My GF's small frame makes hard/hurt, need some tips please!?

If it takes 15 min to get in even WITH lube, I wouldn't think that the pill is the concern. To my understanding, most can accommodate thick es (and babies). My advice would be for the two of you to go to a GYN. You seem mature yourselves, so talk w/the doc openly and honestly about what's going on. He/she can help you determine causes (other than just being very, very small), and solutions that will help you. One possibility is vaginismus - when the muscles tighten sooo much that entry is nearly impossible. The contractions aren't always voluntary and/or the woman doesn't necessarily realize her body is doing it, so don't feel rejected, ok? If vaginismus is the cause, the GYN or a therapist can give her, and you as a couple, some excercises to help relax and stretch the muscles.