First, you should chart your ovulation. There are some really good kits out there (some can be pricey) that can track when you are likely to ovulate. I read somewhere before that having sex every other day during your fertile time (starting about 5 days before your expected ovulation) is the most effective. Sperm can live in the uterus for up to 5 days.

As far as ejaculation goes, it sounds like he may have a mental block. That's the first thing that comes to my mind anyways. My good friend's boyfriend is the same way and he says it's because he doesn't want to get her pregnant. Maybe stopping himself for two years has now made it hard for him to just let go and do it, ya know? Talk to him about it and make sure he absolutely wants a child. Perhaps some doubts have made it hard for him to ejaculate inside you as well. Maybe he is comfortable for some other reason. Just communicate with him. Get him to try and open up. The more comfortable he is, I bet the more likely he is to be able to do it.

And some will leak out. It's unavoidable. But staying on your back for a few minutes is good.

Hope that helps!