Tiny hole; how can i ease her up without too much pain?

My lover has a very small hole, and she has recently become interested in anal. It's kind of a funny story how it happened, but i won't go there.

Her's is so small, there's not even a visual opening, and she wants to be able to experience anal sex, but I can hardly fit my middle finger in, and my penis is more than three fingers width(not trying to give myself an ego boost, or show off, I just want advice). What should I start her out with, a thin dildo, or just work more and more fingers in? Also, when is it okay to switch to the penis?

I feel sort of bad, as I enjoy anally pleasing myself quite a bit, and can fit almost a penis' width into myself, so I only know what I can do, but not her.

Any helpful advice would be greatly appreciated!

 

I think you should tell the funny story of how she got interested.

 

Seconded!:agree: lol.

 

thirded, lol

 

I don't think you're gettin' any help 'till you tell the story....

 

USE different size but plugs. and LUBE!! anal ease. Also TELL THE DAMN STORY!!!!!!!!!!!!!