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The real trick is for the person who is catching, I assume her, to get control of their sphincters; there are two to worry about. Until she does that, it will hurt a bit no matter how much lube. Most of the advice has been to go easy at first, building the size of insertion, and that's the retail method of giving her control of the sphincters unconsciously. If she were to actually work by herself or with your help to get conscious control over them (the outer one is easy, the inner a bitch) then 1) She'll enjoy it a lot more, 2) You won't have to use so much lube, 3) you won't have so much prep time, and 4) she'll never have problems with hemorrhoids or constipation.
Shoot for no pain ever.
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Light a man a fire, and he will be warm while it burns.
Set a man on fire, and he will be warm for the rest of his life.
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