Hiccup's Punishment

Story by GriffonTail on SoFurry

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Hiccup gets punished by Toothless for losing a bet. Set after HTTYD 2. Note: Hiccup and Toothless are in a very intimate relationship ;)


Hiccup and Toothless the dragon are hanging about in the cove, where Hiccup is scribbling notes in his notepad and Toothless is lying on his back, blowing rings of smoke.

"Hiccup, I'm hunnnnngry!" said Toothless to Hiccup in Dragonise.

"Well, do you want to fishing then?" asked Hiccup.

"Yes, obviously" Toothless replied.

"You wanna make it a competition?" asked Hiccup.

"Hmm, sure, why not? But only on one condition."

"What's that?"

"The winner gets to do whatever they want to do to the loser." said Toothless.

"Ok, then." the redhead replied, already planning how to sexually torture the Nightfury.

So Hiccup jumped on to Toothless and they flew to the ocean's edge, on the west side of Berk, where there sat a big flat rock to start from.

"You ready? We stop at noon." Hiccup asked, "Uh-huh" Toothless said. "3, 2, 1, GO!"

The rider and his dragon dashed into the water, Toothless speeding through the water, whereas Hiccup equipped his primitive goggles and baited the fish with worms. The two of them spent the next 15 minutes scrambling to collect fish and add them to their steadily growing piles.

At noon the two of them met at the flat rock, with their piles of fish covered with a cloth.

"I'll go first." said Hiccup, as he revealed his pile of 33 fish.

"Jeez, that's a lot of fish." said Toothless, as he stared at the huge pile. "But this is more." he added with a grin, revealing his pile massive of 52 total fish.

"H-How did you get that much." Hiccup said in a shocked tone.

"Well I am a dragon after all." he replied.

"Lets dig in then." said Hiccup as Toothless lit a fire to roast the fish on.


"Ahhhh, that was amazing!" said Toothless having consumed 20 of his 52 fish.

"Yeah, I'm going to have to agree with that." Hiccup responded.

"Now its time to have some fun." The black dragon grinned devilishly at Hiccup.

"Wha-what do y-you mean?" Hiccup asked nervously.

"You forgot about the bet?" Hiccup gulped at this and Toothless responded with "We will do this at the cove."

When the pair arrived at the cove it was just after noon and Toothless was ready to be relaxed.

"Strip and come here." Toothless commanded to Hiccup, which to Hiccup obliged and stood naked in front of his dragon.

"Now, I have been needing to piss since the morning and your first task is to deal with that." Toothless said as his 18 inch cock came out of his sheath and grew to full length.

Toothless's cock was a monster of a thing, 3 and a half inches thick, ridged all the way through and tapered at the end with a budging 5 inch knot. Hiccup and Toothless were a pretty kinky duo, but Hiccup had never taken the knot. His balls were each 4 inches across and his sack more than twice that, as well as swollen with seed. Being a Nightfury he could cum at least 8 times in a day, and had a never-ending sex drive. On average the Nightfury could cum for a solid 8 minutes.

With a big sigh the dragon released his bladder and a yellow-tinted stream of piss gushed out and onto Hiccup. This went on for a good minute and a half, at which moment Toothless inserted the first 2 inches of his cock into Hiccups awaiting mouth, where Hiccup had no choice but to swallow the warm, steaming, slightly spicy urine. After another 90 seconds, the stream tapered off and Toothless pulled his cock out of Hiccup, whose belly was slightly distended from all the piss.

"That's so much better now." Toothless said contently, as Hiccup got to his feet and walked to the waters edge.

"What do you think you're doing?" Toothless asked Hiccup, and he responded with "Washing myself off, cause we're done?"

"We aren't even started yet! I'm still incredibly horny." Toothless laughed at Hiccup. "Its time to get my rocks off." he said and Hiccup climbed back over to his dragon's awaiting cock.

"If you try to escape during the punishment then you will be even further punished." stated Toothless as he lubed up Hiccup's entrance with his warm salvia.

"Just be gentle." Hiccup said, getting into position on a rock.

"Ok!" Toothless said happily and gently trust the first few inches of his cock into a grunting Hiccup.

The dragon started at a steady pace, gradually adding more inches to the cock in Hiccup's ass, and speeding up as he went. By the time it was about a thrust a minute a whining and groaning Hiccup who had already cum twice, had taken 10 of the 15 inches before the knot, and all of a sudden Toothless stopped at 10 inches, where the outline of his cock could be faintly seen in Hiccup's belly.

Just as Hiccup was about to ask why he stopped, Toothless quickly pulled all of his cock out and thrust back in at a much quicker pace, speeding up to 5 thrusts a second, causing Hiccup to piss himself from all of Toothess's piss in his bladder. As the knot started to bang against Hiccup's ass, Toothless started to pant and thrust harder to get the knot into Hiccup. At this point Hiccup was groaning and writhing on the ground in pure pleasure as Toothless ridges rubbed against his prostate and made Hiccup cum for the third time, which, in turn, loosened up his sphincter enough for the knot to slip in.

Toothless roared and sat back taking Hiccup with him, and as the first spurt of cum splashed out and into Hiccup's anus, Hiccup came again from the sheer pleasure and the heat of the cum. For the next 3 minutes, Hiccup was filled with Toothless's thick gloopy cum as his balls started to drain. After another 2 minutes Hiccup looked 9 months pregnant with quintuplets, and Toothless was _still _cumming at a fantastic rate.

Just then Hiccup said "Toothless, I think I'm gonna pu-" as a little cum spurted out of Hiccup's mouth and nose and onto his severely distended belly. For the remaining 3 minutes Hiccup vomited cum and it came pouring out of his nose. At this point Toothless was sitting back grinning to himself, already knowing what was coming for his rider. After a total of 8 and a half minutes Toothless's stream of cum slowly tapered off, and Hiccup coughed up about a gallon and a half more cum.

"That...was...insane!" panted a very over inflated Hiccup.

"I know!" grinned Toothless, "And the best part is, my knot doesn't go down for at least 3 days, which also means that I stay horny!"

"Wait, WHAT!!!?" Hiccup responded, "I'll explode if you cum any more!" As he struggled to get up, but he couldn't because of the very large knot in his sphincter.

"I told you not to struggle, why didn't you listen?" Toothless said as he picked up a piece of silk string and tied it around Hiccup's erect cock, "Punishment time!"

Toothless then proceeded to expertly rub his ridges against Hiccup's prostate, prompting another orgasm... which didn't come? Because of the string around Hiccup's cock, the cum couldn't travel through his cock, so therefore he was denied orgasm, which cause a very confusing feeling for Hiccup. This continued for a good hour and a half, at which point Hiccup simply fainted from so much denied pleasure. When this happened Toothless lovingly removed the string from Hiccup's cock and with an unconscious grunt Hiccup came, cumming for over 40 seconds, smashing his previous record of 20 seconds. Toothless smiled to himself as he curled up with Hiccup stuck on his knot, and he fell asleep, thankfully laying on his back for Hiccup's benefit.


The next day Hiccup awoke with a feeling of confusion as his memories rushed back to him. As he looked around his scaly prison he accidentally squeezed his sphincter, earning an unconscious thrust from Toothless which caused the cycle to repeat for about 15 minutes. Toothless then woke to a panting and groaning Hiccup, who was covered in his own cum. Toothless smiled to himself, knowing what had happened, and then proceeded to get up on to his hind legs, dragging Hiccup with him.

"Ready for your next test?" Toothless asked Hiccup.

"Test?" croaked Hiccup

"Yes, the flight test!" Toothless responded, and with than he jumped into the air and with a few swoops of his wings they were flying in the clouds.

"Holy Thor!" Hiccup shouted, because when Toothless had leapt into the air, Toothless's cock had somehow been pushed further into Hiccup, causing Hiccup to instantaneously cum.

For the next few hours Toothless swooped and dived through the air, while Hiccup was thrusted into thousands of times, as well as cumming every few minutes and sometimes pissing. Eventually the dragon and the knotted human landed on a random outcropping of rock. Hiccup was panting and because Toothless was nearing orgasm he zoomed back to the cove, landed, and came with the force of a tsunami. Because Hiccup was already overfilled, for the next 6 minutes cum blasted out of his nose and mouth, drenching himself and Toothless.

When he finished cumming Toothless said "Ok, I need to pee now." to Hiccup, who replied with, "No, please don't!" as he tried with all his might to escape the dragon, actually managing to lift himself half an inch off the dragon's knot.

"You never learn, do you?" Toothless said with a sigh.

At this, Toothless curled his paw into a fist and swung it down towards Hiccup. The fist landed directly on Hiccup's testicles, which is when Hiccup stopped moving and gaped in surprise. In the next 5 seconds Toothless delivered 9 more devastating blows to hiccup's limp cock and low-hanging balls. After the punches Hiccup yowled in pain and tried to cradle his aching orbs, but couldn't reach because of his overinflated belly. Effectively it was the ultimate punishment because Hiccup could not provide any relief to himself, so he sat there on Toothless's cock writhing in pain for most of 2 hours, all while pissing constantly from Toothless, which only made the pain worse. When Hiccup started to calm down Toothless whipped Hiccup's sack with his tail, further ballbusting him, until he passed out once more.

When Hiccup awoke again it was the next morning his crotch was in a hell of a lot of pain, all with his hugely swollen balls and cum covered body. Toothless was already awake and talking to a nearby Zippleback. When Toothless saw that Hiccup was awake he grinned and told the Zippleback to go for it. The Zippleback then proceeded to rush over and, without warning, cum all over Hiccup, bathing him in fresh sticky Zippleback spunk, from two huge hemipenes.

"Nice morning bath?" Toothless asked Hiccup, who responded with a groan of pleasure, secretly enjoying the kinky punishment.

"Alright, I think the time has come to release you." Toothless said to Hiccup as the Zippleback flew off, still dripping cum.

Hiccup grunted in agreement as Toothless waddled over to a circular hole cut about 15 foot into the ground and about 6 foot wide. The hole, unbeknownst to Hiccup, was filled with all the excess cum and piss that they had produced.

"Ready?" Toothless asked Hiccup.

"Errmm... sure?" the redhead replied.

With a response given Toothless pulled his still rock hard cock, but thankfully without an inflated knot, out of Hiccup's ass, and with it came an absolute torrent of cum that poured into the pit. At the same time Toothless shoved the first 5 inches of his cock into Hiccup's mouth and came one last time. This time the cum went straight through Hiccup's body and jet-blasted out his ass. This continued for 6 minutes and at the end of it Hiccup was still considerably inflated.

“One last thing." Toothless said, “Stand up with your legs spread" to which Hiccup obliged.

For about 10 seconds Hiccup nervously stood there and then all of a sudden Toothless slammed a thick tree branch up in-between Hiccup's leg and into his balls. There was a crunch as Hiccup was lifted a good 2 feet off the ground and then Toothless delivered 5 last whips to Hiccup's balls and Hiccup moaned and fell into the pit of their combined bodily fluids.

To be continued…

Please tell me about any spelling mistakes, and don't forget to leave a comment.