Can You Suggest Some Ways I Can Be More Of A Challenge?

My super-attractive and successful boyfriend and I have been together 6 months. We’re long distance, and I’ve been so afraid of him losing interest, that I’ve put a great deal of work into initiating contact, (every other day I text him first – flirty messages or sincere appreciation for something he has helped me with) asking him for a shirt of his to wear to bed, complimenting him, etc. We’re both older (42 and 34), and he’s always telling me how great I am, but that I do not give myself enough credit. He has been chatting with other women lately – I found him on the site where we met because my counselor told me he shows signs of a cheating guy, and suggested I look online. I confronted him, and he said he is talking to 3 girls in 3 states but that he hasn’t met them. I suggested we have the option to see other people if we want- I think he’s doing it anyway, so he agreed.
He keeps hinting that he likes to “earn” someone’s affection, and that I need to EXPECT that he wants to stay with me, only have eyes for me, and that he will treat me well.
I finally see now what he’s saying. Basically, he’s saying that all the things he thinks are so great about me are diminished by my low self-confidence.
So… How can I be more challenging to him? How do I show him that I EXPECT him to come to see me, to call me? He never initiates coming to see me. He always says for me to let him know when I want to see him again and he will make it happen, which is very confusing to me…