My fiancee' and I have been dating for a little over 2 years. I was a virgin when we met, but we have tried everything since then. The first time he brought up anal sex I was fine with it b/c I wanted to try everything. The first few times we did it, it was fine. It didn't even hurt the very first time. But now every time we try to have anal sex it hurts me so bad. He loves it and I used to until I got all the pain. What would cause it to hurt so bad all of a sudden? How could we make it easier and maybe a little more pain free for me?