Be careful what you bet.
Cody had me; we both knew he did. If I was in his place I'd be merciless. The bet was high stakes; whoever lost had to give the winner whatever he wanted. I thought I'd win. I'd already planned on my winnings: I'd trade cars with him for a week. Cody was in his element in his SUV and I grinned whenever I imagined him in a beat-up Kia.
But I lost. The Penguins did not win the playoffs; no SUV for me, and it was up to Cody to decide what he wanted from me.
He came in gloating. "Ha ha, LOSER!" he cried when he saw me.
"Yeah yeah. Okay, what do you want?"
He looked at me for about ten seconds.
"Show up at my house at seven, and I'll tell you then."
If I'd known then what he planned, I'd never have gone. Knowing what I knew now, I'd have gone. All the way.
I showed up at his house in the battered car I was still stuck with and knocked, and he let me in. He was wearing gym shorts, no shirt, no shoes; but I didn't think anything of it. He usually dressed like that around the house.
"C'mon in." He gave me a weird smile and he looked me up and down.
"So, I get anything I want from you." His voice was self-satisfied.
"Yeah, whatever, what do you want?"
"Follow me." He walked to his basement door and looked back at him. I was a bit irritated as I followed him down the stairs into the cool dark.
He had a pillory. It was on a big pedestal of wood about an inch high and six feet square, tiled, with casters on the bottom; that must have been why I'd never seen it before, because he had a couch down here I'd slept on quite a few times. The pillory was on the edge of the pedestal, about four feet to the crosspiece with the holes in it. It looked like a sturdy piece of work.
"In you go for an hour." He grinned and pointed at the pillory.
"You do this a lot?" I didn't really expect him to answer, but he did.
"As often as I can." I didn't know what that meant, but now I do. Do I ever. "C'mon, get in."
I put it off as long as I could, then I stood in front of the pedestal.
"No, get on it," he told me, and I stepped on the platform expecting to roll. It was locked still and didn't move a bit when I kicked it. I faced the pillory and felt this weird dread. I put my head and arms in there and he came over and locked it down on me, and put this big-ass padlock on it. It clicked like a jail door.
He looked at me and just grinned, then disappeared behind me. I didn't even feel him get on the platform, but my left leg was pulled up behind me the way you'd shoe a horse, and my shoe and sock were pulled off.
"What the fuck are you doing?" I asked him, and I felt him pulling up on my right leg and pulling at the shoe. When he had them both, he circled around into my field of view.
"Just makin' you a bit more comfortable," he told me. "Bitch."
I didn't think anything about him calling me that, we insulted each other all the time. But then his fingers were at my belt buckle, and he unfastened my pants and started pulling them down with my boxers, and I struggled and kicked threw my weight against the pillory. It didn't move, it might have been made of cement.
He got my pants around my ankles and somehow pulled them off my left leg, then my right, even though I kicked at my own leg where I felt his hands. "Cody, let me the fuck out of this thing!" That's enough man. Fucking quit that!"
He circled back into view and grinned again. "I get your ass for as long as I want it," he said to me, "so if you settle down this won't take an hour."
And then he did a dance move in front of me and I could see he was sporting some wood. I sank inside. "Aw, man, no...please..."
He looked down, and then back up at me, with that smile on his face. "What, this?" He dropped his gym shorts and stuck that huge fucking dick in my face. I was trying hard to get away from it but I couldn't escape the pillory, and he touched my cheek with it. It left a wet streak.
He moved out of view again, and I felt cold liquid run down the crack of my ass. He said behind me, "You're ass is mine, remember? Well, that's what I want. That sweet ass I been noticing."
"Fuck, you can't do this, I'll call the cops!"
I heard a swish and felt a swat across my ass that lit up like fire. I felt my ass clench up like a bank safe and a tear came to my eye I couldn't reach to wipe away. It was followed by another, then another and tears rolled down my nose to drip on the floor beyond the edge of the pillory. My back started to hurt from being in the pillory.
"You won't say shit, bitch," he told me, and now I knew he meant 'bitch' in a different way, like I was his property, the jailhouse I'm-about-to-fuck-your-ass way.
I felt his fingers rubbing my asshole, poking in a little, and another wash of cold liquid. His finger pushed in a little and stopped when I tightened up, then it'd go out a little and then in deeper, and I'd tense up and it would stop, and it went on like that til I could feel his finger moving inside me. Then it pulled all the way out and my ass shut tight, then it relaxed and he went all the way in with that finger and I made a yelping noise. I felt it rubbing around in there and it felt like a doctor visit. "How's the prostate, dick?" I yelled back at him, with hate in my voice.