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Does fingering hurt and what does the girl do during it?

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I'm 14 and there's this guy that I really like and he really likes me too and we are basically going out. And so he said that he wanted to finger me and I have no problem with that, I actually want him to so ya.. but like a few questions:: Does it hurt when you get fingered?? What does the girl do when he's fingering you?? And if he pops my cherry (he said he really wanted to) I know that I might bleed but what does the guy do when I do bleed? Just take out his finger for a bit and then put it back in??