The oldest I had was 68 and I was in my early 40s when that happened, but years before that I had a 36 year old woman when I was still in HS. My first wife was a serial cheater that was getting other guys shaft when I was out of sight, it didn’t take me long to realize that. Me and her married young, and a couple of years after we married when she was 20, I ask her what was the oldest she ever had behind my back, and she told me that she thought he was 30. A few months later I took her out to someone’s van that I will just say was real close to me and screwed her after having coffee at a truck stop. Since I knew she had cheated on me more than a few times, I ask her while screwing her if she would do me a favor, and let the someone I was close to that was still inside the truck stop sitting at the booth fuck her. At first she looked réal surprised, then said to me, I guess if he or you don’t say anything about it to anyone we know. After I was finished with her I told her stay naked, and I went back into the truck stop to tell that someone close to me the deal, he was like wtf at first, but then asked if we was sure and I told him that he could ask her, but yes we were sure as far as I still knew. I sat in the booth as he went out to his van that I had just come from. About an hour or so later I decided to go out to the van, and it was rocking away, and I could hear her saying to him while moaning loudly, are you having fun you old big dick bastard, are going to cum again, hurry up please I’m getting sore. I went back into the truck stop and about 15 minutes later he come walking in with a big smile on his face not saying much, we then went out the van. My then wife was still naked when we got in, and I started getting hot at the thought she had just the hell screwed out of her 20 year old married pussy by a guy that was close to me that was 56. As he was driving us back to our place I screwed her sloppy loose sticky wet used pussy. After he dropped us off and left she said that he had got her off twice, but that he was a jerk and it wouldn’t happen again. That was the oldest my first wife had.
My now current wife told me that a friend of her dads that worked with him painting houses screwed her once in his pickup truck after her dad left a the job site they were working at together, she was 19 at the time, and her dads friend was 50. That was the oldest she ever had.
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