The Longest Weekend Part 2

Author: cbtlover84
Title: The Longest Weekend Part 2
Date: 25 July 2012

This is a joint story co-written by Pup Nitro and KinkyGearGuy in July 2011. Hope you enjoy it.

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- Saturday Morning -
He made sure to count the cycles of water through his ass so that he had some idea of time. He was already up to 9 cycles which meant that the water stayed in him for 45 minutes then only a 15 minute break. THere is no way that his Sir had slept for 9 hours through the night. Just as the 10th cycle started to fill him he tasted much stronger piss down his throat and he knew that Sir had woken and was giving him his morning piss. Just as he was swallowing the electro on his balls was cranked up higher and he struggled to swallow through his screams. When he finished swallowing the last of the morning piss he could feel his Sir's face next to his own.

"Have a good restful night bitch? Time for me to go cook my breakfast. I have turned off the release valve on your bardex plug, and clamped off your catheter. You dont mind holding it until I finish eating do you?"

"MMMPPPPPPHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH" the boy started thrashing as much as he could in the sleepsack.

"Don't seem ungrateful or I'll turn the electro back on, and keep a water drip in your gag to keep your bladder filling."
The boy calmed down immediately.

"Much better boy. If you cooperate and behave then we will play a game of chance to see if your chastity comes off before the end of the weekend."

It wasnt long before the boys stomach started to cramp from the fullness in his ass, and his bladder was screaming from the recycling of the piss. What made it worse was that his cock was straining against the CB unit showing him that he really did want to be in this hell afterall.

He walked back into the room and saw the boy trying to hump the air in desparation, grunting and moaning into his gag. At one time he released the valve on the bardex and the catheter at one time as the boy moaned. When the boys ass was empty he released the straps holding the sleepsack down and rolled the boy onto his side. He unzipped the back of the sleepsack and deflated the balloons on the bardex and started to slide it out.

The boy felt the intruder in his ass being pulled out and for the first time in what felt like an eternity his ass felt empty. He didn't feel the void for long as he felt his Sir's cock start to slide in to take its place.

Normally Sir's cock was something that the boy had to steel himself for, but this time it felt perfect. He felt wonderful as each little bit slid in, inch after inch. Slowly adding up to what he always mentally thought of as Sir's pet beast. He still couldn't believe although he sure could feel that Sir had actually had a footlong which was 2 inches across to boot. He felt Sir hit bottom and continue on, stretching him to fit around him. His eyes rolled back in his head as he felt Sir's balls press against him. A deep breath as he started to pull back out, leaving serious emptiness behind him... Slide back in, a little faster. Back out. The tempo steadily increasing, Sir being in no rush whatsoever. The minutes went by. The boy could feel Sir's cock thicken further as he grew hornier, taking his boy's ass. But still he paced himself. He was going to shoot when he was ready to....and he was not quite ready to yet... The weekend was just getting going.

He pulled his cock all the way out of his boy's ass and then in one swift motion buried himself balls-deep. This action got a great muffled scream into the hood's gag so he continued doing it over and over. Knowing that his boy had to build himself up to take his meat, but he was now in no position to whine. After continuing this heavy assault for about thirty minutes he pulled out quickly leaving the boy empty. He leaned right next to the boy's head and said loud enough to hear through the layers "I'll bet your ass needs a break huh boy? Or are you ready to keep going?"

"Please give my ass a break Sir" is what the boy was thinking but "MMMMPPPPPHHHHHHHH" was the only response from the hooded head.

"Well I'll take that to mean you want more. Good boy" as he patted the boy's head.

"MMMPPPPHHHHHHHHHHHHHHHHHH" came from the hooded head as the boy thrashed back and forth in the sleepsack.

Sir took a dildo modeled after his own cock, but with vibrating bumps added around the length and started to insert it in quickly. He shoved it the rest of the way in and zipped the suit and sleepsack closed over it after turning on the vibrator.

The boy started to moan, writing in ecstasy and torment as he was sent back into a rhythm of increasing and decreasing vibration designed to drive any boy into throbbing urgent need. The boy's cock swelled in its cage, deliciously painful, erotically mindboggling. The boy drifted in a haze of need....completely unaware of the second boy only a foot away, who had likewise just been stuffed in precisely the same fashion. Suffering precisely the same need,,,

Both boys now writhed in their bonds as the vibrations surged through their overly stimulated prostates. Neither boy knew that they would have a partner in their torment for the weekend, and this was going to add a great element to things. He took the hose from the boy's catheters and routed them to the other boy's dildo and vice versa. "Time for them to share a little bit" he thought to himself as he put a respirator attachment onto both of the boy's hoods that had a joint hose connecting them. Just to show the blinded boys what he had done he blocked off the hose with his gloved hand and in no time at all the boys started to thrash against the table. Their movements only served to shove the dildos deeper inside them since they weren't strapped down anymore. He walked up to one of the boys and stuck the hose on the inside of the sleepsack to let the boy's get a large deep breath of their own torment.
As the boys laid there breathing in the smell of sweat and rubber he decided it was time to let them each get a quick view of their scene. He propped boy boys up on the table, which served to also keep the vibrating dildo shoving deeper in their asses, so they were facing each other. Then he removed the blindfold portion of both hoods together and he loved hearing the muffled gasps behind the masks.

Just as the two boys were soaking in the full scene he pulled the hose out of the sleepsack and held a rag to it. Both boys smelled something sweet as they started to pass out again.

----Saturday Afternoon ----
The boys both came to and started to realize they had been moved in their sleep. Sir walked in just as the boys were shaking the sleep from their heads. He admired his handywork. The two boys were now tied in a standing position spread eagle facing one another only 12 inches apart. Their catheters were still routed to the opposite boy’s gag and they were still sealed in their rubber suits. Hanging below each boy’s CB unit was their full balls, that were now tied off and connected to each other by a chain. He had removed the large dildos from their asses and had them open and waiting for more.

Neither boy knew how they were intertwined, but by now, each had figured out that there was someone else involved in their torment. Sir, however, knew that their fates for the day were very much commingled. He took the top off a charcoal grey case that he had set between the two boys. Inside was a stacked neatly collection of items. He pulled out two objects and tossed them on the floor watching them bounce on the rubber mats. They stopped rolling and bouncing, and revealed to him the numbers 4 and 9. The boys could hear an irregular clicking as he pulled 4 metal spheres each about 2" across and 9 smaller ones about 1" across... He took a collapsible metal wire basket from the lid and hung it from the first boy's balls. He then took another and hung it from the second's. He took the 4 large spheres and placed them in the first basket, and then took the 9 and placed them in the second basket. He threw the dice again and got 3 and 4. He took 3 large balls and 4 small ones from the box.... He considered his options. He reached into the basket and pulled out 7 clothepins and started adding three across one boy's chest and four across the other. He rolled the dice again and this time he rolled double sixes as he laughed to himself. Doubles means it is time for a little challenge for the boys. He took the blindfold off of the hoods so that they could see one another and he started to explain the game.

"Both of you have been locked in chastity for quite some time and I know you'd give anything to be able to shoot right?" Both boys nodded their heads franticly. "Well here is how this is going to work. I'm going to take your CB off and take your catheter out. You are each going to be set on the milker at the same speeds. Whoever can hold out the longest wins the challenge. The loser gets locked back up immediately for 30 more days. The loser gets to stay unlocked, but he then gets turned over to the loser for an hour after we are done here."

He methodically unlocked and removed first the shorter boy's CB, watching his cock spring free. He enjoyed the sight of the naked meat against the black rubber for a moment, and then turned to the taller boy. His cock was pressed tight against the end of the cb, bits of flesh pressing through the gaps. Sir couldn't help but stroke the meat before freeing it, knowing that the boy must be really aching from the confinement, and not wanting to miss aggravating it that little bit further. The boy's cock slid out of the metal tube and promptly bounced to full mast.

The two boys were mesmerized by the scene unfolding in front of each of them. They watched as Sir started to withdraw the catheters from each cock. The boys moaned in unison into their gags as the hoses snaked from their bladders. “Its time to hear some groans and moans boys. I’m taking your gags off, but if either of you says a word then you lose the challenge and neither of you get to shoot yet.” He reached up and unbuckled the large gags that had been filling their mouths and stroked the two cocks in unison with each other. The two boys moaned and bucked in their bonds “I haven’t even brought out the milker yet and you’re both trying to blow your wads?”

He brought the cart over with his dual Venus 2000 device and fitted one over each boy’s cock, attaching it to the catsuit so that it wouldn’t slip off. He reached down and turned the dial on the lowest setting to get the boy’s attention. He knew this setting would just drive them nuts, but not let them actually shoot yet. That was still a ways off into the distance before he found a loser to this little game.

He reached over and rolled the dice again deciding that the blue dye would belong to the taller boy and the red dye to the shorter one. He rolled them and a six came up on the blue and a 3 on the red.

He went to the red timer and turned it to three minutes, and set the blue timer to six minutes and then sat back and waited for the first one to go off...

The two boys strained, cocks hard, each staring at a rubber covered bondage boy in front of him. Metal balls hanging from his nuts, milker on his cock stroking ever so slowly, metal clothespins reflecting light against the blackness of the rubber. The timers continued to tick down... As the first one counted down the last ten seconds, the shorter boy could swear he felt a slight pulsing buzz in his cock ticking off each second.

Just as the red timer rang the boy's suspicions were confirmed when the electrodes inside the sleeves of the Venus cranked up to 75% power and sent the boys both into a screaming fit. “That’s right fuckers you still have three minutes left on this cycle. That means 180 seconds left to scream. You are at 75% power right now, and every 7.2 seconds it will increase by one percent. If you follow the math then that means that the last 7.2 seconds of the cycle will be at 100% power. The first one of you who speaks immediately loses the challenge and neither of you get to shoot your wad tonight. You can scream, grunt, moan, and make any noises you want, but the first word to come out of either of you names the loser.”

The boy’s started screaming louder as they were now at 80% with just about 2.5 minutes left. He turned the timer around so neither boy could see the numbers on it and continued to speak.
“There is one thing that I will let either of you speak before the cycle ends and that is ‘Gag me Please Sir’. If either one of you screams this before the timer rings then the electro will end, we continue with the game, but you will both spend the entire night in ‘The Box’ while I sleep tonight.”

He knew that this was going to be the longest time of either boy’s life as he knew just how hard it was to endure the electro that high. He looked at the timer and there was still 80 seconds left, which meant they had passed the 90% mark. Both boys were screaming so loudly that their throats were going dry.

He looked at the timer as it ticked down quickly for him, but agonizingly slowly for the boys. Just as the timer hit the 7 second mark and the electro hit 100% he heard music to his ears. Red screamed as loud as he could “GAG ME PLEASE SIR!” and he immediately hit the kill switch on the electro.

“Good boy, you followed directions very well.” He looked up as both Red and Blue were slumped as much as their bonds would allow. “Now its time for the bad news though.” Both boys jerked their heads up quickly at the sound of this. “You had both made it to 100% and only had 5 seconds left. Since you took the escape clause neither of you is the loser or winner, but you will both be spending the entire night in The Box while I sleep in my bed. Blue I’m sure you can think of a way to pay him back for your sentence. Don’t worry, you’ll both be locked in together.”

He reached down and edged the dial up on the Venus as he reached for the dice again. This time Blue got a 2 and Red got a 4.

“Don’t either of you dare cum, or there will be even more sever consequences for you both...”

He took a moment to remove the clothespins from the boys, not wanting to risk damaging their suits. He walked over to the wall, then turned back to the boys, carrying what appeared to be a bundle of rubber in his hand. He walked over to Blue and stared into his eyes. Blue, almost automatically found himself looking down...he started to tilt his head down, desperately focused on holding his load back. Sir tipped his chin back up and opened the boy’s mouth and pushed a small bundle of rubber into his mouth. Outside of his mouth, he took the rubber flaps and stretched them around Blue’s head, buckling them together at the back. He checked that the 1” tube in the center was clear and unobstructed. He attached the rubber bulb to the metal pin beside the tube. He smiled at the boy, who couldn’t help but notice Sir’s cheeks rise ever so slightly, adding that touch of malevolence that he both feared and was subject to. The boy shivered slightly and clamped down hard to keep from shooting then and there. He rolled his eyes back in his head. At that moment, Sir squeezed the bulb. The boy felt the gag begin to fill his mouth. He squeeze again. Still quite soft the gag enlarged a bit more.

“Oh no....one squeeze per number will definitely not do. I think we’ll go for 5 per...” And he gave the bulb a quick three more pumps. At that, the gag was firm, yet pliable in the boy’s mouth. “Too bad you got a two, boy.” He slowly squeezed the bulb again. “one”. and again. “two”. Blue could feel his mouth filling, the pressure of the gag forcing his tongue against the bottom of his mouth. He started to moan. “three” Sir enjoyed the sound of Blue’s quiet whimpering. “four” At this point he knew Blue’s mouth was straining, and that the gag was beginning to force its way into his throat. “five”. He loved the expandable accordion bladder around the breathing tube on this gag... Blue was on the verge of tears.

Sir turned his attention to Red. “heheheh...you, Red, however, got a four...heh...heh...heh. This should be interesting...”
Unceremoniously he shoved the bundle of rubber into the boys mouth and pulled the straps around his head. He added the rubber bulb and looked right into his eyes as he started to squeeze the bulb. “Now boy, you got a 4, which at 5 pumps per number is going to be more than this gag will stretch. That means that you will get to max it out.”

Red started to shake his head back and forth as he felt the gag grow in his mouth. Soon his tongue was pinned to the bottom of his mouth and he felt the gag pressing into his throat. His eyes started to water and Sir gave him a brief break to adjust.

“You’re just going to have to deal with it, remember it was your dye that chose this for you, not me”. He reached up and gave the final three squeezes to the gag before he knew it was at capacity. Red was now concentrating to control his gag reflex. The rubber breathing tube inside the gag was in his throat along with the gag so he could breath ok.

“Good boys, now you can scream all you want to for the rest of the afternoon. Yes that’s right, those gags are staying in place.” Both red and blue started to shake their heads ‘no’ and test their restraints, which only served to pull on the cord connecting their balls. Sir decided it was time to edge up the Milking machine and enjoy the show. He turned the dial up slowly and he knew that now it was to a point where the boys could shoot their load if they wanted to, but neither one wanted to lose the challenge.

He sat back in his chair and watched the boys start to squirm in their bonds and listened to them moan through their very full gags. He saw the tears streaming down Red's face from the gag that was shoved deep down his throat. He moved his chair forward towards the two boys and then propped his boots up onto the chain that connected the two boys' very full balls. The boys both tried to scream into their gags as the weight increased on their nuts from the heavy boots. He reached over and picked up the control for the milking machine and turned the dial up a little higher and enjoyed the sounds of the moans. These two boys were determined not to lose this challenge. He was enjoying watching them squirm as much as they could in their bonds. Neither boy broke eye contact with the other one, almost taunting each other with their looks.
Come on Red you know that if you bust your nut then you'll be one step closer to getting that gag out. Of course it also means your cock will be locked back up. Are you going to be the punk to lose? Red shook his head from side to side and started grunting into the gag.

He kicked back and watched the two boys, enjoying their tremendous frustration. He checked the clock on the wall...the afternoon was moving along and he more in store for them before they got locked up for the night, so he decided it was time to move things along. He turned the dial up to 70% max. and pushed down on the chain with his legs. Both boys immediately cranked up their wailing and panting, neither sure whether he would cry, scream, or shoot first.

They each tried desperately to maintain their control...gasping as much as was possible through the deep rubber gags. The man knew they were each swimming in sweat by now, and still waited for their climax. He cranked the dial up to 100%. That was the axe blow that shattered both boys’ resolve. Blue screamed and Red wailed, and their spermstreams collided in midair above Sir’s boots, dropping over his feet with an almost audible splat.

Having just shot, both boys were hysterically sensitive, and panting, begging for the machine to be shut off...
Not expecting the two boys to pop at the exact same time now it was time for an extra challenge. He looked up and enjoyed the sight of the two boys struggling frantically to get the machine to stop its suction to no avail.
"Well neither one of you truly lost then did you? So that means neither one of you has to get locked back into your CB right away. Well since neither one of you needs to be locked up right away then there is no need to turn the milker off right away either. I should probably go eat my lunch anyway..."

"MMMPPPPPHHHHHHHHHHH" is all that he heard from the boys in front of him as they thrashed about.
He walked behind Red and without any ease rammed an electro plug up his ass then did the same thing to Blue. He activated the electro circuit inside the milker sleeves connected to the butt plugs on a randomized setting. Then he reached up and deflated Red's gag to a point where it would be safe to leave him that way.

"Have fun boys, and go ahead and shoot as many times as you want to now as a little ummm reward..." with that he turned around and walked out of the room, shutting the lights off behind him and closing the door.

In no time the two boys lost count of the number of times that they had blown their loads as the machine was still on 100% and the electro was running randomly through its cycle. Neither boy had the strength to scream into the gag anymore and they lost track of time.