Nice thread.

My group recently escorted an air-convoy on our flying mounts. We actually suggested air travel to get there faster and avoid unnecessary trouble.
Consequently, a red dragon showed up for a feast, and while most of the party tries to safely land our protegee, my acrobatic fighter/rogue tries to attack the dragon.
Unsurprisingly, with no ranks in handle animal, and about 2 in ride, I can hardly reach the dragon in mid-flight. So...
Screw this, I think, if I get ON the dragon, my balance skill can keep me there for quite a while, while I'm only exposed to the dragons head.
Of course, I fail my ride-check to get into a suitable position to jump.
Screw this!
My jump works, barely, but I don't make the balance-check (it was a 2 or something) to hold on, and start to fall. I asked if I could ram one of my swords into the dragon, to stop my fall. It works and I get to hold on to my life for a bit longer.
Seeing that I can't evade him now, the dragon turns his head an roasts me.

Somehow, my PC survived the fight, even taking the beast down in the end.