Did we Cross the Line Yet? Pt. 03

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Husband Lost Bet! - Payoff, Jerk Off Nude on Trail for MILFs.
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Part 3 of the 3 part series

Updated 06/11/2023
Created 07/16/2022
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inafantasy
inafantasy
904 Followers

Part 3 of a fictional story directly from my sick mind. It is a continuation of Parts 1 and 2 but stands on its own. All characters portrayed are well over the age of 18. Self-proofed and edited with the help of software, so some mistakes are possible. Comments on the storyline are always appreciated.

Ronnie could not wait to and told Marty the whole story of her seduction and bedding of the neighbor boy. Part of her excitement was that there was a payoff for her from Marty. A bet had been made with him that she could seduce and bed the college student neighbor in the short span of a couple of days he was on a business trip. Marty underestimated her, the fact that the neighbor was both backward and was studying to be a minister made him think he would resist her longer than his trip.

Marty thought she might not even be able to do it at all. He made the bet despite it being a blind bet as far as what the payoff might be. it was hard to imagine what he was going to have to do to settle it. Ronnie had already decided the basics of what it would be if she won. It was going to be some kind of solo naked act by Marty as the loser. He has never done one alone, and this one was going to have more involved than a short stroll in some public area au-natural.

It took her a couple of weeks to come up with a working plan for the payoff of the bet. It had to and was going to be up to her standards daring-wise. She wanted it to be one that she knew he would refuse to do, and try to get out of. She also wanted it to be something she would enjoy seeing go down. She felt when he made her walk downtown naked with him, even though he was nude with her, it was to fulfill one of his fantasies of showing her off to strangers. This had to be something that showed him off, but for her enjoyment.

The more he thought about what she might come up with, the more it scared him. She was quite a wizard at setting up things like that, he knew whatever it was, that it would be radical.

Ronnie was running on occasion at a local park to keep fit. Keeping her youthful look and fitness was important to her. Her looks and fit body were key to her getting men of all ages to want her. Her big breasts her shaved pussy, and her tight body with not a bit of fat were so very important when it came to exposing herself to them. Ronnie, after living a sheltered life in the church herself found out that she loved using her naked body to seduce men. She had mentioned to her husband that if there were more men on the trail she would like to run there topless or even naked sometime. Just the thought of seducing, and fucking a strange man in the woods would usually work to Marty's benefit, as she would then satisfy that craving by fucking her main man.

Ronnie realized after running there a month or two that it was almost entirely a female crowd, making it not very daring for her to even run topless. It was not just a place for women to run, it was kind of a gathering place for other horny women. Most women had a partner, and that made Ronnie assume for a while that maybe it was a place for lesbians to hook up. In truth, it was just an area that was used as both a cool-down and gathering place for talk and gossip. She then realized hook-ups by women was not necessarily the purpose of them gathering there. It was mostly talking about men that went on there. The rare ones that they might have encountered on the trail, and what they wanted to do with them.

Yes, there were some gay female couples, but most of the pairs, or threes, were just running with their friends. It was made clear by the way they would talk about men that most of them were straight.

She figured since he already walked downtown nude through a crowd of people, he could walk or run on a trail with an occasional passerby.

Ronnie was not out of place as a female using the park and trail scantly clad, it was used by mostly women, of all ages. She was surprised more men did not come just to enjoy the view or try to pick up one of the horny and primarily young ladies. Ronnie noticed that like herself, knowing that not many men had been spotted, many of the women wore little as far as clothes just in case. It was like she found a place where other women wanted to expose themselves, but lacked the courage to go as far as running nude. Instead, they wore as little as possible, but rarely was a man there to pay attention. She had seen more men in the parking lot, and she found out that they normally used a more challenging trail that went through the same woods, and was visible in some areas.

Ronnie found all that out when she heard one of the girls that runs in nothing but thin nylon shorts and a top. She was telling some others about how turned on she got when she encountered a hot lone guy. She said maybe he had been running on the other trail and spotted her coming through the trees. He stood in between the two trails, and took a break for a drink, then became a flasher. First, she thought he was taking a pee when he just pulled out his sizable penis. When she saw it was sizable because it was already hard, she knew he was excited and intended to expose himself.

He soon proved to her that he wanted her to see him. The woman and the other girls she was telling it to were more excited about maybe getting to see him than they were fearful of a possible pervert on their trail. They may deny it, but women especially ones that have been married a while, are just as excited to see exposed men as men are to see women.

Then the woman described the whole encounter in detail to an attentive crowd of horny women.

She told them, "He was hot, I mean really built, and hung. When he saw that I was looking at him instead of running away, he stepped out into a clear area and came closer to be seen better. I was kind of frozen in a stare. He returned the stare and was ready to show more, so he shed all his clothes and was standing there naked and aroused for me."

"I stood my ground I wanted more from this encounter than just the view of a naked hunk with a hard penis. I decided that I was not going to leave until he gave it to me, I wanted a show from him. I am not sure if he planned to do what he did, but since I didn't leave, he started playing with himself right there in front of me. The demonstration of his fondness for his package was enjoyable. But the show got better when he got pretty serious about his play and soon was just plain jerking off for me. His fitness and the size of his manhood made it a pretty hot scene, so I was glued there. I felt myself getting wet, and I had to put a hand down my shorts."

"At this point, he was looking down at his package, but if he would have focused on me I was going to try to get the courage to at least lose my top. I even thought about joining him nude and taking care of myself in front of him. He was just so hot standing there nude, and pumping his hard cock."

"He stayed with it as he tried not to let me see him looking back. It did not take long for him to cum with me watching him. Soon he was pumping what seemed like endless ropes of cum in my direction, he looked in such pleasure. You know how guys are, he was then so proud of himself as he shook off the cum dripping from his cock. I never had a guy look that pleased even when I have jerked or sucked him off. Once he finished and had shaken off the lingering cum ropes, he turned and walked away. He left me so turned on, I dropped my shorts, and while imagining he was still there watching, I finished taking care of myself as he disappeared into the woods toward the other trail."

It sounded to Ronnie like she may have been embellishing the story of the flasher, but she was glad she did, as it gave her a plan. The surrounding girls seemed a little shocked, some did not believe her, but no one was not turned on. Several of them had questions for her. Ronnie had never seen so many hard nipples showing through running clothes at once.

They all wanted to hear more. She got the impression right then, that it was not to avoid him, but wanted to be the next one to see him. They wanted the location and information on what he looked like, was he really that cute, and hung? The next time she ran she could see that a lot of the girls that had not been running in very little, now were. All this planted the seed for what she had in store for Marty.

Ronnie talked to three different women she thought looked the most excited while hearing the story, and one seemed to show the most interest in not just seeing him, but hopefully getting to see him get off. She talked about it enough for Ronnie to know that she would most likely be game for the scheme she had brewing in her mind.

This woman was a little older than her but not quite a mature, very much what men describe as a MILF, just a little on the fuller figure side, and trying to rectify that by running. One day their conversation got into the fringes of a sexual one. The next time she saw her the conversation got a little more sexual. They talked about sex, men, and how badly she needed one. She said that she was trying to make herself more attractive to maybe catch the guy's eye. That statement triggered the beginning of her planning, Marty was in trouble, this was going to have more involved in it than just showing himself naked, and then escaping.

Seeing Marty just naked after the embellished story told to them was not going to do it for any of these girls, especially the MILF. She knew that someone with a penis standing by the trail naked would stand out, but they were going to expect to see a guy playing with himself.

A few weeks later she put some more bait out there and set things up to be sure Marty would be seen by her. Ronnie decided to tell this MILF a made-up story that she had seen this flasher more than once and was not sure he was the same one as he seemed even more anxious to be seen.

She told her, "The first time, he was naked carrying his clothes. He spotted me and had to notice I was staring at his junk, he then stopped and left abruptly, he seemed to be spooked like he saw or heard others coming. The next time I spotted him cutting through the woods to our trail. This time he was bolder and once he was on our trail he was even running toward me. He slowed down like he wanted to give me more time to see him and more time for himself to enjoy being watched."

The woman she now knew as Doris was excited and said, "Did he stop and jerk for you, did you get to see him get off?"

"Well, yes to both I guess, it was clear he wanted me to see him. So I stopped and acted like I was trying to block the trail. He slowed up even more and finally stopped a few yards from me. Then his hand went down there and was giving his junk some stimulation. So I figured why not watch, so I held my ground and I did. I could not believe he was not just totally nude but seemed to have no clothes with him, he had been running that way. Soon he was jerking for me, and really into it. He was one hot daddy, with a nice cock. He is more of an exhibitionist than an everyday flasher. He sure put on a show for me! He treated me to quite a nice cumshot, he looked like he had been saving up for his performance."

I knew I had to sell her on the fact that I did see him. So I just continued to make up that story on the spot since she seemed to be believing me.

"The next time I saw him through the woods further away, and he had shorts and a tee on. Then I could tell he spotted me, and he stripped and hid his clothes behind a bush before switching to our trail. I hoped for another hot show and was about to get one. Once he got to me I saw that I had his attention, he was not afraid to make eye contact. So I escalated things and dropped my shorts and put my foot up on a nearby stump to expose my pussy and made sure he had enough inspiration. He was close this time, so first I took both hands and opened up my pussy lips to show him my pink as I fingered myself. I am glad I did, he was then fully erect and jerking off. I don't think many of us girls get to see guys jerk and cum, even though a lot of them expect us to expose and diddle ourselves for them."

"The more I fingered myself the more intense his jerking became, he again was pretty serious about getting off while being watched. I had to assume that is not a rapist modus operandi, or he would have been aggressive. Bottom line was that this guy was serious about being seen or he would not have been naked, flashers usually just drop their shorts down. I guess he likes the extra danger of not having his clothes even next to him."

"He was really into getting into his masturbation as he looked at me now doing the same. I was prepared to just mutually masturbate, but watching turned me on to the point I probably would have blown or even fucked him if he made the first move. He focused on me when it was time to cum, he moved a little closer, first scaring me, but then I realized he just wanted to be closer when he came. That was fine, as I love seeing cum as it leaves a hard cock. I guess I forgot the velocity of the first few ropes of cum from a guy and how far they go. A couple hit my belly, then the rest just left a trail on the ground from him to me.

"He looked more than a little surprised, finding someone willing to not just stay and watch but to drop her shorts and masturbate with him. I guess my husband being out of town made me extra horny that day. I think we both were fueled by not just each other, but also the thought that someone else would spot us. I was a little disappointed as I saw him turn and jog back to where he dropped his clothes. Then I watched him dress and fade away in the distance."

This woman named Doris was just so excited, she said she had not had, or seen a man's cock since her man left her. Ronnie felt lucky to have found her and did a great job at making something so crazy believable.

Doris told her, "I would have fucked him for sure if he even hinted that he wanted me, I am not blessed with a fit body like you, I can't be choosy!"

Ronnie did not want her to feel that way and told her that no guy with a hard-on could pass on a good-looking woman with breasts like hers, age would not stop him. She wanted to know when and exactly where this happened. Ronnie said both times it was on Wednesdays, and some of the reports from the others were on the same day, and about the same time. Doris was excited about trying to meet up with him and setting it up with her, so she picked a spot on the trail she could describe and told her it was there that it happened.

Ronnie could not wait to tell Marty what was planned for him, he was going to freak out, she was going to make him be that man not just naked in the woods, but jerking off for Doris as well. Ronnie was so proud of herself, it was luck to meet this lady.

She had her plan, but still had some details to work out. She knew this was a major escalation of their public nudity, and pushing the definition of exhibitionism, but she knew he would do it for her. Despite all she puts him through he seems to love her enough to do about anything.

Ronnie broke the news about the plan, a little at a time as it was even more radical than the story she made up. First, she told him he would be jogging nude. He objected to that but eventually gave in. Then once he settled down she added the masturbating part, and as predicted he went ballistic. He told her that getting arrested during a sexual act like jerking off was much worse than just being nude in public, a minor misdemeanor. He told her it was too much and was willing to just jog nude a short way down the trail with clothes in hand.

She countered that this was already set up for him to be both nude and jerking, but it was going to be under a controlled environment. Ronnie told her the woman she had lined up was expecting to see a guy doing just that, so she would not be calling for help or reporting him. She added that no rules were made on this bet, and he agreed to it, and she already had a woman expecting a hot naked man just waiting for a woman to jerk off for. Marty was not happy but eventually quit protesting, he knew how relentless she could be.

She decided that he needed to be in on the planning, and told him to dress like a runner, so they could go to the park to go over the plan, a kind of rehearsal. They trotted down the trail together, and she took him to the spot where she told Doris the fictitious story about how she encountered the flasher twice. It was right after a bend in the trail that would fit the description she gave her. She showed him where to stand, and told him to show her how he was going to do it. "You want me to be dick out and jerking as she comes walking up? That is crazy."

"She is expecting to see you not just with dick out, but waiting naked, and eventually jerking off a load for her."

She told him to quit stalling, and lose his shirt and shorts, and of course, a well-argued protest followed on his part as he stripped them off and stood naked in front of her. So he lost that protest too, along with his shorts and shirt. She held his clothes as he stood there nude for her as a rehearsal. She still had not broken the news to him that when he did it, he would not have access to anything in the woods but his water bottle, she did not want him to have his clothes close by in case he chickened out. He looked so sexy standing there naked, her big tough man looked vulnerable. She then told him to start stroking his dick, as she stood clothed with him. This was just for her, she got wet thinking about it being a stranger, Doris. She thought of a way to make him look better, and told him to use the water bottle to stimulate sweat on his waxed ripped chest, he had a nice body to show.

He did, he poured some water down his chest, as she told him how hot and fit he was. He must have been a little turned on doing it, as it did not take him long to get rock-hard or to cum under these circumstances. Ronnie held his balls as he emptied them on the trail. He enjoyed jerking and getting off for her, even though he had done it before. This was on a public trail and in a CFNM situation. He asked for his clothes for this trip back to the car, it was time to tell him that the next time, he would have to walk back nude to where she was waiting with his clothes. So this although not solo, would help prepare him for that.

Ronnie told him that way she would know he kept his word. He was done arguing and they started walking. They encountered one girl jogging before getting close to the parking lot. It was probably a good thing, as she looked pretty surprised, but did not stop. She also saw by the look on his face he liked being seen. For the girl, seeing Ronnie holding his clothes may have made her think this was just something like a lost bet, and in fact, it was. She let him dress before they got to the parking lot.

She got him there early on the day of the actual stunt, she needed to. The first step was to take him to the spot again where he was to do it. He stripped, and stood there naked as he argued with her yet again when she would not let go of his clothes. He begged her to leave them and promised he would only go for them in an emergency, but Ronnie had this whole thing in her head and was sticking to it. He then realized he could be standing there naked and dick out for at least 15 minutes or longer waiting, and other women likely could come by. She pointed out to him that her walking naked downtown with her clothes clear back at the car was like this, and it was his plan that she didn't argue with it.

So there he was, standing nude near the trail with nothing but a water bottle, and a partially excited dick. Fortunately, she sprayed him with bug repellent, as some bugs were buzzing around. He found a fresh tree stump, he figured he could probably sit on it without getting a splinter. He noticed it was close to some bushes he could get to if things went bad. It gave him time to think, and he did. He wondered what he should do if her description of the woman was not as good as Ronnie said it was. What if he jerked off for the wrong one, surprised one that was not into it, and had mace? He pictured himself running naked, and then blindly from being sprayed. He would have to run through the trees while trying not to collide with one.

inafantasy
inafantasy
904 Followers
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