The Rich Man's Married Whore

He laughed "Oh they teach us lots of tricks at those fancy boarding schools, you have no idea."

As the euphoria of the sex wore off Cassandra was a little unsure of what she should do next.

"Well I should probably go now. We are all good now. Right?" she inquired.

He smiled, "We are more than good I want to thank you for an incredible evening."

"In fact I don't want to cheapen what we had here tonight in any way but I want to make you an offer since you were so incredible tonight" he said.

"Please understand I don't want come across as crass but I am by nature a very straight forward person, I say what I mean and I would never try to deceive someone as beautiful as you but if there is even the slightest chance you might be interested I want to put it out on the table."

She looked both puzzled and confused, "What exactly are we talking about?" she asked.

"I would like to have sex with again maybe even on an ongoing basis if you're willing, and not just that, I want to make you my companion to help me entertain guest if you feel comfortable doing so. In return I will make it worth your while financially. I can be very generous under the right conditions."

She was completely taken aback and caught off guard, she had not expected this. It was surreal, right out that movie indecent proposal. The initial shock left her speechless but as the shock of it his words slowly dissipated she began to gather her thought and try and put the night and his proposal into some type of context.

A thousand thoughts burst in and out of her head almost all of them telling her what a good girl should do, all the criticisms she had ever received and the punishments she had ever endured for even the smallest infractions or deviations from the rules now flashed across her brain and of course the sin she was committing was right at the top of her list.

Most women would have immediately said no but the one thing she had learned was that being like most women had not worked for her very well in the past and maybe it was time she needed to make a change in her life and reinvent herself or at the very least to explore her options.

She had always made only good choice all her life and she wasn't happy. This was the one bad choice she made being here tonight and it was the first time she felt that she was in control of her own life as strange as that may sound. Even though it was a vulgar and sexist offer it was also a second chance at a new life that she knew she may never get again.

It was one of those life changing moments where you just make a spur of the moment decision and she did exactly that.

"Yes" she said, "Yes I will do it."

She wasn't sure where this road would lead her but she knew that she craved more than she had back with her pitiful loser of a husband.

Beyond that, the idea of being a kept woman, a rich man's escort, or companion as he so graciously defined it, it strangely excited her and trilled her. She thought she had loved her husband all those years but suddenly realized she needed more and that he was a jerk and she was going have to leave some day anyway so why to hell not do it now?

"Exactly how will this work" she asked.

"Meet me for lunch tomorrow and we will work out the details in a way that you feel comfortable with." he replied.

She did meet him the following day for lunch at a very expensive restaurant. She wasn't sure if she could go through with it but anyway there she was. She had not informed her husband about the meeting, she wanted to see if she could really do it, and besides it was her decision not his.

"Just think of it as a job like any other job with certain duties you need to perform as part of your employment. Anyway that you want to justify it making it more acceptable for yourself and others is fine with me." he explained.

"If you want to think of it like a personal assistant with benefits, like an office affair with your boss where you don't have to go into the office, a secret life, a secondary husband whatever works for you."

It was an incredible strange concept for her to wrap her head around.

"What about the contract with my husband's company?" she asked.

"I have meeting this afternoon to sign the first contract with them. If this situation works out there will be more to follow."

It was all so business like, she kept waiting for him to give her some type of contract, or document to sign, but he never did. He seemed willing to take her word for it and did not try to pressure her in any way.

"Fine what do you want me to do first?" she asked.

"Just be available for when I need you and be ready to go where I need you to go. I will send a car for you."

He then handed her a half dozen credit cards and told her to buy some nice outfits for when he took her out and to never wear the same outfit twice. She immediately went out and bought a number of very expensive dresses and enough shoes to fill her closet she even gave herself an expensive spa day to get ready for her so called on call dates. She thought Mr. Money Bags would be furious when the bill came but he never said anything, in fact he encouraged her telling what outfits he liked to go out and buy more like that.

That evening her husband came home late after spending a couple hours at the bar celebrating the big contract that "he" brought in. She smiled, sat him down, and then informed him who actually brought in that contract and what her arrangement was to keep that contract and to ensure more like it in the future.

He sat silently looking out the window not sure what to say or how to respond. She didn't waste her breath scolding him or belittling him she just looked at him first with contempt and then with pity wondering what the hell she ever saw in him. She suddenly realized he was just a pencil dick little troll that liked to criticize and control her to compensate and hide his own inadequacies as a man. From now on he was going to be the window dressing to her life and not the other way around.

At that moment she got a text from Mr. Money Bags "Go out and buy some expensive cloths we're going to an exclusive dinner party tomorrow tonight, a black tie event. The limo will pick you up at 8." Cassandra started getting dressed to go out for a hard day of shopping and thought to herself, "Maybe this is the real fairy tale I was meant for!"

That following evening was the first of many parties and high class social events she would be required to attend. She very quickly realized that she liked to dress in nice cloths and when he took her out in public to expensive places even though she was committing adultery she liked being shown off and treated like a trophy by a strong and successful man. He had surrounded himself with many valuable things like expensive cars, half dozen homes, and now her. Maybe she wasn't his wife and never would be, but she liked the status she had when she was with him, something she could never have with her loser husband.

When he had sex with her he made it obvious he was just using her for sex, but for whatever reason that was exactly what she needed. It was actually a lot more satisfying than the sex she had with her husband.

With no emotional strings attached to sex it was in fact more liberating for her in so many ways. She liked living from orgasm to orgasm with a closet full of nice cloths and a purse full of credit cards she didn't have to pay off.

At first she would take her wedding ring off, at some point she asked him "Do you want me to wear my wedding ring on or not?" and surprising he said "Leave it on, I like knowing you are a married women."

On certain occasions he would call her to attend a formal dinner party and she obediently submitted to his wishes. Soon it became a common thing for her to be loaned out as a party favor for his friends, and strangely she actually enjoyed it and even began to look forward to it.

Initially in the beginning she felt cheap and degraded but that slowly changed and over time and she grew to embrace it. The idea of being wanted and desired as a woman by a number of powerful and important men that could have anything they wanted, she suddenly felt empowered and self-confident and self-assured in ways she had never felt before.

When she was younger unlike most adolescent girls who dreamed of a Knight in shining armor caring her off on his white steed to some utopian life she preferred the scenario of being ravaged by an invading hoard, taken back as a trophy to be used as a breeding whore for their animalist rituals and pleasures. Maybe subconsciously she was finally getting to live out some variation of that perverted fantasy that had once filled her dreams.

With each new man she slept with it was a constant surprise like opening presents on her birthday, some presents she liked and really enjoyed, and some that were just okay but it was always something different. If she didn't like one man she knew there would always be another, a different one tomorrow, and she wasn't trapped with the same man for the rest of her life anymore. When she was in between men, she would enjoy some alone time and not be saddled with housework or taking care of some ungrateful louse of a husband.

When Cassandra did go home it was simply a place to retreat to, to rest and wait for the next phone call and sexual date. Her husband, their house, her so called home was nothing more than a rest stop on the road to debauchery and infidelity that had become her new way of life. Her relationship with her husband was no longer about love but rather more just feeling sorry for the poor bastard she only had sex with him on rare occasions and soon she found it so unfulfilling she just stopped completely and he never bothered to complain.

Mr. Money Bags took her on numerous long trips to places like Vegas and Cancun which she found exciting having never been out the mid-west before. Then he took down to Rio for an entire week. They went to some nightclubs and expensive restaurants where she saw older wealthy gentlemen with much younger very sexy women who she later learned were high priced escorts. They intrigued her and she spent time watching their every move and she even took the opportunity to talk to a couple of them in the ladies room.

Mr. Money Bags held a number of parties at his place where she was expected to entertain the guest. She had no illusions the Mr. Money Bags was pimping her out, but then again that was exactly what her husband had done and what put her in this situation in the first place. She knew she should feel like a victim here but she really did not. All she knew was that it was a hell of lot better life than she had before and that she felt much more appreciated than at any other time in her life.

It was a few months later at one of those parties when one of the very rich foreign clients came up to her and after some small talked asked if there was place where they could be alone. She knew what he wanted and she was fine with it, after all that was what she was essentially there for. Cassandra took him to one of the back bedrooms well removed from the main part of the house where they could have sex.

Afterwards when they were done and he left, she stayed there for few minutes waiting so it would not be too blatantly obvious they had been together since the man was there with his wife. She was lying on the bed wearing only a black garter belt and dark stocking enjoying the cool air on her naked body when a young man wondered into the room, the son of one of the big name clients. She wasn't sure if he was lost or if he had come there seeking her out on purpose.

The young man who was only in his first year of college looked thin and fit and had sandy blonde hair. The surprise and chagrin look on his face was even more comical than hers. He observed her lying sprawled across the giant bed still covered in the sex from another man and began unbuttoning his shirt.

Cassandra wasn't sure what to say or do, on the other hand she liked the looks of this young puppy and as he eagerly pulled off his shirt and started undoing his belt she was genuinely captivated with him and lost in the anticipation of how he would look naked on top of her enthusiastically pounding his young cock deep inside her.

She willing pounced on the opportunity of corrupting this young boy and giving him a special kind of fucking that only an experienced woman with just the right number of years and sexual experience can provide. She relished the idea of her using someone else for sex for a change.

She knew young boys are never any good at foreplay and since he already had a very respectable hard-on she spread her legs and invited him to plant himself inside her already well used pussy. Clearly he didn't care about anything else but fucking her. Cassandra didn't think twice about it either, at least he was focused on her and not something else and he was young and eager to please. She had fucked a lot of men for their pleasure now she was going to fuck one strictly for her own sexual needs.

Fucking one man right after another she felt so cheap, so dirty, so naughty, and yet so powerful and validated as a women. She had given up control of so many things in her life and yet she now felt more powerful and in control than ever before, certainly more than she had ever felt being a dutiful wife to her loser husband.

As the handsome young stallion started to cum inside her she could tell he was unsure as to if he should pull out or not. "Don't pull out baby cum inside me. I want you're cum inside me as much as you do." she gently moaned in a soft reassuring voice.

He relaxed back down on top of her and thrust himself in even deeper as she wrapped her legs around his torso and pulled him all the way in until the head of his exploding young penis was blasting right up against her cervix.

She could see in his eyes that he was somewhat overwhelmed and excited, and appreciative over what had just happened. His face was so young and so innocent it brought out her motherly instincts and she just wanted to hug and comfort him like a lost little boy who needed to be loved, but then her own body overrode those feelings when own orgasm and after spasms made her return back to the here and now.

As her own convulsions subside she smiled to herself in the dimly lit room with the young boy of a man still lying on top of her, both exhausted and just enjoying the moment. She knew that none of the younger girls he had ever been with would have fucked him like she just did.

She was now his Mrs. Robinson, an erotic memory he would be embellishing well into his later manhood years, that dirty little secret he would carry with him and make him smile at the most inopportune times for years to come. She was the women he would now compare all other women to for the rest of his.

She felt smug and more than a little delighted with herself, there were numerous milestones in her slippery decent into this life of debauchery, and this was one of the more memorable ones that she could fully embrace and enjoy. She knew she should feel guilty about it, but she didn't.

A few weeks later she was working another social event when Mr. Money Bags brought her over and introduced her to a new out of town client.

Thomas was a tall extremely handsome black man with a British accent originally from the Islands who had studied at Oxford and done a short tour of duty with British Royal Marines before returning home to take over his family's business which was apparently doing extremely well. She estimated his age to be about 35. He was tall about six three to Cassandra's five six and his skin was a dark brown like an expensive dark chocolate that you savior and enjoy only on special occasions. He had a slender but muscular, build, he wore his hair short, and his brown eyes were large and sparkled and he had a certain charm she had not experienced even with all the sophisticated men she had entertained previously.

Every time this man spoke she would fixate on the movement of his lips and Cassandra would immediately begin to zone out. She felt a strange thrill and an indescribable kind of desire pulsating through her slowly at first then increasing in intensity the more she tried to fight it. She tried desperately to get those thoughts to leave her brain, but they wouldn't be denied and they were now consuming her every thought.

Between her legs she had noticed a strong sensation of arousal that was taking over her body. She looked straight ahead, but she could sense that his eyes were watching her and she wondered if felt the same animal attraction that she did.

Even though he was wearing an expensive suit she could just imagine him as some magnificent Mandingo warrior dressed in loin cloth holding a long spear ready to take her as the spoils of war to be violated and used for his pleasure.

In her imagination she knew he had an unbelievable penis, because she could see the bulge it made in his pants. Her thoughts strayed to a fantasy of how incredible it would be to breed with him, how she would take him in her pussy and in her ass, and fuck him like he had never been fucked before, her body moving on his huge cock until it filled her with tidal waves of his forbidden seed that would transform her body and her soul forever.

Eventually Mr. Money Bags excused himself and wondered off to greet some newly arrived guests leaving Cassandra to entertain Thomas by herself. They made small talk for a few minutes and went through a couple of drinks enjoying each other's company. At some point Thomas moved close to her and he gently squeezed her hands. "You know I think you are quite a beautiful woman." Cassandra couldn't believe it; this absolute god, this vision of black manhood was hitting on her. While he spoke Cassandra looked up into his soulful dark eyes.

"Would you be upset if I kissed you?" he asked. She didn't respond but smiled approvingly at him. He leaned in towards her and gently kissed her. She didn't move, his kiss was quite passionate and it had her heartbeat racing. He lifted his head again, placed his hands on her waist, and began to kiss her and slide his tongue in her mouth. They were the most passion-filled kisses She have ever had known.

They were both becoming aroused and Thomas started to hike up her skirt. His hands were all over her ass, he even rubbed between the cleft and briefly touched her asshole. At that point she indicated that maybe she should show him some other parts of the house, especially the back bedrooms. He nodded his approval and they proceeded down the hall where she knew they would not be disturbed and she could give him her full attention.

As soon as they got to the bedroom and secured the door they began kissing, their hands were roaming all over each other's body; it was not long before her hands were freeing his suit pants and briefs allowing them to fall to the floor while his hands found their way directly to her breasts.

"I love your tits," he said as he lifted off her blouse to reveal her black lace bra. Thomas just buried his black face in the pale freckled cleavage, kissing and nibbling. His hands grabbed at the straps of her bra and peeled them down her arms to reveal her large milky-white bosoms. His face greedily pressed against her breast and began to lick, kiss, and suck her nipples.

She did nothing to try and hide her excitement. At this point she literally had wetness running from her pussy all the way down her thigh. With most men she would have been self-conscience about her loss of control of her body but at that moment she savored it and wanted him to see just how hot and horny he had made her and how much she wanted him.

He leaned into her caressing the side of her neck and whispered into her ear, "I know what you need!" he said with that incredible sexy British accent with just a hint of the islands in his low deep manly voice.