To start things off TALK TO HER!!!

Communication is sooo important and talking about things before they happen will ease some tension. Ask about what she hopes will happen and maybe try and work some of those things into the night (make sure its not the same night though so u can prepare!!!) don't pressure her into it!!! That's very important too

Everyone is different

Wrong! It's always uncomfortable the first time.

I wouldn't be able to tell you if she would be hurt or not because everyone is different and it all depends on her body type. Also talk about birth control beforehand.

Careful what he says to her. She may already be assuming they are forever.

And then have fun and most importantly make sure you tell her you love her (but only if u mean it!!!)

good luck =)