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Try pushing out with your pelvic muscles, as if you were trying to take a dump; then pulling back, like you were trying to hold it in. If you're using a vibrator, turn it on low and let it buzz against your asshole. Soft and flesh- like to the touch. My first recommendation is to usually just experiment with using some lube and a finger to start off with. Misha's Cock-squeezing Asshole Tags: This is an extremely serious condition, and can be fatal if not treated immediately. Easy to clean, and can handle any type of lube.