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TITLE: Jenny’s Financial Dilemma Pt 3
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LOCATION: Steve - USA
AGE: 31 - 40
VOTES: 0
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To sum up parts I & II, Jenny was an attractive 34 year old widow with 3 kids to support and near bankruptcy. In a just one evening she teased, sucked and fucked three influential guys who literally held the keys to her future. It was a huge step for Jenny; until just a week earlier the sexually naïve MILF had only ever had sex with her late husband. But she told herself she was doing it all for her kids; but she was confused as to why she was looking forward to future meetings. Was she enjoying the attention?

The Friday after Jenny’s meeting-turned-orgy with Bill and George-the-mortgage-guy, and Sean-the-Lexus-dealer, Jenny met with Sean as he requested. As Sean instructed, she cleaned out her old car and arrived at 11:00 AM with her old lease agreement in hand. A salesman had Sean paged, and he met Jenny with a very business-like handshake. Sean then escorted her to his plush office, locked the door and they briefly discussed the agreement. No papers were signed, Sean simply told Jenny that he would close out the old lease, and that her new Lexus would be registered as a complimentary vehicle in the dealership name.

Sean grabbed a set off keys that were on his desk, handed them to Jenny and asked if she wanted to see her new car as he opened the office door. Jenny expected that she’d have to fuck Sean, or at least give him a blow-job right in his office to seal the deal, but apparently not. Jenny was ecstatic when she saw her new Lexus SUV. Sean got behind the wheel and told her to hop in and they’d take a ride as he showed her all the features of the car.

While still front of the dealership with people constantly walking by, Sean told Jenny that he’d really like it if she would take off her clothes and toss them far into the back. Jenny froze in shock, but Sean just smiled with a raised eyebrow. “Here? Now? There are people all around!” Sean just smiled and told her that while the windows do not appear to be, they are indeed tinted. As she slowly undressed, Sean purposely drove slowly past customers and sales people who showed no reaction to the now-nude lady just feet from them. But Sean warned her not to roll her window down! Jenny had to laugh at that which relieved some of the tension in the car.

Jenny asked why he wanted to humiliate her like that. Sean said “I’ll bet you got a little rush from that, didn’t you?” Jenny had to think about it, and realized he was right, then nodded her head in agreement. Sean told her that besides that, he loved to look at her and said “George was right; you really have no idea just how beautiful you are.” Jenny could feel herself blushing, not because of being naked, but rather because of the compliment. Sean drove right out of town and they were soon on a well-traveled rural road with nothing but woods on either side. Sean asked Jenny to show him her luscious shaved cunt. Without another thought, she threw her left leg over the console and faced him, spread wide and touched herself. Sean just mumbled, “oh yeah”! Jenny was starting to feel aroused; she felt oh-so-naughty, nude in a car, driving on the road and playing with herself while thoroughly enjoying it.

Sean told her he needed to taste her sweet cunt but it would just be a few minutes to their destination. Jenny asked where they were going. He told her that since it was such a warm and beautiful summer day, that he thought she’d like to have a picnic at a very private and special place. Sean soon turned off the road onto a gravel driveway into the woods. There was a chain across the driveway and large no hunting and no trespassing signs. Sean jumped out and unlocked the chain and let it drop to the ground and drove in, putting the chain back up after they passed through. As they were slowly proceeding down the narrow and overgrown driveway Jenny had to ask if they were allowed to be there. Sean chuckled and said that yes, since he owned the property and had hopes of building a home there.

After driving a few hundred yards they came to a grassy clearing in the woods which opened up to a sizeable stream running by. Sean shut off the engine and jumped out telling Jenny that “here is a little piece of paradise!” It was a very remote and peaceful area, and Jenny danced naked around the clearing like she had not a care in the world. Sean took sight of her great body highlighted by her awesome "C" cup tits with a natural MILF droop and large nipples. Sean opened the back of the SUV and pulled out a big quilted blanket; He threw the blanket out on the grass and motioned for Jenny to lay on it as Sean pulled off his business suit. He told Jenny he had some water, beer, wine and sandwiches in a cooler and backpack; but he told her that she was looked so hot that he just had to make love to her first.

Lying on the blanket, Jenny asked if any boats ever came by. Sean said that there were never any boats; while there was a nice deep pool right in front of them, it was very shallow and rocky in both directions. With that Jenny struck her most sexy pose, and they were soon locked in an embrace and kissing. Sean started to suck on Jenny’s nipples and she reached for his cock which was already rock hard. It didn’t take long for Sean to slip between Jenny’s legs and taste her sweet cunt briefly before he slid his cock into her warm depths.

Sean took the advice George had given him the last time they were all together; he began to gently twist and pinch her nipples and in just minutes they were both moaning and grunting as they both came. Only seconds later they were shocked to hear clapping, and as Sean rolled off Jenny, they saw two guys in a canoe just 25 feet away applauding them! The guys were smiling from ear to ear, and called out “bravo, bravo!!” Then one yelled “encore, encore!” Jenny would have been mortified if this had happened just weeks ago, but things were changing fast for her. She could only laugh at their antics, and Sean started laughing too. The guys sensed that they were not an embarrassed and angry couple as they might have expected, but seemed unashamed by being caught in a sex act while totally nude and making no effort to cover up.

Emboldened by Sean and Jenny’s casual attitude, the two guys and stepped out of their canoe and dragged it up onto the grass. Sean and Jenny did not expect them to do that, and for sure did NOT expect that these guys were also naked except for flotation vests. Jenny felt a lot more vulnerable and wary than she did when they were in their canoe; Jenny stayed on the blanket while Sean stood up. Both the guys were younger, big and husky, but most notable was that the taller guy was totally shaved. That was a first for Jenny; she had never seen a guy with a shaved cock, shaved everything.

Neither made and apology for intruding, and were ogling Jenny constantly. Jenny realized she was ogling too, because the shaved guy had a really big cock, or maybe it was an illusion because he was shaved. Jenny decided that no, it was just big, and wondered how big it was when at full staff. The other guy had a more average sized cock and pubic hair but was surely far past limp, but looked strange to her, and would learn that he had not been circumcised.

The taller guy said he was glad to come across fellow nudists instead of anyone else because that would have been embarrassing or worse. He continued on and said that he and his buddy were canoeing with a group of nudists on the river and they decided to take a fork around an island. They understood it to be a shortcut and they planned to surprise the others. But that was quite a while ago and they had to struggle through some shallow and rocky areas. Sean told them that it wasn’t an island at all, but that they were going up a tributary which only gets smaller, and they needed to go back the way they came.

The guys stared at each other and their dismay was obvious. The guys asked if they had any water, saying that they had been paddling for hours and the drinks and food was in their girlfriend’s canoe, and all the had in theirs was camping gear. Sean offered them some bottled water and waved them toward the back of the SUV. They eagerly drank the water and thanked Sean profusely. Sean had to correct them, that he and Jenny weren’t nudists at all, just lovers who were nude. Everyone had a good laugh with that.

The taller shaved guy introduced himself as Bob and his pal Lou introduced himself as well. Bob admitted that he and Lou weren’t nudists until recently. Bob’s new girlfriend had been a life-long nudist and convinced him along with Lou and his Lou’s girlfriend to attend a nude gathering and they all took a liking to it.

With the conversation going well, Jenny was feeling more secure with these guys and got up herself to get something to drink. She then realized it may have been a mistake, as she felt Sean’s cum running down her leg and hoped it wasn’t that obvious. Then Sean grabbed himself an IPA beer an offered the guys one as well while he uncorked a bottle of red and poured Jenny a glass. Sean also broke out the sandwiches and chips that he had brought. The guys all sat on or leaned against the back of the SUV while Jenny thought it best to sit back down on the blanket facing them.

Along with some small talk and another round of beer and wine, Sean steered the conversation around to asking Lou why he hadn’t been circumcised; Sean added that he didn’t think that Jenny had never seen an uncircumcised cock. Lou took the cue and was happy to walk over to Jenny sliding back his foreskin so she could get a good look as his cock grew with the stimulation and attention. A wide-eyed Jenny didn’t know what to say with that.

Then Sean asked Bob why he would shave his cock and balls. For Jenny it was becoming clear that since Sean had purposely brought genitalia into the conversation it could only mean one thing; Sean was planning for Jenny to have a very busy afternoon. Bob told Sean that he shaved because it really felt great as he took his cock in his hand and he started to slowly stroke it while locking eyes with Jenny. Bob also mentioned that it was his girlfriend’s idea, and it certainly made him very popular at the nudist events.

Then Bob said “let’s ask Jenny why she shaves her cunt bare”. Jenny had been sitting cross-legged just ten feet away and facing the guys. Jenny just said “Bob is right, it really felt great to be shaved” as she slowly uncrossed her legs and put herself on display. While her eyes were locked on Bob’s growing cock, she ran two fingers the length of her swollen lips to the astonishment of the three guys.

That was when Jenny saw Sean smile in approval and start to stroke his cock. Jenny figured since this was what Sean wanted, she was going to try to please him. Jenny motioned for Bob to come closer and she gently took his shaved balls in her hands and toyed with them as she teasingly licked the head of Bob’s growing cock. Jenny dismissed Bob, and asked Lou to show her his uncircumcised cock up close, and Jenny couldn’t wait to wet her fingers and play with it until Lou was at full attention. Jenny turned her attention to herself and spread herself wider, and just kept slowly caressing her wet and cum soaked cunt, sliding her fingers up and down, briefly circling her clit, and stroking again, dipping a finger in, and repeating this over and over. Then with her other hand she started to pinch and pull her nipples. Meanwhile all three guys were gathered around her and slowly stroking their cocks to full arousal, and Jenny couldn’t believe how big and fat Bob’s cock had gotten! Last week when she saw George’s cock, she didn’t think they could be any bigger, but Bob’s definitely looked longer, but maybe not quite as fat.

Jenny picked up the pace by shoving three fingers into herself and finally blurted out, “fuck me Sean, now!” And Jenny rolled over and got up and all fours and wiggled her ass as Sean drops to his knees and slammed it home. She soon saw that Bob and Lou were now kneeling in front of her pulling on their cocks just inches from her face. She knew she just had to have that huge shaved cock and briefly lifted one hand up and pulled Bob’s cock into her mouth. Bob held Jenny’s head in both his hands as she did her best to suck on that monster. Jenny could tell that Sean liked her sucking Bob’s cock because Sean immediately started grunting and picked up the pace and within minutes shot another load into her. Being down on all fours she couldn’t see, but Sean must have motioned for Bob to take his place. Bob pulled his cock out of her mouth just as Sean pulled out of her, and a moment later she felt Bob’s monster stretching its way into her cum drenched cunt.

Jenny thought about how awesome her orgasm would be if she could control it, and she lurched forward and pulled away from Bob and stood up. Everyone was surprised, but she told Bob to lie down on his back, and she sat on his big cock and guided it into her while she moaned in pleasure. While she slowly rocked back and forth on Bob’s big cock she motioned Sean to come to her and she took his cock into her mouth and licked and sucked him clean. Then suddenly Jenny pushed Sean away and looked skyward as she rode Bob’s cock hard for a few seconds and tensed up and let out a scream of pleasure. After a moment of remaining motionless, Jenny again began slowly rocking back and forth on Bob’s cock and reached out for Lou’s cock.

Lou hadn’t gotten any attention and Jenny wanted to have that uncircumcised cock in her mouth. Still rocking on Bob’s cock she worked on Lou’s cock and was surprised that in just a few minutes of sucking and playing with his balls, Lou was ready to unload. And he really did unload. Jenny had never seen so much cum as she gagged and Lou pulled out still spurting on her face and tits. Paying no attention to the cum all over her, Jenny sat upright and kept riding Bob. Then Jenny felt Sean’s hands on her ass and back, pushing her downward, and felt Sean’s finger playing with her virgin asshole. That was a sensation she had never felt and was concerned. Soon Sean’s well lubricated finger was deep in her ass and she slowed her pace pumping on Bob and was concentrating on this new invasion into her body. Sean pulled his finger out briefly, and then she felt two fingers sliding in with more lubricant. She was starting to like that sensation.

While she still slowly rocked on Bob’s big cock, Sean pulled his fingers out of the butthole again, and with more lube, she felt something much bigger trying to enter. Sean told her to push out to make it easier. Before long Jenny had two cocks in her body, and one was really big; it was quite a sensation for her. To finish the trifecta, Lou was waving his half-hard cock in her face and she took him in her mouth again. By the time Sean inched his way completely inside Jenny, she exploded into another orgasm. Sean and Bob had stopped moving and Lou pulled out to let Jenny recover as she slowly rocked back and forth. But Jenny wasn’t done just yet, she started picking up the pace as she pulled Lou's cock back into her mouth. Bob was now reaching his peak, and unloaded into Jenny grunting and moaning just as Jenny spit Lou out to concentrate on a screaming orgasm. Seconds later she yanked herself off the guys. Jenny collapsed in a heap lying on the blanket face up, legs splayed.

When Jenny regained her composure she realized Lou was kneeling over her wanking his cock. Jenny could not believe it, and declared that she was sore, aching and done. But she smiled at Lou and invited him to cum on her tits, and Lou kept stroking away and unloaded more cum on Jenny. Then she saw Sean and Lou were standing there holding their half-hard cocks. Jenny asked how they could be such horny guys. Simultaneously they just said “because of you!” Sean asked a smiling Jenny to spread her beautiful cunt and she complied. Lou was totally spent but got behind Jenny and was massaging her neck and scalp, putting her in a dream-like state.

But now Sean started jacking away, and a revived Bob followed his lead spurred on by Jenny lying there near lifeless except for slowly fingering her cunt and gently playing with her nipples. She was soon spattered by two more loads of cum leaving all the guys pumped dry. Jenny was such a mess by now it made no difference, so she thoroughly enjoyed smearing the sticky cum all over her body, especially her tits. When the two strangers recovered, they jumped in the stream to clean up and put on their flotation vests. As they went canoeing away they were thanking Sean and Jenny over and over for their hospitality and mumbling that their girlfriends probably thought they were lost in the wilderness.

Sean suggested to Jenny that they get washed up too, and Sean got a bar of soap from the backpack and helped Jenny down into the steam where they scrubbed each other well. Sean had brought them each a towel, and they were soon dressed and back on the road with Jenny behind the wheel of her new SUV. Jenny was thrilled to have such a great car with no payments; she wondered what the ultimate “cost” of her new Lexus would actually be, especially now knowing that Sean was much like George-the-mortgage guy. Both were guys who “get off” on displaying and sharing her. Jenny wondered what her next challenge would entail; George had asked her to be his date the following weekend and attend a friend’s couples-only house party. Jenny had a suspicion that it would not be an ordinary house party.

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