The flow of the discussion from my point of view was that he said yes he was open to it only if it felt natural. That's why I asked if he could a least try. It was his "Here we go" reply that changed the tone of the conversation. Had he said, "Yes, it's off the table", I would have let go of the cum talk. I felt my line of questioning has irritated him so I apologized for that.
From his ad, I could sense him as someone who would talk through things. That was my mistake.