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UPDATE: Well after a fair bit of struggling with the cylinder and the the largest ring, I finally got it on with the help of a bit of lube. But after pumping it was a struggle to get my penis removed from the cylinder. Anyway, lesson learned: for me at least, don't use a cylinder ring...

they are simply too big. I'm afraid to exert too much pressure to push them on out of fear of breaking the cylinder. Any idease?