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TITLE: Jenny’s Financial Dilemma Pt 2
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LOCATION: Steve - USA
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To sum up part I, Jenny is an attractive 34 year old widow with 3 kids to support and in jeopardy of mortgage and car lease default. After contacting her mortgage manager the sexually inexperienced Jenny had not much choice but to suck and fuck Bill that night; worse yet he told her they needed to meet again in a week along with his boss George and possibly a third guy to work out details. During that week Jenny was emotional wreck thinking about the meeting with these guys. But she tried to think positive thoughts in spite of the fact that she was convinced that she would be getting sexually ravaged by a few men.

When the night came, she again dressed nicely to accent her attractive figure, yet not overly provocative. When they met at the restaurant, Jenny was pleasantly surprised to find that Bill's boss George was a tall and strikingly handsome man with a full head of silver-grey hair, but appeared to be well into his 50’s. For a brief moment Jenny thought that in a short while she might be in bed with someone who could be old enough to be her father. Jenny was relieved to see it was just the two of them.

During dinner Jenny broached the question of solutions to her mortgage troubles while she was starting on her second martini. George answered by saying that he and Bill determined that if things worked out as they had hoped, she would not need to not worry about her mortgage payments far into the future. Jenny asked what he meant by “things working out”, George wavered a bit but then told her quite bluntly, “it really depends on your approach to what you can do for us and others”. The “and others” really sent Jenny reeling; Jenny just blurted out “and others?”

George realized she was shocked and quickly added that he was referring to additional help in regards to her defaulting car lease. He said that another friend who could help her with that might stop by later. George also mentioned that he might be able to find other avenues for her to get her head above water. She was about to become a sex toy for a group of men, plain and simple. A small price to pay for keeping her family together is what she kept telling herself.

As soon they were inside the suite Jenny excused herself to freshen up, and soon came out from the bathroom in her very sexy barely-there bra & nearly transparent panties, bucked up her courage and came out strutting like a runway model. Both guys whistled which lifted her spirits; she loved the attention.

George got some music going which was nice, and she danced around and began slowly stripping like she did for Bill. When she finally bared her natural “C” cup tits, Jenny got a rush by seeing George’s eyes get big as saucers. Then she had an idea; since both men were now sitting in chairs, she decided to try lap-dances. When she started with Bill, grinding her barely cover cunt on is hardening cock. Jenny slid down to her knees and undid his pants and helped Bill wiggle out of them. She took his half hard cock in her mouth and worked it to rock hard in seconds.

Jenny stepped away and told Bill to stroke his cock while he watched her and George. With her panties still on, she climbed on George and started grinding away as he played with her tits. While he was doing that she undid his shirt and was impressed to find a buff and shaved chest that she ran her hands all over. George obviously worked out often.

Jenny then slid down to her knees and teasingly she unbuckled his belt and unzipped his pants and helped him wiggle out of them leaving him in just his stretchy nylon briefs. And there she saw a very big cock going sideways trying to escape the confines of his briefs. Jenny couldn’t wait to touch it and told him that she didn’t know a cock could be so big. George liked hearing that and told her it was only 7 inches; she thought that if Bill’s was 6 inches, this had to be at least 8 inches and was also very fat. By now Jenny was so hot she wanted to spin around and sit right on it.

But she thought about her mission to please these guys. She thought it might be best to continue teasing them. But she just had to have that cock in her mouth, even if briefly, and she pulled it out of his briefs and took it in her mouth as much as she could and slurped and licked it. His cock was now hard as stone and aimed at his neck and as she pulled his briefs over it, there was a couple inches sticking out the top.

Jenny unceremoniously pulled her own panties off and climbed on top of George, grinding and sliding her bare cunt along George’s big nylon-covered shaft. George was massaging her tits when Jenny started moaning and whimpering. She was having an orgasm without penetrations or manual stimulation. Panting and puffing, Jenny climbed off George and pulled his cock out of his briefs, gave it a quick kiss and told George to stroke his cock for a few minutes while he watched her with Bill.

Bill was wide-eyed in anticipation and still stroking his cock as Jenny knelt before him and took his cock in her mouth to the hilt in one slow slurp. Jenny cupped Bill’s balls and sucked on Bill’s cock until she thought he was near cumming. Then Jenny said she was a little uncomfortable kneeling, and climbed onto the bed.

Once on the huge bed she spread herself wide and started diddling her cunt to the pair of wide-eyed guys. She asked Bill if he would please lick her cunt and he was there in a second. She motioned for George to come up to her and she told him that she really needed to suck his beautiful cock. George’s face lit up and he quickly knelt next to her as she raised herself up on one elbow and slobbered all over his very big fat cock.

Jenny wasn’t very comfortable in that position but really wanted to make George cum. So she asked Bill to lay down face up, and Jenny squatted over his face and lowered herself down and moaned with pleasure telling Bill how much she loved him doing that. Now she was able to suck George’s big cock properly and in just a matter of minutes he was ready to cum and he warned Jenny. Jenny thought she’d be a trooper and swallow it all, but she soon learned how difficult that was, as it spewed out and she gagged getting cum all over her face and neck.

Meanwhile Jenny had hopped off Bill as she wiped her face but smeared the rest of his cum around and let it be. She looked at Bill who was a little shocked with all the excitement but was still rock hard. She told Bill that she really needed someone to fuck her good right then and there. Jenny lay back and Bill smiled and slid right into her and started pounding away and before long he unloaded into Jenny. Jenny was just starting to feel an orgasm building but she needed more for that to happen.

That’s when she saw George standing alongside the bed stroking his hard cock! He had cum just ten minutes ago and was ready again! Jenny asked George if he’d like to try sloppy seconds as Jenny got up on all fours wiggling her ass in his direction. George was on the bed in no time and Jenny motioned for Bill to come over and lay by her so she could suck his limp cock.

Even with Jenny full of slippery cum, when George slid his big cock into jenny for the first time it was a sensation like no other. It felt gigantic and just filled her up. I didn’t take long and Jenny was going over the top. Ecstasy!! For that big moment, she abandoned Bill to focus on her pleasure. George hadn’t cum yet so she just encouraged him to keep on hammering away. To help George she thought she would try riding him and asked him to lie down. She lowered herself onto his big cock and leaned over him, and he cupped her tits as she started grinding and pumping on his cock.

George started pulling and twisting Jenny’s nipples and even with the pain she was surprised to feel pleasure from that; another new sensation for Jenny. By leaning over and riding George she was controlling the perfect angle of penetration; another orgasm was building. Jenny started groaning and then her orgasm came on her fast as George pinched her nipples harder as they both exploded into ecstasy. A spent Jenny just collapsed on George.

Jenny was recovering as George was stroking her hair and kissing face and neck when and she looks over to see a smiling Bill slow stroking his hard cock and looking at her. Jenny chuckled to herself thinking that it is nice to feel wanted, but this is getting to be too much! She felt that she owed Bill a little more attention than what she’d given him.

Jenny smiled at Bill and motioned for him to come closer and coyly asked what she could do to fix his big problem. Bill smiled and said he had something she might like; he walked over to his jacket and got out a large dildo! Jenny was thinking that this evening can’t possibly have any more surprises, but here it was.

Bill asked her to lie back and handed it to her. While Jenny had been sexually inexperienced, she has had a lot of dildo experience at home since becoming a widow. She was wondering how this was going to help Bill get his rocks off. But she started playing with her dildo while George was holding her in his arms and was still gently caressing her. Bill was up close stroking his cock as Jenny started slipping the dildo in and out. She was surprised how much this was exciting Bill which somehow got her starting to feel pleasure too.

It wasn’t long before Bill looked like he was about to cum, and Jenny groaned to him, “Fuck me Bill! Fuck me!” Bill jumped on the bed and started fucking Jenny and in seconds unloaded another batch of cum into her as Jenny grunted while grabbing Bill’s ass and pulling him into her as deep as possible, grinding against him until she had another orgasm as well.

As Bill pulled out, she realized that George was still beside her, gently caressing her. She rolled toward him and they kissed. Soon they were kissing passionately. Someone knocked on the door. A naked George got up and opened the door to let Sean-the-Lexus-dealer walk in. Meanwhile Bill said he needed to get home and excused himself to shower, and was soon dressed and out the door.

Jenny was just lying on the bed trying to figure out how she should be posing her naked-self in front of Sean, the clothed stranger. It seemed nothing she could do would fit the occasion, so she just stood and walked over to Sean as George introduced them as they shook hands. Jenny thought how ridiculous it was to shake hands knowing that in a matter of minutes they’d likely be much more intimate than that.

Sean was a nice looking guy, younger that either Bill or George, and not much old than herself. Jenny was resolved that she’d be servicing yet another guy and figured she just get right to it. But to her shock, Sean said he just stopped in to meet Jenny but had to leave. Jenny surprised herself by feeling disappointment! But then Sean reached out to Jenny as he complimented her on her perfect tits, and cupped them and bent low and took a nipple in his mouth and in a matter of seconds one hand found its way to her cunt.
Jenny reciprocated and rubbed Sean’s crotch and found a fast growing cock through his pants. Sean worked his way to the bed and sat on the edge and Jenny took the cue and dropped to her knees and unzipped Sean’s pants and pulled out his cock. She teased him a bit with her tongue and slowly got to sucking him. Sean’s cock was just a little smaller than Bill’s, but a little fatter. Jenny never gave it any thought that cocks might all be so different.

It didn’t look like Sean was getting anywhere near cumming so Jenny stood up and bent over putting her hands on the edge of the bed wagging her cute ass as Sean kicked his pants off and started pounding her from behind while reaching around and fondling her tits. George was watching all the actions while slowly stroking his own cock and told Sean that Jenny likes her nipples pinched a little. That was all it took and Jenny was starting to moan and Sean was soon pumping another load into Jenny.

George got a damp washcloth for each of them to clean up and Jenny collapsed on the bed. Sean apologized to Jenny and said she had not planned on that, but she was so sexy, he just had to have her right there and then. But said that he did need to leave and whispered in her ear that should bring her old lease agreement to his office on Friday and asked what color Lexus SUV she’d like, and he’d have it ready. Jenny was elated to hear that, even as the image of her bent over his office desk getting fucked flashed before her.

Only a few minutes after Sean left there was a knock at the door again. Jenny looked at George, and he told her that it was room service; he had ordered espresso and desert. George then told Jenny to answer the door, and a shocked Jenny just froze. George told her not to worry; to just act like she was clothed and it wouldn’t be a big deal. Then George said “please, just for me, OK?”

Just as she hesitantly took one step toward the door, the server let himself in while pushing the cart. As the door shut behind him, he turned and his eyes went wide when he saw the beautiful naked Jenny. Wanting to please George, she took his advice and acted as she was fully dressed. She directed the guy to push the cart to the middle of the room while asking him what he had brought. By then George had pulled on his pants and slipped the guy a tip. As the guy left, he was looking over his shoulder at Jenny the whole time. As the door shut, Jenny playfully punched George in the arm and she started laughing hysterically along with George.

Jenny recognized the fact that she was now more than just a whore, she was George’s personal toy. She didn’t care at all; in fact she loved it. She never imagined that all the positive attention from men could be so exhilarating. Back on the bed they were cuddling, caressing and George was holding Jenny close like a lover might. He asked her if she needed to get home right away, because he’d like to stay with her for a while.

Jenny felt as comfortable and secure in George’s arms as she ever had with anyone. But she is baffled as to how a man could be so tender and compassionate, yet invite other men to fuck her and press her to be ogled by a stranger while she was completely naked. And just as confusing to her, is how she could feel such affection for a man that would do those things to her.

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