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One fine morning on the Isle of Berk, Toothless, the Nightfury, was walking through the woods, to meet a friend.

"Toothless!" A voice said from around the corner of a tree.

"Clarence! Been a while!" Toothless replied, sitting back on his haunches and looking at the large Terrible Terror that had just rounded the corner.

"Let's just cut straight to the chase." Clarence said, swishing his tail from side to side.

"I agree." Toothless replied, reaching round to his side where a bag hung.

Out of the bag Toothless pulled a wooden carving, something that resembled a medium sized and intricately carved butt plug.

"Here you go." The bigger dragon said, putting his paw out with the toy on it.

"Thank you!" Clarence said, reaching for the toy, but Toothless pulled his paw back.

"But I think a little payment is required." Toothless said.

"P-Payment?" Clarence asked nervously, as Toothless never usually asked for payment for this kind of thing.

"Yeah, this one took a bit longer to make and I'm in need of a bit of a release. Don't worry, it'll only take a few minutes." Toothless said.

"Hmm, if its quick, then ok." Clarence said begrudgingly.

"Ok, then, I'll just get to it." Toothless said, rubbing a paw on his sheathed cock, bringing it out a little so he could pee.

"Open your mouth please." The bigger dragon said to Terrible Terror, who by normal standards, was much bigger than usual.

"Grr, fine." Clarence mumbled, putting his mouth around the first few inches of Toothless's cock.

"Ahh, there we go." Toothless said, releasing the floodgates of his bladder, which he had been holding in all day and was about to burst.

"That's it, just swallow, it'll be over soon." Toothless said soothingly to Clarence, as he whined around Toothless's cock, swallowing the hot, steaming, and yellow urine reluctantly.

After about a minute of pissing, Clarence started to pull off Toothless's cock, his belly slightly bloated from all the piss. As soon as he tried to pull off, Toothless put a much larger paw on the back of his head, pushing the smaller dragon back on to his cock. To this, Clarence flailed and tried to pull off, Toothless only tightening his grip on Clarence who was now whining and groaning under the assault of piss.

Two minutes later, when Clarence was significantly more bloated, Toothless's stream started to taper off, his grip on Clarence loosening a little. Clarence immediately pulled off Toothless softening penis, vomiting up huge amounts of dragon piss, his belly still severely distended.

"You dick." The bloated dragon growled, grabbing the butt plug from Toothless and waddling off into the forest, urine still leaking out his mouth.

"Nice seeing you too!" Toothless called after him, laughing to himself about the joke he had just pulled, and walked back out of the forest.

---

About four hours later, Toothless was eating his lunch of fish at the waters edge on the beach side of the island, gulping down the last of them, and about to go for a nap, when he noticed a weird purple thing wriggling on the far side of the beach. Intrigued, he padded over to it, now looking like it was some sort of limb. He prodded it, and it retreated a little, then made a beckoning motion towards an overhand a little bit away, the appendage now slithering towards the overhang. Toothless followed it out of curiosity, getting to its source, the most bizarre thing he had seen in a while.

"Woah." Toothless said, looking at the sight in front of him.

About three meters in front of Toothless sat a writhing purple mass, about twice the size of him, and with purple tentacles sticking out at odd angles. As Toothless looked at it in bewilderment, two eyes and a mouth smiling filled with teeth appeared, looking back at the dragon.

"Hello there little dragon." A voice said, coming from the purple blob.

"Who the fuck are you?" Toothless said, his teeth appearing in an instant.

"Just a friend of a friend, looking for a good time." The thing replied, a tentacle slithering towards Toothless.

As the tentacle slithered towards Toothless, he let it do its thing, as he knew that his residual musk made a lot of creatures want to mate with him, being an alpha and all. When the tentacle reached him, it hesitated for a second, then advanced towards his crotch and slit, the tip slowly working his cock out.

"Ooooh, yeah, that's the spot." Toothless muttered, closing his eyes.

The tentacle continued its job digging Toothless's cock out, but unbeknownst to Toothless, another tentacle, this time with a rough ball of tentacles on the end, advanced towards him as well. While the first tentacle worked at his cock, the new one flattened itself on the ground below Toothless's groin, and then in a swift sudden movement, thrust upwards into the dragon's low hanging testicles. As the tentacle ball slammed upwards, mashing Toothless's balls, his eyes blinked open, and a wailing moan escaping his lips.

"Oooooooooh!" He moaned, automatically getting into a defence position on all fours, as the ball reared for another strike.

Unfortunately, his current defence position left his balls a little undefended, and he realised this the moment before the ball re-collided with him. With three times the power this time, the tentacle ball, rocked up into his plums, instantly pulverising them again, and even lifting him a foot off the ground.

"Ungf!" Toothless wailed out, paws reaching for his testicles as he fell forward.

Almost instantly a new tentacle shot out, opening up and spraying a fine white mist onto his unprotected face and nose, the knockout liquid quickly putting him to sleep.

"Now for the fun to begin!" The tentacle blob cackled.

---

Half an hour later, Toothless woke up, his predicament distracting him from the stinging ache in his groin.

The black Nightfury was suspended vertically about six meters in the air by purple tentacles attached to each limb, tight vines wrapped around his chest to keep his wings in check. His cock was mostly retreated into his silt, balls now hanging heavily, with more tentacles hovering ominously below, as well as some positioned at his ass. The tentacles all came from the purple tentacle monster thing who was grinning at him, pleased by his handiwork. They seemed to be located at the entrance to a cave, still under the overhang but a little more to the side.

"Wakey wakey, my little dragon bitch." The purple blob said.

"Uhhhg, w-where am-m I?" Toothless mumbled, waking up from his forced slumber.

"Your in my humble home, little dragon." The blob replied.

"Don't call me that!" Toothless growled, struggling in his bonds.

"Now now don't speak to me like that." The blob said in an irritated tone, a thick tentacle whipping into the dragon's testicles, causing the dragon to whimper in pain.

"Now, my name is Mike, and I am what you would call a 'tentacle monster'. You will do what I say, or you will be punished. A friend of mine had a rather unpleasant experience, which is due to you. So you might call this a bit of revenge from a friend of a friend! Understand?" He said.

"Clarence? That little snitch!" Toothless muttered, then reluctantly said "Yes." To Mike.

"Sorry, what was that? I think the little _bitch _forgot to say sir. And I think that deserves some punishment." Mike said, grinning like the devil himself.

As he finished speaking, tentacles started to warp around Toothless's balls, wrapping around the top and each ball, Toothless struggling all the while.

"Ah ah ah, don't struggle." Mike said, the tentacles suddenly tightening, and the ball of tentacles hovering below Toothless's sack.

Without any warning at all, the ball slammed into Toothless's testicles, mashing them up against the constricting bonds, the dragon yowling and writhing in pain, his balls getting thoroughly busted, again and again. After about two minutes of busting, the tentacles stopped, Toothless whimpering and on the verge of throwing up.

"Now you know the punishment, don't misbehave." Mike said, as Toothless responded reluctantly with a "Yes, sir.".

"Right, I'm in need of a bit of a release so to speak, to time to deal with it." The blob said.

Just then, a new set of about six or seven tentacles emerged and positioned themselves over Toothless, and started to flow with a blue tinged liquid which smelled of fish. The fluid cascaded over the bound dragon, covering him from head to toe, and then on to the ground. After this went on for about 10 minutes, the stream tapered off, a sodden Toothless shaking his head to clear it of the piss. As Mike finished, a tingling sensation was left on Toothless's skin and muscles, covering his entire body and alighting his senses. As he unconsciously tried to cradle his balls again, he found that it took a huge effort to even lift his paw, which got harder as the seconds ticked by.

"I see you getting accustomed to my urine. You see, it relaxes and weakens the muscles making it very hard to move, but at the same time it greatly increases sensitivity as well as keeping you awake which makes for lots of fun!" Mike said, sounding excited.

"Ohh, godhh-ss fuchingh dammm-hit." Toothless slurred, it getting harder for him to speak because of the piss.

"Now now, don't you swear at me." Mike said, the tip of a tentacle caressing his balls, Toothless gasping out at the sensation. It felt like some one was using multiple hands, but ten times more sensitive, and that was just from a light touch.

"So you see if you misbehave, then it will be one hell of a lot more painful for you." Mike said. "Now for the fun to begin!".

Before the words had even left his mouth, thicker tentacles had emerged from the mass, coiling towards Toothless's ass and muzzle, the defenceless dragon incoherently trying to speak. Toothless let out a groan as the tentacle near his ass, tapered from an inch to about four inches wide, started to push in, as well as the one at his muzzle clamping onto him and entering his throat with a thickness of five inches. The one in his throat started to secrete a pre like substance, a little salty but kind of sweet. However, the one in his ass had started to thicken, spreading his hole wider, to just under seven inches, and delving deeper, crushing up against his prostate.

At this point Mike was letting out little moans and saying things like, "Yeah, that's it!" and "Take my thick cocks, you dirty little slut!".

As he was saying this, the tentacle in Toothless's ass started to thrust, now at a foot and a half long and eight inches wide, ploughing Toothless's hole and deforming his belly a little. The tentacle in his maw had also started to thrust, pumping out more sweet-salty pre that acted like an aphrodisiac, bringing his eighteen inch cock with knot included fully erect, another tentacle approaching and wrapping around, starting to suck on the dragon's cock. Toothless himself was moaning and grunting, unable to form proper words, both due to the urine and the treatment he was getting.

As the dual thrusting continued, the tentacles worked themselves deeper, the one in his ass now at his lower stomach and the one in his maw now passing through his lower throat. At the same time, the tentacle on his cock pulled off and another one, smaller this time, at about half an inch, poked its way into Toothless's cock, the dragon squirming in discomfort. The tentacle worked its way down his urethra, the bumps and ridges lining it sending spikes of intense pleasure through Toothless. When the tentacle passed the one foot mark, precum started leaking out of the little reminder of space that was left, from being backed up.

All of a sudden Toothless let out a drawn out whimper as the urethral probe finally breached his bladder, having worked its way all the way down his cock, the other tentacles now starting to speed up with their thrusts and then tentacles around his balls tightening their grip. While Mike muttered out his degradations of Toothless, he unconsciously sent tentacles to his balls, to caress and jab and poke at them, which added spikes of pleasure pain to the mythrid of sensations the dragon was going through.

After about two minutes more, Mike started to reach his limit, giving a few more erratic thrusts before starting to pump into Toothless. The tentacle in his ass suddenly stopped, and started to pump thick purple slime deep into his bowels and stomach, while one in his throat also started gushing gelatinous slime into him. At the same time, the tentacle probe in his bladder grew a little thicker inside, and also started cumming, albeit slower, but still making for a feeling of discomfort as Toothless's bladder was filled, all the while Mike groped and grabbed the dragon's balls, which would have been significantly painful if he had not already been overrun with sensations.

Five minutes later, Mike started to taper off, leaving a panting bloated Toothless, crammed with tentacle slime. His stomach and lower bowels were full, his belly bulging outwards slightly from all the cum, unable to escape due to the tentacle still crammed in his muzzle and stretched ass. His bladder was completely full, the dragon now having the feeling of really needing to go to the toilet, but not able because of the urethral plug, and his balls were stinging and tingling, wrapped in a death grip from the intense orgasm. The dragon also would have cum, but he had to experience it without the release, from the still remaining urethral tentacle.

"Ahhhhhhh, that was sooooo good! Don't you agree?" Mike humorously asked the bloated dragon.

"Mmmff." Toothless weakly replied.

"Welp, doesn't matter, cause its time for stage two!" Mike said. "Stage two??!" Toothless thought to himself.

At that, Mike simultaneously pulled the three tentacles out of Toothless, purple cum immediately gushing out of his maw and ass, cum also dripping out of his cock from his full bladder. After mostly emptying out his ass, the dragon's purple dripping anus gaped a little, his cock still emptying itself, and a little cum still dripping from his mouth. Due to the paralysis, he still couldn't move much, but he did manage to contract his anus, feebly trying to block any further attacks.

Mike then sent tentacles advancing towards Toothless maw and ass again, a different type of tentacle, sort of sucker shaped, approaching his erect cock while the tentacles around his balls released. The tentacles at his mouth and ass were thinly tapered to six thick inches, ribbed all the way along and very long. They penetrated easily, pushing through his used bowels and throat, both entering his stomach at the same time, and to his surprise, continuing on to the opposite ends.

With a final push both tentacles popped out either end of Toothless, being twice penetrated all the way through, which was a decidedly new sensation for the dragon. As they thickened to stretch his ass and maw, the other tentacles holding him up released, because he couldn't really escape due to the paralysis. Now, he was hanging from dual tentacles going through him, limbs handing limply by his sides.

Next, another tentacle moved towards his ass, this one much thicker an much more ridged, which started pushing its way into his ass, purple slime being used as lubricant, and as it pushed in, Toothless's ass was stretched even further, now to nine inches, the tentacle fully wrapping around his sensitive prostate. All of a sudden, the tentacle at his pleasure centre opened up and latched on, causing Toothless to moan out and writhe, bouncing slightly on the thick tentacles running through him. Immediately, the tentacle started to suckle and squeeze Toothless's prostate with relentless brutality, at the same time as another latched on to his cock to milk the dragon of his seed.

For the next three hours Toothless was unyieldingly tortured, his cock, for the second time ever in his life, milked dry, and at last the tentacles stopped their sucking. Toothless's prostate was now swollen from the sucking, and his cock was still erect, balls empty, although they would quickly replenish. The dragon was physically drained too, mostly due to the suspension tentacles constantly gyrating inside of him.

"You must be exhausted my little cumslut." Mike said, his voice slightly mocking.

Toothless could only nod weakly in response.

"Well, once again, I don't care anyway, cause its time for stage 3!" He said.

"St...Stage....Thr-ee?" Toothless managed to mumble out.

"Yeah, bitch!" Mike said, "I'm not the only one who gets a piece of you."

With that, Mike rolled along the ground, Toothless being manipulated by the tentacles to follow him, hovering. About a minute later they were in the cave, now seeming much bigger than before.

"Well well well, what do we have here?" A new deep booming voice said.

"A little toy for you, Rein. Been enjoying him for hours." Mike said

"I can see that." Rein replied. "Can you hear me little dragon? Or has Mikey's piss had too much effect on you?".

"I...can. N-now...fuck....off." Toothless managed to get out.

Rein chuckled. "I won't fuck off, but I will fuck you. And I will warn you, I'm a very different ride from Mikey here." He said, emerging from the darkness.

Rein was more formed than Mike, looking faintly like a dragon, but with the same type of eyes and mouth as Mike. He was a darker purple than Mike, an his tentacles were more refined and tucked away in his body, rather than flailing about, and he was also much larger, probably four times the size of Toothless.

"Now, to business. Mikey, give him to me." Rein told the smaller blob. To which he replied with, "Sure, enjoy him." Sliding out of the cave.

As he finished speaking, Mike quickly pulled the tentacles out of Toothless, much faster than the dragon would have preferred, rippling through his insides and out both his mouth and ass. His maw was left filled with purple slime, his ass too, but also gaped and twitching.

"Now, I'll get straight to the point." Rein said to Toothless, who was now sprawled on the ground trying to empty himself of Mike's cum. "You pranked my friend, Clarence, and he asked us to do a little something for him, and this is it. I myself don't beat around the bush like Mikey, if you misbehave then you will suffer." He said, a lightning fast tentacle shooting out of him and slamming down onto Toothless swollen testicles, crushing them against the ground and holding them there, causing the dragon to cry out in pain. "But if you behave, then you might just enjoy it." Another tentacle reaching out to pat the dragon's head, not that he noticed anyway.

Rein then easily picked Toothless up, tentacle attaching to each limb to once again suspend him, now upside down over Rein. Toothless was then lowered down to what appeared to be a slit in Rein's body, Toothless's face being pushed right up against it, the tip of something emerging.

"Ahh, its been way too long. Which is probably bad for you." Rein said, just the tip of his cock filling Toothless's maw completely because of how ridiculously thick it was.

As the seconds ticked by, the cock in Toothless maw grew and grew, becoming longer and longer, while still retaining that insane thickness, growing to fill his mouth then down his throat, almost blocking off his airway. A few minutes later, the cock was fully down Toothless's throat, distending him severely, to the point where he was more of a cock sleeve. At that point Rein pulled Toothless off his cock, pinkish slime dripping from the dragon, then slid him back down, the cock tip poking into his stomach, Rein letting out little huffs of pleasure. For the next ten minutes Toothless was brought off, then gently slid back on to Rein, the pace speeding up a little. Then in a sudden burst of pre, Rein dramatically sped up, bringing Toothless completely off, the slamming him back down, mashing the dragons face into the slime of Rein's 'crotch'.

After a few more minutes of the rough face fucking, Rin brought Toothless off, and turning him around, positioned his cock at Toothless rear end, cock leaking pre and twitching.

"Now time for the _real _fucking." Rein said, pushing his ticker than thick cock into Toothless, the dragon whimpering and groaning at the stretch.

Over a period of half an hour, Rein worked his cock fully into Toothless, hilting himself against what appeared to some sort of monstrous looking knot, the dragon's belly deforming significantly from being fully hilted. Even though Rein was much gentler than Mike, his cock was so thick that it was still a struggle to keep himself pushing back into the thrusts. But why stop himself from joining in? He thought to himself. Mike had treated the fucking like a violation, brutally pounding Toothless, whereas Rein was being more gentle, thinking about Toothless's orgasm in terms of pleasuring one another, rather than a form of torture.

As Toothless started to push back against the thrusts, Rein said, "Oh? So you finally get why I'm being gentle then?" to which Toothless smiled and squeezed himself around the invading cock, which prompted an unexpected moan out of Rein.

Over the next hour, Rein thrust into Toothless, Toothless pushing back against him, the two of them moaning and grunting, as they continued at a steady pace. Every time Toothless would squeeze, Rein would thrush extra hard, causing Toothless's belly to distend more and causing him to squeeze again, in an endless cycle of pleasure.

"Your *grh* a pretty...good ride y-you kno-w." Rein said to the dragon, tentacles caressing his cock.

"Y-you...t-t-too." Toothless replied.

"Although, I'm s-starting to lose a-a bit of my con-t-trol." Rein said shakily.

"G-go f-for it." Toothless managed to get out, now moaning uncontrollably.

Just then, Rein held on tighter to toothless, tentacles wrapping securely around his midsection, slamming the dragon down on the cock, Toothless now unable to even clench properly. For another twenty minutes, Rein thrust, getting more erratic, and also groaning to accompany them. At the same time, the knot looking monster had started to push its way into Toothless, ass stretching even wider to accommodate its sheer girth. All of a sudden, Rein slammed Toothless down particularly hard, the knot managing to slip into Toothless's abused hole, the duo cumming and howling simultaneously.

Immediately, cum sprayed thickly from Rein like a firehose, hot and purple, bulging out Toothless's belly which was increasing in size by the second. Meanwhile, Rein had coiled tentacles around Toothless's balls, and was now squeezing them, milking the Nightfury of his cum, the dragon blasting jizz into his own face, this being the most powerful orgasm he had ever had.

After about three minutes of this, Toothless belly was now twice the size of his head and purple cum was starting to flow up his throat, Rein not noticing because of the sheer bliss of his orgasm. Toothless tried to say something, but he couldn't, both because of his continuing orgasm and the fact than he was orally leaking purple slime. Just then Toothless vomited up a wave of cum, spewing it down his front and onto his cock, which was also still going, the dragon now vomiting regularly with each pulse of cum. Unbeknownst to Toothless, Rein's cum contained a similar chemical to Mike's piss, in that it greatly increased sensitivity, while only slightly decreasing mobility. Because of this, Toothless had fallen into a dazed state, now starting to drool and pant, unconsciously wanting more of Rein's cum, which was now also spurting out his nose.

Another five minutes later, Rein had managed to regain some of his scattered mind, although he was still experiencing the intense pleasure, enough to form rational thought.

"I guess...this is a *pant* punishment, so I... should probably do that." He muttered, his tentacles still rhythmically squeezing Toothless's balls, the dragon now unwittingly enjoying it.

When he finished saying it, he sent a shaking tentacle, twitching with each pulse of cum, to Toothless's mouth, which clamped over his mouth and nose, blocking the flow of purple cum, the dragon's eyes rolling back and his body twitching with each pulse.

After a final two minutes of inflation, Rein's stream tapered off, his knot already starting to deflate. At this point Toothless was so dazed, he was near unconsciousness, his belly so inflated he couldn't see over it to look at his crotch, which was bathed in his and Rein's cum. Once finished, Rein had started rolling out of the cave and into the evening beach, laying the severely bloated Nightfury on the ground, and pulling his softening cock free with a small tsunami of cum, although there was so little difference in the size of his belly, it was hard to tell any had left.

"Well, I don't know if you can hear me, but you were a great ride and I suppose I count that as adequate revenge." Rein said. "Definitely be seeing you for another round sometime!" He said, sliding away.

---

A little while later, an extra large Terrible Terror was landed on the beach, a few feet away from the punished Nightfury, where a puddle had now formed of warm purple cream.

"Ho ho ho, what do we have here!" Clarence said, grinning wickedly and laughing.

"I see someone got a bit of karma! Ohhhhh, it feels sooo good!" He added, positioning himself at the dragon's back, a foot from his ball sack, which were splayed out like the rest of him on the ground.

"I still feel I need to get a little personal satisfaction out of this though, so here we go!" He said, jumping up and landing in a curled ball, directly on the dragon's orbs, crushing them between himself and the ground, wriggling to get more comfortable, balancing all of his weight of the deformed spheres. With a grunt, Toothless creamed himself, shooting his seed on to the ground under himself.

"Huh, you really are far gone, aren't you?" He said, pushing on the dragon's inflated belly, a wave of purple cum flowing out of his ass and pooling under his balls, surrounding them, with the shifting Terrible Terror perched on top.

"Welp, I'm gonna go, you enjoy yourself there." The Terror said, grabbing something a few feet from the Nightfury and hovering back over his mashed plums. "Also here, have this as a parting gift." He said, dropping the huge smooth stone he had been carrying directly onto Toothless's already destroyed balls, flattening them, before they bounced back and took the form of slightly flattened eggs. As he did so, the Nightfury let out a soft moan and started pissing himself as well as cumming, letting all his fluids flow as the Terrible Terror felw off, laughing to himself.

-GriffonTail