Seeing a guy for over 2 years but not in relationship how do I ask for it with out being pushy?

I have been seeing a man for over two and half years as FWB he has had 3 really bad relationships and was at one point hung up on his ex but at the time it didn't bother me as I wasn't ready for a relation ship we have never really taken it to the next step of going out on dates and meeting each others friends our children know each other and until i put mine in a different school hung out alot he and I had a personal incident between us from July to Dec last year were it got heavy and tempers on both parts flared both of our feelings were hurt and and one point we did not talk any way he made contact in mid dec and we started talking again etc and at the time fair enough to him he said we both could have handled the situation better but he did want to still be friends etc but that I did want more than he did and if it happened in a couple of years things would have been difference as he was just enjoying himself and having fun now since then we have seen each other a few times and he has said a couple of things that confused me like how it would be ok if i wanted to go have fun with someone else whilst he is away as long as I used protection etc although that is not what he is doing he is only seeing me what is that a Test ?? I don't want games and I do really want to try to start to take the steps to start seeing him as a boyfriend level but as he has been duped/scared by 3 women before me so can someone please tell me how to do this without scaring him off as he was the one who intuited the return of our contact so its got to mean something especially since with both told the other that we never wanted to talk to each other yet here we are starting over again he is 37 I'm 30 i just don't know how to take those steps with out being full on and don't want ot be hurt again myself