It all started when I invited my friend, Gina, out for drinks with the people who worked in my office. She was much younger than me, in her mid-thirties, and she was a very fun-loving woman. I loved to spend time with her and we often went out for dinner and drinks. My wife did not mind, since she knew I was not having an affair with her, even though Gina and I talked freely about everything, including sex.
At the bar, Gina and one of the young guys in our office really hit it off. John was quite handsome: tall, muscular and confident. Gina said afterwards that he was a “cutie” but maybe too aware of how good-looking he was. They talked together for quite a while and both were obviously very interested in each other. Aftewards, they ended up going to her place, but other than some drinks and dance, they just “made out” according to Gina.
She and I had some very honest conversations together, especially about sex. I told her how good Jean still looked and then sent her a nude picture to prove it. She was very impressed and so I sent her more, since she seemed to like them so much. I joked with Gina that I could come over and take some pics of her, or I could loan my camera to John. She thought this was amusing, but didn’t take me up on my offer. I didn’t expect her to.
Little did I know that Gina and John became lovers afterward. He was spending a lot of evenings at her place, and I’m sure she enjoyed his perfect body. She was very sensual and loved sex. I never made love to her but we talked about everything, and she told me about many of her experiences. Except I didn’t find out about John until much later….
One day, John approached me at the office and asked if he could talk to me privately. I said sure. After closing the door, he told me about his and Gina’s relationship and that she had also shared my wife’ pictures with him. He thought my wife was amazingly hot, especially for being over 50. I was shocked, but also a little intrigued, since I had always enjoyed showing her off. I had shared her nude pics with 3 other admirers in the past with Jean’s permission. I asked him for more detail on his opinions of my wife, and he was happy to oblige. He told me he loved her beautiful Italian body, with her large breasts and hips but with the tiny waist and thin, muscular legs. Jean works out many hours a week and keeps in top shape.
John said he really wanted to see her in person so that he could compare her to the pictures he’d seen. And he also said in so many words that he wanted even more than that. I told him I thought it would be difficult for me to get Jean to take her clothes off for him, let alone let him taste her sweet body. Although great in bed, she has resisted the idea of me sharing her unless it was with someone she really wanted. She is very picky and had rejected several opportunities that I presented her. The thought of this young guy stripping her clothes off and putting his dick in her mouth and slipping it into her pussy was making me hard, however.
John then used the argument that he and I could convince her that she had to cooperate; otherwise he could share Jean’s pics with others at work and make problems for me if she didn’t go along. I could see he was saying this in a way to make it appear we were on the same page and just coming up with a strategy to get Jean to go along, but the unstated threat was also there. I had mixed emotions about this: on the one hand, I would love to see my sweet innocent wife spread her legs for a young, handsome guy who probably had a big dick (my suspicions were later confirmed). On the other hand, we would be getting in deeper with John and the work situation was certainly problematic.
We went out for drinks that night to discuss it further. John became pretty persuasive in his arguments and I could not see another way around this. He said he would be at my house next Saturday night and that I had that much time to work things out with Jean. Since he worked for me, he had always been very respectful, even though I could tell there was a strong personality there. He probably knew that he was attractive to women, and this gave him the confidence to proceed as he had with Gina first…. and now with Jean.
I finally told the whole story to Jean. She was of course at first shocked and then very angry, and justifiably blamed me for causing this situation by sharing her pictures. We talked about it over the next few days, and although still mad, our relationship is strong and it could stand the strain of even this unusual situation.
As we talked about it, I explained that John loved her pictures and he thought she was extremely hot. I could see her thinking about this and it was obvious that, like almost all women, she began to like the fact that he lusted after her, despite her being much older.
She had met John at the office and admitted to me that he was handsome and even that he appeared to have a great body. She did not use the term “cutie” that Gina used, but it was obvious that she thought he was sexy. She wasn’t usually taken with younger guys, preferring guys close to my age when I could get her to talk about it. She did seem to be less angry and more thoughtful as the week went on. She then finally, reluctantly agreed to do whatever John wanted, within reason. I tried to say in my clumsy way that she might even enjoy making love to John. She at first reacted angrily and would not admit this, but did go so far as to say he was good-looking and it “wouldn’t be terrible.” When I asked her if she thought he was sexy, she only replied softly: “I guess…”
The big day finally came and she was fussing about what to wear, or not wear. I suggested a sexy little nightie that she had worn for some of my pictures. She approved of this since it was sexy and yet covered her breasts and pussy behind a thin material, but allowed her to be accessible. Her mood seemed to vary between being nervous to thoughtful resignation.
John showed up on time and was very friendly, yet confident. We talked for a few minutes and when Jean finally descended the stairs in her sexy nighty, he said: “Wow, you look so beautiful.”. She shyly and nervously smiled at him but seemed to appreciate the compliment. She was in her bare feet, which were so sexy and small, and her well-formed legs were well displayed. The thin material of her covering showed her nipples underneath and as she moved, you could see the dark outline of her pubic hair.
As she approached him, he gently took her in her arms and hugged her, then kissed her on the cheek. I noticed his hands lingering on her ass, pulling her to him. Since it was only lightly covered by thin cloth, I’m sure he got a good feel. She was about a foot smaller than he was, and he really towered over her petite frame. They then sat down on the coach together, and I sat across from them.
John then mentioned the pictures and how fantastic she looked in them. He said he wondered if she looked as good in real life and said that now he knew it was true. Jean looked embarrassed but again took the compliment well. After a few minutes of small talk, he moved closer to her on the couch and put his arm behind her head and touched her on the thigh with the other hand. She stiffened for a second, but then slowly relaxed. He then moved in for a kiss, which she did not resist. In fact, she returned it without reservation but without evident passion, as if she was doing her job effectively. She quickly looked over at me after the kiss to make sure, I think, that I was OK and wanted her to proceed. I smiled in probably a lustful way and she then looked back at John, satisfied that everything was OK. His one hand moved to caress her breasts as he leaned in to kiss her again, this time more passionately. She seemed more relaxed now and responded accordingly.
He then placed his hand on her legs and slowly moved up her thighs, finally reaching her pussy. She slowly moved her legs apart to allow him to reach his target. She was breathing more heavily now, still seemingly somewhat embarrassed by the look on her face. Jean told me later that she was surprised that she could respond to him after just a few minutes — she thought it would be much harder. She let out a small “ugh” sound as he put his finger into her. He kissed her as he continued to finger her. I could tell she was opening her mouth more to allow his tongue access to hers.
He told her to unzip his shorts. She hesitated and then nervously moved her hands to his lap and pulled down the zipper and then unbuckled his pants, looking up at him slightly embarrassed as she did so. “Take out my dick” he said softly but commandingly. He wasn’t wearing underwear but she had to struggle slightly to get him out because he was already half hard, and appeared pretty large. He helped her by pulling down his shorts. Her mouth was open and she was breathing harder. He pulled her breasts free from the top of her nighty and lightly caressed her nipples, which were now hard. I heard a sharp intake of her breath as he did this.
“Oh my God” she said, as she held his penis with both of her hands, gently and softly caressing it. I assume her comment was both a reflection of his size and the situation she found herself in, caressing another guy’s dick for the first time in many years. “I can’t believe I’m doing this,” she then added.
He smiled condescendingly at both her and then also me, as he repositioned himself slightly. John then slowly and gently put one hand behind her head and moved it towards his crotch, pushing her hair behind her ear, maybe so I could see. She bent over him without resistance and moved her lips towards his cock. Jean hesitated slightly before she put her lips on his cockhead, and kissed it. She then took the head into her mouth. He was growing under her attention and his cock was very big; much bigger than mine. His shaft was now elongated and seemed huge. I don’t know how big it was but it must have been 8-9 inches, and quite thick. She held it with one hand and swirled her tongue around the head, as this was as much as she seemed able to do with his size initially. She found she had to get used to the different size of his penis.
He and I had briefly discussed what would happen, and I told him I wanted to see her give him a blowjob and come in her mouth. He was happy to oblige, he said, and seemed to like the power he had over her and me.
Jean’s oral skills were excellent and I had always told her that it was unfortunate that I had been the only one to benefit from them. I couldn’t believe how sexy she looked now, trying to accommodate this large member in her mouth. She seemed to be getting more comfortable with the situation, and had settled into a routine of putting a few inches into her mouth while she swirled her tongue around the sensitive underside and alternately kissing it. She then slipped off the couch and kneeled in front him without breaking her stride. I think the other position was not comfortable for her. I got up and moved to another position so I could see the action.
John moaned appreciatively as she ministered to his cock. “That feels unbelievable!” he said several times, and caressed her hair and her head. She was getting more aggressive now with her actions, wanting to make him come, I think. He didn’t have any problem doing this in front of me, and almost seemed to enjoy showing off his large dick.
Finally at one point, he pulled her nightie off of her so that she was completely naked kneeling in front of him. Her head continued to bob up and down and I could hear her sloppy sucking and licking sounds, any evidence of her shyness now completely gone.
After a few more minutes of this, he was breathing heavily too and told her: “Swallow my come!” She looked up at him briefly in surprise and prepared her mouth to receive his semen. With a groan, he unloaded into her mouth. Jean had trouble with the size of him in her mouth, combined with the large quantity of juice that he had unloaded into her, but she did her best to swallow as much as possible. She was making a slight choking sound as she swallowed it. I couldn’t believe the sight of his come pouring out of her mouth, slowly trickling down his shaft. I was shaking with excitement.
“Oh my God, that was fantastic!” he said as he finished coming in her mouth. As she finished swallowing, she slowly raised her head and smiled up at his compliment. “I can’t believe how big you are!” she said as she finished and raised her head.
“Lick up all of my come” he commanded and she at first hesitated, but then bent down and licked his penis up and down to clean him. This was frankly more than I expected of her. She didn’t seem to mind that she was now completely subservient to his sexual wants. Actually, she seemed to enjoy servicing a young handsome guy and make him come.
John then pulled her up next to him and she looked back at him in a submissive way, slightly smiling. “You’re amazing!” he said as he caressed her large breasts and her thighs. She again seemed to appreciate the compliments from this good-looking young guy, not realizing I guess that all the things I had told her about her abilities were true. She looked over at me shyly again, reassured that I had also enjoyed it. What I especially loved was that my sweet, demure wife had shown me that she could be so sexy with another guy.
He again started to finger her and caress her breasts, kissing her from time to time. I could tell she didn’t know whether this was it or if there was more to come. “She is very wet now”, he said as he continued to caress her pussy lips. She blushed in embarrassment at this, and looked over at me shyly. John’s flaccid penis still looked very large laying there in his lap. After a few minutes of playing with her, he started to get hard again. She noticed this and couldn’t help staring down at it from time to time — checking his progress I guess.
Next he stood up, and pulled her up with him, hugging her to his body. He smashed her breasts against his muscular chest, and kneaded her ass cheeks. She looked so vulnerable– her petite body against his muscular frame. She looked up at him as if she were completely in his control now. Being naked and having just performed the most intimate act with him made her seem very submissive by this time. She told me later that she felt as if she was now willing and able to do anything for him, since there was nothing left to hide or hold back. For such a young guy, he seemed in complete control. She didn’t think a young guy could make her feel this way.
“Now I want to make love to you” he said. He kept telling her he couldn’t believe how good her body looked. She seemed to accept the situation and shyly said to him: “Come up to my bed, then.” He picked her tiny body up in his strong arms and carried her up the stairs. I was left there staring up at them as they ascended.
I quietly followed them. He gently laid her down on the bed, and then crawled next to her. His hands caressed her legs and her breasts. He spent some time sucking on those beautiful tits of hers. It’s not her favorite thing, but she seemed to enjoy the attention. She was smiling in a dreamy kind of way.
She then gently stroked him, looking down on his large penis with a kind of awe. I know she had never seen anything like it before. She told me later she was thinking about whether it would fit in her petite body or not, and what it would feel like.
John seemed very experienced for being a guy in his late 20’s. Certainly he knew how to make her willing to do almost anything by that time. She said: “Do you want me to suck you some more?” He of course said yes. She moved on her stomach in reverse position to him and started caressing his dick with her mouth. She was splayed out with her beautiful ass exposed, swelling above her thin waist. He took advantage of this by working his fingers into her and spreading her ass cheeks as she sucked him. The view was amazing of her beautiful ass, legs and little feet. She still found it somewhat difficult to get much of him into her mouth because of his size.
From time to time, she would move down to his balls and smell him. She had always loved the musty smell of a man’s balls, and she said he smelled great. This really turns her on, and she even moaned in appreciation of his large balls that she caressed with her nose.
Finally he moved her into position so he could go down on her. She was very wet by now, and he was licking up her leaking moisture with his tongue. She moaned softly; she was never a screamer but you could tell she was enjoying this.
After a few minutes of this, he moved her onto her back and positioned himself above her. She looked so small and vulnerable under him. Her legs bent and it was incredible to see his large cock moving towards the goal of her pussy, slowly getting closer and closer. I wondered if she would be able to take him. She said later that she was a little apprehensive, but was excited enough not to let it worry her too much!
He was slow and gentle with her. She moaned as he slowly pushed his big dick into her opening, wiggling his ass from time to time to fit more and more of it inside of her. A couple of times she moaned: “Oh my God, you are so big!” or “Wait, go slow!” Later, she admitted to me that the feeling of being completely filled was so different that it made her feel so sexy.
After he got all the way in and started to pump her with long, sensuous strokes for a few minutes, she came for the first time, and let out a loud wailing groan, the likes of which I hadn’t heard in a long time. Her muscular legs grabbed the side of his but and held him there and her toes curled. Her legs pumped a few times as her orgasm overcame her. She was breathing heavily and moaning as she slowly came down from it.
I could tell John enjoyed being able to make her come like this after just a few minutes. He seemed triumphant in his conquest of her, a much older woman who was now his plaything. He moved faster and faster in his pumping and started to moan himself. I’m sure the friction her petite little body provided to his stroking penis was an incredible feeling.
He grabbed her ass for leverage and was really forcing his penis into her now. She again started to moan softly, with another orgasm starting to swell. They then changed positions, with her on top. Seeing her splayed on top of him and seeing his long, thick shaft disappearing into her pussy with each stroke was unbelievable. Her beautiful ass above the junction of their two bodies, her muscular legs bent beside his was incredible. I could see much more of the action this way and couldn’t believe how hot they looked together. Her eyes were closed as she moved her hips and ass to provide the friction she wanted. Seeing her ass spread like this from behind and his dick sliding up and down was one of the sexiest things I’d ever seen.
She came again with a crescendo of her rising moans. She almost couldn’t keep her balance on top of him as she came. He smiled up at her and her evident passion, realizing that he was able to reduce this mature, beautiful, sophisticated woman to a mass of quivering emotion. She collapsed on top of him and moaned: “You are incredible!”
After a few minutes of rest, they resumed the missionary position and she continued to enjoy their love-making, lying under his muscular body as he pummeled her with his big dick. I could see the urgency in his strokes as he got closer and closer to coming. Finally he let out a long moan as he unloaded into her petite little body. He seemed to come for quite some time, and Jean was responding to his passion as he came in her. She later said that she could feel his cum shooting into her very obviously, since there was so little room in there. She loved that feeling. They then passionately kissed for a few minutes as their breathing returned to normal.
They lay together, naked on top of the sheets. She seemed very comfortable with John now, having shared her body with him and done the most intimate things with him for the past hour. She was cradled in his arms and his cock was again flaccid, although still large. She was caressing it with her hand, as if it were a prized possession. John said it was time for him to go, and as he got up to go, he kissed her deeply and she responded.
I took off my clothes as John left and got into bed with her. I kissed her and could taste the come on her breath. I asked her how it had been and she said, smilingly, “Actually, it was wonderful!” I asked her if she was mad at me and she said, “No, not anymore.”
I talked to her later that night about how it felt. She said that after she got over her initial nervousness, she loved making love to him. She said: “He has a great body and his cock felt so good inside of me. It felt very different because of his size. “
Because of his size and the size of his cock, she felt she was totally in his control and was a little afraid at first. She didn’t know if she could take him, but he was very gentle. Being wet helped a lot, of course. He filled her up completely. She said “He seemed to enjoy the power he had over me and the ability to make me come like that.”
I slowly entered her and she was soaking wet. I could hardly feel her but it felt so silky smooth. She responded to my lovemaking and unfortunately I did not last long. I added my come to his and she was overflowing. I couldn’t believe how much come there was leaking out of her now.
John continues to come over once a month or so and strip my wife in the living room before carrying her up to our bedroom. She enjoys being naked for him and sucking and fucking him in our bed. She is totally subservient to his needs and loves being dominated by him. There are no complaints from her. In fact, she greatly enjoys their lovemaking sessions, and the attention this young handsome guy gives her.
John has told me he loves having both Jean and Gina to satisfy him. One younger woman and one older that both appreciate his body and skills, not to mention his large cock. I’ve suggested that Jean consider doing this with others, but she insists she is completely satisfied with the two of us. So far, it has worked out great for us.