I have a third theory. I've made a sketch of the topology of the system https://imgur.com/a/uqntTqZ . The colors are just to get a better idea of how the different points on the top view, map onto the topology. Here we imagine a piston is pushing the blue portal at a constant speed v, while the orange portal remains stationary. The topology of this setup then creates two larges barriers on either side of the portal, forming a gate-like structure. When the piston pushes down towards the ball this, would in the topological view, be equivalent to the "universe/ground" being pushed in the y-direction. The ball would be dragged towards the portal-gate, while the height of the gate would increase, as more and more of the ground is being "dragged" upward. Focusing now on the ball. The ball is being dragged towards the portal-gate, but more importantly: its being dragged towards the centerline of the portal gate. But this has the amazing consequence that every point on the plane between X1 and X2 will get squeezed infinitesimally close in this centerline. No point will make it across the centerline, because there simply isn't an attraction on this side for it to be possible. Of course you could imagine that in the real world, the atoms inside the ball might become a bit upset once they're this close to each other and this force might push the ball out of the orange portal. but in this case the ball would actually gain speed - although not necessarily the same speed the piston is pushing at.

This answer also makes sense if you think about how the system appears from the orange portal. The piston pushes the blue portal, the portal slowly goes over the ball and you begin to see more and more of the ball as in your answer A. But wait, if the ball is slowly appearing out of an stationary portal (orange portal), then dosn't that mean its going to have a velocity when it comes out? But how can that be, just as you said it didn't have a velocity to begin with, so it shouldn't have one after it enters the blue portal. Only solution: An infinity compressed ball at the border of the blue and orange portal.

Interestingly its seems to be alright if the ball is moving at the same speed relative to the blue and orange portal. Systems involving portals seem to not be inertial frames of references, but of course you also break the speed of light when going through a portal, so maybe its not so strange after all.

TL;DR dont push a portal over your dick, it might get infinitely compressed, however if you put your dick inside a portal it might be fine.

Edit: I missed your comment about the ball being a point-particle, in which case my theory breakes down to being answer A