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Try a few different positions when starting and see if that makes a difference. My gf finds spooning painful if it is the first thing we do, but if its round 2 no trouble. Also start by entering really slowly, and try teasing a bit with your penis; only go in a little bit then hold it for a few seconds and pull out before going in again. You could also try fingering a bit more to loosen it up a bit.
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