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To date, I've greased every piston head that I assemble with plain old white lithium grease, after doing what Stalker describes in stretching the o-ring.
About 80-90% of the time I find that the o-rings are either stuck in the piston head or very stiff straight from the packaging. On some, I'll pull the o-ring right off and "massage" it to loosen it up. Comparing it's "fresh from the package" size to it's post-conditioning size, it's no surprise how much air compression will be lost if you don't do that.
On really stubborn ones, I'll just swap the o-ring altogether. It's only a couple of bucks for a bunch of them at the hardware store.
Too much grease and it'll get blown either out the barrel (which doesn't do great things for your hopup) or pack up in the piston head.
I've never used silicone oil for the piston head...I've always though that an very thin coating of grease on the cylinder walls and a greased piston head o-ring was the way to go.
Anyways...just what I do, it's always good to hear what others do.
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