Jason Masters

Todd's Bad Deal

Part One

Todd lay on his back in the seclusion provided by the surrounding bushes, busily working on once again introducing the friend who'd never leave him to Rosy Palms and her five daughters. It felt good, and Todd's fertile imagination made it even better.

The day was warm and Todd had deliberately dressed in only shorts, brief underpants and sandals. He'd taken his usual equipment, crossed the property line onto the abandoned property and quickly found his usual spot where, shielded from any intrusive eyes, he could act out some of his most exciting and most private fantasies.

First, he had tied his legs, at both the ankles and just above the knees, imagining how exciting it would be to have someone else forcibly tie him up. Then, Todd had slowly and sensuously pulled first his shorts, then his underpants down as far as they would go and folded them down over the rope tied above his knees, imagining all the while that he was fully bound and someone else was deliberately forcing this oh-so-naughty exposure upon him.

Well before Todd finished pulling his shorts and underpants down, his little cock was fully erect with both the excitement of his erotic imagination and the anticipation of what was to follow. Todd took hold of his erection and began the familiar motions, masturbating himself slowly and surely toward climax.

Todd had been able to 'shoot' quite early in life, but Todd didn't care. All he cared about was the wonderful feeling that rubbing his nine-year-old dick caused inside him. Today, he'd decided not to squirt into a handkerchief. He'd allow it to land on his chest and tummy instead, just as though someone who didn't care what he wanted had wanked him and forced him to cum all over himself! The naughtiness of this thought spurred on his libido even more.

Fully engrossed in his sexual fantasy and the accompanying activity, Todd didn't notice the quiet footsteps as someone approached his hiding place, possibly to investigate the rhythmic noises coming from within. Just as Todd climaxed, at the worst possible instant when Todd was beyond the point of no return, the bushes parted and a tall young man stared down at Todd who immediately began to climax all over his chest and belly just as he'd planned to do, albeit not publicly like this.

Even amid his sexual pleasure, Todd was instantly mortified. This was terrible! Someone had caught him at last, and there was no way for him to hide what he'd been doing; no way to explain it. He couldn't claim that someone had forced him to do this, since he was alone. In a panic, Todd began to sit up and grab at his shorts even as his still-erect cocklet finished spurting the boy's semen onto his chest.

Quick as Todd was, the man was faster. He grabbed Todd's wrists before he could take proper hold of his shorts and then pulled Todd's arms away and outward, stretching Todd's arms apart. This had the dual effect of rendering Todd helpless and of lifting him off the ground and near to the man's face. He glared at Todd.

"What are you doing on my property?" demanded the man. Todd just stared at him, unable to answer. This man owned the land Todd was on? Todd had thought it to be abandoned. And as to what he was doing… well, that was rather a rhetorical question since the man had obviously seen what Todd had been doing. Since there was nothing which Todd could possibly say, he said exactly nothing, staring into the man's annoyed face and blushing deeply at his own humiliating exposure.

The man looked down at the semen still wetting Todd's chest and tummy and said, "So, having a wank I see." His gaze travelled further down before he added, "And tying yourself up, too." Todd could only blush even deeper, his face almost beet-root red with shame.

"So, you like being tied up, do you?" said the man. He cast a glance around and grabbed a spare rope which Todd had brought but not used yet. "Well, let's see how you like this!" With that, the man pulled Todd's arms down behind his back and, holding onto Todd's wrists with one hand, turned Todd around then began wrapping the rope around his wrists, tying them securely together behind Todd's back.

Todd's mind was in a whirl. Could this man do this? Did he have the right? Todd wondered if he should call for help, but the knowledge of his current indecent exposure caused him to quickly abandon that idea. Todd stayed silent as the man took another spare rope and quickly tied Todd's elbows together as well before turning the frightened boy around and pushing him down onto the ground again.

"Don't move!" growled the man. He rummaged in one pocket and pulled out a small digital camera. Turning it on, he aimed it at Todd, who began to instinctively curl up to hide his almost-limp dick, but the man immediately slapped his legs. "I said, don't move!" the man growled, menacingly. Todd allowed his legs to be straightened out and then lay still, his face even redder with the shame of the thought of being photographed in such an acutely embarrassing condition.

"Evidence, for the police," explained the man as the flash went off. "You're a trespasser and I want evidence of what you were doing here, so everyone will know what a dirty little boy you are." Todd stared in horror as the man moved a little to one side and the flash went off again. Todd could only lie there in despair as the man moved to another position and for the third time the camera flash announced the capture of Todd's humiliation for posterity.

Todd was next hauled to his feet and made to stand still while the man took more pictures of him from both the front and the rear as well as side-on and, it seemed, every angle in between.

The camera evidently had a 'macro' close-up mode since picture after picture was taken of parts of Todd's body. His face; his cum-splashed chest and nipples; his cum-soaked tummy; his now-limp penis and his bottom.

Todd was even made to bend over to be photographed from behind and his arse-cheeks were then pushed apart to expose his anus for another photograph. Nothing private was left hidden from the camera's implacable eye. Todd could only stand there, completely ashamed of himself and of his humiliatingly total exposure.

There was a pause. Todd didn't dare look around to see what was happening, but after a minute the man grabbed the rest of the ropes Todd had brought with him and, taking hold of the ropes around Todd's elbows, hoisted the boy into the air and walked out of the bushes, carrying the boy by the ropes around his arms. Todd's embarrassment was renewed as he was forcibly removed from his final shred of cover.

Still Todd didn't dare say anything as the man walked through the surrounding trees. Todd didn't know where they were going and he didn't care a lot. His whole mind was on how exposed he felt with his shorts and underpants still pulled down to just above his knees.

After what seemed to Todd to be a very long walk, they arrived at a fence with cleared land beyond. The openness of the area again renewed Todd's shame as the lack of concealment made it all the easier for anyone to see him with his dick on display.

Then the man began to tie a rope around Todd's neck. Thinking he was about to be hanged and die, Todd began to cry. He didn't hold out any hope of mercy or believe that begging would do any good, so he just cried.

Todd managed to control his crying when the man, instead of throwing the rope over a branch to hang him as Todd had feared, instead pushed him against a tree, face outward looking at the cleared land, then tied the rope around the tree trunk so that Todd could not move away from the tree.

Another rope was tied around his bound arms and around the tree, making it impossible for Todd to turn around. Then a third rope was secured to his tied ankles and stretched out to a fence-post where it was tied off. Now, Todd could not slide around the tree to the opposite side to hide himself from view if anyone happened to enter the cleared land.

"I'd better see what the police make of this. You'll be safe enough here until I get back." The man turned and walked away into the trees, leaving the bound and effectively naked small boy tied inescapably to the tree with his semen drying slowly on his chest and tummy. After he'd gone, Todd finally allowed himself to cry freely.

The indecency of his exposure made him far too ashamed to call for help.

Todd cried. He looked back and forth. They were the only two actions available to him.

He was tied to a tree, unable to move any part of his body except his head more than a tiny distance; his shorts and underpants were down around his knees and there were shiny patches and streaks of his own dried cum glimmering on his bare little chest; and so he cried.

He was terribly afraid of someone finding him like that and his parents finding out that he'd been tying himself up and masturbating, hence he looked around to see if anyone was watching him.

Nobody came, either to deride him or to help him.

It had been ages since the man who had caught Todd quite literally in the act had left him there, helplessly tied to a tree with his private parts on display. Todd didn't know exactly how long he'd had to wait, but the shadows had moved quite a bit before Todd heard footsteps approaching. He froze in fear. Was it the man, or someone else? Which would be worse? The man had mentioned calling the police because Todd was trespassing on his land.

It was the man. He walked up to Todd and glared at the quaking boy.

"The police say that it's a civil matter, so it's up to me whether or not to charge you," he announced. Todd stared at the man, hoping that this was good news.

"I'd rather not see such a small boy get a record with the police, so I'm willing to offer you a deal. If you agree to the deal, I not only won't have you charged, but I also won't tell anyone about you masturbating and tying yourself up on my land."

Todd felt some relief, but he wondered what the deal was. What would he have to do in exchange? He wasn't long kept in ignorance in that matter.

"You must agree to come to me whenever I want you to, and to do anything and everything I tell you to do, forever." Todd stared in disbelief as the man went on, "I'll only keep your secret if you agree to this deal. Otherwise, your parents get to know everything you were doing here today, including seeing the pictures I took of you as evidence, and I may even decide to have the police charge you with trespassing, too."

Todd still stared at the man, feeling a knot of dread in his stomach. He knew he was caught. He didn't dare take the risk of his parents finding out his dirty little secret. It was too shameful; far too shameful. This man had caught him, and now he had to pay the price. Todd nodded his head in agreement.

"Say it out loud. Look directly at me and tell me that you agree to always come to me when I want you, to always do anything and everything I want, and that this agreement lasts forever." The knot of dread in Todd's stomach seemed like lead as he looked at the man and recited his promise.

The fish had been hooked and landed. It was soon to be gutted as well. It would not take Todd long to discover that he had made the worst deal of his life.

Part Two

The continuing story of Todd's bad deal with the man who caught Todd tying himself up and masturbating. Is it only Todd's imagination which leads him to believe that there is someone staring at him from behind?

Todd stared at the man, the knot of dread in his stomach seeming to rise up to almost choke him. What had he done, making that deal?

But there had been no real choice. Todd was sure of that. He couldn't let the man tell Todd's parents how he had been found not just trespassing on the man's land but even, quite literally, caught in the act of climaxing from masturbating after having tied his own legs.

Todd wasn't certain exactly how his parents would react to receiving that kind of news, but he was certain that it would be extremely bad for him. The man had threatened to tell them unless Todd made a deal with him.

Todd had agreed to the deal. He would come to the man whenever he wanted Todd, and Todd would obey him, doing anything and everything the man wanted, forever. Todd knew it was a bad deal, but believed that he'd had no choice.

Todd was an honest child. He intended to keep to his end of the deal, partly to keep his 'dirty little secret' from getting out but also from a sense of fair play. He'd made the deal and now he had to stick to it, no matter what happened. Besides, Todd believed that he probably deserved whatever bad things the man decided to do to him.

Todd had tried to give up his habit of masturbating and found it impossible, and he loved to tie himself up for it. Sex and being tied up. Two of the most forbidden things Todd could imagine. He would take his punishment. Todd was certain that he'd hate what the man was going to do to him, but he believed it was just what he deserved.

The man began to untie Todd from the tree which he'd been bound to while the man was thinking about what to do with Todd. Before the deal had been made.

Todd made no attempt to escape, even when his legs were finally untied. Besides, his arms were still tied behind his back so tightly that it was becoming painful, so there was no way for him to pull his shorts and underpants back up. Todd now bitterly regretted ever pulling them down in the first place. He was far too ashamed of his nakedness to run away with his privates still on display.

The man reached for Todd's shorts, and at first Todd thought that he'd pull them up again for him. Instead, the man roughly yanked both Todd's shorts and underpants all the way down and off him, leaving Todd naked. Not that it left Todd any worse off, except for the psychological effect of knowing that he was now even further away from getting any relief from his shame than before.

As the blushing boy watched, the man tied a loop in a thin piece of rope then put the loop over Todd's penis, pushing it all the way down, behind Todd's balls. Then the man tightened the loop until it was uncomfortably snug around Todd's boy parts before tying a knot to keep the rope tight. The other end of the short rope was tied into a non-slip loop.

The man gathered up Todd's clothing and the untied ropes. "Come on." It was a simple order and the man began to walk away, holding the loop at the end of the short rope. Todd wasn't quite fast enough and yelped as the rope tugged painfully at his boy parts. The man ignored him. Todd scrambled to trot quickly after the man, to avoid any more pain.

After walking for what seemed to Todd like a long time, they came to a clearing. Todd could glimpse a house, not quite hidden behind some trees on the other side of the clearing. But what caught his full attention was the device in the middle of the clearing. Todd gaped at the device, his mouth hanging open in astonishment. He'd seen one in a history book and had found the idea fascinating, but he'd never expected to see one in real life.

It was a pillory. An ancient punishment device, designed to hold a person's neck and wrists enclosed in wood so that the person could be exposed to public ridicule. But this one looked quite new. Even the tightly-packed earth around the legs looked to have been freshly tamped down. The wood was smooth and didn't have the greyness of old wood which develops over time.

Todd could only stare at the pillory in horror as he was led to it. He knew what was about to happen to him. He could barely believe it, but he knew all the same.

As he came closer, Todd noticed the poles set into the ground some distance apart from each other on the side of the pillory closest to the house. Each pole had what looked like two leather straps, one close to ground level and the other some distance higher off the ground. As he was led around the pillory to the same side as the poles, Todd tried to imagine what the poles and straps were for but failed.

He was not long kept in ignorance. The man untied Todd's arms at last, which was a relief to Todd since they had been hurting him a lot, and then, opening the top arm of the pillory, pointed to the appropriate points while saying "Neck, here. Wrists, here and here."

Todd didn't pretend ignorance. Shaking with fear, he crouched down until he could rest his neck and wrists in the appropriate half-circle holes in the bottom half of the pillory. The top half was lowered gently but quickly, trapping Todd in the pillory. There was a 'click' as the man turned the staple-lock, ensuring Todd would remain trapped in the pillory.

Todd felt his right leg seized and pulled outward until it touched one of the poles which Todd had noticed earlier. His leg was secured firmly to the pole with one strap around his ankle and the other around his calf, just below the knee. Then the procedure was repeated with Todd's left leg. Todd was almost dazed with disbelief. The idea of resisting at this point was only a mad, random thought, quickly dismissed as useless.

The man untied the rope from Todd's boy parts and stood up.

"You have my permission to struggle or call out if you want to."

Todd barely heard the man walk away. Partly it was the soft, short grass the man was walking on muffling his footsteps, but it was also Todd's preoccupation with his rising panic as he began to realise the position he was now in.

He had been pilloried! Naked!

Worse than mere nakedness was the position Todd was now in. He was almost squatting, with his legs widely spread apart and strapped in that position. Todd knew without a doubt that all his most private parts – bottom and anus, penis and testicles – were now on obscene, obvious display to anyone behind him.

The man had said he had permission to struggle so Todd began to twist his hands and pull on them, trying to find a way to slip them out of the enclosing wood; to try to escape this obscene pose.

It did not the slightest good. The size of the holes in the pillory had been chosen cunningly. They were just comfortably big enough for Todd's wrists, but nowhere near big enough for him to slip his hands through no matter how hard he struggled and pulled.

Todd tried yanking at his legs next, but the posts stood firm, forcing Todd to keep his legs spread widely apart and his privates to remain on lewd display.

Todd tried jerking back and forth in the pillory, to try to loosen something. Maybe he could pull the posts out of the ground so he could at least stand up? That would be something.

But it was a wasted effort. The posts had been placed deeply into the earth and the dirt and clay was packed tight around them. They didn't move.

Todd finally struggled frantically in every way at once, trying to jerk the pillory loose, or pull his hands out or get his legs free. Anything to escape this horrifyingly humiliating position! All he succeeded in doing was chafing his wrists. Both the pillory and Todd's position remained unchanged.

Todd cried for a minute or two as the hopelessness of his situation overwhelmed him. Crying helped relieve his feelings for the moment, but did nothing else. Then, a new sensation began to make itself known.

He was being watched! Somehow, Todd could feel that he was being looked at.

Someone was observing him from behind. Someone was silently laughing at his shameful exposure, his humiliating position, his inescapable helplessness. Was it the man? Todd had no way of knowing if it was him or someone else, or even if there was really anyone there at all.

Unable to see anything behind him because of the pillory, Todd tried to dismiss the feeling. He hadn't heard and still couldn't hear anything except the rustling of the leaves as a light breeze blew through the surrounding trees. There was no clue to any of Todd's five senses that he was anything but totally alone. Yet, somehow, through what some might call a sixth sense, Todd became more and more sure of his unseen observer, enjoying his distress and exposure.

Someone behind him was watching Todd. Of that, he felt certain.

Todd screwed his eyes shut and clenched his hands into fists as he wept with the humiliation. He was sure that someone was enjoying staring at his private parts.

Todd began to squirm with shame, desperately trying to find some way to remove his privates from public view. As before, it was an impossible task.

"Stop looking at me!" shouted Todd.

There was only silence, but Todd now had the feeling that he'd done exactly what the unseen observer wanted. He'd only succeeded in humiliating himself further.

Todd began to wriggle and squirm with renewed vigor. Todd felt even worse because he could not be sure, by anything but this feeling, that there was even someone there. He might be alone and shouting to nothing for all the real evidence he had.

Again, that feeling of being observed – of having someone unseen drinking in his humiliating nakedness – overwhelmed Todd, defying his senses and logic.

"Please," moaned Todd, "stop looking at me."

Silence.

Todd sobbed and wept, still wriggling and squirming the small amount possible to him in the pillory.

"Please. No more! Please stop. Please!"

Only the whispering trees gave their rustling reply to Todd's earnest pleas.

"Don't look at me!" wailed Todd, feeling those unseen eyes boring into his shamefully exposed anatomy.

And still there was nothing in response.

Todd could feel the unseen observer's eyes fixed upon him. Obviously whoever it was had no intention of paying any attention to anything Todd said. He gave up pleading and simply wept, desperately hoping and praying that this silent, overwhelmingly humiliating observation of his privates wouldn't go on for much longer.

Todd would get his wish, but it would come when he was tipped out of the frying-pan and straight into the fire.

Part Three

The final episode of the story where Todd suffers even more, although his final torment is far more subtle than all of his previous tortures.

Todd wept. It was the only thing he could do.

He'd already tried yelling and begging, but that had only made him feel even more ashamed about his situation. He'd struggled his hardest but had made exactly no progress toward escaping. Under the circumstances, weeping was all Todd had left, not that it did him any more good than struggling or yelling.

Inescapably trapped in the pillory, naked with his legs spread wide apart and strapped to posts so that his private parts were shamefully exposed, Todd wept and mentally begged whatever powers may exist to somehow rescue him from this shame, little though he believed he deserved such rescue.

Having been caught just a few hours earlier (was it really so short a time? It felt like days) masturbating to orgasm after tying his own legs together, by the man on whose land he had inadvertently trespassed, Todd firmly believed that he'd had no choice but to make a deal with the man, to obey him always, in order to prevent his dirty little secret from being revealed.

He was slowly beginning to realise that it was like making a deal with the devil.

Todd still had that feeling as though someone was silently watching him. He had not the slightest evidence of this. It was only a feeling but it was strong, and it made him feel incredibly ashamed to believe that someone was staring at his private parts from behind him, out of his sight. He desperately wanted it to stop.

Then, it stopped, suddenly and terrifyingly as a footstep sounded, quite close behind Todd. Remembering how silently the man had left earlier, Todd had no way of knowing whether he'd been there all along or had just returned.

For that matter, Todd wasn't certain that it was the man, but he wasn't long left in doubt as the man spoke.

"Now, it's time to punish you for real."

Todd had no time to contemplate that statement. He had practically no warning except for the brief 'swish' of something slicing through the air just before a strip of skin across his buttocks erupted into agonising pain

For long moments, Todd could not even breathe, let alone make a noise.

Then he drew in breath and screamed.

Todd had no idea what the man had hit him with, but it hurt like nothing Todd had ever felt before. The sheer magnitude of the pain had overwhelmed him for a short time. Now he had recovered just enough to scream, over and over.

As the pain began to fade, Todd's screams became less frantic, but immediately another blow, just as painful as the first, swiped across his bare bottom causing Todd to scream anew. Todd wasn't capable of screaming any louder, or he would have.

"You're making too much noise," declared the man, and suddenly a large rubber ball was thrust into Todd's mouth, gagging him and muffling his screams. Straps were buckled behind his head, holding the ball in place.

Then the beating resumed.

Over and over Todd was struck on his naked behind with whatever implement the man was using. The beating was done slowly, methodically and cruelly. Just as Todd began to recover from the agony of one blow, the next landed. Todd's screams were still audible but were well muffled by the gag as the beating went on and on.

The blows were administered evenly over Todd's behind, some of them even landing on the sensitive area between his buttocks and his thighs. How Todd could possibly experience even worse pain was a total mystery to him, but obviously he could since those blows hurt the most.

Finally, when Todd had reached a state where he could only whimper quietly and desperately into his gag, the beating stopped at long last. The man's footsteps retreated. Todd was left with nothing but his pain and misery for company.

More time passed. The pain in Todd's buttocks gradually receded from unbearable to mere agony. From time to time, Todd struggled without any real hope of escaping. It was just as well that he didn't get his hopes up since his struggles made not the slightest difference.

Even more time passed and, when Todd's pain had retreated to the point of being merely severe, he heard the footsteps approaching again.

Then Todd felt someone touching his limp penis. He didn't dare protest, even though he felt totally humiliated by this.

Todd felt something cold touch his penis. It felt like metal. Something slid over his penis – something which didn't feel solid; it was more like rings of metal. Gradually his penis slid into the rings, then the head of his penis was pushed through another ring which lodged just behind his glans. Todd could feel some kind of adjustments being made, then something cold and metallic gripped him firmly behind his testicles and after a bit more adjustment, there was a very positive-sounding 'click.' Todd heard the person behind him stand up.

Todd's legs were finally released from the posts and then the pillory was opened. Trembling, Todd stood up, his limbs free for the first time in hours.

The man stood there, looking at Todd with an expression of casual disdain on his face.

"You live at…" and the man recited Todd's address, "… right?" Todd nodded, not daring to touch the ball-gag in his mouth without permission.

The man undid the buckles and removed the ball-gag, then held out Todd's clothes to him. Todd took them, wondering what was happening. Was his torment over at last?

"Put them on." Todd obeyed, looking down at his penis during the process. To his shock, he could see that it had been enclosed in a cage-like device of shiny metal, but with the pain still burning fiercely in his bottom, he didn't dare ask any questions about the device.

Once Todd was clothed, the man took him around the house and down a hill to the front gate where Todd was told to turn left and he'd find himself at his own front gate a little way down the street.

Todd was given instructions before he could leave: He was to return just as soon as he wanted the penis cage (the man called it that) removed, but he must be prepared to say exactly why he wanted it removed, clearly and without trying to hide what he meant. He would also have to come early in the day and be prepared to stay away from home all day.

After being dismissed, Todd walked slowly back home, his bottom still burning. He would have rubbed it if he'd dared, but he was sure that even the slightest touch would renew the pain. Even the rubbing of his underpants against his skin was painful right now.

Inside the house, he avoided his parents and went straight to his room, there to strip his clothes off and lie face-down, naked on his bed and cry while he waited for his bottom to feel better.

Todd found it difficult to sit on his tender bottom at the table for the evening meal with his parents, but somehow he managed it and to fend off his parents' remarks about him fidgeting at the table. He took a warm shower which seemed to help his bottom a little before going to bed early. Exhausted by the things the man had done to him that day, Todd slept well once he decided to lie on his side instead of his back.

By the time Todd woke in the morning, his bottom felt a lot better. He could still notice some pain, but it wasn't too bad. He also had a raging erection. Naturally, his hand went down to it, to provide himself with his usual morning relief.

Todd's fingers immediately encountered the penis cage, still locked firmly in place.

It took Todd almost an hour of probing and struggling, trying to remove the penis cage, before he realised that it was impossible for him to remove it without removing his penis and testicles with it. He also realised, with despair, why it was on him.

The penis cage allowed Todd to go to the toilet.

The penis cage allowed Todd's penis to become erect.

The penis cage made it quite impossible for Todd to provide himself with the sexual relief he so desperately wanted.

Todd knew that, sooner rather than later, he was going to have to go back to the man.

He wasn't looking forward to it.

The End

I intend to some day do a new story about Todd and 'the man', but this is the end of the current arc.