It may be possible that oil is getting in the air filter and then the air turbulence caused from riding may work the oil around to the front of the cylinder.
It doesn't look as if the cylinder base gasket is leaking and it is hard to tell if the rocker box or rocker cover gasket is leaking.
Just for the heck of it pull the air filter and see if there is oil in it.
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08 FLTR candy red sunglo,with 2015 103 HO, V&H Dresser Duals with Monster Rounds, Power Vision tuner, Willy Shiny Wheels and Forks and a bunch of other stuff.