First off, this is an advice forum, and you are a big girl, so I believe that you can do your own research. But in response to your question, I am a guy that loves getting his ass pounded. Just ask Slowdance. Yes, we are together, and yes, we each have our own sexual advice to offer. But back to the advice, first thing that you need is plenty of lube. We are like women, if we are not wet, it will hurt like a fire poker. Not a good day. Second, you may need to size him in. By this I mean start small then work your way up in length and girth. He will need to get used to any size that you use. In the begining, you might want to consider a vibrator as the vibrations will help the tissue of the anus become aroused and less tense. Also listen to him, and if you can, watch his facial expressions. By listening and watching, you can tell alot about what is going on in his head when using his ass. You also might want to try a "G-Spot Stimulator". They are long and thin with a fairly thick curved head. Prostate massage is wonderful, even more so with vibrations attached. Also try giving him head while doing anything with his ass, pain with pleasure makes the pain more bearable in most situations. If I think of more, I will post it.