and we know that objects with more mass fall
faster in air.
That is not necessarily the case. For two independently falling objects, the object subjected to the greater net force (force of gravity minus the opposing air drag force) will have the greater acceleration.
The mass of the object determines the force of gravity acting down on the object. But the shape and surface characteristics of the object, which is independent of the mass, determines the opposing air drag force.
But the example you have given does not involve independently falling objects. Assuming one object is above the other, then logically the only way one object can accelerate more quickly is if it's the lower object. And the only way that can happen is if the net force acting on the lower object is greater than the net force acting on the upper object.
Complicating matters is that the drag force acting on the upper object depends on the degree to which its surface area is blocked from air resistance by the lower object. And that will change if and when the objects begin separating. Moreover, prior to the objects separating, if in fact they do, both objects will experience some portion of the applied pushing force. If separation does occur, then only the upper object will experience the pushing force.
Bottom line, without additional details regarding the two objects and their arrangement, there are too many variables in your example to determine whether or not the lower object will accelerate faster than the upper object.
Hope this helps.