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It was about a month after Hiccup had lost a fish-catching contest to Toothless and been punished, and Hiccup's ass was _still _sore. He had been fucked to high hell, pissed on, cummed on, inflated, tortured, denied, ballbusted and generally screwed with. He had been meaning to get back at Toothless, but had been recovering and been busy with various tasks.

"That dragon is so in for it today." Hiccup muttered to himself in the morning of 30th day after his punishment.

"Toothless!" He called, while walking out the door.

The kinky bastard of a dragon jumped down from his rooftop perch and nuzzled against Hiccup.

"How ya doin today Hiccup?" He said.

"Completely better, no thanks to you." Hiccup responded. At this the dragon grinned.

"Let's go, I need to show you something." He added, as he clambered onto the Nightfury and they flew in the direction of the cove.

When they landed, Hiccup led Toothless in the direction of a large, well-lit cave, with a few fish at the entrance.

"What's this?" Toothless asked, gobbling up the fish.

"Just a little fun." Hiccup replied.

"What da ya mean fuunn?" Toothless asked, his words starting to slur.

"You'll see." He responded, grinning devilishly at the thoughts of what he was going to do.

"Uh-hu?" Toothless muttered as he fell unconscious from the sleeping powder, placed strategically in the fish.

---

About two hours later, Hiccup finished off his last knot and stepped back to admire his work.

Toothless was bound, vertically spread eagled on a metal frame that Hiccup had built while he was recovering, front paws above his head and back paws below him. His wings and tail were bound, as not to damage them, but out of the way. He had a large ring gag in his mouth and a spreader bar on his legs, as well as his saddle removed and a tank of water strapped to his back instead. Beside the frame sat a pile of tubes, pipes, ropes, bindings, tools and other kinky objects. Toothless's cock was partially out from its sheathe, and his testicles hung heavily at about the size of cantaloupes.

Just then Toothless woke from his slumber, looking groggily around in confusion at what was happening and where he was.

"Whu-whu theee fuuk?" He garbled out, trying to escape the expertly tied knots.

Hiccup temporarily removed the ring gag so Toothless could speak to him.

"What the fuck is this?" Toothless said to Hiccup.

"Some well needed revenge." He responded.

"Wha-what are y-you going to do?" Toothless asked nervously, thinking back to what he did to Hiccup, and secretly hoping for the worst.

"You'll have to see." Hiccup replied with a wink.

Hiccup replaced the gag, this time in the form of a normal gag with a tube attached.

"This gag is linked to the water tank on your back, so you don't get thirsty." Hiccup said. "Now, time to get into it!".

Hiccup started by tickling Toothless's body, from his ribs to his paws to his crotch to his cock, making sure he was nice and sensitive all over. He then started working on Toothless's sack, as the dragon squirmed in discomfort, from the relentless tickling. All of a sudden Hiccup brought his fists swiftly up into Toothless's seed-swollen testies, smashing them up against his pelvis and making the dragon moan in pain. Hiccup repeated this 3 or 4 more times, mashing his plums against his now rigid cock, the dragon moaning each time. Hiccup then switched to using Toothless's ball sack as a punching bag, alternating between testies for a long period of time. After that, for about an hour, Hiccup started squeezing his balls, bringing a new level of pain to the table. At this point the dragon was moaning and whining in pain, writhing and trying to escape.

"Tsk-tsk." Hiccup muttered. "Trying to escape are we?" At this Toothless shook his head vigorously, hoping to avoid more torture.

"Well you know what happens when you try to escape." He said as he thought back to how Toothless had ballbusted him for trying to escape then denied him relief.

Hiccup then brought a vicious kick to Toothless's sack, pulverising his orbs once more and making him yowl in pain as he repeated the kick a load more times, just to properly tenderize the sack.

"Hmm, enough of that." Hiccup said, just then noticing the precum dripping from his cock.

"About to cum are we? Hmmm? Naughty dragon." He said giving Toothless a disappointed look, while Toothless was secretly loving the sheer domination Hiccup was showing.

"I have just the solution for that." Hiccup said, fiddling with a latch on the side of the frame.

Toothless looked on in painful confusion as Hiccup finished fiddling with the latch. Suddenly Toothless felt the frame creak and bend, as the built-in hinges did their job, bending him over himself. By the time Hiccup was finished, Toothless was bent over his own crotch, his fully erect cock to the side of his face, and his bruised balls hanging beneath him. Hiccup then replaced the water gag with another ring gag, with a latch on the side of it, opened up Toothless's maw and inserted his own cock deep into his throat.

"Time for you to get to know how it feels." Hiccup said with a smirk as he clamped the ring around the base of the dragon's knot, locking the huge dick in his throat.

Hiccup then started tickling Toothless balls again, pinching and nipping to bring the dragon that little bit closer to orgasm. Finally Hiccup gave the balls one last huge slap, as Toothless tensed and came. Seed gushed in massive spurts, straight down the reptile's throat, and filling his mouth with the backwash of cum. Spunk continued to gush from his cock and into his stomach for a full 8 minutes, before it even started to taper off. At the end of the mighty orgasm, Toothless's belly was inflated to huge proportions, and cum was dripping down his face from his nose.

At this point Toothless was half delirious with pain/pleasure, and really needing to empty his bloated bowels. Hiccup then quickly attached a pipe from the dragon's ass to his mouth, so all the seed he ejected would imminently be consumed again and if he came again or pissed, he would have to swallow that as well.

It was now dark, as the human had been torturing the dragon for most of the day, so Hiccup started the next part of his plan. He setup a previously built device below Toothless's balls, that would bring a crushing leather fist into his balls every hour, forcing him to cum at least once in the night.

"Right, I'm off for the night." Hiccup said with a sigh. "Hope you enjoy!" He added, before leaving the bound dragon hanging in the cave.

As Toothless saw Hiccup leave the cave, he wriggled painfully, trying not to release his bowels, thinking about all the lewd things that Hiccup was still to do to him, which caused him to accidentally relax, releasing the floodgates of his ass. Cum flowed from his inflated belly, out his ass, up the pipe, and back into his mouth. Thankfully the semen was nice-tasting, so the experience wasn't all bad. As he continued to eject the cum, he heard a ticking noise and the contraption under him, launched a leather fist, straight up, and into his mashed balls, further adding to the pain. It was going to be a long night.

---

Hiccup woke in the mid-morning, feeling refreshed after a relaxing sleep. He stretched and gathered his things, then set off towards the cove. When he arrived he heard the faint sound of murring and groaning from the cave as Toothless was pushed towards wit's edge. Hiccup walked into the cave to find a very inflated but drained looking Toothless.

Toothless's night had been very miserable, never quite getting to sleep due to the punching contraption and his own cock. His balls were swollen to almost twice their original size, and extremely tender. He had been constantly swallowing cum for the past 3 hours, after he had orgasmed for the 5th time at least, also some of his golden piss was circulating through him, adding a saltiness to the mix. There was a large puddle of cum beneath him from leakage from his nose, and his bowels were crammed with dragon spunk.

Hiccup looked upon the sorry-looking dragon and walked over to him.

"Think its time to relieve you?" Hiccup asked him.

Toothless only nodded in response and snorted out more cum from his nose.

Hiccup then undid the metal ring from the dragon's knot and almost immediately fluids squirted out his mouth. Hiccup then re-latched the frame so Toothless was spread-eagled again, and cum spewed from the dragon's mouth and onto the boy. Hiccup was then thoroughly doused in cum/piss, making for a warm sticky morning bath, to which he smiled and licked some of it up. He then lifted the wooden cover off a meter wide by 3 meter deep hole, dug directly beneath Toothless and removed the tube from Toothless's ass. Cum immediately started dripping out his ass and into the hole, then a drip turned into a dribble, then a dribble into a gush, until cum was pouring into the hole.

Over the next hour, Toothless ejecting most of his cum into the hole, with Hiccup pushing on his stomach for extra pressure. By the end of it, Toothless was panting and moaning, and the hole was filled completely with warm, bubbling, cum/piss mixture. Toothless balls were as swollen as ever and his ass was gaping slightly, his eyes were dazed, and his cock was still rock hard from his immense sex drive.

Hiccup then reached into his bag and brought a container of salve, then applied it to the dragon's swollen testicles, making sure to properly lather them up.

"Wha-what's that-at?" Toothless stuttered out, wincing in pain as his tender plums were fondled.

"Healing salve for testicular trauma." Hiccup replied.

Almost immediately an intense warn feeling washed over Toothless, completely erasing the pain and quickly shrinking his balls back down to their regular huge size, and also making the bruising disappear.

"Ahhhh ohhhhh mmmm." Toothless said. "That stuff is really good."

"Well without it I wouldn't have recovered so quick, and wouldn't be able to continue with the next part." Hiccup said.

"Wha-what-t do y-you mean n-next part?" Toothless stammered out fearfully.

"Don't worry, I'm pretty much finished with the ballbusting bud."

"If you're a good quiet dragon, I won't replace the gag, but if not..." Hiccup said while cradling the dragon's orbs.

Toothless nodded vigorously at this, fearing for his fragile sack, and making a mental note to shup up.

For the next part Hiccup stripped completely naked, throwing his clothes to the side and switching his metal leg to a rounded cylinder for better stability. He then carefully tied a strong rope around Toothless's cock and sack, making sure to tie it tightly but gently. Then he dunked himself in the cum filled hole, also covering Toothless's ass in cum and making sure to lube up his arms.

Next, Hiccup lowered himself down to his dragon's ass, and started licking the sides erotically, leading to his slightly gaped pucker. He then put his hand into a fist and slowly pushed it into the dragon's anus, then his other hand. Now that he was elbows deep in his dragon, Hiccup started feeling about for the prostate, which would be about the same size as an orange and wrinkled. Finding it, Hiccup started expertly massaging it, starting only by rubbing softly and lightly prodding.

Meanwhile, Toothless was confused at the new feeling, never having explored his anus before, writhing and groaning at the pulses of pleasure coming from within his groin. Hiccup then started to speed up his ministrations, pushing harder and rubbing faster, to push the dragon towards orgasm.

"Hiccup, I think I'm gonna..." Toothless murmured to his rider.

"That's fine." Hiccup responded, secretly grinning at what was about to happen.

As Toothless got nearer and nearer to orgasm, Hiccup rubbed faster and harder, unable to contain himself at what was going to happen next. All of a sudden Toothless came. But nothing happened. Toothless had been eagerly awaiting the release when the ropes around his groin denied his orgasm, making for a very uncomfortable feeling of denial, and pent-up-ness. Hiccup continued rubbing and prodding, adding some light punches and slaps to the mix for extra pressure, while the dragon whimpered in pleasure but yet not able to hit orgasm.

About 5 hours later, Hiccup finally stopped hitting the dragon's prostate, for he was totally spent. He had rubbed, massaged, punched, squeezed, used his feet on, pummelled, slapped and generally abused the dragon's pleasure centre. Toothless, on the other hand, was on the verge of consciousness, after being denied for such a long time. His ass was gaped from Hiccup fisting him, his cock was straining and throbbing, his balls were pulsing and swollen once again, and his body was writhing in denied pleasure.

"H-Hiccu-up p-pleas-se l-let me c-cum." Toothless stammered out in a whisper.

"Well, I guess you deserve it." Hiccup replied, with another grin.

Hiccup then got up and walked over to the pile of tools. He picked out a metal rod with a ring on the end and a tapered point. He then walked over to the Nightfury and gently pushed the tip of the rod into Toothless's pee hole, then all the way down, effectively plugging his penis. Then Hiccup untied the rope from Toothless's cock and balls, and started stroking his cock erotically and fondling his sack. Toothless was so close to orgasm that he came right there on the spot, his balls expanding as they produced fresh seed. But there was a problem. Toothless didn't seem to be able to cum, but he was still orgasming. It was the worst sensation Toothless had ever felt, cumming but not producing any cum from his penis because of the plug. As this continued the dragon growled and whimpered and yowled in pleasure/pain, as his balls were not able to release any of the pent up cum.

By the end of it, Toothless was a panting, sweating, drooling mess, passed out and hanging from the frame. Hiccup smiled at this and finally removed the plug from the dragon's penis, allowing a pouring of cum to be released. Cum continued to drip from is cock for the next 15 minutes, creating a warm sticky pool below himself, and allowing his balls to return to normal once again.

About 30 minutes later, Toothless woke up to see Hiccup drinking down his cum, for a nice refreshing lunch, and looking up at him in content. Before Toothless could speak Hiccup replaced the gag on Toothless and put the final part of his revenge into action.

Hiccup started by tying rope around the dragon's sensitive testicles, around each orb and around the sack, then attached a huge wooden bucket to the ropes, sitting it on a stool for now. He then attached a long pipe from the a hole in the ceiling, to the bucket, securing both tightly. Next he grabbed a large wooden carving, which was in the shape of a massive butt plug, he had made and attached a tube through it and to the dragon's cock, creating a slight suction on the cock end. Hiccup then walked over to his dragon's gaped ass and lubed up the plug with cum and slowly started pushing it into the dragon's ass, causing him to moan as he was stretched around the plug. When the plug popped in, it created a tight seal with the anus, allowing fluid in, but not out. Finally Hiccup attached a pipe from the bottom of the bucket to Toothless's mouth, checked everything was right and remove the bucket from the stool, putting a light pressure on Toothless's sack.

"Ok, I think I'm done." Hiccup said. "There is a large reservoir of water above this cave, which is where that pipe leads from. When I release the valve, water will start flowing into the bucket, putting pressure on your oh-so tender balls. To relive the pressure you have to drink the water, which in turn, will fill up your bladder and make you pee into your own ass, effectively giving yourself a pee enema." "Got it?" He asked.

"Mmm-hmm." Toothless responded, already realising that it was up to him about how much pain he would be in.

"Here we go then!" Hiccup said, opening the valve on the pipe from the ceiling, letting a flow of cool crystal clear water flow down it and into the bucket.

As the bucket filled up, Toothless quickly gulped down the water, as not to re-ballbust himself again. Toothless continued to gulp down water, which started filling up his bladder, making him need to pee. After 10 minutes Toothless released his bladder for the first time, yellow piss streaming from his cock, down the pipe, and into his ass. Toothless blushed in humiliation, as his own hot piss filled him up, starting to distend him.

At the 2 hour mark, Toothless was quite bloated from being filled with piss, the bucket was about a quarter full, despite his best efforts, and his bladder was at bursting point, making him release again, moaning as he was filled more and more. Hiccup sat on a wooden chair nearby, snoring happily and dreaming about Toothless lewdly spread out.

Two hours after that, Hiccup woke up to find a significantly more bloated Toothless, whimpering as the bucket filled more and more, and he peed once again, causing him to make gurgling noises as he was filled up. Finally, one more hour after that, the bucket was touching the floor of the cave, stretching Toothless's ball sack to its limit and causing any movement to be a extreme pain. The dragon was now almost constantly pissing into himself and his nose was starting to drip a little, and he had long since lost control of his bladder. He was whimpering and moaning and gurgling, when Hiccup decided to remove the gag to see what was going on and how the dragon was holding up.

"Hiccup-Ahh, m-my-my balls are gonna p-p-pop!!" Toothless squeaked out, feeling a warmth in his throat.

"Also I-I-I AHh, think I'm gonna pu-." And with that Toothless threw up.

Out of his mouth came a torrent of golden piss, throwing Hiccup back and instantaneously soaking him, as Toothless continued to vomit piss. His cock throbbed in unison with his spewing, as his belly started to de-distend, getting rid of all the piss. At the end of it Toothless was a sodden, coughing mess, balls stretched to their limit and stomach empty.

Hiccup then removed the plug and released Toothless from the frame, who flopped out, accidentally smacking his testicles off an outcropping of stone, making him cry out and whimper as he finally cradled his pulverised plums. Hiccup then propped his dragon up against the wall and the two of them fell asleep.

An hour and a half later, the two woke, Toothless still cradling his crushed orbs, Hiccup blinking the piss out of his eyes.

"Oh my gods, t-that was intense, but deserved." Toothless stated.

"Couldn't agree more bud. " Hiccup responded. "But now time for your reward for surviving."

"Reward?" Toothless asked.

"Yes." Hiccup said, as he crawled over to Toothless, rubbing his sheathe, to bring out his cock once more.

"Ohhhhhh, that's it." Toothless said as Hiccup rubbed and stroked his cock, lathering it with precum.

Hiccup then positioned his own ass above the cock and slowly sank down on it, moaning as he did so.

"Ahhh, never gets old." Hiccup muttered, sucking in a breath as he worked his way up and down the cock.

"Ohh-Ohhhh." Hiccup gasped out as Toothless bounced his lap, pushing more cock into Hiccup.

"AAH!" Hiccup yelped again, when Toothless gave a particularly hard thrust, slamming 4 more inches of thick cock into him.

At this point Hiccup was being bounced on Toothless cock, pulling out and slamming down each time, as Hiccup's balls were squished between his own butt and Toothless's thick knot. Toothless was grinning devilishly at this, making sure to crush the boy's balls extra hard.

"OHHH, AHHH!! OWW!" Hiccup yelled, as Toothless pulled his cock almost completely out and slammed it all back in, this time pushing past the knot and right down to the balls, the last yell from Hiccup's own balls being crushed by the hard bone of the dragon's pelvis.

Toothless then, thinking back to how Hiccup had punished him, pulled the boy completely of his cock and slammed him down again on the knot. He did this for a few more minutes, each time slamming Hiccup past his knot and mashing the human's testicles. Finally Toothless slammed Hiccup down one last time, the dragon's knot expanded locking the two together , and Hiccup's testies between them and they came in unison, Hiccup whimpering and Toothless roaring, as they both squirted cum in vastly different amounts, Hiccup on to Toothless's body, Toothless into Hiccup's belly.

Toothless then lovingly wrapped his wigs around the two of them, as he continued to pump hot dragonseed into Hiccup, who was moaning in happiness and pleasure, thinking about how kinky his dragon was.

Hope you enjoyed, make sure to leave a comment! ;)

-GriffonTail