Once the O-ring hits the sidewall, motion relative to the groove stops, and you only need consider friction on the other side (I think you know that already).
As far as any additional squeeze (and increased friction) occurring due to the deformation of the O-ring, you are now in the realm where you'll have to just make some assumptions, and go test. The amount of deformation of the ring will depend on the compound, pressure differential, temperature, fluids used, friction developed (note the recursion here), velocity of travel, etc. etc. etc. The Parker handbook reference shows a little bit of data, but it's pretty limited, and not much use if you aren't using the specific compounds they show data for. Good luck.