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With a roar and a tremor, Hiccup awoke. It appeared that at the moment he was being pumped full of fresh piss into his already inflated belly, seemingly in the morning, of what he assumed to be the afternoon of the second day of being inside Tyne's sheath.

"H-Hey Tyne? Could you op-!" Hiccup tried to say, but before he could finish, he felt a gurgling in his throat, and then the horny dragon's urine started to dribble out of his mouth, pooling around his feet.

Hearing his request anyway, Tyne's three foot long prehensile cock started to grow back to full length inside Hiccup, and Hiccup could feel it worming its way about inside of him, which caused Hiccup to poke out of the sheath.

"Oh hello there Hiccup!" Thorn said, one of the two headed Zippleback that Hiccup was currently attached to. "How are you feeling on this fine afternoon?"

He laughed a bit, although not unkindly, stopping the flow of piss and allowing Hiccup to empty his throat.

"Alright." Hiccup said, "So, what plans have you got for the next two weeks or so?" He asked.

"Well, definitely a lot of fucking." Ivy replied, the other twin head of the Zippleback. "And we have a few ideas that will each span across a few days each."

"And you're going to be eating cum for breakfast, lunch and dinner!" Thorn remarked at Hiccup, flicking his tongue around Hiccup's cock and balls.

Hiccup gasped at the sensation, writhing on their twitching cock.

"Speaking of, in fact, it's time for your breakfast. And we know you like a challenge, so here's one. If you can keep in all the cum in, then you can choose what we do for today and the three days after that. If not, then we will choose. Deal?" Ivy said to Hiccup.

"Deal." Hiccup replied, determined to win. "May I empty myself first though?"

"Hmm, I suppose that's fair." Thorn said.

Taking a deep breath, Hiccup pushed hard on his inflated stomach, and immediately liquids spewed out of his mouth, falling onto the ground. This continued for a few minutes, until Hiccup's belly was mostly empty, save for the bulge of the massive cock crammed up his ass.

"Here we go then." Ivy said with a grin, lying on their back, limbs limp.

Concentrating a little, they wriggled their cock about in Hiccup, as it was intensely stimulating to do so, as Hiccup writhed and clenched around them, his battered prostate getting further stimulated by the thickness of their cock. Because of the constant stimulation that Hiccup provided to Tyne, they were pretty close to orgasm as it was, and the wiggling had pushed them right to the edge. Moaning a little, the two heads shivered a bit, then regaining his senses for a second, Hiccup clenched, sending them over the edge.

Feeling a familiar twitching, Hiccup braced himself for what would happen next, both Ivy and Thorn letting out twin moans and both drooling a little, which would continue throughout. Thick and fresh seed began to pump into Hiccup, and he moaned at the heat of it, although remained determined to win. He felt the beginning of the inflation, now used to it and loving it, his own cock achingly hard and dripping pre over himself.

About four minutes later, Hiccup felt the familiar rising in his throat, but instead forcefully pushed it down, as he was close to the end, and he really wanted to win. it continued for a minute, until he felt it again, now in his mouth, so close to coming out, so he clamped a hand over his mouth, and pinched his nose, trying to keep it all in, and feeling their orgasm begin to taper off, about 20 seconds left.

By the end of it, it was extremely close, Hiccup's eyes now screwed shut, and holding his breath, waiting for Ivy or Thorn to confirm that they were done.

"Aaaaand, there!" Ivy exclaimed with a pleasured sigh, looking at Hiccup.

Giving a little chuckle, Thorn said, "Okay, Hiccup, we're done now." To the inflated human.

Hiccup could only nod, and took his hands away, a flood of cum pouring from his mouth and nose, soaking his body. As he evacuated his throat and mouth, enough to speak for a moment, he took a deep breath.

"You really had to squeeze every last drop out, didn't you?" Hiccup croaked to the Zippleback, losing his concentration and spewing more cum again.

"Yep." Ivy said with a sigh watching him, "What do you want to do for the next three days then?"

Taking another moment, Hiccup took another breath, and held up three fingers.

"First of everything, clean up all of this cum, two clean the rest out from me, and three, jerk me the fuck off." Hiccup grunted, trying to hold it in.

"Okay then, seems fair." Ivy said, going up to Hiccup, and pulling him into a very deep kiss, slinking his tongue down Hiccup's throat, and starting to suck the huge amount of cum out, while Thorn got to work on the ground, slurping up all that spilled. Finishing up the ground, Thorn moved to Hiccup's dripping arousal, and enveloped it in his mouth, swirling his tongue around it, licking up all of his pre. Hiccup moaned into the kiss, relaxing as Ivy dug deep, almost making contact with the still erect cock inside of him, gathering up all of the dragon seed and slurping it into their belly.

After about a minute of suckling on Hiccup's cock, Hiccup grunted, orgasming hard into Thorn's tongue, his thinner seed splattering down Thorn's throat, and joining the pool of cum in their stomach.

Finally after about ten more minutes, Hiccup was about back to normal size, spare for the bulge of the Zippleback tentacle-like cock, and Tyne's belly was stuffed full, filled with a mixture of spunk.

"So, " Ivy said to Hiccup, "What would you like to do for the next two and a half days?"

"Hmm, well I'd like just to relax, so could we just go about as normal, but without any of the overflow?" Hiccup asked the Zippleback.

"Yeah, I think we can do that." Thorn said to Hiccup, "Just like lots of sleep?"

"Yeah, just like that." Hiccup said.

"Ok, sounds good, how about a nap right now?" Thorn asked.

"Mmm, yeah, that sound nice." Hiccup said, yawning, as Tyne's cock, with Hiccup attached, retracted back into their sheath, and the dragon and the human fell asleep, snoozing.

---

So, for the next three days, Thorn, Ivy just went about their usual day to day life, with Hiccup tucked away, the Zippleback cum that remained in Hiccup's stomach giving him a nice source of energy, as he snoozed for most of the time, talking to Ivy and Thorn for the other parts of the days, and generally getting to properly relax, not vomiting cum or piss, not being ballbusted, not being fucked senseless, just relaxing.

---

On the morning after the last day of relaxation, Ivy and Thorn woke us as usual, although gently, as not to arouse suspicion in Hiccup, and took to the air, Hiccup not waking up due to being used to the feeling now. The next plan would be a multi day one, and Hiccup would be very tired after it, so they decided to wait to tell him. After about four hours of flight, they set down, and took to walking, looking for a certain other dragon.

Rustling about in the bushes, looking for berries was another Zippleback, about the same size as Tyne, but coloured with a navy blue instead and one head with a webbed fin, the other with straight teeth, at least for a Zippleback.

"Reed! Fay! Where areeee you?" Ivy and Thorn called, looking for the other Zippleback.

"Over here!" Reed, the head with the fin called, looking up, grinning at the voice of a friend.

"There you are!" Fay said, as they, know together as Yan, ran towards the other Zippleback, in a sort of embrace.

"How have you been?" Reed asked Ivy and Thorn, twirling their heads together in a of twisting kiss.

"Great, yourselves?" They responded, and getting a similar answer back.

"So, I hear you have something new to bring to our monthly get-together." Fay says, raising an eye ridge.

"Yup." Ivy responded, his sheath opening up to reveal Hiccup, who had woken up from all the excitement.

"Hiccup, this is a friend, or I guess you could say they are our 'partner', because the human phrase 'boyfriend' doesn't really suit this. We meet up every month for about three days, and these two are much more kinky than us." Thorn explained to Hiccup, nuzzling up against Reed.

"Ok, I think I get it." Hiccup responded, "So, what is going to be happening then?" He asked.

"Well, we've wanted to try something like this for a while, so we will. Its sheath play." Fay explained.

"Oooooh, I like the sound of that, especially that Hiccup is here." Ivy said, getting excited inside Hiccup.

"Yeah, basically Hiccup will be like a double ended sleeve for us, a channel if you will." Reed explained, getting excited, their almost identical cock starting to come out, slithering in the air with pre dabbling the tip.

"But first, we need some of that sweet Zippleback ass." Fay said with a smirk, going round to behind Tyne, and taking their hips, cock positioned.

"And vice versa." Ivy replied, and the two of them groaned simultaneously as the other Zippleback pushed in, spearing into them and immediately thrusting with their full length, no foreplay needed.

On Tyne's cock, Hiccup gurgled, feeling the flow of pre start and he jerked forwards at the big thrust in, feeling Tyne get quickly aroused and fully erect inside him. The outline of the cock was already visible, and he lay back, relaxing for what was about to happen behind him. Really thrusting hard, Yan pushed Tyne into the ground and getting a good angle, while Hiccup was pushed onto the grass and ground, Tyne using this as leverage to thrust into the human.

The two dragons and the human went at it for the best part of forty minutes, Yan slamming into Tyne, while they rammed into Hiccup, everyone getting very close to their collective peaks. Through a haze of lust and grass, Hiccup could feel the thrusts and pushes get more erratic, and he felt the familiar wriggling that happened just before orgasm, but because he was being slammed into the ground, face buried in the pre covered ground, he couldn't do anything. Roaring, Yan crammed themselves into Tyne, and Tyne moaned loudly, unloading into Hiccup, who grunted, their orgasm hitting harder this time.

All three bodies moaned in sync, all unloading vastly different amounts of cum, Hiccup's few small spurts instantly dwarfed by the two Zipplebacks, and their monstrous loads. Ivy and Thorn both pant and moan, hot and thick dragonseed spilling into their ass, as they spill into Hiccup, who writhed on the ground, as the cum was almost immediately shooting out of his mouth from being pressed on the ground.

After about three minutes they all groaned and tapered off, Hiccup groaning the most, the grass in front of him covered in thick spunk.

"So, how was that then?" Reed asked Ivy, Thorn, and Hiccup.

"Amazing, as expected." Thorn replied, and Ivy nodded.

Spluttering to clear his throat, Hiccup looked up. "G-Great." He said, giving a wobbly smile.

"But now, time for the main event." Fay said, as they swiftly pulled out, Ivy and Thorn moaning in unison at that.

As Hiccup had been pushed onto the ground and most of the seed had splattered out of his mouth, only a little remained in him, so he wasn't really that filled. Coming round to Tyne's front, their ass leaking a bit, Yan's cock waved in he air, covered in cum, in front of Hiccup. Slowly it started to go down, and slid mostly back into their sheath, but not fully.

"Now, open up." Reed said to Hiccup, grinning.

"Y-You want me to t-take all of you?" Hiccup asked, a little nervous.

"Yup. Right down to the base. See you in three days!" Reed said, Fay also grinning.

"Hmm, o-okay t-then." Hiccup said, opening his mouth wide, wondering what would be happening for three days.

Both Yan and Tyne waddled towards each other a bit, and Yan inserted the tip of their cock into Hiccup's mouth and he gagged a bit as it slid down his throat, bulging it out some. Grunting at the amazing feeling of Hiccup's throat, Yan pushed forwards more, and Tyne also pushed, trying to get sheath to sheath with Yan. Almost there, Hiccup moaned around the thickness filling his mouth, and his throat loosened a bit, face bumping against Yan's sheath.

All four heads grinning, Tyne pushed more, pushing Hiccup inside Yan's sheath, and jamming more of their tentacock inside Hiccup. They then gave a little thrust, almost hilting Hiccup, and both Ivy and Thorn felt the interesting sensation of Yan's cock touching theirs, inside Hiccup, and they gave one more thrust, pushing Hiccup's face right up against their base, his jaw stretched comfortably around it. Inside Yan's sheath it was very musky, as it had been a while since they washed in there, and Hiccup got a little drunk on it, eyes drooping as their cock grew inside Hiccup from all the stimulation.

Now that both Tyne and Yan were sheath to sheath, they both wiggled about, cocks touching inside Hiccup, and growing a little past each other as they both got fully hard. All four grinned, and went in for kisses, on the start of a very long 72 hours for Hiccup, who was also getting hard, and he relaxed, letting the Zipplebacks take the reins.

---

While Hiccup had been whisked off with Tyne, back at the quarry after they left, the four Monstrous Nightmares: Kai, Shen, Ardoa and Reth, were left squirming on the ground and gasping in pain. Ardoa had been punched and then kicked brutally in her sensitive dragon snatch by Toothless, then shocked by an electric eel, zapping her clit painfully. Shen's balls had been crushed under Toothless's footpads for a full ten seconds, while Toothless ground and jumped on them, and then the black dragon had hopped off and brought another fist down upon them. Kai had been lifted up in the air by his balls, which he had managed to prevent a bit, but then he just got smacked again by the tree branch, and finally Reth, after getting busted the day before, had a rock land on his crotch, also busting his nuts again.

Toothless had also, mistakenly, tried to prank Hather, but even though he had succeeded, he immediately got karma for it, by Hather refilling the smaller dragon with all the liquids that Toothless had tried to pump into them, and he had also been plugged from both ends, one with a dildo and the other with a Gronckle's mating plug. After Hiccup had left Hather had left the balloon of a Nightfury on the ground, while they attended to themselves, both heads moaning simultaneously as they came, thick musky seed pumping all over Toothless, just to add insult to injury, but they were far from being done with him.

While Toothless got soaked, the Nightmares still panted and groaned, Shen probably in the most pain, whining in a ball, clutching his sack in his claws, pissing himself. Kai had recovered the most, although his ass had been smacked by the tree branch and it was stinging a little. Even though Ardoa was still writhing in pleasure/pain, she giggled a bit, because she just loved watching ballbusted male dragons squirm in pain.

After about five minutes from the original bust, Kai flipped himself onto his front, clutching his nuts with one claw, and crawling forwards with the other, coming to Toothless with Hather.

"F-Feel l-lucky you have internal b-balls." Kai grunted to Hather, to which they replied, "Well Toothless here did also manage to prank us, but you can see that it was a mistake."

Next to come over was Ardoa, waddling with wide legs around her swollen pussy, winching with each step, and when she got to Kai, she just slumped face forwards, groaning.

"You?" She asked, not even bothering to turn to Kai.

"Hung by the balls, then whipped by a tree branch. Yourself?"

"Cuntbusted by kicking and chopping, then zapped by an electric eel." Ardoa responded, groaning again.

"Ohh, now I don't feel so bad." Kai responded, winching at her reply.

About three minutes after that, Reth stopped groaning and moaning, as he had creamed from the force of the rock smashing onto his balls, and some would say he went through the least pain, but the still limped over, resting besides Ardoa.

Another three minutes after that, Shen, who was still panting and gasping, dragged himself over with one claw, on his back, as on his front would hurt too much.

"You look like death." Kai said to him as he came over.

Taking a moment to cry softly out, Shen took a deep breath. "T-Toothless jumped on m-me from 15 f-feet in the air, and then f-for ten seconds s-straight, he ground all 800 kilos of himself onto me, then h-he jumped off, and delivered a mind s-shattering chop." Shen said, huffing and holding his swollen sack in both claws, the pain still excruciating. All the others winched at hearing this, even Hather, who were usually not able to relate.

"So, what're we going to do with him then?" Kai asked the assembled dragons.

"I say we throw him to the Speedstingers, let them have him for a week, stuffing him full of eggs until he's twice the size he is now, and then letting them use his balls for biting practice." Reth said, grinning at the idea.

"I second that, although with a Skrill there to accompany him, to fry those eggs of his." Ardoa said, as she wanted revenge for the zapping.

"Hmm, I-I think w-we should o-open him up as a p-p-public ball stomping s-station, so s-stressed dragons c-can let t-their anger o-out." Shen gasped, trying to breath smoothly.

"How about we combine all those ideas into one, for the next two weeks." Kai proposed, thinking of all the ways they could torture the dragon, making their previous night of ballbusting him look like a gentle licking. Kai was probably the most cunning and clever of the group, so if this idea was going to come from anyone, it would be him.

"We like the sound of that." Hather injected, giving twin smiles as they looked upon the plugged Nightfury. "Although, for the next five days, we think it would be most deserving to go for Reth's Speedstinger idea." They added.

"Mmm, that sounds good, at least until we recover and get everything else set up." Ardoa said, flipping over to massage her folds carefully.

"Well, Kai, since you're the most mobile, could you help us fly Toothless to the Speedstinger pits, its about three hundred meters from here." Hather asked the Nightmare.

"Yeah, sure, I'd gladly help." Kai responded, getting up and stretching his wings.

Working together, Kai and Hather lifted Toothless up and into the air, not being gentle, and they carried him to the Speedstingers general home on the island, and they set him down, a few of the wingless drakes gathered there.

"What's this you're bringing to here?" One of them, a male, likely the Alpha of the group, asked, his stinger raised.

"This is a plaything for you and your families to toy with, to use as you wish, and above all, make sure to give him one hell of a time down below." Kai said to the leader, who lowered his stinger.

"Isn't this Toothless?" He asked, having a closer look at the ballooned dragon.

"Yup, and he wanted this, as a little break." Kai responded, mostly telling the truth.

"So we can use him as we like, and our young ones can use his underneath for biting training?" He asked, getting interested.

"Yes, exactly that, you can have him for five days, and then we'll be back for him." Kai said, unclipping the gag from Toothless's mouth, pulling it out, and adding a solvent to the mating plug, so it dissolved, cum beginning to pour from both ends of Toothless, and he let out a soft sigh, starting to expel the fluids. Jumping into the air with a light wince, Hather already gone, Kai waved bye.

"Well see ya then." The leader shouted up, still a bit confused at the randomness of it all. "Well, I guess we have a new toy then." He muttered, leaving Toothless for now.

---

About three hours later, Toothless finally awoke from his deep, lust-induced sleep with a groan, moaning slightly as he felt fluids dribbling from both end of him, most of the pain in his balls now gone, faded to a dull ache. He looked around in confusion, the last thing he remembered being Hather holding to his ass and filling him as a lesson, and now he found himself here, in a sort of massive pit, more of a slope to a stone walled part of land. planting his feet on the ground, he tried to stand on trembling legs, although there was still so much cum in him that it was difficult.

Just as he was getting up, the packs of Speedstingers came back from a hunt, seeing Toothless finally up. The leader went up to the Nightfury, and without even saying anything, he went round to Toothless's side, and pricked him with his tail, giving him a good dose of paralyzing.

Being quite a big dragon, Toothless could handle a sting from a Speedstinger, albeit making him slow, but he could still function, and the Alpha and the others knew it. So, after the first sting, a bunch more of the wingless dragons went over, and methodically stung Toothless, so that he would be stuck for a good while. The paralyzing sting made sure the recipient wouldn't be able to control their muscles, but depending on if the stinger used a different part of the tail, they could make it so the place stung would either be limp with relaxed muscles, or rigid with frozen muscles, and with both of those ways, the victim could feel everything.

By the end of the stinging, Toothless's mouth was hanging open, relaxed and dripping fluids, but he was still very much conscious, and his wings were also relaxed on his back. His legs and tail were frozen, stuck standing up, tail up in the air, and over his back, exposing his behind perfectly, for full access. With the rest of Toothless stuck, unable to move, he groaned a little bit, cum dripping from his maw.

Going round to his unstung rear, the leader of the stingers grinned a bit, and jabbed his tail directly at Toothless's nuts, making the black dragon whine in slight pain, which caused them to relax, sagging, but also churning with seed, and he also stung the dragon's cock, making sure to keep it rock hard, and finally his ass, relaxed so it continued its dribbling.

"Now, because you were presumably asleep, you are our toy, so good luck is all I can say!" The leader told Toothless in a bright tone, Toothless trying to respond, but it just came out as a groan.

Going round to the dragon's rear again the Speedstinger started the day off with a good kick, planting his clawed foot in Toothless's sack, his balls giving a nice bounce, and the dragon moaned in pain, unable to do anything at all, no matter how much he wanted to.

"By the end of these five days, your gonna be begging for me to do that, compared to what's coming." The leader tells Toothless, as young Speedstingers can be brutal, and he gives three more powerful kicks, then he turns to deliver a much stronger one, his clawed paw rocketing out and crushing into Toothless's helpless nuts, squishing them into his pelvis a bit, pre dribbling from his frozen cock, from the start of the busting.

Toothless whimpered in pain and confusion, still confused at to why, but with a click he remembered how he had busted the Nightmares, and Hather, so this would not be good for him.

"Also, you're our fuck toy!" The leader said, his twelve inch cock appearing, hard and only a little thick.

Jumping onto Toothless back, and using his sack for leverage, the Speedstinger plunged in happily, squeezing the bigger dragon's balls with his claws as he groaned and yipped in pleasure, enjoying this a lot. All Toothless could do as whimper, trying to prepare himself for the next days.

---

Later, as it was starting to get dark, the last of the Speedstingers for that day jumped off Toothless's cum soaked behind, his rear leaking constantly now, and his balls swollen from every Speedstinger busting them while fucking him, and also giving fun kicks to get a groan of pain out of the tortured dragon. As Toothless's eyes started to close from both exhaustion and pain, the leader came back up to him, keeping his eyes open.

"Oh no no no, no sleep for you!" He teased, and two juvenile stingers came over with a chirp from the Alpha.

"If the paralysation wears off at any time during the night, and you try to get away, then these two will bite down on your balls." The leader told Toothless with a serious tone, and each juvenile took one of Toothless's large orbs in their mouths, poking and jabbing with their tongues and teeth.

Toothless only groaned in response, but even if he could move, he wouldn't be able to from the pain he was in. Before leaving for the night, the leader went under Toothless to his cock, where a mini river of pre was coming from, and he gave a hard punch to Toothless's cock, leaving with a laugh.

---

When the morning sun finally shone upon Toothless's face, he gave a shuddering groan, drenched in sweat and in a lot of pain, but also quite a lot of pleasure. All throughout the night the juveniles had nibbled, jabbed, poked, prodded, and put pressure on his nuts, even while sleeping, so it was constant, and he had gotten not a wink of sleep. He had cum three times, and there was a small lake of spunk under him, his belly covered and he was now slumped in it, as the paralyzing had worn off and he had just dropped to the ground, unable to move anyway.

The leader coming up to Toothless again with a smile on is toothed face, he signalled for the juveniles to finally release the black dragon, and he gave a soft gasp as they did, as he was so unbelievably sensitive. Toothless was also unable to speak, beyond exhaustion.

"I assume you didn't sleep?" The leader asked Toothless, not expecting an answer.

Going round to his back, the smaller dragon peered at Toothless's largely swollen orbs, clearly causing him significant pain. Deciding to put him out of his misery for now, the Speedstinger reared back for a truly powerful strike, giving a flying kick to Toothless's nuts, smashing them brutally up against his pelvis, and they briefly deformed, into more of an egg shape. Toothless didn't even have the strength to cry out, all he gave was a sigh, and he fainted, eyes rolling back.

The leader wasn't cruel, this as just the best way to get Toothless to sleep, and it was also fun. Getting a bunch of other to help him, they dragged the busted Nightfury to a nearby cave in the side of a wall, laying him in the shade and darkness and letting him sleep, all unstung now, and even though he was far deep asleep, Toothless reached his front paws backwards to hold his assaulted sack, then he went still, not even groaning for how deep asleep he was.

---

About fifteen hours later, Toothless rolled around a bit, starting to come to, and he almost yelled at how much pain was radiating from his balls.

"Oh, you're awake now." The leader said, coming in just then, and approaching Toothless in a non-malicious way. "How are you feeling?"

"T-Terrible..." Toothless replied after several moments, trying to at least control his voice.

"Well, that's not surprising, you lasted much better than I thought, and I'm not cruel, so I decided that I should give you some sleep." He explained, peering at the dragon's swollen nuts again, leaving them this time.

"Now, my name is Rathos, and I'm not going to do any more busting today, but more will happen." He said, and Toothless gave a shaky sigh of relief.

"If you behave and help us out, then we'll go easy on you, and by the looks of it, you need that." Rathos said to Toothless, who simply nodded in response, agreeing with his terms. "For now though, feel free to sleep, and I'll get to things in the morning. Sound alright?"

"Y-Yes...Thanks." Toothless responded gratefully to Rathos, shifting position a bit, so he was lying on his back, to gently cup himself.

---

The next day, wen Toothless had somewhat recovered, enough to waddle around, Rathos came back and explained what would be happening. Just as long as Toothless didn't try to get away or refuse anything or anyone, then the Speedstingers wouldn't sting him, or bust his balls quite as brutally as before. So, for the that day and the two consecutive days, Toothless attended to the Speedstingers needs where that would be a good fuck, a cum dump, or a hole to take.

It was honestly a bit of a holiday for Toothless, and Rathos knew that, almost knowing what Kai and Hather had been talking about when they had left Toothless with them for five days to go off and do something, which obviously needed time for preparation and planning. At multiple times, Toothless had to suck off at least ten Speedstingers simultaneously, so by the fifth day he was smelling only of cum, and covered in dried cum as well, having not had a bath.

Through the days the ballbusting was light, only a few kicks here and there, which gave Toothless proper time to recover from all the previous sessions that the Nightmares and Hather had inflicted upon him.

"So, how you feeling today?" Rathos asked the Nightfury, on the evening on the fifth day, both in the cave.

"Not bad actually, almost good." Toothless replied to Rathos, with a smile.

"Well, " Rathos said, darting round to Toothless backside for a moment and delivering a quick kick to each nut separately. "How about now?" He said with a grin, coming back round to Toothless's front.

"Less good." Toothless replied in a pained groan, slumping forwards to cup his balls, breathing shakily bust still smiling.

"Go further into the cave, there's a natural spring there, have a bath, because you really stink." Rathos said to Toothless with a grin, leaving the cave for now.

"Thanks." Toothless muttered, waddling towards it, and relaxing in the hot water, cleaning himself off, and then going to sleep for the night.

---

By the morning, when Toothless awoke, Kai and Hather were back to get Toothless, and with a few more painful kicks from Rathos, the dragon waddled out of the cave and to the other dragons, who nodded in approval at Toothless's recently kicked balls.

"Well thanks then Rathos." Toothless said, spreading his wings.

"Yeah no problem, come back any time." Rathos shouted back with a grin, and the three dragons took flight, going back to the main quarry.

As they landed, Toothless first and then Hather and Kai, Toothless looked around, seeing Shen, Ardoa, and Reth, all waiting for him, and Kai and Hather herded him towards the others. Going behind him, Shen looked approvingly at Toothless's behind, waddling a bit, and still sore. With absolutely no warning whatsoever, Shen's back leg shot out and nailed Toothless directly in the plumbs, and the dragon fell to the ground, groaning in pain. "Ooo, that felt good." Shen muttered, grinning.

"I-I suppose t-that was k-kinda deserved." Toothless whined out, holding his sack protectively, lying on his back.

"Yes, yes it was." Shen replied, coming round again with a large leaf of some sort of purple fluid. "Drink." Shen commanded, eyeing Toothless's crotch again.

Wanting to avoid any unneeded pain, Toothless slurped it down, not feeling much different, the liquid only slightly bitter. The liquid was a concentrated lavender solution, effectively a sleeping liquid, but very concentrated, so about a minute later, Toothless started to feel weird, eyes drooping out of his control.

"Wha-? What washhhh that-t...?" Toothless tried to say, slurring his words, and then his head promptly fell forwards, the dragon now deep asleep, limp on the ground.

"Right, time to get to work then." Ardoa said with a sigh, everyone getting ready.

Dragging him over to a cave, the dragons put him to the side while they organized all that they had made. They had created a rig of sorts, to hold Toothless, and one that blended in perfectly with the cave. Picking the drugged dragon up, they set him in the frame, attaching wing binders so that they wouldn't get in the way. After about twenty minutes, they stepped back to observer the amazing sight.

Toothless's ass and back legs were sticking out of a fitted slot in the wall, tail raised and tucked in to the wall as well so his ass and hole were exposed, as well as his sack containing his busted nuts. Round the other side, Toothless's head was poking out, maw gagged with a ring gag, saliva dribbling. Below that was his cock, also accessible, fully erect and throbbing with quite a large chamber beneath, for the collection of fluids. He had a leg spreader on, and mits on his front paws, which were locked inside the middle with his body.

"So, who'll be the first to try out Gloryhole Toothless?" Reth asked the assembled dragons with a smirk, now recovered.

"Well I think it would be fair if I were to have the first turn, all things considered." Shen said, coming forwards, cock already erect, balls still sore but also swollen, not from pain, but from being so pent up, as he had been saving himself for this. Just about then, Toothless awoke with a start, groaning and huffing.

"Oh Toothless, perfect timing, you're now going to be a gloryhole!" Ardoa said with a laugh, "You're taking Shen first..." She added, and Toothless gulped, as he knew what that meant, his entire body restrained, unable to move, again.

Going round to Toothless's ass, Shen gave him a firm squeeze, mounting the bars above the Nightfury's behind, positioning his gigantic cock at his entrance, all twenty inches of it ready to plunge in. Taking his sweet time, Shen took one of Toothless's balls in each clawed paw, and squeezing both hard, he began to push in, none to gently, and then he slammed fully in, crushing Toothless's balls with a grunt of satisfaction, feeling them deform in his grasp. At the first squeezes Toothless gasped in pain, trying but failing to get out of the way, and then he cried out in a much stronger pain as his busted balls were further pulverized by Shen's vengeful grip, the Nightfury writhing and whimpering.

Loosening his grasp a little but not much, Shen started on full length thrusts, impaling Toothless's prostate on each one, making the other dragon's cock dribble and drip pre, a little painfully as well from the busting, and Shen rhythmically pushed a bit harder with every thrust. Moving on to faster thrusts, Shen let go of Toothless's busted balls, and instead let his bony pelvis do the work, as every time he slammed in, his pelvis would crush right up against Toothless's sack, hitting it hard each time.

After about forty five minutes of this from Shen's built-up stamina, the thrusts start to get erratic, Toothless whimpering as he felt Shen getting close, having already cum, the lower compartment soaked in white. Shen then grinned and roared triumphantly, taking up Toothless's nuts again and crushing them much harder than before, and keeping the grip there, balls deep and flared as he began to pump his load into Toothless, still obliterating his plumbs. Toothless yelled out and tried to escape the grip but to no avail, cumming forcefully again as the dragon-batter was literally forced from him, and he continued to cry out in nut-agony.

For a full eight minutes this went on, Shen pumping Toothless full while busting him, Toothless yowling and yelping the entire time, not managing to escape the brutal grip of Shen. At the end of it Toothless was a whimpering, drooling mess, and Shen releases his balls from the death-like-grip, yanking his still flared cock from Toothless, ass winking and cum leaking down the backs of his legs, which were limp. Extreme nut-ache pulsed from Toothless's back, unrelenting and unrelievable because of his position. As a final message and note of completed revenge, Shen turned swiftly and delivered an absolutely devastatingly brutal kick to Toothless already destroyed orbs, completely flattening and stabbing into them, and he removed his foot, Toothless just wailing in sheer blinding pain, unable to do anything else as his body spasms.

Laid back, the others watch in satisfaction, and Shen joins them to watch the tortured Nightfury try and deal with his karma, and Ardoa swiftly gets up, ramming her pussy into Toothless's face, to quieten him down.

"Lick, or I kick..." She threatens playfully although seriously, grinding into him.

Still unable to even think through the pain, Toothless automatically gets to licking and slurping at Ardoa's soaking pussy, drinking down her juices and huffing in her scent, in between wails and whines. She grins and grinds more onto his face, already close, and with a sigh she floods his mouth with cum, thin but sticky, and pulls away so she can soak his face, making him horny from the smell, but that quickly stops from the ache in his dragonhood.

As Ardoa went to sit back down, Kai came forwards next, starting with a kick, then going to a slow pace with hotdogging thrusts, Toothless already unconscious from the kick, everything simply just too much for him to handle.

---

In the morning of the next day, a long flight away, Hiccup groaned as he started to wake, remembering what was going on and why he was skewered by cock, stuffing both his mouth and ass. Tyne and Yan had kissed for most of the day, and cuddled for all of the night, making Hiccup shift about on their prides, face jammed into the base of Yan's cock, in their sheath.

At long last as the two dragons awoke, groaning as they did and twitching inside Hiccup, who was also groaning.

"Well, I know you can hear us, so time to actually have some fun." Ivy said to Hiccup, wriggling more as both dragons got erect, making Hiccup moan as he was completely filled, the tips of their cocks touching and sliding past each other inside him.

With dual groans, both dragons stared to piss, Hiccup flailing a bit as he felt the hot rushing sensation, but completely unable to do anything about it. Hs belly immediately started to swell, already bulging because of the thickness inside him, and he felt the torrents of urine filling every gap that remained inside of him, squirting out his mouth and filling the space that his top half occupied. Yan began to thrust gently into Hiccup, as did Tyne, making Hiccup start to get aroused, his package crammed against the inside of the sheath.

With the bladders of the dragons sufficiently emptied, and a small lake starting to form, they turned up the power of the thrusts to much harder, slamming into both Hiccup's ass and maw. The ground was even shaking slightly as they railed poor Hiccup, his face getting pushed right into the red flesh of inside Yan's sheath, and his legs spread extra wide to try and take Tyne's 'knot'.

The four heads panted and kissed, and they all wailed out as they slammed headfirst into the orgasm, grunting and groaning as they barged past it, still thrusting ferociously as cum jettisoned into Hiccup, his body feeling utterly divine to them, and inflating more, everything just so musky and coated in white.

One full intense hour later, the Zipplebacks finally stopped, falling to the ground and coated in sweat. Everything in a ten meter radius was white, including both dragons, and Hiccup couldn't even be seen through the amount of it. He had fainted at the ten minute mark, just like Toothless as everything had just been too much, the smell seemingly ingrained in his skin now.

"We love you." Thorn manages to grunt, giving an affectionate lick to Fay's nose.

"Mmm, us too." He responds, sighing as he dozed off, to sleep for a long time.

---

Two days later, in the morning, Tyne awoke, both heads smiling and sighing, trying to rouse Yan.

"Hmm, wha?..." Reed muttered, trying to wake Fay up.

"Y-Yeah, I'm awake..." He mumbled, blinking and shaking his head a bit, the four now awake.

"Well, I think its safe to say that that was the best meetup we've had in a very long time, wouldn't you say?" Ivy says.

"Yes, think that would be quite fair to say." Reed replied with a smirk. "How do you think he's doing?"

"Well considering we're cum in him upwards of ten times, I'd say he's pretty spent. Time to pull out?" Ivy says, wriggling about a bit.

"Yeah, we'll go first." Thorn says, and takes a hold of Hiccup's midsection, and started pulling, Hiccup's ass stretching once more, and the entire length of their cock sliding out of him, now hanging by the cock in his mouth. Yan then took Hiccup's body in their claw, and swiftly pulled him off, leaving him on the ground, utterly soaked and leaking. Waddling off, Tyne and Yan went to the river to get clean, washing themselves off and clearing everything out, as Hiccup had been on Tyne's tentacock for nine days straight, so at last they could get it clean.

Taking Hiccup up once they were clean, Tyne washed him in the river too, making sure he was mostly empty and washed down, although of course still smelling of cum. The dragon laid him down, in a clean-ish spot, the two Zipplebacks cuddling softly while they waited for him to wake.

About four hours later, Hiccup woke up, surprisingly finding himself clean, and he sat up, working his sore jaw.

"Hi there, all rested now?" Reed asked Hiccup, looking over to him.

"Mmm, yeah, but I feel I could still sleep for a long time." He replied, groaning as he stretched.

"Well, we're heading off now, see you next month!" Fay said, Giving both Ivy and Thorn a kiss, and Hiccup a lick.

"Well thanks guys, that was an amazing time, and I'll definitely see you again!" Hiccup called out, as Yan took flight.

"See ya love!" Both Thorn and Ivy chorused, sighing as they watched them fly away.

"So, what now?" Hiccup asked, still on the ground, relaxing in the open air for once.

"Well you said you could sleep for a while, so get in." Ivy said as they turned around, exposing their ass to Hiccup, who stretched again and got up.

"Alright, sounds fair to me." He said, going to the white streaked part of the forest and coating himself, then going back over to the Zippleback.

Starting with his hands, Hiccup pushed them a little inside, up to his elbows and spread them apart, both Ivy and Thorn moaning as they were stretched. Going down to the ground, Hiccup started with his feet, pushing them smoothly in, and then to his torso, feeling the dragon clench around him, and he then slid the rest of the way in, so he was completely sealed in, only the tube going to his nose sticking out, attached to Tyne's back. Settling down comfortably, he yawned, huffing in their thick musk and wriggling around a bit more, the warmth making him feel sleepy, and Ivy and Thorn sighing in pleasure as Hiccup used their prostate as a pillow.

---

Back at the quarry, Toothless was in a similar situation, but not nearly as relaxing as Hiccup.

For four days he had been railed in every way by the Nightmares and Hather, fucked in every scenario and position, and he had been busted until he was blue in the face. His behind was utterly soaked in countless loads of both cum and piss, legs limp and coated in cum, as well as the surrounding area. At his head was also a similar situation, and the chamber below was filling up, Toothless's belly sloshing inside the contained part of his body. There had been a lot of pain, but in some ways a lot more pleasure, and Toothless had lost track of how many orgasms he had gone through quite a while ago.

"Aaaa, and I'd say that would complete our part of this whole thing." Shen said with a happy contented grin, pulling out of a groaning Toothless once again, Toothless's ass dribbling cum again.

"Although you may have gotten used to this with us, its about to get a whole lot more interesting for you." Shen explained to Toothless, bringing his right foot back and with all his force, slamming it into Toothless abused balls, crushing them again. Toothless whimpered in pain, almost used to it now, but then Shen took Toothless's right nut up in his clawed hand, holding it between two of his claws. Giving Toothless of a taste of what was to come, Shen began to press his claws together, making Toothless flail, as this was a new feeling, Shen's sharp claws piercing into him and pulverizing his already tenderized ball. Shen sighed and let go, allowing the ball to reshape and swell a little, and he went around to Toothless's mouth and head, removing the gag, when Toothless's wailed, seemingly gratefully.

"A-A-Aah!" Toothless gurgled, trying to clear his throat. "W-What's h-h-happening next?" He added on the end of the gasp, trying to breathe regularly.

"Well, how have you enjoyed being a gloryhole for us lot?" Shen asked with a smirk, looking into the Nightfury's dazed eyes.

"I-It was k-kinda n-nice..." Toothless said quietly, blushing.

"Well that's exactly what's going to happen next!" Shen replied with a bright look in his eyes. "You are now the service station for any horny dragon needing a good time, at least for the next four days!"

"S-So what t-types of dragons?" Toothless asked Shen, trying to lick some of the cum off of his muzzle.

"Any that may come by, and that means that they will also take out their horny frustration on your balls, and unlike us, they won't show any mercy, so you better be ready." She said to Toothless, booping him on the nose with a claw.

Toothless groaned in response, trying to mentally prepare himself.

"Although, I will leave the gag off, as I feel you need it." Shen said, putting it to the side.

"Thanks, I guess." Toothless muttered in response and Shen grinned again, walking away.

Having already prepared the 'invitation' for the dragons to use Toothless, all the Nightmares and Hather had to do was wait. They had spread a solution of concentrated dragon scent, getting stronger as it got closer to Toothless, all over the island, so that any dragons in need of a good fuck would know where to go.

Within half an hour, over the crest of a hill came the Speedstingers, with Rathos at the front, grinning as he knew exactly what was going on.

"Hey there Tooth, how ya doin?" He said casually to the Nightfury, coming round to his face and rubbing his cock on the dragon's nose.

"Hmm, alright, I guess I'm now doing this." Toothless replied, giving Rathos's cock a lick, as he didn't mind the smaller dragon's company at all.

"Heh, well it looks like you've been having quite the time here." Rathos commented, sliding his length smoothly into Toothless's awaiting maw, and the dragon started his job by doing a little sucking, now used to it.

Rathos groaned in familiar pleasure, straddling Toothless face and thrusting smoothly, while another Stinger went to his behind and started a similar process, although thankfully not actually stinging this time. Along with the one in his ass, the two juveniles from before came along and each took hold of a nut, Toothless groaning as he felt the familiar sensation, and Rathos grinned at his reaction.

For two hours the Speedstingers went at it, dumping multiple loads in and on Toothless, and it wasn't the worst experience for the dragon, it was actually quite relaxing, apart from of course the nibbling and squeezing by the juveniles, but even that was relaxing compared to the punishments dealt out by Shen and the others.

They left soon after being satisfied, Rathos giving one last 'friendly' kick to the nuts, before leaving. Not even five minutes later, a Deadly Nadder landed, after recognizing the scent, and went inside, barely even surprised to see the cum-covered ass, ready for a pounding, and the busted looking nuts, looking like they needed a good beating.

Toothless of course couldn't see the Nadder, so he murred in interest when he felt the rig shake a little as the Nadder mounted the bars, a wickedly barbed cock growing from his crotch, lengthening up to a good looking 18 inches, the barbs designed to stimulate the receiver quite a lot. Shifting a little, the male positioned his tail so it was wrapped around Toothless balls, the spines digging in a bit, and Toothless's eyes went wide as he realized what dragon was about to claim him.

"N-No wai-GRNNNN!" Toothless tried to say, but before he could finish the Nadder started to slide in, the barbs tugging at Toothless's hole, and he tightened his tail grip as he went, stopping Toothless from speaking further as he felt the spines poking into him.

With a complete disregard for how Toothless felt, the Nadder quickly ramped up to thrusting strongly, ploughing Toothless, and the barbs making him pant and groan the whole time, each thrust earning a squeeze of the tail, and the Nadder got into a good rhythm, grunting and chirping in his own world of pleasure. The thrusts started to get stronger, stimulating Toothless more and making him cum again, sighing in pleasure, then groaning as the grip got tighter still. Within a few minutes, the Nadder reached his peak, and with a loud domination screech, he buried himself balls deep and came, barbs extending inside a little, seed splattering inside Toothless and the grip on his sack got deathly tight, making Toothless's eyes bug out. The dragon tried to voice his pain, but only drooled and gaped his mouth, unable to pass out because of his newfound tolerance.

At the end of five minutes, the Nadder's orgasm stopped, the barbs retracted again, and he released his tail Toothless slumping and crying out softly. Pulling out gently, the Nadder gave a few affectionate licks to Toothless stuffed ass, cleaning him up a bit, and wondering off, then swooping back into the air once he had cleaned himself.

---

Another four days later, the last four, Ardoa woke up comfortably in the morning, yawning happily and opening her eyes, seeing a far-off dragon in the distance, and she smiled as she saw it, waking the others, as the dragon was about twenty minutes inbound.

"Hey, wake up, I think I see a familiar pattern of colours." She says to Reth, who groans and flips over, which wakes Kai and Shen with a start, Shen sleeping on top of Kai.

"Hey Hather buddy, you too." Kai groans, poking the bigger dragon in the side, who groans, eyes blinking to try and wake up.

"Ah, I see that our friends are finally back." Hather says in their dual voice, sitting up and peering into the distance.

---

About twenty minutes later, Tyne landed at last, the bulge in their sheath back and covered in a little cum.

"Hey, how ya all doing?" Ivy asked, folding their wings in.

"Great! I assume that you've been enjoying your sleeve?" Ardoa responds, gesturing to the spot of cum on their crotch.

"Heh, yeah, he's been amazing." Thorn replied, looking towards the cave behind the dragons.

"Ah yes, that. I hope you have a good amount of energy, because Toothless needs one more good fucking, and I know you love to bust some balls." She says, beginning to lead him there.

"Mmm, good, been saving up for this." They both reply, smirking.

Getting into the cave, both Ivy and Thorn smile wide, looking the the ass in the wall. Toothless ass is dripping from a fresh fuck, and his balls are steaming slightly, as a Seashocker had just finished, and using electricity, they had woken the dragon up, depositing a good load inside of him. Toothless had been fucked by many types of dragons, thick cocks to thin cocks, barbs to spines to knots, gentle caring thrusts, to ground-shaking slamming in. His balls had also been abused for the entire time, some dragons only gong for a light and soft poke, others giving no mercy at all and giving constant, nut-scrambling kicks, making Toothless's balls so sensitive, that even the exhale of breath on them would make him whine. He had been filled with way to many loads, thin to thick, gloopy to musky, and the chamber below was almost overflowing, the dragon himself drained each day.

Trotting over, Tyne grabbed Toothless's ass in a claw, rubbing the cum further onto him, humming as they did so.

"Alright, now go as hard as you want, really give it to them, think of it as the finishing blow." Ardoa told Ivy and Thorn, taking a lie down with the others to watch.

"Go as hard as we want hmm? Well Toothless, we're gonna make the past fourteen days seem like a relaxing massage... Its going to hurt even to stand up, and as for you Hiccup, well don't think you're getting out of it either, those untouched balls are getting turned into butter. " They said to the dragon, also including Hiccup as well, as he was awake and hearing.

Both the human and dragon gulped, and as Tyne started to get aroused, and Hiccup appeared, stomach wriggling. He didn't speak, as he was interested of how this would go, and he grinned when he saw the state of Toothless, and thought how nice it must be for him to have no control whatsoever.

Putting Hiccup's head to Toothless dribbling ass, Hiccup's hair so drenched in so many loads already that it didn't matter, Tyne began to push in, Toothless groaning as this stretch was quite a lot wider, Hiccup being pushed in smoothly up to his waist, then with a rough pushing thrust, he was pushed into Toothless until Tyne was at their base, Hiccup's legs still sticking out though. Pulling backwards, Tyne actually pulled their tentacock out of Hiccup, leaving him gaping, and then thrust back in, making both the rider and the dragon groan, two sets of balls getting hit simultaneously.

The Zippleback quickly set a good strong pace, gripping Toothless's ass as they did so, railing Hiccup once more, who in turn was railing Toothless in a way, Hiccup being thrusted about inside and hitting off the dragon's far-to-sensitive prostate. Slamming back and forth, Ivy and Thorn pulled Hiccup's legs further apart, for better access, thrusting deep inside Hiccup, the taste of pre in his throat, amongst the musk of Toothless's cum filled ass.

From Hiccup near constantly sitting on and stimulating their cock, Tyne didn't last long, and within ten minutes they slammed balls deep, starting to cum. For Hiccup and Toothless that was not much change, but at the moment they crammed in, one clawed paw went or Toothless's sack, the other for Hiccup's. Without a shred of hesitation, Ivy's side squeezed Toothless's balls with full force, Toothless entire sack deforming and as they tightened their powerful grip, Toothless already abused balls bulged out around the claws, everything inside crushing and causing Toothless the most pain he had felt the entire time, as because he was so sensitive as well. It was so strong that he couldn't even faint, instead trying to comprehend the pain that was far too much for his capacity.

Also at the same time, on Thorn's side, Hiccup's almost untouched sack was crushed instantly, Hiccup going rigid and yelling out, the pain fresh and new to him, balls mashed between the scales of a left paw. No grip was released, cum pouring into Hiccup at a rate far faster than before, ballooning him and in almost no time making it gush into Toothless, who gurgled from so many things. The twin death-grips were only released when their ten minute torrent finished, both sacks swelling and bruised, and with a swift motion Tyne pulled out, cum going everywhere.

As soon as Tyne did pull out, Ardoa slammed a lever down with her tail, at last disengaging all the bonds holding Toothless, and both the human and the dragon plunged into the chamber of cum below, although both still breathing, Hiccup's air tube not fully in the pool.

"See ya later, sluts!" Shen called out to them, going out of the cave with the others, leaving Hiccup and Toothless to themselves for the first time in a while.

In the pool, human and dragon alike cradle themselves, the relief much better for Toothless, as he'd been needing to for two weeks straight, and the feeling of his own balls in his own claws felt almost alien, but he could tell that they were very swollen, and it would hurt to walk for a month at the very least. As soon as they had fallen in, Hiccup had slipped from Toothless, the tube at long last coming out of his nose, allowing him to breathe regularly again, however musky the air.

About one hour afterwards, both groaned and lifted themselves partially to the side, heads on the stone.

Toothless was the first to speak, clearing his throat. "Well, I'd say that's possibly the best way we could have relaxed." While taking shaky breaths.

"Y-Yeah, I couldn't agree more." Hiccup responded in a sigh of pain/pleasure.

"Heh, well I guess I learned the hard way why you never strike a Monstrous Nightmare in the crotch. You can see where it got me." Toothless said with a grin, licking Hiccup's face.

"Mmm, and I think I've been thoroughly educated on how a sheath works." Hiccup replied, Toothless laughing a little.

"Now, how in the fuck are we going to get out of here?" Hiccup asked with a sigh, looking at the slick cum-stained walls of the pit.

"I have no idea, but fuck that." Toothless replied, yawning, and slipping back into the cum.

"I agree, and I love you bud." Hiccup said, joining his dragon.

"Love you too."

-GriffonTail