The Largest Misconceptions of Anal Intercourse has an article about anal intercourse, particularly for newcomers.

Much of the advice can be found at many other sites, but one of the most important sections is this:

Most people believe that anal intercourse hurts and that it is always an uncomfortable experience. This is quite simply false. As with any form of intercourse, the anus, like the vagina, must become used to the activity. Any woman who remembers her first time having sex probably recalls a painful experience. In fact, the first couple of times were probably painful and not that enjoyable. Did they stop having sex? In almost all cases, they didn’t. Anal intercourse falls under the same guidelines for both genders; it takes practice to get accustomed to the activity.

This needs to be repeated and understood and communicated to a wider audience, for the ‘hurt factor’ is often cited as a reason not to do anal.

As one man replies:

She didn’t think it was gonna be fun. Yea that was one time a long long time ago. Convinced her that I really like anal, had it a few times before, and that those girls loved it once they got over the fear.
She was really hesitant, but she knew I wanted it. We followed all the tips, especially pushing out when I started pushing in.
She loved it, in fact anal is now our go to. For us, vaginal is like the foreplay with anal being were we finish.
We like HQ Olive Oil as lube. Damn good stuff and coats it all real good.
She wishes now that she didn’t put up such a big fight then, but is so thankful that she tried it for me.

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