Tip #2: Vibrators

Tip #2: Lube, lube, lubeThe vagina produces it's own lubricant.

The anus does not. Therefore, you need to supply the lube, one way or another. On top of that, using a lot of lube is good and using even more lube is better. It makes the whole experience much more pleasant, for both partners. This is the number one mistake people make in having anal sex: not enough lube.

All kinds of lube are used for anal sex, from spit to Vaseline to high-tech silicone-based lubes.
We'd strongly recommend spending a little money to get a high quality water-based lubricant; remember, an oil-based lubricant like Vaseline will degrade the latex in a condom, destroying its usefulness. We'd recommend products like AstroGlide , available in any drug store.

Note, though a condom may be "lubricated", they typically don't offer as much lube as we'd recommend for anal sex.We don't recommend specialty lubes designed for anal sex that include an anesthetic to numb the woman's sensation.

Anal sex isn't supposed to be painful. If it's painful, you need to figure out what's wrong, not mask the pain with a topical anesthetic.