Hi Max. I am going to answer out of order here...Yes, I have had an issue or two with discomfort when dealing with a cock that bends one direction or the other. Generally speaking, it has happened when either he or I moved unexpectedly.
As for a position most likely to help her reach orgasm, try reverse cowgirl. In this sexual position, the female mounts the male, but facing his feet instead of his face. The reason I think this would be the best option for you and your girlfriend is simple: with a cock that curves down, reverse cowgirl increases the likelihood of hitting her g-spot.
Example of reverse cowgirl:

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