For me bottoming is all about the connection. There are tops who act like they are special and doing you (the bottom) a favor. I am all about making love. I have had hired tops who left me cold and other who were incredible. The common denominator for those who are incredible is that they go slowly, and they seem to be genuinely interested in how I am feeling.
Another thing is how often I am topped by the gentleman. If he is good, he gets better with each visit.
I see a gentleman about every two months when I visit his town on business. At first the bottoming was okay, but he was very sexy. Bottoming hurt. Over the last 3 years we have come to know each other personally. I know what he enjoys and he knows what I enjoy. When we get together, all I can think about is making him happy, so I do those things. And he seems to feel the same way about me. Now bottoming for him is incredible!