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When you give the woman a lot of foreplay (I really mean a whole hell of a lot of foreplay) then she's less likely to feel pain---especially if you've given her oral sex and made her climax first.
Depending on the woman you can penetrate her without even using lube, but your best bet is to lubricate her anus and your penis because the anus and rectum are not naturally self-lubricating structures and are very sensitive.
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Doncalypso... the one and only Haitian Sensation
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