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Portnoy's Complaint, Philip Roth"Then came adolescence-half my waking life spent locked behind the bathroom door, firing my wad down the toilet bowl, or into the soiled clothes in the laundry hamper, or splat, up against the medicine-chest mirror, before which I stood in my dropped drawers so I could see how it looked coming out...I once cored an apple, saw to my astonishment (and with the aid of my obsession) what it looked like, and ran off into the woods to fall upon the orifice of the fruit, pretending that the cool and mealy hole was actually between the legs of that mythical being who always called me Big Boy when she pleaded for what no girl in all recorded history had ever had. Oh shove it in me, Big Boy, cried the cored apple that I banged silly on that picnic. Big Boy, Big Boy, oh give me all you've got, begged the empty milk bottle that I kept hidden in our storage bin in the basement, to drive wild after school with my vaselined upright. Come, Big Boy, come, screamed the maddened piece of liver that, in my own insanity, I bought one afternoon at a butcher shop and, believe it or not, violated behind a billboard on the way to a bar mitzvah lesson."
How can there be a list of great masturbation moments in literature without Roth's Portnoy? There can't. The hard part is choosing which one, really. But anything that involves fruit and the words "Big Boy" is clearly a winner.