Yes, but will put a lot of pressure on your insulation in your transformer... try to avoid this situation if possible... or put a resistor across the output ( 500R) to keep the peak volts down, and stop the chance of interwinding shorts in the tranny.... it shouldn't... but don't tempt it either.
I use plan B in your question above, as the potential between wires is the least where the layer wires transit to the next layer
Dario, for battery electric fences, power drain is a significant problem with the design, I had not thought at all about power drain with the ac model, as keeping animals in is more important than power cost.. any cost.....
But a battery needs consideration, so you must be more attune to economy.. if you want to do dc, then suggest you go with the dc version, very very much less power required from the battery
.............oztules