Jerome Halleck was a powerful captain of industry, with some 34 companies in his comglomerate of petroleum interests. He even owned some natural gas companies, and was looking ahead, investing in alternative fuels, so that his family would be ready for the change of fuels when oil ran out. He was 76 years old and 4 times divorced, with a track record of womanizing a mile long.
Since he had warned the women in advance that he would sleep around, he did not much like their jealous reactions to his promiscuous lifestyle. Thanks to pre-nups, the hypocrisy of at least 2 of his ex-wives (they were also sleeping around), and his excellent lawyer/paramour Jane Kiesinger, Halleck had kept most of his wealth intact. Halleck had to use a pill these days to keep up with the girls, but he considered it worth his while to maintain his libido.
He tended to marry not very young "trophy" wives, but middle-aged women, who would be more likely to find him somewhat sexy, especially due to his experience in bed. He liked the MILFs, because they were known to be fertile, and he liked to be an "alpha male", still siring children in his 70s. His latest wife was named Corinne, she was a good 40 years old, with children by an earlier marriage, and a professed willingness to share and share alike, which was one of his reasons for taking her. She was also honest enough not to feign love- she was looking for a "sugar daddy", and he fit the bill.
Halleck had concerns, however, that she would feel unsatisfied with a husband of his age and inclinations, despite the potency pills he took, so he thought that he should perhaps ensure that she was happy in his absence. This made him think of the perfect solution- a male escort, on call, to service his wife whenever she was needing more than Halleck could give her.
An escort was great for him, because: a, he would not be taking it personally- it was just a job; b, he would insist on a condom, reducing the danger of child born to his wife by another man before she gave Halleck one; c, he would be available whenever his wife needed it badly, so she could always count on sex; and d, Halleck paid for the services, so he ultimately controlled them.
Halleck sat Corinne down the same night that he decided on this, telling her, "Honey, you know that I am a swinger, and I appreciate your acceptance of that fact, as well as your overall lack of hypocrisy about this marriage. I want you to be happy, since you have done so much for me. I think that, if I get to sleep around, so should you, so I thought that the best solution would be to hire an escort to please you, whenever you need more sex than I can give you. How does that sound?"
Corinne was in virtual shock! She was prepared to accept the status quo, because she liked what Halleck did for her, both in bed, and in her checkbook, but this was wonderful! He cared about whether or not she was satisfied, and apparently because she was so reasonable and helpful a wife, especially compared to her predecessors. This was typical Halleck- fair, honest, and clever, not to mention generous. Her septuagenerian hubby was a great lover, who always ate her pussy at night, whether the pills worked or not. In return, she had made a point of sucking him off, if even she failed (which was rare) to get him erect.
"Yes, honey, I'm very pleased and grateful- I don't know what to say! You're the sweetest sugar daddy in the world, and I will do my best to prove my gratitude, particularly tonight! I would love an escort, since we would have our professions in common- I know that I'm a whore, and I don't mind it. Very well, I take it that you will continue to try for another child? I want to give you one, you know. I understand that gigolo use condoms, so they are a better choice. Thank you so much, Daddy (her pet name for Halleck)!"
So the couple began arranging to hire a gigolo, and soon found him: Uncas Savoy, a tall, biracial man in his 30s. He had muscles of considerable size, and a fairly large manhood, to say the least.
Savoy was a little nervous, only because this was a big boost to his company's business, and he was worried about blowing it for his employers. He was determined, however, to prove himself, and on the 1st night of his new assignment, he was all ready for his "date", as the arrangement was technically termed (to pretend it wasn't prostitution).
Corinne was waiting for him, having given her hubby a "good luck, see ya later" kiss as he went out to fuck Jane. She knew that the lawyer was just a casual partner, because Halleck would never marry a person who could represent herself in a divorce case.
"Hey, Mrs. Halleck- it's me, Uncas Savoy. I am your escort tonight.", Uncas announced.
She did not say a thing, but rather seized him, gestured for him to strip, and then started sucking him off, while he reached for the rubbers. Getting one out, he reminded her that he had to use it, so she grabbed it from him, and put it on his cock herself, showing an eagerness to begin screwing him that he had not imagined from a 40 year old woman. I guess it's true about their peak, he thought. He'd seen it before, but only once or twice, because most of his clients were men.
She sat on his cock rapidly, thrusting it in and out of her pussy, as she began to react to its size. Halleck's was 7 inches, but Uncas had a 9 incher, really impressing her. He was planning to go into porn, as soon as he could make the money to move to California.
She was kissing him while he penetrated her, despite the evident lack of sentiment. She was in heat, not love, and that was better for him, because janes that fell for their gigoloes were often trouble, he'd been told. He grabbed her buttocks while they fucked, working them with his hands, and making her even hornier. She was definitely an aggressive lover, possibly even a dom, and her libido was clearly more than her old man's, he assumed. That must be why I was hired, he thought.
Uncas then moved her over onto her back, getting her wetter still, with the thought of getting pounded so roughly. She liked it hard, and he was going to oblige her, as her hubby was paying him well. He rammed her pussy harder still, shoving his penis into her vagina with all of his power, and getting her ready for climax. She came with a superhuman scream, and he had to pull out immediately, so he could remove the rubber and shoot off on her ass, which she really loved. She even smeared her fingers with it, and licked it off them.
"Anything else, ma'am?"
"Yes, can you eat me?"
"That's $50 extra."
"I'll put that on your hubby's tab. He won't mind it, I'm sure."
"Exactly- he loves to have me pleasured that way."
She was soon reeling from the effects of his cunnilingual skills, as he began to ravenously dive into her sex, eating her clam for all of its wonderful taste and smell, and making her weak for sure. She was clearly craving an all-nighter, so he began planning to negotiate a price in his head, even as the rest of him concentrated on getting her off.
His mouth even moved toward her asshole, teasing her with the possibility of anilingus. She was non-verbally begging him for it, so he gave a hand signal that it would cost another 50 bucks, and she mouthed to him that it was OK- Halleck would understand.
His mouth closed in on her butt, spreading the cheeks, and then began rimming the crack, licking the outside of the rectum, and running his tongue along the sides of it. She was being slowly, methodically reamed out, and she was dying from the pleasure. It was awesome! One thing's for sure, she thought- there was not going to be any jealousy now, with her needs so completely covered by Uncas Savoy and Jerome Halleck. They could have as many lovers as they wished- she just wanted to get fucked by both of them.
Corinne finally signalled a last act of the session, before she would bargain over the next- she wanted her ass fucked like crazy! He read her mind, from the way she looked down at her own ass and his cock, and he said, "$100 for anal, and once again, we require protection."
She nodded her consent, and he prepared to get the lube, when she shook her head, pointing to the condoms, and gesturing for him to use her the hard way again, which he silently agreed to do for her. He eased his manhood into her bottom, and then steadily moved up the pace, getting her so wet that she could barely stand it.
As he kept ruthlessly slamming her pucker, she increased her moans and groans, along with some whimpering, because it did hurt. She was obviously fine with that, more than so, in fact, because she now came at last, shrieking her climax to high heaven. So ended the 1st session, and already she was thinking about the 2nd, which she wanted later that night. Thanks to her husband, she was the happiest whore in the world.
As for Halleck, he was greeted as usual by Jane, who kissed him with fervor and desire, as she really did enjoy their liaisons. In fact, she was falling in love with the old man, despite herself, because they had been screwing each other for 20 years by now. It had acted as a surrogate for a long-term relationship for both of them at times, and now for Jane, it was becoming such a relationship to her. She had never resented his other women, especially his wives, particularly since they tended to come and go, while she was still in his life.
Jane did not want marriage from Halleck- just his love. She also wanted him to help out her niece, Rita, who had just broken up with her loser boyfriend Dick, a heroin addict. Dick did nothing for Rita at the time right before the break-up, and she finally had to give up on the slacker, who wouldn't even fuck her anymore. His need for heroin had suppressed even his sex drive, he lost his last job due to sheer absenteeism, and he even stole money from Rita to support his habit. That was the point where she decided to dump his sorry ass.
Jane knew that her niece, a paralegal, would need cash, plus some action, after that draining relationship and its dissolution, so she schemed to get Halleck to pay Rita for sex. Both would get laid, Halleck might have another child, which he really wanted, and Rita would have enough money to pay for the costs she incurred during her relationship with Dick. She already told her niece of her plan, and the girl really went along with it, since not only was Halleck rich, but, according to Aunt Jane, he was great in the sack and reasonably well-endowed.
So, when Jerome, which was what Jane called Halleck by now, had gotten inside, he saw his lover's niece present there, and naturally wondered why.
"I see that Rita is here. You know that I like her, but I thought that this was a date night."
"It is, sweetie- a triple date! She is coming along, not as a chaperone, because who'd want that, but as a sex partner for us- both of us!"
"Excuse me? You're suggesting a threesome? That's fantastic- I always knew that you weren't the jealous type, but this would be the first time that you indicated any interest in a 3-way encounter."
"Jerome, darling, Rita really needs a man to fuck her, since she has not been laid since she was with Dick. She also needs money, so I thought that we should pay her to fuck us- how does that sound? We could divide it, with you paying 2/3 of the cost, since you'll be fucking her more often. I will cover the rest- what do you say- $300 for a session tonight, with more sessions every week?"
"Fine with me- I take it that she wants this?"
"Naturally, my love. I think that I should tell you that too- I am in love with you, Jerry."
"Really? How long has this been the case?"
"For a while, now, I suspect. We have been shagging each other for some 20 years, so it's hardly surprising that I would love you by now. Plus, I've been working for you that long."
"Yeah, it has been 20 years- wow! I was 56 then, and you were 27, just a young, ambitious lawyer with plenty of spunk, and I chose you because of your inventive idea for the defense in my 2nd divorce case-the notion of tacit understanding of extramarital pleasure. I liked that, hired you, and it worked."
"You also started fucking me during the case, remember? Hell, I wanted it as much as you, even then, and we have not stopped sleeping together ever since! I know everything about you, Jerome Halleck, and I love the old, skirt-chasing, greedy curmudgeon that is you."
"Thank you, dear. That means a lot to me, because you have not just been working for my money, and I really feel close to you."
"Good, and I hope that you get closer to my niece as well. You probably won't live to fuck her for 20 years, but she can benefit from your skills and wealth while you live."
"So, Aunt Jane, am I going to be hired, or not? Does Uncle Jerome want me?"
"Yeah, she likes to call you that, and I encourage her, because you do seem rather avuncular to her. Remember that you've known her almost all of her life."
"Yes, she used to sit on my lap."
"She can again, Uncle Jerome!"
At that, Rita planted herself down on Halleck's thighs, wrapping her arms around his neck, and kissing his entire face. He started kissing her back, locking lips with the 24 year old paralegal. She was the youngest woman he had fucked in a long time, and she definitely had the energy to prove it, but it was well worth it to please Jane and her adorable niece.
"What about me?", Jane half-seriously asked, as she began pulling Jerome's shoes and socks, and then sucking his toes. She moved with incredible ease up his legs, kissing and licking his calves, and then unbuckling his belt, to remove his trousers, so she and Rita could suck his cock and balls. Rita got off him, helping Jane take off his boxers, and slowly began licking his cock, followed by Jane, and they started sharing it for a bit.
"Oh, Aunt Jane, Uncle Jerome's cock is marvelous! I love it, and I really love that he's paying me to have this kind of fun!", Rita exclaimed.
"I'm paying you, too, so remember to pleasure me when it's my turn!"
"Yes, Aunt Jane, I will do that! I can't believe that I accepted Dick's ultimatum to break up with you the last time we were sex partners, since I could have found a way to achieve a menage a trois if I had really tried, and Dick was no substitute for my darling aunt!"
"Thank you, baby, but let's get back to work- we have a cock to suck!"
"Would you have let me fuck Uncle Jerome if I had chosen you?"
"Well, of course, honey! I've really hoped to get the three of us together for some time now, and I'm glad that you accepted my proposition this time. Now, baby, let's keep sucking our boss!"
"I really am her boss now, as well as yours, aren't I?"
"Naturally, since you're paying most of her expenses."
The girls resumed their fellatory task, getting Jerome quite stiff indeed, as their tongues bathed his penis repeatedly and sometimes in combination. The feeling of 2 women's mouths on his manhood was exquisite. He could not take it much longer, as the ladies kept up their efforts to suck him off.
Soon, after a few grunts, he told them, quite excitedly, that he was going to come, and they just sucked him even harder to push him over the edge. His phallus spat up a tsunami of cum, spreading it all over their tongues and lips. They licked it up, gargling it in their mouths, and then exchanging it in a wonderfully passionate incestuous kiss. They looked at each other, licked their lips again, and then giggled at what they had accomplished.
Jerome's cock was still hard, despite the gushing his geyser had done, and it was getting harder still. His 7 inch boner almost seemed to command them to bend over and offer him their cunts. They complied, he looked down at the lovely girls begging for doggie-style sex, and he had to give it to them- there was no doubt of that fact.
First, however, he began orally pleasuring the girls in turns, going back and forth from Jane to Rita, with the lady who didn't have his tongue inside her pussy getting his fingers instead. This constant transfer of stimuli from one cunt to the other was getting the women all hot and bothered, and they began sweating and cursing, which soon led to screaming, as their climaxes took over their bodies. Jane's long, slim shape was well-balanced by the tanned, curvaceous form of Rita. They both dropped continual beads of perspiration from every pore of their voluptuous bodies.
When their oral satisfaction had been accomplished, Jerome eased into Rita, wanting to give her the first lay she ever had with him. She bucked back delightfully against his cock, using her hips to draw more of his length into her pussy. He slowly but steadily accelerated the momentum of his cock inside her cunt, and her aunt felt the impact as well, because Jerome was still finger-fucking her at the same pace that he pleasured Rita.
It was almost a contest between his cock and his right hand, with no certain winner, as Halleck drove Rita to the limits of her possible ecstasy. Jane was every bit as excited, and the girls began to reach orgasm together yet again.
Halleck's was soon after theirs, and his cock released his sperm into Rita's vagina to the background noise of orgasmic shouts.
"OOOOOOh shit! I have never been fucked like that before!", Rita shrieked.
Jane laughed, "Neither have I, and I have enjoyed his wonderful prowess for 20 years! I have got to have it next- oh my God, it could kill me, but I'll take the chance, old man!"
Halleck granted her wish, quickly switching cock with fingers, putting the former inside Jane, and the latter into her niece's vagina. He began to recover easily enough, and his penis was filling up Jane's sex, while his hands were moving in and out of Rita. Soon, he commenced fist-fucking her cunt, and she started squealing her intense enthusiasm for that mode of penetration. Meanwhile, her aunt was taking Jerome's dick for everything she could, and he was giving it to her eagerly.
He was soon slamming Jane's cunt with full force, and she was reeling from the sheer happiness it was giving her. Her brain felt like it would explode, as the dirty old man pounded her at an increasingly dynamic pace. Not spared this relentless rutting was her niece, who was appearing to be on the verge of a spasm, due to the magnificent feelings his fist was stirring in her cunt.
Jerome now came through total stimulation, and his cum made Jane climax, followed immediately by Rita. He did not give them a chance to recover, however, before he slid his still-rigid manhood into Jane's posterior, taking advantage of her delectable mood to use her the way that he knew she could not decline or oppose. Every time he had fucked her ass, she had absolutely succumbed to the combined emotions of pleasure and pain, and she had cum uncontrollably.
The penetration of her derriere made Jane lose all self-restraint, as she just let him wear her out. She urged him to fuck her even more furiously, and he obliged, knowing full well that she was now at his mercy. The ramrod plunged deeper and deeper into her bowels, and she began shaking as the drilling of her backside reached its apex.
"Oh, Jerome- you've gotta finish me now, or I'm going to faint from the butt-fucking you're giving to me!"
He had mercy on her at last, and shot off his load, filling her bum, and making her climax yet again that night. All of this time, his fingers were in Rita's rectum, and she was getting it every bit as severely in the stern as her aunt, so that she collapsed at about the same time as her. They were all wiped out, and all Jerome could do was lean over toward his pants, pull out his checkbook, and write one to Rita for $200.
The girls rested for a few moments, and then Jane indicated that Rita still had to earn her pay from her aunt. She moved over to Rita, pulling her on top of herself, and began devouring the young lady's pussy and tush. Rita was going insane with the delicious anilingual experience, not to mention the cunnilingus, and she happily reciprocated, leaning over to eat Jane out.
Jerome just watched at this point, since his cock was too sore to use for now. He saw Jane 69 Rita, and they were deliriously happy, as he could tell. Evidently, Rita loved her aunt a lot more than most nieces did, and her story about having been lovers in the past was clearly true. What was more, Jane felt the same way about her niece, and this did not preclude her passionate love for Jerome. The 2 of them really were bisexual, and he revelled in the sight of their lips touching each other's labia, with their tongues manipulating the clitoris of each other's genitalia.
The women lovingly dined on each other's sex, for what seemed like ages, also rimming each other occasionally, and making each other all sweaty again, until at last the couple came into both mouths at once. They looked up, as each swallowed the other's juices, and saw Jerome masturbating at the view in front of them.
Jane could not resist the urge to move up to his cock, grab it, and stroke it for all it was worth. Rita at that point had to help her aunt, as the sight of her hand and Jerome's on his rod were too much to ignore. They kept this up until he finally came from the concerted work of his partners and himself. They took his jizz in their hands, and licked it off, cleaning them completely, before Jane suddenly pulled her gold coins together worth a cool hundred out of her secret jacket pocket, and slipped them inside Rita's cunt, to her niece's absolute surprise and delight.
"That was some way to pay me, Aunt Jane- it was more fun that way!"
"Good, because that's how I'll pay you from now on!"
The 3 of them spent the night together at Jane's, after Jerome phoned his wife to leave her a voicemail about his intentions. He had to tell her that way, because she was in the middle of her 2nd session with Uncas Savoy.
The man was practically tearing her apart with his macho member, fucking her so hard that she was crying, but she did not ask him to stop- in fact, she begged him to continue.
"Fuck my pussy harder, please! I don't care how much I cry, or how much it hurts- I need more of it!"
"Whatever you say, ma'am! I'm working for your hubby, and he hired me to meet your needs, whatever those are!"
He ruthlessly pushed and pulled into and out of her vagina, his condom-covered cock now soaking from the extravagant amout of natural lube she had released, which was protecting her from further agony. His dick was now plunging into her pussy with ease, and she was meeting him halfway with greater urgency and enthusiasm.
"Fuck me, fuck me roughly, fuck me as forcefully as you can!"
Corinne was now quaking from the hurricane that probed her pussy with gusto, and she was holding onto her climax for dear life, not wanting to release it just yet. She was determined to let him ride her as long as he possibly could. He groaned, she moaned, and they grunted together, as his penis thrust into her womanhood with every inch and all of its power, and then drenched the inside of the rubber with its satisfaction, which forced her to cum at last.
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