The Sissy Exchange Program Ch. 11

It took about two weeks, but Vikki had finished moving in with her Mistress. It wasn't that she had a lot of things to move (she really didn't), it was that the landlord insisted that she pay the remainder of her year-long lease in full before she moved out and it took a little time and help from Kristy to sort out his unreasonable demands. Although, 'sort out' doesn't quite describe it.

Kristy used her feminine charm to negotiate an alternative, rather than point out that, in Vikki's lease, her moving out before the lease expired simply meant that he got to keep the security deposit. That alternative was in the form of Vikki, appearing before the man in her fully femme self, serve as his sex slave for an evening. At first, he said he wasn't gay and that he'd only consider it if Kristy were his slave, but when she showed him some of the sissy's porn videos, he wanted to see Vikki in her maid's outfit for himself.

And that's when he agreed to Kristy's deal.

The landlord wasn't an unattractive man, and his own apartment wasn't dirty, so Vikki wasn't against being his slave for a few hours. In fact, she thought it was kind of hot to 'pay her bills' with her sissy maid services. So, wearing a short-sleeved black mini dress with a white apron around the front, a white petticoat underneath the skirt, white sheer thigh highs with a black garter belt, and her black four-inch heels, along with her dark eyeshadow, mascara-enhanced long eyelashes, and bright red lips, she was ready to serve him in any way he wanted.

And she did.

She started by cleaning his dishes while he watched her from his living room; his eyes staring at her sissy ass more than anything else. When she had finished drying the last plate, he was standing behind her. He bent her over the counter and pressed his groin into her rear, his firm erection obvious to the excited Vikki. His hands felt her up, lifting the skirt of her outfit until her smooth, pale cheeks were out in the open.

And he saw that she wasn't wearing panties.

He squeezed and caressed her firm globes and then put a finger into his mouth, wetting it. Then he took that finger and slid it between her cheeks and into her hole. She tightened it around his digit, and he sawed in and out of her for a minute before pulling it out and making her suck it. Since she kept herself clean with enemas and adjusted her diet to make it much faster and easier, she eagerly wrapped her lips around it. He then pushed her to her knees and fished out his six-and-a-half-inch cock.

She eagerly wrapped her lips around that too.

Swirling her tongue back and forth along the underside as she bobbed her head on the hard organ, she moaned her love of being put into her place by a man. The landlord, not expecting such a skilled cock slut from someone so young, hovered his hand over her head, unsure whether to lovingly caress her hair or firmly hold her in place for a throat fuck. In the end, he decided that, because had a few hours with her, he let her control the pace and simply enjoyed himself.

His fat, mushroom-shaped head slid in and out of her throat, stimulating the sensitive nerves there and made the man involuntarily tense and twitch on occasion. His hand stopped hovering and dropped to her head, gently caressing the sissy maid. They made eye contact for a moment before his gaze went to her red lips tightly sealed around his manhood, making him harder for a few split seconds. Looking back into her eyes, she almost looked like a sweet and innocent little girl that was being corrupted by his sexual lust.

He just had to bury himself in her tight little ass...

Lifting her up to her feet, he spun her around and bent her over his kitchen table. Bunching the skirt of her outfit in one hand and exposing her rear, he spanked her once. Then twice. Then he pushed her right cheek aside and pressed himself into her star, easily splitting her open and impaling her to the hilt.

Vikki wrapped her fingers around the opposite edge of the table as her former landlord basked in the pleasure of her sissy pussy, clenching her hole down around him. He pressed a hand down on her back, resting his weight on her as he ground himself in slow circles before pulling slightly out. Spreading her cheeks, he watched as his member disappeared inside the warm, wet anus and then reappeared. His humping was slow and deliberate, not just for his visual entertainment, but also for making the experience last.

The taboo nature of fucking a slender young man dressed up as a sexy maid created one of the most exciting experiences of his life, but it also made it that much easier for his orgasm to begin approaching, and so soon. He only had her for a few hours and his first orgasm was almost there after only a few minutes.

But it was a hot few minutes...

The thought of seeing her with his cum splattered all over her girlie face suddenly flashed across his mind, so he picked up his pace and began pounding her. For all of twenty seconds, anyway. Then he pulled out and roughly put her on her knees while he stroked himself. Pointing his organ straight at her pretty red lips, he loudly grunted and sprayed a dozen droplets of semen over her with his first shot. Then a powerful spurt that splashed against her cheekbone. And two more; one on her forehead and the other onto her outstretched tongue. Once he was down to the last few pulses, he slipped between her parted lips, and she sucked the last throes of sexual climax out of him while looking into his eyes.

Spent, he removed his deflating member from her mouth and just stared at the beautiful sight of the sissy with her cum facial. Then she began smearing the thick, milky fluids across her skin and to her lipstick smeared lips. Finishing off the last few drops, she opened her mouth and showed him his seed mixing with her saliva for a moment before swallowing and licking her lips.

"Mmm, thank you!" she smiled.

Her eager sexuality forced a partial laugh out of him, and he replied, "Give me a few minutes and I'll give you some more."

"Shall your sissy maid clean your bedroom while she waits?"

His smile grew wider. "Absolutely."

There wasn't much cleaning for her to do, but she did bend over several times as she pretended to look for something to pick up and that was enough for him. Removing his pants, underwear, and shirt, he looked into her eyes when she turned around and began stroking himself. Vikki stepped closer and a part of him wanted to kiss her, but he chose not to, since she recently had his cum all over her face and lips. Instead, he pushed her to her knees and slapped his dick against her cheek and outstretched tongue.

She looked up at him with submissive eyes and an eagerness to please, and then dove onto his erection until her chin pressed against his balls. Remembering her deep throat skills, her landlord grabbed a fist-full of her hair and began thrusting hard and fast. The room became filled with 'glucking' noises as her gullet gave way to his thick tip and saliva quickly began spilling out of the corners of her mouth. Though she could handle it, her eyes watered and tears flowed down her cheeks, further ruining her mascara and making her look like a hot mess.

A hot and sexy mess, at least in the eyes of her landlord.

Pulling her into him so her nose was buried in his pubic hair, he gave her a few firm slaps to the face. "You're such a fucking trap slut, aren't you?" he rhetorically asked.

She answered by maintaining eye contact and nodding, and then he pulled out of her throat and slapped her once more, causing her to yelp. Man-handling her to her feet and then tossing her face-down onto his bed, he roughly bunched the skirt of her outfit up to her lower back and quickly penetrated her rear. Turned on by the enhanced aggression, Vikki moaned and gripped the bedsheets. Her landlord's full weight was on her, and he hooked his arm underneath her right arm and gripped his hand around her neck.

Choking her, he began slowly humping the trap's firm ass, savoring every sensation. The tightness of her O-ring, despite having been fucked just ten minutes beforehand. The heat of her body around his member. The slick pleasure of her skin against his. And the willing submission she offered.

Many of the real women he'd met didn't like sex as rough as he did.

Maybe he should be picking up femboy traps when looking for a hookup?

Vikki's stifled whimpering caught the man's attention, and he released her neck. Dazed and aroused, she turned her head to look behind her. Seeing a smile at the corner of her mouth, he repositioned them both so they were on their knees and then slammed his cock back where it belonged. Vikki moaned for a second before he pressed his hand down on her head and held it against the mattress. Giving her ass several harsh spanks, he began fucking her with hard thrusts.

She tightly closed her eyes, taking his sexual abuse and loving it. Her whimpering moans broke in pitch each time his thighs slapped into her rear and knocked some air out of her lungs.

"Fuck your sissy gurl, daddy!" she cried.

"Yeah, you fucking slut!" he gave her a sharp spank. "Take daddy's cock like the whore you are!"

He spanked her once more and then pulled on a fist-full of her hair until she was on all fours and her back sharply arched, revealing her lithe flexibility. As he forced the trap to face the ceiling, he leaned forward and bit into her neck. She gasped at the sharpness of the pain, but her arousal was too high for her to want it to stop. After he released her neck, leaving a dark love bite, he grabbed onto either side of her head and put his middle and ring fingers into her mouth and pulled her lips taught across her teeth.

She shook from his pounding, her chastity lock was repeatedly tapping against her plastic cage, and the bed's headboard was banging against the wall, but he showed no signs of stopping. The skirt of her maid's outfit quickly slid down her rear and interfered with his momentum, so he stuffed the hem inside her black garter belt. He then hooked his arms behind Vikki's, pulling them behind her back and her into an upright kneeling position, and wrapped his other hand around her neck, squeezing until her whimpers were muted into squeaks.

"Sluts like you like it rough." he whispered into her ear.

His thrusts were much more gentle than before, given his lack of leverage, but he was still firmly in control and that's how he liked it. Her hole instinctively tightened around his erection as it glided across her prostate every time his thighs pressed against her cheeks. Vikki's arousal increased as the minutes passed, and large drops of precum oozed from her cage. She could almost feel an actual orgasm of her own begin to rise up from her sissy spot.

And then her landlord decided he wanted to change positions.

Rolling her over, he lifted her legs over her shoulders and roughly thrusted back inside her. Leaning forward until her knees were pressed against her chest, he slapped her face a few times and then spit into her mouth. Expecting more, she parted her lips and stuck out her tongue, but instead of spitting, his own lust drove him to dive his tongue against hers and own her mouth. While their lips were locked in the throes of sexual lust, he began rocking his hips.

His humping began at a quick pace and when he broke their kiss to breath more heavily, he slapped Vikki's face once more. It was harder than the last few times, so her eyes watered, but her being treated like a worthless sissy cock slut somehow made her want his cum even more.

"Fuck your sissy gurl, daddy!" she begged, earning another slap to the face.

"Shut up, you worthless bitch!" he snapped.

Tears rolled out of the corners of her eyes toward the tops of her ears, and she clenched her hole harder to milk him of his fluids. The air conditioning in his apartment was limited to a wall-mounted appliance that only circulated air through his living room and kitchen, so his bedroom was already hot beforehand. Now, with their physical exertion, it felt like it was ninety degrees and beads of sweat formed on their skin. While filled with lust, being hot and humid only enhanced the experience for them.

Tightly gripping her throat once more, Vikki's landlord stared into her eyes and lustfully said, "Take this dick, you fucking slut..."

Her breath was strained, but not blocked, and her whimpers came out in soft squeaks. His hot breath blew across her drenched face as it became shallower, and his thrusts became quicker. The room had quietened down to a soft orchestra of heavy breathing, slick skin slapping against slick skin, and the creaks of the bedframe rocking back and forth.

As the man's orgasm approached, his rising, deep moan joined the music.

With a loud and shaky, guttural grunt, he exploded and pumped his seed deep inside Vikki's rear. After the third pulse, he aggressively locked lips with her and let his body jerk and shake until he was spent. Breaking the kiss, he began catching his breath.

"Was it good for you, daddy?" Vikki playfully asked.

With a smirk, her landlord pressed the palm of his hand over her mouth and replied, "A slut has better use for her mouth than talking."

She nodded and winked, and then he released her and rolled over onto his back, still catching his breath. Vikki got on her hands and knees and positioned herself to use her mouth as a slut should: sucking dick. She bobbed her head up and down until she had sucked all fluids from his member and then swallowed it all down.

A week later, Vikki had fully moved into Kristy's basement bedroom. Her femme wardrobe only partially filled the walk-in closet, but that left room for the male clothes that her Mistress had no intention of letting her wear while they lived together. Vikki was fine with that, considering her role as a sissy slave and, two days after her ruined orgasm with the electrodes attached to her penis while watching a new 'To be a sissy: Vikki' hypno involving feminization surgeries and hormones, she was on her knees and assisting Kristy with one of her regular clients.

He was an average twenty-something asian guy named Bill, black hair and naturally almost hairless, and a few inches taller than Vikki. He was hanging naked in the middle of the basement with his hands bound together and strung up to an eye bolt in the ceiling with his feet just barely touching the floor. Vikki knelt in front of him wearing her maid's outfit with his six-inch erection directly in her face while Kristy stood behind him with her flogger in hand.

Their Mistress was wearing her black, strapless latex dress with the mid-thigh skirt, latex four-inch heel, thigh-high boots, and her hair tied in the Mistress braid. Her makeup included black eyeshadow and bright red lipstick and her demeanor was seductively dominant and controlling.

Thwap!

Kristy's flogger struck the man's rear and she asked, "Is my pain slut horny?"

"Yes, Mistress." the man said.

Thwap!

"Do you want my little sissy slut to suck your cock?"

Bill looked down at the feminine cutie as she looked up at him. "Yes, Mistress."

Thwap!

"Too bad, slut." Thwap! "Your pleasure comes from the pain I inflict on you."

Kristy suddenly unleashed several strikes on his rear, crisscrossing left and right, always arcing downward and to the side. When she stopped, she gazed upon his skin as its color morphed into various shades of pink. Then she whipped each cheek once more, harsher than before. Kristy looked into his eyes in the mirror and saw his lustful desperation.

When she had met Bill, he was merely curious about femdom and now his sexual pleasure was inextricably connected to receiving pain from a domineering woman. Just for fun, Kristy once demanded that he get hard, even allowing him to masturbate while staring at her, and his erection wasn't very strong. Now, he was almost ready to explode without even being touched by anything other than her flogger.

And that was just a warm-up.

Kristy caressed his ass as she walked to the pegboard above her bench and traded the flogger with a crop. Returning to her slaves, she noticed a large drop of precum at the head of his member. "Vikki, I want you to make sure that none of his precum drips to the floor, but you may only use your lips on the bare-minimum of his cock to suck it off. No tongue and no fellatio."

"Yes, Mistress." Vikki replied, then leaned forward and put her lips to the very tip of the average-size mushroom-shaped head.

Bill groaned in frustration at having a pair of lips on his organ, but only for a moment and not being able to really enjoy it. Kristy praised her sissy for being a good gurl and took her position behind her male pain slut. She then caressed his skin with the folded leather at the end of her crop, giving him a sudden and unexpected strike here and there along his outer thighs.

Thwack!

She stepped to the side and moved to the backs of his thighs, starting closer to his knee joints. He wouldn't start to fully enjoy himself until she was much closer to his ass, but she wanted to build the anticipation.

Thwack!

"Has my pain slut masturbated in the last week?" Kristy asked.

Thwack!

"Yes, Mistress." he lustfully replied.

"And how was it?"

Thwack!

"Not very good without your whip, Mistress."

Kristy smiled to herself, knowing that she ruined any chance for him to have a painless, vanilla sex life. "Good."

Thwack!

Her aim rose to just above mid-thigh where his skin began turning a hint of pink. She alternated between each leg until she suddenly struck his right cheek much more harshly, causing him to submissively yell out. Vikki watched as his dick twitched hard and a large drop of clear fluidspilled out, forcing her to quickly bend down and catch it with her tongue before it hit the floor.

Kristy studied Bill's lustful expression and came to the conclusion that he could cum with just a few strokes of his manhood right at that point, proving that his pain training was coming along nicely. Within a month or two, Kristy would probably be able to make him cum from her infliction of pain alone. All because she made his sexual pleasure dependent on his receiving of pain.

Just like she was making Vikki's sexuality dependent on being feminized, focused on cock, and with complete neglect to her own penis. Kristy was changing the very nature in which the sissy viewed sex and her role in it. Eventually, Vikki wouldn't even imagine sex any other way.

Just like how Bill can't imagine sex without quenching his thirst for her whip.

She gave him a few more taps against his thighs before another harsh strike at his other cheek, but to Vikki's disappointment, there wasn't another drop of precum that time. Kristy struck bright pink skin in several places just barely harsh enough to earn a whimper from him over the next few minutes before she stopped.

"How's my little pain slut?" she asked.

"Very good, Mistress." he softly said as his body shook from his brain processing the pain as pleasure.

"Does he want some more?" she playfully asked.

"Yes, Mistress. Please..." he quietly begged.

Giving his balls a tap with her crop, she walked back to the bench and traded it for her three foot-long whip. It had five individual leather straps at the end and was Bill's favorite. Returning to her position behind him, she gently looped the whip around his neck and pulled.

"Is my pain slut ready for my whip?" she whispered behind him.

"Yes, Mistress!" he enthusiastically nodded.

Slowly pulling on the whip with her right hand, it slid around his neck until it was no longer trapped between it and his right shoulder. Kristy stepped back a few feet and readied herself. She made deliberate eyes contact with him in the mirror and then chose her target.