had hooked him, and they walked toward the table she had been using. She raised her middle finger at the jock douchebag as they walked by his table and then paid him no more attention. She and Vic sat down at her table. Not on opposite sides, but side-by-side at an angle so they could look at each other. She then steered the conversation toward his social past and learned that he was indeed a virgin. He had a girlfriend once, but she didn't seem very interested in taking things fast and he didn't want to be pushy. And he later found out that she didn't want to take things fast with him. One of his school's football players invited her over to his house and she easily gave in to his sexual advances.

And the next day, she broke up with Vic.

Over text.

Kristy gave her sympathies and then he asked her about what she meant about keeping an open mind. She pretended to be shy and bashful, saying that there were some kinks and fetishes that a lot of men liked, but was only shared by some women. One of which was her. He shifted in his seat, probably because he was getting hard in his pants and then asked what kinks and fetishes. She asked if he ever heard of "femdom" and he said no.

One of the drawbacks of going after a guy too young to drink: not old enough to know about certain things. Though she had hoped the absence of female attention would've led him to online porn and all the varieties that were the spice of life, she gave him a basic explanation and ease him into it and hoped he would be intrigued.

And he was.

He finished his coke, she finished her daiquiri, and they went back to her house. It was a two-story affair away from the suburbs and surrounded by woods. The back yard was big and well-maintained and her nearest neighbor was at least half a mile away. Vic could tell it had at least three bedrooms and two baths. Probably even a finished basement, too.

Removing his shoes, he said, "This is a nice place. Do you own it?"

"Yes; it's all mine." Kristy smiled, undoing the straps to her heels.

"What do you do for a living? If you don't mind my asking."

She softly pressed her pink lips to his and then whispered, "You're about to find out..." � � � � � � � � � � � � �

She smiled and took him by the hand, leading him downstairs to her basement. Vic saw several pieces of furniture, the likes of which he'd never seen before, sitting on hardwood floors in front of several huge mirrors that spanned an entire wall. Each piece was made with wood, stained a dark brown, and then lacquered to a shiny finish. Another wall had a bench with a sink on one end and several drawers underneath the countertop. Above it was a pegboard with several implements hanging on it, including what looked to him like various kinds of whips and things. Behind and to his right, was a closed door to another basement room.

"So...this is femdom?" he asked, still taking everything in.

"No...these are just some of the tools of the trade." Kristy replied.

"So, are you like...a prostitute?"

She placed her arms around his neck and smiled into his eyes. "I provide a service, if that's what you mean." she paused. "But if you're asking if I get paid to have sex, then the answer depends on how you define sex."

"Well...I don't think I want to pay for..."

She gave him another soft kiss. "You're not a client, Vic. You're someone I met at the club and brought home."

"Ok." he paused and then looked around. "I'm not sure if I want to do this whole "femdom" thing..."

"It looks kind of overwhelming, I know, but you don't have to do anything you don't want to. Aren't you curious to try though? To see why girls like me like shorter guys like you? Don't you want your first time to be spectacular?" She slid her left leg between his and felt his erection on her thigh.

"Well..." he began with shaky breath, "there's a first time for everything..."

Kristy's smile widened and she gave him a quick, soft kiss again. Much shorter than he would've liked, but he was with a gorgeous woman who was actually interested in having sex with him, so he had no complaints.

"First, we both need to look the part." she said. "I'm going upstairs to change into something a little sexier and when I come down, I want you naked and kneeling on the floor." She padded barefoot to the bench with drawers that sat under the pegboard with the various whips and knelt down to retrieve a soft mat from under the bottom drawer. She placed it in a certain spot near the stairs with the mat's long sides facing both them and the mirror. Before she left to go upstairs, she added, "Make sure you face the mirror and rest your hands on your knees. And don't turn around went I return. No matter how much you want to see more than just my reflection. Or you'll be punished." she smiled and winked and then left the basement.

Her room was the master bedroom on the second floor, where she slid out of her denim skirt and pulled off her slim t-shirt. Stepping out of her cheeksters and removing her bra, she was completely naked minus her jeweled naval piercing. On her left side was a tattoo of several bright red roses connected by a thorny, bright green vine that swirled around. The tattoo reached from just above her hip to just above mid-thigh. It curved forward and up toward her groin without reaching it and it also curved backward, covering more than half of her left cheek.

She walked into her large closet and scanned through her various "Mistress" outfits. Some were leather, some were latex, and two were rubber. In the end, she decided on the wet look of shiny latex. She chose a black, one-piece suit that had a halter top with minimal cleavage and a mid-thigh length ruffled skirt. Next, she chose her four-inch heeled latex knee-high boots. After lacing them up tight, she used a makeup wipe to remove her pink lipstick and then applied bright red.

It was a simple setup; one in which she could flash him the feminine folds between her legs if he was good. And because this was the most female attention he has ever received, he would definitely be a good boy. At least until she turned him into a gurl.

By design, the stairs to the basement were also made of hardwood instead of carpet. She wanted her submissive to hear the clacks of her heels at all times, starting with the top stair.

Clack. Clack. Clack.

Mistress is coming for you, sweetie.

She reached the bottom step and smiled that Vic had been naked and kneeling as he was told. With nothing between them and the mirror, he could see her reflection, but he fought the urge to turn around and see her for himself. And she could see that his body wasn't much in the way of masculine.

She stepped closer and stopped right behind him. Placing her hand on his head, she ran her fingers through his three-inch long hair and thought, Vikki would look good with long hair like mine. She leaned over to get a good look at what he had between his legs and loved that his penis was in the right proportions to his short and slender stature.

He was going to make a very sexy sissy.

"So far, you've been a good boy." Someday, you'll be a good gurl. "Good boys get rewarded and bad boys get punished. Are you going to keep being a good boy for me?"

"Yes, I will." he said.

She leaned over and whispered, "The proper response is, 'Yes, Mistress'. Nothing more, nothing less."

"Yes, Mistress. Sorry, Mistress."

He flinched at having added that, but Kristy simply smiled. "It's good to apologize when you've made a mistake or have been bad. And I know we haven't gone over much of anything yet and you're not a mind reader. Just try to learn what I expect from you as we go."

"Yes, Mistress."

"Good boy."

"Thank you, Mistress."

And I didn't even have to tell him to thank me, she thought. "Very good boy." She walked over to the bench to Vic's left and she caught him turning his head to look at her. "Eye's front." she lightly admonished.

"Yes, Mistress. Sorry, Mistress." he quickly replied.

Eager to please, she smiled to herself as she grabbed a leather flogger from the pegboard and an inch-wide leather collar and leash from the top left drawer. Turning back to him, she explained, "There are only two safewords and you don't have to say Mistress if you use them. The first is 'yellow' and it means you need us to stop and talk about what we're doing. The second is 'red' and is reserved only for emergencies. Make sure to use it if I go passed your pain limits and you need to take a break or even to stop altogether. This is about the pleasure of submitting to female authority. Understand?"

Keeping his eyes forward, he said, "Yes, Mistress."

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