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I remember when I broached the topic of anal with my wife (who was a little prudish to say the least at the time). She was a little worried, but slowly over the past 2 years I found that she got to appreciate more and more the sensation of pressure around that area. For a treat one night she asked if I wanted to try it all the way and aside from having a hard time maintaining an erection because I was worried about hurting her, everything went well.
I started preparing her for this awhile back by slipping my hand under her butt and massaging her taint with my finger while I gave her an clitorial orgasm with my other hand.
That seemed to give her a more powerful orgasm, so I tried inserting a finger in her ass just before her climax. I couldn't do more than 2 fingers because I'm just not that flexible and it hurt my hand because when she climaxes, her ass squeezes around my fingers really tight.
Things work better when your partner associates anal sex as something that will be pleasurable, rather than something that *may* hurt. Just work up to it. Sometimes don;t penetrate, just run your finger around the outside.
One thing that really helped me was that once I shaved her anal area to make it all slick and then proceeded to tongue her. When she spread her cheeks for me, I knew that she enjoyed it, but I also paid attention to her to make it enjoyable.
We have never used lube, just spit, but I think that is because I spend a long time before I get to that.
I was surprised the last time we did it because she was actually pushing against me to get it in. Women say the wildest things when they want to orgasm. later on, she said she liked the feeling of being full and asked me what I liked about it.
My response was that it feels like your getting a handjob from someone wearing a velvet glove that has been dipped in hot oil.
That's been my experience, your actual mileage may vary.
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