Bought my '10 Fat Bob (Black Screamin Eagle Pipes & Stage 1 Air) in June and currently have about 1,800 miles on it. For some time, it has had trouble starting when hot. Not every time, but once in a while, after refueling I would go to start up and it would turn but not actually start. I would let it sit for just a few seconds and it would start right up like nothing was wrong.
Today, however, I went to start it after having let it sit in the garage for 2 weeks following an 800 mile ride through 100+ degree heat. When I hit the starter, it turned over a couple times then "clanked" to a stop, nothing else. I tried to start it again after just a second and it started fine. I noticed some lightly gray tinted water was spraying out of the lower exhaust pipe, and when I got home I noticed a bunch of small black flakes on the ground behind where the pipes were. Bike seems to run like normal, although it "seems" that the cluth lever is loose, but I could just be being over-sensitive on that. Only issue is it not starting on first try but firing right up on the second. Ideas?

 

Try starting it by switching the" ignition" on then the "run" then immediately hit the start. Why wait for the pump to pump? don't do that for the auto do you?
See what happens.