Re: LMR'ing w/ hesitation but with willingness from girl how to break ice?
Personally I don't take girl's virginities. I have, but only when I'm in a LTR with them. They get it in their head that the first time is going to be some magical thing where everything goes perfect and it's wonderful. Sadly, it's usually awkward and painful for them as it's something new. That's just my personal opinion though.
I would just let things escalate naturally. There are plenty of other fun things to do besides sex and if it does end up going to sex, then good job! If not, you still had fun, right?
You are the prize. She needs to earn it.