Start with cunnilingus...and a finger
The very very best way to go about anal is to begin orally: for me at least, a finger in the ass makes cunnilingus about a million percent more enjoyable. a few orgasms into the session, another finger can be added. a few minutes of this, and you'll be practically begging for anal sex... and you'll be both physically prepped and mentally ready for it.
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.
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