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| Updated April 29, 2021 Women reveal their first experiences with masturbation. I can’t specifically recall the first time I ever masturbated. Though, if I had to guess, it was probably in middle school after watching an episode of MTV’s “Undressed.” During those years, I remember a few instances of curiously gliding my middle finger in and out of my vagina, feeling around a little and wondering: What’s all the fuss about? The first time I really masturbated in a hot-damn-give-yourself-an-orgasm kind of way was a lot more memorable. I had recently turned 18 and a couple of friends had bought me a vibrator from Spencer’s named “Ever-Ready Freddy” as a gag gift for my birthday. Freddy had an intense, menacing face and if you pressed him a certain way, he’d say one of his signature catchphrases, like: “Hell, can’t you get a real man?”