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#1
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I only have experience in topping... and good advice has already been given here.
Before I go in I prefer to get her relaxed, lubed and ready to receive my cock. I start by gently stroking my tongue around her anus and poking inside with the tip of my tongue while swirling it around. I generally get really turned on and begin to salivate quite a bit, producing more than enough "lube." When she's ready I like to slap the head of my penis on her anus and gently press in, sometimes I'll spit on it some more to get a little extra lube and let it slide in. I just work it in little by little until its sliding freely and begin going at it balls deep.
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#2
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I always insert a butt plug first it makes me very horny. I love to feel full of cock, girlie cock that is, pounding my asshole. I love it bareback and I love it when she shoots in my hole!
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