The Sissy Exchange Program Ch. 03

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

"The rooms are insulated for sound, but not perfectly." Kristy explained, then added, "Some clients prefer...harsher treatment from their Mistresses. Don't worry, they're given the same safewords as you and can stop any time they want...they just don't want to. Because that's what they pay for."

Vikki nodded. "Your pet understands, Mistress."

Kristy smiled and continued until she reached the door she wanted, which was labeled, 'Dressing Room'. Inside, there was one woman who was dressed in a one-piece latex halter top and skirt and a pair of knee-high, high heel boots with her shiny brown hair tied in the same braid as Kristy when her and Vikki first met. Vikki then realized it was the same outfit Kristy wore during their first session. She was looking into the vanity mirror and applying red lipliner when they entered.

She looked over with blue eyes similar to Kristy's and said, "Hey, Kristy. Is this your new sissy?"

Kristy glanced over to Vikki and said, "That she is. Vikki, this is Mistress Vera. Vera, this is my sissy pet, Vikki."

Vera was still relatively new at The Matriarchy, having only worked there for a year or so. She had been trained as a Mistress by Kristy's mentor, Kelly, but on their personal time. Kelly had talked to Kristy about her from time to time when the two had first met, but it wasn't until Kelly had a gathering at her house when Kristy had actually met Vera. And her cuckold boyfriend. Vera's potential for becoming a Matriarchy Mistress was obvious to everyone there.

"Well, she's a cute one. Nice to meet you, Vikki." Vera said.

"Nice to meet you too, Mistress Vera." Vikki replied.

"I thought you didn't work weekends so you could have those special dates with your cuckold?"

Vera smiled. "I got a special request from a fan, so now our special date turned into a working date."

"Naughty little sex kitten, you..." Kristy smiled back, knowing that the special request probably involved the fan playing the part of the bull.

She gestured Vikki to place her stuff in front of one of the mirrors while she chose the one next to her. Her and Vera bantered while she and Vikki got out of their street clothes and began dressing in their sexy outfits. Eventually, Vera had to go and told Vikki to have fun and winked at her.

While Kristy began tying her hair into the same braid as Vera, Vikki asked, "Mistress, what's a cuckold?"

Kristy looked at Vikki's reflection and smiled. "A cuckold is a man who is the husband or boyfriend of a woman who has sex with other men." She paused to let the concept sink in. "Vera's boyfriend loves that she fucks other guys, especially in front of him, and half the time, he joins her in pleasuring her bulls. The other guys she fucks. It's like live porn for him, I guess."

Vikki nodded her understanding and opened up her makeup kit.

Within twenty minutes, Vikki was donning her wig and adjusting it so everything looked right. Kristy stood behind her, wearing a latex bodysuit with an open crotch, three-quarter sleeves, and a sweeping neckline showing off ample cleavage. Her knee high, high heeled latex boots forced her to bend over to see Vikki's reflection from where she was standing.

"It's good to finally meet you, sissy Vikki." she smiled into the mirror, wrapping a collar around Vikki's neck.

She smiled back, visibly excited at how sexy she actually looked. "It's good to finally bring her out, Mistress."

Kristy checked the time. "We have a little under an hour before we start, so let's see how well you can walk in your heels."

Just as Vikki started walked along the dressing room, the door opened and in came a tall, dark-skinned woman with the same braided ponytail as Kristy. "Am I late or are you early?" she playfully asked in a husky, yet feminine voice.

Kristy walked up to Jayla and hugged and kissed her. "We're early. I was just having Vikki practice walking in heels."

"I doubt she'll do much walking today." Jayla smiled.

"Probably true." Kristy turned to Vikki and introduced them to each other, explaining that they were going to help Jayla with a client and that Vikki was going to mostly play the same role as the sissy in the last video she emailed her.

Her pink cage twitched and Jayla notice. "Well, she seems excited about it. Are you excited, sissy Vikki?"

Vikki blushed. "Yes, Mistress Jayla."

"I'm glad to hear it, sweetie."

Jayla began undressing and Kristy had Vikki continue practicing her walk, giving her pointers and constructively critiquing her form. On one of the return walks, Vikki saw that the ebony Mistress had a real dick and she unknowingly stopped and stared.

"Vikki..." Kristy playfully started. "It's not polite to stare."

Jayla looked over and made eye contact with the sissy, who then blushed harder and looked away as she apologized. "She's adorable. Where did you find her?"

Kristy talked about how they met, and Vikki continued practicing her walk. Half an hour later, Jayla had finished dressing. She was wearing her leather underbust corset, a leather skirt with a thong underneath, and leather thigh high, high heel boots. As she stood, Vikki was caught staring again.

"May I?" Jayla asked Kristy, who then waved her hand toward Vikki and nodded. Jayla gracefully moved forward until she was a few inches from Vikki. "What are you thinking, Vikki? About this ebony goddess standing before you?"

Vikki was about five inches shorter and looking up. "This sissy is thinking how sexy you look, Mistress Jayla."

"And my girl cock?"

Vikki glanced down for a moment. "She's thinking...how sexy it is that you have one, Mistress Jayla."

Kristy smiled in amusement. Jayla had that kind of dominating effect on people. She was beautiful, well-endowed in the chest thanks to her transition and well-endowed between her legs thanks to genetics, but also had the air of dominance around her that others felt and unconsciously submitted to. Including domineering Mistresses like Kristy.

Jayla stared into Vikki's eyes for a moment longer and then smiled and gave her a light kiss on the lips. "You are so adorable, sissy!"

In another part of the building, clients get ready with BDSM outfits they had brought with them (or remain completely naked except for one of the public collars that everyone used) and used a bathroom where they cleaned themselves inside and out with their own enema kits. If they didn't bring it, then anal was off limits for the session. And all the clients were supervised during this to make sure they had cleaned themselves.

Jayla's client had just finished with the cleaning and was wearing a leather mask with holes for his eyes, nose, and mouth, and a leather body harness that included a built-in collar with a ring for attaching a leash. He then put on a white bathrobe and slippers so he could go from there to the assigned playroom without being indecent in front of other clients.

Mistresses and the sissies who worked for them didn't need to worry about such things, so Kristy walked Vikki to Jayla's playroom where Kristy sat on a stool and Vikki knelt at her feet while they waited for Jayla to go down to collect her client. It was decorated as though it was a dungeon, with the walls looking like the stones of a castle that fitted together so exactly that mortar wasn't necessary. There was a tall 'X' standing in one corner and a sawhorse stockade next to it that was identical to the one Kristy had in her basement.

On the wall opposite the sawhorse stockade, there was a bench with drawers that had a sink on one end and a pegboard above it with all the same implements hanging on it as in Kristy's basement. Off-center in the middle of the room, there was a cage that measured three feet by three feet by four feet and was topped with a leather pad that was four inches thick. On the same wall as the stool where Kristy was sitting, there was a table with a digital video camera and its charger on top. On the other side of the table, there was another stool where a young woman wearing yoga pants and a slim t-shirt was sitting.

Kristy introduced her as Samantha (Sam for short) who was one of their camera girls. She had gotten a degree in filmmaking but hadn't expected that kind of job. It didn't matter though, because she was making plenty of money to pay off her student loans and she kind of liked what she was filming. She admitted to having damp panties on multiple occasions after recording the session.

When Jayla arrived with the client, who then removed his robe and slippers, Sam said, "So, I'm thinking that Vikki could start in the cage with Kristy kind of laying on top while Jayla brings in her slave. Then everyone does what they do to keep it all moving organically."

Jayla agreed, so Kristy locked Vikki in the cage who then laid down in a comfortable position, looking bored, and Kristy sat on top and leaned back on her elbows, also looking comfortable and bored. Jayla and her male slave took their places near the entrance door and Sam began filming.

"Action!" she called.

Jayla walked her male sub into the middle of the room and asked Kristy, "Want to help me reward my slave?"

"I'm always up for rewarding good slaves." Kristy got up and looked inside the cage at Vikki. "And punishing the bad ones."

"Has sissy Vikki been a bad girl again?"

"Is it a day that ends in 'Y'?" Kristy unlocked the cage and Vikki submissively crawled out. "Do exactly as Mistress Jayla and I say, and I might reduce your punishment."

"Yes, Mistress."

Kristy turned to the ebony beauty. "So how may sissy Vikki and I help you?"

Jayla caressed her hand against her slave's bare chest and said, "He loves pain. Could you get my whip for me?"

"Of course." Kristy smiled.

While Kristy went to the pegboard for the forty-inch coil of whip, Jayla led her slave to the standing 'X' and bound his wrists to the top ends and his ankles to the bottom. Vikki knelt off to the side with her hands on her knees, wishing she had a mat under her, but she wouldn't complain. Not when she was in for more new sexual experiences.

Kristy handed Jayla the whip and the black Mistress struck a pose about six feet away from her slave. Her left was angled toward him, with her left foot pointing in his direction and the knee slightly bent. The whip was in her right hand and her arm was hanging loosely by her side. She stared at his exposed flesh. Studying it. A small smile formed at the corner of her mouth as she chose her first target. And she waited a few more moments to build the suspense. Her right hand went slightly behind her and then her wrist snapped forward.

Crack!

Her slave yelped the moment the whip made contact with his right shoulder blade; the exact spot Jayla had aimed for. He thanked her and she paused as she decided on the next location.

Crack!

Directly on his left cheek and another yelp and another 'thank you, Mistress'. She then struck the center of his lower back, then his right cheek, then his left shoulder blade; he thanked her each time and she paused for a few seconds each time. Then the backs of each thigh, the left cheek again, halfway up his back and to the left, halfway up his back and to the right, then the right cheek. Her male slave was sweating and breathing heavily. The whip had left welts that were growing redder by the minute at each spot it had made contact.

Jayla rolled up the whip and put it between Vikki's teeth and said to Kristy, "Would you mind getting my flogger, please?"

"Of course, Jayla." Kristy replied, taking the coil of whip from Vikki's mouth on her way to the bench.

Jayla stepped up behind her male slave and gently caressed his skin. "How do you feel, slave?" she asked in a low husky voice.

"Lucky to be yours, Mistress." he replied.

She smiled and pressed up against him, her breasts against two of his angry welts and her groin against his rear. She reached around his front and fondled his balls. "You are lucky to be mine, slave."

She squeezed down on his sensitive orbs and he groaned and pulled his hips back away from her hand, not that he could go anywhere. "Thank you, Mistress."

"You're very welcome, slave." she whispered, then released her grip on him. She turned to Kristy and accepted her flogger. "Thank you."

Jayla turned her attention back to her slave and spun the flogger around over her head once and struck across the man's ass. Before he could finish thanking her, she whipped her hand back in the opposite direction and struck his other cheek. She paused long enough for him to thank her without interruption and waited another few seconds. Then she focused her attention on his back.

Upper back, mid back, and lower back. The skin around his welts began turning a shade of pink. She moved lower, back to his ass, and then to the backs of his thighs. Once she was satisfied, she stepped up to him and put the cat-o-nine tails around his neck and pulled tight.

"Still feeling lucky that you're mine, slave?" Jayla whispered.

Sweat dripping down his face, he replied in a shaky voice. "Yes, Mistress. Very lucky."

She smiled. "That's my bitchboi..." she bit his earlobe and kissed the back of his neck before removing the flogger from his neck. She then handed it to Kristy, said, "Thank you." and then began releasing her slave's wrists and ankles.

She walked him over to the cage where she sat on it and had him kneel between her legs. Lifting her skirt up, she revealed her panties, which were covering a noticeable bulge. She then caressed his head and pulled him to her, so his face was immersed in her crotch.

"How does that smell, slave?" Jayla asked.

"Delicious, Mistress." he answered, his voice heavily muffled.

She pushed him back and pulled her panties to the left. At first, there seemed to be an average-sized penis folded and tucked under her, but pulled more and more out until a half-erect, seven-inch organ was out in the open for all to see. She gave it three strokes and it grew another two inches, mesmerizing her slave as well as Vikki from where she was watching.

"Stick out your tongue." Jayla said.

Her slave complied and she tapped the head of her dick against his taste buds several times, a string of her precum forming a connection between the two, almost regardless of the distance. Then, pressing it hard against his tongue, she squeezed out a large drop of precum and wiped it on the agile organ.

"Swallow." she ordered.

He closed his lips and swirled his tongue to savor her taste before actually swallowing. He then offered his tongue again and she put her member to it and pulled him toward her pelvis until she was as deep in his throat as she could be. She held him there until he gagged. Then she waited almost ten seconds before letting him recover.

"Mmm...such a good cock-sucking bitchboi..." she smiled down at him.

"Thank you, Mi..." he started before she grabbed his head and began using his mouth as a personal masturbator.

She put one foot behind his back, then the other, spreading her knees wide and using both hands to bob his head up and down. Her eyes closed and she tilted her head back, letting out a soft moan. Wet, sloshing noises were coming from his throat, leaving no doubt as to how deep she was going, but he gave her complete control and left his hands on top of his knees, despite gagging and coughing.

After another minute, she pressed his face hard into her pelvis for several moments and then let him go. "Very good, bitchboi..." she slapped his face, hard enough for him to really feel it through his leather mask. She stood up and walked to the narrow side of the cage. "Up and on your back."

"Yes, Mistress." he said, climbing onto the cage and lying on his back with his head hanging off the edge.

Jayla unzipped her skirt and let it fall to the floor and then looked into the kneeling sissy's eyes and said, "Vikki, remove my panties with your teeth."

"Yes, Mistress Jayla." she said.

She crawled to a spot behind Jayla and leaned forward, biting the waistband just above her plush, left cheek. She then lowered her head, pulling it downward until her face was nearly at the floor.

Jayla stepped out of her panties and said, "Good, gurl."

"Thank you, Mistress Jayla." Vikki replied, still kneeling behind her as she straightened up.

While Jayla caressed her slave's neck and chest, Kristy said to Vikki, "Make yourself useful, sissy. Start licking Mistress Jayla's asshole." Vikki hesitated, having never done that to anyone, and Kristy went to the pegboard and grabbed a cane. She struck Vikki's ass suddenly, causing the sissy to yelp and jump forward until her face was inches from Jayla's curvy rear. "When I tell you to do something, you do it, sissy." she canned Vikki's ass again.

"Yes, Mistress!" she said, reaching up and parting the firm cheeks of the ebony goddess in front of her.

"Thats better, sissy." Kristy said, striking another spot on her cheeks.

Her cock in her slave's throat and a sissy's tongue on her asshole, Jayla not-so-softly moaned and began humping the male sub's face. Vikki tried to move back and forth with her, but either her tongue kept losing contact or Jayla's ass hit her face. After another minute, Jayla rested her left knee on the cushioned top of the cage and Vikki managed to find a rhythm to maintain her oral duties.

Kristy continued caning her sissy pet, sometimes hard enough to make her stop licking and yelp and moan. Her pale skin was turning into a nice shade of sissy pink, like her chastity cage. Once satisfied, she returned the cane and went to Jayla's slave's left side.

Giving his six-inch erection a few quick strokes, she asked Jayla, "Do you think your slave deserves a tongue and pair of lips on his little cock?"

Jayla smiled. "He has been good..." she pretended to think about it and then pulled out of his throat. "What do you think, bitchboi? Does your cock deserve some attention?"

With a big black dick obscuring his vision, he said, "Only if you think so, Mistress."

"Good answer, slave." she nodded to Kristy and then slid her thick organ back into his mouth.

"Vikki." Kristy said, snapping her fingers and pointing to the floor on the other end of the cage. "Stand over here."

"Yes, Mistress." Vikki said, crawling to the spot and then standing.

Her heart raced. She had just been licking the asshole of a shemale goddess during what could be described as 'group sex' and was about to live a fantasy based on the last video her Mistress sent her. She was both excited and nervous.

She was going to suck another man's cock.

As a sissy though, she technically wasn't going to suck another man's cock. Just a man's cock.

The male slave's legs were bent at the knee, with the lower legs hanging off the edge. She leaned forward and braced her hands on either side of his hips.

"You're an eager slut, aren't you sissy?" Kristy said from the bench. "I didn't tell you to start sucking yet."

Startled, Vikki looked up and saw her Mistress smiling as she slid a strapon harness up her legs. "Your sissy pet is sorry, Mistress."

Sliding her favorite dildo through the ring, Kristy said, "I love your initiative and enthusiasm, sissy. Apology accepted." She tightened her harness and walked to a spot behind Vikki. With the sissy still bent over, she squirted some lube between her cheeks and toyed the head of the dildo against her hole. "I know you've been fantasizing about sucking cock, sissy Vikki, so go ahead and take him into your mouth."

In the fog of lust and orgasm denial, coupled with the images of the sissy in the video sucking a male slave and drinking his cum, Vikki lowered her face and wrapped her lips around the soft, warm head without thinking. Her first taste of a real dick. Just two weeks ago, she would've said that she was completely straight. And a man.