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It was wonderful to see how my wife Jan began to help my friend Phil overcome both his initial shyness and then later his impetuousness and perhaps roughness in his sexual advances towards her. For example at the start he would tend to be quite rough in groping her breasts, whereas after a while Jan would get him to stand behind her and show him how to treat them with respect, firm but lovingly stroking them; she would take his hands and show him how he liked her nipples touched in order to make them erect without getting sore. When he got it right Jan would respond by stimulating a sexual area of his body, or take his erect penis in her mouth or lick the glans or his balls, or she would pull him into her body and give him the most intimate kiss. Of course it pleased her to be able to educate him like this as it was very fulfilling for her; likewise she knew that in the times when I was present I would be personally aroused, and would sometimes, but not always, join in. Jan is no slut — she understands what a loving relationship is, even when it is two men instead of one. She always made sure that when we were alone she would reassure me of her love for me, something I needed to hear, and checked that I was still happy for the second relationship to continue.
However gradually as Phil became more confident in his sexual prowess he secretly began to make more meaningful relationships with girls of his age and it became clear in time that he was slowly weaning himself off my wife in order to pursue a relationship with one particular single woman. Of course Jan was very happy that she had played such a positive part in helping him to a more mature way of life with women, but naturally sad that he was not so much a part of her life. When, one day, he announced that he wanted to adopt a steady relationship with this woman and that he felt it would be wrong to continue a similar one with Jan there were many tears from her. For one last time Phil took Jan in his arms, kissing her passionately, then slowly and lovingly undid the buttons on her blouse and skirt, under which he knew there would be no other protection for her body, scooped her up in his arms and carried her to the bedroom for last rites. I knew I would not be welcome in the room that night. As I listened from the next room during the next few hours I could hear the pants and sighs as Phil thrust his full penis between her so-willing thighs for the last time and emptied that cock of all its remaining love for her, my wife echoing his moans with cries of love and despair together.
In the morning Phil had gone and although we saw him again from time to time we knew that the relationship as it was had ended. It took many months to help Jan recover to a good place again, during which often she seemed drained of all sexual energy. I had some idea of what she was feeling and tried to be patient with her. Gradually we re-established our own relationship to the pace where we both were enjoying one another with abandon again. We concluded that something like this was never likely to happen again and settled down to a satisfactory, if at times unexciting, sexual life together.
Two years ago something happened to me that was to be a pivotal moment in Jan’s and my relationship. I developed something called Peyronie’s Disease. Fortunately it is not very common and I had never heard of it at all. My wife noticed it first, surprisingly. A small bend in my erect penis, nothing to worry about I thought, but Jan wanted me to see a doctor about it. In the meantime, looking on the web I discovered Peyronie’s and my doctor suggested it as likely. He sent me to a specialist who confirmed that I had indeed contracted the disease (not infectious) and that there was neither any definite known cause nor a cure, other than surgery once the bend, which was increasing every day, had settled down. Even then there was no certainty of success. It is difficult to imagine a bend in your trusty erect penis approaching 90 degrees but that is what developed, making intercourse too painful for both of us. Of course we found ways around it but had to avoid penetration. It was compounded by Jan one day telling me how, although she loved me, that she found it sexually a turn-off to see my deformed member.
We agreed that we loved each other enough to find a solution but the only one seemed to be to find Jan another partner like before who could fulfill her deep needs to be fully satisfied in that hollow between her legs. One day I asked her, in desperation really, if there was anyone she could envisage allowing into that space. She had evidently been thinking about it herself and she replied that the only one she could think of was Jeff. I must admit that I was shocked as Jeff, at 18, had only recently got married so I couldn’t imagine him being interested in my middle-aged (but beautiful) wife, so in my mind I dismissed it. This was also because although he was 18 Jeff, to me anyway, was still looking like the 15/16 year old that we used to see going to school until he managed to get his girlfriend pregnant. At least he had chosen to marry her. Anyway, as I say, I dismissed it from my mind completely until one day, when his computer stopped working, I said that I would try and fix it for him as that is one of the things I do. It was his laptop and he allowed me to take it away to check it out. As it happened it was not a difficult fault to fix but in the process I came across some of his tastes in internet sex. I was amazed to find loads and loads, not just a few, of video’s of sex with mature women. At first I thought it was part of a job lot but after a while I could see that this guy really did enjoy these video’s. I decided to invite him round while my wife was out for the day to explain how I fixed his laptop and to investigate his tastes further.
On the Saturday he came round to our house and we had a few beers together while watching the football. When he was relaxed I produced his laptop and casually mentioned these video’s that I’d spotted. At this point he went bright red, apologized profusely, and almost begged me not to mention it to his new wife. I assured him that I had no intention of doing that and he began to calm down a bit. In fact, I said, I had a video of my wife undressing and wondered if he was interested in seeing it. Of course he was. As I played it to him I could see the bulge in his shorts as my wife slowly took off her bra to reveal her full breasts, dropped her pants and parted her legs to show all her glory. I asked him what he normally did when he viewed such clips and he told me he masturbated to them. When I told him that I did too he relaxed even more. Now I don’t know how you guys do it but I have had this habit since childhood of using a pillow to stimulate me; it is as much like a woman’s body as I can get without buying a blow-up, which I think my wife might have objected to. He was very interested to know how I did it, so we took my laptop up to the bedroom and we set her striptease on repeat in the middle at the head of the bed, armed ourselves with a pillow and tissues each, and took off all our clothes. I have to admit it felt a bit weird and I was glad my wife was definitely out all day. Jeff’s penis was well erect, long but quite narrow; his body was just young-looking and bore out my estimation of his age, despite his 18 years.
Slowly he followed me as I lay on top of the pillow, inserting my hard-on under the pillow-slip at the top and thrusting in and out to the view of my wife’s naked body and welcoming open thighs. I had warned him to be ready with the tissues when he felt himself about to cum so at that point we both covered our long erect shafts with a few of them. He really did not last long, and who can blame him, but he did make a lot of noise as his young tool shot out explosions of creamy cum. I found it more difficult as I was familiar with the clip but the sound of his moans expressed at the enjoyment of my wife’s body was soon enough to send my own cock into spasms of joy.
At this point I resolved to get him and my wife together. It would be more difficult because Jeff had a wife who would expect him to be around at times. The first thing I did was to explain what I had discovered to Jan. I think that because of my inability to satisfy her completely she was ready for anything but she actually laughed when I described how I had got him to cum into a pillow at the sight of her lovely body. However she said she would do it whenever I was ready and had persuaded Jeff to try it out. As it happened there was soon an occasion when Jeff’s wife had to go away for a week on a course so I took the opportunity to invite him to dinner rather than live on burgers for a week. I suggested it would be nice to dress up for the occasion, with candles, red wine and that sort of thing. I had primed Jan to wear one of her more sexy outfits but even I was not prepared for what she was wearing as she came down the stairs after I had let Jeff in. She was wearing a short mini-dress with an opening that ran from top to waist level leaving little of her breasts to be imagined. Whenever she stooped or leant to one side it was clear that she was going to seduce at least one guy in that room as the sight of a nipple or two came into view.
With several glasses of wine consumed we were definitely a merry crew. When the slow romantic music was turned on it was obvious that so was Jeff! Jan would take us as partners in turn and I could see Jeff getting more and more steamy for her. I went to the kitchen to get the coffee and when I returned Jan was snogging this young boy, as I saw him, their tongues darting in and out of one another’s mouths, his right hand inside her dress feeling the shape of her breasts. I stood, slightly concealed, to watch as he stooped and opening her dress up began to kiss around her breasts and tongued her nipples to erection. My own penis began its journey to hardness, at first a bit uncomfortable because of the bend — I have got used to freeing it when I get horny in my wife’s presence so as to not to suffer so much discomfort so I darted upstairs and changed into my dressing gown.
When I returned it was clear that Jeff didn’t know much about what he was doing as he was largely oblivious of me. All he knew was that this sexy older woman had tipped his sexuality over the boundary of safety into new territories that he was about to discover. Having said that I have to give him his due that, despite a slur, he managed to ask me if it was OK to have her. But without waiting for an answer he dropped back my wife’s dress from off her shoulders, then to the ground and laid her down on the sofa with her whole nakedness revealed. Jan, who had retained a modicum of decorum, asked me if I would mind leaving the room as it was his first time with her; I reluctantly agreed. However I could still hear all that they were saying from the dining room where I sat drinking a full pot of coffee.
We had agreed previously that she would be free to express her lust for him so I was not surprised to hear her exclaim that he had a lovely body when he had clearly just removed all his own clothes. He must have quickly slipped his slender young cock between her legs and thrust it into her as I heard her gasp that it felt wonderful to have his long, straight cock right up inside her. You might think that I would have been jealous to hear that but instead I was overjoyed that at last my wife could be fully satisfied again as she felt this young boy’s manhood invading her for the first time. I heard her groan “Fuck me, Jeff, fuck me” several times, an indication that she was now passionately aroused by his youthful body clasped to her own. I imagined how it must have felt for his developing chest to lie on my wife’s full breasts, his lips and hers locked in tender and loving kisses, their tongues meeting and finding out the inside of one another’s hot mouths. I could hear him telling her how beautiful she was; she, likewise, was expressing her lust for his younger frame and I waited longingly for those moments when both of them would approach orgasm, the moans and groans increasing to a crescendo of passion until all Jeff’s hot cream and Jan’s love-juices exploded together as his slender young cock released its contents deep into my wife’s welcoming body.
I knew that they would lie together for some time locked in each other’s arms and I chose to go to the spare room to sleep so that they could enjoy the rest of the night together should they still have the energy and passion to continue to explore one another’s willing bodies. All through the night I could hear that their passions were being re-awakened as time after time he was driving his hard shaft in and out of her love-hole again, fully satisfying Jan’s dormant lust for a man to fill her up with hard cock. There is such power in imagination and I lay fucking my pillow with my hard but bent shaft as his perfectly formed member repeatedly gave Jan the satisfaction she craved, on one occasion emptying my own contents into the pillow substitute as I heard them coming to a climax together once again. In the morning I brought them breakfast. It was lovely to serve them and see their still naked upper bodies next to each other after their night of discovered passion, the smile on Jan’s face again telling me that she was grateful that I’d afforded her the opportunity to have her sexuality fully explored again. I knew it would be the first of many such occasions.