After some battling Pinhead gets inside Supes head and corrupts him. What Up Witches Shirt goes on an intergalactic rampage, wiping people out left right and centre, including Batman because he’s no longer constrained by his moral code. Pinhead leaves his mind and Superman flies himself into the nearest black hole, where he doesn’t die but instead becomes an incorporeal manifestation of guilt itself. I am pretty sure that when you open the lament configuration the cenobites get to choose whether they come out for you or you get sucked in to them. Also Leviathan would fucking decimate super man. There is a reason humans wanted it to stay in hell. I am pretty confident that after about 24 hours of magic chains and hooks as well as many other magic torture devices. Superman would just be worn down into a bloody pulp.
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I kind of don’t see how it could happen. What Up Witches Shirt only calls for people that actually want them in some way. Also, pinhead and the cenobites are from hell, or at least a dimension reminiscent of it, and are probably magical in some way. If they are, the hooks and stuff would actually do damage. A cenobite version of superman would be pretty awesome to see though. Ohhhh I like this one … pinhead captures Lois and turns her into a cebonite, so Superman submits to being stripped naked and sexually and physically tortured by her while Pinhead watches and masturbates.