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Sorta glad this thread got bumped. I have far too many cringe-worthy stories to tell, but here's one that takes the cake.
In high school, I was cast as a minor character in a school play. A girl, a couple of years younger than me, was cast as my opposite. Since we were both extras, we spent a lot of time chatting backstage during rehearsals. She was on the shorter side and had some meat, but she had a legitimate D-cup rack, some piercings, and short black hair (think Suicide Girls). We talked about sex quite a bit and she would tell me about the things she did with her then-boyfriend. We're talking kinky stuff for teenagers - she was into anal and liked cum inside her ear.
We ended up exchanging ICQ numbers and she would always want to chat with me online. When I graduated high school, she asked me on several occasions to go out for bubble tea or to give her rides. Being an repressed Chinese kid, I of course didn't take her up on her offers and she eventually stopped messaging me.
Ahhh, memories...
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