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Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 1

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One summer weekend when I was kind of bored, I decided to checkout Craigslist. Sometimes I like to browse through the personals section for comic relief, if for no other reason. It’s amazing how you’ll often see the same guy posting the same ad so many times in one day. But this time, I saw an ad that caught my interest.

The ad read:

“Well-built jock looking for an experienced Dom with a well-equipped playroom who thinks he can tame me. I’ll warn you though, it won’t be an easy task. That being said, I have no limits and I consent to whatever you want to do with me. I’ll bet you still can’t give me the attitude adjustment that I need.”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 2

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In Part 1, Jim had placed a pretty cocky ad on Craiglist:

Well-built jock looking for an experienced Dom with a well-equipped playroom who thinks he can tame me. I'll warn you though, it won't be an easy task. That being said, I have no limits and I consent to whatever you want to do with me. I'll bet you still can't give me the attitude adjustment that I need.”

After receiving my reply and agreeing to terms, he's now found himself standing naked and handcuffed in the playroom.

Me: “Like I said, I'm giving you a safe word since this is your first time. But we're in agreement that if you use the safe word, you will go home locked in chastity for at least a week, right?”

Boy: “Agreed. And like I said, you won't be able to get me to use the safe word. I'm a lot tougher than you think.”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 3

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Jim was nearing the end of his 2 hour sentence on the wooden horse, after he arrived 1 hour late for his session. He had already asked me a few times how much longer before I would let him down off the wooden horse. He seemed very curious as to what time it was, since he was blindfolded and had no way of knowing how much longer he would be there. He had 30 minutes remaining, but I didn't tell him that.

Boy: “Come on man, do you realize how fucking uncomfortable it is to sit on this wooden edge? Let me off of this thing! And my dick needs some attention! Why don't you suck it for me?”

Me: “Oohhh, that almost sounded like a safe word, but not quite. Remember, if you want to remain locked in that chastity cage for at least a week, all you have to do is say that little 3 letter word. Then you'll be released from all of this, except that chastity cage of course, per our agreement.”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 4

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A long, harsh 85 minutes has gone by. The clock projected on the ceiling above Jim shows 2:00pm. His 90 minute forced workout was almost over, or was it? His attitude would soon decide that for him.

Me: “Tired?”

Boy: “I'm fucking exhausted!”

Me: “Good. Have anything to say to me?”

Boy: “I have a few things I'd like to say, but they would probably get me into trouble.”

Me: “Careful, boy. Are you ready to apologize for your arrogant attitude?”

Boy: “Come on, I'm exhausted, get me out of this!”

Me: “Hmm, that didn't sound like an apology, and it didn't sound like your safe word either.”

Boy: “Please let me out of this.”

Me: “Apology?”

Boy: “Ok, I'm sorry! Are you happy now?”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 5

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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...

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 6

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The cocky jock was still cuffed spreadeagle on the bed, locked in a leather hood with the blindfold and mouth cover on. I hadn't put the removable gag in, yet. One hour and 5 minutes had past of the 2 hours that I told him he would be in this predicament.

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 7

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Jim had finally cum. The moment he was desperately waiting for all along. But, is it better to cum without permission, or not to cum at all? He was about to find out.

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 8

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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.”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 9

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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.

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter10

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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…”

Story Saturday: A Cocky Jock’s Attitude Adjustment, Chapter 11

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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.”