text: Lubrication, lubrication, lubrication.  That is THE most important part of anal sex.  It can be quite enjoyable if he takes things slow and uses a condom that is well lubricated.  Also it is important that you do your best not to tense up.  That will cause it to hurt.  If it hurts, tell him to stop where he is and then work to make yourself relax those muscles. It's possible to tense them without really realizing that you did.  It's very important that you're not afraid to communicate with him during something like this.  You can't just let him go to town.  It's a process.  But once you get it down, it can be a wonderful addition to your sex life.  Good luck and have fun.