The first time I had Anal was with my current girlfriend. She asked for it, she had it once before she said it hurt but it felt kind of good. When we did it for the first time we use sooo much lube, it was new experience for me, it’s really something different. She loved it and it didn’t hurt at all, not even a little. Now it’s part of our sex life. If you want it to become part of your sex life I suggest you get some anal toys. It really feels amazing fucking your woman with an anal toy in her ass. It gives her much stronger orgasms, especially if she more clitoral than virginal. Get something small to start with and then wait until she asks for something bigger. And you can be sure that she will.