Tip Lube, lube, lube One of the most important thing to remember when thinking about anal sex is that, unlike the vagina, the anus isn't self-lubricating: you gotta bring your own grease. And, the more lube you use, the better. It will make the initial penetration much more easy and less painful for the woman and make the whole experience, for both of you, much more pleasant. The most common suggestion we get from our readers is to use LOTS of lube; we just can't emphasize this point enough. Enjoy in anal sex:)