Funniest and hottest story of my life right here:
Growing up in a small, redneck community, I wasn't going to come out of the closet anytime soon. I had to find an outlet for my sexual desires, even if just for a single night. I resorted to Craig's List the day I turned 18.
So there I was on craigslist.org, flirting around, trying to get an idea of who I should give my anal virginity to. The majority of those who responded to my post were older men. I was kinda appalled at first. Yet I couldn't resist playing around with the idea of pleasing a man who is two or three times older than me; the more I thought about it the more I realized just how hot it would be.
Still indecisive about choosing a stranger from the 100+ responses I received, I decided to look at what some of the old men were posting. I settled on one who had a nice little cabin "in the middle of the woods" who was (so his post said) 51. We conversed via e-mail a little bit and I found out that he was a teacher; A teacher I suspected that I knew...
"So what school you teach at?" I asked him.
"I teach at so-and-so High School." He replied.
"That's so funny! I'm a student at so-and-so High School. What subject do you teach?"
It was a long wait before I heard back. Finally, he told me that he could not reveal his identity until I told him mine. I knew exactly who it was because he types like he talks. Since he stubbornly refused to admit who I thought he was, I made it equally as tough for him to figure out who I was. Because the school was so small, he eventually narrowed it down to about five possible students. At this point, I admitted my identity...
...But the old bastard didn't keep his promise! To this, he acclaims that he feared losing his job; I guess I can understand that. I knew damn well who it was but I still needed to hear it from his face. He was my favorite teacher and I had him for two classes. I'd shoot a teasing glance at him whenever I got the chance. It was pretty fun relationship even before we ever had sex, I must admit.