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Max fucked poor Jake mad, all the while the spicy lotion felt like fire on the poor boys balls and nipples. Tom and Joe continued to massage the lotion anywhere they thought it would cause Jake discomfort. He was no longer close to shooting his load.
After Max was done, he collapsed on the bed breathing hard. Jake took that as a sign he too could rest. "Hey, not so fast newbie. Joe and I are next." Jake was roused back to his all fours, with Tom hopping behind him, and Joe standing in front, with his erect cock right at Jake's mouth level. The two penetrated the slave almost simultaneously, causing Jake further discomfort. Max took the opportunity to reach up and slowly stroke Jakes cock, with the spicy lube. Jake's mind was blown by all the sensations he was feeling. Pain in his ass, ball and dick, all while his mouth was being fucked hard by Joe. "That's is Joe, lets ride our toy like a stolen bike."
While the pain was extreme, Jake was somehow thrilled by the sound of Joe and Tom kissing over his arched back. Max, still teasing Jake's cock, laughed "I always wanted to see the Eiffel Tower. I'm guessing this version is way better than the original."
The two boys changed position a couple of times, taking turns on both ends, before busting their nuts into the slave. As all three boys slumped to the mattress for a moment of rest, Joe noted tears in Jake's eyes. "Looks like we are close to breaking this one. Maybe we should give him some relief."
"Help is on the way," offered Max. Before walking over and dumping a cup of ice onto Jake's genitals. That should cool you off a bit. The ice didn't really do anything to calm the chemical heat in his balls. Instead it just caused further discomfort. And yet, somehow he wasn't entirely unhappy with the situation. 3 naked, hot studs using him like a plaything, for their own gratification.
"Still more than 2 hours before he is allowed to use his safe word. What should we do with him?" Max asked the others.
"I think we should leave it up to chance. Remember when Master did the reverse draw with Connor. Let's do that", suggested Tom.
The reverse draw? What was that, the poor slave wondered. How much worse could things get.
"Ok, Jake we are going to put 6 punishments into a hat. You will draw one every 5 minutes. The last one is the punishment you have to complete. What punishments should we put in guys?"
"1 hour getting whipped on the cross."
"1 hour getting tickled"
"1 hours on the cross, by the pool, with the wireless anal probe up his ass, and the remote being passed around to anyone still out there"
"wireless anal probe, covered in spicy lube, on the cross, while we spank him with paddles". "Fuck Max, that is harsh, even for you. I love it."
"Ok, we need to give him something to hope for. An easy one. How about 20 minute ice cold shower, followed by being walked around the compound, on his leash, so everyone can see his shrunken penis."
"And one last one that he needs to pray doesn't get picked. What about 'All of the above'."
"wow, all of the above. Tom, I thought Max was the nasty one. You are just evil."
The boys wrote each of the punishments Acıbadem Escort down on paper, folded them, and placed them in a hat. Tom held the hat above Jake's head, and told him to reach in a grab one. Jake opened the folded paper and read it out loud "1 hour of tickling." Damn, that was probably the second best one for Jake, but at least the cold shower - by far the least bad option, was still out there.
For the next five minutes the boys tickled Jake. The time between picks was brilliant, it increased Jake's stress and gave the boys some time to torment him.
Jake reached up for a second time, pulled out a piece of paper and read "Anal probe by pool." Damn, another one that was better than average. He really needed to shower now, as the rest were ugly punishments.
The boys spent the next 5 minutes attaching nipple clamps to poor Jake, and pulling them lightly, while chanting "All of the above" and laughing.
After 5 minutes, Jake reached up for a third time and reached into the hat. "Whipped on the cross." Phew. The first good news in a while. Tom grabbed Jake, and flipped him over. The boys spent 5 minutes lightly paddling his ass. Enough to redden the cheeks, but not enough to actually break skin.
Joe then flipped Jake back over and held the hat up high. Jake again, shaking in fear, and excitement, reached up for another piece of paper. "Spicy wireless probe". That left just the cold shower and 'all of the above' in the hat. Max grabbed a blindfold, and put it on the slave. He then told the boys to tickle Jake again. Jake could barely breath, and Tom and Joe seemed to be laughing the entire time as well.
When the time was up, the blindfold was removed, and Jake was steeling himself to reach into the hat one last time. Either he would be fairly uncomfortable and humiliated by the pool, of he would be in a severe world of hurt. His hands shook as he reached up...."Stop," Max called out. "I have a deal for you Jake. If you agree to giving back all of the $12k, you can choose your punishment - except for the shower. You can have an hour of tickling, or the anal probe by the pool. Or you can keep the money, and reach for your punishment. But if you keep the money, and pick 'all of the above', we won't let you buy the safe words later. You will have to do the entire 18 hour stretch."
Jake was stunned. He had already done over 5 hours of punishment. He couldn't give all the money back now. But if he selected poorly, he wasn't sure he could last the full 18 hours. And all of the above was a nightmare. He ponder the situation, and was once again surprised by his own voice, "Fuck it, I'm no quitter. I am going all in." With that he reached up and selected, opened the piece of paper and was thrilled to see the words "Cold shower". Yes! He was doing the cold shower. He pumped his fist in victory.
"What are you excited about slave boy. That is the punishment you eliminated. You do the punishment left in the hat." Fuck, in all the stress and excitement Jake had forgotten the rules. He was left with 'all of the above'.
What Jake didn't realize was, when he had been blindfolded, Max had removed all of the above from the hat, Acıbadem Escort Bayan and replaced it with a second cold shower. The hat was rigged, Jake couldn't win.
"Ok. I think we start easy, and work towards the harder stuff. Lets throw him in the shower," suggested Tom. The others nodded, and Jake was being lead towards the shower stall. Joe turned it own, all the way towards cold, and the boys pushed Jake right into the middle of the stream. Jake jumped back in shock, was was quickly repositioned by the three boys. Jake lost his breath, the water was so icy cold. Joe made sure Jake got his full head under the stream, and then aimed it right at his dick. After several minutes the cold was having the desired effect on the slave, as his typically impressive penis looked more like a young's boys dick now. Jake shivered, chilled to the bone by the time 20 minutes was up. If this was the easy task, the hard ones were going to be murder.
The boys put Jake's leash on, cuffed his hands behind his back, and lead him towards the outdoor patio. There were still a few gentlemen, and slaves around the pool. Some of the boys, having completely their own duties, were enjoying a swim. The all watched in awe as Jake was walked around the pool several times, for their amusement. The girls were still mulling around, refreshing food and drinks. They pointed and laughed at Jake's timid member. "Looks like somebody is having a tough day."
After several laps of the pool, a few up close visits with various men, Joe whispered to Jake "Congrats, one down. That wasn't so bad." Jake breathed a sigh of relief. Maybe he could survive this after all. Joe pulled Jake's leash lightly, and led him towards the stage. On stage Tom pulled out the wireless anal probe and told Jake to bend over. Fuck, this was about to get much harder. Jake bent forward, and the boys slowly spun him around, so the entire crowd could get a look at his sweet hole. Max lubed up the boys backside, and the probe - with non spicy lube, thank god - and slide the probe deep into Jake's ass. The three boys then helped Jake up onto the cross, face up, and shackled him in. Once shackled, they pivoted the cross such that is was vertical once again. Jake was spread eagle, naked, facing a grateful crowd, with an anal probe buried in his ass. This was going to be a long hour.
Joe hit a button on the wireless remote to get it started, before wandering over to a sexy 20 year old named Darren. Joe handed Darren the remote while given the cute boys balls a quick feel. The young stud smiled, looked at the remote and pressed a couple of buttons. The probe was now doing figure 8s, in Jake's ass, at 80% speed. Holy shit. Max leaned into Jake "Don't you dare think of having an orgasm from this. If you even look close, that hot shit is going all over your balls."
Tom grabbed some sun lotion from the girls, and asked a couple of the other finished slaves to apply it to Jake teasingly. Technically this was outside the rules - more than 3 guys playing with Jake - but Tom would argue this was just applying sun lotion, which was good for Jake.
Over the next 60 minutes, Joe would move the toy to a new spectator Escort Acıbadem every 5 minutes or so, and Max would occasionally grab some ice and hold it against Jake's balls to ensure he wasn't getting to horny from the toy. At one point, a sweaty, smiling Mr Jenkins walked outside, and wandered over to the 3 lads. "Having fun I see. If I did have a couple of boys in the dungeon, I might just be joining you. Glad to see you boys enjoying yourselves. You work so hard."
When the 60 minutes we up, the boys looked at each other, wondering which punishment went next. "Not another hour of the probe. Lets save that. We could do the tickling. Maybe do it right here. The crowd seems to be enjoying this."
"Great idea Tom. I will go grab all the tickling tools and be right back. You guys get started, i won't be but 2 minutes." Max pivoted the cross, and pushed it down so Jake was horizontal. His shoulders were relieved to get a rest, but he knew the relief would be short lived. Max and Tom started to tickle Jake's feet. He shook with laughter, trying mightily to catch the occasional breath. Despite all the pain, discomfort and humiliation he had been through, it wasn't long before Jake was once again sporting an erection. Max smacked at Jake's hard cock, "get control of yourself, or i am getting the hot sauce!"
Jake groaned. He had long ago lost control of the situation. The tickling, crowd and lack of oxygen was driving him wild, and nothing he could do would control his dick. Max realized the situation and offered "Ok i am not going to get the hot sauce, that would be cruel. BUT, if you cum during the tickling, we start the whole 'all of the above' over from the start. KEEP CONTROL OF YOURSELF!" Well that temporarily fixed matters, but Jake new all to well, it was only a matter of time before he would be hard again.
After an hour of tickling, Jake couldn't believe he had somehow managed not to cum. The crowd had cheered the entire time, egging him on to bust a nut. They were amazed and disappointed when the timer notified the boys that time for this task was up. Jake's celebration was short lived. "I say we do the anal probe, with the lube, while paddling his ass, right out here. The crowd is eating this up."
"please no", Jake begged. For the first time all day, he was feeling truly broken. He couldn't take 2 more punishment. No the hot lube, and then an hour of whipping. "Please let me off easy."
Tom spoke first, "What should we do guys. He has been a very good sport so far. Do we let up?"
The words were music to Jake's ears. Perhaps they would give him a break.
"Easy for you to say Tom. You didn't pay 12 grand for this. I paid for 18 hours, i am going to get 18 hours........unless, Jake you are willing to redo our deal."
"Please Max, anything. Just let me rest for a bit."
"Ok, you return 10k. I think you deserve some money for being a good sport. And you agree to let us randomly select 3 of the spectators watching right now. Owners or slaves - we will pick names from a hat. You have to give each of them a blow job, right here on stage. And finally, you agree to wake me up with a blow job, each day for the next two weeks."
"Deal." Jake started to sob. He couldn't believe how happy he was. All he had to do was give 17 blow jobs, and return 10 thousand dollars. Ok that sounds like a lot, but it was way better than the alternative. And he was actually kind of looking forward to waking Max every morning.