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Description:Evan Goldstein March 03 9: Successful and pleasurable bottoming takes time and practice through dilation exercises, training of your self-awareness, and control of the pelvic floor. Of course, it may be uncomfortable at first and you might initially question how there could ever be pleasure in it — something that happens with vaginal sex the first time as well — but like anything it takes practice, patience, and following a few simple guidelines to enhance this sexual practice. I often tell patients that great bottoms have been doing it for quite some time, with many first experiencing it in their youth.