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You have to take your time, or you'll ruin it for her forever. Just go slow, start with one finger, then two, let it loosen. Lick her pussy while you finger her ass- lube is mandatory, and then slowly work the head in, don't try to force it to the hilt right away, just work it and you'll be pumpin it hard in no time. Rub her clit at the same time (or tell her to touch it herself) and it's virtually a guaranteed orgasm for her.
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