How do I become a better bottom? I just had a recent hook-up. This guy was really hot that I obliged to be a bottom for him although I don't usually do anal sex. I prepared by cleaning my cherry hole. But when the time comes for the "union", we had a hard time putting it in since his manhood was thicker than my usual top? We ended up just jacking-off and I can really see that he was disappointed. He said that we could meet-up next time and hopes that we can make it work the second time around.