Ok, I think I'm finally starting to figure this out.

When I'm ordered to start the descent (from FL380) I'm at cruise speed (.85 mach) with speed hold on. The speed hold reduces power to maintain the speed, but that's maintaining .85 mach. Instead I need to disengage speed hold, pull the throttles to idle, and then start the descent. That's what you're saying right?
Big learning curve for me, the last flying game I played was B-17 Flying Fortress (or was it Aces Over Europe?).