I had just locked the cocky jock in a Jail House chastity cage, ready to send him home.
Me: “This should prevent you from getting any pleasure out of this thing for the next 2 weeks.”
Now that I had his dick locked up, I released him from his predicament and removed the gag.
Boy: “Come on! I need to cum, I mean I want to cum so bad!”
Me: “You just did, twice.”
Boy: “Yeah but I don’t feel like I got off. I’m actually A LOT more horny now than I was before I got off.”
Me: “Yep, that was the plan. It’s called a ruined orgasm. That’s what you get for letting yourself cum against my orders.”
Boy: “But you have to let me jerk off before you send me home locked in this cage!”
Me: “I what??”
Boy: “I mean…I’m sooo horny.”
Me: “Not as much as you’re going to be now. For the next 2 weeks, here’s what you’re going to do every day:
If any of these rules aren’t adhered to, there will be hell to pay.
Me: “I suggest you quit while you’re ahead, or at least not as far behind as you could be.”
Boy: “Yes Sir.”
With that, I sent the boy home, reminding him again of the strict rules that he will need to follow and telling him that there will be absolutely no exceptions tolerated, and no leniency.
Me: "Make sure I get a FULL pic of that locked dick every morning when you wake up and every night before you go to bed. No partial pics. I want to see that it's locked and I should easily be able to see how much it's filling the cage at the time."
Boy (with a bit of an attitude): "Yeah, I got it!"
He seemed to think that just because I released him from his bondage predicament that he was free to unleash the old attitude again. If he doesn't lose the attitude soon, he'll find out just what that will get him.
The next morning, I received an e-mail along with a pic.
Boy: "Good morning."
I replied: "While I have you locked in chastity, you will continue to address me as Sir in every message."
At 9:10pm that night, I received another e-mail with his two pics of his dick and a ruler held next to his dick in the first pic. In the first pic, his dick measured slightly under 3 inches. In the second pic, it was touching the bars at the end of the cage. I saved both pics and checked the timestamps to see when they were taken. The first pic was taken at 9:02pm, and the second at 9:07pm. He just barely made it within the 5 minute window, per my rules. I also received a call from him:
Boy: "Hello Sir. I'm sorry for my cocky attitude Sir. You clearly own my locked dick, and I am forever submissive to you Sir."
Around 11:30pm, I received another e-mail with a pic attached.
Boy: "Hello Sir. The pic of my locked dick is attached."
I guess he checked his attitude and decided to follow my rules, at least for now.
I replied to his e-mail: "You will refer to that locked dick as my property while I have it locked, or at least not refer to it as yours."
The next morning, I received an e-mail with another pic of his caged dick attached.
Boy: "Good morning Sir. Here is another pic of my dick."
I happened to be up and at my computer at the time.
I replied within a few minutes: "First off, you referred to it as your dick. I corrected you once before on that. Secondly, I told you that I expect to see a full pic of that locked dick, and that I want to easily see how much it's filling the cage. I obviously can't see that in the pic you sent. You have 5 minutes to fix those things, and send me another e-mail."
He replied 3 minutes later: "Fine, I'll fix the ones I sent after this one."
No pic was attached, and he didn't correct the way he referred to his locked dick. I waited, to give him the full 5 minutes. I never received a corrected e-mail. Here I was giving him a second chance, and his attitude kicks in again? I don't think so.
Five minutes later I sent him another e-mail: "You have 48 hours to report to me for your punishment. I expect to know today when you will be here, and that must be within the next 48 hours."
He replied: "But Sir, I'm sorry Sir. I'll send another pic right now of your locked property if you don't punish me."
I replied: "Too late. Next time, check your attitude and graciously accept a second chance if you're given one. If your next e-mail doesn't tell me when you'll be here to serve your punishment, I'm adding a week onto your chastity sentence."
He replied within a few minutes: "Yes Sir, sorry Sir. I guess I'll be there tomorrow night."
Me: "You guess? And what time?"
Boy: "I'll be there tomorrow night at 6pm Sir."
Me: "Don't be late! I'll be adding an additional day to your chastity sentence for every hour or portion of an hour after 6pm that you're late."
The next day, he arrived at 5:50pm. I could tell what I told him really sunk in. I made him strip completely at the door, cuffed his hands behind his back, blindfolded him, and led him to the playroom. I laid him on the bed spreadeagle and cuffed his hands and feet to the corners of the bed. I used ratchet straps to tighten things up so he could barely move an inch.
Boy: "Fuck that's tight! I can hardly move!"
Me: "Boy, you've got a big mouth. You should've learned by now when to shut the fuck up."
I grabbed a thick dick gag, put the dick in his mouth, and strapped the gag on behind him. Then for good measure, I grabbed a small padlock and locked the gag on him from behind his head.
I released his dick from the chastity cage. Then I put a silicone masturbation sleeve on his dick with little nubs inside of it pointed inward toward his sensitive dick. I suspended a vibrating wand from above him and connected it to the masturbation sleeve. Then I turned the wand on and left it on a really low setting.
Me: "I thought you were going to start following my rules. You just had to test me to see what you could get away with didn't you boy? For that, you get two hours like this. If you cum without my permission, I'll add a MONTH to your chastity sentence and edge you almost to the point of insanity every week. Got it boy?"
With fear in his eyes, he nodded his head. Over the next two hours, there were a few points where I could see him trying really hard to get his mind off of his dick so he didn't cum. We both knew he would go nuts being locked even for 2 weeks, but adding a month to that, he knew he could never handle it for that long.
Two long hours later, I turned the wand intensity up all the way and set a timer for 10 minutes.
Me: "You do not have permission to cum any time in the next 10 minutes. When you hear the alarm beep, you may cum only within the next minute after you hear it. If you cum any time outside of that, before or after, the same one month chastity penalty applies."
The next 10 minutes were hell for him. He was kept right on the edge of cumming, but he knew better than to let himself cum. At the same time, he had to keep himself on the edge and ready to cum in a very short timeframe when he heard the alarm sound, and he had no idea when that would happen since he couldn't see a clock.
The alarm sounded, and the clock was ticking. After another 45 seconds, I saw the first drop of cum ooze out of his cock and I immediately turned off the wand.
Boy (still gagged): "GRRRR hucker!!!!!"
Me: "Watch your mouth! That was a big mistake boy!"
About 30 seconds after the few drops of cum dribbled out of his cock, his orgasm was sufficiently ruined, and sensitivity was at it's max, I grabbed a thick rubber band and secured the wand to the underside of his cock head, then turned the wand on at full intensity.
Boy: "MMMMMPHHHHH!!!!! AHHHHHHH!!!!!"
Me: "Welcome to hell, boy. Next time, keep your smartass comments to yourself. By the way, your 2 week chastity sentence is starting over tomorrow. That's what happens when you fuck up, even if it's just to test me."
After 20 minutes of the most intense post-orgasm torture ever, I finally turned the wand off, locked his dick back in the chastity cage, released him from the position he was tied in, and sent him home to start his 2 week sentence over again.