Lots of lube, and maybe practice on yourself too.

Everyone always says use more lube. What if that's not the problem though? What if he used a whole bottle of lube and she still feels uncomfortable and it still "kinda hurts?"

@ 2 - Then it's because she's stressed out. So the other parts of Dan's advice apply.

I still find some fingers bony and uncomfortable after 30 years at it. Your boyfriend needs to practise on himself until he gets what it feels like.

@2 - Try two bottles of lube.

@ 2 - And by "using a whole bottle of lube", we don't mean as an insertive toy. We mean using its contents.

She didn't say anything about lube, which suggests that her discomfort MIGHT have been 100% avoidable from the get-go.

If she's learned that their are great benefits to anal stimulation, she should get a lot of encouragement to explore on her own. When the territory isn't so unfamiliar, she might enjoy things other than fingers...

I wonder how much of her discomfort is the straight girl "OMG I'm letting him finger my butthole" shame. Relax girly, everyone plays with their booties. It's all in good fun but make sure he washes his hands first and keeps his nails short.

"Tell him to find some other way of getting me to that point again"?????

How about owning your own body, your own sexuality and your own climaxes, Missy?

(Also, I had no idea that Mr Savage is sufficiently flexible to be able to see NINE fingers when one is engaged instage, as it were. At his age, that's not bad.)

@6, NOW you tell me.

So why all of the reruns? Does Savage not do the SLLOTD anymore at all? Are the letters not coming in? Is this a second-stab at answering for him? Did I miss the explanation long ago?

You haven't seen the rash (no pun intended) of butthole accidents in the news? He's probably running this classic as a public service.

*silicon* lube! And pick up a copy of Tristan Taoromino's Guide to Anal Sex for Women.

@13 Great book! I read it a couple of times. The guy's face behind the register when I bought it was pretty awesome as well.

Silicon lube is great...until you try to clean up. That stuff is damn near impossible to get off in the shower.

@ Allyn, Dan seems to be traveling a lot more these days—the newest thing is the HUMP Tour, on top of the lectures, media appearances, family vacations, taping Lovecasts, doing the weekly columns, keeping tabs on spinoff websites, and whatever he's got cooking in the book & TV areas. He does do fresh SLLOTDs for several days at a time, seemingly worked around his trips. More an opportunity for us to have a second go at answering, and discussion sometimes goes in different directions.

I get tired just thinking about all the balls he keeps in the air (ha), and especially thinking about all the airport/taxi/hotel time.

No one ever seems to mention this, so I will: Some people find that having something small, like a finger, in their ass is actually more uncomfortable and annoying than something larger, like a butt plug or a penis.

Who the hell can see anyone's other fingers when their partner's fingering their booty-hole? Are they detachable or something? Or is her brown eye actually an eye?

Make sure any finger going into your butt has been trimmed and everything buffed/sanded smooth. Even a tiny callous or hangnail can really hurt such a tender and sensitive area.