Two
I normally go for girls my age or younger, but twice I've nailed cougars (and maybe one or two more when I was in the military, but those memories are fuzzy due to alcohol ).
The first one was quite interesting. Probably my greatest day sexually ever. I nailed my 24 year old girlfriend after we worked out at the gym. She was cheating on me and I knew it, but she was a great fuck, so I decided to continue in it and just fuck other chicks too.
She was a bartender and had to go to work, and I was off. So I went over to a friend's house who had a pool. A girl from work was texting me about her jerk boyfriend, so since I'd been eyeing her for months I told her to come by and bring a swimsuit. Well, the 18 year old hottie showed up... with her prick boyfriend. Lame. Anyway, apparently she wanted to make him jealous because she kept rubbing on me and flirting obviously. He was the smallest marine I've ever seen and though he looked sullen, never said a thing! Long story short, I took her into a room and we made out. I kissed her all over and she gave me head.
Later the same evening I went to a dinner party at a lady's house I had been invited to. It was being given for some German college students that were hiking a local trail and were in town for a few days. Two couples, although I didn't know at the time. I had my eye on one of the girls, but it soon was clear that one of the guys was with her. She ended up getting a little sick, so the Germans all went back to the hotel. There were also a couple girls my age there who lived next door. One was a wet dream, but I could never quite figure out if they were gay. At any rate, they left too.
I figured I'd be nice and offer the woman who threw the shindig help doing the dishes and cleaning up. She was a blonde, 45 or so, well built with large tits and a nice ass. She was good looking for a 45 year old, but no thought had even crossed my mind about screwing her. After we cleaned up we chatted for a few minutes an I was going to leave as well. She thanked me for being so thoughtful and told me I was welcome to crash in her guest house since nobody used it and it was late. After considering, I accepted. She got me some blankets and we said goodnight. When we hugged the whole atmosphere became instantly sexually charged. Without even thinking about it I kissed her and 10 minutes later clothes were all over the floor of the front room of the guest house. We weren't quite naked, but both were moaning and panting and kissing and grinding. Her bra was under her tits and she still had her panties on. Just then, the two neighbor girls came over to discuss plans for the next day. Since it was summer, only a screen door was closed between us, and they had a full view of our passion.
So... we didn't fuck that night, but apparently she hadn't been with anyone in a couple of years, so was ready to have me over soon and often. I think I nailed her the next night, the night after, and she wanted it in her ass the third night. That was the only woman I've ever been with where I could cum and keep fucking as if I never had. She kept me hard for hours. I once came in her mouth three times seconds apart ( best and most unusual orgasm ever!) And still was able to fuck her!
Wonder what ever happened to that chick?
I know I said two milfs, but this is long, so maybe later I'll tell you about my mom's friend. Haha
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