What’s the strangest sexual experience you’ve had?

Somehow, it all began with me using the leg press machine at my old gym. It wasn't one of the nice ones, either. You had to climb in while the weight rack was lowered, contort yourself into a vaguely ergonomic position, and then start your reps. As to why we didn't have a traditional plate loaded machine, I'll never know.

Anyways, I'm in the middle of a set. It isn't pretty, mind you. Legs are up, everyone on the cardio machines has a plain view of my sweat pant-clad ass. I hear somebody talking over my shoulder.

"Do you think our fate is predetermined?"

I turn to my right, and see this girl standing there. She was probably around my age, and conventionally attractive. I was halfway in a daze from finishing my set (I used to super set on the leg press at the end of my lower body workouts), but did my best to humor her. I didn't want to be an ass or anything.

"Excuse me?"

"Do you think that our fate is predetermined?

I remember saying something like "I can't imagine this conversation to have been fated, if that answers your question," but I probably said something remarkably less witty. Actually, I'm sure of it.

Anyways, she follows up with "Well I just wanted to see if you were as smart as you are attractive, is all. You should totally take my number, you know, in case you change your mind about the whole fate thing."

Two things you need to know about me: 1) I don't get hit on often, and 2) I'm awful at telling people no. So we trade numbers, talk for a little bit, and she goes back to the squat rack across the room. I'm halfway thinking that I've been the victim of a prank or something, and decide to finish off my set and go home.

I get a text from her later in the evening. She wants to know how my day was. I said something along the lines of "Better now that I'm finished working legs for the week, lol." Without missing a beat, she gets back to me:

"Probably be a lot better if you fucked me tonight, huh?"

I forget what I said. She ended up sending me her address, though. Part of me thought that the whole thing was all too easy, and that I was going to end up on dateline or something. Against better judgement, I decide to go to her place. Her folks are out of town, and she's waiting for me in lingerie. I start feeling nervous (I was a teenager - give me some slack!), and for whatever reason ask her for something to drink.

We both get drunk, start making out, and eventually get into it. Halfway through I find that I'm having a hard time staying stiff, and after awhile we call it quits. We make out some more, she sucks me off, and we spend the rest of the night shooting the shit. I explain to her that I just got out of a long-term relationship, and so was having a hard time being intimate with other people. She laughs, and tells me that she's got the same problem: Apparently, I was supposed to be a cathartic one night stand.

I ended up staying the night. We went for breakfast the next morning, talked some more, and then I went on my merry way.

It doesn't make for the most satisfying ending, but I never really saw her again. She's messaged me a few times here and there, but we both ended up moving away not too long after our "shared experience." Still, cold approaching someone like she did took guts; with confidence like that, I've no doubt she'll go far in life.

TLDR: I was solicited for sex, wound up providing drunken therapy instead.

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