A.J.710, I think the physical picture here is most intuitive of looked at in terms of energy (Disclaimer: I am not expert but have had dealings with problems like these in my own inventions).
The water in your bucket has a certain lot of energy that can be ascribed to it that is divided between kinetic energy (gross translation or movement -- speed), pressure-volume energy (due to its state and form -- takes energy to compress water vapour to liquid, energy consumed to evaporate etc.), and potential energy due to the water's elevation. These latter two entities make up the piezometric head -- which is reflected as gauge pressure (take a look at Bernoulli's equation, to make things clearer).
Now, standing on your circle will compress the water underneath you by your weight divided by the area of the circle, i.e. if you have a 200 square inch circle then you are only contributing 1 PSI to the pressure of the water. At the exiting outlet the pressure inside the bucket will then be that due to you standing on it, the atmospheric pressure pressing down upon it from above, and due to the weight of the water above the outlet. Outside the outlet the pressure is only that supplied by the atmosphere. Now, assuming the outlet is at a set elevation, there clearly is a difference in internal and external pressure. Water will thus be accelerated out of the bucket, and adopt the pressure outside. The surplus energy due to overpressure will be converted into kinetic energy as the water exits, which answers your questions as to why pressing harder causes a more vigorous flow of water to be expelled (as far as I know we can generally say and increase in velocity is accompanied by a drop in pressure if we are not adding energy to a fluid -- this is the idea behind the venturi tube and airplane wind, in the latter case we guide the air above the wing over a longer course than that below the wing, so it must be moving at a higher velocity, and hence we create a depression above the wing that keeps the airplane aloft).
Really what is happening is the water is transferring the energy stored in your elevated mass into kinetic energy of the water, with the pressure-volume energy of the water being the intermediate.
I hope my common-man's approach has been helpful, and am open to questions if you have any more. Also open to additions from our better informed peers, as I may be wrong.
Cheers