Huge amounts of foreplay including normal vaginal sex, then plenty of lube.
Did you ever consider that the woman might like the sensation and be capable climaxing through anal sex?
Personally I think there's less sensation (not as intense) having anal sex but if your woman suggests it, would you refuse?
Also curiosity!
I had an escort call to my hotel about 3yrs ago Anal was included in the price, when I asked her to get into position for anal she said 'Just a moment, bear with me' & just after saying that she left off the biggest fart/breezer I have ever heard in my life! this was my first experience of anal with an escort & proved to be my last !
Maybe I have too many hangups but sharing the same passage with shit never appealed to me. It was a girl who thought her education was not complete until she had experienced a penis in every possible opening. I suspect that that one episode was enough for her. However, I must add one extra reason;
4) curiousity on the part of yourself or a woman. only one time allowed!
Just like Anita says, anal sex done right can please a woman and can stimulate Her g-spot.
I know I don't do it right, been watching too many porn movies