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At a newsstand in Hollywood with my mom. Seven years old. Pointed to a Playboy and said "Mom, will you buy me that?". She just gave me puzzled, "who farted?" look and walked away to buy a reader's digest. Kinda funny when I look back on it.
First porn video was at some friend's house. 12 years old. One fucking very weird video: one of the scenes was this disgruntled waiter arguing with a old woman customer because she wanted more mayonnaise on her turkey sandwich. So the waiter goes back to the kitchen, whips out a cooked turkey carcass and starts fucking it with fervor. When he jizzes he puts it on her sandwich and she goes "Mmm, delicious". Totally fucking bizarre. I didn't realize how fucking nuts that was until I got older.
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