The Rich Man's Married Whore

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Housewife gets indecent proposal, finds a Sugar Daddy.
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SlyDog969
SlyDog969
569 Followers

It wasn't what she would call an unhappy marriage but it certainly wasn't one that blew her skirt up either. Cassandra had dated her husband back in high school and got married right after her graduation. Her husband was the only man she had ever been with.

For ten years she played the good housewife game that she had been raised to believe in, she was always told that if she was a good girl and a faithful wife she would find true happiness. So where the hell was the happiness they promised she was now wondering?

They lived a meager uninspired existence going from paycheck to paycheck never able to go anywhere or do anything. They had talked about having children a couple of times but he kept saying they couldn't afford it, which was fine with her because she knew that with him she would only have ugly babies that cried and complained all the time just like him. Every morning as she sat across the breakfast table from him she would look at him and ask herself, "is this really the man I want to grow old with?"

Then one night at a business party where her husband was trying to impress some rich clients she meet an older man some 30 years her senior. His name was Mr. Jameson, a very distinguished looking gentleman that apparently came from old money and was very influential in local and state politics and moved in social circles that she never even knew existed.

He paid her lots of compliments and lots of special attention and after a few drinks it was clear he was hitting on her. Cassandra was not use to being in that situation; she was both scared and excited.

A few days later her husband told her that the gentleman was extremely wealthy and that a contract with him could be the answer to all their financial problems in fact they could be set for life. He told her that the older man had indicated he would sign a contract with her husband's company if she would sleep with him.

She was appalled that her husband would even repeat such an offer to her. As the days went on her husband kept bring the idea back up sometimes casually and eventually being more and more direct sometimes almost in a forceful manner telling her that their entire future and financial wellbeing was tied to her having sex with this client.

She could not believe that her own husband was trying to pimp her out. At first she was outraged and refused to even talk about it making it clear that it was his problem not hers, and why should she degrade herself for his stupidity and incompetence. He showed her the credit card bills and the second mortgage all long overdue and in both their names.

She stressed over it for three days and nights and driving herself to both physical and emotional exhaustion. Then on the morning of the fourth day she was wondering around her tiny modest little house holding an empty coffee cup in her hand, surveying her pitiful excuse for a life, she finally said "I don't care. I don't give a shit anymore. It can't be any worse than the life I'm living now." "Fuck it I'll do it" she said. She called her husband at work and told him to set it up.

On the night she was to meet the gentleman whom she had now nick named him Mr. Money Bags, she was dressed up in her best outfit which wasn't saying much, her hair, nails etc. had been made up just for the occasion. She felt like a tramp and was trying to look the part even though she wasn't sure if she was going to able to go through with this surreal nightmare that she was being forced to participate in.

Her husband dropped her off at the hotel bar where Mr. Money Bags had rented a room. Cassandra was mad and humiliated that her husband had just dropped her off, just left her there to have sex with another man. Like dropping off a baby at the orphanage or dropping off used cloths at Salivation Army. Was that all she was to him?

She walked timidly into the lobby of the very expensive hotel. Even though they had only met once she immediately recognized Jameson sitting in a large chair in the lobby.

When their eyes meet she smiled timidly at him. He rose walked over to greet her with a reassuring smile trying to put her at ease. He took her hand and thanked her for coming and commented on how lovely and attractive she looked.

After a few seconds he gestured towards the elevator with a warm smile and she followed. He waited to make sure they were the only two in the elevator and push the button for the penthouse. Cassandra stood there looking straight ahead at the elevator doors while he stood silently behind her until the doors opened on the twenty-ninth floor.

Cassandra was more than ready to escape the confines of the elevator, she felt her nerves stretching thin, and she certainly did not want to lose her courage or composure now.

He retrieved the key card in his pocket, put it in the slot, and unlocked the door to their suite, their evening retreat. He held the door open to the sumptuous suite offering it up for Cassandra's preview and approval.

"Wow! This room is like a small apartment." she exclaimed. It was something Cassandra had only seen in movies. The suite had a living room, with a dining area and separate bedroom. There was even a small bathroom, a powder room off the foyer. Everything was spotless and completely indulgent in its opulence.

"Do you approve?" he asked as he closed the door behind them.

"I can't believe this place. It's magnificent." Her eyes gazed out into the main room and beyond to the city out the large paned windows. The sun was lowering in the sky and it gave off a reddish orange glow. She could feel the warmth on her face as well as within her body.

"To be honest I originally booked a full view of the fountain, a junior suite they call it. But last week they sent me an e-mail saying they had a cancellation for this suite and offered me a free upgrade with my frequent flyer points." He put out his hand and stroked her arm. "I think you deserve to have a nicer room to feel more relaxed and at home in."

"Thank you. I love it." She advanced further into the room then looked back over her shoulder at the distinguished looking gentleman whom she was feeling much more comfortable with now and even somewhat attracted to.

She was glad now that she had downed those two mixed drinks before leaving the house. She was now beginning to redraw the image in her mind that she had created previously of a lecherous dirty old man. She decided maybe she should give this guy a mental makeover if nothing else to help her survive the night which so far was not looking all that bad.

He was gentlemanly, well-mannered and had a subtle confidence that only an experienced older man can extrude. He had all the trappings of power, the expensive well-tailored Italian suit, very expensive shoes and a gold Rolex that grabbed her eye the moment she meet him. With his distinguished looking well-trimmed gray hair he looked like a father figure she could surrender her underappreciated treasures to and now for some unknown reason she was starting to feel more than a little bit horny around.

It had been a long time since any man had made any effort to impress her and never had any man made her feel this special. She was now getting intrigued wondering where this evening was going.

Maybe the idea of having a sugar daddy was starting to grow on her. Maybe she just liked the idea of how she could use this night to throw it back in husband's face and make him pay for putting her into this situation and pay for the shitty life he had provided for her. The more she thought about it, the more she liked the idea of hurting him. She could definitely justify in her own mind having sex with another man for that.

She leaned back as she looked into the bedroom and saw the huge kind-sized bed adorned with numerous pillows. She observed the mature gentleman carefully waiting for him to make the first move. She had promised her-self to go slow and she didn't want to unnerve herself now.

Standing together he touched the smooth skin between her neck and her shoulder and moved down until it rested on the top of her breast. Without hesitation, he slid his fingers under the material of her blouse and continued moving down until he reached her nipple. When his hand cupped her breast, Cassandra's eyes closed. It had been a long time since a man had taken his time with her and she had long forgotten what that felt like.

He offered to let her set on the bed if she wanted to get more comfortable. As she did, Cassandra undid a couple of buttons on her blouse, flashing a little cleavage. Jameson feasted on her young, tender breasts, feeling his cock twitch in his pants. He rubbed his cock ever so slightly trying not to be too obvious.

He visually consumed her lovely silhouette not unlike he was a savoring a well-aged single malt. His eyes kept scanning her body enjoying how perfectly her blouse hugged her breasts just tightly enough to make him want to release them from their cruel entrapment and gently caress them with his hands, softly kissing them with his lips while lightly sucking on them to give her the long denied pleasure that no beautiful women like this should ever have to endure.

He could now see how her skirt had ascended higher up her thigh, exposing her black satin panties concealing her youthful flower that he so desperately wanted to know and devour. His self-control was losing the battle to his desires as the unmistakable bulge in his suit pants was now pressing outward to make its intentions known.

Cassandra noticed this, and opened her legs a little more, flashing her now damp-looking panties.

He lowered his hand, and stroked her leg, just stopping short of the edge of her pussy. Cassandra softly moaned to communicate her approval.

Cassandra slowly undid a couple more buttons on her blouse, letting her breasts show, not caring that he was old enough to be her grandfather. She fixed her eyes on his bugling cock in his pants. She dared to reach out and rub it through his pants.

Jameson let out a soft moan, and then gently slipped his hands inside her open blouse.

He fondled and squeezed her breasts with firm hands, twisting and pinching her hardening nipples not too roughly but just the way she needed them to be touched.

Cassandra unzipped his pants, and began to tease his now throbbing, very stiff cock. She pulled it out of his boxers. It wasn't the biggest cock she'd ever seen, or the widest. In fact, it was skinny and long - very long. Cassandra thought it must have been a good 9 or 10 inches in length. His cock was in her hand now as Cassandra stroked it, and she was getting hornier feeling the touch of the slippery wet manhood she held with a tight and commanding grip.

The head of his cock was already glistening with pre-cum looking so tasty she just couldn't resist. With only the slightest hesitation so as not to look too eager, Cassandra opened her mouth and began flicking her tongue over the head, tasting his bitter pre-cum. It felt so dirty and so deliciously naughty she could not believe it.

She quickly decided to take him all the way in her mouth. Inch by inch she moved down his shaft, feeling it fill her mouth. Cassandra wanted to gag, but kept going. She'd never taken a cock this long before by deep throat. She had now mentally discarded the whole good girl pretense and was now fully vested in sucking that cock like she had never sucked before.

Cassandra finally had him deeply in her throat and bobbed her head up and down his length ever so slowly, moaning as she did so. She had her hand inside her panties now, rubbing and twisting her clit, trying to make herself wet.

She noticed his man shaft throb and twitch, and then she felt him begin to spasm uncontrollably and then forcefully squirting his cum into her sweet mouth, his man seed gliding down her throat.

He lightly caressed the side of her head as his squirting subsided and allowed her do the honors of removing it from her mouth which she did very slowly looking up at him very appreciatively like and angle who had just fallen from heaven.

Cassandra stood up to face him, unbuttoning his shirt; He too began to unbutton her blouse and tossed it to the floor while she slipped her panties off.

Next he gently slipped her bra off and her luscious breast so that they could hang freely. He took one into his mouth and bit, sucked, and licked it. She tasted so damn good to his eager tongue. He went from breast to breast, sucking, biting, and licking each one with a determination to make them stand at attention. Her nipples were now like small mountain peaks, protruding outwards proudly revealing her youth and excitement at the attention he was giving them.

She was as naked as the day she was born now, standing there in front of him wearing only her wedding ring and a sexy smile. Jameson stood back to admire this beauty. His cock was standing at full attention like a dutiful soldier as the national anthem was playing.

Cassandra boosted herself up onto the king size bed, and spread her legs open wide, giving him an unobstructed view of that sweet, wet, young cunt leaving no doubt that she was now willingly offering herself to him.

Cassandra kept her eyes firmly on his and rubbed her pussy. She gave him a seductive smile as she inserted one finger, and then another and another, until her whole hand was inside her well shaved pussy.

Jameson could hear the squelching sound her pussy was making. She removed her fingers one by one and offered them to his open, mouth. He sucked them in, licking off her sweet juice.

She reached for his hand, and pulled him close, thrusting his hand onto her snatch. She was dripping!

Without missing a beat, he dropped to his knees. Her cunt looked too inviting not to eat, and with one hand, he pulled at the opening folds of skin, before diving in with all he had. His teeth and tongue were all attacking her clit simultaneously in a relentless barrage of licking and sucking.

Soon she began gushing uncontrollably! He smiled with his mouth open ready to receive the gift of this beautiful woman's love juices. She covered his face and tongue in an erotic shower of her nectar which he quickly devoured and savored it like it was a magic elixir sent down by the Gods.

Rising from eating her, he smiled a dirty old man smile.

He could see Cassandra was still wet, and still needing to be fucked. He looked down as the engorged helmet pressed against her swollen pussy lips. He rubbed and poked at her, as his balls were filling with cum. He slipped into her easily, and pushed his entire cock into her warmth.

She was terrified at first from the anticipation of his penetration however once it was done it was incredibly liberating once that boundary had been breached it was like a bird be set free released from captivity and allowed to soar up to heights never before experienced.

Cassandra raised her legs in the air, opening them wide for him as he held himself up on his arms above her.

He gave her a powerful thrust. "Ohh!" she cried, pleasure shooting up her spine as his slender cock rammed deep inside her. He began to fuck her with abandon. He jackhammered in and out of her while her feet were flailing above his thrusting ass.

The bed was squeaking a little under the intense force of his thrusts. Her tits were bouncing up and down to the rhythm; she was biting her lip to reduce the volume of her moans.

His cock plunged in and out of her; he slid his penis out of her vagina with an audible 'slurp'. He rolled her over on top of him, holding Cassandra on his penis. She began bouncing up and down in a matching rhythm with his upward thrusts, keeping time with his cock which was slipping in and out of that young pussy with such ease. His shaft was shining from her wetness. The constant penetration in and out of her love box was making her cry out in ecstasy.

He leaned forward pulling her head towards him darting his tongue roughly into her mouth, he kissed her. Cassandra offered no resistance and soon she was exploring his mouth with her own tongue.

Her heart was racing into oblivion as beads of sweat were forming on her forehead.

"He sure doesn't fuck like an old man" she silently mused to herself.

He didn't give her the chance to cum, at least not yet.

Suddenly he flipped her over on her stomach with her feet on the floor bent over the edge of the bed. He ran his hand over her cute little ass, and with his other, he rubbed his cock over her ass. It made Cassandra nervous, but it also excited her.

Jameson finger fucked her pussy, one finger at a time, slipping up inside her. One by one, his fingers went. Her pussy was still very slippery with his juices and hers. Jameson held Cassandra by the hips as he pushed his cock into her. She was tight! He loved feeling how tight she felt wrapped around his manhood. The second Jameson's cock began to enter her; Cassandra bit her lip, holding in her urge to whimper out loud.

He pushed himself further and further into her, until he was completely inside, his balls touching her ass cheeks. He held himself there for a moment, before he began to fuck her, slowly at first, then harder and faster he nailed her to the bed. His other hand jumped between pussy and breasts, first attacking her breasts, then her pussy. This young slut was going to be his.

In and out he pumped and banged away at her. She marveled at how well a man with such a skinny, but long cock could fuck and use it so well and bring such a delightful range of pleasure to so many different parts of her body.

He gave her no quarter; Jameson fucked away at her young cunt with the power of a wild animal, relentless in his attack on her pussy obsessed with planting his seed inside her.

Cassandra held herself in place, down on all four her with her legs slightly spread apart, her ass was in the air filled with his shaft still offering it to him while she was looking straight ahead across the room lost in a trance consumed by the myriad of sensations now overwhelming her body.

His cock twitched and his demons urged him to fill her, soon his cum was splattering the walls deep inside her making her pant and scream, and writher like a wounded animal gasping for its last breath.

Jameson soon filled her with his cum as he let out a muffled grown of pleasure. A long, thick stream of white fluid shot out the end of his rod and splattered across her taut round ass, some of spewed it all the way up to the lower part of her back.

Cassandra was panting, her chest heaving as she felt more of his cum fire out in a thick stream. It felt so hot on her skin, and it turned her on knowing that it was not cum from her husband, but from someone else.

Cassandra soon felt herself building up to climax. She shook a little, as the tremors of it began taking hold. She couldn't hold back and then in a sudden rush she let herself cum.

Finally, the last of his semen trickled out of him, dripping onto her.

They remained frozen in that position like two marble statues for more than a minute as their spasms subsided and they regained their lost composure.

As his decompressing penis gently slipped out of her and into the cool air conditioned breeze circulating around the room they eventually rolled over to catch their breath for a moment. With no need for verbal communication they both acknowledged that they were done for the evening.

Cassandra rolled over on her back looking up at the ceiling.

As she lay next to him, legs spread wide. Her eyes were closed, she was smiling.

"I needed that." she whispered, as he reached forward and kissed her smiling lips softly.

Cassandra wondered how he had so much energy and how he could have done all that mind blowing sex without having a heart attack at his age.

"Where the hell do you rich guys learn how to fuck like that?" she asked.

SlyDog969
SlyDog969
569 Followers