I've had sex with more than a hundred people over time. I chilled out in my mid 20s, mostly because I caught herpes around 24, can't exactly be a manwhore spreading disease. I also didn't trick people into sex by telling them I loved them or anything. Saw a lot of other guys do that all the time. Mostly to get the hot women. I didn't really have standards.
A lot of my hook ups were late 90s to early 2000s web chat ones. I have had to hide in a closet for 2 hours once because somebody came home, they always left that part of it conveniently absent. Another time I had to squeeze through a window about ten inches wide and then jump off a roof. Another time me and my friend were both with this girl and her mom came home. We managed to get our clothes on in time and acted like we were just hanging out. Apparently mom's date didn't go so well, so she then decided to hang out with us... no it didn't go there but we did go back to sexing when we thought the mom had went to bed- and then she totally busted us like mid stroke. The girl was like "mom, god damn it, im trying to get fucking laid here!" The lady said something about a gun and I don't think I've ever gotten my clothes on so fast. My buddy was taking his time and I fully expected to hear shots start as I sat in the car waiting for him. So he finally comes out and the girl comes running after him in a blanket yelling "wait, can i get your number?"
I've also gone out to dinner with a hot 40 year old woman and it was the most awkward date ever because everyone was staring at us. I was like 28 at the time but I look young. She does not look too young, but she was a gorgeous blonde. It seemed like we picked a place with mostly other middle aged men out with their guy friends, and they were like super jealous. We went back to her place for "drinks" after. That lady was lots of fun. Oh my goodness. She would say to me, "How did you learn to be such a good lover at such a young age." I laughed and told her she didn't want to know.