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I've done this many times and enjoy it quite a bit.
When you're starting out be sure to do it doggy style. Have her just stand there and you should reach back and put it in. You should "break the seal" by pushing back onto it, not have her push it in. It will hurt a first, so just wait a second, and then push in a little deeper.
Once you have it all the way in start to move it in and out a little bit. Once you get used to it she can then start to thrust and you can stay still... but I've always found it hurt less and worked better if I could countrol the initial insertion.
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