Hi etherist, A piston won't seal against a cylinder simply by being close fitting. There will always be a gap between the piston and cylinder which allows some leakage. If there isn't, the piston will rub on the cylinder, create heat, wear, etc...
Seals function because the contact stress between the sealing faces is higher than the pressure differential, so without this contact stress, you won't form a seal. You can limit the leakage and that leakage can be calculated by modeling the gap between your piston and cylinder but it will leak nevertheless as long as there's a gap.