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When a finger, object or penis is intorduced into the anus, the anal muscles go into spasm, as if fighting off an invasion. Pain will result if the partners do not wait for these muscles to relax. Under sufficient stress they will eventually collapse and the pain subside, unless further damage is done. But, any 'pleasure' afforded from this kind of activity derives mostly from the absence of discomfort.
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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.