While I was in law school I was of course really stressed out, going out of my mind studying for exams. When I am stressed I tend to get really horny which is kind of a problem because it makes it even harder to work. At that time (around 2007) craigslist casual encounters still existed – it was full of prostitutes and dick pics. I was really surprised at how many dick pic posts there actually were, because that shit can’t work, right? *Right?* Unless…
So I posted my first ever dick pic personal ad. It was called something like “8 inches for you,” with a couple of pics of my cock from angles that made it look enormous. Yeah, those were simpler times. Shoulda been there kids.
To my incredible surprise, among the responses from gay men, bots, and prostitutes, there was an actual woman. I was about 23 at the time, and she must have been about 10 years older than me. We chatted on AOL instant messenger for a while (I’m so old lol) and she sent me a bikini pic. She was hot! So at this point I thought maybe she was just a very dedicated scammer, and I proposed that we meet at a bar near my apartment.