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Story Saturday: Pledging the Frat, Chapter 21

Jason: “So this is basically how it will look. But we still need to mount the dildo. Which dildo would you like to use? This one is 8 inches long and 1.5 inches in diameter. Or this one here is 10 inches long and 2 inches in diameter, which would be closer to Jared’s dick that he was fucking your mouth with. Actually it’s longer and thicker than his dick, but payback’s a bitch, right?”

Ben: “Can we start with the 8 inch dildo, then switch to the 10 inch later if I feel like he deserves it?”

Jason: “Certainly! It only takes about 30 seconds to switch them, so not a problem.”

Ben: “And could you shorten that chain a bit? I want him to really know what it feels like to be constantly gagged with a big cock.”

Jason: “Sure.”

Jason unhooked the chain, mounted the 8 inch dildo on the jack, then pulled Jared’s head down with his mouth only partially impaled by the dildo. Then he secured the chain so Jared would have even less room to lift his head up.

Bondage Stool Deepthroat Predicament

Jason: “Jared, now that your mouth is full and you can’t protest, I should tell you that after this ordeal, your dick will also be locked in chastity. Now, Ben, who would you like to fuck Jared while you control the dildo jack in his mouth? And which chastity device would you like him locked in? We have the Jail House, the Bird Cage which allows more room to grow, the Master Series, and the CB-6000 which is plastic and not as secure.”

Ben: “I’d really like Chad to fuck him, but could you make it extra rough on him?”

Jason: “Really? You’re asking if Chad can make something extra rough? Rough is pretty Chad’s default mode of operation when it comes to this kind of thing.”

Ben: “Yeah, but if you could make it even more rough, a bit worse than usual, that would be great.”

Chad: “Ok, that works for me.”

Ben: “And I’d like the only lube he gets to be from his mouth, just like I had to deal with. But he only gets 15 seconds to lube your dick with his mouth instead of the 30 seconds I got.”

Chad: “Works for me.”

Ben: “And he only gets to use his tongue, no dick in mouth, just what he can do reaching his tongue out and lapping at your dick.”

Chad: “Sounds nice and evil, I love it! Anything else?”

Ben: “Not for that part. But after, I want him locked in that chastity device. It looks like some pretty thick steel, and I’ll bet it’s really heavy. I don’t want him ever forgetting that his dick is owned by someone else.”

Ben was pointing to the Master Series chastity device.

Jason: “Ok, I’ll have it ready.”

Chad disconnected the chain that was forcing Jared’s mouth down on the dildo. He whipped his cock out, grabbed Jared by his hair, and held his head up so his mouth was within inches of his dick, but not close enough to take it in his mouth.

Chad: “LICK!”

Jared felt a new level of humiliation. He was only given an opportunity to lick Chad’s dick for lube for his ass, not even suck it, and now Chad wasn’t even going to put his dick without Jared’s reach?

Jared did nothing.

Chad: “You do realize your tongue is providing the only lube you’re getting before my cock goes in your ass, right pledge?”

Jared closed his eyes, trying to get this out of his mind. He couldn’t believe that the tables had turned on him like this.

Chad: “And you do realize you’ve only got 10 seconds to lube up my cock, right pledge?”

Jared: “What? Ben said 15!”

Chad: “You’ve already wasted 5, now 7 seconds.”

Jared had no idea he had already started counting down. He reached his tongue out as far as he could, barely flicking it on th tip of Chad’s dick. He reached his tongue out more, straining to reach more of his cock. If Chad’s big cock was going in his ass, he was going to make damn sure it wasn’t completely dry.

After he showed some effort, Chad leaned in a bit more. Jared took full advantage of that and was lapping at Chad’s cock like it was an ice cream cone. Even more humiliating for Jared? Hell yeah it was. But it was his only opportunity to avoid making his ass pounding just a little less torturous.

Chad: “3…2…1…”

At the last second, Chad leaned in a bit more, and Jared dove down on his cock like it was his last meal, deepthroating it, gagging on it, he didn’t even care. He knew it was his only chance. But just as quickly as that started, it was over, and Chad pulled his dick out.

Chad: “Get ready for your practically dry fucking, pledge. Don’t you wish you would’ve gotten to work immediately and not wasted those valuable 7 seconds? Hahaha”

Jason laughed.

Jason: “Not a very smart pledge, are ya? You’ll learn to do what you’re told immediately around here, especially when Chad is giving the order, or opportunity to make things a bit less uncomfortable for yourself in this case.”

Jason impaled Jared’s mouth on the dildo jack and reconnected the chain so it held his mouth on the dildo. Chad went around behind Jared and got in position for a cruel, relentless fucking, like only Chad could deliver. At the same time, Ben got down on the floor and grabbed the handle of the dildo jack.

Ben: “Can I come up with some rules for him? Or even more of a game?”

Jason: “Sure, whatever you want, you’re in charge of Jared’s predicament right now.”

Ben (looking at Jared): “Ok fucker, listen up. This is how this is going to go. You enjoyed making me suck your big cock, making me take all of it, gagging me with it, all of that. Well now you’re gonna fucking pay for all of that! Chad is gonna pound that extremely vulnerable hole of yours, and without much lube since you half-assed that opportunity. While he’s doing that, every time you make a sound, I’m gonna crank this dildo deeper into your mouth. I expect absolutely no moaning, no ‘Ouch’ or 'Ahh’ or cussing being muttered, not a sound. You’ll take it and deal with it with no audible realease or way of making it any better. Got it?”

Jared: “Huuuker!”

Ben: “Calling me a fucker already eh?”

Ben reached for the jack handle and gave it a turn. Jared didn’t think he could possibly be serious. He thought he was all talk, until he felt the dildo violate his mouth even deeper than it was before. He tried pulling back, but the ungiving chains wouldn’t allow much movement. He was stuck there with his mouth impaled on the dildo until this ordeal was over, and he knew that wasn’t happened until Chad finished violating his vulnerable hole. But how was he going to remain quiet, when Chad’s dick was barely even lubed?

Ben suddenly felt Chad’s big cock poking at his hole. He wanted to do something to stop it so bad, but he could do nothing about it. He couldn’t even say a word with his dildo-gagged mouth without risking Ben forcing the thick dildo in deeper. As Chad inserted his cock into his hole, he fully realized he was fucked, literally and figuratively.

Ben: “Ahhh!”

Jared: “That was a sound!”

Ben grabbed the dildo jack handle and gave it another turn, forcing the dildo to impale Jared a bit more. Jared suddenly thought of an idea to make his predciament more bearable. He leaned forward a bit to make the dildo bend on an angle. He figured that way, he could save himself from about an inch of it being in his mouth. But how long could he do that for?

Bondage Stool Deepthroat Predicament

Chad wasted no time in going to town on Jared’s hole. He went from easing into it one second, to a vigorous, relentless pounding the next. After all, Ben did ask him to be rougher than usual. Giving Jared no time to adjust or get used to his cock would do just that.

Jared: “Huck!”

Ben: “There’s that F word again, even though it didn’t sound like it.”

Ben turned the crank a little more.

Bondage Stool Deepthroat Predicament

Jared wasn’t sure how much more he could take if Ben was going to keep cranking that dildo deeper. It was only about an inch from the back of his throat at this point. Although he was only cranking it a little higher each time, all of the cranks combined were starting to add up.

Chad continued fucking Jared’s vulnerable hole.

Ben: “Chad, could you go in and out a little deeper each time? All the way in and almost all the way out every time?”

Chad: “Sure, no problem, I’d love to.”

Ben: “And when you thrust in deep, could you slam your cock in really hard?”

Chad: “Definitely. I like the way your mind works, pledge.”

Of course he liked the way Ben’s mind was working. It matched Chad’s devious thoughts, relentless attitude, and overall evil mindset.

Chad immediately started slamming Jared’s hole, harder and deeper than before. On the first slam in, it definitely got a reaction from Jared.

Jared: “Oooowww! Huuuuck!!!”

Ben: “I couldn’t quite understand you jared. Take the dick out of your mouth and say that again. Oh wait, that’s right, you can’t take the dick out of your mouth. Haha. But either way, that was a sound, and a sound means another crank.”

Ben once again reached for the jack handle and gave it another turn. Jared pulled his mouth up as far as possible. He had no other choice, it was either that, or gagging, and he was pretty sure gagging would be punished with additional cranks since it would be considered a sound. He pulled up as far as the ungiving chain would allow.

Bondage Stool Deepthroat Predicament

Ben: “Keep pounding Chad, I want this little fucker to fully realize what it’s like to have his ass pounded while his mouth is impaled on a big cock, and gagging on it too. We haven’t gotten there yet, but I’m pretty sure he’ll be gagging soon enough.”

Chad continued his relentless assault on the pledge’s ass. He thrusted in hard and deep, and occassionally even smacked his ass with his hand, only adding to Jared’s humiliation. Jared was a completely broken boy, who still had to focus and concentrate hard on holding his head up high enough to avoid gagging on the thick dildo.

Jared had lasted quite a while now without making a sound. Maybe he had somehow mastered the art of dildo impalement? ;) Ben wasn’t satisfied though, and wanted to make sure Jared suffered just as much as he did, if not more. So he reached for Jared’s exposed ribs and lightly dragged his fingers along them.

Jared: “Ahhahaaaa!”

Jared was indeed ticklish, and couldn’t hold back his gagged laughter. He laughed. Then he gagged on the dildo.

Ben: “ANOTHER sound? Haven’t you learned yet Jared?”

With that, he reached for the dildo jack crank yet again.

Bondage Stool Deepthroat Predicament

Jared knew he reached for it, and immediately started slightly shaking his head, as if to say “Please don’t!” The dildo he was impaled on didn’t allow for much movement, but he did everything he could to get his desperate pleading across to Ben, without making any noise. Jared didn’t think he could handle another turn of that crank without gagging.

Ben: “What do you think, Chad? Should I give it another crank?”

Jared feared the worst. He knew Ben basically has his balls in a vice and was desperately hoping he’d be merciful on him.


Mike services Jake

0:03…0:02…0:01…

Finally, with no time remaining, Mike blurted out his answer.

Mike: “Ok ok, can I give you two blowjobs?”

Chad: “Just in time. Jake, please see to it that Mike here gives you two GOOD blowjobs to completion. I want you to rate each blowjob on a scale from 1-10. Pledge, we will be taking the average of the two ratings. If you average 9 or 10, then you’ve successfully completed your service for today. If you average 7 or 8, you’ll be wearing a speedo to class tomorrow. If you average 6, you’ll also be feeling some pretty intense vibrations in your ass at random times throughout the day tomorrow, including when you’re in class. And if you average 5 or below, we’ll be adding some Icy Hot to that vibrating butt plug. Is that understood?”

Mike: “Whoa, what?”

Chad: “Did I stutter, pledge?”

Mike: “Did you really mean all of that?”

Chad: “Yes, I meant all of it. Sounds like you’re having a hard time understanding the rules, pledge.”

Jason: “Maybe we should list the rules out for him, to help him remember them?”

Chad: “I like that idea. Go get me a black marker.”

Jason: “Ok, and some paper?”

Chad: “No, no paper needed.”

Jason: “Jason paused for a second, not sure about what Chad had in mind. But he knew whatever Chad had up his sleeve, he would love having a front row seat to watch it.”

Jason returned with the black marker.

Chad cuffed Mike’s hands behind his back while he was kneeling on the floor. He used some rope to further secure him in place.

Chad: “Pledge, I’ll give you once chance to see how well you remember the rules. Jake, he’s all yours.”

Jake: “It’s time to suck dick, pledge! Remember, do a good job, or else!”

Mike opened his mouth wide to receive Jake’s dick. He seemed to be on his best behavior sucking it as if he actually wanted Jake to enjoy it, which was quite an attitude change for Mike. Was this pledge finally being tamed?

Jakes cock was getting harder. When it was pretty rock hard, the thickness was more than Mike could  handle.

Jake: “I just felt your teeth, pledge! Big mistake. You just lost a point from the maximum you can earn, and I’ll continue to deduct a point every time I feel teeth.”

Mike continued sucking, trying to keep his teeth out of the way. He was so focused on this that he wasn’t going down all that deep on Jake’s cock.

Jake: “Deeper, pledge!”

Mike tried going down a bit deeper, but focusing on keeping his teeth off of Jake’s thick cock was already proving to be extremely difficult.

Jake: “I’m deducting another point for not going down deep enough. I said DEEPER, pledge!”

Chad: “Haha, looks like this pledge might be wearing a speedo to class tomorrow!”

Mike started going down deeper.

Deepthroat Dick Sucking

He did pretty well for about a minute, but then Jake felt it again. This time it was worse, as Mike’s teeth scraped along Jake’s cock.

Jake: “That’s just got you another point deducted. I see a pretty humiliating trip to class in your future, pledge.”

Then, Jake felt Mike’s teeth for the third time.


A few minutes later

Jake: “I’m gonna cum! You better take my load pledge! If you spill any, you’re fucked, and you’ll lose another 5 points!”

Chad: “Pledge, I want you to take Jake’s load in your mouth, but don’t swallow. Hold it in your mouth for further instructions.”

Jake finally shot a huge load into the pledge mouth. Mike lowered his head in disgust, and most of Jake’s load spilled out. He even spit some more out.

Chad: “Not a good move, pledge. Now you’re gettin fucked before the next blowjob. And the only lube you get is the cum that’s leftover in your mouth. Don’t you wish you wouldn’t have let so much spill out now?”

Jake: “Wow, I love that idea Chad! That’ll teach him not to spit my jizz out!”

Chad: “But first, pledge, let’s see how well you remember the rules. How many points max can you get from the blowjob you just gave, and what does that mean for you if the second blowjob is the same?”

Mike: “Um, 8? And I’ve completed my service for today?”

Chad: “Jake felt teeth 3 times, and he made it clear that you’d lose 1 point for each time. You spilled his jizz, and he made it clear you’d lose 5 points for that. He also decucted a point for not going down deep enough. Sounds like you do need a little help remembering the rules.”

Chad picked up the black marker and started writing the rules on Mike’s chest.

Rules

Chad: “There, now all you have to do if you forget the rules is look down, or ask one of your fellow pledges to read them to you when your shirt is off, haha.”

Mike had a defeated look on his face.

Chad: “Now who wants to shove their dick in this pledge’s mouth to get lubed with the little bit of jizz remaining there, then fuck the pledge?”

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