What is your goal here?
I can't imagine tires pushing harder on the ground due to deformation from speed- it is the mass of the vehicle pushing on the ground and if we ignore aero lift or downforce (as it is a variable independent of tires) that mass should be the sole determinant of how hard the tires push against the ground (assuming, of course, a straight and level road condition).
As far as a tire getting a pointed shape, I think the tire would blow up first due to centrifugal forces beyond it's design and construction limits, and it'd be going a hella lot faster than it's speed rating, especially if we are talking about steel belted radials which just about all cars and trucks have now.
But let's assume it does that. The friction which causes rolling resistance, as I understand it, mostly comes from the hysteresis or energy loss from flexing rubber, and most of that loss is in the tread region of the tire followed by the sidewalls. If we're flying along at 1000 mph such that the centrifugal force on the tires is making them pointy, they probably won't be flexing very much at the point of road contact so yes I suppose there could be less r.r.. But that situation doesn't exist on the street, that I know of. LSR cars don't even have rubber tires that I know of. Dragster tires do lots of funny things with speed and centrifugal force so that might be kind of along the lines of what you are thinking.
If you're in a Tempo which generates so much aero lift that it's about to go airborne (LOOK OUT HERMIE LOOK OUT!!!
) I suppose since the loading on the tire has been reduced to near nothing, that the tread and sidewall flexing has been reduced too, thus lowering rolling resistance.