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This all sounds pretty normal to me. The first pass of the dilator is always the hardest. You might find that this size will always be a struggle, until you move up to the next size. Once you start using the largest size in the set, this second largest size should be a lot easier to insert.

We often recommend dilating immediately prior to intercourse, and that is helpful because the dilator can break that initial resistance, and then the penis will have an easier time to penetrate.