I am 23, so this will probably sound silly and foolish but I don't have anyone else to ask these things so here goes: First off, how do you know it's in the right hole? My boyfriend and I were getting involved last night for the first time, and at first it hurt horribly like I was being ripped apart. He re-adjusted and it still hurt a little but nothing like before, it was mostly just a lot of pressure. Was he in the wrong hole before? How do I keep that from happening? Also his penis is BIG and my vagina is not. How far in should he go? Can he cause damage by going too far? Thanks for the advice.