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Helpful Sister In Law Part 3 The Peeper

Helpful Sister in law – Part 3

See: Helpful Sister in law, oral, masturbation
See: Most Helpful Sister in law

It had actually been some time since Louise and I had gotten back together.

During our last sexual encounter, we had discussed possibly putting together her husband, and her sister, my wife and see if we could get them sexually involved with each other. Before we had any real chance of getting them together, her husband had a massive heart attack, and died in bed during the night. Obviously, everyone was shocked at the suddenness of the attack. He did have a blood pressure issue, and the doctors had put him on Nitro pills, but apparently this did not help him out. We were all saddened at his untimely passing.

I would normally call her once or twice a week at work, and see how she was doing. She was dealing with the usual estate stuff, and it had her kind of down. I managed to get up enough courage to ask her how she was doing sexually since the death of her husband. She said that she was really stressed out since his death, and had been trying to masturbate her self on a frequent basis, in hopes that would reduce some of the stress in her life.

I jokingly suggested that perhaps we needed to have some phone sex to help her out. She was able to get a good laugh about that, and indicated that she never really tried phone sex. I advised her that I had never tried it either, but was willing to give it a shot.

I proceeded to ask her how she was dressed. She worked in a corporate environment, and had to dress in professional business attire. This particular day, she indicated that she was wearing a business suit, and some of her favorite Victoria Secrets black bra and panties. I asked if she could reach down inside her slacks, and rub her pussy for me, which she said she could do, since most of her coworkers had left for lunch. She told me that she had her hand on the outside of her panties, and was rubbing her pussy while talking to me. She indicated that she was starting to get wet and that she moved the crotch of her panties to the side and continued to play with herself. I told her that I was laying on my bed, and jerking off as she was describing her actions.

She told me that as she was masturbating, one of her male bosses had come over to use the copy machine, and that she just couldn’t take her hand away from her pussy. He would glance over to her as if he needed to talk with her, but since she was on the phone, he didn’t seem like he wanted to bother her. She said that she had now reached down inside her panties and had fully aroused her pussy, and was not far from coming. I told her that I had now wrapped the panties that she had previously given me to play with, around my dick, and was also about to cum. I filled her panties with my cum, and Louise indicated that she just came as well.

Before we could go any further, she said her boss was on the way over, and that she had to hang up. He needed her to do some typing for him, and that we would talk later.

Later that night, Louise called me, and seemed a little upset. She said that she had enjoyed the little phone sex episode that we had shared earlier in the day, and that when she came home she got a shower, and was thinking about the fun she had today. She had been sitting in her family room on the couch and drinking a glass of wine. She had released her robe, and again started to masturbate herself, and play with her tits.

She was really into her session, when she thought that she saw someone looking in her window at the back of the condo. She thought that she had probably imagined the peeper, and went back to playing with herself. At this point, she had grabbed one of her toys from her collection, and inserted the dildo into her pussy.

She then became upset, because she was certain that someone was now outside of the condo. That’s why she called me.

I told her I was about five minutes away from the condo, and to just continue to play with herself, and that I would be right there.

I pulled into the condo complex, and it was somewhat isolated, and very dark. I grabbed a flashlight from my car, and headed around the back of the condos, which backs up to a small stream.

As I approached the back, I could see a figure of a male at her window, and he appeared to be totally into masturbating himself while watching my sister in law. I grabbed him by the scruff of his neck, and drug him inside the condo. Louise was slightly shocked. The young man was one of the young men from the complex that she had hired to do some paint work inside her place, and said that he only lived two doors away, and was married with two children. He was very upset that he was caught, and had a hard time not breaking into tears. Louise actually felt somewhat sorry for him at this point. He admitted to us that after the funeral, and doing some work on her condo, he had been peeping into her windows almost every night.

Louise did not want to get him into trouble, and told him that we would not call the police. I wasn’t so sure if we were doing the right thing or not, but he went on to indicate that since the birth of his last child, his wife was not interested in having sex, and that is why he started to peep into windows, and usually just masturbated himself. He never wanted anyone to know that he was watching. He said that he had watched my sister in law playing with herself on several occasions, and that for an older women, he found her to be a very sexual lady.

Now this young man, Michael, was in his early twenties, and Louise is in her early sixties. Louise seemed somewhat thrilled at the thought that a young man would find her that attractive that he would have to jerk off.

Louise moved over next to the young man, as I sat in a chair across from both of them. When she sat next to him, I could see that she had allowed her robe to come undone, and that she was fully exposed. She didn’t seem to want to cover up, so I was enjoying the view, when I realized that Michael had another hard on in his pants. Louise must have seen that as well, and she had reached between his legs, and loosened the belt on his pants, and pulled down his zipper. She reached inside, and pulled out his dick, and started to jerk him off. I was both shocked, and yet enjoying the show at the same time and I couldn’t bring myself to move or say anything at this point.

Louise removed her robe, and was now totally naked in her family room, and Michael was sitting next to her having this older woman jerking him off. He quickly responded, and reached up and was playing with both of her tits, and then he would reach between her legs, and play with her pussy. Both Louise and Michael seemed to be really into the moment.

I had to drop my jeans, and I started to jerk off as well. Louise called me over, and asked me to sit beside her, which I did. At that point, she was now jerking me off, as well as Michael. We were both enjoying the warmth of her hands stroking our cocks, and I could see that Michael had at least two fingers inside of her wet pussy. I was busy sucking on the tit that was close to me, and Michael was working on the other one.

Louise asked that we both stand up in front of her, and she continued to jerk both of us off, and would, in turn take both of us into her mouth. Now I could see that Michael was really enjoying himself, and by now he must be very close to cumming. I could feel the back of her throat as I was pushing my dick into her mouth, and she was jerking off Michael. As a peeper, this apparently was all that Michael could stand, and as Louise was jerking him off, he shot his load all over her face and hair, and some in her small but nice tits. She just kept milking his cock, and took him into her mouth to clean off his cock. While the clean up was taking place, she continued to jerk me off as well, and my first load of cum went directly on her face as well. When she realized that I couldn’t last any longer, she placed me into her mouth, and continued to jerk me off in her mouth until she drained every last drop of cum from my dick.

While she had been busy jerking us both off, she had been somewhat ignored sexually. She asked that someone needed to put a cock into her pussy, and to do it quickly. I was still semi hard, and as Louise continued to suck my dick, I became hard enough to mount Louise and entered her very hot and wet pussy. Michael was playing with himself, and he had himself hard again. As Louise was lying on the couch, and getting her pussy filled with my dick, Michael had mounted her face, and was now fucking her mouth. Louise was giving out some verbal indications that she was really getting pleasured, and close to cumming. She was telling Michael how much she was enjoying her eight inch dick, which also had some girth to it as well. Well at this point, Michael started to fill her mouth with his hot cum. Seeing this, I started to fill her pussy with my hot cum, and as Louise was now cumming all over my dick. I could feel her pussy tugging on my dick. I could see that Louise had now removed Michael’s dick from her mouth and continued to stroke his dick.

We were all pretty well spent at this time, especially since none of this was a planned event, and we all just kind of settled back, and relaxed together on the couch.

Michael asked to use the bathroom, and Louise directed him to the downstairs bathroom. While he was gone, I asked Louise if she thought that she should have done just what she did. She felt that he was a good young man, and that he was in a difficult situation, and that he just needed someone to take care of him. I told her that I thought that I was going to have to go home, and that I thought that Michael should leave before I go home. She wasn’t sure that she was done with him at this point, and that she felt that other than fucking her, she didn’t believe that he was any kind of a physical threat.

When Michael returned, everyone was dressed, and I excused myself, and Michael and Louise were left on the couch discussing the situation. She indicated that she would be willing to assist Michael with his problem, as long as he wasn’t hiding outside of her window and scaring the shit out of her. Being a young man, Michael was agreeable to the agreement, and asked for another blow job before he had to go home. Louise agreed and proceeded to suck him off again. He then went home for the evening.

Louise called me on my cell phone as I was on my way home, and thanked me for my help, and told me that Michael had just left, and that they were on good terms. I told her that it was an exciting evening to say the least, and that I would always be willing to help my sister in law at any time. I also told her that we could probably expect to see more of Michael, and that I should be there when he returns.

Louise indicated that she was still cum drenched, and that she needed to go get a shower, and get to bed so that she was ready for work for tomorrow. I asked her if she needed me to call her for phone sex at work the next day, and she said that she would probably not need the phone sex for a couple of days.



End of Story