I would never recommend lapping a piston into a liner. On all my engine builds the liner is lapped first, then the piston lapped to fit. The means a liner lap and a piston lap. If you think about it, the fits we require in these engines is VERY close, in the 100 thousanths or even millionths of an inch clearance regions. Consider the size of a 1000 grit particle, its about .0004 inches (1500 is a bit smaller) that times 2 is .0008 inches, nearly a thousandth of an inch. What we want is about a decimal point further to the left! In order to get the piston to move in the liner with lapping compound in it and feel "just right" you've already made the piston undersize. The seal you had was the oil in the peaks of the surface finish and with very little running the peaks were worn away and could no longer hold any oil, your fit was gone. Typically lapped engines are fitted tightly so that as they are run the piston and liner wall "seat" together, this cannot be accomplished if they are lapped one to the other, they will always break in to a looser then desired fit. Further, well done fits are tapered, liner tighter at the top then the bottom and piston larger at the crown then the skirt. This does 2 things, it accounts to some degree for the thermal expansion of the liner which is hotter at the top then at the bottom and with the piston it minimizes the skirt friction that does nothing but sap power. A piston and cylinder lapped together will lack both of these very desirable characteristics. They will conform one to the other and the total surface area of the piston circumference will contact the liner, if the liner is tapered in the wrong direction due to wear it gets looser at the top rather then tighter and you will not be able to maintain compression.
Flame suit on.