So now that we've resorted to sharing experiences, I'll share one from several years ago that involved an older woman. Much older.
I had just gotten off working the late shift at a restaurant and before heading home, had decided to have a few drinks at the bar. As I'm sitting there in my shirt with loosened tie, I noticed, many bar stools away, an older woman drinking alone. I don't remember her being strikingly attractive and she looked quite sullen.
I wish I could remember how she ended up sitting next to me, chatting it up, but over a few cocktails she began telling me about the loss of her son just a year prior. He had been about my age, maybe older. She seemed like a nice lady, but at this point all I wanted was to get the fuck out of there. I had just ended a long shift, was trying to blow off some steam and this bitch was bringing me down.
However, after an hour or so of chitchat and having had too many drinks to drive home, she told me she was going for a walk along the beach. Which, incidentally, was just outside the restaurant. She invited me to meet her out there when I was finished at the bar.
So after mulling it over with another drink, I took a walk to the beach.

And after finding her there, we walked down toward the water, stopped and lay down in the sand. She almost immediately unzipped my pants and began blowing me, only stopping occasionally to slap my cock on her face. She'd clearly done this before.
While this is happening, a patrol car drives up onto the sand and shines a light on us. We somehow manage to get away with just a warning. And as we're walking back to our cars, she invites me over to her condo, which happens to be right there on the water. I give in.
Though as I locked my car in the garage beneath her place, I began to think this wasn't a great idea. She lived too close to my work, she was nearly the same age as my mother, etc, etc. What the fuck was I gonna do now? I was trapped.
As we walked to the elevator doors, I developed a plan. We boarded and got about three floors up when I flipped its emergency stop switch and hit the lights. I grabbed her by the back of the neck, slapped a big kiss on her, got undressed, and handled it right there on the floor of the elevator while a dim light shined through. Luckily, no one tried to board while this had gone down.
When we were through, we got dressed and took the elevator to the floor of her place, where we said goodbye, she exited the elevator, and we never saw each other again. I got the fuck out of there and hadn’t kept the job much longer to run into her.