The Sissy Exchange Program Ch. 06

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"Hands here," Kristy pointed, "and feet here." Once Vikki was in position on her hands and knees, Kristy then used small carabiners to connect her leather cuffs to the four ends of the base and then locked her neck in the stockade. "That's better. Comfy?"

"Yes, Mistress." Vikki replied.

Kristy retrieved a bottle of lube and a latex glove and knelt behind the sissy. "We've never used this before, but I think you'll enjoy yourself."

She put on her glove and applied several drops to her sissy pussy and the dildo. Stroking it until it was completely coated, she then aimed it to Vikki's little star and slowly slid it forward, spreading her open and penetrating her deeply. After locking it into place, Kristy removed her glove and turned on the TV. Vikki watched as she selected the videos folder and then the Sissy Exchange Program folder. After she clicked on a folder titled "Feminization and Sissification", she scrolled through a large selection of other folders, all titled with female names, and double-clicked on the folder labeled "Vikki - Illinois". There were two other Vikki's, one in California and another in France, but maybe she would ask about that later.

That folder contained four videos, the first of which was called "First Taste of Cock"; the second, "Gloryhole Slut"; and the third, "First Gangbang". Kristy clicked on the fourth video, titled "To be a sissy: Vikki", and made the video full screen. She then sat back on the bed behind Vikki as it started playing.

The title of the video appeared in hot pink, feminine letters on a black background: To be a sissy: Vikki. Then clips of the videos of her cumming on her face she'd sent to Kristy began playing, a blue subtitle in the same feminine font read: Her first taste of sperm. Then Vikki's first porn shoot with Mistress Jayla and her male slave began playing, focusing on her first taste of cock and another person's sperm with subtitles describing it. Then a clip of Jayla's large member entering Vikki's sissy pussy and the caption: Her anal virginity. Taken by BIG. BLACK. COCK.

Then a montage of clips from her nights at the gloryholes, pictures taken of her with the owner of the Utopian Cinema, and more video clips of her kneeling before a cock sticking out of a hole in the wall. And then portions of her first gangbang. As the personalized hypno video played, Kristy unlocked Vikki's chastity cage and let her little penis throb and drip precum as her sissy pussy clenched around the dildo.

Kristy left the room for a moment to grab her stainless steel tray and then placed it underneath the sissy to catch her leaking fluid. Then, leaving Vikki to watch herself be a cock slut, she grabbed her phone and searched for the number of sex counsellor and fellow Matriarchy Mistress, Sharon, in her contacts list.

"Good morning, Kristy. What's up?" she asked.

"Hey, Sharon. So, I was thinking of setting up a girls' night with you, me, and my sissy for the exchange program sometime next week to help her get more comfortable being feminine out in public. Could you spare some time for it?" Kristy asked.

"Of course I could. I'll need a few details first." her voice became difficult to hear, suggesting she turned away from her phone to talk to someone else. "Could you take some notes for me?" she paused. "Ok, Kristy. So what's her name and how long have you been training her?"

Kristy answered and Sharon was a little skeptical of the timing.

"Just one month...and you think she's ready to talk to a counsellor about transitioning? Has she been crossdressing in adolescence or have had feelings of being a girl before?"

"No to both, but I just planted the idea of her being a sissy in her everyday life and I just wanted you to help reinforce it in a social setting. Her femininity is connected with her sex drive and I'm limiting her male pleasure with chastity. I've even got her watching her first personalized sissy hypno now, but with some encouragement, she'll come around to accepting a new life as a full-time sissy."

"That doesn't mean she'll want to take hormones just yet. And she definitely won't want feminization surgeries for quite a while. You know these things take time and four weeks is much too fast for someone who was just a regular heterosexual guy."

"And yet, I got her to eat her own cum on the first night after she went home. And I got her to suck her first cock and lose her anal virginity in just two weeks. And just two days later, I got her on her knees in front of a gloryhole sucking and swallowing like three dozen strangers. And right after that, she presented her little ass to Drake right in his office." Kristy paused. "She's been to the gloryholes like six times and half of those, we walked through the parking lot and in through the front door with her fully dressed. She's even got a feminine pageboy haircut that's getting longer, had her third laser hair removal session two days ago, and she's following through with her workouts and corset training. She's moving fast because I have her wrapped around my little finger, but she'll need a little more encouragement from other Mistresses."

"Ok, ok...I'll admit getting a heterosexual guy to do all that in just a month is very impressive." Sharon thought for a moment. "Ok...we'll meet at Alyssa's Secret say, Wednesday around...eight?"

"Alyssa's Secret, Wednesday at eight. Sounds good! And thank you." Kristy said.

"Has she met Jayla yet?"

"Who do you think took her virginity?" Kristy giggled.

"Bring her along. It'll be good for her to talk about her transition."

"I will."

They said their goodbyes and Kristy went back to her restrained sissy, grabbing a small leather paddle on the way. The hypno was half over, but still had about eleven minutes to go. Sitting behind Vikki's exposed and penetrated rear, she grabbed the short pole that the dildo was connected to and began sliding it back and forth, fucking her with it. The sissy moaned and her penis twitched, a large drop of precum stretching its way to the silver tray beneath her. Kristy then slapped her right cheek with the paddle; one cheek and then the other. She repeated the swats to her rear every five to fifteen seconds, taking the time in between to caress the stiff leather against her reddening skin.

The hypno ended with Vikki staring into the camera while she was stroking a gloryhole cock as it exploded its sperm onto her tongue and into her hungry mouth and an overlaid caption that read: Welcome to sissyhood, Vikki. Then it faded to black.

Kristy gave her one more sharp spank with the leather paddle and asked, "So what did you think of your own personalized sissy hypno?"

"It was very good, Mistress. Your sissy looked like such a cock slut!" Vikki replied.

Setting the paddle down, Kristy took the sissy's hard little penis between her thumb and forefinger and began stroking in time with the movements of the dildo in her rear, causing Vikki to moan. "That's because you are a cock slut, sissy!" she giggled. "The way you eagerly drop to your knees in front of the gloryhole and suck and swallow every guy who comes to feed you just proves it!"

Vikki's penis suddenly stiffened, and Kristy took her fingers off while fucking her with the dildo harder. The sissy moaned in desperation as her milky white fluid drizzled out of her and pooled onto the metal tray underneath. Her little member quickly ran out of semen but continued to throb and twitch for another minute or two before it began to deflate.

Unlocking Vikki's neck, Kristy opened the stockade and removed the pole from the base, allowing her to bend down and lick up her mess. "Good, gurl, my sweet sissy pet." she said, praising the sissy's lack of hesitation.

Setting the stockade pole down, she put Vikki's chastity cage back on and then took the leather paddle back to the bench in the main basement room. Upon returning, Vikki finished licking the tray clean and Kristy removed the dildo from her sissy pussy and released her. To the Mistress' delight, the sissy remained on her hands and knees, turned around, and sucked the dildo clean without being prompted.

"That's another reason you're a sissy cock slut!" Kristy joked, giving her a hard, yet playful spank.

Vikki moaned, but kept her mouth closed and full until her oral cleaning duties were done. Kristy watched the little slut, thinking about ways to deny her even the few ruined orgasms she was allowed as she ordered her to clean each item they had used. Keeping her horny at all times would continue to make her dive more deeply into her feminization and stimulating her little penis reminded her of her malehood when she should be focusing on her sissy pussy for pleasure.

Having Vikki kneel on the small, cushioned pad once everything was washed and put away, Kristy said, "So, sissy...I got a text from a friend who's gathering a few Mistresses together for a girls' night out and I want you to join us."

Vikki hesitated. "You want Vikki to go out for a girls' night, Mistress?"

"That's right, sissy, but you shouldn't worry. We'll be going to Alyssa's Secret. Remember me mentioning it?"

"Yes, Mistress."

"It's called 'Alyssa's secret' because the owner is named Alyssa and her secret is that she's a transwoman like Jayla. It's a club for transwomen and their admirers." Kristy paused. "We'll be going on Wednesday, and you'll want to be here by five so we can go shopping and get you some clubbing clothes beforehand. After all, you can't dress like a slut all the time!"

Though she said she'd be willing to go to that club, Vikki still had some reservations about being a sissy in public. "Are there other sissies there, Mistress?" Vikki asked.

Seeing her hesitation, Kristy said, "Plenty of sissies go there too. And just like in Utopian Cinema and our porn shoots, who would recognize you? And if someone did, it's because they're at the same place as you for similar reasons. Maybe one of your coworkers likes cute little sissies like you!"

Vikki thought about it and realized that her Mistress was right again. No one she knows would be at a place like that (as far as she knows) and even if they were there, they wouldn't judge her in a bad way. They would just see that they have something in common.

Feeling a little excited about what Wednesday night might bring, Vikki bashfully smiled and said, "Your sissy would like to go, Mistress."

"Good gurl." Kristy smiled.

Going out in public to Alyssa's Secret was just another steppingstone in the sissy's training. Kristy would continue taking the sissy out to more and more places until she was comfortable being Vikki full-time. While her first time was going to be in a place full of transwomen and other various crossdressers, her subsequent outings were going to have to be normal, everyday places.

Most of them, anyway...

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AnonymousAnonymousover 1 year ago

I feel sorry for this kid. He needs to get out as a guy more, rather than be railroaded by a power hungry dyke who hates men.

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