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Training The Neighbor Boy

As a matter of choice we have avoided sharing with young people. Perhaps it is my age or that I have grown children and have a problem with the idea of screwing a man younger than my sons. Silly me. I have to admit that I have been with 3 very young men; a 21 year old and two 18 year olds. The one boy was a matter of circumstance as we dated a couple early in our experience in the lifestyle and didn’t quite recognize how young he was. She was in her early 40’s and he was only 21! Unfortunately, after sucking on him just a little bit and as I got on the edge of the bed and opened my legs for him, he released on my thighs. I tried to get him inside so at least he could feel my warmth while he came, but it was too late and that basically ended the date for me. The other two boys were suggestions by my husband. One was the lawn boy; the other was a waiter at a local Mexican restaurant. I wasn’t really that interested but eventually when opportunities presented themselves, I did it with them. I was horny and thought it would be fun. I simply invited the lawn boy in for cold water and seduced him. And I had the waiter deliver food at the end of his shift. He was anxious about that and I had known for a long time that I was his older woman fantasy. The lawn boy wanted intercourse right when we got in bed and managed to just get his stiff purple teenage dick inside me before I felt the wet rush and cream running down my ass. He jerked and whimpered and couldn’t wait to get his pants back on and get out of there. The waiter was a bit more suave. We kissed and played 69. He had a beautiful young hard body and big hard cock. When I sucked him I could feel the blood pumping into the head and when I tasted his pre-cum I stopped and told him to fuck me. The poor boy pumped me for 15-20 seconds and that was it. He pulled it out to make his release and I managed to get my mouth around it before he finished his spasms. He was a little more romantic afterwards and was already asking when we could do it again. Now I don’t want to seem selfish but I do enjoy a good fucking and when a man can forcefully penetrate me. I do believe in the idea that it is all about feeling good and it did feel good to satisfy them and give them pleasure and cunt their hard teen cocks. But that was it until recently and that is what this story is meant to be about.

There is this boy that lives in our condo complex. I have seen him many times walking about and sometimes with a couple young girls. Very cute to watch and in a group they play the typical teenage games and flirt by socking each other and doing sophomoric things to get attention. My husband has hit tennis balls with him and we have talked with him at the pool. He had even been in our house for soda while my husband searched for an old wooden racquet to show him.

My first private experience with him was on a very strange day and again circumstances brought about my desire to sex him. I had gone to work wearing something slightly provocative because I was having a meeting in town with a customer and the last time I was at their office I noticed the men were very interested and flirting with me. My husband and I have given each other a hall pass to use anytime we would find it interesting and satisfying to share romance and adventurous sex. So, I thought that I would respond this time and see what might happen. I wore a short skirt, hose, high heels and animal print panties. I particularly like the skirt because I can cause it to ride up by just shifting my legs and ass in a chair. It has become my lucky skirt and the last time I had worn it to work I got laid at lunch on Valentine’s Day (I’ll tell that story later.) Anyway I spent the morning at my desk thinking about the possibilities and left to make my meeting at 11AM. I secretly thought that maybe I could get a handsome guy to take me to lunch and we could fool around. The meeting didn’t go as I planned and I was stuck in a boardroom with 4 other women and two men. I didn’t feel comfortable letting these women look up my skirt. After returning to my office I was wickedly horny and wet. I rubbed my pussy at my desk and thought that I would go to the bathroom and masturbate to relieve the tension. When I went to the bathroom there were too many eyes and ears and really wanted to let go and have a big O. I knew there was possibility that I couldn’t control myself and my orgasm. So I just peed and dried my wet pussy and went back to work with the idea that I’d masturbate when I got home or try and wait until my husband came home and could fuck the horny out of me. It was a long afternoon. When I got home I made a drink, got my new little toy and grabbed the camera. My idea was to go out on the patio, relax, and get off. The patio is not completely private to curious neighbors but private enough to have a few orgasms in a chair if I didn’t scream or moan too loud. My husband bought me this great little vibrator. It is the size and shape of a 1 inch pencil. It has a long wire that goes to the batteries and wow it vibrates! It vibrates more powerfully than my Hitachi plugged into a wall outlet. It is easy to hide and fits alongside my clit in my panties. I just put it next to my clit, pull up my pantyhose and it stays. I like it because I have no control over my orgasm. I just turn it on and in a few minutes I’m letting go. It fits well in other places too and I have used it several times in the car and in public while my husband watches me try and control myself. Anyway I sat in my chair and began to think about my sexual feelings and rubbed my pussy through my clothing. I thought I would have a nice wet orgasm and take a couple pictures of my swollen cunt to show my husband what I had done and ask him to fuck me when he came home.

Then I saw him. That boy was walking towards my direction through the parking lot. I don’t know what I was thinking but it just came out of me. I waved at him and asked him if he knew anything about IPads. I told him that I was trying to make it work with Facebook and needed help. He was eager to help and I met him at the door. I brought him to the patio and sat down with my IPad and asked him to show me how the Facebook App worked. When he was done I told him to have a seat. The other chair was across the small patio and facing mine. I continued to fidget with the IPad and made small talk with him. I asked him about his school and how old he was and if he still played tennis; just friendly innocent chat. I let my skirt ride up and exposed my panty covered pussy to him. I didn’t look at him at all. I knew that he wanted to look up my skirt and so I avoided eye contact. I told him that I had seen him walking with his girlfriend. He responded that she was just a friend. I was like oh really…and asked him if he had a girlfriend. He said that he used to have one. I told him he was a cute boy and that there must be a lot of girls at college that he could date. I asked him if boys even have steady girlfriends anymore or if they just have girls for sex. He was nervous and before he said anything I told him to be careful and don’t get any girls pregnant and to use condoms. He was like of course I use them but only had had sex a couple times. I told him that there will be plenty of time and opportunities for that. I still hadn’t looked him in the eye but could see that he had an erection through his sports shorts. He was turned on by our talk and probably had been looking up my skirt. I was struggling for a way to get to the point. I mean if he was a mature man I would have just asked if he liked looking up my skirt and if he wanted to help me take it off. This was scary territory for me and him.
Before the silence killed everything I just told him that if he ever wanted to talk or know anything about girls that he could come to me. I told him that it is awkward at first but after some practice he’ll know how to make a girl feel good. I think he was mortified and thought he was going to excuse himself. But he hung in there. I quickly told him that the feeling he had when he came was the same for a woman if you do it right and once a girl has that feeling you’ll be doing it a lot with her! I laughed and tried to ease the seriousness of where I was headed. He admitted that he had never actually been in a girl or made one orgasm. He said he’s played with girls and the two times he had sex was once with her hand and the other time with her mouth. I was thinking how cute is that and OMG I can’t fuck this boy.

Now my mind was racing. But I decided it was actually a good thing. My husband has often mentioned and told the story about how he hadn’t been laid until he was 21 and it was the next door neighbor wife that seduced him, fucked him, and taught him a lot about sex. It is a very sweet story. So I told my boy toy that when I was young the hardest thing was finding a private place to do it. He agreed and volunteered that he and his girlfriend snuck into the rec room at the pool and she quickly give him a hand job and once a blow job. I told him that it was terrible and that he needed to find a safe place to experiment and make love. I now looked at him and asked him if he wanted to see how a woman has an orgasm. He was shocked and flabbergasted at best but all he could think to say was YES. I showed him my little vibrator and told him how most women orgasm from having their clits stimulated and some orgasm from penetration. I told him I can cum both ways but when I masturbate I just use my hand or a vibrator on my clit. I told him that when he masturbates he strokes himself and girls stroke their clits to have that feeling. I told him to come to me and I showed him the vibrator and let him feel it vibrating. I slid down in my chair and pulled down my pantyhose and panties and showed him my clit and told him where to put the vibrator. I helped him get it in the spot and pulled my stockings back up and sat in the chair. I probably should have just taken him into the bedroom at this point but I just wasn’t sure how far I was willing to take him.
I turned the vibrator on and sat back. He watched intensely as I had little spasms and my legs shifted and tensed. I softly moaned and told him it would take a few minutes. I picked up the camera and asked him to take it.
I told him he could take some pictures. I told him they were for him but he had to come over to see them. He took a few pictures and I was breathing hard and moaning. I knew my orgasm was close and I crossed my legs. I didn’t want to shock him in case I peed my panties and flooded the chair. When it started I grabbed the arms of the chair and threw my head back. My body shook and my toes curled up inside my heels. The spasms shot through me and I whispered that I was cumming. He was silent and watched in amazement.

As my spasms subsided I turned off and removed the little vibrator. A collapsed in the chair and looked at him over my nose and under my reading glasses. Panting like a dog I told him to come to me. He stood up and approached. I told him to come closer and directed him to stand between me and the door so no one could see what I was about to do. I put my hand on his shorts and outlined his cock with my fingers. I asked him if he liked it. I told him that if he wanted I would teach him about sex. I told him that he could come over and that I would show him everything and make him feel good. I told him not to be shy and that we could do anything he wanted. His cock was hard and I slipped my hand up the leg of his shorts and grabbed it bare. He was an excited young man and the head of his cock was creamy and slick. I told him that we could go to the bedroom and he could put it in me if he wanted. I unzipped his pants and pulled it out. He had a beautiful cock. It was so clean and throbbing. There was a steady stream of fluid oozing from it. I pulled it to my mouth and put my tongue on it to taste him and then kissed and lightly sucked the tip. As I was about to take him by the hand to the bedroom he jerked away and began his ejaculation. He must have been afraid about what I would think if he let go in my mouth. His cream shot out on my face, my sweater, my skirt, my legs, and shoes. He tried to retreat. It was thick and kept squirting while I pulled on it to get it to my mouth. I held his ass and pulled him towards me while I sucked and swallowed. When it stopped I quickly let go to look around and see if anyone had noticed from afar. We were safe. His legs were buckling and I took him into the bedroom. I could tell he felt that he needed to leave but I calmed him and got him to the bed where I talked to him and assured him it was okay. I sucked him some more and explained that I wanted to be his teacher. He wanted the same and we agreed on when he could come by and I showed him where I’d keep the photos for him to look at whenever he wanted.

I told him that he didn’t have to leave and he said that he could stay for just a little while. I stroked his body and whispered naughty things in his ear and told him that I wanted to show him something. I pulled off my clothes and lay with my legs open so he could touch and see my pussy. I told him it was okay to touch it and play with it. After putting his finger inside it I had that need to get off again. I had cum but still needed to have something inside me. I began to rub my clit and told him to use his fingers to fuck me. I told him that when I was going to cum I’d tell him and he could stop and feel my contractions on his fingers. I rubbed and he played and watched. My body was responding and my breath grew deep. I then noticed that he was hard again. I had forgotten that these young boys can recover! I stopped in time and told him to lay back flat on the bed. I asked him genuinely if he wanted to put it inside me. He did and I told him not to move. I told him that I would do everything for him. I straddled over him and guided the tip to my pussy. I let him watch all of it. I let him watch as I sat on it as it slid easily and completely into me. I was wet and I moved slowly as my pussy sucked against his cock. I stopped fully on him and told him not to move. I went back to rubbing my clit. He watched as I could feel him throbbing inside. He said it felt good and I told him that it was okay to have an orgasm and release in me. As I approached mine I told him that I was going to cum. I screamed and my pussy clamped down in its first contraction. My spasms started and I couldn’t help but ride up and down to feel him penetrate me and slide out. This was too much for him to handle and he tried to respond by thrusting in me but I pressed down on his chest and thighs and stroked him with my cumming cunt. He exploded and jerked. What was left inside him was now inside me. I let him finish his spasms and got off him. He was a happy boy! I was a happy girl!

Since then, and he was a little shy at first, he has come to his teacher 6 times. He now knows how to properly eat my pussy and can give me a good fucking after his first orgasm. We are still working on that one. I’ve even tried putting condoms on him but when he gets between my legs it isn’t long before he has his ejaculation. So I let him get off and on the second try he has the stamina to let me cum first. I really don’t mind and it is very erotic to take sloppy seconds from the same man. I hope when he finds a hot girlfriend that she has a good supply of sheets! Between me getting off and his big loads we make some huge sex milk shakes together.

I’ll try and post some of the pictures he took in the public gallery and his cums in my personal gallery.

End of Story