I'm so sorry, I know how confusing this is for you and how could it not be? The type of "friendship" you describe sound like romance, feels like romance, and acts like romance but he's very clear to make a distinction that there is no romance. Who benefits? You who have an emotional stake in this game or he who is just having a good time?

To me it sounds like manipulation, feels like manipulation and acts like manipulation. Perhaps I'm cynical, but I think he figures if he can keep making you bend more than you're ready for eventually you'll break. You're a challange and he wants to keep you in play until he's through. Continue with this "friendship" carefully, I would really hate to see you get hurt anymore that you already have been. IMO a man with honor would have respected your boundaries long before now, once his toe hit the line he should have made sure he never entered the red zone again.