I have skim read this so could have got a few wires crossed but my thoughts are, don't play a dating game, don't worry about 'the rules', all this nonsense is what over complicates things.
If you are getting to know him then you want to see him in lots of situations so you can see the sort of person he is. Arrange dates doing fun things whether it be a walk out somewhere nice, ice skating, cinema, pub with live music, gallery, whatever you like to do. You want him to do things with you that are every day things you like to do.
Once you have established a more intimate friendship between you two, when to kiss him or have sex will be irrelevant as it will just happen.
The thing is, we can only do what we feel is right based on what information we have. If the other person is playing the dating game and takes things further with you before you are ready really then if it doesn't work out you might regret it. If it is something you, however, want to do then no regrets eh? You have been true to yourself and they have jsut proved the type of person that they are.
They only thing to remember is to practice safe sex when the time is right for you!