After gagging Jim with the open mouth gag, I left him there to drool all over himself for the next hour. I watched him struggle as he attempted to not shove the huge 10 inch dildo in has ass even deeper than it already was. He had to lean forward to prevent it from plunging deeper into his hole which meant there would be no relaxing for him for the entire hour.
After the hour was over...
Me: "Has your cocky attitude dropped down a few pegs yet boy?"
Me: "Hmm, I can't seem to understand you boy. I figured your big mouth would have plenty of room to talk around that gag. I guess not. Wow, you're a mess. Looks like you've been drolling all over yourself for the last hour. How humiliating that must have been for you."
I removed the gag.
Boy: "Fuck you! This dildo is so fucking deep in my ass! Take it out!"
Me: "Is that any way to ask me for a favor boy?"
Boy: "Come on, don't be an asshole!"
Me: "What did you just say to me boy?"
Boy: "You heard me."
Me: "I'll give you one more chance to take that back and apologize."
With that, I cuffed his hands behind his back, pulled him off of the bench, removed the dildo from his ass, and pushed him down on the bed on his back. I strapped a different gag on him. This one is a dick gag, one that I could adjust anywhere from not so tough to take to literally gagging on it, or anywhere in between in small increments. This gag would allow me to adjust it while it's strapped on him too, no need to remove it for adjustments. I put it on the smallest setting and strapped it on from behind his head.
Then I pulled him down onto the floor and put him on his knees. I cuffed his hands to an anchor point above him. I locked a spreader bar between his ankles and tied his balls down to the center eyehook so he wouldn't be able to sit up much higher. I grabbed an even bigger, much thicker dildo, lubed it up, and started driving it into his ass.
Me: "You called me an asshole. Big mistake, boy. Now you get to be an asshole, a role you play so well. But you're going to be an asshole that's going to open up real wide to take this much thicker dildo in your hole, which I've anchored to the floor at it's base. As soon as I get it all the way in, you won't be able to lift up to let it slip out all the way. You can try, but I guarantee that if you do, your balls will hate you for it and it still won't do you any good. But you can lift up off of it a few inches, and that's exactly what you're going to do...repeatedly. This is for the 'Fuck you!' comment that you just made. Now you're going to fuck YOU, and maybe you'll think twice before letting something like that slip out in the future. I suggest you also think about a nice, sincere apology during that hour. If I don't believe it's genuine, you'll stay like that for another hour. So to recap, you're going to constantly fuck that dildo, up and down, up and down, non-stop for the next one hour straight. If I see you stop at any point, you'll start over. I don't care if you're 59 minutes and 30 seconds in, you'll still start over. And since you're blindfolded, you won't know when I'm watching and when I'm not. While you're fucking that huge dildo, you'll also get to deal with that dick gag in your big mouth. It's adjustable, and I can force up to 6.5" of that dick in your mouth and lock it in place. If you're good, I won't do that. If I see you stop fucking that dildo, each and every time, I will force more of that dick gag in your mouth before I make you start over. Understood? And I could also put some clover clamps on your nipples. Keep that in mind before you answer that question."
Boy (still gagged): "Mmmyes ir."
Me: "Wow, so obedient and respectful all of a sudden. But don't think I'm going to let you out of this. I want you to remember how to be obedient and respectful."
About fifteen minutes later, I noticed Jim just sitting there, not moving. I immediately adjusted the dick gag forcing an additional half inch in his mouth.
Me: "Your hour is starting over boy, as soon as I see you start fucking that dildo again."
Me: "Should I add time too? Want to go for 2 hours?"
Boy: "Mmorry ir."
Me: "That's better. Your hour starts over now."
This time he knew I meant business. He continued fucking the dildo, slowly, but consistnently for the entire hour. After the hour was over...
Me: "You may stop fucking the dildo now, boy."
I heard a sigh of relief, and I removed the gag.
Me: "Anything to say to me boy?"
Boy: "I'm sooo sorry Sir for everything I did wrong. I'm sorry for my arrogant attitude. I didn't realize what you were capable of, punishing me like this, yet somehow still keeping my dick hard and in despearte need to cum. It will never happen again Sir."
Me: "Good boy, much better response. Would that dick like some attention now? A nice edging?"
Boy: "Yes Sir! Oh please Sir, I'll do anything! My dick NEEDS attention so bad!"
Me: "Your dick what?"
Boy: "My dick really really wants attention. Please edge me Sir, whatever you'd be willing to do with it."
I laid him on the bed, cuffed his hands and feet to the corners, and locked a leather hood on him with a built-in blindfold and built-in removeable gag which I left out for now, just in case I need to shut him up later. Then I suspended a feather duster over him so it hung directly over his cock. I setup an oscillating fan on a chair next to the bed, then turned it on. As soon as he felt the first pass across his cock, it throbbed and almost stood straight up.
Boy: "Oh wow, finally!"
Then it brushed past his cock as quickly as it touched it.
Boy: "What the hell? What's happening?"
Then another sweep across his cock a few seconds later.
Boy: "What is that?"
Me: "This is my edging torture pendulum, boy. Every few seconds, you'll feel something sweep across your cock in a random pattern. Most likely, it won't sweep across the same part of your cock or in the same way twice in a row. You won't know what to expect, or when. Good luck getting used to that! The nice thing about this is that it should be plenty to keep you rock hard, but not enough to make you cum. This will continue for the next 2 hours."
Boy: "What? Two HOURS? This is already driving me INSANE with the need to cum. I can't take two HOURS of this!"
Me: "As a reminder, you don't need to cum, boy. You want to cum. But whose choice is that boy?"
Boy: "Yours Sir."
Me: "Exactly. I will give you one way to end this early. This will continue for a minimum of one hour. The second hour will be much worse, of course, since the intensity builds over time. Whether or not it continues for a second hour is up to you. If you want it to stop at any point during the second hour, you will be locked in chastity for a minimum of 2 well behaved weeks. This is separate from your chastity sentence for using the safe word. So if you end up using the safe word at some point, that's another minimum one week in chastity. I'm going to lay the chastity device right next to you so you'll know it's handy if I need to lock your dick in it. Do you understand your way to end this after one hour instead of two?"
Boy: "Yes Sir."
Me: "Any questions?"
Boy: "Could you please just jerk me off one time first Sir, before you start this?"
Me: "Absolutely not."
I kicked back for the next hour watching the edging pendulum do it's relentless, merciless work on the cocky jock's sensitive, desperate dick. After one hour, I thought I'd see if he had reconsidered, since this torment builds in intensity more and more over time.
Me: "So, would you like me to stop this merciless edging and lock your dick in chastity for a minimum of 2 weeks now?"
Boy: "Hell no! Why would I want that?"
Me: "I just figured maybe your dick couldn't take anymore of this teasing."
Boy: "Could you stop it anyway, please? This is torture!"
Boy: "Come on, I can't take this anymore, but I can't handle not having access to my dick for 2 weeks either. You have to turn this pendulum thing off!"
Me: "Oh I do? Are you giving me orders now, really?"
Boy: "Sorry Sir."
Me: "Not yet you aren't. Time for an upgrade."
I replaced the hanging feather duster with a hanging vibrating wand, positioned it so it started on the lower side of his shaft, and turned it on. I set it up so it was very easy for it to move around randomly which would make it almost impossible to get himself off with it.
Me: "That wasn't torture. But this will be. I will ask every 15 minutes whether you want to be locked in chastity for 2 weeks or not. If you say no, you'll have to wait another 15 minutes before I'll ask again. Got it?"
Boy: "Please Sir!"
Me: "I'll take that as a yes."