Tag: High School

Somebody told me to post the story here, so I figured I would.

In high school, I had a history teacher that was a little bit of an oddball. She would make the class do things that were a little out of the ordinary and people would often call her crazy. At some point, she mysteriously left the school and I never really heard from her again.

Years later in college, I somehow managed to reconnect with her. Turns out that she lived in the same city that I went to college in. Apparently she (34) was going through a divorce, and me being the naive 20 year old that it was, I figured that it would be nice to reconnect and maybe see if I could cheer her up with my company. We met up over coffee and caught up, eventually getting to the point of going out almost every weekend to go hiking, getting dinner, going shopping, and more.

She would buy things for me sometimes, sometimes she would even give me bundles of cash. She once handed me $300 and I was almost convinced she got it through illicit means, but no, she apparently was in a church that was allegedly culty and she convinced some of the members to raise money just for me. Read more »

During the summer after my freshman year of college (which was a long-time ago), I went to one of my sister’s band concerts at the high school I graduated from.

The concert was in the gym and the bleachers were pulled out for all the family and friends to sit in. I was feeling good about myself being the older brother in college and, of course, my libido was sky high, so I kept one eye on the concert and the other eye on every girl who walked in to decide if they were old enough to pursue. And I remember doing all this while my parents were sitting next to me talking my ear off.

Then she walked in.

She was the older sister of one of my sister’s friends. She looked up and we locked eyes, and it was like a bolt of electricity rocked both of our bodies. The attraction was instant. I knew I needed to fuck her.

She was a brunette but perfectly thick. And her boobs looked amazing under her maroon tank top. Read more »

(Warning: very long story. For those who want to skip the background and/or lead-up, medium-sexy stuff starts at / / / / /, actual sex starts at +++++. Honestly though, the story’s a lot more fun in context.)

Of all the people I’ve dated, Kelly was decidedly the strangest. This absolutely brilliant, blonde scientist who embodied “slim thicc” was sweet and demure in public, usually dressed in jeans and a cute sweater in cooler weather and a sundress in warmer months. Very much your wholesome girl next door vibe, but that was decidedly inaccurate behind closed doors. Or beyond them in this one case, I suppose. When I introduced her to friends they’d always comment about how wholesome and gentle she was, and they weren’t wrong. It was just a very incomplete story.

In private, I’ve only known a tiny number of people kinkier – and even then only because my best friend is super into that scene and I’ve met some of their friends. 😂 I’ve certainly never dated anyone else on Kelly’s level. In retrospect some of it was so far outside my comfort zone that a couple occasions are memories I try to block out, but it was always consensual even if there was occasionally more pressure placed on me to acquiesce than there ought to have been. But most of it was fun, or at least benign albeit strange – like wanting me to call her “kitten” while we were having sex. Read more »