This happened when I was in high school (around the age of 16, I think)--

I had been dating this guy for about four months, and our relationship seemed to be slowly going down the drain. To spice things up, I decided one day that I was going to write him the most X-rated letter I could possibly come up with. Well, I wrote it and gave it to him, and he loved it. All went back to being wonderful...

Until his little brother, who was a freshman at the time, got his hands on said letter. He decided, "Wouldn't it be great if I take this to school with me, and show it to all my friends?" Even then, that wouldn't have been so bad, since I wasn't friends with any freshmen, and I'm sure none of them knew who I was.

Well, the bastard lost the letter. On the school bus. The same school bus that the track team used later that day to go to a meet. Turns out, someone on the team found the letter, stood up, and read it at the top of their lungs to the entire bus. Oh, and did I mention that about 75% of the track team at the time was people from my grade? And that they all knew me? And that I had signed the letter using my full name?

On the day of my graduation, the guy I was assigned to sit next to, whom I hardly knew, turned to me and said, "Wait, you're the girl who wrote that porn letter to Andrew, weren't you?" Oh, the horror.