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Just because your partner is interested in anal sex doesn't mean that you have to be interested too. Trying a small anal plug can get your body used to the sensation of fullness and let you determine whether or not it's pleasurable for you.
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There is no straight answer for this. We used Vaseline, but my boyfriend later realized that it deadens sensation on the skin, which was obviously helpful for my asshole but bad for his orgasm.
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