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Anything Goes
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Straight Male / 52
Holiday Wife Share
Hi, I’m Simon. Quick background. Married to Cazzy for 30 years, 2 adult kids. My best friend from school is John. John married Cazzy’s best friend, Jo. I dated Jo in our teens, and she introduced me to Cazzy, and I introduced her to John. Never had two couples been so close; we even holidayed together with and without the kids. Sadly, Jo passed six years ago in her mid-40s. John became a regular fixture at our house, especially when all his kids left home.
4 years ago, all 3 of us went on a Caribbean cruise, It was something we had never done, so there were no member berries about past holidays. On a formal night, Cazzy looked fantastic in her evening dress at the end of the night, sat in bar John teared up and said that he always loved it when Jo dressed up for the local Christmas balls. He laughed that whenever Jo wore a formal evening dress, he was always randy and would chase her around the bedroom as she dressed. He said he also missed having a sex life. After the usual platitudes about him meeting someone else, he said nobody could ever replace Jo; Cazzy got tearful at this comment.
Cazzy and I have over the years talked about wife-sharing and even included it in our sexual fantasies. She then drops a massive bombshell and tells John he could have sex with her, as it’s about time they evened the score up (I’d slept with Jo in our teens). Lots of talking then happened, I wasn’t sure, then John wasn’t sure, then all three of us thought it was a bad idea and then a great idea etc. We ended up back in our cabin.
That first time was a disappointment. Cazzy still in her black evening dress, takes her black knickers off and lies on the bed; John goes on top still wearing his dress shirt, trousers off. I caught one glimpse of his dick in my wife, otherwise, his shirt and her dress hid what was going on; the whole thing was over in five minutes. John then kissed Cazzy, said thanks to us both and returned to his cabin. I was amazed looking at my wife’s pussy and the cream pie. John and I had the snip together, and Cazzy was post-menopausal. I fucked her and loved every moment of it, for as disappointing as the actual wife share was, the sex afterwards was amazing. I had one of the biggest orgasms I can remember.
That night started the whole thing. The next day was a sea day; after relaxing by one of the pools and lunch, we went back to our cabin, and I watched John fuck my wife again. This time I saw it all, both nude and wow, nothing can prepare you for the sexual high of watching another man’s cock stretch your bride’s c**t open; man, that was fantastic. Cazzy and John pretty much fucked every day of the holiday. It was agreed though what happens on holiday stays on holiday.
The pandemic hit the following year, so in 2020 and 2021 we didn’t go anywhere, and the relationship with John returned to normal. In 2022 after the world re-opened, we went to St Lucia for two weeks. Nobody said anything; however, on the first night, I was getting ready for dinner and had just gotten out of the shower. I heard a knock on the door which I guessed would be John. As I left the bathroom, my bride’s maxi dress was up to her waist, with my best friend between her legs eating her pussy! I sat down and watched. He fucked her, I fucked her, and then I went again. In the end, we ordered room service. That became the norm on our holidays with John.
Regrets, no. The sharing has boosted our sex lives. Cazzy assured me that although she is very fond of John, she will always love me. I had slept with Jo; in fact, I was her first, so I suppose this did even things out. John turned a corner in the bereavement process, so everybody gained.
4 years ago, all 3 of us went on a Caribbean cruise, It was something we had never done, so there were no member berries about past holidays. On a formal night, Cazzy looked fantastic in her evening dress at the end of the night, sat in bar John teared up and said that he always loved it when Jo dressed up for the local Christmas balls. He laughed that whenever Jo wore a formal evening dress, he was always randy and would chase her around the bedroom as she dressed. He said he also missed having a sex life. After the usual platitudes about him meeting someone else, he said nobody could ever replace Jo; Cazzy got tearful at this comment.
Cazzy and I have over the years talked about wife-sharing and even included it in our sexual fantasies. She then drops a massive bombshell and tells John he could have sex with her, as it’s about time they evened the score up (I’d slept with Jo in our teens). Lots of talking then happened, I wasn’t sure, then John wasn’t sure, then all three of us thought it was a bad idea and then a great idea etc. We ended up back in our cabin.
That first time was a disappointment. Cazzy still in her black evening dress, takes her black knickers off and lies on the bed; John goes on top still wearing his dress shirt, trousers off. I caught one glimpse of his dick in my wife, otherwise, his shirt and her dress hid what was going on; the whole thing was over in five minutes. John then kissed Cazzy, said thanks to us both and returned to his cabin. I was amazed looking at my wife’s pussy and the cream pie. John and I had the snip together, and Cazzy was post-menopausal. I fucked her and loved every moment of it, for as disappointing as the actual wife share was, the sex afterwards was amazing. I had one of the biggest orgasms I can remember.
That night started the whole thing. The next day was a sea day; after relaxing by one of the pools and lunch, we went back to our cabin, and I watched John fuck my wife again. This time I saw it all, both nude and wow, nothing can prepare you for the sexual high of watching another man’s cock stretch your bride’s c**t open; man, that was fantastic. Cazzy and John pretty much fucked every day of the holiday. It was agreed though what happens on holiday stays on holiday.
The pandemic hit the following year, so in 2020 and 2021 we didn’t go anywhere, and the relationship with John returned to normal. In 2022 after the world re-opened, we went to St Lucia for two weeks. Nobody said anything; however, on the first night, I was getting ready for dinner and had just gotten out of the shower. I heard a knock on the door which I guessed would be John. As I left the bathroom, my bride’s maxi dress was up to her waist, with my best friend between her legs eating her pussy! I sat down and watched. He fucked her, I fucked her, and then I went again. In the end, we ordered room service. That became the norm on our holidays with John.
Regrets, no. The sharing has boosted our sex lives. Cazzy assured me that although she is very fond of John, she will always love me. I had slept with Jo; in fact, I was her first, so I suppose this did even things out. John turned a corner in the bereavement process, so everybody gained.
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