I am a 27-year-old hetero female. My new boyfriend is 24 and kinky. Before I met him, I had never been bound or spanked or had any kind of sex that was not “vanilla.” I have enjoyed everything we have done and I trust him. Now he wants anal sex. He has what I think is an average dick—based on the three others I’ve seen—but I’m afraid that it will be painful. Am I a big baby?
Another Needing Anal Lessons

I order you to start having anal sex with your boyfriend immediately, ANAL. Tons of anal—but without letting your boyfriend’s cock come anywhere near your ass, ‘kay?

In other words: yes to anal, no to dick. Think tongues, lubed-up fingers, very small toys, and smooth, clean vibrators used non-insertively (which is fancy sex-advice talk for “lay the vibrator on your asshole, don’t shove it the fuck in”). If you find that you enjoy other kinds of anal sex—and you will—your boyfriend’s dick may start to look like a shiny new toy, or an enticing upgrade, and not the intimidating asshammer that it appears to be now.

But for this to work, your boyfriend has to swear on a stack of Jack Morin’s Anal and Pleasure & Healths that he will pleasure your ass, and get you off, without attempting to rush you or pressure you into dick-in-ass buttfucking until you decide you’re ready.

http://www.thestranger.com/seattle/SavageLove?oid=680268

Good luck John!

Wrong. The anus has one of the highest concentrations of nerve endings anywhere on the body. You know how good it feels when you take a big shit? Imagine that, but in reverse. DIVINE!

“Simply put, the anus is not an erogenous zone on women. Men have prostates that make anal sex pleasurable, but women have nada, zilch in the area (anything good, that is).”

Actually, the anus itself has more nerve endings than almost any area of the body other than the genitals. Next time you’re going down on your bf or gf, give it a little lick and you’ll see what I mean–it can feel pretty fucking amazing. Also, in women, the rectum shares a wall with the vagina (check it out: http://en.wikipedia.org/wiki/Female_reproductive_system), which is why some women report being able to orgasm from anal sex alone.

Other than that, looks like pretty sound advice (though his question was a little ambiguous… are you sure he wasn’t looking for a way to convince her to give it to HIM up the butt… that’s what I read at first haha)

Literally.