"Anal Sex." Yes or No.?

Ok, I've looked at a lot of profiles and 95% if not all of them have anal sex as a fetish. Now, I have done anal sex before. Three times. Every time, it was with a different guy. All of them which I have known for years. So, I don't let just anybody go back there. All three guys were different sizes. I guess, what I'm asking is, Is there any way to prepare yourself to try anal sex.? Cause honestly, it sounds painful. My ass has been a virgin for a long time now. I know there are anal toys out there for men and women who are into that and they have books on that too. But damn, it really seems like everybody is into that. I'm a missin something.? When did this get to be so popular.? I've watched some videos on it, it looks painful.

All questions and comments are welcome on this.