I am taking my children for their fourth time, my fifth. We are taking my dear friend Heny who helped us through my mom's passing last May. It is a celebration in effect as my mom sent me and the children a couple of times after my divorce, and I would like to remember her happily. She liked us to be there. Our friend has never been there at all; and I was advised to ask for a "It's my first time at WDW" pin for him at the first park we go to. Apparently, the cast members will be very kind and helpful to those brave enough to wear it. I never knew about this before or I would have obtained one for my children on their first trip. (Mind you, we aren't going to tell him this before we pin it on him.)
I am sure you will have a wonderful time, and really, everytime is like the first time.
have a great trip,
Donna