Jim had just been sent home to start his 2 week chastity sentence over again after sending one of his daily pics as a partial pic. I made it very clear that I expected to see his entire dick locked in the cage so I could easily tell whether it was soft or filling the cage. He failed to do this, and as a result he was required to report back to me for another ruined orgasm, post-orgasm torture, and re-locking in chastity.
Later that night, I received an e-mail from him.
Boy: "My chastity pic is attached, Sir. I hope it meets your approval, Sir."
Wow, talk about a change of tune. This cocky jock was now being more respectful than ever, even more than I thought he would ever be.
The next day, I received his morning chastity pic and his 9pm pics with his dick completely soft measuring under 3 inches along with a second pic taken 3 minutes later with his dick filling the cage. Then he called me and said:
Boy: "I'm very sorry, Sir, for being such a cocky asshole. You have taught me the error in my ways, and I am very thankful for that."
Later that night, he sent his final chastity pic before bed. He did everything that day without taking shortcuts and testing me to see what he could get away with.
The next day, he sent all of his pics with no issues. But his 9pm call left something to be desired.
Boy: "I'm sorry for being cocky. Can I cum tonight?"
Me: "Really boy? You're sorry, who? And what did you just say that sounded especially submissive? Nothing, you conveniently left that part out."
Boy: "Sorry, ok? I just need to cum so bad!"
Me: "No, you don't 'need' to cum, and you won't cum. You seem to be having a hard time coming up with submissive words every night. So from now on, not only are you going to come up with something submissive to impress me, you're going to write it on your ass and send me a pic of it."
Boy: "But Sir, that sounds hard."
Me: "I could make it harder."
Boy: "Sorry Sir, I'll do it Sir."
Me: "I expect the pic of the submissive message written on your ass at night before you go to bed. Make sure I'm able to read it."
Boy: "Yes Sir."
The next day, I received his morning and night chastity pics, and his 9pm pics of his locked dick soft and also one with his dick filling the cage. Before he went to bed, he sent me a pic with "OWNED BOY" written on his ass.
I also received an e-mail from him complaining about how hard it was to write.
Boy: "I wrote on my ass and sent it to you Sir, but it was so hard to do. I had to wash it off and try again twice. It was hard to reach around behind my ass and write like that."
Me: "Sorry to hear that boy. Let me help you get used to reaching back there and getting coordinated. From now on, I want a plug in that ass when you take that pic of what you wrote on your ass."
Boy: "But... Sorry, yes Sir."
The next day, I received all of the pics that the boy seemed to have mastered already, and just before he went to bed, I received a pic showing "OWNED" written on his ass, with a plug in his ass as instructed.
The following day, he did great on everything once again and sent me a pic before bed with "NIGHT SIR" written on his ass, and it was plugged again as ordered.
The next day, he started slipping. I could tell this cocky jock was getting far more submissive than I'm sure he ever though he would, but going back to his arrogant attitude can't be tolerated. He sent me his morning e-mail in the afternoon, long after he woke up, and the pic didn't meet my requirements at all.
He also failed to send me the pics of his dick soft, then another pic of it filling the cage within 5 minutes.
I replied to his afternoon e-mail that night:
Me: "You failed to send your morning chastity pic in the MORNING, I couldn't see the entire cage when y ou sent it in the afternoon, and I never got your 9pm pics. You'll need to report to me for your punishment within 24 hours. I expect a reply within 30 minutes telling me what time you'll be here."
He replied 29 minutes later, obviously testing me:
Boy: "Ok, I'll be there tomorrow night at 10pm."
Me: "You'll be here tomorrow night at 8pm. Or, you'll be here at 10pm, then again the next night. Pick one."
Boy: "Ok, I'll be there tomorrow at 8pm Sir."
Me: "You'll be locked in chastity for an additional day for every minute that you're late, so I suggest you show up on time."
Boy: "Yes Sir."
The next night, he showed up at 7:45pm. He knew I wasn't messing around, and that testing me again would prove to be a very bad idea. I locked him in the stocks at head and hands, and I locked his dick and balls in the cock stocks. I removed the Jail House chastity cage, then mounted an ABox sound actived e-stim power box to the stocks. I put some electrified rubber cock loops around his dick just under the head and at the base, then plugged them into the ABox.
Me: "Tell me why you're being punished today boy."
Me: "I don't like having to repeat myself. I said, tell me why you're being punished today boy."
Boy: "I don't know."
Me: "I repeat, again...No, I have a better idea."
I turned on the ABox, and turned the sound sensitivity up to the max.
Me: "Now, boy."
His dick felt a shock when I spoke.
Me: "As I was saying, now if I have to repeat myself, your cock will pay the price. Now tell me why you're being punished today boy."
Boy: "He looked up at me submissively, knowing that every word would translate into his cock being shocked."
Me (louder): "Why are you being punished today boy? The sooner I get the right answer, the sooner I'll stop asking, and the sooner your cock stops getting shocked."
Boy: "Because I didn't send you the pics I was supposed to send you Sir."
Me: "That's right."
Boy: "But sending you those pics makes me fucking horny!"
Me: "Haven't I reminded you before to control your language when talking to me boy?"
Boy: "Yes Sir, sorry Sir."
Me: "Sounds like I need to teach you some self-control."
I went to get a box of marbles and a few tin trays. I came back and put a large handful of marbles in each of his hands that were locked in the stocks. I also made him clench several marbles in the crack of his ass. Then I blindfolded him.
I took some large tin trays and placed them both in front of and behind the stocks, as well as a smaller tray between his legs.
Me: "Now, boy, you're going to learn self-control. You're going to hold on to those marbles in your hands and the ones in your ass for a full hour. To make sure you do, I've placed a few tin trays on the floor around you. I think we both know what happens when marbles are dropped onto trays like that, right?"
He looked up at me submissively, as if to beg, "Please no Sir..."
Me: "Yep, exactly, it makes a very loud noise. A noise that will easily be heard by the sound activated electro box that's wired to your dick right now. So hold on tight, or maybe not so tight, you wouldn't want to squeeze them too hard and force them out of your hands or ass. Haha. Oh, and if by chance you do drop them all out of either hand or your ass, I'll be sure to fill you up again and start the hour over."