I'm not sure how serious the questions were, but having spent must of the last year with half an eye on home-schooling duties, I'm going to try a serious answer.
Here's a representation of one set of bends:
ACD (straight) or ABD (wavy).
Answer 1: It's pretty obvious that ABD is longer than ACD, and if you plug in some numbers you can work out how much longer.
It won't be much, because the width of the road is a limiting factor at how far the paths of the cyclists can diverge.
Also, for one cyclist to be able to cycle a straight line constrains how much the road can bend.
I doubt the difference would be more than 1%; but I'm not sure exactly what kind of road you're imagining.
Answer 2: No, GPS measurements will not be identical.
They are sensitive enough to show which side of the road you're on; perhaps not reliably, but it should be clear which rider is hugging the kerb.
However, GPS only takes periodic measurement of position, to the wave line will in theory resolve to jagged triangle like my diagram.