I agree with Have Hope. You need to open up this conversation with her.

She may have had a lot of sexual experience but it doesn't mean she has a high sex drive. She may be comfortable with her body, etc, but doesn't mean she's comfortable initiating.

Maybe it is a gender issue. Many women (but not all) feel more comfortable being pursued.. just like you.

So my question is, if you spent all that time massaging, why not take it further? Because "you're" shy.. and maybe she's going by "your" comfort level.. but wants to assure you she's definitely interested.