haha i think we all had the same questions when it was our first time too. And believe me you are just going to keep asking the same kinda questions over and over again till you actually do it yourself. truth is, it's different for everybody. so you aren't going to find one final answer. it is going to hurt, but your bf cares about you and will take things slow for you. and he can even stop it you want him to. In my experience though even though it didn't hurt me that bad the first time, it did hurt for like the first 2 or 3 times. but never as bad as the first time did. It sounds like you have a great bf, that you love and trust.....take pride in that. You did say it has to happen sometime. Where is there a better guy to share it with than ur current bf.