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Definitely use good, non-toxic lube. Suggest she "go #2" sometime before you try it. This is a sexual act that should be discussed.
This isn't a time to go "whoops, it just slipped in."
Another word: patience. Remember, unless you had an instinct for sex, you were not very good at sex nor going down on her/him the first time.
Start slowly. One finger the first session...and slowly progress. This is just like dating as a kid - you have to get to each base, a slow progression, before "scoring."
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