My wife and I are in our mid-fifties and have been married for thirty years. I had started having fantasies of her with another guy about ten years ago, but she showed no interest and the right situation never presented itself. That all changed two summers ago.
I had mentioned her fucking another guy, but she had declined. One night while we were in bed, I mentioned my work colleague Doug, who was about ten years younger than us and a good-looking guy. He and Deb had always gotten along, and I know she thought he was cute. I mentioned to her that I wanted to invite Doug to come over one day and hang out and asked if she thought she could sleep with him. After some hesitation and excuses, I suggested we have him over for drinks, dinner, and pool and that it would totally be her decision. If she were comfortable go for it—if not, then nothing needed to happen. She reluctantly agreed to that.
I talked to Doug and told him what I wanted to do. He was eager to join in, but I told him that it would happen only if she wanted it to. He agreed, and we set a date for Saturday for him to come to the house. I suggested if it looked like she was good for it, I would propose a scenario where he could kiss her to start any playtime.
Doug came over that Saturday and Deb and he hit it off right away. She gave me a big hug and a kiss on the cheek and poured us all a drink. We had a couple of drinks, catching up on our lives, and then ate dinner with more drinks. After we were done, I suggested we all put on our suits and hop in the pool to relax a bit. Deb went back to change, and I asked her to put on something sexy - she rolled her eyes and shook her head as she went to change.
Doug and I went into the pool and were talking when Deb came out. Wow, did she surprise me. She had put on a tiny suit that just laid across her 36B tits and her nipples were prominently hard and displayed. Her bottoms were as revealing with her pussy lips evident thru the tight material. She stepped into the pool with us and jumped into the conversation like it was no big deal. Doug had a big smile on his face, as did I once the shock wore off.
We relaxed and talked, with more flirting and tension building as we drank. Several times Debbie put her hand on Doug's arm or shoulder to make a point and she would let it linger. She was feeling no pain, and I was hoping this was the time it would happen, deciding to try my scenario and see if it worked.
We had been talking about our teen years and I mentioned that I had been voted as having "best legs" during my senior year. They both laughed, and Deb rubbed her foot on my leg and told me I still had it. Doug jumped in and said, "well, I was voted best kisser when I was in school!" to which we both laughed and said that came in handy. It was now or never!
I took a step towards Deb and gave her a slow and deep kiss, which caught her by surprise, but she eagerly accepted. I stepped back and looked at Doug and told him, "Well let’s see which of us is the best kisser now!!!". He laughed and took a step towards Deb, who was a bit in shock but was not saying no.
He came up to her and grabbed her shoulders kiddingly and lowered his lips to hers. It looked like it would be a short peck, but then his lips lingered and I saw his tongue enter her mouth. They kissed for what felt like five minutes but was only a minute, and Deb pulled back to catch her breath. I asked her to tell us who the best kisser was, and after a pause, she said" wow, both were really good! I’m not sure I can pick a winner".
Doug then told her, “Well, let’s give you another chance!" and reached over to kiss her again. After a deep passionate kiss, she looked at me.
I smiled and said, "you know I better be the winner!" and kissed her a second time. I had a raging erection and know she felt it when I kissed her, which I guess told her I was ok with this.
She stepped back and told me “Well, Doug was pretty good!"
I gave him a high-five and Deb hugged him in congratulations. As she pulled away, she turned her head up for another kiss! They stood there kissing and Deb had her arms around his neck while his hands found her back and ass. They broke the kiss and she turned to me and said, " You sure you’re ok?" to which I shook my head yes!!