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It depends upon the person or if they are tense or not. With my partner, the very first time we were so turned on and horny (well lubricated), that it slipped in very easily and sex didn't hurt at all. Generally if a woman can masturbate or finger themselves especially with more than one finger, then natural sex will probably not hurt at all the first time. A total virgin that has never touched herself before will probably have some pain at first.

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Q: Is there a way for sex not to hurt for the first time?
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