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Next time you are going down on your woman, place a lubricated condom over your middle finger.
As you are licking her clit, slide your thumb up into her pussy. When you begin to hear her breathing heavy and squirming around in enjoyment, begin rubbing her butt crack and sphincter with your condom covered middle finger.
According to Cosmo she will welcome, and become eager for insertion of the middle finger into her bunghole. Gently wiggle your thumb and middle finger once you have her within this 'bowling ball' type grip position.
Cosmo goes on to indicate that once the woman begins to appreciate this wonderful back door finger experience she will be conducive to some probing with your bone (once again - use the rubber due to the lubrication factor).
Enjoy! 
