There are a lot of negative associations with anal sex. Some of these have to do with homophobia and the association of anal sex with gay men. Some have to do with our culture's discomfort with the anus. Some have to do with the assumption that anal sex hurts.
No sex play should ever hurt! That includes anal sex. But any type of sex can feel uncomfortable if you don't do it right.
Here are some tips to make sure that anal sex is pleasurable for both partners.
Never do anything that you are not comfortable with! If you are feeling pressured into any type of sexual situation, your body is more likely to be tense. This can lead to discomfort.
Don't begin sex play begin by inserting something into the anus. Try some other forms of foreplay first.
Make sure to use plenty of artificial lubricant. Unlike the vagina, the anus does not produce sufficient lube for sex play, and in this case, wetter is better. Lubes like Maxxim and Anal Eze are good bets in this department.
Go slow! Wait for the body to relax before continuing. Never force a penis or other object into the anus.
Don't be afraid to speak up. If something is uncomfortable or hurts, tell your partner and hold off on anal play until what you are doing feels better.
And of course, practice safer sex by using a condom