This happened when I was 22. When the casual encounters page could still be found on craigslist. I’m now 28. I had been trying for a couple months, to find a woman who would like be my first fuck. A few close calls, but everything kept falling through. Until one day in October. I get an email, from somebody who is interested. She’s 38 years old(let’s call her Rachel), from my home town, and is turned on by the thought of taking the virginity of a much younger man. We exchange numbers pretty quickly. We’re talking through text while trimming weed. She sends me some nudes of herself. I am instantly turned on. She is incredibly hot, a milf to die for. I told her I was turned on, and my cock was now hard. She asks to see! I of course, happily oblige. Take two pictures of my cock , and send them to her. (I am working, but I’m alone in a shack, on somebody’s property, with 2-3 pounds of weed on the table in front of me.) She is impressed by my size, and how nice my cock looked. It doesn’t take long for her to ask to meet me later that night. I was in shock, I was about to be laid for for the first time. We agree on a time I’d pick her up.