This is a little long because almost every detail is permanently burned into my brain, and figured I’d share every bit! Ages reflect ours at the time – I was 23, she was 19. I’m 36 now.
Years ago I had started talking to this girl after posting an ad on craigslist (before dating apps!). Once I determined she was actually a real person, I got a photo – really cute, a petite 5’0″, long dark brown hair and a great smile. Her body was well-developed for her age and I could hardly believe someone this cute would actually contact me through a sketchy website. For comparison at the time, I’m 5’10”, a wider and somewhat muscular build.
After talking for a bit, we go on a date – pretty standard chatty lunch just feeling each other out. I propose we walk towards where she lives because it’s on the way to my place and we can talk more. As we walk, I decide to try to get a little more personal and see how she reacts. I find out that she has only had one sexual encounter before, and isn’t sure what she likes. Not too surprising for someone 19. I don’t prod too far, because it’s our first time meeting and since she’s young I don’t want to push into uncomfortable territory and turn her off.