I [M41] was in my 20’s when Craigslist had a Casual Encounters section. For those of the younger generation, this was before the days of Tinder. The technology was older, but the game was the same. I had MANY adventures with meetups, but a lot of times the fun was virtual (we called it ‘cyber’ instead of ‘sexting’ back then). I would post an ad with a subject line like: “CRAVING an ORGASM before bed?”and say something along the lines of “If your body and your mind are craving…satisfaction… before bed, I dare you to give me a try; I promise you will be surprised by what I can do with my keyboard. You have nothing to lose and only pleasure to gain. ORGASM GUARANTEED”. Then wait for the satisfying ping of the response notification on the old email inbox and off to the races on IM (I know… ANCIENT!). Made MANY nights enjoyable!

The closing of Casual Encounters represented the end of a Wild West era of the internet. There are new ways to play, but I miss the old days.

Any old timers here with fond memories of that era? Feel free to reminisce in the comment section.