The Sissy Exchange Program Ch. 02

Kristy had started all her emails to Vic with: 'My sissy Vikki...'

At first, he wasn't so sure about the sissy thing. After having masturbated the second time after his first night with her, he googled the term 'sissy' and found a lot of feminized men, wearing makeup and lingerie, bodies shaved smooth, and often bent over and taking something called a 'strapon' in their asses.

And then he got hard again.

And masturbated again.

His first 'My sissy Vikki...' email included a list of Mistress Kristy's rules and instructions to memorize them:

1. Always address as Mistress

2. Always be loving, faithful, loyal, caring, honest, trusting, committed, communicative, and passionate

3. Never argue with Mistress' decisions

4. Always speak in the third person: this one, your slave, your sissy pet, etc...

5. Never talk about Mistress or their relationship with others

6. If you are unsure of something, ask

7. Be pleasing at all times; no bad moods. Perfection of service and submission is the goal

8. Complete all instructions or punishments will follow

The same email included a video from her. Something called a 'sissy hypno' video. He was surprised that the ten-minute video starred Kristy herself, along with several sissies under her dominant authority. The clips were spliced together and didn't take place in her basement. Instead, it was a place that looked like a well-lit medieval bedchamber and dungeon.

Kristy whipped them and flogged them, they orally worshipped her pussy and ass and feet and strapon, and they also gratefully bent over and took the strapon like he'd seen on the internet the night before. Then, with a couple of fingers in their ass, they were given a handjob up to a certain point and then the stroking stopped. Kristy was clearly still working her fingers inside the sissies' asses and then their jizz just seemed to ooze out without any real orgasm. Then, after licking up their mess, their dicks were locked up in some kind of cage.

The instructions accompanying the video had told him to watch it without touching himself, and then to record a video of him cumming all over his face. And since he enjoyed eating his cum so much the previous night, he was to do it again.

He followed the instructions exactly and sent the video proving it.

Kristy texted him: That's my good sissy gurl 'kiss emoji'

The next several days were pretty much the same until the sixth night. The sixth email had an additional instruction: he was to shave his entire body and use the enema kit until everything came out clear the next day and be at her house at exactly seven in the evening.

Just to be safe, he got in the shower at four and shaved everything below his eyebrows. The instructions told him to be extra careful around the ankles, knees, wrists, and elbows. Everything else was just about not moving the razor sideways like with his face.

Except his balls. That area, he had to stretch the skin and make it taut.

When he got out, he looked at the time and saw that it was five-thirty. He opened the box she had given him the first night and read the instructions on how to use the enema kit. He filled the bulb, screwed on the end, and then very carefully inserted it into his rear and squeezed the bulb. After emptying everything in the toilet, he repeated the process until it came out completely clear.

It was five-fifty.

He had a twenty minute drive ahead of him, so that left him with fifty to get dressed and leave. Or that minus ten, just in case. She told him exactly seven, but it couldn't hurt to be early and wait in his car. Better than being late.

He dressed in his pink, sissy panties, jeans, t-shirt, socks, and shoes. He probably wasn't going to be wearing much of anything after he got there, so nothing extravagant. He got in his car and opened his phone's GPS for her address. The drive was twenty-five minutes, so he had to wait fourteen minutes when he got there. He then walked up to her front door and raised his hand to knock.

The door swung open. "Hi there, sissy gurl." Kristy smiled. "Did you miss me?"

She was wearing high heels, stockings (probably thigh highs), a latex skirt, and a corset. All black. Her makeup was light like the last time he'd seen her, and her lips were bright, ruby red. Her hair wasn't in a braided ponytail this time; it was hanging loose with some behind her back and some over her shoulders.

He smiled back, excited. "Yes, Mistress."

"Good. And from now on, when you're early, I want you kneeling in front of my door."

"Yes, Mistress."

She invited him inside and told him to strip because sissies never wear male clothing in her house. Once he was down to his panties, she put a collar around his neck and led him downstairs by the leash. He was allowed to walk on the stairs, but was ordered to crawl everywhere else.

The basement was the same as before, with several bondage furniture in front of the wall covered with mirrored panels. The bench with drawers and a sink was on the left and the pegboard with whips and floggers were above it. And she even set the pad he had knelt on in the same spot as a week ago.

He instinctively crawled to it and knelt with his knees apart and his hands palm down on top of them. Kristy smiled at that. A fast learner, she thought. She hoped that watching her sissy clients take her strapon had caused the idea of 'him' being one of those sissies take hold in his sexuality. Or at least his curiosity.

Though, it hadn't worked with some of her other Sissy Exchange subjects.

"Do you know why I had you shave your entire body and use the enema kit I gave you last week?" she asked, standing behind him and looking into his eyes from across the room through the mirror.

"To make your slave into a better sissy, Mistress." he replied.

"That a good guess, and that's part of it, but no." she paused, placing a hand on top of his head. "I had you do it so we could bring your inner sissy out into the real world. I'm going to train you to bring Vikki out and serve your superiors."

After their first night together, he thought maybe she was interested in a relationship, but after thinking about it, he thought maybe she like him more as a customer, given that she did this whole "femdom" thing for a living, but the fact that she wasn't charging him made him confused. And the word "superiors" made Vic wonder even more.

"May your slave ask a few questions, Mistress?"

"Yes, my pet?"

"What do you mean by 'superiors'? Am...is your slave going to serve other Mistresses?"

"Oh, yes, my pet. During and after your training, your sexual experiences will expand and vary. Much more than if you hadn't met me."

"You do this for a living, but why aren't you charging your slave?"

She knelt behind him, wrapped her arms around his chest, and whispered, "Every once in a while, I go out to find a special kind of guy for a special kind of project. I think you're that special kind of guy. You caught my eye immediately."

"What's the special kind of project?"

"You've seen my sissy hypnos."

"How far will this project go?"

"Let's find out together." she kissed the side of his neck and stood.

She went to the bench and retrieved a pair of latex gloves, a small bottle of lube, a small bag of something black, a small pink vibrator, and a small stainless steel tray. She decided to leave her strapon harness and her favorite dildo in its place in the third drawer so she can make him think that starting his anal training at that point was his idea. When they thought it was their idea, they were more willing to follow through with it.

She placed the items on the tray and took them into the bedroom behind him and returned after a minute. Taking his leash, she led him into the room and onto the bed, on all fours and facing the wall-mounted TV with the metal tray underneath him.

As she attached the bed restraints to his wrists and ankles, he looked at the small plastic bag on the dresser under the TV to figure out what was in there. Then he noticed the wireless keyboard and mouse on the dresser that he hadn't seen the week before, probably because he was either crawling on the floor or his attention was otherwise diverted while Kristy was naked. Or both.

Once he wasn't going anywhere, Kristy pulled his panties down to his knees and out of the way. She then turned on the TV and it was like the desktop of a computer. She opened the videos folder and then opened another folder labeled "Sissy Exchange". Then there was another folder titled "Milking Sessions". She selected the first video and clicked play. Grabbing the gloves, the lube, and the pink vibrator, she made herself comfortable on the bed behind him.

While she put on the gloves, the video began playing. It opened up with the title "Orgasms Must be EARNED", then Kristy and another Mistress appeared in the same kind of medieval bedchamber/dungeon. She was older than Kristy, but still just as sexy. She was a little taller, very blonde, and she kept herself just as toned.

Vic wouldn't mind serving her, too.

The two Mistresses on the screen began fondling a sissy's balls and dick while she was on her hands and knees on the bed with her wrists and ankles restrained. The same position he was in. The sissy was wearing pink thigh highs, a pink bralette, white heels, and had her makeup done heavy, but well. They were using gentle touches and strokes, commenting on how hard she was.

There was the click of a lube cap and Kristy's fingers rubbing the slick liquid between his cheeks and rubbing circles around his hole. His own dick hardened like the sissy's in the video, but it remained untouched. Then she inserted a finger and both his penis and his hole tensed up. In a good way. In a way that caused a soft moan escape his lips.

As she applied some downward pressure to a sensitive spot inside his ass, the unknown older Mistress in the video put on her own latex gloves and applied a helping of lube to the fingers.

"Does sissy Jasmine want her pussy fingered?" she asked.

"Yes, Mistress Kelly!" the sissy replied in a husky, yet feminine voice.

Kristy suddenly inserted a second finger into his rear and her other hand softly rubbed and stroked his balls. The scene progressed to the point where the sissy was being finger-fucked by Kelly with Kristy's fingers wrapped around both the sissy's dick and balls. And at that point, real-life Kristy wrapped her fingers around 'his' dick and balls, causing him to moan.

A large drop of precum formed at the tip of his mushroom head and then gravity slowly pulled it down toward the silver tray. The drop stretched and elongated until it connected Vikki to the tray. She continued the prostate massage and coupled it with a few slow but firm strokes downward with her other hand. Like milking a cow.

In this case, milking a sissy.

"Would sissy Jasmine like to be fucked?" Kelly asked in the video.

"Yes, Mistress, please!" the sissy answered.

"Would sissy Vikki like to be fucked?" real-life Kristy asked. "Or is it too soon for you?"              He hesitated. He wasn't sure and, speaking in the third person, he said so. "That's ok. I'll warm you up with my vibrator and ask again later."

While video Kristy began donning a strapon with a dildo that resembled a big black cock, the low hum of the vibrator filled the air and he felt it rub against his hole. The new sensation was a pleasant surprise; one that made his dick tense and leak another large drop of precum onto the tray. Real-life Kristy teased him, gently poking his most intimate spot, almost penetrating him, then back to rubbing along the crevice between his cheeks.

Then she pressed the tip into him and slowly eased it inside, breaking down the resistance of his tightening and loosening hole. She told him to push out, saying that it would enter much more easily and pleasurably, so he did. And it slid several inches inside. He closed his eyes tightly and gasped. The vibrations made it so he wasn't quite reacting to pain, but from a new sexual experience. One that cause his dick to tense up again and spill another large drop of precum.

"Good sissy gurl..." Kristy purred.

He heard the sissy in the video squeal in pleasure and knew she had also been penetrated by Kristy. As she video Kristy sensually bucked her hips and thrusted into Jasmine in the video, real-life Kristy aimed the tip of the pink vibrator at a downward angle against his prostate as she pumped it in and out of him.

Hearing an almost feminine moan escape from his lips, Kristy smiled. "Feels good, doesn't it sissy Vikki?"

"Yes, Mistress..." he replied breathlessly.

She still had a hand around his member with her thumb behind his balls to add to the stimulation. "What do you think about sissy Jasmine? Does she look sexy in her lingerie?"

He looked up and watched as Jasmine took the realistic black dildo from Kristy's thrusts. The camera changed views to get the whole picture from a left side view. Kristy was behind Jasmine while she was on all fours and Kelly was on her right, holding the sissy's dick but not stroking. From the side, Jasmine looked like an attractive, flat-chested woman in a lesbian scene.

His dick tensed in Kristy's hand.

"That seems like a 'yes', but I want to hear you say it, sissy."

"Yes, Mistress...sissy Jasmine looks sexy."

"Do you want to look sexy like her, sissy Vikki? Do you want to feel silky-smooth stockings and lace on your skin?"

He had thought about being in the same positions as the sissies in the videos she'd sent him while masturbating, but he wasn't sure he actually wanted to. Not afterwards.

But when he was horny...

"Yes, Mistress." he said softly.

Kristy smiled. "What was that sissy? Speak up, sweetie..."

"Yes, Mistress...sissy Vikki wants to look sexy for you."

Her smiled grew wider. He was already thinking of himself as Vikki, at least in her presence. That's no surprise, given that she's his sole outlet for non-solo sexual pleasure. The trick was to manipulate him into thinking of herself as sissy Vikki in her everyday life.

"I'm glad to hear it, my sweet sissy pet..." Kristy cooed, giving his throbbing organ a few short strokes.

Precum oozed out and gently fell to the small pool that had formed on the stainless-steel tray. She continued sliding the pink vibrator in and out of her sissy pussy, pressing it against her sweet spot. Her penis was at its hardest for longer and longer periods of time, suggesting that Vikki was getting closer to releasing her cummies. And her near-constant moans were excellent corroboration.

"Do you want to cum for me, sissy Vikki? Do you want to show me how horny you are by releasing your sissy cummies?" she asked.

"Yes, Mistress!" she gasped.

"Tell me my sissy pet will be a good gurl."

"Your sissy pet will be a good gurl!"

Vikki's voice trembled in the cusp of ecstasy. Kristy knew the signs. Everyone was a little different, but she knew what to do and when to do it based on their reactions and how they felt in her hands. The pace in which she fucked Vikki with the vibrator and its angle remained the same, but her other hand suddenly gave several quick strokes and Vikki cried out.

Then she released the sissy's clitty.

The anal stimulation kept her on the edge of orgasm for another few seconds and then it faded away, allowing her semen to freely flow out of her and onto the silver tray. Vikki's breath shook as she squeezed the bedsheets, whimpering in frustration from being so close and then pulled back so quickly. Kristy continued her work with the vibrator for another several minutes before pressing the button on the back, turning it off.

She pulled it out of Vikki's pussy and walked to the foot of the bed, smiling into her dark eyes. "Very good, sissy Vikki...you've been a good gurl so far." She pulled the tray toward her and added, "Continue being a good girl and lick up your mess."

Drained of her sperm, Vikki no longer felt the need to orgasm, but was still horny somehow. It was another new experience. And it made her even more eager to swallow her cum.

"Yes, Mistress!" she said and began licking.

Kristy watched as she lapped up and swallowed every drop. A smile formed at the corner of her mouth as she though about how far she'd come after just two sessions. The sissy was either already bi-curious or was more desperate for female attention than she'd originally thought.

And that made everything so much easier.

Vikki looked up into her Mistress' pretty blue eyes when she licked the tray completely clean and was rewarded with a soft kiss on the lips. "Good sissy gurl." Kristy held up the vibrator with the tip pointing at the sissy's parted mouth. "Now open up and suck the vibrator clean."

Vikki was unsure of that, but her horniness and lack of sexual release overrode her judgment. She opened her mouth, and her Mistress slid the pink phallus inside. Her lips sealed themselves around the shaft and she formed a suction. Her cheeks caved in as Kristy pulled the vibrator back and then her cheeks puffed out as Kristy pushed back in.

"Are you using your tongue, sissy Vikki? Are you pressing it up against the underside of the phallus? Swirling it around the tip?" Kristy half asked, half instructed.

Vikki nodded. Probably that she was starting to, but it didn't matter. She was going to learn how to use her tongue to pleasure cock. Along with her lips and throat. In the meantime, though, she was going to practice on Kristy's favorite dildo.

With the vibrator sucked clean, Kristy set it on the tray and collected the bottle of lube. After taking it over to the bench in the basement's main room and removing her wet latex gloves, she returned just in time for Jasmine to beg to cum on TV. She stopped the video and turned it off. After releasing Vikki's wrists and ankles, she had her lay on her back with her legs spread like a good little slut.

She then grabbed the small plastic bag and knelt between the sissy's legs, dumping out the contents on her stomach. They were a bunch of black plastic rings and a narrow six-inch ruler. She grabbed the rings one-by-one, eyeing the size in comparison to the circumference of Vikki's flaccid penis, around the base and around both the base and her balls. The larger one she had, she slipped each sensitive orb through and then her penis. It was a snug fit, but there was just a tiny bit of room.

"How does this feel, sissy? Is it comfortable?" Kristy asked.

She didn't respond right away and instead concentrated on how it felt. "It's comfortable, Mistress."

"Any pinching?"

"No, Mistress."

"Good." Kristy said to herself, and then slid the penis through the smaller plastic ring. "How about this?"

"It's comfortable, Mistress."

"Good."

She removed the two plastic rings, measured the flaccid length of her penis with the ruler, and then collected the unused rings, put them in the bag with the ruler, and went back to the bench. She put the bag back in its drawer and left the two rings of the right sizes on the bench's surface and made a note of the length on her phone. She then returned and took Vikki's leash.

"Come, sissy." she said.

Vikki crawled off the bed and was led to a stockade in the main room. It was different than the one she was put into the last time. It was made of the same wood with dark brown stain and lacquered to a high finish as everything else, but it had an 'H'-shaped base with a 'T' standing at the middle. The three holes at the top bar of the 'T' was identical to the sawhorse stockade, so Vikki knew what to do.

When Kristy opened the top half of the stockade, Vikki got on her feet and bent over, lining up her neck and wrists for the three holes so Kristy could close it down and effectively lock her in place. Kristy then walked around the sissy, caressing her hand across her smooth skin, occasionally dragging her manicured nails and leaving thin red scratches here and there.