I find it interesting that he quizzed you on where YOU went when he said that he felt like he was checking in with a probation officer. He wants to have some control of you, but not the other way around.
I think you need to not worry about the emails. If he wants to, he will. If not, don't write to him. As far as him being needy - he obviously is, if he has two women.
Keep focusing on yourself - and don't like cater to him and such. Go out, let him know about when you'll be home and call if you'll be significantly late. Otherwise just do your thing.
