It was Friday night. Bennett walked into the main club room sipping his favorite single malt. Seeing Carolyn sitting by herself, her head buried in a newspaper, he walked to her.
“Good evening. I am Bennett Fitzgerald. I believe you are Carolyn Anderson.”
She looked up. Not recognizing him, she replied, “Yes I am. Are you new here? I do not believe we have been introduced, but your name is familiar for some reason.”
“You probably recognize it since I am on the Board of Directors of the club. I am the one that did your background investigation for membership and recommended you be approved. I probably know more about you than you know yourself.”
A bit flustered, she began to stand as she said, “Oh yes, of course. So pleased to finally meet you. I had hoped to, but you never seem to be in the club.”
“I am here often but usually go into the Director’s rooms for more privacy. Tonight I wanted to speak with you if you are not busy.”
“No, no not at all. Please sit.”
He had found her an interesting woman when she applied for membership; it was probably the most exclusive club in the city. After his team investigated her, he fully supported her membership. Now it was time to see if he made a correct assessment.
His research had shown that she was thirty five and married. The manager of all twenty six branch offices of the National Bank in the city. A type “A” woman, she hired and fired with no feeling except for the company. No allowances were made, you either worked to her standards or you were gone. She tolerated no mistakes or lazy work. It was all part of her plan to be in corporate management in the next few years.
Her marriage to a university professor had long ago become sexless and loveless. It was now just a convenience for both of them.
This convenience had left her sex drive lacking fulfillment. It was just as strong as her drive for recognition and promotion in the bank. Her type “A” behavior continued into her sex life. When she needed satisfaction she found a man, never the same one, and used him to satisfy her needs for a night.
Reading between the lines of the report on her, Bennett thought he detected a suppressed and probably smoldering submissive desire. He intended to bring it to the surface if it was indeed there. He had done the same in the past with other women and never been wrong yet.
“I thought it might be fun for us both if you came to my home for the evening so we could get to know each other better. That is if you have the time and the inclination.”
Her needs had been building. She thought this might be just what she required to satisfy her desires, while at the same time charming a Club Director and possibly advancing her circle of powerful friends. His dangling carrot was having its intended effect.
“I would love that Bennett.”
“Wonderful. My driver will meet us out front. Excuse me for a minute, please meet me by the front door.”
“Perfect. Meet you there.”
As she headed for the door he moved away and called his staff at the Tower to leave some instructions. He owned the top two floors of the sixty-five floor condo building referred to as the Tower.
Bennett was a billionaire. His money was known only to a small circle of friends and his businesses known to a much smaller circle. Everything he did or owned was through offshore companies, nothing was directly in his name.
After finishing the call he met her at the door just as Matthew was pulling up in the Bentley. He vaulted from the car to open the door for them. Bennett stood aside to let Carolyn in first, then followed her into the spacious back seat.
Surprised by the car and driver, Carolyn wondered why she did not know him. She prided herself on at least having some knowledge of every moneyed person in the city and made every effort to get to know them on some level. She had never heard of Bennett Fitzgerald but tried to cover herself when she told him his name was familiar.
The car’s windows were dark. She could barely see out and no one could see in. Having never actually been in a Bentley she was amazed by its luxury and total silence; no road or other noise penetrated.
Bennett, feeling that he knew her personality well, had decided a direct approach would be the best. As soon as they began moving he commenced explaining what he knew about life, specifically her sex life and his thoughts about a conscious or unconscious desire for submission.
Her mind was reeling from what he knew about her and what he was proposing, but having steeled herself over the years for unexpected encounters and questions, she remained outwardly calm as she tried to absorb it all. The dangling carrot was still in her mind and she realized that he might have a point about submission. She often wished she could just give up during sex and not feel like she always needed to be in charge of how events unfolded.
He concluded his thoughts and awaited her reply, staring deep into her eyes.
Having made her calculation, she said, “Well Bennett I have to say I fully expected there was a high probability that tonight would develop into a sexual encounter between us, but I had never considered your ideas regarding submission. Since you were direct and honest with me, I will return the favor. I have to admit the idea intrigues me. You may well have a valid point about unconscious desire so I am going to say yes to your idea and see where it takes us.”
“Good. Now unzip my pants and suck my cock.”
“Here? Now? I—“
Slap! Her right cheek stung from his blow.
“How dare you! I could—“
Slap! Her left cheek hurt as much as her right.
She recognized she was at a cross-roads. Did she submit or did she fight back? So many thoughts... The carrot, her sexual desires, what to do?
Bennett had not missed the initial smooth flow of her blouse over the enchanting domes of her breasts now topped with two prominent points. Her nipples were clearly swollen; she was obviously sexually aroused. His hands flew like a snake strike to her nipples, grabbing them and squeezing with stunning power. Carolyn’s eyes almost bulged out and her mouth opened in a silent scream. She was overwhelmed.
“I know you must be stunned. I have been told the pain is immense, but I have also been told that beneath it is a certain erotic sensation. Search for that feeling. Soon the pain will fade. Do you know why?”
She shook her head no.
“My grip has cut the blood supply to the nerves in your beautiful nipples and that limits their ability to transmit pain. So while I have your undivided attention I want to explain the rules we will follow. First, and foremost, you can say stop at any time and whatever is happening will stop. If you do say stop it will be the end of everything, not just what may be happening at the moment. Matthew will take you anywhere you wish. You and I will never speak again, about anything, anywhere.
“You must never say no or don’t or in any way interrupt what is happening. If you do it will either result in punishment or an interpretation of ‘stop’. You must totally accept your submission to me. Do you understand everything I just said?”
She nodded her head yes.
“Was I right? Has the pain diminished? Do you feel anything pleasurable?”
“Strangely yes. It is a good hurt. That makes no sense.”
“I suspect you will find that as the night wears on. Soon I am going to release you, but unfortunately that will cause you more pain than my current squeeze. The blood will rush back and your deprived nerves will be innervated causing them to send new, stronger pain signals to your brain. This will be a test of your submission and control. You must not make the smallest sound or punishment will result. Clear?”
“God yes! Just do it.”
He released her. Electrical signals shot to her brain. She scrunched her eyes, gritted her teeth and balled her hands into quivering fists... then emitted the smallest squeak. The pain passed. She relaxed back into the soft leather seat and began to breathe normally again.
“You know you made a sound.”
“Yes I know. I tried as hard as I could, but it just slipped out. I am very sorry.”
Somewhat surprised by her seemingly compliant acceptance of his actions he decided on a "punishment" that, in any event, was the next step in his plan.
“Your punishment is to remove all your clothing now. Your attempt at compliance was evident, and you will not be needing your clothes for a while anyway. Besides I want to see the lovely body that awaits the pleasures to come.”
She was almost in a daze from her bewilderment over everything that had happened so quickly. She had given up control so easily and was inexplicably finding pleasure. In moments she was naked, her clothes on the deep pile carpeted floor. Turning to Bennett looking for affirmation, approval--he did not disappoint.
“My dear you are exquisite. Your breasts are so perfectly formed and capped by luscious nipples. Are they okay now?”
“They feel perfect,” she said as she cupped her breasts and stretched them towards him.
“Spread your legs a bit more. Yes like that. A perfectly smooth pussy that I believe is already a bit damp?”
She ran a finger between her puffy labia. It came away covered in her juice, which she offered to him. He sucked her finger, licking off all her essence.
“Delicious my dear, absolutely delicious. We will have so much pleasure together!”
“I feel bewitched. I want you to take me, use me. I am burning for whatever awaits.”
Just then they pulled into his private underground parking next to his private elevator. From there it only stopped at floors sixty-four and sixty-five. He owned them both.
Matthew opened the door for Bennett. He exited and went to her side, opening the door and offering his hand. She held it as she emerged. He embraced her, feeling her body mold to his as they had their first kiss; it was deep and long lasting.
She felt no embarrassment from her nakedness, rather a bliss from feeling she was so appreciated. They were whisked to the top floor, his residence, where they were met by Maryann, his female factotum. Bennett made the appropriate introductions. Maryann led then to his study and inquired after drinks, she had Bennett’s usual Gibson waiting. Carolyn asked for water and a Cosmo, both were quickly produced.
Even in her heightened sexual state she had not forgotten the carrot. She attempted to gently draw Bennett into a discussion of his business but he deftly avoided her questions. He soon stood and took her hand, telling her it was time for more ravishment of her delectable body.
He brought her into another room that was dark, almost too dark to see. Escorting her to a couch, he handed her leather boots and wrist cuffs, instructing her to buckle them tightly to her feet and wrists.
“What’s going to happen?” she asked as she followed instructions.
“What fun would it be if there was no surprise. Just make them nice and tight. All will soon become clear. Rest assured your submission will result in your pleasure... eventually.”
Two ropes had been silently descending from above as she completed the task. He again had her stand and walk to where the ropes hung. He clipped one to each wrist cuff, then they began to pull her arms up.
“Oh Bennett you devil. I am going to be totally exposed and vulnerable. I am trembling with excitement and apprehension.”
“Just remember what I said about using ‘stop’. Anytime you wish it will end. Now spread your legs. That’s it. A little further. Perfect,” he said as he clipped her ankles to the floor and had her arms raised the final distance. Her legs were stretched wide and her arms pulled tight, totally vulnerable.
The lights came up just in the area where she was restrained. He walked up to her and they kissed as he playfully toyed with her nipples. Then he backed away and produced a riding crop.
“Do you know what this is Carolyn?”
“A riding crop I think?”
“Exactly. What a jockey whips a horse with to drive them faster.”
He gave her ass several strokes to demonstrate.
“OH fuck! Damn that stings.”
Then more strokes til both cheeks were red and she was shouting as each one landed. The pain was dazzling her. She wanted him to stop but did not want the consequences of using that word; she endured.
Back in front of her, he asked her if she thought it was possible for him to make her cum with the crop.
“I don’t see how,” she gasped out. “My ass is throbbing and on fire!”
“Well let’s see what it will do to your pussy, your clit in particular.”
“Oh fuck, you’re going to kill me!”
He started to very gently slap her clit with the small square tip of the crop. As her ass pain faded she realized what he was doing actually felt good. Her clit was responding. The pleasure signals were flowing. God she hoped he would keep that up. She knew she could cum from that.
He kept it up. Sometimes a bit harder, sometimes very soft, always carefully watching her to see how close she was getting. Now her pussy was dripping. He was getting her closer.
“Yes, yes! God that’s good. I’m so close, just a bit more.”
“You like that do you?”
“Fuck yes!”
“How about this?” he asked as he whipped across a nipple.
“OH! You fucker!” she shouted as she reflexively tried to twist away.
“That will come later,” he said calmly and went back to his gently tapping.
He repeatedly brought her up to the edge and down, time after time. She started out cursing him every time he brought her ever so close and then whipped her back. Then she started to beg, begging to be allowed the orgasm that she needed so badly and was always just out of reach. Finally she just went quiet. She had reached total submission, at least for this moment in time.
He recognized her state and knew it was time to push her over. So once again he gently brought her up to the edge. Expecting the inevitable, her eyes glazed over as she braced for the impending pain, but it did not happen. Her whole body began to tremble. The feelings she knew so well continued to build until suddenly she fell over the cliff.
“Oh my fuckin god! I’m cumming! Fuck, fuck, fuck!” Then she dissolved into the strongest, muscle racking orgasm she had ever experienced. She felt the fluid gushing from her pussy as the feeling ran through her body. As the sensations began to fade she collapsed. Her legs no longer holding her, she was hanging by her arms.
The ropes quickly lowered her to a waiting stool where Bennett and Maryann held her, gave her water and began to sponge her body with chilled, scented water to cool and soothe her. A heavily padded table was slowly moved in front of her as they continued their ministrations.
As she was renewed she said, ”Damn Bennett, you are a true Svengali. Never in my wildest dreams did I ever even imagine an orgasm like that. God I hope it is only the first of many that at least approach that intensity.”
“Believe me, it was a pleasure to give it to you. I hope to give you more, in different ways.”
“The ‘different ways’ part would be wonderful,” she said with a chuckle.
“Well I think it is time you get some cock. What do you think?”
“Oh that would be fabulous! I have been praying for a good fucking. My pussy is sore from your games, but it still wants cock!”
“Your wish is my command.”
“Only if it happens to coincide with your plans for me,” she quipped.
“Well this time it does. We are going to help you up so you can lie forward on the table in front of you. It is well padded and has a hole for your face, much like a massage table.”
They assisted her up and into position on the table, making sure her face was comfortably placed it the specially designed hole.
“How does that feel?”
“Fine. This is actually quite comfortable. Are my legs going to stay tied to the floor?”
“Yes. I want to make sure your intimate parts remain fully accessible, however your arms will remain free. I do have to put this strap across your head to keep you in place.”
As he was talking he secured a wide leather strap over her head to make sure she could not lift up. Between her ankles and head she was effectively pinned to the table. Bennett then retrieved an anal plug and began to insert it.
