Charles, Becky & Samantha

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A playboy, housecleaner, and lawyer explore power and sex.
4.3k words
4.21
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Part 1 of the 5 part series

Updated 04/05/2024
Created 03/28/2024
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Charles strode into his home office at 10:30am on a sunny Tuesday. He had just finished his morning workout and was feeling energized for what today would bring. He had given himself twenty minutes to interview a new housecleaner, followed by a session with Samantha at 11. He sat at his desk, took a breath to center himself, and pulled up Becky's resume. There was no particular reason why he chose to interview her over the other candidates, just a gut feeling.

Having retired at 40 from a successful tech startup, Charles was thoroughly enjoying the prime of his life. He owned an estate in the hills of Silicon Valley where he pursued his many passions. With an intense presence and voracious curiosity, Charles' main interest these days was people. He wanted to know what people held in the deepest recesses of their souls, beyond what they often even allowed themselves to know. He found great pleasure in creating situations where he invited people to reveal themselves. Once he discovered this game, he couldn't get enough of it.

He buzzed Becky into his office. As she walked in and took a seat across from his desk, Charles quickly sized her up:

Fit body. Shy smile - she's nervous. Conservatively dressed - she's not trying to be eye candy which means she'll do a good job of cleaning, no wedding ring, ah - pearl earrings! She's a good girl.

By the time she sat in the chair, Charles had already decided he wanted to hire her and his plans were clicking into place. Besides having her clean, he wanted to see how much she would be willing to let her wild woman loose.

"You arrived early and followed the instructions to get into the property. I like that." Charles flashed his most expansive smile.

"Oh yes," Becky assured him, "I'm always on time and very good at following instructions." She tucked her curly brown hair behind her ears and then smoothed her palms over the tops of her thighs. She was sitting up very straight.

Becky needed this job. She was putting herself through nursing school by doing house cleaning jobs, but somehow her current load had dwindled. She knew it was the night shifts at school that were making it harder for her to focus on work during the day. If she didn't land this job, she was going to have to take out another loan in order to pay rent at the end of the month. She shuddered.

Whatever it takes, get this job.

Besides, this house was huge and this guy was clearly insanely rich. It felt like the answer to her prayers.

I just hope he's not an asshole. Rich men are usually assholes.

But Charles seemed nice enough. He asked questions quickly and barely waited for her answer before asking another one. She felt like she couldn't get a hold of the conversation, but Charles was beaming a warm presence at her which helped her relax a little. She decided he looked like a light-weight boxer - he was clean cut, muscular without being bulky, and moved quickly.

As long as he's smiling, I'm doing great. Becky thought.

"Now Becky," Charles' tone shifted as he slowed down, "I'm going to make you an offer here and I want you to really consider it before you say yes." Becky was automatically nodding her head. "I'm going to pay you double your normal rate." He paused to observe Becky hold her breath and widen her eyes. "And I ask for three things in return." Another pause.

I may be dramatic, but this sure is fun. Charles gave a simple smile.

"First, I ask for total honesty. I'm welcoming you into my home and paying you generously for your work. I have zero tolerance for lying, sneaking, or stealing."

Becky's head nodded more vigorously at this statement.

"Second, you may see other people coming and going from his house. Do not, under any circumstances speak to or engage with anyone except for me."

"Third, do you see that red door along the back wall of the living room?" Becky's gaze followed his pointing finger. "That room is off limits. I want you to clean the whole house, but never enter that room. Understood?"

Becky's mind began to race. That's it? Don't steal, don't talk, and don't go in that room? And he's going to pay me double? Easy!

Becky confidently lifted her chin, "I understand how personal it is to have someone come clean your home. I will absolutely agree to those three requests. You can count on me."

"I had a good sense about you from the beginning Becky. Don't let me down." Charles' brain was already shifting gears to his next appointment with Samantha. "Here is the contract. Sign here... Can you start today? Wonderful." And with that Charles strode efficiently out of the room, leaving Becky to integrate her good news.

===

Charles is the most dangerous man I know. Samantha mused as she changed out of her business suit and into a black lace lingerie. He has power and money and prestige, but what makes him dangerous is that he doesn't care about any of those things. He's not using me for sex either - it's disorienting. And this is exactly why Samantha was paying Charles a ludicrous fee for a session in his dungeon every week. She savored the pulse in her pussy at the thought of danger.

One month ago, seemingly out of the blue at the end of a business meeting, Charles leveled her with his dead-serious intensity and stated, "I know what you want."

A small laugh escaped her lips, as Charles had caught her off guard with the comment. And then her body coiled like a cobra ready to strike. "Charles, do not waste my time with your bullshit."

"I'm not bullshitting you. I'm offering you a gift: I know what you want." Charles was unphased.

New tactic: "Ok then," devilish smile, "please, tell me what you think I want." She flipped her blonde hair to the side, and recrossed her legs slowly and deliberately.

"Every meeting you're in, you're the most powerful person in the room. I hired you as my lawyer because you pin arrogant tech bros to the wall and make them bleed. You are gorgeous and merciless. A natural killer." It wasn't flattery or seduction. Charles was simply speaking the truth. "But you don't want power. You already have it."

Men are so predictable. Now he's going to tell me what I really want is his cock. And then I'll pretend to soften and next thing you know, I'll have him by the throat and I'll be $20 million dollars richer.

"You don't want to be powerless either." Unflinching intensity. "You are disgusted by how people give their power away."

That's not what she was expecting. Suddenly Samantha could feel the fear gather at the back of her throat. She held her composure as she realized she had misread his intentions and now had no idea what Charles was doing.

Same tactic: "Ok Charles, if you're so smart, why don't you fill me in?" She leaned back, subtly allowing her breasts to perk up. Years ago, she had mastered the art of showing off her body without seeming like she was trying to.

"Containment. You want containment."

Samantha blinked twice. Her mind went blank and then she took a massive breath of air as if she had just dropped a 50 pound weight off her chest. She suddenly felt naked and held back tears from the corners of her eyes.

Charles tilted his head slightly and softened his gaze, as if to convey, I'm not going to hurt you. Then:

"What you actually want is just to feel your own power, in your own body, in a space that is safe enough to hold you."

The truth of these words was visceral for Samantha. Her pussy was wet, her chest was trembling, and the tears had started to flow. It was the most vulnerable "Fuck you." she had ever whispered.

Charles leaned back in his chair and took a few breaths to observe Samantha. What an incredible woman. Then he brought his attention into his own body: pure, calm, aliveness. This is what I live for: speaking truth fearlessly and the intimacy that it unlocks.

Samantha could feel her inner little girl mixing into her voice as she asked, "Ok, so now what?"

Charles took a big sigh. "You're still worried that I'm making a power play over you." Pause. "I'm realizing I need to put this in terms your lawyer-brain can understand. You're going to hire me to provide the containment you're craving. We're going to do 2-hour sessions, one day a week. You write up whatever contract you want for this agreement."

Samantha began to feel solid ground once more, together with a swirl of emotions that had been very tightly locked away: loneliness, fear of abandonment, arousal. She took a big breath to compose herself as she wiped the mascara from her eyelids.

"Oh and," Charles continued, "You're going to pay me five times the hourly rate you charge your clients for these sessions. It's the only way you'll actually value what we're doing."

She felt anger flash across her face as her pussy throbbed even harder. Slowly, she admitted to herself that he was right. She wanted containment. She hadn't even known she wanted containment, but once he named it, the desire was undeniable. She needed structure for the sessions and she needed it to be a financial hit to pay for. As she calculated how much it would cost, she immediately realized that it would be worth every penny.

That was one month ago. Now, Samantha is wearing 8" black stripper boots and lingerie into Charles' dungeon for their fourth session. She carried an envelope full of crisp $100 bills.

This money is my permission slip to get to be furious, she thought as she stomped in. Charles was sitting in his regular clothes on a black bondage bench in the center of the room. Before he had a chance to stand up, Samantha hurled the envelope of cash at him, hitting his shoulder and splashing bills across the room. Charles didn't react.

Samantha gave herself permission to pick an ugly fight.

"You're awful at this. You just sit there doing nothing. Now I know exactly why your ex-wife divorced you."

"I see you're feeling safe enough to throw a tantrum."

"This isn't a tantrum!" She stomped her boot, oblivious to the irony, "You're literally the worst--"

"Stop dispersing your anger and feel it." His voice was clear and strong, without a hint of taking this attack personally.

Samantha widened her stance. Her fingers curled into claws at her sides and her face snarled as she began to roar.

"That's still not it." Charles was intense without being overpowering. "I said, feel it."

Samantha closed her eyes and clenched her jaw. All of the energy in her body started to flow inward. It felt like a tidal wave of anger rushing into her chest, when suddenly it hit a stone wall and bounced back out. Involuntarily, Samantha's jaw popped open and tears sprang out.

"There you go!"

Samantha found his enthusiasm extremely annoying as she tried to clamp back down. Not tears, anger she willed.

"Nope!" Charles was reading her body language, "Let it come!"

Samantha opened her eyes and allowed a strangled sob to leak out. As Charles held her gaze, a wave of grief washed across his face. What the fuck? Why is he crying now too? At that, the dam in her chest broke open and the tears started to flow. Big snotty sobs gushed out from the back of her heart. She took two awkward steps toward Charles.

Taking the cue, Charles deftly guided her body to lie down on a mat on the floor and spooned her from behind. He drew her body against his and wrapped her firmly with his arms. At this, Samantha really let go into the tears. Her whole body shuddered. She wailed.

As the first wave of tears crested and then subsided, Samantha began to feel arousal as her body responded to Charles' behind her. Then her womb opened and another strong wave of tears began. This time the grief was undulating up through her spine. Charles continued to hold Samantha while flowing with her body.

"Give it a sound." He instructed.

Samantha led out a low moan that grew in pitch and intensity until it became a scream. Her body shuddered.

"Take a deep breath." She inhaled through spasming lungs. "Now, make another sound."

This time it sounded like a baby wailing. The sound emerged from the core of her womb and Samantha had the distinct sense that this pain was carried over from her ancestors.

"Now take five slow, deep, breaths."

Samantha's body relaxed and the tears mellowed. Her hips were still undulating, full of energy.

Charles slid his body apart from hers and guided her to lie on her back. He placed his right hand very firmly on the center of her chest.

Ahh, grounding, she thought as she felt her body melt. She found it vulnerable to look into his eyes, but his attention was focused on her body. Her hips were still rolling forward and back.

Charles lifted his left hand very deliberately, and then slowly moved it down to cup her pussy. Once his full palm met her lips, he let his body weight lean into her heart and pussy.

Oh my God - yes! Samantha thought as her whole system surrendered into being held. She wanted him inside her, she realized. She wanted to feel his cock pressing deeply into her cervix. Wanted to squeeze her pussy around him and hold him tightly.

Samantha had never in her adult life allowed herself to genuinely want this level of intimacy. She had learned early that by controlling sex she held power and that her vulnerability led to being dominated.

"This is completely different" She said in awe.

Charles nodded. "Now make a sound for what you're feeling."

Samantha closed her eyes and let her jaw relax open. From the back of her throat an "AAAA" began to emerge.

"Deeper," Charles instructed, "From here." he said as he pulsed his hand against her pussy.

Samantha made a "Hhhaaa" breath out. Followed by another one, and another, and another in quick succession. She realized she was about to have an orgasm.

"That's it!" Charles encouraged.

Samantha closed her eyes, tilted her head back, arched her spine, and let go into an orgasm that was unlike any she had ever experienced. She panted. Her voice raised as if in song - it didn't even sound like her voice any more. She lifted her head as something was rising from her pussy and moving out through her throat. She felt Charles's hands support the undulation of her body. The intensity continued to rise. She realized that she could not stop this even if she wanted to. She tossed her head back again and let out a primal scream. Her legs were wrapped around Charles' torso and holding him in a death grip. At the end of the scream, everything relaxed and her consciousness splashed into the void.

Sometime later, Samantha awoke from a very deep sleep. She was on her back, still wearing her fuck-you black heels. Charles was resting at her side. She could feel their two bodies breathing together.

===

Becky was congratulating herself on her new job, her newfound income, and on the excellent work she was doing cleaning the house. Charles isn't even going to recognize this place it's so clean now. She felt more energized than she had in a month.

She carried her vacuum and bucket full of cleaning supplies into the living room. Start at the top and work down to the carpet. She pulled out the duster and began to hit the window sills. Suddenly, Becky's ear picked up a sound. It was a muffled sob. Becky froze and listened. There. Someone is crying back there. She looked to the source of the sound. Well of course it would be coming from behind the forbidden red door, she thought. Becky took a few steps closer and tilted her head to listen. A woman is definitely crying back there. I wonder if she's ok.

Becky could feel the bind she had just stepped into. I can't go through the door. I can't talk to anyone else. I don't know where Charles is. For all I know, he's torturing that woman. Becky was lost in thought for a moment. Or maybe her cat died. I really have no idea. Becky decided she would have to stay busy cleaning the living room to listen to the sounds. If it got any worse, she would call 911. And after all, she was training to be a nurse. She could definitely help if someone was injured.

The crying continued as Becky listened intently. She decided they were not sobs of pain, but sobs of sadness. Maybe they're going through a breakup. That idea actually seemed like it made a lot of sense and helped Becky relax again.

Eventually the crying gave way to a moan. This moan was different. Becky felt it in her pussy. Now what's happening? Becky dared to sneak up and press her ear against the door. As long as they're doing whatever they're doing, they're not going to barge out this door. Oh yeah - that woman is turned on now.

The moaning came again, this time louder. Becky felt her nipples getting hard. When was the last time I had sex? Heck, when was the last time I self-pleasured? Working her way through grad school had taken a toll on Becky's sex life. Feeling a little naughty, Becky leaned her ear against the door. Oh, it's getting good now! Becky squeezed her thighs together. She tried to imagine the positions of the bodies and the face of the woman.

The panting and yelling continued to get louder. Without realizing it, Becky's hand had made its way down into her panties. She was wet. Becky bit her lip hard. Then the big crescendo began inside the secret room. Becky held her hand steady and rocked her pussy into it. What kind of crazy orgasm is this woman having? I've never heard anything like this!

As the woman climaxed, something clicked for Becky. I need to get myself off - now. She looked around. Suddenly she realized how exposed she was. She was standing in the middle of the living room, touching herself, where anyone could walk in from three different directions. Bathroom! Becky thought.

===

As Samantha slowly walked from the dungeon to the bathroom, she took stock of her present state. This had been her biggest session with Charles, by far. She had moved a lot of energy. Her legs felt a little woozy. A massive weight had cleared from her heart and womb. Her pussy was still very turned on. And she really needed to pee.

Samantha absent-mindedly opened the bathroom door and strode in. Suddenly, she jolted to full poise - her viper instincts sharp as ever. Sitting on the toilet in front of her, Becky had two fingers in her pussy with her other hand squeezing her nipple. She had put the top seat down on the toilet so she wouldn't accidentally fall in. There was not even a plausible chance that Becky was peeing in here.

Shit! I left the door unlocked!

Becky's jaw dropped open as she took in Samantha: Blonde disheveled hair, mascara all over her face, lean yoga body with small perky breasts, black lace lingerie, and shiny black heels.

This was the woman!

As a child, Samantha had been a competitive fencer. One thing she had learned was: let your opponent make the first move and then respond. These instincts now kicked into gear as Samantha leveled a withering gaze at Becky.

After a speechless moment, Becky stammered, "I was in here just--"

"I can see what you were doing."

Another pause. Now Samantha ran her eyes over Becky: pretty, young, inexpensive clothing. She's probably the maid or something. Samantha could taste Becky's shame and fear. She took a powerful step forward with her fuck-you boot.

"Please--" said Becky.

"Please what?" The initial shock had subsided for Samantha and she was now fully in control here.

"Please...um...you can't tell anyone that I was in here"

Samantha took another step toward Becky. "Why not?"

Becky's eyes got even wider. Her spine started to curl into a cower. "Because...I'm...I can't..." Becky was starting to collapse.

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