Hiccup knew that the dragon's brilliant chartreuse eyes were piercing holes in the top of his skull. He laid there a moment longer, frozen, feeling the large now nearly fully erect penis pulsing up against his leg. A small amount of warm thick fluid seeped from the tip and dribbled down onto his calf. Surprised, Hiccup pulled his leg away and rolled over to get out of bed. He grabbed the bedpost to steady himself as he stood and wiped off his leg. Toothless quickly sat up and stared at his rider as he teetered about on his one leg. The dragon huffed, feeling both puzzled yet intrigued. He found the situation confusing as he never imagined Hiccup, being a human, could or would ever share mating behaviors with him being a dragon and yet, one look between the Night Fury's legs would confirm that he still found the contact quite pleasurable. It was obvious to Toothless that his rider seemed upset though so he decided it would be best to either allow his urges to die off or to slip away to take care of himself. He stepped out of the bed and walked a bit awkwardly as his now engorged aching penis swung between his legs. A light trail of pre dotted the floor as he padded across the room.

"Wait!"

Toothless turned and looked back at Hiccup who had returned to the bed and was sitting on the edge. He bit his lip and rubbed the back of his neck as he looked at everything except the large dragon standing in front of him.

"I uh, well I'm sorry. I didn't mean to do that to you. I just thought you would like it, I mean, well, I did anyway."

Toothless turned and sat, listening as his rider continued to babble.

"But if you did like it though, that's great, I mean, I don't mind doing that for you. I'm sure you're lonely and, well, I would be and since you have no one and..."

Toothless grunted amused. His Hiccup was usually extremely clever and concise so hearing him ramble on nervously like this was a rare and rather humorous occurrence. He stood and walked up to Hiccup, nuzzling him reassuringly. He then sat and looked down at his pointed shaft before returning his gaze to Hiccup. Hiccup got the message and carefully sat on the floor next to Toothless, eyeing the foot and a half long member. The dragon stood, giving the viking more room to adjust. Hiccup reached out his hand and noticed it was shaking. He placed it on the dragon's warm smooth flank though and slid it under his stomach. He could feel the vibrations of Toothless purring. He then moved his hand down towards the dragon's hind legs. He heard the purring grow louder and could feel Toothless's body shudder with anticipation. Hiccup sighed and gently placed his hand against the base of Toothless's penis. The purr transformed into a low satisfied groan. Encouraged, Hiccup began stroking the large organ. It was too large for him to grasp in one hand but not so large that it was uncomfortable to hold or fondle. He reached up and gently touched the impressive display of masculinity with both hands. He discovered that he was able to wrap them both around the girth easily. He held it a moment before gently squeezing, eliciting a moan of pleasure from the dragon towering over him. The large penis deepened in color and the small bead of pre on the tip finally dripped free as Hiccup's hands slowly and gently traveled up and down its length. He could feel it pulsing in time with the dragon's heartbeat but it would twitch or wag slightly in his touch which made it seem even more alive. He finally worked his way up to the tip. It tapered into a fine point and there were a few ridges on the underside. Hiccup gently rubbed his fingers over them and jumped when Toothless whined quite loudly. Clearly, this was a very sensitive spot. He was surprised at how vocal Toothless was and was feeling rather turned on by how candidly his dragon was expressing his pleasure. His cock bobbed and started drip with more pre as Hiccup continued to finger all around the tip. He watched fascinated as the long shaft stiffened and stood up in response to his touch and then sagged under its own weight. Furthermore, the sound of Toothless's whining was music to his ears.

Toothless found the light titillations undeniably pleasurable but the young man's clever little hands were merely teases to his straining cock at this point. The dragon wanted more as his turgid member continued to twitch and leak, begging for firmer touch. Hiccup was having too much fun exploring though to hasten along. He took one hand and steadied the seemingly alive organ and with his other hand, he took a single finger and gently pressed it against the opening of the tip. His finger pushed inside slightly. Toothless knew Hiccup wanted him to stay still but that felt so good. Sparks of pleasure shot through his entire body. He moaned loudly and rolled his hips forward. A new bout of pre shot out and coated Hiccup's finger. He pulled his hands away and studied the clear warm viscous fluid as it ran down his finger and hand. Hiccup also noted that Toothless now had a very distinct scent. It was strong and a bit musky but overall, pleasant if not alluring. A sharp whine from Toothless got Hiccup's attention though. Clearly, the dragon was feeling neglected from the severed contact. Hiccup chuckled.

"All right all right."

He placed his hands back on the large organ and began tracing over the various ridges and veins that ran along its length. Occasionally he'd hear Toothless hiss when he touched a certain place. He'd make a point to press and rub against that spot just to egg the dragon on and coax more of his juices out. He gradually worked his way up and down the shaft, pushing into the back of it with his fingers and kneading the underside of it with his thumbs. He didn't want to leave a single spot untouched. He could feel Toothless shuddering above him as he emitted low drawn out sounds that were a unique combination of growling and purring. That along with the involuntary rocking of his hips assured Hiccup that his friend was thoroughly enjoying the exploration of Hiccup's hands along his throbbing member. No longer fearing that he would hurt Toothless, he decided some stronger contact would be appreciated. He grasped the hot flesh with both hands firmly and squeezed, hard. Toothless's breath caught as his legs suddenly gave out. He slumped back and his large talons scraped and dug into the wood floor. Hiccup held tight though. The dragon remained still and continued to pull back as he began to whimper with pleasure. Hiccup gave the massive cock a playful tug. Toothless groaned and wriggled in the young man's grasp. A thick string of Pre strung from the tip down to the floor as the large organ leaked. Hiccup grinned mischievously and tugged again. Toothless whined loudly as he body spasmed from the sharp hits of pleasure that shot down his spine and flooded his entire body. Hiccup decided he liked making his typically formidable companion practically helpless with bliss.

He released one hand and placed it under the tip. He rubbed his fingers quickly over the ridges on its underside. Fresh slick dribbled out and coated his hand. He then reached down, removing his pants, to tend to his own aching penis. He began to rub it. Hiccup gasped. The warm clear fluid felt unbelievable on his uncut cock. His hand slid effortlessly up and down his length and the idea that he was masturbating with the juices of his dragon was driving him crazy. An exciting prospect crept into Hiccup's mind. Although Toothless's penis was considerably larger than his own, its tapered end made for easy and precise contact. Hiccup pulled back his foreskin and gently positioned the pointed end of Toothless's just beneath the exposed head of his own penis. He held them firmly together in his hands. He suddenly noticed something looming above him. Hiccup grinned. His nosy dragon had turned back and stuck his massive head right in front of Hiccup's so he could investigate what was going on. He intently stared down at both of their members held tightly in Hiccup's hands. Being so large yet flexible apparently had some unexpected benefits. Toothless decided to resume a more comfortable position to enjoy the spectacle though and sat down in front of Hiccup. Hiccup released one hand and began to slowly jerk himself as he tightly squeezed and held Toothless's penis in place with the other hand. It felt incredible having the contact of his hand and Toothless's tip on his member at the same time. The dragon's hot breath on his face and neck as he panted reaffirmed that his friend was enjoying this as well. He could feel drops of saliva occasionally slipping off of his friend's tongue onto his shoulder and running down his back. Hiccup did his best to hold his friend's large penis in place as his hand moved faster and faster on his own. Toothless's eyes were shut and occasionally he'd allow his tongue to slap against Hiccup's face as a sign of gratitude and encouragement. Typically Hiccup hated it when Toothless licked him but now he could not care less. In fact, it actually enhanced the experience, knowing how much his friend was enjoying this. He moaned as he neared his limits and pressed his forehead against Toothless's smooth broad head. He held his breath as he strained one last time, his hand moving furiously over his penis. The pre that was now almost continuously leaking from Toothless's penis made for excellent lubrication as Hiccup's member vigorously moved over and against the dragon's tip.

"Oh gods! Toothless...ah, Tooth..."

The large dragon opened his eyes in response to his name but remained where he was. He looked down and watched Hiccup clench both of their cocks firmly together as several strings of white semen shot from Hiccup's penis onto his own. The dragon moaned at the tightening grip on his member. As Hiccup's climax slowly ebbed, he loosened his grip and allowed his softening penis to slowly slide over the warm slick surface of the much larger, still engorged member of his friend. Still winded, Hiccup looked up at Toothless.

"That...that was incredible bud..."

Toothless grinned down and his rider and slowly licked his neck. He then curiously sniffed the white fluid that Hiccup had spattered along the length of his shaft. He crooned thoughtfully and proceeded to lick at some of it. His hips rocked forward involuntarily the instant his tongue made contact with his penis. Despite having just having one of the most glorious orgasms of his life, Hiccup found the idea of Toothless pleasuring himself with his tongue beyond arousing. His confidence was growing but still, this was his first time with Toothless. He wanted to see what Toothless did to himself so he could learn what he liked most. They young man figured he could be still useful even as he basked in his afterglow. He sat up and watched the dragon as it continued to lick at its cock. Hiccup took his hand and pushed Toothless's penis up slightly and held it still so the dragon could preen it more easily. The dragon growled hungrily as he lapped up the remnants of Hiccup's seed and to the young man's pleasant surprise, proceeded to take his tip into his mouth and gently chew and suck. How convenient it was to have retractable teeth! Hiccup slid his hands down the large veiny cock and grasped it near the base. Toothless released his penis to look down at his helpful little friend. He grunted with pleasure and appreciation before standing and taking his penis back into his mouth. Hiccup pushed the stiff organ upwards and even farther into the dragon's mouth. A moan of pleasure escaped Toothless's throat and the vibrations that made on his penis almost caused him lose his mind. His hips thrusted forward, forcing his penis even deeper in his mouth and into his throat. Guttural sounds of pleasure continuously sounded as Toothless bit down and vigorously sucked on his throbbing penis. His hips rhythmically thrusted forward and his warm hot saliva along with the copious amounts of slick, made for easy passage in his mouth and kept him from gagging when the tip pressed into the back of his throat. The bumps along his gums and the ridges in the roof of his mouth made for surprisingly wonderful friction as well. As he continued to bite and suckle himself, excess pre and saliva escaped the dragon's mouth and slid down his shaft onto Hiccup's hands. Hiccup continued to squeeze and pull at the base of the organ and gazed upward. Almost half of it was engulfed in Toothless's mouth as he continued suck, lick, and chew. The dragon pressed his tongue against the ridges and veins that ran up the length of his shaft and an almost pitiful whine would signify that he had made contact with a particularly sensitive spot. It was obvious that he had done this before and knew exactly what he liked done with his cock. Hiccup couldn't wait to learn all of those places and be the one to make his friend whine in ecstasy like that. He found it remarkable and incredibly hot that Toothless could pleasure himself this way but it also made him sad knowing he did it out of loneliness and the desire to find release.

The Night Fury's large expansive dark wings flared outward and flapped occasionally to maintain his balance in this slightly unnatural position. His tail slammed against the floor with pleasure as he nursed himself with Hiccup milking him from below. Hiccup noticed a large firm bulge just beneath the slit between Toothless's legs. With his friend shrouded in arousal, Hiccup figured it was more than safe to move his hands down to where the large organ emerged from the dragon's body. He gingerly pushed the sides of the slit apart and slid his hands inside. It was incredibly tight, slick, and hot. It then dawned on Hiccup that Toothless had a knot. He wondered if, with enough stimulation, it would eventually emerge as well. The shear size of his dragon astounded him especially now, having discovered that there could be more to come. The intrusion from Hiccup's hands was apparently welcomed as the small viking was almost knocked backward by a particularly violent thrust. Hiccup grabbed onto the large bulbous knot to keep himself from tumbling backwards. That sharp abrupt tightness inside of him was enough for Toothless and he was pushed over the edge. With his cock still held firmly in his mouth, he whimpered before letting out a deep moan that resonated with lust. He threw his hips forward a final time and Hiccup felt the massive penis he was clasping onto surge and pulse in his fingers stronger than ever before. He turned and watched the shaft jolt as what he could only imagine were ropes of semen shooting out of the tip and deep into the dragon's throat. His imagination served him well. The dragon had clearly been holding out for quite some time. He thrust forward several more times as he released multiple loads. Despite keeping his mouth firmly closed around his cock, he couldn't contain it all. Excess seed seeped out of the corners of Toothless's mouth before it poured freely and ran down his neck. It's white color was striking against his ebony colored scales. His thrusts finally eased as the last of his semen was pumped from his body. He continued to gently hump his mouth though as he allowed his penis to gradually slide out from between his lips. He moaned and nibbled at the tip before finally parting his jaws and allowing the large sopping organ to fall free.

Drool and semen dripped and pooled everywhere on the wooden floor. Toothless slumped forward with his large glowing eyes lidded as waves of pleasure rippled through his body. His tongue hung loosely over his lips as his panted heavily. After a few moments he exhaled deeply and looked down at Hiccup who was still between his hind legs with his hands buried in his slit and firmly around his knot. The young viking's face was plastered with astonishment and desire. Toothless crooned, both satisfied and amused, and leaned back slightly. Hiccup shook his head, freeing himself from his erotic trance, and quickly took the cue to release his friend. His slippery hands easily slid free. They felt cold being outside and divorced from the dragon's incredible warmth. Toothless moaned and shook all over one final time as the last of his seed dripped from his penis. He then slowly sunk to the floor and rolled onto his side. He reached out with his front paws and pulled Hiccup down with him. The young man tumbled forward into the large fatigued reptile and chuckled. He situated himself on the floor against his dragon and smiled. He yawned and turned into his friend's embrace burying his face into the dragon's warm, broad, vibrating chest. He noticed that Toothless's spent organ hadn't fully retreated yet as he felt it twitch when his foot accidentally bumped against it. Toothless didn't seem particularly bothered though and hummed contently. Hiccup could only imagine what he and Toothless could now do together as their relationship grew and they continued to explore this new realm of intimacy. He reached up with his arm and wrapped it around the dragon's muscular neck, pulling them even closer together.

"You are amazing bud...I love you..."

Toothless drug his tail lethargically across the floor and draped a dark expansive wing over both his head and Hiccup, who was nestled against him. He trilled softly and hugged the small viking to his chest. The feeling was undeniably mutual.