One of the hotter relationships I’ve ever been in was hooking up with an older woman. I had been fantasizing about it for a while, like a porn thing, but decided to give it a shot. Why not. I’m a 25 year old white guy, nothing spectacular, but good enough, I think.
I set up an OKC account and started messaging older women. It was all cold calls, shooting my shot and seeing what happened. Almost nobody responded, and even fewer responded positively. After a while, though, one did respond, asking why I was messaging her and not someone my own age. I was straightforward, and said that I liked the idea of a discreet, no strings attached relationship with an older woman, that there was something hot about being a younger guy getting with an older woman that he isn’t supposed to get with. I ended my explanation with “if you’re feeling bold.” Not my usual style, but this was just messaging online and I figured I could be a bit…bold.
She responded, “I am bold.”
We exchanged numbers and texted for the next week or so. Nothing too salacious, but explaining what I was looking for, and getting more comfortable with each other.