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Start with a well-lubricated finger or a slim (smaller than your penis) dildo. The dildo is more realistic, but your fingers can flex and feel what they're doing inside her ass. Slide one finger in slowly, letting her adjust to it. Take your finger all the way out, then push it back in again. Give her anus time to get used to this kind of activity. Then slide a second finger in. Consider how big your penis is and realize that two fingers is probably enough.
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