The single biggest emotional stumbling block gay men have about bottoming, is being labeled less than a man. For many of us, bottoming isn’t an opportunity to enjoy a pleasurable sexual experience but an act that threatens our sense of masculinity and the respect that goes with it. Many gay men believe that if they bottom they will become “a bottom.” They fear that bottoming will create a new unwanted identity for them.
It just may be that you haven’t been able to bottom (or been able to enjoy it) because you have so many emotional issues around the act. If you can get away from the falsehood of bottoming as an identity and see it for what it is—an erotic activity—the more relaxed and receptive you will be.