The Sissy Exchange Program Ch. 08

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Vikki's night on the town.
8.1k words
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Part 8 of the 14 part series

Updated 06/12/2023
Created 06/07/2022
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It was Sunday evening, the day after Vikki had done a porn shoot on a hiking trail near a public park. She had been fully dressed up as a sissy, at a public place, in the afternoon. And not in a place where sissies and transwomen were common or expected. And by the time her sex partner, Steve, had dumped his load inside of her, her makeup was ruined in such a way as to leave no doubt as to what she had just done. And she still had to walk to her car along the trail.

What if someone had been walking that day? After she was well fucked in the face? And Steve had kept her panties, making her walk and drive with his cum leaking out of her sissy pussy without them! There were even a few drivers on the road that had seen her ruined makeup and did double-takes, coming to the only conclusion for why she looked like that: because she just had her throat fucked by a big dick!

And it all excited her.

And because she had broken rule number four at Alyssa's Secret that Wednesday, Kristy had sent her home after she cleaned up without her usual ruined orgasm. And once home, Vikki stripped naked and scooped what was left of Steve's load out of her sissy pussy and sucked her fingers clean. Then she checked her email to see if her Mistress sent her a new sissy hypno and, to her disappointment, she hadn't.

So, she watched one she already had.

It was the same hypno she'd first watched in Kristy's basement; the one where she was the star sissy in the video clips. The one titled, "To be a sissy: Vikki". With her laptop on her bed and holding the dildo Kristy had given her that was an exact replica of Jayla's, she pressed play and began sucking the phallus. The images of herself played with the captions about her first taste of cum and her first taste of cock and the loss of her sissy virginity.

She rolled over to her side while still watching, raised her leg, and penetrated herself with the black dildo. She sawed in and out slowly at first, but then removed it and took it deep down her throat to get it nice and wet so she could go faster. Angling it toward her pelvis from behind to stimulate her prostate, she moved it in and out as fast as she could, mesmerized by the video clips of her fully dressed up and sucking cock. The captions became variations of "Do you really know yourself?", "Is your DESTINY feminine?", and "Can you change it?"

Her arm tired, she adjusted her position so she was holding it under her while she rode it cowgirl style.

A video of Vikki walking down a hallway fully dressed and looking sexy played with the caption "Would you want to?"

A still image of Vikki lustfully looking at the camera with a hard cock in her hand and the tip resting on her extended tongue. "You're changing..."

A montage of men thrusting into Vikki's eager rear. "You're body...", "along with...", "your SEXUALITY."

Various video clips of Vikki sexily posing for the camera. "Mold yourself...", "into a GIRL."

Vikki's heart raced and she rocked her hips back and forth and up and down, horny beyond belief and desperate to cum. Her eyes were glued to the screen as she tried and failed to orgasm from her sissy pussy alone.

Video clips focused on the breasts of topless women. "Grow breasts"

Video closeups of Vikki's freshly made up face. "Wear makeup"

Video clips of Vikki posing for the camera. "You are not a man."

Various clips of Vikki having sex. "Your only sex organs...", "are your mouth and sissy pussy"

"Will this happen?"

"Is it FATE?"

"Your life will change"

"A sissy forever"

"Is this your future?"

"Is this your fate?"

"Are you really a gurl?"

The hypno faded to black silence and Vikki was left sexually frustrated and wondering the same thing. She dressed pretty, wore makeup, sucked cock, and men fucked her sissy pussy.

Am I really a gurl, she asked herself?

The next morning, Vikki, dressed in her male clothes, entered the restaurant where she worked and went in the back to clock in. One of her coworkers was already there, a twenty year old guy named Eric who was several inches taller (like almost every man on the street). He was average build for a guy whereas Vikki was average build for a girl, minus the bubble-butt and breasts, of course. She walked by him and entered her employee number into the computer.

"Hey, Vic." he said. "Still growing out your hair?"

"Yeah." Vikki said, feeling weird for having used her male voice.

"You know, we've all been talking ever since you changed the style a week or two ago..."

Turning to him, Vikki asked, "About what?"

"Your hair. And other things..."

"That it's long?"

"Don't take this the wrong way or get offended, ok? We're just curious because it's a feminine style and..."

"And?"

"And Alice noticed that your eyelashes were longer and darker, like you had been wearing mascara and didn't get it all off. She said that could be hard sometimes."

Vikki's heart raced. What was she going to say? They were mistaken? Her hair wasn't really styled femininely? By a man who had fucked her several times no less? That her eyelashes were just darker on somedays?

She swallowed and softly asked, "And if all that was true?"

Eric held up his hands. "It's ok by us...and we know it's none of our business, but we're just curious." He paused. "Are you gay? Or trans or whatever?"

Vikki hesitated for a few moments, which was as good as telling him that, yes, she does dress up in lingerie, wear makeup, and let men fuck her.

Then she shook her head. That's not what he asked, she reminded herself.

"Um...well...kind of...?"

"Ok." he simply said. "That's cool and all and it's what we were kind of thinking."

Alice, a twenty-two-year-old, pale-skinned woman with a slim body from a vegetarian diet and short blue hair suddenly walked into the break room from behind Vikki. "What's what we were thinking?" she asked, staring at Eric with eyes that told him to shut up.

"That he's..." he waved his hand toward Vikki and shrugged.

"I thought we agreed we wouldn't say anything unless he did first?" she admonished, then turned to Vikki. "It's really none of our business, but if you wanted to...dress and behave differently, more feminine...it would be ok with us."

Vikki blushed and looked down. "Was I really that obvious?"

"There's not much you can do about your hair," Alice began, "and sometimes you really have to scrub your eyelashes to get all the mascara out, so it's not like it's easy to hide it..."

"Well...I kinda do want to...be a little more feminine..."

Alice smiled and hugged her, saying, "Good for you, sweetie! And what about showing us your makeup skills?"

Vikki bashfully smiled and thought that her workday wasn't going to be so bad after all.

After work, she went home feeling the need to text Kristy and tell her that her sissy pet was willing to go out in public as the gurl she was. She didn't respond right away, so Vikki stripped naked and began her stretching routine before she went to the gym. Recording herself, she got on her knees and arched her back as she leaned forward until her upper body was flat on the floor while keeping her thighs perpendicular to it. Feeling the stretch throughout her lower back, she held the position for ten seconds and then relaxed. Playing the video, she saw that she could present herself to a man in quite a sexy pose. Much better than when she first started.

She still couldn't touch the back of her head with the bottom of her foot, but she was making progress overall.

She then laid on her back and put her palms on the floor with her fingertips just under her shoulders. Adjusting her feet flat on the floor right next to her rear, she pushed herself up and arched her belly toward the ceiling as far as she could while tilting her head back, so she was almost looking at the floor. She held that pose for four seconds, heard her phone go off, then finished counting to ten before checking it.

Kristy: I'm glad to hear it sissy 'heart emoji'

As Vikki started typing her response, Kristy sent another message: Let me check my schedule and we'll have a girls night on the town 'emoji of a smiling woman with her left palm up'

Vikki deleted her partially typed response and instead sent: Girls night!

Kristy: I'll let you know when I figure out the details 'kiss emoji'

Vikki: Your sissy looks forward to it Mistress!

Vikki smiled to herself, her heart fluttering slightly in anticipation. Putting her phone down, she got on her knees and leaned backwards, trying to get her back flat on the floor as she continued with her stretching routine.

In the dressing room at The Matriarchy, Kristy set her phone down and removed her corset. She had just finished whipping a client who loved to be told how small his penis was when her phone received Vikki's text. She smiled to herself at the thought of the sissy being ready to go out on the town, full makeup, fully dressed, and fully femme. Kristy had some ideas for when the time would come, so she texted Sharon because she was key. She was a sex counsellor, but she knew enough about gender dysphoria to fake being a gender counsellor and help Kristy plant the seeds for Vikki's full transition and feminization.

Kristy could do most of the work, but the credentials of a licensed counsellor made everything more convincing to the average person.

Kristy: Code pink

Sharon responded within ten minutes: Vikki? So soon?

Kristy: Yes

Kristy: I'm thinking Thursday like we did last time

Kristy: But keep your calendar open

Kristy: I'll ask Mia to join us and add her sparkling personality 'wink emoji'

Sharon: Sounds good. Let me know the time when everything's confirmed

Kristy: I will

Kristy then made a few calls to set the plan for Vikki's night out in motion, set her phone down, and finished removing her overbust corset. Vikki was going out in the general public and her Mistress was going to make sure her sissy enjoyed every minute of it so she would want to go out again and again.

So on Thursday, Vikki sat in front of the vanity mirror in Kristy's basement. She was dressed mostly in the same outfit she wore in the park: a black skirt, black long sleeve t-shirt with lace around the boatneck neckline, bralette, a thong instead of her cheeksters that were still in Steve's possession, and her open-toed heels instead of her grey shoes. That evening, though, she was also wearing her jeweled buttplug on her Mistress' order. She had just finished her makeup: light foundation, a hint of blush, silver eyeshadow, liquid eyeliner, mascara, and pink lipstick. Her hair was styled with some of her bangs covering her left eye, but otherwise it simply hung down to her jawline.

For a moment, she wondered what she would look like with a cute, braided ponytail.

Kristy stepped up behind her and said, "Don't you look cute this evening?" She then stretched something wide and lowered it around Vikki's head until it closed around her neck. "This is for you. It's an elastic choker and a perfect accessory for telling men that you're kinky and submissive." Kristy winked.

Vikki smirked. "Thanks, Mistress."

"Seriously, though. You look good. I'm proud of you for deciding you're ready for this."

"Thank you, Mistress." Vikki said, looking into the bright blue eyes of the woman behind her. "You found something inside your sissy that she didn't know she was missing."

"Only your inner sissy cock slut!" Kristy joked, then caressed the sissy's hair. "This is a big step. One that could lead you to more changes, like being feminine more often. Being Vikki more often."

"It probably would, Mistress."

Leaving the house, Kristy drove them into the city where they would meet Sharon and Jayla at the mall. If Vikki was going to be feminine in public more often, she would need more everyday clothes. Mia wasn't going to be joining them because she already had plans that day, but she promised to make it up to Vikki with the stripper lessons she offered. Maybe Friday or Saturday.

Kristy received a text from Sharon stating that she was parked next to the pole labeled 'J' and, after Kristy found it, she spotted Sharon's car and parked next to it. Jayla was with her, and they all exited their cars and gathered together.

"So, you're ready and willing to be out and about in public as your femme self?" Sharon asked Vikki.

"Yeah." Vikki nervously nodded. "Some of this sissy's coworkers asked her about her feminine hairstyle and mascara that she couldn't completely clean off and they were ok with it."

"That's good, sissy. Everyone should be who they are on the inside, right?"

"She thinks so."

"And this is who you are on the inside?" Sharon questioned. "Have you ever felt like you were a girl before?" Vikki thought for a moment and said that she'd never felt like being a girl before meeting her Mistress, but she feels it now. "Hmm...I wonder if you actually had these feelings before, but then blocked them out for some reason. From what Kristy told me, you took to your sissyhood pretty fast for a guy who never felt this way before."

Vikki nodded. "It does seem kinda fast, doesn't it?"

"And that's not a bad thing, but would you be interested in having a counselling session with me? I'm trained in recovering repressed memories and feelings and I'm curious to see if you have any related to your feminization."

"I think that would be a great idea." Kristy interjected. "And maybe you repressed your attraction to men too. How else could a straight guy become such a cock slut?"

"That would make sense." Sharon agreed. "Heterosexuals don't just suck cock because a woman tells them to."

All eyes on Vikki, she thought about what was said for a minute and then agreed to see if she really did repress her inner feminine self and any attraction she had to men.

"How would that happen?" she asked.

"Trauma is the most common cause, but you may have just forced yourself to adhere to societal expectations and buried the non-conforming part of yourself as a result. We'll see once I have you on my couch."

With that, Kristy changed the subject to the future additions of Vikki's wardrobe that awaited her inside the mall. Vikki continued to be nervous as they entered, imagining that everyone was staring at her, but the truth was, only a few people took notice and those that did simply saw a group of friends. Two beautiful women of average height, one beautiful woman of above average height, and one woman of average height who looked pretty, but on closer inspection was actually male. Probably one of those trans people that are always being talked about on social media and such. Not really a big deal.

As they browsed the women's section of the first store, an attractive twenty-something year old salesgirl asked if they needed any assistance and Kristy said that Vikki was looking to expand her feminine wardrobe. The girl recognized that she was male and simply asked what kinds of things she was looking for. Vikki hesitated for a moment before answering.

"Um, just normal clothes." she said in her well-practiced femme voice. "Skirts and shirts, mostly..."

The salesgirl, whose nametag said 'Tiffany', smiled. "Don't be nervous, sweetie. We get plenty of male customers shopping in the women's section for themselves, it's no big deal."

Vikki gave her an uncertain smile and said, "Thanks."

"So, skirts and shirts? Any leggings or dresses? We have those over there as well." Tiffany waved her hand over a rack of hanging tops and pointed to a shelf with leggings.

"It might be better for her to avoid anything that's form-fitting in the groin area." Kristy commented. "But she definitely could use a new dress!"

"Of course..." Tiffany said, realizing the reason would want to avoid tight-fitting clothes like leggings and walking over to the store's selection of sundresses. "We have plenty of cute little dresses, both plain colored and in flower print here, but this is about all we have as far as dresses go. Let me know if you need anything else." Tiffany gave Vikki a reassuring caress on her shoulder and then left to help out another customer.

"See how helpful and understanding she was, sissy?" Kristy asked. "You have nothing to be afraid of by being yourself in public."

Vikki smiled. "Yeah...your sissy guesses you're right."

"Her Mistress is always right." Kristy joked.

They looked through the various sundresses and decided on only one of them. It had a floral print full of daisies, spaghetti straps, and a conservative neckline. When Vikki stepped out of the fitting room, she looked cute with the dress hugging her waist and the flared hem ending just above mid-thigh. A pair of sandals, wide brim hat, and sunglasses, and she'd look like she was out for a day at the beach.

Though the sissy didn't have much money, Kristy had already told her that she would pay, but that would mean Vikki would have to star in more porn shoots. Vikki playfully whined as though she didn't want to, earning smirks from the others, and then they continued shopping.

An hour later, Vikki had several new skirts, tops, dresses, shoes, and with a visit to a place called Fredrick's of Hollywood, more lacy lingerie. After they went to a nail salon for their mani-pedi's, they stored the shopping bags in the trunk of Kristy's car and then continued their night by walking around downtown, just to get Vikki used to being out in public. They window-shopped here and there, going into some stores but not others. The sissy received stares from people; some curious, some uncertain, and a few others from men with a twinkle in their eye.

They had worked up an appetite and stopped in a sit-down restaurant and ordered drinks while they looked over the menu.

"You know, sissy," Kristy began, "You're exercising almost every day, but this might be a good time to talk about diet to help out your feminine curves."

Vikki looked down at her already slim waist. "Are you saying your sissy is fat?" she playfully asked.

"Of course not. I'm simply saying a good diet would help keep you slender and sexy like a sissy should be. Plus, avoiding certain foods can help make it easier to keep your sissy pussy nice and clean."

The middle-aged couple in the booth next to them glanced over and studied them, their eyes finding Vikki and stopping. Vikki felt their stares but couldn't bring herself to look in their direction.

"So what do you recommend?" she asked, stopping herself from addressing Kristy as 'Mistress'.

Kristy looked at the couple, who continued to stare, until they looked away and then said, "I've got a nutritionist that helps me with a meal plan. I'll schedule a visit for you, but until then, enjoy yourself."

"Thank you, Mi..." Vikki glanced over at the couple and lowered her voice. "Mistress."

Kristy nodded in understanding and whispered, "You can just call me Kristy while we're here, but don't forget rule four."

"Yes, Mi...Kristy..."

Kristy giggled and they turned their conversation to normal, everyday topics, which for a group of three Mistresses and a submissive sissy cock slut weren't so normal and everyday for most people. After having eaten, they paid and exited the restaurant and Kristy asked Vikki about how her feet were doing, considering how long she's been walking in heels that night and how long she's been walking in heels overall.

"They're getting a little sore, Mistress." she replied.

"Well, I know a massage place near here. How about we all end the evening with one?" Jayla asked.

"Sounds good to me. I'll just pimp my sissy out to pay for it!" Kristy joked.

They all laughed, but the reasons why were different. Vikki thought it was just a joke, but to the Mistresses, the real joke was that each time Kristy took money from the men for the sake of the porn video they were making, they were actually paying to fuck the sissy. The subs and slaves of The Matriarchy were given opportunities to pay extra for having sex in addition to the normal dominatrix services that were offered, especially the ones who paid for chastity play, but prostitution was a service that wasn't widely advertised for obvious reasons. Even if the 'prostitute' was usually another sub or slave paying to be fucked as part of their training.

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