The shaft of the penis isn't as sensitive as the head. I've occasionally plucked hairs just for the hell of it, and it doesn't hurt much at all, if any(depends on the hair). So plucking or waxing may not be quite the horrible ordeal you imagine it to be.
He could shave the area, but he would have to do it frequently to prevent stubble. Hopefully he would be willing to do so to prevent you being in pain.
And as rsl12 said, if you haven't tried lubes, use them. If KY or vaseline is too thick, try Astroglide, its thinner, but still does a good job.
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