It still hurts, bad.

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So like, ive had sex about 6 times or so with the same guy. And every time we have sex and he begins to push it in me to start, it hurts as if I'm losing my virginity again. I'm kinda confused. I thought you get used to it? 
Like we have foreplay and we get wet but once he starts to push in it hurts like a mother-... So I'm lost :/ 
Plus then when he does enter me, and begins to move I'm fine and we can go hard for over an hour and be fine.