“Hugh, Hugh, Hugh,” Satan greeted him, rubbing his clawed hands together. "We've been expecting you. Does that smoking jacket full of wasps fit okay?"
"It's a bit big in the shoulders."
"Perfect. Gives those bugs more room to buzz around. Now, where can we put you down here?”
“I was thinking a nice mansion,” Hefner replied.
“Yeah, but no. We’re a little crowded down here, thanks in no small part to you. The man that revolutionized masturbation! Really built up the population here fast. We had to put in a new sub-development to accommodate all those souls Playboy helped damn. We call it the Circle of Jerks.”
“Oh, wow. So, you really do get eternally punished for masturbation?”
“Damn straight. The Big Guy has a saying, which is ‘Don’t pray to Me with the same hands you’ve been spanking it with, because I ain't listening.”
“Well, there you go. Masturbation has never really been a habit of mine. Are you sure I belong here?”
“Oh, you do, Hugh. You do. How about you concealing the existence of female pubic hair from your readers for the first twenty years of your magazine? A lot of them were really surprised the first time they saw vagina in person. Turned some of them gay as a result, so they ended up down here, too. They have their own section…it’s the most tasteful and well-decorated part of Hell.”
“Do they have mansions there? I really was kind of counting on one.”
“No, it’s more urban than that. Mostly brownstones and cozy view flats. They get light punishment, too. Sure, I send a couple imps through to slash at them once in a while—I have to, it’s in my contract with You Know Who—but mostly they get left alone. They can’t help being what they are.”
“Sounds okay. I’m sure they would love me as a neighbor.”
“Not going to happen, Hugh. Let’s take a little tour.”
Satan and Hefner stroll through Hell, with Satan ruminating on where he might situate Hefner’s soul.
“There’s a couple beach chairs left by the Lake of Boiling Shit…that’s a nice spot in the summertime. I know I’ve got room in the Pit of Pedophiles…technically, you don't deserve that, but a lot of them liked ‘em fifty or sixty years younger, like you did, so I think you could forge a bond. Or I could just stick you in the bleachers in Mortal Sin Stadium, where all the deceased Dallas Cowboys go to blow a lead every week…”
Suddenly Hefner stops. He sees a big house in the distance. Flames are pouring out of the windows, and it’s surrounded by a cloud of mustard gas. A line of imps stretches around the block, eager to pitchfork anyone inside. It’s an entirely intimidating structure, but it appears to be, at least technically, a mansion. Hefner turns to Satan.
“What about that one, over there?”
“Fuggetaboutit, Hugh. That one’s reserved for Trump.”