I once went on a club ride and there was this nice looking gal (not smoking, but nice looking) with pretty big hips. Due to her hips being fairly wide, her shorts were stretched quite a bit. That, on top of the shorts being somewhat worn out (the edges were fraying a bit), made them quite see through; and she wasn't wearing panties...I'm positive on that one.
It was some what awkward riding behind her so I tried my best to either fall to the rear or speed up and hang in the front...but for some reason, I kept ending up right behind her...