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How do gay men learn to bottom? Without easy access to gay character models or sex education specifically geared toward them, a lot of gay men never learn good skills designed for bottoming. Even those who feel they know how to bottom may by no means come to enjoy it, given the stigma surrounding gay sex. It should come as no surprise, then, so as to many of my clients have described anxiety when it comes to bottoming. Some worry that they will allow a physically painful experience, while others have shut themselves off to bottoming again after a negative first be subject to.