My first time was for an organized trail ride while on vacation (gotta have the horse fix!). I was the most experienced rider, so I rode Bud, a huge draft with an equally huge western saddle (I was around 5'3" at the time) :P When I got on I thought my hips were going to literately pop off! However, once the pain subsided I had a good ride.
My first was on my honeymoon! It was my favorite part of the trip-- when they walked him out of the barn I crossed my fingers and hoped! It was so awesome to look down and see those giant feet trotting under me!!
If he wasn't all the way in Niagara Falls, I'd tell them I want to buy him! He was awesome.