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I have some doozies from babysitting but this remains one of my best kid stories.

I babysat these two awesome kids, at the time 7 and 11. When their dad was away and their mom was out late I’d put them both to bed, first the younger boy then me and the girl would tidy up and watch TV or something, then she’d go to bed. One night after I’d put her brother down, the girl asks me if I know what gay men do for sex. I was kind of flustered by this, but I knew she’d already gotten the sex talk and their parents were super liberal, so I figured I might as well tell her the truth. I didn’t get into details, just the basics. She thanked me and went to bed.

A week later, I’m there again and the boy wants to show me the drawing he’s bringing into school tomorrow for his “Teach the Class” project. It’s a huge sheet of bristol board with coloured pencil drawings of two male television show characters having anal and oral sex, and comparing dick sizes (that one had speech bubbles). I almost fucking choked. He informed me he’d been listening to my conversation with his sister.

I told his mom and she talked him out of bringing it to school. She found the whole thing fucking hilarious.

http://www.reddit.com/r/AskReddit/comments/jf9m0/whats_the_most_hilariousinappropriate_thing_youve/