Can a women become pregnant off of pre-cum fluid alone?

My girlfriend and I have been having sex for over 2 years now, but she is still very "tight", and really has to get into the mood before I can penetrate. It's almost as though we're having sex for the first time, every time. Sounds romantic, but it's a bit annoying for both of us (and she finds it painful if I accidentally push too quickly). With my ex I could slip a finger inside her without any hesitation, of course I would never mention that to my girlfriend. Once we're into it, there's no problem with going harder and faster, it's just that initial thrust. Is this normal? By being so gentle the first time have we possibly never broken her hymen? Otherwise, if we have sex more frequently, rather than maybe once a week/fortnight/month (for now we both still live at home with our parents) will she likely open up a bit more?

I take oral contraception, no biggie there. I was recently put on amoxicillin by my doctor for a sinus infection. I think I developed a yeast infection as a result. I had one before way back when, so I knew what the symptoms were. At any rate, I bought one of those over the counter 3-day cure kits. However, I forgot that the goo was supposed to be inserted at night and I instead put it in during the day (triggered mostly by the fact that I started using the kit as soon as I got it home and repeated the dose at the same time each day). It's three days later and it still itches a bit down there. Did I totally botch the goo? Should I try again?

Additionally, my fiance comes home from six months of overseas military duty on Friday. I'd like to be able to sleep with him then (hence why I'm trying to get this all cleared up), but we use condoms as one method of birth control and I've heard that these over the counter yeast infection cures decrease their effectiveness and cause them to break. What can I do?

Me and my girlfriend were both virgins and just had a go at intercourse for the first time. Unfortunately, her vagina is really tight and is pulling the foreskin on my penis back causing pain for me and also for her. I've fingered her a few times to help loosen it up, and wore a condom to help with the lubrication, but it's just really painful. Is there something wrong with my penis, or just too much wanking?