waiting for marriage or not, it would appear she is in need of some serious advice. As a male, from what I've read, entry should be taken very slowly and you should be VERY lubricated and have him enter you VERY SLOWLY AND A LITTLE AT A TIME...it may take a few sessions of love making to get all or most of the way in...
I'm sure women with similar situations will responded..
Jim
I agree with zam - wait until you get married, then you'll be alright because you'll be able to enjoy it without worry