How do I persuade my girl to do anal?

There is so much wrong with this question. First off, why would you want to persuade someone to do something they don't want to do? So let's rephrase this question based on the fact that there is no point whatsoever in having any kind of sex with someone who isn't just as hot for that sex as you are.

I am curious about anal sex.. how can I make this seem enjoyable and fun so that my girlfriend will be willing to experiment with me?

Well ok, that's a little bit better.

First you have to understand that I, in general, do not like anal sex. I have had a few good experiences with it, many negative experiences, and just in general... I prefer to play with my pussy. However I will say that despite my ass's best efforts at forcing me away from all things anal forever and ever, my brain still finds it incredibly erotic. It's making my pussy throb right now just writing about it.

I really, really recommend that you go to puckerup.com, which is Tristan Taormino's site. Read everything there. Buy her book. Seriously! She is the undisputed Queen of anal sex and she knows more in one pinky about the ass than I could ever hope to tell you. There is no one else in the universe who I think has studied the ass in as much depth as Tristan. Plus, she's totally fucking hot. :)

Meanwhile if you want to start doing a little bit of mild anal play... you need to understand that turtles really do win this race, while hares are going to get themselves tossed out of the bed altogether. I'm a tightass, try to ram your cock in there and you'll hurt yourself (imagine ramming your cock against a brick wall), you'll hurt me, PLUS you'll piss me off. So seriously, please, don't even think about it. Start slow. No, even slower than that.

You might consider gently... GENTLY... stroking her asshole with your finger while you go down on her. If she freaks out, stop. If she doesn't, keep stroking... GENTLY... until she cums, then stop, and leave it alone.

If she freaked out when you tried that, you'll hafta start by discussing it with her. And if she just says HELL NO, get Tristan's book and read it together. One of the most important things though, is that she needs to always feel like she is in control. She needs to know that you will never push past what she is comfortable with and that she can tell you to stop at ANY time without your being upset. Don't ever push, cajole, whine, whimper, beg, plead, or otherwise try to coerce her. Accept what she says and move on.

IF she is game and likes the finger stroking bit, do that several times... with *lots* of oral and clit stimulation... make her associate it with cumming. Then you might *slowly* try to introduce small toys, or lubed up fingers, into the equation. The key is lots and lots and lots and lots of lube.

I think that's enough to start... I'll save the rest for my intermediate anal play advice. :)

Good luck!