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I just installed brand new accelerator pumps with leather skirts. I was worried that they fit too loose. Within a few minutes they had swollen up to form a good seal, and they pump perfectly. if you subsequently remove them they are a bear to get back in with the skirts down straight. For a Stromberg 97, it is best to separate the plunger from the carburetor top to install them, and then wiggle the shaft through the hole in the top, without pulling the plunger up too high. If you mess it up they will bind and not pump right.
But to answer your question directly, oil is not needed, but can' hurt.