Acctually, I wore mine like 3 times and then rode in them and riding broke them down so much! We were jumping too. Are they the Heritage II? That is what I have and it is PAINFUL lol you'll live though! No pain no gain!
Get a leather conditioner and treat them a couple times and wear them riding. I have a pair of Ariat Challenger field boots and after about 20 minutes of riding I forgot they were there and I love wearing them.
Well, its nice to hear that they are comfy now but if you ever need to brake in a pair of boots again, and you don't want to be wearing them around the house you can put a hockey puck in both your boots for several hours.