Mrs. Robinson

I was 19, having just finished my freshman year of college. I was a combo math geek and swimmer, and that summer I was tutoring kids for their SAT’s, which paid well, and trying to swim as much as I could. I was on our college swim team, but, as I look back, a shoulder injury and reality would lead me to quit midway through the following season.

But, at that moment, I was in great shape and hopeful that I could shift up from being an okay college swimmer. Over the summer, I would sometimes go over to my high school and swim at their pool with a bunch of guys, but I’d also sometimes go to an outdoor pool in the backyard of a high school classmate.

And on that day, I was in the friend’s backyard. To be clear, it was a big pool on the estate of a rich family which spent the summer out of town. The classmate was a girl I never hung with, but they’d offered their pool, and I’d accepted.

On that day, I’d spent an hour doing a rigorous practice, and was feeling good. It’s easiest to feel awesome, of course, when more elite athletes aren’t around to remind you of reality. But on that day, I’d done my workout and then spent a few minutes on a float, just gazing up at the warm blue sky.

As was often the case when I was 19, a few minutes of quiet led to an erection. Sadly, automatic erections don’t accompany aging, but that’s a different story.

So on that day, I was on a float, with a big erection, in a skimpy speedo. The question wasn’t whether to jerk off, but when and where. No one was home, but it wasn’t my house. I’d never cum in a pool, but that would make me a bad guest. Though, to be honest, I wouldn’t have hesitated if I could have guaranteed that I wouldn’t get caught.

Anyway, I began to rub myself but decided to head into their cabana, which would afford some privacy. As I got out of the pool, I was shocked to hear my name being called.

“Oh, hey, Mrs. Stilton.”

“Hey yourself. Did you get in a swim?”

“Yep, thanks again.”

“No problem. Happy to help the big swimmer.”

“What are you doing here? I thought you were at your beach house all summer?”

“Just in for my goddaughter’s wedding. Everybody else stayed at the house.”

I wondered if she’d seen me rubbing myself. Probably not. I was out of the pool, quickly draping myself with a towel. I looked again at Mrs. Stilton, who was wearing a sundress. She was a trophy wife of an aging oil baron, but not a big brassy trophy wife. She was a preppy, petite version of a trophy wife. She’d gotten a masters degree in art history from Columbia, so it was said, before she’d moved to the middle of the country with her husband to have her kids.

The two of us had also been recognized in the “senior favorites” from last year’s high school graduation. I’d been named “most likely to ask a weird question that the teacher can’t answer,” a category which struck me as targeted at me, while she had been the near unanimous recipient of MILF. Over the past few years, I’d jerked off to her face many times. Mostly mulling her blowing me, but also to just fucking her, generally doggy style. I recall feeling a penile pulse at the thought.

We sat down at a table next to the pool. She offered me an iced tea.

“So how was your freshman year?”

“Good.”

“All A’s?”

“Haven’t heard yet, but I probably did okay.”

“What did you take?”

“Math, econ, history, chemistry, basic stuff.”

“Which was the most fun?”

“None of those are really fun, but i did like my massage elective. “

“You took massage?”