SIR continued to rub the back of my head while he and his friends continued to catch up, laugh and tell stories. They were all sitting around and enjoying an afternoon cocktail and occasionally looking over at the rubber toy that was on its knees beside SIR. SIR snapped his finger and pointed at the ground in front of him so I immediately went over on my hands and knees and flattened my back like a table. SIR lifted his boots and laid them across my back like a footrest. Feeling the weight of his boots pressing me down made me groan into my gag and the position was making the zipper of my suit press the monster plug in even deeper.
“Sounds like he is enjoying his place for sure, SIR,” Tom said from the next seat over. “Too bad we can’t get to that plug – I would definitely like to piss in it later when it comes out. With your permission of course.”
“Oh I promise you will get the chance Tom. He will be well worn out by then I’m sure,” SIR said.
“While Dallas had him occupied in the bathroom I filled up my beer bottle. I would like to dump it down his funnel then make out with you while he holds it until you tell him to swallow.”
“You sneaky fuck how did you pull that off … nevermind! I accept these terms,” SIR said with a grin I could hear without even having to see. “Head up gimp.”
Tom stood up and came over to me and upended the beer into the funnel of my gag. I felt the warm piss fill my mouth and I had to fight not to instinctively swallow. I could see Tom’s boots under me as he leaned over and started making out with SIR above me like I wasn’t even there. I could hear the two of them growling and moaning as the kissing got more and more passionate. The funnel was full to the very brim, and I knew that if I moved the slightest bit then it would spill out everywhere, and the gravity was pushing it down into my mouth.
The makeout session above me went on for at least 15 minutes while I struggled not to swallow – focusing on breathing thru my nose but not letting my body reflexes kick in. With all this going on I definitely do NOT want to rack up any punishment.
Finally I hear them break apart and see Tom’s boots step back away from me. As he settles back down in his seat I hear him say “Swallow gimp” and I start to slowly clear the chamber of the funnel, but my bladder lets loose and I start pissing right back into it at the same time so I have even more to chug down. FUCKING HELL
“Look at that – he just can’t get enough – he is adding to what I poured in there SIR,” Tom said with a laugh.
“He is a good urinal – he is right where he needs to be,” SIR said as he reached down and pressed on the plug in my ass making me groan like a bitch in heat.
The group continued to tell stories and catch up with one another while I sweat under SIR’s boots struggling not to move until direction is given.
“Ok boys – let’s move this up to my room so we can spread out and get a bit more comfortable. Bill, you have one on account and I am going to enjoy using your balls as the price later. Why don’t you go ahead and escort it up to my room and get your fun in, we will join you in 20 minutes,” SIR said as he handed him the key.
SIR reached down and patted the back of my head signaling me to stand up, and I saw Bill get up with me.
“Sounds like a plan, SIR – I need to use it pretty fucking soon anyway. Bill started walking away and I shuffled behind him to keep up. Each step I took made the huge plug shift. We walked towards the elevator and Bill pointed at the floor beside him so I instinctively kneeled beside his boots. The elevator slowly filled with guys and each of them took care not to step on the gimp on the floor.
I could feel my dick throbbing in the suit … WAIT … I COULD FEEL MY DICK AGAIN!!!! Fuck I don’t know if this is good or bad but I can feel my dick again. Fuck I hope I don’t cum…
We got up to the 25th floor and Bill tapped my head so I stood and followed him down the hallway to our room. I followed Bill into the room and he stood in the middle of the room and pointed at the floor in front of him so I kneeled down.
“Gimp – you grunt once for yes and twice for no. Have you been holding your piss since that last time we heard you flood your funnel with Tom?” Bill said looking down at me.
“Very good because I’m fucking thirsty,” Bill said with a grin. He reached down and detached the tube from my funnel gag and put it in his own mouth. Next he unzipped his own leather pants and displayed a very hot looking cock cage with stretched out balls underneath it. “When I start to piss, you can piss as well. When I stop, you stop,” Bill said as his cock cage draped over my funnel gag and I felt the flow start. I immediately focused on pissing myself as I started swallowing his fucking great tasting piss.
“There’s a good gimp – I’ve needed this too,” Bill said as he cut off his flow and I very quickly did the same, but i still had to piss FUCK.
He picked up his flow again and so I started pissing again and fuck it felt so good – I was listening to him swallow in time with my own and my dick was throbbing in the suit.
This went on back and forth for a while, fuck how much had he had to drink! Till we heard the door to the room open and the rest of the crew came in the door laughing at a joke one had said coming from the elevator.
“Well now this is a hell of a site to see. Bill, you failed to mention you were locked and stretched, AND that you were craving piss too. Not what I had in mind but I am going to enjoy this. Time is up, now its time for your balls to pay the piper,” SIR said as he walked over and took the tube from Bill’s mouth and secured it back to my gag. He stepped behind Bill and strapped a pair of locking restraints on his wrist and locked them behind his back. Pushing bill backwards a bit to make room he reached down and gripped the stretched balls in his hand.
“Tom, start the clock. Boy, if your knees hit the ground then the clock starts over, is that clear?” SIR said. I know him well enough to know that as he said that his eyes were locked tight on Bill’s.
“YES SIR,” Bill said loudly.
SIR started slowly squeezing the stretched out balls and I could hear Bill grunting and trying to deal, and I watched his knees slowly start to buckle from the lack of warmup. Just before Bill started lowering down, SIR eased up the pressure. As soon as Bill was back standing, SIR held the balls in one hand and started slowly hitting them with the palm of his other hand.
“How long has this been locked up boy?” SIR said as the hits continued.
“I thought it would be a nice surprise for you, SIR, so I locked it up on,” before he could finish SIR gripped the balls full force making Bill gasp for air.
“On second thought let’s make a game out of it. I am going to start hitting you until we determine the length it’s been. You can tell me if hits should be days or weeks,” he said as he gripped harder and harder.
“W..WEE…WEEKS SIR IT’S BEEN WEEKS,” Bill stammered out.
“Very good – that is a nice surprise indeed. Let’s get started. When I have hit the right number you just yell YES SIR,” SIR said as he lessened his grip and got his fist ready.
“ONE,” he said as the first punch landed into the stretched balls.
“TWO,” he landed another square hit.
“THREE.” He continued to look Bill square in the eyes without wavering.
“FOUR.” I could see Bill’s knees getting weak.
“FIVE.” Bill was sweating and trying not to scream.
“SIX, fuck boy – still going eh?”
“SEVEN.” SIR landed another hit.
“EIGHT,” SIR said as his fist landed again.
“YES SIR!” Bill screamed as he struggled not to drop down to his knees.
“Eight weeks … very impressive work, boy,” SIR said as he continued to alternate squeezing and hitting the very sensitive balls. “Eight weeks you have denied yourself access to your cock and balls leading up to this. We will take full advantage of that.
While holding the base of the ball stretcher SIR started landing rapid fire hits to the balls as Bill started to really struggle not to scream. Just as his knees buckled and not a split second before they hit the ground the timer went off in Tom’s hand.
“Very close call, boy,” SIR said with a grin on his face.
“FUCK, thank you, SIR.”
Just as that happened the guys started hearing me swallowing my own piss again and they all started to laugh. “Oh now boys we can’t forget our toy over here can we?”
All eyes looked to me and my stomach tightened up in knots.
To be continued …
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For Part 1, click here