Me personally, the best ways are on my back, but the best way is on top of him because that way I'm in control of the pressure and how deep it goes. So you might try it that way. It's a lot easier to relax enough when you know that if it hurts you are the one who can move away and all that. Just be patiant. It also may help if you "stretch her out" (how vulger of me, sorry) with a toy before you do it too.
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