The Sissy Exchange Program Ch. 02

After retrieving a crop, Kristy positioned herself behind and to the left of Vikki's exposed and vulnerable rear. "You look so sexy from this angle, sissy." she teased, looking into her eyes through the mirror.

"Thank you, Mistress." she replied.

"The only thing that could make you look sexier is a pair of sheer stockings, heels, and a garter belt." she paused to caress Vikki's right cheek with the end of the crop. "A wig and pretty makeup would make you perfect."

She struck the sissy's rear with a sharp, sudden blow, just enough to earn a yelp. Kristy dragged the crop's leather patch across more smooth skin and down the crevice that led to her sac. A few playful taps against the orbs inside and then a sharp thwack! on the left cheek.

"You have such a cute ass, Vikki." Kristy said, striking the right cheek again.

"Thank you, Mistress." Vikki replied.

"It would look so much sexier with my strapon buried between those cheeks." she paused. "Don't you think, Vikki?" Just as her sissy pet was about to respond, she struck just below the left cheek, earning a yelp instead. "What was that sweetie?"

"Yes, Mistress."

"Yes?" Kristy asked. "As in, 'yes you want me to grab my strapon and take your sissy virginity'?"

Thwack!

Vikki's erection had already returned and the notion of having more anal stimulation seemed very appealing to her. "Yes, Mistress! Take your sissy slave's virginity!"

Kristy smiled. Vikki is almost too easy, she thought, giving her several rapid swats in various places all over her vulnerable rear. Vikki moaned and groaned, half in pain and half in pleasure, and Kristy gave her one last harsh strike to elicit a whimpering yelp.

Just to push her boundaries.

Walking over to the bench, she set the crop aside and retrieved her strapon harness. She then removed her latex skirt, revealing the glistening lack of panties, and then stepped into the harness. Before tightening the strap around her waist and the ones that looped up and around the bottom of her lush ass, she grabbed her favorite black dildo and slid it through the metal ring at the harness' crotch.

As she tightened everything firmly in place, she thought about Jayla, a fellow Matriarchy Mistress. Her long, smooth hair, the pretty face with lush lips, and the firm, toned muscles under her dark skin. Kristy's hand found its way to the phallus and the fingers wrapped around the shaft, remembering the last time they'd been in bed together.

And her intimate folds became even more damp.

She put on two more latex gloves and took the bottle of lube. Walking back to her sissy, she positioned herself so the dual-density silicone phallus was just in front of her face. "You're lucky, my sissy pet. You get to experience my favorite dick tonight." she paused. "Good gurls get fucked, but first they must awaken the sexual desire with their lips and tongues. Can you do that, sissy Vikki?"

The sissy looked at the dildo strapped to her Mistress' pelvis. It was dark brown with a lighter brown, mushroom-shaped head that looked a little smaller than it should for the nine-inch length and nearly two-inch girth. Vikki had watched porn and knew what women did for their man before sex and, though she wasn't exactly dressed for the part, she was a sissy for the night. And that meant she was the woman during sex.

And that meant she opened her mouth and licked the tip of the head.

Kristy smiled and put her hand on the back of Vikki's head. She moved closer, sliding the first two inches passed those hungry lips and let her get used to having something to suck on.

"Don't forget to use your tongue, sweetie." Kristy softly said with a hint of lust.

When Vikki moaned, Kristy began a rhythm of slow and gentle thrusts. Just an inch forward at a time. She could see the sissy's cheeks suck in and puff out, and then she imagined her lips painted red and wrapped around the real thing. Then she felt a drop of her arousal roll down the inside of her thigh at the thought.

"Now stretch out your throat like saying 'ah'." she said. She slowly rocked her hips forward until Vikki's forehead was pressing against her lower abdomen and stayed there. The sissy gagged and Kristy pulled back, leaving only the tip in her mouth. "Good gurl. Not bad for a first try, but we'll definitely have to work on your cocksucking skills."

She slipped her dildo out from Vikki's lips and wandered around to her rear, reddened by the crop. After pouring lube down the sissy's crevice, Kristy rubbed the phallus along it, teasing Vikki. She poured more on the dildo and stroked it, smearing the lube all over until the entire thing glistened in the light.

Pressing the tip to her rear entrance, Kristy said, "Just like with the vibrator; relax and push out."

She glanced at the clock near the pegboard and saw that it was 8:02.

The dildo was longer and wider than the pink vibrator, but she took her time entering the sissy's pussy. She pressed forward an inch, then backed off. Pressed forward again, this time a little harder, then back. On the third time, the head of the phallus opened up Vikki's hole, causing her to gasp with a low, soft moan. Kristy continued going deeper a quarter inch at a time. Never stopping. Not until her pelvis pushed hard against the silky smooth skin of Vikki's ass.

Leaning forward until her front rested on Vikki's back, Kristy wrapped her arms around her and said, "You've taken the entire thing, sweetie." She kissed between Vikki's shoulder blades. "How does it feel to have cock inside your pussy?"

Vikki's breathing trembled for a moment before she said, "It feels good, Mistress."

Kristy smiled to herself. She's going to be one hell of a slut when I'm done with her, she thought.

She ground her hips in circles for another minute or two and then asked, "Is my sissy pet ready to get fucked?"

"Yes, Mistress...please fuck me..." she said in a cloud of pleasure.

For a short moment, Kristy thought about admonishing her for not referring to herself in the third person but decided not to break the momentum of Vikki embracing her sissyhood. Instead, she rocked her hips back until the dildo was halfway out, and then slowly thrusted forward. A nice slow fuck to break her in; almost like making love.

For now.

Kristy's eyes watched as it sank inside Vikki and then reemerged a few seconds later. Dropping the small bottle of lube to the floor, her hands caressed the warm, red skin. Her ears listened to the low whimpers and moans escaping Vikki's lips. Her clit almost imperceptibly rubbed against the padded front of the harness behind the base of the dildo. Her mind became drunk with the power of turning an otherwise straight male into a sissy cock slave.

And her folds dripped with arousal from it all.

Despite not having a cock of her own, she instinctively began pumping faster and harder. Her strapon was owning Vikki. And bringing out her inner femininity with every thrust. Vikki's lustful moans were proof of it. Kristy grabbed a hold of the sissy's hips so she could go from owning to dominating.

Mistress Kristy LOVED her job.

"Who's my little sissy whore?" she asked, bringing Vikki's mental state to where she wanted it.

"I am, Mistress!" she gasped.

"Are you my little cock slut?"

"Yes, Mistress!"

"Does cock own your little pussy?"

"Yes, Mistress!"

"Good sissy gurl." Kristy gave her a firm swat on her right cheek and continued fucking hard.

Vikki closed her eyes and tightened her hole around the welcome intruder. Her dick was hard and swaying to and fro, desperate for attention. Though she wasn't dressed the part and had no makeup, in her mind at that moment, she was a feminized sissy. Taking her Mistress' cock up her ass and loving it. Kristy had promised that her sexual experiences would expand and vary in the world of femdom.

And she was right.

Her skin still stung and who knew pain could be so pleasurable? Her masturbation was always straight to the point, and yet the alternative sexual stimulation while ignoring her dick enhanced her arousal. And the alternative sexual stimulation itself: being fucked in the ass. The dildo was grazing a sweet spot inside her and she arched her back, so it was hitting more direct.

Kristy saw the movement and smiled. She's going to be a great cock slut, she thought. "Taking cock feels so good, doesn't it sissy?"

"Yes, Mistress!" Vikki moaned.

"Continue being a good sissy gurl and you'll get all the cock you want."

Kristy slapped her ass and leaned forward. She continued humping her strapon into the sissy's pussy, but felt she deserved a little reach-around as a reward. Her nimble fingers wrapped around Vikki's little dick; thumb and index finger at the base with the pinky at the head and felt the organ twitch. Kristy slowly moved her hand up and down for a minute but stopped when the sissy clitty had tensed up without relaxing.

It was a descent sign she was nearing orgasm and Vikki's whimpering groan seemed to corroborate it.

"Not yet, my sissy pet. Continue being a good gurl and you'll earn an orgasm tonight." Kristy said sweetly.

"Yes, Mistress." Vikki replied.

Kristy straightened up and looked at the clock on her wall near the pegboard. She had been pegging Vikki for just over twenty minutes, which was longer than most guys would last during sex, so she figured she would fuck her sissy pet for five more minutes or so. She deserved it for being good, after all.

She could've gone longer, given her athleticism and practice, but she stopped at 8:30 and slipped her dildo out of the well-used, gaping sissy pussy. She then gave Vikki a few harsh spanks and walked around to present her strapon to the sissy's lips.

"All good gurls suck cocks clean after being fucked." Kristy said.

"Yes, Mistress." Vikki replied, parting her lips and accepting the glistening dildo into her mouth.

"You are such a good gurl tonight, sissy Vikki."

Kristy lovingly caressed Vikki's head and face as she gently thrusted back and forth, watching those cheeks puff in and out again. Once the dildo was clean, she pulled out and walked over to the bench where she removed the strapon harness and separated it from the dildo. Setting them down on the bench and removing her gloves, she walked back over to her sissy pet and let her eyes drink in the sigh of Kristy's dripping wet pussy and rose bush tattoo on her left hip and thigh.

Kristy then fingered herself slowly and deeply with her index and middle fingers. Just enough to coat them in her juices. Vikki watched, hornier than ever, and nearly drooled. Removing her fingers, Kristy scooped up some excess fluid and then let her sissy pet suck her fingers clean.

"Does your Mistress taste good, sissy?" she asked.

Vikki nodded, but continued sucking. Clearly enjoying the taste of feminine arousal. After another minute, Kristy removed her fingers and opened the stockade. Taking a hold of the sissy's leash, she walked her back into the bedroom and had her crawl onto the bed.

"Before I reward you with an orgasm, sissy, I need you to buy a few things for our next session." Kristy said, turning on the TV and then getting online.

"What things, Mistress?" Vikki asked.

"You'll see, my sissy pet."

Vikki laid on her side on the bed and watched as Kristy opened up a few websites that were saved in her favorites. One was for high-quality, low-priced wigs, another one was for the same kind of dick cages she'd seen sissies wear in Kristy's videos, and the third one was for makeup kits.

She added the makeup kit to the cart, then went back to the bench to retrieve her phone. Looking up the measurements she noted, she went to the chastity cage website called 'lockedinlust.com' and viewed a size chart. She then selected the mini, chose the color pink, and added to cart. She then went to the wig website and turned back to Vikki.

"Let's pick out your hair style, shall we?" she said.

They went through all wig styles in dark brown, which matched Vikki's hair color, and settled on a medium length wig that became curly halfway down and would reach Vikki's shoulders. She added it to the cart and then added up the subtotals from each website's order.

It added up to just over $600 without taxes or shipping and handling.

"Can you afford that, my pet?" Kristy asked.

Vikki looked down, partly disappointed and partly embarrassed. "No, Mistress." she quietly replied.

"We can't proceed with our special project without them, sissy." Kristy said, adding, "But there is something you can do to pay for it. And it would help you find your sissy self."

"What can I do, Mistress?"

"What can I do?" Kristy playfully admonished.

Vikki winced. "Sorry, Mistress. What can your pet do to pay for it?"

"That's better, sissy Vikki." Kristy paused. "You can help me at my work, but you'd still have to dress the part. Which means we'll have to go shopping to get you some feminine clothes."

"Yes, Mistress. What would your pet do to help you at work?"

Kristy cryptically smiled. "You've seen my videos. There's some behind-the-scenes work you could do, among other things. We'll see how it goes." she crawled onto the bed. "Now lie back."

Vikki complied and had her wrists and ankles restrained once again. Kristy went back to the bench, got one latex glove, and picked up the bottle of lube where she dropped it while pegging her sissy pet. She returned to the bed and positioned herself between Vikki's legs. Applying a few drops to her gloved hand, she inserted two fingers into the sissy's pussy and curled them upward, right against her prostate.

Vikki's member reawakened and Kristy locked her beautiful blue eyes on her sissy pet's darker ones. Then, with parted red lips and a hint of tongue showing, she lowered her head and took Vikki's throbbing clitty into her mouth, sealing her lips around the base. The sissy gasped in pleasure, feeling the warm wetness of oral sex for the first time. Kristy swirled her tongue around the head and then pressed it hard against the underside as she began bobbing her head up and down.

Vikki arched her back and rocked her hips, trying to make the most out of the experience. Kristy placed her other hand on the sissy's pelvis to help control her hips as she continued fellating her organ. Less than a minute later, Vikki tensed up and then bucked her hips uncontrollably, moaning out her sexual bliss. Kristy kept her lips sealed around her shaft and sucked out every last drop Vikki had.

Pulling out her fingers and lifting her head with an audible plop from her lips, Kristy kept her lips shut as she crawled over her sissy pet. Planting those lips over Vikki's, she parted them and let the semen flow down her tongue, to the sissy's, and into her mouth. Vikki's first cumkiss.

She swallowed her cum and they continued making out for another few minutes until Kristy pulled back and stuck her gloved fingers into Vikki's mouth for her to suck on. Once clean, she removed her fingers, got off the bed, and put the bottle of lube and used glove on the bench's counter top. Returning, she released the sissy and took her leash to lead her to the bench where she was told to wash the strapon harness, dildo, crop, collar, plastic rings, and ruler. Then Vikki was made to crawl over to the stockade they'd just used and use an anti-bacterial wipe to clean the floor where her precum could've dropped.

Once that was done, and all the cleaning supplies taken care of and the wipe and the gloves were thrown away, Kristy grabbed a box from one of the drawers, handed Vikki her panties, and had her crawl behind her as they went back upstairs where Vikki dressed and returned to Vic.

"Everything should arrive by next Saturday, so expect to be back next week." she said. "I'll let you know a time, but it'll be much earlier than it was today." she then handed him the box. "In the meantime, I want you to use this when you masturbate from now on." He took the box and she said it was a buttplug, explaining that sissies are only allowed to cum with something that filled their pussies.

Kristy then gave him a kiss good by.

After he left, she went back downstairs and logged in as a distributer to each of the websites, and placed the orders, getting a forty percent discount on everything. Then she thought for a moment. Things were going well with Vikki. And they were moving faster than Kristy anticipated. The last Sissy Exchange subject she trained took three weeks before she was comfortable enough to swallow her own cum.

Vikki did it on her first night.

Without Kristy being in the same room.

Because she was told via text.

Since Vikki was excited about bringing her sissy self out into the world, at least with Kristy, she might be willing to start her corset training early. To slim out her waist and create more of an hourglass figure. Kristy was sure Vikki would do almost anything her Mistress told her. And she hadn't even let Vikki's cute little clitty inside her pussy yet. Perhaps she could get the sissy to focus her attention on cock with the only taste of pussy coming from her fingers.

She decided to take Vikki's measurements for her first corset during their next session.

Then she typed up an email for Vikki with instructions to continue growing out her hair and to start going to the gym. She added a list of workouts that focused on her legs and ass and told her to use her phone to record herself as proof she was following her Mistress' instructions.

Kristy then attached a video of herself with a male sub and a sissy. The sissy was obviously on the bottom of the hierarchy, holding Mistress' whip or cane with her teeth, always on her knees, almost treated as if she wasn't there. Kristy chose this one because at the end, the sissy was the one who rewarded the male sub with oral sex. Completed to orgasm, showed the camera her mouth full of sperm, and then swallowed everything. Instructions for the video obviously included Vikki recording a video of her own, cumming on her face, scooping it all into her mouth with a finger, and then swallowing everything.

Just like the sissy in the first video.

And she was to send a new video of self-facials every day of the week.

She hit send, turned off the TV, and went upstairs to her bedroom where she undressed and texted Jayla.

Kristy: I got my sissy to agree to help out at work

Kristy: She should be ready on Saturday

Kristy: Do you have a client that earned an oral reward

Jayla texted back five minutes later: I'm sure I'll have one by then. Do you have a pic yet?

Kristy: Not yet but I will Saturday

Kristy: She'll look very pretty when she's all done up tho

Jayla: Good to hear; I look forward to meeting her!

Kristy: She does too she just doesn't know it yet

Jayla smiled, replying: They never do!

The ebony Mistress set her phone down and returned to her current client. He was a pale-skinned man, early forties, and a local politician. His hands were tied together and strung up by a silk rope that ran through an eye bolt in the ceiling with the other end tied to another eye bolt in the wall. He was naked and his toes barely touched the floor.

She stood behind him at just over six feet tall, thanks to her natural height and high heel, thigh high boots, and was wearing an underbust corset. No bra, no panties. Her d-cups weren't natural, but they were beautiful, and she loved to show them off. That and her nine inches of hard throbbing girl dick.

She held her forty-inch-long whip with seven separate leather straps on the end and asked, "Now where were we, mister mayor?"