one lesson i have learned the hard way is if you haven’t ridden 100 miles in a while you have to break your ass in by doing a few rides beforehand. my theory is that it builds up the layers of skin on your bum.
my theory is that the more you ride, the less you get tired on long rides and the more of your weight you’re able to put on your legs.
i’ve only done two 100+ mile days. they were back to back, and my backside hurt with the seriousness after the second day. my conclusion was that it was cuz of the boxers i wore. they were nice and soft and stretchy cotton, but they didn’t wick a damn, and chafed the heck out of me. i’ve gone to bike shorts and haven’t looked back. and haven’t had to.