The cocky jock was put in strappado bondage, additionally with his balls tied down low using a very ungiving bungee cord. He was kept there for a full hour, as he became a sweating, dripping mess, regretting what he did to put himself there.
Me: “Ok boy, now that you’re released from this one, do you have any other choice words to blurt out?”
Boy: “No Sir, and I’m very sorry for my outburst, Sir. It will never happen again, Sir.”
After being locked in chastity again and released from the strappado position, he was sent home to resume his daily duties that have been keeping him nice and horny while locked in chastity. This time, he had truly learned that fucking up on any of them would earn him punishment, so he made absolutly sure he did everything right, and sent everything to me on time. He continued this and made it almost to the end of his chastity sentence when I had a thought. He had been such a good boy that I decided to offer him a way to earn early release. So I called him.
Me: "How's it going boy?"
Boy: "Ok, Sir."
Me: "What are you up to?"
Boy: "Just thinking about how badly I want to cum. I can't get my mind off of my cock."
Me: "Who's cock?"
Boy: "Yours, Sir. You own it right now."
Me: "Well, you still have 4 days remaining in your chastity sentence, boy."
Boy: "Yes Sir."
Me: "Good response, boy. For a second there, I wondered if I was going to hear another outburst that you'd regret later."
Boy: "I've learned, Sir, that my outbursts have been BIG mistakes, and I certainly regretted them."
Me: "Good boy. Apparently you are trainable. Would you like an opportunity for early release?"
Boy: "What would I have to do?"
Me: "Don't answer a question with a question, boy. Now I'll ask you one more time. As horny and desperate to cum as you are right now, and realizing that I could simply leave you locked for another 4 days, or longer if you fuck up again within that time, would you like an opportunity for early release?"
Boy: "Yes Sir, please Sir, I'll do anything for an opportunity to get my dick unlocked early Sir!"
Me: "Good. Be here tonight at 8pm, and plan on spending the night here."
Boy: "Yes Sir."
It was 7:45pm, and I decided to open the front door to see what the weather was like. When I did, I saw Jim patiently waiting, like a pup sitting obediently at the door, waiting for his owner to open the door and let him in.
Boy: "Hello Sir. I wanted to make sure I wasn't late, so I planned on getting here early. I was just waiting until closer to 8pm to knock on the door."
Me: "How long have you been waiting here?"
Boy: "About 10 minutes, Sir."
Me: "Good boy. Being early is always better than being late. But you've learned that well by now, haven't you boy?"
Boy: "Yes Sir, I certainly have Sir."
Me: "Come on in."
He stepped inside.
Me: "I want everything off, then stand facing the wall. You have 1 minute. Every second over that will turn into 1 minute in a very tough predicament tonight."
I started a stopwatch in my hand, set for 60 seconds. He paused for a few seconds, as if he didn't expect an order like that. Then he immediately started rushing to get all of his clothes off.
49, 48, 47...
He was unbuttoning his shirt. If he had known I was going to make him remove all of his clothes within 1 minute, he probably wouldn't have worn a button down shirt.
34, 33, 32...
He finally had his shirt off, and the t-shirt that he had on underneath it. I quickly grabbed his hands and cuffed them behind his back, using hinged handcuffs.
Me: "Keep going, you have 30 seconds remaining."
29, 28, 27, 26...
He kicked his shoes off, and was struggling to remove his socks.
25, 24, 23, 22, 21...
The socks were off.
20, 19, 18...
His cuffed hands were struggling to get his jeans off. He had to unbutton them, but his hands were cuffed with the very ungiving hinged handcuffs behind his back.
Finally, the button popped open.
15, 14, 13, 12, 11...
Still struggling to get his jeans off. All he could do was move his legs, shake a bit, and hope they'd fall down freely.
10, 9, 8, 7...
His jeans were finally down, and he stepped out of them. He looked up at me.
Me: "I said EVERYTHING off!"
6, 5, 4...
He did the same thing with his underwear, they were finally starting to slide down his legs slowly.
Finally, he stepped out of his underwear, with only 1 second to spare. I immediately grabbed him by his cuffed hands and led him to the playroom.
I removed the handcuffs, opened the cage door, and told him to crawl inside the cage with his head facing the door. He immediately complied. I then put a blindfold on him and cuffed his hands and feet to the corners of the cage. I took a wooden dowel and slid it into the cage from one side, just behind his wrists, and out the other side of the cage. I took another dowel and did the same in front of his arms, just above his elbows. This effectively locked his arms in place. I did the same with two more dowels above and below his ankles to further lock his feet in place. Using several more dowels, I slide them through the cage bars in strategic places to further restrict Jim's movement.
When I was done, I went to one side of the cage and locked the dowels in place, using small padlocks through holes I had pre-drilled into the end of each dowel.
Once I had him unable to move an inch, I reached in and removed the Jail House chastity cage that I had him locked in. I replaced the chastity device with a few vibrating cock rings. I didn't turn them on, yet.
Me: "In a minute, I'm going to turn on those vibrating cock rings. You do NOT have permission to cum. If you cum without my permission tonight, you're entire chastity sentence will start over. Understood, boy?"
Boy: "Yes Sir."
Me: "Good. I also want you to keep me posted, on a scale from 1-10, how close you are to cumming. 1 being not at all, and 10 being you could cum within 30 seconds. But make sure when you say 10, you can still prevent yourself from cumming. Got it boy?"
Boy: "Yes Sir."
I reached in and turned on one vibrating cock ring. Almost immediately...
Boy: "Five Sir."
Within another 2 minutes...
Boy: "Six Sir. Seven Sir."
I reached in and turned on the second vibrating cock ring.
Boy: "Eight Sir. Nine Sir. TEN SIR!"
I immediately turned both vibrating cock rings off and removed them about a minute later. His cock was still rock hard, hanging between the dowels where I had it locked in place.
I replaced the cock rings with one that was AC powered which I had on an automated device that could control when the cock rings were turned on and off. I removed one dowel from in front of his wrists and released one of his hands.
Me: "Move your hand toward your cock, to within about 2-3 inches of it, but DO NOT touch that cock."
He picked up his hand and moved it to within 2 inches of his cock.
Me: "Now put it back where it was."
He moved it back to the corner of the cage. His cock was even harder now than before.
Me: "That vibrating cock ring on your dick is going to go on and off at random intervals. I just showed you that your hand CAN reach your cock. However, you will not touch your cock, and you will not cum. If you do either of those things, your chastity sentence will start all over again. Understood boy?"
Boy: "Yes Sir."
I started the cycle that I had set for the vibrating cock ring. For the next 30 minutes, it went on and off and what seemed to Jim to be random intervals. A few times, I saw him shudder, heard him whimper and groan, and even lift his hand up a bit, inching toward his hard cock. But each time, within seconds, he returned his hand to it's position in the corner of the cage.
Thirty minutes had passed.
Me: "Good boy. You just might make it through tonight and get released early after all. We'll see about that in the morning, as long as you don't fuck up before then."
I reached in the cage and put a slick substance all over his dick, one that would be sticky on his skin if he touched it at all throughout the night. This was to make sure he couldn't touch his dick without me knowing about it in the morning. I mean it wasn't like his "bedroom" for the night came with a sink to wash his hands. ;)
It was pretty late, so I decided to remove the dowels, remove the blindfold, then I told him to lay down in the cage.
Me: "That's where you'll be sleeping tonight."
I tossed in a few blankets, closed the door, and padlocked both doors so he couldn't open them during the night. I moved the caged to the end of the bed that I'd be sleeping in.
Me: "Oh, by the way, you still do NOT have permission to cum, and you do NOT have permission to touch your cock. That vibrating cock ring will go on and off periodically throughout the night to test you. You used to be a cocky jock who liked to test me. Now I'm going to test you. If you touch that cock at all, this whole adventure will start all over again. Got it?"
Boy: "Yes Sir."
I could see a puzzled look on his face, as if he was thinking, "But how would he ever know if I touch my cock while he's sleeping?" But he knew me better than that. Somehow, he just knew I'd find out. But would he take that chance anyway?
He bunched one blanket up to use as a pillow, laid back in his cramped, confining cage, and pulled the other blanket over him. I could see from the look on his face that he knew this would be a rough night, trying desperately not to touch his uncaged dick. Especially with the vibrating cock ring going on and off at random intervals throughout the entire night.
He had no idea, but I set the vibrating cock ring to turn on once per hour for anywhere from 1-5 minutes each time. I heard him moan a few times throughout the night, and a frustrated sigh or two. Morning finally came. I saw him sitting up in the cage. He was so frustrated from being able to touch his cock, without having permission to do so, that he woke up early and couldn't sleep anymore.
Me: "Don't move boy."
I unlocked the cage doors and pulled the blanket off of him.
Me: "Let me see your hands, boy."
He paused, looking confused.
Me: "Hold your hands out in front of you, palms facing up."
He immediately complied. I rubbed my palms over his, checking for any sticking spots as evidence of him touching his cock. I found...NONE!
Me: "Good boy! I thought for sure you'd be way too tempted to touch your dick."
Boy (with a nervous/scared tone): "I didn't touch my cock Sir, I swear I didn't!"
Me: "Relax, boy. I know you didn't touch it. I had a little security measure in place to make sure you didn't cheat. If you had, I would've known."
He let out a sigh of relief, after thinking he was going to get in trouble for something he hadn't done.
Me: "Ok boy, you can crawl out of the cage now."
I removed the vibrating wand from his cock.
Me: "Let's get you in the shower to wash your cock off, and the rest of you. You look like a nervous, sweaty mess. By the way, you still don't have permission to cum."
He took his shower and got all cleaned up. He went to put his underwear on when I stopped him.
Me: "Wait. I'll take those."
He paused, then handed me his underwear. I told him to continue getting dressed, but he wouldn't be wearing any underwear. I knew this would only tease his cock more on his way home.
Me: "Good boy, you've made it through to your release."
Boy: "Can I jerk off now Sir?"
Me: "No, you can do that after your get home. But first, when you get home, I want you to call me as soon as you park."
Boy: "Yes Sir."
He had about an hour drive home, the entire time his ultra-sensitive cock rubbing against his jeans with no underwear in between to protect his cock from being teased. When he got home, he called me.
Boy: "I'm sitting in the parking lot Sir."
Me: "Good boy. Now go inside. I sent you an e-mail with 3 videos I want you to watch. After you watch them, I want you to call me and tell me all about them. If I find your descriptions to be accurate and they get me hard, then I will let you jerk off."
Boy: "Yes Sir."
He did exactly ad he was told, watched the 3 videos, and called me to tell me all about them, moaning and groaning the entire time like he hadn't cum in a year and wanted nothing more in life than to jerk off just one time, or ten.
Me: "Good boy. You would've never followed those orders when we started this, without being restrained, would you have?"
Boy: "Probably not Sir."
Boy: "You're right Sir, I wouldn't have. But you've trained me well, Sir. Thank you Sir."
Me: "Good boy. You're released. You may jerk off now."
Boy: "Thank you Sir! Thank you so much Sir!!!"
This story has finally come to an end.