Originally Posted by levite

Unexpected? I dunno. The couple of times I hooked up for a one-nighter were surprising, no doubt.

But honestly, I think the most unexpected was the first girl I ever slept with. I was very young. In retrospect, really too young to be having sex. But I was living in Minnesota, and there was nothing to do, so kids were having sex pretty young. And being an adolescent boy, it's not like I didn't want sex all the time. I just didn't think I'd be getting any.

I was a geek at that point (that changed later in high school). Chubby kid, read comic books and sci-fi, too smart for my own good, had a bad tendency to be a teacher's pet when I wasn't busy giving the finger to any kind of authority, tended to be a loner. Not, in short, the kind of kid who expects to be having sex any time soon.

I went to Hebrew school with this really cute girl. She was a cheerleader at her school, believe it or not.... Wavy brown hair, dimples, girl next door smile, all the right curves in all the right places.... Way, way out of my league. Maybe not even the same sport. Anyway, for some reason she had decided I was amusing, and deigned to hang out with me a little. She stuck with the amusement long enough for me to get over my shyness around girls that give me a terminal hard-on (shyness since overcome, BTW), and apparently she decided that smart and quirky and sensitive had their value, so we kind of became friends, and she would confide in me a little.

That was more than I expected. So I was more than shocked when she proposed that we have sex. In those days, there was no such thing as "friends with benefits," but that's essentially what she wanted. She had decided on me because I didn't go to her regular school, and so she felt comfortable having sex with me on the sly, so nobody would find out and ruin her reputation. At the time, of course, it never occurred to me that she was essentially using me for her own gratification, and that she would never have wanted her friends to know that she had sex with me-- that she would've been ashamed, not just of having her sex life revealed, but that she'd fucked a geek. But I just went along with the whole thing, where I wasn't her official boyfriend, and we didn't go on real dates, and she didn't want me calling her house, or showing up at her school.

I was living with my dad that year, and he was often away, so we just made regular times when she would come over to my place, and we would get it on. To be fair, she was quite hot, and very eager to explore her sexuality-- there wasn't anything I could think of at that time that she wasn't willing to try, in the privacy of my house. In retrospect, I probably should've valued my integrity over the sex, and not done it with her. But that's just not how adolescent boys think. So I shagged her rotten, and had a jolly old time doing so.

Lasted about eight or ten months. A lot of sex. Quality sex, considering our age and inexperience. And it was definitely unexpected. Social status and cliquism is never stronger than during that time of life, and yet...I spent the better part of a year fucking an alpha girl. She remains, to this day, the only cheerleader I've ever nailed.