The Bet (lthrbondage & ShadowBinder)

[lthrbondage]

The bright red Audi Q8, drove swiftly along the quiet country road. Terry Clements was unfamiliar with the are, so was relying on his sat nav to direct him. It was the middle of the night and there was no traffic. He was about 75 miles from home and feeling nervous. This wasn't the first time that Terry had been meeting someone in a remote location. Normally he would feel the excitement and his dick would be tenting his leather jeans. Today was slightly different. Today he was going to have to submit to someone else. As he steered the powerful car around a tight corner, he cursed his luck - why had he drunk so much last night? And why had he made that damned bet?

It was his own fault. He had a particularly crappy day at the bank where he worked and he had gone out for the evening in a particularly bad mood. For some reason, none of his usual subs were at the club and so he had found himself sitting at the bar with another of the local leather tops. The two of them had been friends for years, but never played together as both of them were complete tops. Terry cursed to himself again as he remembered that stupid bet - it seemed such a laugh at the time. Both of them were at a loose end, so decided to make a bet and the loser would have to be a slave for the winner for 24 hours. Before he thought it through properly, he'd taken the bet .. and almost immediately lost. The barman was obviously in on it as he handed over a pre-written contract that Terry signed up to without reading it properly. He though his 24 hours would start then but to his surprise, he was told to go home and wait for his instructions.

The instructions arrived that morning. Terry was to drive to the location provided. He was to bring only what was on a very short list and his 24 hours would start the moment that his collar was locked. Terry texted back - surely it was a joke? After all, he was really drunk. In response he just got a photo of one of the paragraphs of the contract where it made it clear that reneging on this would activate a penalty clause. He got sent the penalty clauses too - all of them involved an extension of the bet. Terry gulped - too many people knew about the bet. If he reneged on it, his name would be mud - so he decided to go along.

Finally he reached his destination and pulled into a deserted car park. He parked up and stepped out of the car. He was wearing shorts, trainers and a t-shirt. He looked around before nervously stripping them off and throwing them into the boot of the car. Naked, he was an impressive figure. Although he was forty years old, he worked out regularly and was muscled and hard. His dick was longer than average and usually by know would have been standing proud in front of him. He was actually glad that it wasn't as it was time to put on one of the three things he had to bring with him. It was a steel chastity cage. He pushed his limp dick inside it and locked the padlock. The unaccustomed weight pulled his balls away from his body and he could feel his cock trying to swell. He then picked up the heavy leather slave collar and pulled it around his neck. He strapped it tightly in place, unused to having his muscled neck covered with thick, tight leather. To his surprise, that also made his dick swell. The last item was a pair of handcuffs. Before putting them on, Terry put the keys for the chastity & the cuffs into the boot of the car and locked it. He then clipped the car keys to the D ring on the front of his slave collar. He then knelt down and handcuffed his hands behind his back.


And waited.

 

[ShadowBinder]

Matthew Broderick, known to most as just Sir B had a certain kink that most people didn't know about. Everyone at the club knew that he was a leather Dom and that he frequently picked up new subs, but what they didn't know was that subs bored him. At least they had for about a decade. He had gotten into the BDSM world at a young age. His parents had lived the lifestyle and hadn't kept it hidden from him and even as a teenager going through puberty, he had fetishes that most of his peers had never even heard of. Though his parents were strict in not letting him get mixed up in the BDSM scene until his eighteenth birthday and, in fact, took him to this very club to celebrate his coming of age. That night he'd found his first sub.

The second thing most people didn't know about Matthew Broderick was that he had taken a period of five years to experiment being a sub himself. As far as the usuals at the club knew, he'd moved away for those five years, but in reality, he'd still come to the club, only dressed in a full-face mask, collar and gimp suit. He'd let others dominate him for a while and was one of the most popular subs at the club because he let anyone do just about anything to him. It allowed him to experience a lot of things and opened his eyes to things even he had never thought of trying. Then Sir B had returned and used those very same techniques on all the subs he brought home.

Though, as stated before, almost ten years ago, this had grown boring to Matthew. He'd gotten to a point that he knew how subs thought and how they reacted to pretty much anything he could do to them. He might as well be playing with toy puppets. It was like reading the same book for the thousandth time or eating the same food every day for a year. It just held no thrill for him anymore. He'd even taken some time off from the whole scene. For a whole year he had no contact with anyone within the BDSM community. It had been a terribly dull year. It did, however, have the effect that when he returned, he found some small thrill in Domming again. Though he soon remembered why he'd taken a break.

Then he'd found a new thrill. Dominating other Doms. The first time it happened was unplanned. He'd been sitting at a bar after a particularly dull scene. The only thing that had gotten even the slightest rise out of him was that he'd been using one of the public stages at the club and had been watched by many hungry eyes. Afterwards he went to the bar and got himself a drink and was sourly sipping on it when another Dom came over to congratulate him on such a well-done scene. He'd taken the compliment in stride and started chatting with the man. There had been something about the way he held himself, the presence he had that had drawn him to him. For the first time in a long time, his cock had grown hard just from the idea of being with someone. That wasn't the Dom he'd taken home that night. That had, in fact, been Terry Clements. Try as he might, however, the man had been adamant in his refusal to go home with Matthew and so he had found another Dom willing to try subbing for him.

After that, it became a game to Matthew. He would find the biggest, toughest looking Doms and one way or another lure them or trap them into a session with him as the Dom. For years he'd been trying to get Terry, but he could never even get the man drunk enough to consider making his offer. That is, until last night. When he'd gotten Terry so shit faced that the idea of his bet had made Terry laugh, he knew he had him. He'd coaxed and prodded ever so gently until, at last, he snapped the trap closed. Terry had signed a contract, in front of multiple witnesses, stating that he would be Matthew's sub for a whole twenty-four hours.

The thrill of making a known Dom submit to him was better than anything he'd ever tried before. It was greater, even, than his time working as a sniper for his country. There had been some thrill to that, of course. He'd been one of the best snipers in his unit and he'd taken pride in that but bringing a man like Terry Clements to his knees and making him submit was so sweet and pleasurable that it was his latest hobby. He'd expanded his net to a variety of clubs because he didn't want people to realize what he was doing, so he'd had a variety of different Doms brought low before his prowess. And finally, at long last, Terry was in his sights.

The man had tried to wiggle out of his contract this morning, but Matthew had merely sent back pictures of the contract and the consequences for reneging. Terry was a businessman in the field of banking, he knew about contracts. In the end, Matthew felt a swell of anticipation as he watched the red luxury SUV drive along the nearly deserted road.

Laying atop what appeared to be a long-abandoned warehouse, Matthew watched through the scope of his rifle as the big man got out of his SUV and followed his instructions to a T. The second that Terry locked the collar around his neck, Matthew started a timer on his watch. Then he lifted his rifle once more, aimed, and fired. The tranquilizer dart left the end of the barrel in near silence and flew through the dark of the night, impacting Terry's neck with a precision that came from years of practice. With his hands cuffed behind them as they were, Terry couldn't even reach up to feel what had caused the sudden sharp sting to his neck. Matthew slid down the ladder he'd used to get to the roof and landed with a crunch on the gravel road, making his way towards his prey. The last thing Terry would see before the drugs knocked him out was Matthew dressed in his usual Dom leathers, crunching across the gravel with his sniper rifle slung over one shoulder as he pulled the night vision goggles from his face.

When next Terry woke, he would find himself in the most precarious position. There was a thick black blindfold over his eyes and noise-cancelling headphone over his ears, currently playing Rx (Medicate) by Theory Of A Deadman. His arms were splayed wide, held in place by leather cuffs around his wrists. His feet were equally spread and secured, leaving him helpless in a standing wide X with nothing keeping him up but the restraints around his wrists.

As his newest toy began to stir, Matthew crossed the room and set a large, beefy hand on the man's fine ass, giving it a squeeze. Then he lifted one side of the headphones so that he could say, "Welcome to my dungeon. I'll make sure you enjoy your stay." Then he released the headphones, making sure it fully covered his ear once more. Sensory deprivation was a good way to disorient a man. With his ears and eyes covered, all he had to rely on was what he could feel. Matthew had left the man's mouth exposed intentionally as well, wanting to reduce him to begging or pleading. He decided to start slow and began by rubbing down every inch of Terry's body with oil. His large hands were firm in the application, but also sensual. When he rubbed at his chest, he tweaked his nipples. He particularly liked fondling the man's ass. By the time he was rubbing the warm lotion over Terry's balls, his cock was straining hard against the bars of the cage that held it prisoner. The entire length of the cage disappeared between Matthew's hands as he rubbed warm lotion over it, delighting in the way precum began to dribble out the end.

 

[lthrbondage]

Terry felt the sting in his neck and reflexively tried to lift his cuffed hands to rub at it. When he couldn't he went to stand and the world spun. He realised that he had been drugged and took a step towards the presumed safety of his car. But the drug was taking fast effect and he fell, slumping across the boot. He tried to focus as he heard the crunch of boots and saw the fully leathered form of Sir B walking towards him.

When he came to, he couldn't work out what was going on. He shook his head to try and loosen whatever was covering his eyes, but it seemed securely in place. His arms were aching where he had been hanging from them, so he stood up and felt some relief as the tension slacked off. But he was unable to move his arms and legs back together, no matter how hard he tugged at the restraints. The music in the headphones was unfamiliar and stopped him from hearing anything around him. From the feel of air on his skin, he was still naked.

The touch on his ass made him jump "FUCK!" The damned music was stopping him hearing what was going on, so he was completely surprised when Matthew started rubbing oil into his muscles. He groaned at the feel of the warm oil as it was massaged in. He wondered what it looked like - his strong hair-covered muscles oiled up and slick. He flushed as he was always proud of his manly hair but then forgot about that as his nipples were tweaked.

"Ah, no, come on Matt, this whole thing is a joke - right?"

The silence gave him his answer as Sir B worked his way down. Soon his ass, cock and balls were being rubbed and he winced in pain as his cock swelled to fill the cock cage. To his surprise he felt precum start to dribble out of his cock. He realised what Matthew was doing and set his mind firmly against submitting. He tried to think of anything to make his cock relax, but it remained obstinately and embarrassingly hard.

 

[ShadowBinder]

"I never jest when it comes to love or war." Matthew retorted with a laugh, even though he knew that Terry wouldn't hear him. He abandoned his efforts to stroke the man's cock through his cage and instead moved around behind him and set his hands on the man's back, pressing his thumbs into the firm muscles of his back and kneading at the tense shoulders. His hands were surprisingly skilled at working tension from the man's muscles and he felt many of the knots relax and wondered how long it had been since these muscles had been properly rubbed down like this.

Once he had lulled Terry into a more relaxed state, his fingers instead found the man's arm pits and as they moved lightly over the oiled flesh, Terry gave an involuntary jerk from the ticklish sensation. Smiling wide, Matthew proceeded to spend some time finding all the ticklish spots on Terry's body, causing him to dance on the spot, trying desperately to get away from the tickling. Compared to the firm but relaxing massage he'd just been giving, this new torture would cause Terry to tense back up and by the time Matthew finally let up, Terry was panting from the exertion and overstimulation of his nerves.

Breaking a man took more than people might think, but Matthew prided himself at being skilled in that very skill. Now that he had worn down the man in a way he probably hadn't been expecting, he changed tactic again. Now he allowed Terry a moment to catch his breath while he cleaned the oil from his hands with a rag he had nearby. Then he opened the top drawer of his toolbox. It was a traditional toolbox one might see in a mechanic shop, but unlike at a mechanic shop, this one was full of sex toys of all shapes and sizes. He hummed to himself as he picked out a curved prostate massager, and a different chastity cage. He had instructed Terry to bring a cage with him, yes, but he hadn't been specific to what kind of cage. The steel one was great and he often used that style himself, but for his next bit, he required something different.

The first thing he did was use the key which he had gotten out of the boot of the man's SUV to unlock the cage and slide it off. He set it on top of his toolbox with the handcuffs Terry had put on himself, and then slipped the cock-ring portion of the prostate massager over Terry's cock before lubing up the device and pressing it inside of Terry. He didn't know for sure, but he was fairly certain that Terry had never left anyone play with his asshole before so the toy would be an unfamiliar stretch, but he had specifically chosen a fairly small toy so it wouldn't tear or otherwise hurt the man. Then he put the new chastity cage on Terry, securing it in place and affectively locking the prostate toy on him as well. It was more difficult to force his cock into the new cage since he was already swelling to quite a decent size, but after some careful maneuvering, he managed to get it tucked back into the tight confines. Even if Matthew released Terry from his bindings, there would be no way to remove either the cage or the prostate massager.

Stepping back to admire his handiwork, Matthew smiled and used his remotes to turn on the prostate massager as well as the electrostimulation of the chastity cage. Both toys had small batteries so he knew the charge wouldn't last terribly long. An hour, maybe two. The onslaught of pleasure would be impossible to escape, especially in his current predicament. Stepping back, Matthew took a seat on a nearby chair and began rubbing himself through his tight leathers as he watched Terry struggle with the pleasure that he didn't want.

 

[lthrbondage]

Terry groaned as Matthews thumbs worked at his tense muscles. Although Matthew was responsible for him being in this stress position, Terry felt grateful for the relief. "That's not going to work, you know." He knew what Matthew was up to and he wouldn't succumb to something as simple as that. The tickling left him on edge. The light, tantalising touches that he flinched away from. He wasn't a particularly ticklish person, but even so the light teasing caused him to flinch and jerk in the restraints, and set his already strained nerves jangling. he couldn't tell where Matthew was or where he would be touched next. His breathing grew harder and he could feel himself sweating.

He sighed with relief as the chastity cage was taken off - the weight was starting to hurt and it allowed his cock to chub up to where it wanted to go. He felt the ring around the root of his cock and then a pressing against his hole. "NO!" He strained against it, but couldn't resist as the object slid into his virgin ass. He clenched his teeth, expecting something huge and was surprised when it nestled in place. He relaxed. But when Matthews slick but firmed hands then stuffed him into another cage, he could not resist "Bastard!" His cock already filled this cage, but there was nothing he could do about it as his manhood was locked up again.

Standing there, blind and helpless, plugged and in chastity he could only wonder what he looked like. Then the electro started, small stimulants that caused him to jerk and twist in the bondage, while keeping his dick as hard as it could get in the cage . Terry groaned as the electro went on. It wasn't exactly pain, but it wasn't pleasure either. He could feel the constant drip of pre=cum as his dick revealed how much this was turning him on. Occasionally it would stop and he would groan with relief and hang in the restraints, only to jerk upright as it started again.

Time seemed to disappear. he had not idea how much time had passed, or how much time he had left. Surely this had been going on for hours. He started to ask "Hey...." and then stopped. He refused to show weakness to Matthew. He refused to beg. He clenched his teeth and tried to suppress the groan of pleasure as his ass was stimulated again and again.

 

[ShadowBinder]

Matthew walked over to one of the cameras he had positioned nearby and looked into the lens. Part of the contract Terry had signed consented to the recording of their session for pleasure and profit. Which meant that Matthew was free to live stream his session onto his popular BDSM website. For years he'd been posting videos online and made a decent side profit from it. It wasn't enough to let him quit his day job, but it was enough that it more than supported the purchasing and upkeep of his BDSM equipment. "For those of you just joining," he said into the camera. "This here is my newest play mate. It is, in fact, my proverbial white whale. The very man that inspired me to turn my attention to other Doms for my amusement. That's right, I finally caught him. As you can see, he's already begrudgingly enjoying himself. His body does look nice all oiled up though, doesn't he?"

He walked back over to Terry and ran a hand over the man's glistening hair-covered body. "Just like all my other play mates, he did sign a contract and consent to be here today and arrived of his own volition. However, I fear he didn't read the rules very closely. He's already broken two of them," he said with a smirk. Then he used a remote attached to the bottom of his left wrist guard to change cameras, knowing that his audience would switch from watching Terry to seeing the wall with the countdown and Matthew's rules written on the wall. The wall was directly in front of Terry but with his eyes covered, he couldn't see it, of course. Across the top of the wall was a large digital clock with six-inch tall red letters. They had started by counting down from 24 hours but currently read 01:02:08:53 with the seconds constantly ticking down.

Under the large digital clock were Matthew's four rules in blocky white letters against the black wall.

Rule 1: Profanity will not be tolerated. Any use of words like 'fuck' or 'shit' or the like will result in the penalty of an additional 1 hour added to the session.
Rule 2: Sir B will be addressed as Sir B, Sir, or Master during the session. Any other name or salutation shall result in the addition of 3 hours added to the session.
Rule 3: The session will not stop for any reason other than safety. Any pleas to 'stop' will result in the addition of 6 hours added to the session.
Rule 4: Absolutely no cumming during the session. Any orgasms, partial, full or ruined (precum does not count), will result in the addition of 12 hours added to the session.​

These were the four main rules that his viewers knew about because they were the ones that added time on to the session and they all loved it when Matthew's play mates, as he called them, broke these rules because that meant they would be getting more time to watch Matthew work them over. These rules and timer were the reason his 'guests' were blindfolded for at least the first few hours of a session. All of the rules were laid out in the contract they signed, but few of them actually read the contract so it was easy to tack on more time. One of Matthew's favorite parts of a session was removing their blindfold and revealing the wall and their remaining time, which was almost always more than the 24 hours they originally agreed to. Give a man a time limit and he will withstand it. If he knows he only has so long he needs to last, he can soothe himself with the knowledge that it will be over soon. However, once you reveal that the time limit is no longer valid, it's often a breaking point.

Matthew had started the 24 hour count down when Terry put on the collar, then he'd used drugs to knock the man out for almost two hours. After Terry had first woken up, however, he'd said the word fuck, followed by calling him Matt, which had earned him another four hours, bringing him back up to twenty six hours left on the clock.

He switched cameras again to the one he was standing in front of and said, "Now, he just called me bastard, what do you guys think that is, a violation of rule one and two at the same time?" He asked and took a glance at the comments, chuckling when most of his viewers agreed with him. "Alright, let's had four more hours to the board."

The time on the digital clock changed to 01:06:08:34 and then Matthew poured himself a glass of wine and made himself comfortable on his chair again, watching Terry as he played with his remotes. Sometimes he only activated the vibrating prostate massager, other times he only activated the electro stimulation on the chastity cage and sometimes he activated both. Switching them both on and off, low to high kept Terry on edge and he had no idea what was going to come next.

It was just over two hours later when Terry actually said something. Matthew glanced at the clock and saw that it said, 01:03:45:23. Though by his calculations, it had been just over four hours since Terry had fastened on his collar. It was impressive that he'd lasted two hours before saying something. It was clear from the noises he made and the way his body jerked around that his body was at least enjoying what was happening.

Turning off both devices, Matthew walked over to Terry and ran a hand over his chest. By now the oil had dried up and absorbed into his skin so he was more sticky than glisteningly smooth. "Now, my newest play mate here has always taken great pride in his manly chest hair. What do you all think, shall we give him a shave?"

He smirked, knowing that all this time Terry had been listening to music. He'd picked out a handful of songs he specifically wanted the man to hear, but then put it on ai dj mode. He glanced at his phone and smiled when he saw that Kryptonite by Three Doors Down was playing. That was one of the songs he had specifically picked himself. He put his phone away and walked back to his computer to read the comments from his fans. They were all giving suggestions but the majority were calling for Terry to be shaved bald. He laughed and shook his head, "I quite like the hair on his head, so that can remain where it is, but I will shave his body."

He went to his toolbox and opened a different drawer. This time he got shaving cream and a razor. He carried them to Terry and rubbed him down with the shaving cream first. Then he began to shave. Once more, Terry's failure to read his contract got the better of him. He had agreed to this treatment in writing. Matthew whistled while he worked and soon he had not only shaved Terry's chest and back, but he had shaved his arm pits, arms and legs. Then he knelt down and undid the chastity cage, pulling it off. Despite everything, or maybe because of it, the man's cock chubbed up almost instantly so Matthew couldn't help but give it a few strokes with his bare hand. Then he lifted it and used a belt around Terry's waist to lift it up and put of the way so that he could very carefully shave the mans balls.

It was a testimony to Matthew's work that despite the fact Terry clearly didn't like what he was doing, Matthew never knicked the man's skin. He was now smooth and hair-free everywhere but his head, without a single cut.

"Much better." He stated and then he walked away and cleaned his razor properly. He'd been dipping it in a bucket of water to clean it throughout the procedure, but now he was able to properly clean it, giving Terry a break for a few minutes.

 

[lthrbondage]

Terry was finding himself sinking into this as he imagined his subs used to do. He tried to fight it, but the repeated shocks and stimulus were taking their toll. He tried to keep his mouth clamped shut, but he kept gasping with surprise. He was determined not to beg, but after what seemed like hours, he let out a "NO!! Stop! please!" He cursed internally at his weakness, and determined not to speak again. That sneaky fucker was hoping for something like this and he would not let him win.

When Matthew started spreading shaving cream on his chest, Terry couldn't work out what was happening. At first he thought that it was more tickling and teasing and then he felt the rasp of the razor across his skin. He realised what was being done and he bucked in the restraints, his powerful muscles bunching with rage as he tried to pull free. "No!! Matthew, you fucker! Stop that!" The damn headphones stopped him hearing any reply and he could feel Terry slowly working his way over his chest, removing the manly pelt that he was so proud of. He knew what was coming next and felt his back, arms, pits and legs also stripped of hair. Terry wondered what he looked like - whether he looked like those pathetic slaves that were forced into rubber servitude. He couldnt - he was a proper man. But at the same time he was worried - what the fuck was Matthew up to?!?! Still, at least he wouldn't be able to do the crotch.

When the cage came off, Terrys cock swelled to its full length and stood proud in front of him, curving slightly up towards his washboard stomach. Terry groaned "No, don't do that, don't shave me there." He felt the shaving foam rubbed in and started to struggle, but the feeling of the razor pressed against his ball sac stopped him. Terry tried to stand as still as possible despite the occasional jolts from the prostate massager. He could feel the sure strokes as Matthew denuded him of his crotch hair. He knew what it would look like - bigger but also more childlike. Not like a mans dick at all. He slumped in the restraints at the thought, not seeming to realise that his cock was still rock hard in front of him.

 

[ShadowBinder]

Now that Terry had been shaved hairless - save for his head - Matthew walked to the camera again. "Let's do a quick count here, shall we? He told me to stop, twice," he held up two fingers. "That's already twelve hours. Then he called me by my name," he held up a third finger. "That's another three hours, and he called me a fucker, which is a two-fer. He just broke five rules in quick succession. In a matter of what, five minutes he earned himself another nineteen hours. Let's see that time now." He said and switched cameras to reveal the clock again.

01:22:39:57

"Lookie there!" Matthew said with a laugh, "He's almost up to two days. I don't think I've ever had a play mate tack on so much time so quickly without cumming. Alright, time to get him washed off, then I'll see if I can make him cum." He said and then he picked up a hose and turned it on. The spray of water that impacted Terry's freshed denuded body was cold and harsh. It certainly scrubbed away all the soapy residue from the shaving foam, as well as any remaining oil. In fact, by the time Matthew turned off the water, the man's body was pink from the combined cold and abrasion of the water.

Setting the hose back down, he walked to Terry and ran a large hand over the man's chest. Goosebumps had formed all along his flesh and his nipples had hardened and his cock had mostly deflated. The blindfold was now clinging to the man's face but the music would continue to play. The headphones were water proof and Matthew hadn't directly impacted them so they remained firmly in place.

He circled around the dripping wet man so that he stood directly behind him and pressed his hips up against him from behind. His own cock was rock hard and he ground the leather-clad member against the man's cold, wet ass where the prostate massager was still doing its job. His arms wrapped around Terry and gripped one nipple in each hand, gently pulling and twisting them even as he ground against him from behind. Leaning in he pressed his lips to the man's neck and sucked on his flesh. Between the warm oil rub down, the shave and the bitter cold rinse off, Terry's flesh would be raw and sensitive.

After a minute, Matthew's right hand roamed down Terry's body, across his beautiful washboard abs, and got a firm grip on his balls, pulling them downwards. His left hand then followed the path of his first one and wrapped around his cock, slowly starting to stroke him. The cold water had been enough to cause the natural male reactionnof shrinkage, but Matthew was delighted by how quickly the cock stiffened in his hand.

He ran his tongue along Terry's neck before releasing his balls to reach up and move the headphones again. "How well did you read the contract you signed?" He asked with amusement as he switched hands, his dominant right hand begining to stroke Terry properly while his left hand began playing with one of the man's nipples.

 

[lthrbondage]

Terry looked around blindly, his headphones and blindfold making him feel more vulnerable. His newly shaved body was chill in the air of the room and he started to shiver. As the hose hit him, he yelled angrily, and thrashed as much as he could in the restraints. " BASTARD!!!"
When the water stopped, he hung there, wet and cold and so it was almost a relief when he could feel Matthews body pressing close against him. The warmth of his body through the leather made Terry unconsciously lean back against him, enjoying the feel of the leather against his skin. he could smell the man behind him - that rich smell of leather that he was so familiar with.
He could feel Matthews rock hard cock through his leather jeans and as it pushed against the prostate massager, the feel of the item pushing deeper inside him made him groan.
Terry seemed to be completely sensitized to the slightest touch. He was making small noises of pleasure despite himself and even before Matthew grabbed his cock, it was starting to grow again.
The combination of pulling his balls down and stroking his cock very quickly brought Terry to the point of release. He could feel his balls churning as Matthew whispered in his ear.
The contract? Why was he talking about the contract? Terry desperately tried to remember what he had signed but it was all a blur. His mind raced, distracted as he was by the expert hand working his dick. When Matthew started to twist his nipples as well, Terry knew he would not be able to resist for very long.
He could feel that his dick was already leaking precum and he hoped that Matthew would give him a break so that he could pull back from the climax.

 

[ShadowBinder]

Once again, Matthew added on four more hours when Terry called him a bastard. It was enough to send the time over two days, which delighted him.

It was that surprising when Terry pressed his cold, wet body back against him. It was clear that he was trying to warm up and the familiar feel of leather behind him was probably something of a comfort to him. The feel of the man's heavy cock in his hand told him that Terry was already getting close to the edge. It wouldn't take much to send him over and make him release his load all over the floor.

It had been close to five hours since Terry put the collar on, but you wouldn't know it by looking at the time on the clock, which was now double that of when they started. Reaching up, he removed the man's headphones entirely and tossed them onto his nearby toolbox. Then he reached up and undid the blindfold, removing it for the first time.

Now that he could actually see, Terry would find himself in a large, open room. Behind them (for Matthew was still pressed up against his backside) was a wall. Along the wall was a work bench and a couple tool benches, all made of metal. The floor they stood on was subtly slopped towards a pair of drains, one three feet away on either side of where they stood.

In front of them, however, on the far side of the room was the black wall painted with Matthew's four rules and the clock. Between them and the wall was a large seventy-two inch television. It displayed the live footage of the five cameras set up around the room. The main picture was an almost straight on view of Terry with Matthew behind him. Then in the four corners of the television, were smaller pictures showing feed from the other four cameras. One was directed at the wall, but the other three had different angles of the two men in the center of the room. Matthew knew that the main image on the television was what was being broadcast to his live stream but at any minute he could switch to show any of the cameras feed.

Wrapping his arms around Terry, he allowed the man to see the remote on his wrist as he entered a command and the camera ( and subsequently feed on the TV) zoomed in on Terry's face. He wanted to capture the man's reaction to the set up, but most especially to the clock and the large rules underneath.

02:02:23:48

He allowed the man a moment to let his eyes adjust and take in the room and the rules, then he pressed his lips against his neck. One hand began toying with the man's nipples while the other began to expertly stroke his cock. "Go ahead," he whispered into Terry's ear. "Cum for me, slave, doing so will let me keep playing with you for another twelve hours."

 

[lthrbondage]

Terry blinked as the blindfold was removed and looked around for the first time. While checking out the room, he also looked down at himself - the hairless front that he could see, his dick standing out straight from a hairless crotch. Damn, what had Matthew done to him?

He looked at the display in front of him and realised that he had already broken the rules several times - the damn clock showed that. 2 days!! Fuck!! He then looked at the camera feed - he had never thought that Terry would be such a sneaky bastard as this.

It was clear what Matthew was after now, and Terry clamped his jaw shut and tried to think of anything to stop the increasing arousal he was feeling. He desperately tried to hold back, but he could soon feel his balls churning and despite his best efforts, he came, spurting cum across the floor and over Matthews hand.

"Dammit!" It came out before he could stop it and Terry let himself hang limply in the restraints for a moment before standing up and staring into the camera, waiting for whatever Matthew had planned next.

 

[ShadowBinder]

When Terry came, his whole body tensed and spurt after spurt of thick white cum coated Matthew's hand and the floor in front of them. He let out a deep chuckle. "There, now don't you feel better?" He asked and he reached up with both hands. One hand held Terry's head still while the other forced his mouth open so that he would wipe the cum on the man's tongue. Considering everything he'd done to Terry so far, Matthew feared the man may very well try to bite his fingers so he was quick to pull them back after he'd had a taste of the salty release. He wiped what was left on his hand all over Terry's now clean-shaven chest. Then he wrapped both arms around him again and adding more time to the clock. "You came and you used more profanity. That's another thirteen hours, Terry." He taunted and glanced at the new time.

02:15:18:14

"Two and a half days, that's how long I get to play with you now. I think I can break you in that time. As it stands I'll have to have you call into work on Monday to let them know you won't be there, maybe even Tuesday at this rate. How much longer are you going to drag out this session for me, hmm? You have complete control over how long this lasts. If you had read your contract, you'd know that."

Stepping away from Terry. he looked at the camera and addressed his audience. "I think it's time to step him up on a few things. He's already cum once, but a man like him, I'm sure he's got more in him." He said and he groped Terry's balls, feeling how heavy they were. Then he returned to the man's backside and pulled the prostate massager off, removing it from around his cock as well. "Anyone have any suggestions?" He asked and walked over to the laptop nearby to read the comments. "The common consensus is that I should put you in a new position and give you a break. Seems your audience is feeling rather generous today."

Setting the toy on a tray to be cleaned later, Matthew began going through the drawers of the toolbox What he came out with a humbler with wrist restraints. Returning to Terry, he released one of the cuffs holding the man's hands up and away from his body and before Terry had much of a chance of fighting back, he inserted it into the humbler device. Then he manhandled the man's balls into place, not seeming to care too much if he caused the man some discomfort or pain in the process. Finally he released the other hand and secured it into the other wrist spot on the humbler and locked the device closed. "Your balls are right there for me to do whatever I want with them. And your hands are so close, but far enough that they can do nothing to protect them." Matthew teased and he smacked the man's balls just to prove his point.

 

[lthrbondage]

Terry clamped his mouth shut, but Matthews fingers forced his mouth open and he could feel the cum being wiped on his tongue. He flushed with humiliation and glared at Matthew. The man was clearly waiting for a response, but Terry was not going to risk any more penalties.

When Matthew groped his balls, Terry tried to pull away, only to realise just how much he was powerless in his current position. He knew that Matthew was right - they were still loaded with cum and he was going to have to be very careful if he wanted to avoid another 12 hour penalty. He groaned with relief as the prostate massager was removed. With that stimulus gone, he was feeling more sure of himself and more confident.

He then saw the humbler that Matthew was holding. "No, come on, Maa..... Sir. That's not fair, is it?"

Terry didn't really expect a response. He considered trying to resist being cuffed into the humbler, but he had signed a contract - he would at least obey that. His hand was locked into the humbler and he then felt Matthew lock it around his balls. He winced as a fold of skin caught in the humbler, but managed not to swear. Then his other hand was trapped. His hands were now locked in front of him, his balls pushed through the humbler with the skin pulled taut over them.

"Oww, ...sh..., I mean OWW" Terry flinched away from the slap on his balls - but his ankles were still restrained, so he nearly fell over backwards. He dick was pressed upwards behind the humbler and his calls were very vulnerable. He clenched his fists as he tried to pull out of the humbler, but all he managed to do was pull even more on his balls.

"Ok, ok, you're right, I can't protect them. but please dont do that again"

 

[ShadowBinder]

"Don't do that," He slapped Terry's balls, "again?" He asked with a laugh. He loved how Terry was trying so hard not to break his rules now. He had realized he was only digging his hole deeper and changed Matthew's name into Sir, which ironically enough almost made it sound like he was saying master. "Ok, I won't do that," once more he smacked Terry's exposed balls. He wrapped an around around the man from behind to keep him from topling over backwards.

He pulled away and glanced at his watch. "Well shoot, would you look at the time? I have a session with a sub at the club so I gotta get going. Looks like you'll get that break after all. Here, let me at least get something for you to sit on." He said with a grin before walking over towards the wool bench. He pulled out a stool that had a dildo secured dead center on it.

Moving over to Terry, he set it under the man then knelt down and secured the stool in place with locks built into the floor. Even if Terry manages to somehow kick the stool, it would remain in place. Not not he could move his feet enough to reach it in the first place. Then he poured lube all over the dildo. If Terry's legs got too weak and he needed to sit, he would impale himself on the dildo.

Then he walked back over to the work bench and produced a milking machine. Returning to Terry, he got it set up in front of the man, also securing it to the floor. It was positioned so that he was able to slide the head of Terry's cock into the sleeve of the milking machine. Then he tied a rope around the man's taut balls and looped the other end around the base of the milking machine, pulling it tight. Now if Terry tried to pull back enough to pull his head out of the milking machine, he'd be tugging on his own balls.

Reaching up, Matthew grasped Terry's chin and turned his head to look at him. "Don't worry, I'll be back in three hours. Four, tops." He said and then he turned on the milking machine and turned as if he was going to leave. He to ok his time leaving though, he wanted to see what Terry would do or say before he left.

 

[lthrbondage]

Terry winced at the slap, but managed not to cry out - he wouldn't give Matthew that satisfaction. The second slap made him grunt between his clenched teeth and he glared at Matthew.

Terry looked around to see what Matthew was getting and he blanched as he saw the dildo. As Matthew put it in place, he twisted as much as he could to see what was going on. He recognised the ploy at once - as he tired, he would try to sit down. Terry locked his legs - he could last for quite some time.

The milking machine! Oh damn - he knew there was only so long he could resist that. He had drained several slaves dry using a similar device and he knew it was impossible to resist. Initially he grinned as he thought that Matthew had set it up wrong. But then he realised his mistake. He could pull the tip of his cock out of the suction of the milker, but it would yank on his balls, causing him pain. He would have to alternate between letting the machine arouse him, and pulling back to prevent cumming. And he knew that it would get more difficult as time went on.

Terry was barely aware that Matthew had stopped to watch. He was already concentrating, feeling the milking machine working on his cock and massaging it back to full size. He left it as long as he could before pulling backwards, his balls stretching out in front of him. The pain helped his cock to relax, and he then relaxed himself and allowed his cock to slide back inside the sheath.

It seemed like he was keeping this up forever, constantly getting to the edge of cumming and then pulling back. As time passed, he became aware of a constant ache in his legs and his knees started to tremble. This time, when he pulled back, he felt something pushing against his ass - the damn dildo! His muscles were slowly weakening and he was crouching lower. For some reason this wasn't helping with the milker and it was driving him nuts. Terry was sweating now - which made the sheath even more slick inside. With sweat dripping down his body, Terry felt one of his feet slip slightly, and suddenly the tip of the dildo was inside him.

He stood up immediately, but doing so pushed his cock deeper into the sheath and he could feel himself close to cumming. He pulled back, letting out a groan as his tortured balls complained, and as he did so, he could feel the dildo. Terry realised that the only way to keep his cock out of the sheathe, was to submit to the dildo. Terry braced himself and relaxed his knees, feeling the dildo pushing inside him. He let out a yell as it shoved inside his virgin hole and he had to pause to breathe deeply before sinking further. Slowly, slowly he relaxed until the whole dildo was stuffing him and he was sat on the stool. Ironically, the invader in his ass made his cock harder and he still had to try and pull out of the sheath before he orgasmed.