Does anal sex hurt?
Anal sex should be comfortable and pleasurable. There may be initial pain or discomfort when an erect penis enters though that usually passes quickly and can be avoided by relaxing properly first with slow, deep breathing.
Both you and your partner need to be well lubricated and your partner must wear a condom.
If there is any blood, excessive discomfort or pain or if you are simply not enjoying the experience you should stop.
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We are not doctors. 
