I've done anal years ago, and it hurt like hell, even though they were gentle and used lots of lube.

I've been masturbating anally for quite a little while. I got hubby to enjoy anal with me, finally, after a little coaxing and talking him into it. I loved it!!! It was more... intense, more pleasureful, more everything with another person than alone.

The tricks are to be sure that you are used to having something in there. Otherwise, you'll be in pain trying to get it out. Be sure that you're used to something the size of the man you're going to fuck. Also, an anus is NOT a vagina. It does not self lubricate. Also, the lining of the rectum are only ONE CELL THICK. It does not take much at all to damage them. Another trick is to relax, and completely trust your partner. You can open the anus further by pushing down, lightly, like you're having a BM.

Be careful with the idea of an enema first. Some people will tell you that they're a good idea. They are helpful to keep you from having a BM in the middle or right after. However, most of them will also irritate the lining even further, leading to more of a risk of damage or injury.

I've usually, in the past, had a heck of a problem with having to get up and run to the bathroom right after a guy cums in me. For some reason, I'm not having that problem now. You might want to have him use a condom, even if there is no risk or worry about disease. If it's a casual partner, of course you will. Also, you'll have to clean up the lube, the BM, and the cum (if he came in you). Don't use toilet paper, as it will leave irritating paper "fuzz" on and in you. You're better off using Tucks wipes, which do not contain alcohol. You can use baby wipes instead, if you can find some that do not contain alcohol. Alcohol burns! Most baby wipes contain it. (I wonder if that's why babies cry during diaper changes?) Failing that, you can use an old washcloth, especially one that's dark colored, and a mild soap, if you're sure to rinse it off. Wash it using chlorine bleach between times.