Had lots of luck meeting chicks for same-night-fucks on Craigslist, as well as some repeat customers, all surprisingly attractive and just looking for some NSA intimacy. Especially when you're sweet and nice and mature, and not all like "HAHA LOL LETS FUKC!", you'd be surprised what kind of talent is lurking around looking for something quick and easy. Back when I was much younger, I used to meet a lot of 18 and 19 year old DROP DEAD GORGEOUS girls on Craigslist who simply want to get our of their parents house and hang out at your apartment. I'm in the most meaningful relationship right now and have been for almost a decade and wouldn't trade it for the world....but I'd be lying if I said that playing the Craigslist game isn't by far the most fun way to spend a rainy boring evening.
Having said that, I've had my not-so-fruitful encounters from Craigslist too. This one time I was talking to this insanely hot, petite blonde chick who sent me all sorts of pictures and seemed way into me. So after a couple days of emailing back and forth, we decide to meet. Turns out the pictures she was sending me was from several years ago before she developed a.....problem. She was about (no kidding) 3x the size and weight of the pictures she was showing me, and turned out to be super awkward in person. Me being the gentleman I am took her home and fucked her anyway, dick barely reached past her meat flaps, and I somehow, someway, we may never know, but I for some reason came instantaneously. Talk about feeling confused after that....
Probably my worst sex experience.
There was a funny one I had with another Craigslist encounter. A girl I formed a FWB situation with, I was fucking her on the edge of her bed, and literally JUST as I was blowing my load all over her pussy, her dog pushes her bedroom door wide open exposing us to the entire living room, parents, brothers, friends, etc.. Luckily, they were the kind of people where they thought it was funny. 8(