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Another of the stories done for my sweet sweet panda, Kenta Snow. A series of posts blended together into a singular story. Not as long as my last, but fear not! 'Tis but the first of a longer overarching saga. Ken and I have an ongoing series of ideas, all of which ultimately join together into a sort of 'expanded universe'. Think of it as the side of How To Train Your Dragon that DreamWorks didn't tell you about.

Usual disclaimer bullshit, if you're under 18 or whatever age the people in charge of where you live have decided you have to be to see smut, you shouldn't be reading this. But let's be honest, even if you are, we both know you're going to read it anyway, so carry on. Just don't blame me when if you get caught! Also, a forewarning, this story does contain male-on-male sexy times, sex between a human teenager and a feral dragon, somnophilia (good ol' sleepytime humpings), voyeurism, and general lewdness and depravity. If any of those things aren't your cup of tea, or are frowned upon by your government, ye be warned! Though again, if you're here already, odds are you aren't leaving even if that's the case.

How To Train Your Dragon, Toothless, Hiccup, Stoick, Gobber, Astrid, Stormfly, and all the rest of the characters, places, and events from said series are not my original work. They are owned by DreamWorks. A huge round of applause to them for their work, btw. (Take that, Mickey.)

In any case, happy reading, and anything else you do while doing so. *Knowing wink.* If you like the story, please let me know!

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Hiccup sighed, staring up at the ceiling of his room as he laid in bed. The moon was starting to dip from its zenith, but dawn was many hours away yet. The house was still, and outside the village had quieted, the normal commotion giving way to the calm of night. But Hiccup couldn't sleep... He had been trying for hours, and nothing had worked. And now, the silence he had initially hoped would bring him peace was in fact only exasperating the problem, as he found that now it was too quiet, and his mind would not rest with the stillness eating at him. He grumbled slightly, cursing the gods for keeping the touch of sleep from him, rolling over in his bed.

A sleepy rumble from Toothless, who was passed out next to him as usual, just made him shake his head morosely. "Lucky lizard," he muttered to himself, seeing the dragon fast asleep, eyes shut tight, muzzle open and tongue lolling out, a bit of drool dripping to stain his pillow, making him shake his head. "No wonder they're always damp in the morning," he murmured, as he reached a hand out to stroke over the sleek black scales of his friend and lover.

"At least you can sleep, bud," he murmured softly, smiling as he saw the dragon's lips twitch upwards in a happy smile, one of the Night Fury's paws twitching in an adorable dog-like manner. It never ceased to amaze him how something so large and intimidating as the black beast before him could be so endearing and adorable, in many ways reminding him more of a playful puppy than a vicious reptile. Chuckling as he heard a happy purr starting up in Toothless' chest, he brought both hands to bear, starting to scratch at the side of his buddy, the dragon beginning to huff and pant happily in his sleep.

"Yeah, you like that?" he murmured, careful to keep his voice low. He knew Toothless could be a deep sleeper, though, and he wasn't overly disturbed about waking him up. Even if he did, it wasn't like his big buddy would exactly be upset by that... Some of their best times had been at night, after all. The dragon squirmed happily, panting like a dog as he felt those hands.

In his dream, Toothless could see his beloved human's smiling face as he rubbed over him, see the sunlight shimmering on the grassy fields as they both basked in their nakedness... Most of his dreams involved Hiccup naked.

Hiccup chuckled softly as he saw the adorable way that his friend squirmed against the mattress, the bed creaking just a bit under his weight. Suddenly, though, the big behemoth shifted a bit to the side, exposing his underbelly to his rider. Seeing those soft underscales, Hiccup smiled and began to rub down over them, the smoother surface always a pleasure to trace over. But soon enough, his eyes began to wander, as they so often did...

He had become so accustomed to it, and before long they drifted down between his dragon's legs. Fixing upon the dampened slit, and more eye-catchingly, the firm, tight rim of flesh beyond. Almost immediately, thoughts began to swim in his head, and he found his heart pattering a bit. He had never tried anything with his dragon in his sleep...

Toothless meanwhile was in the middle of the most wonderful dream... What had begun as just a happy scratch session had moved on to a more intimate belly-rub, and the dragon purred out happily in his sleep, panting as he gazed into those beautiful green eyes of his human. It felt so good to be touched like this... He wanted more, so much more! In his sleep, the Night Fury pressed his belly forward, mumbling woozily out. 'Mmm... Mmmmmorrre... Need you...' he moaned out.

Hiccup's face flushed as he caught the gist of what was said, and he swallowed as his hand drifted lower... Feeling the heat that radiated from the groin of his bud, seeing the swelling of that sheath now. The air tinged a bit with the scent of dragon musth, and he felt his own loins stir a bit.

For a moment he warred with himself. A part of him wondered if it would be taking advantage. What if Toothless woke up and was upset with him? What if he didn't really want this? But then... he had never NOT wanted this... In fact, when one of them didn't, it was always him, and then only for the sake of privacy. He had never once known Toothless to turn down an opportunity to take him... And besides, he had woken up to his dragon slurping over him more than once. Turnabout was fair play, after all... He finally gave a smug smile, shifting closer to the moaning dragon, starting to edge his pants down... His thick uncut shaft pressing free into the night air...

"I guess there's no harm in it," he murmured softly to himself, as he edged himself slowly closer... The night was cool, but near Toothless, he always felt so warm... Slipping off his pants completely and tossing them aside, he slowly eased his way closer. His scent started to fill Toothless' nose, and even in sleep the response was immediate. The dragon gave a groggy, yet very slutty moan, legs shifting a bit, spreading out, baring himself more.

In his dreams, Toothless was burying his nose in his human's underarm, breathing deeply of that heavenly musk that his beloved rider gave off... The scent giving him such a high, his body trembling helplessly both in dreamland and real land. Hiccup biting his lip as he recognized all the signs. "Wow... Guess you want this bad already, bud... Even asleep, you can't turn it off..."

Toothless moaned out louder as he felt the touch of his master running along his body... His dream's eye picturing it as well, albeit a little different. Leaning his head back and cooing deeply, body begging for more... Hiccup blushed as he saw that, moving to start pressing his naked frame to the dragon's own. His thick arousal nudged at the warm belly scales, easing along them, briefly nudging at the leaking slit. Giving it some thought, but looking down, the winking rim of the dragon's tailhole was simply too good to resist... Edging himself a bit down...

Toothless groaned out deeply, seeing in his dream the smiling freckled face he loved so deeply looking into his own as that familiar warm body pressed to him... He could feel the firm touch of the youth's uncut shaft against his scales, making him tremble, wings fluttering a bit, tail thumping in eager joy. Moaning and cooing as he wrapped his arms around the shoulders of his human. Hiccup started a bit at the sudden shift, only to flush as his dragon embraced him, pulling him close. 'Mmm... lllllovvvee... yyyyyouuuu...' the sleeping Fury murmured out, and he shivered as he felt that puckered hole suddenly press to him, his pre leaking over that slick flesh.

"Mmm, I love you too, bud..." he murmured in reply, wrapping his own arms around Toothless, hugging to him... A shaky moan as he began to press inside...

Toothless gasped, leaning his head back and groaning deeply. In his dreams, he could feel as that wonderful human length spread him wide, parting his willing body and slipping past his quivering rim to be embraced by the warm slick flesh beyond. His eyes rolled behind their closed lids, and a loud moan left the sleeping Fury's lips as his toes curled, leaving Hiccup to blush as he gently rested his hand on his lover's snout, trying to quiet the dragon without rousing him. He could feel his own groans fighting to build as he felt that heat wrapping around him, flexing and rippling, seeming to hug him tightly as his shaft flexed in answer. His thick pre leaking to help lubricate that tight rump as he eased himself deeper. "G-Great Odin's ghost... Y-You're always so tight, bud!"

Toothless was a panting mess even in his sleep, his legs splaying even more as his tail curled back away to further offer himself to his trainer. He could hear the moans of passion and pleasure in his dream as his beloved human ground against him, seeing those green eyes more vibrant than life as that bright smile made his heart flutter. Hiccup suddenly started in the real world when the fury pressed his snout to his hair, starting to huff and pant at it, and he blushed as he realized that the dragon was actually scenting him even in his slumber. "G-Guess you really can't get enough of me, can you?" he said sheepishly, even as he quivered in pleasure, feeling himself edging his way slowly deeper. Every inch more that he pressed inward being eagerly hugged tightly by that tight rump, massaged and milked at by the warm walls... Making him pant and shudder, his thick pre soaking over the tight dragon rump as his hood was rolled away by the vice-like grip...

'Ohhhhhh, godddssssssss...' Toothless moaned out softly, shivering and blushing even in his sleep. The feeling of that thick length prodding into him, spreading him, questing into his body... Claiming him in that magical way that only Hiccup was capable of... True, other dragons had taken advantage of Toothless' submissive tendencies since it had become known, but there was something so much better about feeling his human inside of him! His dreams only made it more vibrant, as he felt his human's soft body pressed to his hide... Not yet realizing that he was in fact experiencing the same in real life!

Hiccup panted and moaned deeply as he finally managed to press into the hilt, shuddering bodily as he slowly moved to loop his legs around his dragon's hips. The balance suddenly shifted, and he gasped as Toothless rolled onto his back, leaving Hiccup to rest on his belly, both of them moaning and panting as the human jostled inside of his draconic lover. "Holy Hel," the rider shuddered, before blushing and leaning in to kiss at his sleeping dragon's nape, sending a thrill through the Fury's body. "Mmm, I love you, Toothless," he whispered, slowly lifting his hips up, withdrawing from that tunnel even as it clenched and squeezed to try and keep him in... Only to thrust himself forward once more, driving them together with a soft plap.

As he began to truly get into his illicit night-time romp, however, Hiccup had failed to notice that his door had slightly cracked open... A pair of sharp eyes watching from beyond as the youth began to rock his hips, beginning at a slow and steady rhythm, doing his utmost not to disturb the rest of his draconic lover. The faint, soft plaps of skin to scaly flesh barely audible as the boy bit his lip to try and stifle his moans of pleasure.

It was hard, though... Gods, was it hard. Toothless always felt utterly incredible around him, the way those soft walls gripped and milked along his length, and even in sleep that tunnel seemed to have been trained to react to his presence purely on impulse, working over him with just as much skill as it did when the Fury was awake, possibly moreso. Sweat beaded up on the young Viking's body as he felt his temperature rising, his heart racing as he thought over how he was actually sleep-fucking his dragon, in his bed, with his own father asleep downstairs... The taboo of it all only added to his arousal, and he panted softly as he bent down to nibble and kiss at the exposed neck of his ebony lover, feeling a tremble race through the dragon's body in answer as the great beast gave a groggy little moan. "Mmmph... S-So... hot..." he whispered out, his eyes clenching shut, only to gasp as Toothless gave another powerful flex, his rim seeming to grasp and pull him in deeper, making him shudder as his hips mashed firmly to the dragon's own.

'Mmmmm... Mmmmooorrrreee... Nnnneeed youuuu...' he heard Toothless moan out over him, and he blushed as he gave another little love-nibble. "Mmm, if that's what my dragon wants..."

In his dreams, Toothless could see that sweetly-smiling, freckled face looking down into his own, those green eyes sparkling more beautifully than he had ever seen, brown hair whipped around so charmingly boyish-like. He panted and moaned out, splaying himself, offering his body fully to his beloved human. Not realizing that his dream was in fact happening to him, Hiccup flushing as he saw the dragon spreading his limbs and letting his wings fall limp, laid out in eagerness even as he slumbered on. "Mmm, then that's what my dragon gets," he purred out, a note of huskiness in his voice as he drew back slowly, teasingly drawing his length free of that tight gripping rump, shuddering as it gripped and squeezed at him desperately, his head dragging along those sensitive inner walls...

Taking a moment to steel himself, the youth bit his lip to try and stifle himself, before suddenly plunging forward powerfully! This time a far more pronounced slap rose up as his hips connected powerfully with his scaled lover, the dragon moaning out deeply in his sleep as his prostate was suddenly massaged forcefully, Toothless' own length already snaked over his tummy scales, a jet of pre splashing over himself as he throbbed, yet in that decidedly-slutty way still somehow remained at once fully extended and yet jelly-soft... Their voyeur's eyes widening a bit, taken back slightly by the shift in the usually-subdued youth.

'Ohhhhhhh....!' Toothless moaned out breathlessly, as his dreams exploded into a kaleidoscope of bliss, the background fading to nothing but pulsing color, all focus on the human taking him... He suddenly leaned up to wrap his arms around his lover holding him tight! Hiccup gasping as the dragon's real-life movements groggily followed those of his dreamscape, before growling and smiling as he felt the Night Fury pressing himself to him, trying to roll his hips against him, though his own set the pace. Repeated plaps of his body against the scaly hide striking up a vibrant drumbeat of passionate lovemaking.

Starting to forget about being quiet, the bed jostling a bit as Toothless squirmed, his body responding to the intense pleasure of his prostate being battered and bumped into in the most delicious of ways. The unseen observer's arm already shifting as they found themselves unable to just watch anymore, the itching between their legs growing too pronounced to ignore, trying to keep their voice down, biting their lip... Delicate movements to avoid drawing attention as they watched the naked human so eagerly breeding his mount.

Toothless' rim flexed and gripped, leaking some as Hiccup's copious leakage of pre mixed with the dragon's own natural lubricants and began to spill back. "Mmmph.. W-Wow... I-If you don't mind, I think I'll be doing this a lot more, bud... This is incredible," Hiccup moaned out, his body dripping with sweat now as he felt his heart beating hard and fast. His thrusts were growing far more purposeful now, and his hefty orbs were battering a drumbeat on that tailbase. He was almost surprised that the dragon hadn't woken up from the firm rutting he was getting, but he knew Toothless could be a deep sleeper, and this seemed to be one of those times.

His uncut shaft lancing in and out was was starting to pulse and throb, drawn on by the eager clenches of the dragon beneath him, making him groan and shiver as his pre ran thicker and hotter. He could feel his orbs beginning to work on overdrive, readying to unleash his fertile seed into the squirming dragon beneath him. The bed was starting to creak more as Toothless ground his hips against him as best he could in his sleep, panting and groaning, dribbling from his open maw. Their watcher trying to mask their soft pants...

The dragon panted and shuddered, his rim starting to flex more powerfully around Hiccup's firm thrusts, feeling that thick meat even in his sleep... It made his dreams seem all the more vibrant, all the more real, his body alight with lust and pleasure, desire flooding every cell as his scales shimmered with sweat. Between his legs, his fully erect yet fully limp meat flopped helplessly with each firm thrust his beloved rider made into him, though in his sleep he felt no shame, only desire. He moaned and crooned out deeply, Hiccup gasping and quickly trying to cover the dragon's muzzle with his blanket to muffle his voice, even as he had to bite his own lip to keep himself quiet.

The two were teetering already, the eager, reflexive clenches of the Night Fury's tight rim seizing around the human quickly eroding at the boy's stamina, as the repeated jabs up against the dragon's prostate had his own length leaping and spurting his slick, slimy preseed over both of their bellies... Each movement now growing wetter and more lewd as the soft moist sounds of skin to scales began to rise around the two lovers, Hiccup's hefty orbs plapping to Toothless' flanks with each firm thrust in. The boy's brow furrowing as sweat beaded upon it, his breaths starting to come in ragged pants. Their watcher beginning to grow more hasty with their own movements, even as they tried to remain hidden, trying to stifle their pants and moans...

Hiccup could feel it growing, building in his loins, his balls tightening up little by little as they churned powerfully between his legs. His load being stirred and awoken, gathered up in preparation to unload directly into that tight, gripping tailhole that had him gripped like a heated silken vice. Toothless' own internal balls were similarly building, as the dragon squirmed helplessly, the bed creaking under his weight as Hiccup's thrusts rocked into him with rapidly-building intensity. Sweat fell like rain from the youth as he panted and moaned out, starting to lose control of his voice, hoping to the gods that his father wouldn't wake up... Though Stoick had grown more at ease with the knowledge of his son's special relationship with the Night Fury, the thought of the Chief walking in on them was not one he relished.

The wet slaps grew louder as he felt his own pre gushing back, frothing around that scaly plump rim. "Oh gods, I... I can't... I can't hold it in..." he whimpered, his hips blurring in frenzy, Toothless moaning and mewling in his sleep.

'Fffillll... mmmmmeee... Nnneeed... cummmmm...' he groaned out, sounding somehow even sluttier, as in his dreams he desperately clung to the body of his beloved human.

Hearing those pleading cries filling his ears was too much for Hiccup to bear any longer, and he found himself biting down at Toothless' neck to try and muffle his own yells of pleasure as his loins finally gave. His hips slammed against the dragon hard, slapping loudly against those slick scales, his balls practically spanking that hide as they began to spasm and clench up, violently beginning to unload. His cock buried itself home one last time, seeming to find a way to slide in deeper than ever, and he heard Toothless give a soft squeal as his uncut head slammed directly into his prostate. The dragon's own length quivered as it was pinned between their bellies, and he felt a sudden rush of wet, sticky warmth as the poor Night Fury began to cream himself in his sleep, spewing out his seed over them both, smearing and sticking them together even as the human began to fire off his own thick load deep into the quivering tunnel. The slimy, gooey heat beginning to flood Toothless's rump, whitewashing his insides and flowing back over Hiccup's cock, the dragon giving a deep, lustful shudder as he felt it even in his dreams...

Neither of them noticed as their voyeur lost their footing slightly, biting back a gasp as the sight of the two lovers climaxing together was enough to push them over the edge... Doing their best to catch the resulting mess with their undergarments, but not noticing when a few drops spilled over the floor...

Hiccup spasmed and shivered against the sweaty, scaly body of his dragon, smearing Toothless' sticky steamy spunk around over both of their bellies as his own heavy balls spat out their thick white cream to spatter and slosh about inside of that gripping ass. The Night Fury's moans melding with his humans as he scrabbled his paws at the boy's back, harmlessly scratching at him as his tail flopped about helplessly, crooning as he bucked along with the youth. 'Fill me up...' he moaned out in his sleep. 'Fffffffuuuuck, so hotttttt... Mmmmm, give me your babies....' he purred lewdly as Hiccup blushed hard. The filth from his sleeping bud filling his ears, and causing him to fill Toothless all the more.

"Mmm, that's it bud... Take my seed, like a good hen.... Mmmm, I want to knock you up, bud..." he crooned out, feeding into Toothless' dreamtime ramblings... His words tickling at the sleeping consciousness, the sexy freckled face of the lad beaming in Toothless' mind as he heard those words, making the dragon blush!

A soft gasp leaving their voyeur's lips as they panted, trying to keep their voice down so as not to blow their cover, legs shaking as they carefully leaned against the wall. "Odin's Ghost..."

Hiccup panted and trembled, bucking against those scaly hips as his chest heaved, his balls contracting over and over... The tight, vice-like grip that those warm, slick walls kept on him prolonged his climax, spurting his load to flood the eager dragon until it was running back out, trickling over that scaly tailbase as the poor Night Fury moaned and mewled and trembled in his sleep, tail quivering behind them. The dragon's own seed sticking them together as he shuddered in afterglow, Hiccup finally giving a loud groan of his own. His body releasing the last of his pent-up energy deep into his steed's tight black ass, before he collapsed helpless overtop of the fury. "Mmph... F-Fuck bud... That was... intense..."

Toothless' only reply was a sleepy little moan and mewl, the poor Night Fury having practically cummed himself senseless, collapsing back into the bed with a little shiver as his body settled into a somnophilic afterglow. Hiccup finding himself sprawled out over the dragon as he felt the great beast's warmth radiate into him. The chill of the night only just began to tease at him again, and he was quick to pull a blanket over himself once more, though he was careful not to shift too much, remaining buried in the tight, gripping rear of the dragon under him. Toothless's walls felt amazing, rippling and massaging at him as the dragon purred groggily, his own seed surrounding him like a hot wet blanket...

Beyond the door, their watcher hastily but quietly adjusted their clothes, before swiftly bustling back downstairs, slipping out the window...

Above in their bedroom, the two lovers settled in against one another. Hiccup heard as Toothless' breathing began to settle, whimpers and moans giving way once again to soft, bestial snores, making him smile tiredly as he could feel sleep teasing at his own mind at long last, his eyelids getting heavy. "Mmm, goodnight, Toothless," he whispered gently, giving his dragon one last little kiss, before letting himself go limp, his eyes fluttering closed. Before long, a second set of soft, slow, steady sleep-breaths joined the first, the boy joining his dragon in the arms of the dreamscape.

Meanwhile, across town, the figure of their observer wove their way through the darkened houses, skirting the watchmen with care, finally reaching the hut and forge of Gobber. Seeing a single light burning in one room, they heaved a sigh of relief, before lifting a hand and giving a quiet knock at the door. From within, they could hear a rustling as the house's occupant roused himself from whatever he had been doing within, and the door creaked open, the smith peeking his head out. "Stoick?" he asked in surprise, his face confused. "What are you..."

The question was never finished, as the chief suddenly pushed his way in, pressing his old friend to the wall as he used his other hand to slam the door shut. Gobber's yelp of shock cut off when he saw the look in Stoick's eyes, one he had not seen in many years. His shock fading, as suddenly a smug grin appeared on his lips, and he gave the other Viking a knowing smile. "Mmm, been a long time, hasn't it?" he murmured, and Stoick nodded, a grin of his own appearing.

"I'm calling in that promise you made me a long time ago, old friend," he told the smith, his voice low and deep, and there was a note of pointed, determined desire that was unmistakable.

Gobber just chuckled, before motioning with his head towards the stairs. "Mmm, glad to see you haven't forgotten... And even moreso that you remembered..." he leaned in close, his voice lowering to a husky whisper, "that you don't even need to ask..." With that, he took the Chief's hand in his own, tugging them both further into the house, moving to blow out the candle on the way...

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Will Hiccup find out he and Toothless were watched? How will Toothless take their nighttime fun? What promise did Gobber make Stoick? And how late exactly does a dragon sleep in? Stay tuned for answers!