Brakes question

[Dead Eye]

If pumping returns the pressure then I'd suggest a slow leak? When the fluid is under pressure its leaking out and as that happens the pressure drops and stops the leak. The result is very soft brakes on the first pull, which forces more pressure into the hoses. Second squeeze is much better because the first squeeze has increased the pressure, but the leak is likely back again and you'll notice its soft again if you don't touch the brakes for a while.

An alternative could be the master cylinder - not sure how possible it is, but maybe its busted and is letting fluid back in to the reservoir (failed valve) This would cause exactly the same symptoms as described above but without the leak - or just consider it a "leak" back through to the reservoir

I can't think of anything else off-hand...