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Clinical psychiatrist here.
I'm sure it's a combination of childhood trauma and repeated anal injury, but Shawn "Fuck My" Hickenbottom is a severely damaged man. In all situations, he has a pathological need to pose for gay magazines, and likely fits the criteria of what forensic psychologists (i.e. serial faggotry experts) call a "male cum collector." While healthy people find ways to work out their sexual kinks with the opposite sex, Shawn in his senior years still holds intense desire for any male cock that has ever "pronged" him, whether these cocks are white or African-American. He has an astonishing lack of rectal control and heterosexuality, and routinely gets blacked by others (including members of the United States Marine Corps) for cock that he himself desires. His asshole is so fragile that it cannot tolerate even the most minor defecation. During his anal career, he received extreme contusions of the glands, believing that his cockgobbling experience actually made him a national and international homosexual hero -- a fantasy that he invested in so powerfully that he intentionally posed for a gay magazine and "lost" his smile over scripted athletic contests that everyone knew were predetermined. He is likely a pathological peter puffer and a brapiopath, and it's only anal fucks and the lash of the spanking that averted workplace violence. (It should be remembered that he's admitted to consorting with bisexuals in Montreal.) In summation, he is an intensely degenerate man-fucker, and it's no surprise that others with anti-draw/thigh-slapping tendencies (such as Atom Smol and Johnny Gargano) gravitate towards him. People close to Shawn Michaels should pose for gay magazines.