Jenny’s husband had died two years earlier in car crash. It was a catastrophic event for the 34 year old widow in every possible way. She was a stay-at-home mom with 3 young kids. Luckily her husband had a decent life insurance policy but in two years the money was already gone. There was a substantial mortgage, car payment, the credit cards were maxed and worse yet, there was little or no equity in the house. There was no income other than the meager Social security survivor benefits.
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Jenny had gone back to work but with needing people to watch the kids it was almost not worth it. She called the mortgage company to see if they could help her in any way and they set her up with a meeting with her account manager. Jenny thought she needed to put her best foot forward and dressed her thin 5’4” frame in a business-like pants suit. She wanted to detract attention from shapely figure and present the appearance of the serious and level-headed mother that she was.
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She met with Bill who seemed to be genuinely concerned about her situation. Bill was in his mid-40’s and was not bad looking at all. Bill could only offer the suggestion that she downsize, but with little equity in her home and no cash available for a down payment of a smaller home, there were few options.
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Bill suggested that they meet for an evening dinner in a few days to discuss options that may be available. He said he needed a few days to check out these options. She was wary, but agreed. As they parted, Bill gave her a big hug and kissed her cheek. Jenny was afraid of what was going to happen with the meeting. She began to realize that there was little doubt that Bill had the ulterior motive of getting her into bed.
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She knew this was her only chance of keeping herself and her family from poverty, and her only hope was to please Bill. In order to do this she knew the best approach was to block out any negative thoughts and think positive thoughts. In trying to think positively, she thought about the fact that he was an attractive guy, that she hadn't had sex in ages, so why not? She thought that maybe she could fantasize that he invited her on a date with for no other reason other than potential romance.
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When the night came she decided to dress sporty, but not necessarily provocatively. When Bill saw her, his eyes lit up and complimented her on her outfit and said when they met the other day he did not realize how attractive and beautiful she was. Bill had her with that; Jenny was about to melt with the compliments as he was going on about how attractive she was. It had been a long time since anyone told her that, and she let him know just how much she appreciated that.
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After dinner at a ritzy hotel complex, with very vague references to alternate solutions to her problem, he suggests they go to the room he had reserved where they could discuss it further. She knew now that there was absolutely no doubt what was to come. She had been hoping for a miracle. Now she must settle for this, far from a miracle, but the closest she will ever get to one. Yet at the same time, she was really starting to like Bill.
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And liking Bill was easy enough to do, as Bill acted like a true gentleman even though they both knew they were going to be naked in bed very soon. When they got in the room Bill asked her to relax and freshen up if she needed to. She went into the bathroom, shut the door and wondered what the best approach to please Bill might be. Should she leave the bathroom in just her bra and panties? Would that be far too bold, or would that excite him?
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Jenny decided to play it cool and came out fully dressed. Bill became less of a gentleman at that point and just took Jenny in his arms and they began kissing. At that point any pretense of a normal first date was gone, and clothes began flying off and soon they both in their underwear lying on the bed. Suddenly Bill just stood up and looked at her with a smile. Bill told her what a beautiful sight she was and asked her to get up and do a slow strip for him.
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Bill' request seemed more like an order. Jenny was taken aback, and suddenly the passion and romance she was beginning to feel left in an instant. She pushed that negativity aside realizing she had only slept with one man in her life, and had no idea what other guys liked or expected. She was very uncomfortable doing the strip while being ogled. She would have had no problem stripping off her bra and panties in the heat of passion and rolling around on the bed with Bill, but this was so different. Other that her husband no man had ever seen her naked; and to be exposing herself to another man for the first time, this felt like a very cold and emotionless way for it to happen.
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But knowing what was at stake, she quickly complied with a smile. While Bill now lay in bed, she began to do a slow and sensual strip by unfastening her bra while dancing slowly, and finally tossing the bra on the bed but keeping one arm across her tits. When she saw the look on Bill’s face and how much he enjoyed watching her, that cold feeling was quickly replaced with warmth throughout her body. As she dropped her arm exposing her tits, she saw Bill’s eyes light up and she felt a rush of empowerment like she had never felt before.
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When she slowly peeled off her panties, she was so glad that she had trimmed her thick bush the night before just like she used to. Bill’s cock was now tenting up his shorts, and when she tossed her panties to him he grabbed them and sniffed them with a huge smile. Jenny thought that was odd, but she liked it, and was beginning to like Bill again; yes, very much liking Bill. With that Bill jumped up and hugged her as Bill’s cock popped out of his shorts.
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They pulled away from each other, and simultaneously Jenny grabbed Bill’s cock, and Bill cupped Jenny’s big “C” tits. Holding his cock, Jenny thought that under their strange circumstances she was obliged to suck Bill’s cock at that moment. This was something she had done many times in the distant past, and at that moment actually wanted to pleasure Bill.
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She just dropped to her knees and took his 6 inches in one slurp. Jenny felt very comfortable doing that as Bill’s cock seemed to be very much like her late husband’s. Bill just groaned with pleasure and sat back on the edge of the bed and held Jenny’s head in his hands as she never skipped a beat alternately sucking and licking his cock.
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After a few minutes Bill pulled Jenny’s head away and stood, and laid Jenny down on the bed. He dropped his shorts, got between her legs and spread her wide. Then he asked Jenny if she would play with her pretty cunt for him. Again, she felt this was a cold request if not an order, but she obediently complied. To make matters worse he was instructing what to do, telling her to put one finger in, two fingers in, pull her lips far apart, and then commanded her to rapidly circle and tease her growing clit. Meanwhile Bill was moaning in pleasure, slowly stroking his cock telling her what a good girl she was.
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Jenny could tell Bill was mesmerized and when she saw that look in his eyes, she again began to get that sense of empowerment. Although he was the one giving the orders, she felt that she was actually the one in control. More importantly with that came that sensation of power and along with that, sexual arousal; she was really getting into it and enjoying her little masturbation show for her appreciative audience of one.
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A few minutes later Bill decided he needed a little taste of Jenny’s steamy cunt and started lapping away. She wanted to keep rubbing around her clit, but thought best to let Bill think he could do it better. She let Bill take over completely and just held his head while he teased her cunt. And Bill did manage to keep her very aroused with his talented tongue.
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That did not last long either as Bill slid up on top of Jenny and easily slipped his cock into her sopping wet pussy. After just a few strokes he grabbed her close and rolled over leaving Jenny on top which allowed him to play with her hanging tits and tug on her hard nipples. Jenny did not have a lot of experience riding on top; she and her husband seldom did that.
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But she soon realized how much she liked riding Bill. It allowed her to move and position herself for maximum pleasure, grinding her clit against Bill at just the right angle and pressure as she needed. So Jenny was now in control and it wasn’t long before the first small wave of orgasm crossed by, then another, then the big one as she cried out. But Bill hadn’t cum yet so she kept up the pace while taking the pressure off her clit, and Bill soon erupted filling her with his cum.
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They rolled over to be side by side and for only second time during the tryst did they kiss. And a long and passionate kiss it was. But slowly Bill pulled away and said that they needed to call it a night that he needed to get home. It never occurred to Jenny to even wonder if Bill was married or not, maybe because she never saw a wedding band. And maybe because it just did not matter to Jenny.
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Bill took a quick shower alone and asked that Jenny stay naked so he could enjoy her beauty. She thought that since he put it that way, she didn’t mind at all. At that point she enjoyed Bill ogling her. Bill apologized as he dressed and said he was late and he hoped she didn’t mind him leaving her there. He told her she could shower and leave whenever she liked. With that she felt truly used. The word whore came to mind, but she blocked that out.
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Jenny thanked Bill for an exciting and interesting evening, and apologized for her lack of enthusiasm at times and being a clumsy lover. She told him that she had not had sex in two years and never with anyone other than her husband. Bill was astounded by that revelation and assured her she was the perfect lover. Jenny thanked him for his kind words.
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Since Bill had not mentioned anything, she felt she needed to ask Bill if he had found any other solutions to her financial situation. Bill apologized and said he got so caught up with her beauty and passion that it slipped his mind. He said yes, that he discussed her situation with a friend who worked in upper management of their financial department. Their conclusion was that they had come up with a plan that could possibly work out. Then Bill said that since tonight’s meeting went so well, that there is an excellent chance that a solution far better than she had hoped for was possible.
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Bill told Jenny to keep Wednesday evening open next week so the three of them can meet and discuss it further. Bill saw the shocked look on Jenny’s face and he told her not to worry, that he was sure she would really like his friend George. And in parting Bill added; “if things work out next week, you would not need to not worry about your next mortgage payment and possibly other payments far into the future”. Bill gave her a big kiss and walked out the door leaving a stunned and still-naked Jenny with her head spinning, wondering what she had gotten herself into.
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