Hank, I agree 100%. Take cues from the woman you are dating. It can feel like a strange balancing act "Do I talk aabout IT?" "Do I ignore IT?" "What if I want to touch IT?" Thankfully most Transwomen are aware of the delema and have enough understanding of men to know that direct communication wins over sublte hints every time.
I also did mean to imply that a guy should ignore a Transwoman's "male" past. Hell, I did some awesome stuff as a guy that I'd love to share with a potential boyfriend. It is just rude to press for that information on a first date.