Hi CL I had the same problems a couple of times with my current boyfriend. He's the only man I've ever done anal with. His aim sometimes was not on the target or pushing to get in to fast. Can u say pain ? Try guiding him in with your hands. My favorite positions that help me is from behind on all fours or standing up, also cowgirl & reverse cowgirl. That way I have to do the aiming to get him in on doing cowgirl. It does take about a good 5 minutes for me to take him all in, & it is hard for me sometimes too get my aim also. But I sometimes prefer anal sex more than vaginal being I love it so much. I wish you all the luck & hope much success and enjoyment. There's more I could tell you to try and help you out, but it would be awfully long. Much love & happiness to you both.