Well, here's mine then
EDIT: Sorry it's so long! The short version: After a 3200 mile trip my motorcycle boots caused me to lose permanent feeling in the skin on top of my big toes -_-
My riding boots are made of THICK leather. Over summer, in preparation of a 3200 mile trip to Sturgis at the end of summer, my husband and I went out riding every weekend (I sit on the back, and I'd never been on a motorcycle before). Each time they were uncomfortable, pinching my pinky toes and causing my feet to fall asleep. I'd have to get off the bike every 30 minutes to keep my feet happy and I do NOT have fussy feet. At first I attributed this to being a riding newb, because it's not uncommon and I really had no stamina. But as summer wore on and it didn't improve, I had to find ways to last longer on the bike, wiggling my feet, standing up while on the bike, changing how my feet sat on the pegs. It helped a little bit.
When we actually did the trip (about 6 days of pure riding in total), we would ride for about 1-1.5 hours before stopping. It was us on one bike, along with 3 friends each on their own bikes. The first day was HELLISH. I didn't want to be the slow person holding up the pace so I tried to last as absolutely long as possible before insisting that I had to take a break, and I had to take my boots off at almost every stop. I got tougher over the trip there, basically just working up stamina more than boots improving.
By the time we were headed back (about 2000 miles into the trip), I realized that even when I didn't have the boots on I couldn't feel my pinky toes, my big toes, or the skin on the side of my foot near the big toe (total surprise, those toes weren't bothering me at all). I could rub my finger over the skin and feel absolutely NOTHING in those parts of my feet. It was a bit freaky and a bit alarming, though it did make the boots much more comfortable heh.
The 2nd to last day we had to ride 650 miles in one day, took 14 hours and we had to take very short breaks. I learned my motorcycle stamina was now very high, and the boots had pretty much stopped bothering me. I could've lasted the additional 250 miles left to home if it wasn't so dark out (David would have been just fine, we've decided he's a Terminator).
So, the trip was in late August. The worst part: I STILL don't have full feeling back on top of my big toes (sad). I haven't put my riding boots on since then, but I have a feeling they're perfectly broken in now. Also seems to have helped my high heel wearing stamina, so I suppose it's not all bad.
EDIT: I also packed a pair of Keds-like shoes that were, apparently, a half size too small to wear for the 3 days while actually at Sturgis. They tore into the backs of my heels, giving me nasty blisters, and I had to seriously bandaid them up; made it very hard to walk anywhere and we had to walk a LOT. Had to deal with the aftermath of those shoes for the ride home in addition to all the problems with the boots.