Untermenshe is right that Bob, walking a finite speed, will never reach infinite, and thus could not be at his "infinitieth" step in the present if he were only walking a finite amount of time from the negatives.
You won't ever reach the "end of the naturals", there isn't one. It's like you'll never find the smallest finite unit of time- there isn't one.
Traveling from 1 to 2 on the number line requires one to traverse an infinite amount of points.
Between location A and different location B in spacetime, there are an infinite amount of locations (spacetime is smooth/continuous). There is 10% of the distance from A to B, 1% of the distance, .1% of the distance, .01% of the distance......
If you take a finite step, you have traversed an infinite amount of locations in spacetime- every single location between the start of and end of your step has been traversed.
Likewise from one moment in time to the next- there are always an infinite amount of moments in any finite amount of time.