This story occurred in early 2016. It involves me meeting up with an older married woman I met through Craigslist for some of the most thrilling sex I have ever had.
I was 26 years old at the time and had just finished grad school and was working at a summer internship with plans to move in a month to start a new job in a different city. My then-girlfriend and I recently broke up over a petty fight and I wasn’t keen on looking for a new relationship, especially with only about a month left before I moved away. However, I did want someone to fool around with, if possible.
It seemed like a long shot, but I created a few posts on Craiglist seeking a no strings attached hookup with each post centered around a different fantasy or activity that turned me on. One of the posts was searching for a woman to watch me masturbate or mutually masturbate together; it has always been a turn on for me to finish in front of a partner. Unsurprisingly, I got myriad responses from bots and dudes. With the sheer volume of “m4w” posts online, I figured I had a snowball’s chance in hell at finding a sane, attractive woman through such a seedy medium. However, fortune was soon to favor me.