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Hiccup still couldn’t believe everything that had happened in such a short time. Shooting down a dragon - a night fury - had seemed like it would be the single greatest achievement of his life. All he’d needed to do was find it and bring back proof that he’d actually managed to slay a dragon, and he would finally stop being the village disappointment. The search hadn’t been easy, but he finally managed to find where the dragon had crashed. But when he’d had the dragon at his mercy, in position to make the kill, he hadn’t been able to go through with it.

Looking back on it now, Hiccup knew that he’d made the right choice. Not just because killing a helpless creature had felt so completely wrong to him, but because of the new opportunities his choice had opened up. Things he would have never dreamed possible were suddenly becoming a reality. He’d actually managed to observe a dragon up close, in ways no viking had ever done before. He been able to approach Toothless several times now; once the dragon understood that Hiccup meant no harm, he seemed perfectly at peace with having the boy so close. Hiccup was now more sure than ever that dragons weren’t the vicious monsters they’d always been taught they were. And until he could figure out a way to give Toothless back his ability to fly, he was going to make the most of this opportunity to learn as much about the night fury as he possibly could.

It was as he was heading back into the dragon’s clearing one day that he noticed Toothless acting strangely. He didn’t seem to be able to sit still, settling into newly burned patches on the ground for only a minute or two before getting back up and moving around the clearing, clawing at the walls keeping him contained and whining quietly to himself. Stopping short, not wanting to risk getting to close with the dragon so clearly agitated, Hiccup stooped down behind a boulder on the upper rim of the clearing, peeking around it to gaze down at the black-scaled dragon. Hiccup had been reading every book on dragons he could get his hands on, but the vikings seemed to actually understand so little about dragons that he couldn’t begin to guess what had Toothless acting this way, or if there was anything he could do to help him.

From his hiding place up on the ridge, Hiccup had a clear view down into the clearing, and for several more minutes he watched Toothless, jotting down notes of his observations into his journal, trying to figure out what had Toothless so worked up. When the dragon turned again and his tail flicked in just the right way, Hiccup caught sight of a hint of something pink between the dragon’s legs. He nearly dropped his journal when he realized what the problem was - Toothless was horny! No wonder he’d seemed so worked up and irritable over the last few days. With no other dragons around, and still with no way to get out of the ravine, there wasn’t much in the way of options for dealing with his problem.

Toothless seemed to have realized this as well. Stopping and sitting in one of the burned stretches of forest floor, Toothless bent his head down between his legs, and for a moment Hiccup wasn’t sure what he was doing. But then the wet sounds of sucking and slurping and licking filled the ravine, and the boy realized that Toothless had decided to take matters into his own hands - er, claws - and was licking and sucking at his own penis in an attempt at some relief from his sexual frustration!

Soon, the dragon’s head start bobbing up and down, and Hiccup knew that the dragon was sucking his own cock. As time passed and the boy kept watching, he could feel himself growing stiff inside his pants. Though to be far, a boy his age would be hard pressed to watch anyone enjoying some sexual fun without pitching a tent in record time. Unable to resist the temptation any longer, as quietly as he could, Hiccup loosened and lowered his pants, just enough for his stiff cock to spring out, the tip already peeking out as his arousal grew. He wrapped his fingers around his length and started to stroke and squeeze his dick, doing his best not to alert the dragon to the young voyeur hiding in the rocks.

As Toothless continued bobbing and slurping on his length, every now and again flashes of pink would be visible around his leg or between his lips, but only a little, and only briefly. As his hand worked harder over his cock, he could feel his edge approaching. But before he finished, he wanted so badly to get just a peak at the dragon’s cock. There was a small part of his rational mind thinking about the knowledge he could gain from being the first to observe behaviors like this in a dragon. But most of his hormone-addled mind was just focused on the naughty thrill of seeing another person’s - or in this case, dragon’s - most private places.

As he leaned further around the boulder to try to get a better view, his foot slipped and the load snap of a dry branch cracking echoed through the ravine. Toothless jerked his head up at the sound, a string of saliva leading from his lips to the pink, pointed head of his cock poking out from behind his legs. Sadly for Hiccup, he saw none of this, because as soon as the sound gave away that Toothless wasn’t alone, Hiccup dashed off into the woods, doing his best to tuck himself away as he ran, trying to ignore the discomfort of running with his erection straining his pants, or the wet spot growing across the front as he kept leaking precum, knowing he’d have to find a private place to deal with his erection before returning to the village to get cleaned up. And to find a dry pair of pants.

***********

When Hiccup returned the next day, he did his best to act like nothing had happened, hoping that Toothless hadn’t spotted him. If he had, Hiccup wasn’t sure how the dragon would react, but the possibility of a painful fiery death wasn’t entirely out of the question. Dropping a basket full of fresh fish for Toothless, Hiccup took a seat against one of the small boulders dotting the ravine and took out his journal, sketching the dragon as he ate, making little notes to himself along the edges as he noticed things about the dragon he hadn’t before. It seemed like every time he managed to get up close to Toothless and spend time here, there was something new to learn, some new discovery just waiting to be found.

At first, Hiccup was too lost in his sketching and note taking to really notice, but Toothless was acting rather differently around the boy than he had been before. Toothless had indeed spotted Hiccup when he’d tried to sneak away yesterday, and the dragon knew full well what the human had seen, and what he had been doing. So while he ate, he decided to tease the boy a bit, turning and angling his tail in a way that would give Hiccup a view between his legs, and the slit between them. And the hint of pink starting to show from it.

When Toothless finished eating and moved away from the basket, Hiccup took a moment to look over his drawing, finally realizing the angle he’d been sketching and exactly how much attention he’d been paying to the dragon’s tail end, made clear by the level of detail in his drawing. Detail including the first hints of the dragon’s penis peaking between his legs. But teasing the human with a glimpse wasn’t what Toothless had in mind. The human boy was the only mating partner he had any hope of finding, and he was determined to have his fun. And since the boy had seemed to enjoy watching him so much the day before, Toothless had just the idea to get the human in the mood for some real fun.

Hiccup couldn’t believe what he was seeing as Toothless flopped down on the ground and rolled partly onto his side, his belly facing the stunned human as the dragon lifted his leg to reveal the slit between his legs, and more importantly, the more than ten inches of pink, slick dragon cock sliding out of it to stand proudly in the air, the bright flesh contrasting sharply with the dragon’s dark scales. Almost without thinking Hiccup started sketching, his eyes drinking in every detail of the dragon’s manhood, particularly the series of raised bumps that ran along the bottom of his cock leading up to the arrow like head. A head that was quickly wrapped in the dragon’s lips as he bent double and swallowed his cock to the root in one go, suckling and slurping hard for a few seconds before pulling back and nursing on the tip, his forked tongue collecting his already leaking pre before starting to make shallow bobs as he nursed on his cock, murring at the feeling.

It took only seconds for Hiccup’s penis to grow to a full, almost painful erection that was clearly visible from the tent in his pants at the sight of the dragon sucking his own dick. The sudden aching need he felt, combined with the pressure of his pants against the head of his cock, forced a whimpering moan from the boy, which Toothless couldn’t possibly miss. Letting his length slip from his lips, in moments he was on his feet and sniffing at the bulge in Hiccup’s pants before running his large warm tongue over that bulge of boy flesh, leaving his pants wet and his penis even more eager for attention. But Hiccup wasn’t the only one who wanted his needs taken care of, and Toothless wasn’t about to wait any longer now that he had someone here that could give him what he wanted.

Toothless reared up on his hind legs, planting his front claws against the boulder above Hiccup and to either side of his head, leaving the boy nowhere to go and looking right down the barrel of his slick, throbbing dragon cock. Thrusting forward, Toothless rubbed his dick against Hiccup’s chest, smearing his shirt with precum and covering the boy in his scent. Easing back some, Toothless looked down at Hiccup, eagerly watching the look on the human’s face when Toothless clenched the muscles in his belly several times, making his cock twitch in the air in front of him, grinning at the look on Hiccup’s face as he got a good look at his dragonhood, as well as a couple of shots of pre to the face.

Understanding what it was that Toothless wanted, Hiccup reached out slowly wrapping first one hand then the other around the dragon’s cock and starting to slowly jerk him off, his hands soon slick with pre, letting him move a bit faster. After a couple of minutes, Hiccup looked up at Toothless to see if he was doing a good job, but when he met the dragon’s gaze, he froze. He froze because Toothless was glancing from Hiccup’s mouth to his own cock and back again, licking his lips and thrusting forward to poke at the boy’s face with the dripping head of his cock. Hiccup knew he probably shouldn’t do it, but he had no doubt that Toothless could make him do what the dragon wanted if it came down to it. Though at this point, the young viking was so aroused and excited by such an unusual sexual encounter that he didn’t really care.

Tilting it down to give himself a better angle, Hiccup opened his mouth wide and swallowed as much of Toothless’ dick as he could, groaning as the taste of dragon cock washed over his tongue. Still working his hands up and down the length he couldn’t fit in his mouth, Hiccup started sucking and bobbing his head, drinking down the dragon’s pre and feeling himself starting to leak into his pants at the pleased whimpers and moans of delight coming from Toothless at the feeling of the human’s small tongue and sweet little mouth working over his penis.

Toothless couldn’t help himself, humping forward against the boy’s face, enjoying the way he gagged whenever the pointed tip of his cock squished against the back of his throat and threatened to cut off his air. Whenever he did, though, Hiccup would squeeze the dragon’s cock even tighter, which only encouraged him to do it again, eager to work as much pleasure out of Hiccup as he could. As pent up as Toothless was, though, he wasn’t going to last very long. Before he knew it, he could feel that delicious tingling sensation and warm tightness spreading from his cock and into his belly, a clear sign to any male that the bliss of an orgasm was almost upon him. He started humping faster through Hiccup’s hands and into his mouth, racing towards the finish he’d been after for days. With a roar of triumph, he came, wave after wave of steaming hot dragon cum shooting into Hiccup’s mouth and down his throat, quickly overwhelming the young human, who had just enough space to pull Toothless’ cock out of his mouth so he could gasp for air, but that also meant his hair, his face, and his entire front were soon covered in a layer of hot dragon jizz, each additional shoot only adding to the mess covering him and the ground around him.

When Toothless finally stepped aside so Hiccup could stand, he was positively dripping with dragon spunk, his hair and clothes matted and stuck to him from both the amount of cum and the surprising heat it was giving off. Wiping off his face as best he could, Hiccup knew there was no way he could go back to the village with his clothes in this condition. Since there was no one else around to see him, and acting bashful around Toothless after what just happened seemed pretty pointless, he quickly stripped off his clothes so he could wash them and himself off in the small pond in the center of the ravine.

At first Toothless was confused as to what Hiccup was doing, but he quickly stopped caring once the boy was naked and he got a good look at the human’s body. Even for a human, and especially compared to other vikings he’d seen, the boy was rather scrawny, though that actually made him rather cute in the dragon’s eyes. Compared to the black-scaled reptile, Hiccup’s penis wasn’t really noteworthy, though his five inches were fully hard, the slightly darker head of his cock already mostly exposed and dripping. But what really drew the dragon’s attention was the boy’s ass. Two pale, plump cheeks that just looked oh so inviting. And when the boy bent over to pick up his discarded clothes and Toothless got a glimpse of the pink pucker nestled between them, he made up his mind in a heartbeat. He was going to get exactly what he needed from this boy, and Hiccup was going to love every minute of it.

Hiccup was about to pick up his clothes when Toothless grabbed him, pulling the human over to another of the small, flatter rocks near the shore of the pond and forcing him down on his knees, bending the boy over the rock and nudging apart his legs. Hiccup’s confused questioning turned into a loud moan of surprise and pleasure as Toothless grabbed the cheeks of his ass and spread them apart, eyeing the human’s tight entrance before diving in, burying his face between the boy’s cheeks and lapping over his hole before quickly shoving his tongue inside, rimming and stretching the boy out good and deep, getting him ready for the real fun that was about to start. After all, that tight little body would feel heavenly wrapped around his cock, but he didn’t want to hurt Hiccup. If he hurt him, the boy might not want to does this again. And Toothless was looking forward to many more sessions with his new friend.

When he felt the human had been prepped enough, Toothless quickly got into position, his rear legs planted between the humans to keep him nice and spread, and planting a paw on his back, keeping him right where the dragon wanted him. Toothless let his cock rest against Hiccup’s ass, humping slowly back and forth between his cheeks to let the boy fully understand just what was about to go inside him, and just how big it really was.

When neither of them could take the teasing any longer, Toothless lined himself up, pausing for only a moment when the pointed tip of his cock kissed against the boy’s pucker before sinking in, both their voices crying out at what they were feeling; Hiccup, the feeling of losing his virginity to the wonderfully hot dragon dick splitting him open gently but relentlessly; Toothless, the feeling of a tight, hot, eager to please little ass threatening to crush his cock as he sank into that wonderful warmth, his tongue flopping out as his scaly hips pressed against the boy’s pale white ass, his length fully buried inside the squirming human pinned beneath him.

Pressing down on Hiccup to get as much contact between their bodies as possible - and to enjoy the way he squirmed around that thick length stuffing his ass, Toothless pulled back and thrust forward, quickly settling into a steady rhythm, flooding his body with pleasure that was mirrored in Hiccup’s as he worked every last inch of his dick in and out of the little human, enjoying his squeals and moans of pleasure as his pubescent prostate his hammered by dragon’s big hot dick. And he had been right - the knobs along the bottom of Toothless’s cock felt amazing, Hiccup squealing like a bitch each time one of them gave his whole a little extra stretching.

As it was his first sexual experience, Hiccup wasn’t going to last long, even if he hadn’t had over the inches of dragon cock stuffing him to the brim, the sound of black scaled hips slapping against pale white cheeks echoing across the ravine. Hiccup did his best to hold out, but it only took a matter of minutes before he was crying out in orgasm, his impressive load - though still nothing compared to Toothless’ - splurting against the rock and the ground beneath him.

The feeling of that tight ass spasming around him and milking him so good was more than Toothless could take. Groaning loudly in pleasure, the dragon took the boy’s shoulder in a mating bite, firm enough to show him who was in charge, but still being careful not to injure him as he buried hilted himself inside the human, lifting Hiccup’s legs off the ground as his ass was pushed into the air and pumped full of liquid heat, the dragon’s enormous load bulging his belly and flooding out of him to coat the back of his legs and balls, as well as the dragon’s crotch.

But far from being spent, Toothless was just getting started. Wrapping his fore legs around Hiccup and holding him tightly to his chest, the dragon rolled over onto his back, the human still impaled on his cock, and now even more deliciously helpless with his arms pinned and his leaking cock exposed to anyone who might happen upon them. Human squeals and draconic roars of pleasure rang out once again as Toothless started to hump once again, the force of his hips starting to bounce the wriggling human on top of him, lubed up and extra tight after the first round, Toothless wasn’t letting the boy go until he’d emptied his balls into the human as many times as he could before they both gave into exhaustion. Hopefully, Hiccup could prove his viking strength and last long enough to give Toothless what he wanted, because the Night Fury wouldn’t be tiring for hours yet, and he planned to spend every last second enjoying the human’s body, and showing him all the pleasure a dragon could give if you were brave enough to ride them.