The Sissy Exchange Program Ch. 03

Story Info
Vikki's first real cock.
10.6k words
4.81
26.9k
30

Part 3 of the 14 part series

Updated 06/12/2023
Created 06/07/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
wsxzaq110
wsxzaq110
226 Followers

After having cum twice, albeit with only one orgasm, Vikki was horny by the time she returned home and hoped Mistress Kristy sent him a 'My sissy Vikki...' email. Her world of sexual pleasure had been closed and narrow-minded but was now wide open with new ideas and possibilities. She was even still thinking of herself as sissy Vikki at that moment.

In her apartment, she checked her email, became excited that Mistress Kristy had sent one, and then stripped naked. Taking the buttplug out of the box, she sucked and spit on it and inserted it into her sissy pussy. It felt different from the vibrator and the dildo, but it pushed against her pleasure spot whenever her dick tensed, and she liked it.

Before watching the new videos (which were odd, because Mistress only ever sent her one at a time), she read the instructions about a series of stretching exercises for flexibility (one of the videos was a demonstration of the stretches) and a workout routine. She had never been interested in working out before, but she wanted to please her Mistress, so she looked up a nearby gym. She was relieved that the membership was only ten dollars a month, but disappointed that she would have to pay for the year up front. She could afford it, but just barely.

Mistress wanted her to become more flexible and work out, so she was going to become more flexible and work out.

The last set of instructions told her to start practicing a feminine voice and one of the videos attached to the email was a beginner instructional training video for male-to-female transsexuals to find their female voice. Vikki decided to watch it first and practice a little before getting to the porn to help further put her into her sissy mindset. Needless to say, her voice sounded fake, and she would need to practice as often as she could. The voice coach in the video even advised that she practiced by talking to herself and narrating what she was doing each day.

Putting the voice lessons aside, she got into a comfortable position and played the porn video. She was a little surprised that a regular guy was the one receiving Mistress Kristy's attention and not a sissy, but was even more surprised when a sissy helper appeared and was eventually ordered to suck on the man's cock. Her head bobbed back and forth for a minute and then she stopped long enough to take each of the man's balls into her mouth while his organ was resting across her face. Then she went back to his dick. When he came, Mistress Kristy stroked the guy and his cum spurted out onto the sissy's tongue. There was a close-up of the thick, white fluid in her mouth and then she swallowed.

Vikki nearly exploded right there.

She managed to hold off until she was in position. On her shoulders with her legs above her and her dick pointing right at her face. And her phone recording, of course. Not much came out, given that it was the third time she came, but she lapped up the two or three drops from her lips and sent the video to Mistress Kristy.

The next day, she played the video of the stretches. A feminine sissy appeared on the screen and described and performed each stretch. Vikki was amazed by how much she could arch her back while her ass was in the air and her face was down; not to mention how she could touch the back of her head with the bottom of each foot. Vikki clearly needed a lot of time and practice before she could get anywhere near that flexible, but she had to start somewhere.

Afterwards, she went to the nearest gym and signed up. She felt weird about recording herself working out but became less self-conscious when she saw other people doing it too. The first exercises were on the treadmill: a one-mile jog at a brisk speed and then a one-mile walk at a fast pace. After that was something called the deadlift. Vikki looked it up on youtube and did what the online coach did, albeit with a lighter weight. Mistress Kristy's workout instructions told her to always focus on her ass. As in, try to flex those muscles more then all others.

The other workouts included calf raises, squats, stair stepper, various abdominal exercises, and something called the 'glute-bridge'. That last one had her resting her upper back on a bench with a bar with weights resting on her hips. She would then thrust her hips up and then down as far as she could. Again, focusing on flexing her ass more than everything else. By the time she was done, she could barely walk. Half an hour after sending the video proof of her workout, Kristy texted her back.

Kristy: Very good job sissy Vikki

Kristy: Keep up the good work and I'll reward you with something very special Saturday

Kristy: 'three kiss emojis'

Vikki's heart fluttered.

And so did her dick, but she was too tired to move.

Kristy arrived home from work on Thursday and had three packages waiting on her doorstep. She gathered them and went inside. At her dining room table, she opened each package and took the wig downstairs and into the bedroom. She went into the closet, found the bald female mannequin head, and set it on the table with the vanity mirror. She then put the wig on top and played with the hair a little bit until the mannequin head looked good, thinking about how Vikki would look.

She smiled and went back upstairs, asking herself if she should give Vikki the makeup kit that night so she could begin practicing putting it on herself, or wait until the end of their session on Saturday. After a few minutes' deliberation with herself, she decided Vikki should begin learning to do things herself as soon as possible.

She texted her, asking what she was doing, and Vikki replied that she just got to the gym. Kristy then told her to finish her workout, send the video proof, and come over after her shower. Vikki replied with a 'Yes, Mistress' and just under two hours later, she knocked on Kristy's door.

Vikki was invited in, and she immediately stripped off her clothes because sissies never wear male clothing in her house. Vikki was complimented on her feminine voice but was told she needed much practice before it was passible. She agreed as she undressed. Naked, Vikki's body wasn't smooth, since she hasn't shaved in in five days, but for what Kristy had in mind, that was alright. The sissy's face was smooth and that's what really mattered. Plus, their session that day was impromptu and would be short. Kristy put Vikki's collar on her neck and walked her to the basement bedroom by her leash where Vikki laid on her back on the bed and was restrained as usual. It had been slow going because Vikki was still recovering from her first workout, not to mention the one she had just finished that day.

She was clearly excited to be there, given her almost solid erection, but was thrown a little by Mistress Kristy's outfit choice. She was simply wearing a pair of grey sweatpants and a baggy t-shirt. Nothing overtly sexy, but then again, Kristy could make any outfit look sexy.

"I know you're horny, sissy Vikki, but need you to focus. I need your penis to be soft and flaccid. Can you make that happen for me, sweetie?" Kristy asked.

"Yes, Mistress." Vikki replied.

"Good, gurl. I'll be back in about ten minutes."

Kristy left the bedroom and went back upstairs. At the dining room table, she opened her laptop and logged into her work website where she could review her upcoming sessions. On Monday, she had a regular client named Amanda, who was a laser hair removal technician and had her own clinic in the city. She was one of the few female clients The Matriarchy had, at least in Kristy's chapter. She was cute in a girl-next-door kind of way and part of her deal to pay for her sessions with The Matriarchy was that she had to provide her services whenever they asked.

She made a note to schedule Vikki a series of appointments for as soon as possible so she wouldn't have to shave or have stubble anymore. With the exception of peach fuzz. Electrolysis was able to remove that, but not laser hair removal. Which was fine because the peach fuzz allowed sissies to be more sensitive to the touch than completely smooth skin would allow.

She then looked over the rest of her schedule, seeing mostly regular clients and two newbies. Each client, regular or new, had to have their pictures taken, both close-ups of the face and full body, for their profiles. Plus copies of their driver's licenses to prove they were of legal age. They were all asked about their professions with the explanation that, if The Matriarchy could use their assistance with anything at any time, they would be provided with a twenty-five percent discount for all Matriarchy services. And they would only have to help on the occasional request, not all the time.

Many clients had jobs that The Matriarchy could use, like the wood-working guys who had made custom bondage furniture for Matriarchy Mistresses' private homes, for example. The result was that any Mistress could go into the basement of any other Mistress and feel right at home. Then there were welders and metal workers who made small, portable metal stockades that secured subs on all fours, including a post to secure the neck in place and another behind and between the legs for a dildo attachment.

Two other Matriarchy chapters each had a client who was highly skilled with computers and they both helped install and distribute VPNs for every chapter in the world as well as a special encrypted communication network. Among other things.

Kristy searched specifically for local clients who were metal workers, found one that was a regular of Mistress Vera, and made another note to have one of those portable metal stockades made for her. She had wanted one for a while, but hadn't seen the need to get it. The decision was just a spur of the moment thing while she waited.

She then closed her laptop and returned to the basement bedroom, pleased that Vikki's penis was completely soft. While waiting for Vikki to arrive at her home, Kristy had opened the box containing 'The Vice' from Locked in Lust and searched through the ring and anti-pull-out sizes that would best fit Vikki's little penis and had set everything on the dresser under the TV.

She first put the hinged ring around her scrotum and penis, then put the locking pin through the hole where the ends of the ring met. Then she put the cage over the penis with the hole on the tab above the cage going over the locking pin. The last part of the cage was what made 'The Vice' different from all other cages: the anti-pull-out. Like the ring, it was hinged, but unlike the ring, it was shaped like a rounded rectangle and had narrow tabs that comfortably pressed against the sides of the penis. After that was on, she put the locking pin cap in place and then put on the lock and closed it.

"There we go, sissy. Your penis is now under my control." Kristy said. "Just for the next few days. I want you to be very horny for our next real session." She leaned over and pressed her lips to the tip of the pink plastic cage.

Control the penis, control the male, she thought. The more she's denied orgasm, the more sexually aroused she'll be. The more sexually aroused she is, the more sexual experiences she could be convinced to participate in, with little-to-no hesitation. With little exception, it was the nature of the male libido. The behavior of males is almost always shaped by female influence, whether it's total compliance of beta males and sissies or the unintended creation of the MGTOW movement in resistance of that influence. It was all due to how females selected their sexual partners.

In Vikki's case, the trick was to find the balance between pushing her to be what Kristy wanted without going so far as to make her feel the desire to resist and reestablish her sense of masculinity.

The first step for that was to control her orgasms.

She then released Vikki's wrists and ankles and had her sit on the backless seat in front of the vanity mirror. The makeup kit was open and there were small brushes and tubes and a pallet of colored circles in a folding plastic book.

Vikki had no idea what she was doing.

Kristy opened up a sissy makeup tutorial on youtube and had Vikki watch it until her Mistress paused it. Then Vikki would put on her makeup just like the sissy youtuber did. She practiced a simple, sissy look five times over the next hour and a half and, after the last time, she looked pretty good and had finished pretty quickly. Before removing the makeup for the last time, Kristy had her put on her new wig and helped her position it just right.

Vikki was surprised how beautiful she looked.

A light layer of foundation, a hint of blush on the cheeks, pink eyeshadow with a thin black eyeliner, and mascara for lush eyelashes. And sissy pink lipstick and liner. Not completely passable, but quite pretty.

Kristy rested her chin on Vikki's shoulder and smiled. "I knew you'd make a sexy little sissy, Vikki." She held out her phone and took a picture of their reflections in the mirror. "I'll email you the link to the makeup tutorial and send the makeup and wipes home with you so you can practice again tomorrow."

"Will your sissy be putting on her makeup before she comes here?" Vikki asked, obviously hoping the answer would be 'no'.

"Of course not, my sissy pet. You'll bring the makeup with you when we meet again. Now wipe it off. I have another surprise for you for tonight."

"Yes, Mistress."

By the time she was done, it was almost seven and Kristy walked her upstairs where she got dressed. Kristy explained that they were going to go shopping.

"Don't worry, my pet. I know money is tight for you, so I'll pay. You'll just have to work off your debt by helping me at work a little more than I thought."

It was a lie, of course. She knew Vikki would have to help out with several sessions to pay for everything she needed to be a sissy. It was part of the plan. And those sessions would be part of the porn videos available on The Matriarchy's website and that's what was going to reimburse Kristy for the cost of making a new sissy.

That, and once Vikki has "graduated" the Sissy Exchange Program.

But that would be much later in the year.

With Vikki's makeup wiped off for the last time of the night, Kristy walked her to the bench where she opened a drawer and took out a roll of tailor's tape.

"Before you go, I want to take your measurements for a corset." she said.

"A corset, Mistress?" Vikki asked.

"I want to see you with a more feminine figure. Arms up."

"Yes, Mistress."

Kristy measured the circumference of her ribs under her chest, then her natural waist, then recorded them on her phone. The next two measurements were Vikki's hips at their widest point and the length from under the chest to the crease between her pelvis and thigh when her leg was bent. After typing those numbers into her phone, she walked Vikki upstairs where the sissy got dressed so they could go shopping.

Kristy had Vikki drive them into the city's shopping district and to Victoria's Secret. It was an expensive place, but only the best for sissy Vikki's porn debut. Inside, Kristy went through the drawers, talking about the best kinds of panties for sissies wearing chastity cages, and picking the ones with plenty of fabric at the front. They were mostly thongs, but some were cheeksters and others were boyshorts for her workouts. She had selected a lot of panties, but Victoria's Secret almost always had a '7 panties for $35' sale.

That didn't include the crotchless panties, but Vikki needed a pair of those regardless.

Next, Kristy chose a black lacy bralette, a pair of sheer thigh highs, a black lacy garter belt, and found a black mesh and lace garment that had the look of a teddy, but without covering the crotch, and had garter straps for the thigh highs. They went to the dressing room with the help of one of the cute salesgirls and Kristy had Vikki strip naked and try it on.

It was a size small, and it connected in the back like a bra. And it had about as much coverage there. The mesh over her chest wasn't as tight as it should've been, given that she had no breasts, but it fit her almost perfectly. Kristy hugged her from behind and grabbed a hold of her chaste genitals.

"I can't wait to see how sexy Vikki will look when we fully bring her out." she whispered into her ear.

"She can't wait either, Mistress." she whispered back.

"Good gurl."

Vikki removed the garment and dressed in back into her male clothes and Kristy paid for what they had. They then went to a large shoe store and searched for a sexy pair of heels for Vikki. Her size was nine and they found plenty of options, but Vikki was a little embarrassed about having to try them all right there in public.

"Relax, sissy." Kristy comforted. "It's near closing time and there aren't many customers right now. Besides, what are the odds someone you know will be here at the same time or the odds a stranger will recognize you later?"

Vikki agreed the odds were small, so she relaxed a bit and tried on six pairs before they both settled on a pair with a four-inch heel and an open-toe. Kristy then made a mental note about taking her to get a mani-pedi before their session on Saturday and paid for the heels.

Kristy was driven home, and she told Vikki to practice walking in her new heels and to wear only her new panties from now on. Even when working out. The whole evening had made Vikki excited, so she readily agreed. Kristy then kissed her good bye and exited the car.

Back in the basement bedroom, Kristy logged into a corset manufacturer's website ad a distributer and selected the same corset she'd chosen for her few previous Sissy Exchange subjects. It was called 'Satin Hourglass Curve Standard Underbust Corset with Hip Ties'. It had laces at each hip and along the back and four metal loops in the front that connect to four studs so it could be put it on and taken off like a button-up vest. Kristy chose the color black to match the sissy's lingerie and added it to her cart.

It was only another $120 dollars or so, but Vikki was going to make up for it in the short term and then be worth her weight in gold in the long term.

Saturday morning, Kristy texted her sissy pet to be at her house at eleven a.m., to be shaved smooth, clean inside and out, and to bring her makeup kit, outfit, and crotchless panties. After Vikki arrived, Kristy got in her car with a bag containing her own outfit, along with Vikki's wig, and had her drive to a nail salon for their mani-pedi's. Vikki was allowed a clear nail polish, rather than pink, because of her non-sissy life. When their nails were done, Kristy gave her directions to another place in the city.

It was a wide three-story building with its own underground parking lot. Kristy explained that that's where she worked and her and Vikki was going to help another Mistress with a client.

Vikki called yellow.

"It'll be ok, my pet. This place is all about discretion. Most, if not all, of our clients want everything to be discreet. They trust us and so should you." Kristy paused. "Besides, what are the odds someone you know will be here or that someone that you don't know will recognize you later? And even if they did, so what? They were in there for the same reasons as you, so they won't tell."

Vikki thought about it for a moment, then relaxed and got out of the car. Off in the distance, she saw a large trunk, about four feet long, three feet wide, and three feet deep, get loaded into a silver panel van equipped with a lift designed for wheelchairs. Kristy noticed her sissy had stopped to watch it.

"Coming, my sissy pet?" she asked.

"Yes, Mistress." Vikki said, turning to follow.

They walked across the parking lot to a set of automatic sliding glass doors and entered the elevator. Kristy selected the second floor. Once there, they walked through an eight-foot-wide hallway and when they passed one door, Vikki heard a muffled yell, like someone just got hurt.

wsxzaq110
wsxzaq110
226 Followers