Does anyone have any trouble getting it in while on top?

Okay so me and my fiancé always have sex. But it's usually with him on top. But this past week I got on top and it kind of hurt a little but then the pain went away and it was amazing! But then the next day when I was going to be on top again it hurt a lot, more then the first time. So I'm just wondering if this is common or if it's just the position. 

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