I’m a private tennis coach and this happened this summer.
I’ve coached many cute girls and some MILFs, and even casually ‘went out’ with a couple before this, but nothing ever came of it sexually. From the very first lesson with this girl, I could tell that things were different. As soon as she should up to our first scheduled lesson, she looked at me and her eyes widened, pupils dilated, and she became visibly nervous/taken aback. She was asian, very nicely built, about 30 years old. She was wearing tight tight spandex shorts showing off her ass — you could catch me peekin’ for sure. During the second lesson, we casually talked about hiking and I went for it: “Do you wanna go hiking sometime?” She paused, smiled and said “I’ve love that!”
After our hiking date, where we felt each other up and got generally cozy, we felt pretty comfortable around each other. The next time we went out was to a nice restaurant. She has a Maserati, and let me drive us around in it. So that was pretty fucking cool already.