My wife & I have anal sex a couple times per year. We discovered early on that she likes external stimulation of her asshole and we do that all the time. One time, as I was rubbing the outside of her asshole, I slide my little finger up her ass. She went nuts, in a good way, with lots of moaning and pushing her ass against my finger. Fingering her ass became a regular part of our sex play and we progressed from my little finger to middle finger for finger fucking her ass. Of course we started talking about actual anal sex and together decided to give it a try. We used lube and took it slow and easy but she always experienced too much pain to relax and really enjoy it. She was willing to give it a try several times over a period of months but it never worked for her. We gave up on fucking her in the ass but continued the finger play. I was just happy she was willing to give it a try and how sexual she was in other ways. So how did we progress from not doing it to having anal sex a couple times per year? In a word, alcohol. Neither my wife nor I are heavy drinkers but we do enjoy some social drinking. From time to time, she will have a bit too much to drink and gets overly giddy, happy, and horny. This always leads to great sex. It was one of these times when she looked at me and said, "I want you to fuck me in the ass." Once again we used lube and I took it slow but this time she took me all in and we fucked with enthusiasm. I guess the alcohol let her totally relax her sphincter and enjoy the experience. We don't do it all the time but whenever she has one or two drinks too many she gets in the mood to have her ass fucked.
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