After a further week of daily visits, Hiccup was once again in Toothless and Jack's apartment, once again drawing the older teen nude. Jack was standing on a chair in the middle of the living room, completely bare to Toothless and Hiccup, the former of which was preparing dinner in the kitchen, his hard-on pointing to the ceiling.
"It's…it's my first time drawing a…y-you know…" Hiccup trailed off, blushing crimson, his own little peen stiff in his jeans as he ogled the unabashedly naked snow kissed teen in front of him.
"I trust your skills." Jack winked, clasping his hands behind his head, a bead of precum dripping from his tip.
Hiccup nodded and started his drawing. It was a slower process than before, he was more used to drawing Jack from behind or the side. Drawing his more detailed front, especially with his member on such lewd display, was more difficult. It didn't help that Jack didn't stop grinning at him, acting as if he wasn't the one on display.
"Done…" Hiccup whimpered, unsubtly palming his erection through the front of his jeans. Jack hopped off the chair and took the offered sketchbook. He whistled when he saw the drawing.
Bar the colour, it was an almost spot-on depiction of his oh so handsome self.
"You've outdone yourself, Hic." He said, ruffling the younger teen's hair. "You, know, you're gonna hafta let me draw you one of these days." He said, eyeing the boy up and down. "Seeing as you get to see me naked so much." Jack purred in a teasing manner.
Hiccup blushed but didn't shoot the idea down. He supposed that it would be only fair, but that didn't make the notion of being nude in front of Jack, and probably Toothless too, any less daunting.
"Now," Jack said, handing Hiccup his sketchbook back. "I've grown a little problem to take care of before dinner's served." He winked again, nodding down to his still throbbing cock.
Hiccup nodded with a repressed grin. Just thinking of Jack doing that made him want to do the same. The only problem being that he a bit more tact than the other teen and wouldn't assume he could jack-off in someone else's home.
Jack ascended the spiral staircase, Hiccup watching his shapely rear as he did. Now it was just him and Toothless.
Hiccup always felt nervous around the man. Not because he was intimidating or scary, but because he was just so…much. Being around him you could tell that the man knew a lot, he gave off an aura of someone who knew the secrets of the world and could, with a word, undo everything you knew about society and yourself. On top of that he hid all of this behind a stoic, friendly smile and warm, green eyes.
"While he's up there handling himself, you wanna give me a hand here?" Toothless asked in a light, sing-song voice.
"S-sure." Hiccup stuttered, carrying the chair Jack had been standing on back to the table.
He helped toothless prepare the meal, doing a few small tasks for the man while he hummed a tune Hiccup didn't recognise. The smells of cumin and paprika filled the small apartment as the pair left the mince-meat to simmer.
"You know, I might need you to draw me too at some point." Toothless said as they strolled into the sitting room, his voice akin to melted dark chocolate in Hiccup's ear.
"Y-Yeah?" Hiccup blushed. He couldn't help but look the man up and down. He was solidly built, not quite a tank but not as lanky as Jack either. The best way he could define it in his own head was that it was like a swimmer's build.
"Yeah. But not now." Toothless plopped down onto the couch and stretched. "And, if you want, you could go upstairs and join Jack, I know he'd like it and, excuse my assumption, so would you."
Hiccup's ears went red. Of course he would like to, the thought of it invaded his dreams and occupied his waking fantasies. He never presumed upon it, but…
"I, I…" He gulped and looked to the spiral staircase. If he strained his ears he could hear the bounce of bed springs as Jack worked away on himself.
"Don't if you don't wanna," Toothless said, raising his hands. "just a friendly suggestion."
Hiccup looked longingly at the spiral staircase. His member was stiff in his tight feeling briefs, egged on by the thought of walking up those steps and joining Jack in his activity. He took a tentative step towards the staircase, but the sounds of bedsprings stopped and he heard Jack sigh in relief.
"Oh...looks like you missed your chance." Toothless lamented, standing up to go and check on the dinner.
A few moments later, Jack came down the stairs again, a dopey look on his face as his black shorts sagged on his hips. They left nothing to the imagination, not that Hiccup would need to rely on his imagination to know what Jack looked like without them, but still. He could see the outline of the other teen's flaccid member in them and they sunk almost halfway down his rear. Any sudden movement would probably send them down to his thin ankles.
They sat together for a round of Mario Kart while Toothless finished up the last bits and pieces of the dinner, which was tacos. The two sat around the kitchen table as Toothless brough over a rack of corn shells and the bowl of meat, which smelled amazing.
"Thank you, Toothless!" Jack declared as he began to salivate, not waiting to dig in. Hiccup followed suit but with a bit more restraint.
"Yeah, thanks!" He added, being very careful with the ladle of chili as he poured in into his shell, topping it off with a decent handful of grated cheese.
It was delicious, as expected, but also hot! Hotter than he expected. The inside of his mouth burned. His cheeks went red and tears brimmed his eyes. Yet he didn't stop eating, not only was it still very tasty, the last thing he wanted was to offend his hosts, who both seemed to enjoy the food with no bother.
Well, Toothless was unbothered, Jack still showed some symptoms of feeling the heat but nowhere near as much as Hiccup did.
"Want some milk?" Jack asked, standing up and fanning the flames in his mouth.
Hiccup swallowed a mouthful and nodded, wiping a tear away with the back on his hand. He downed the glass in almost a single gulp. Fortunately, Jack brought the entire carton to the table with him.
Hiccup went through a second taco, still feeling the intense yet delicious heat. But then, he felt something, something that made him stop chewing and filled every fibre of his body with utter dread.
He stopped chewing and dropped his taco. He pushed back from the table and stumbled out of his chair, falling to his knees as he cupped his hands over his crotch.
"Hiccup?" The other two called out, both of them very concerned about his sudden departure. He couldn't look at them. It was too late.
He should've known better! The spice had been too much for him and now it was too late.
He stood feebly on his trembling legs, barely making it two steps before it started. He felt a trickle drip from his willy despite his best efforts to keep it in. Trying to stop himself from going physically hurt but he would die before he let it happen.
"Hiccup?" Jack was next to him, a hand on his shoulder, a look of pity and concern in his eyes. "Let go." He said, rubbing soothing circles into his back while looking deep into his eyes.
The younger teen let out a sob as tears trickled down his cheeks. The sheer humiliation of the situation he found himself in made him wish the ground would swallow him whole. "Come on…" Jack said, his own hands going to Hiccup's. "It'll be easier this way." He promised, gently pulling the boy's hands from his crotch. Hiccup felt another volley of sobs constrict his throat as he did as he was asked and let the flow go free.
It felt disgusting. A wet and warm patch enveloped his groin before leaking down his legs. He clenched his eyes closed, keeping a firm hold on Jack's hands as the moment seemed to drag on forever. He felt his heart almost collapse in on himself when his wee soaked into his socks and spread across the kitchen tiles.
And then it was done, a few more small squirts and he was empty.
"S-s-sorry!" He sobbed, unable to look either of them in the eye. He wondered what they would think of him now. Would they send him off, never allowed to return? Would they mock him? Tease and taunt him? The notion made him want to vomit more than the humiliation did.
"Hey, it's okay." Jack soothed, cupping his cheek. "Accidents happen." He cooed, leaning in and pressing a kiss to Hiccup's forehead.
The boy couldn't even register the touch of affection before Toothless was there on his other side. "It's okay, kid." Toothless added, a hand securely on his back. "But now comes the harder part." He said, remorse in his eyes.
Hiccup tried and failed to repress a sob and nodded. He moved his trembling hands to his button and zipper and fumbled them, too addled to get them open.
"Let me." Jack said, quickly unbuttoning and unzipping his jeans. Hiccup let out another sob as they and his soaked briefs were pulled off his hips and down his legs. He would've blushed in embarrassment at being denuded so casually but he was maxed out as far as humiliation went.
Toothless then pulled Hiccup's shirt over his head, leaving him with only his pants and underwear at his ankles as Jack pulled off his sodden socks.
A moment later and Hiccup was completely naked, his small and hairless cock and balls out for them to see, along with the rest of his skinny and pale body.
"Come on, this way." Toothless led him by the hand over to the kitchen sink, where a chair was already waiting for him, a towel draped over the seat. He flushed crimson as he deduced what was about to happen but didn't put up a hint of protest. He owed them at least that much after his shameful display.
"Up we go." Toothless said, helping him stand on the chair, just as Jack had done earlier when posing for him. He felt so exposed, so bare to everything. He caught Jack's eye. The other teen was in the middle of gathering up his wet clothes, a prominent tent bulging the front of his shorts.
In a strange way, he was happy he had that kind of effect on Jack, that he was able to get him to such a state with nothing but his naked body. His attention was arrested from Jack when he heard the faucet go off. Steaming hot water filled the basin, a soapy lather forming as it filled more and more.
Toothless began to hum again, just as he had when making dinner. He dipped a fresh cloth into the warm, soapy water, wringed it and ran it up the outside of Hiccup's left leg. The boy trembled at the contact. He hadn't been washed like this since he was about five or six, having it be done to him at age thirteen was downright humiliating!
Still, at least Toothless and Jack were being very gracious about it.
The man went on with his cleaning, running the cloth up and down his legs for a while before sliding the rag up the inside of his thigh. Hiccup couldn't help but squeak when Toothless grazed his balls, no more than he could help his cocklet growing stiff.
He felt compelled to cover it but didn't, not wanting to get in the man's way.
Toothless then went up the other thigh and had him turn on the spot. His freckled round butt was the only part of him that wasn't scrawny as heck. Toothless approved if his whistle was anything to go by.
"You're cute everywhere." He chuckled as his hand ran across Hiccup's pert cheeks. The boy stiffened and blushed completely at a complete loss as to how to respond.
It seemed that Toothless didn't expect him to and continued his cleaning, going up and down the backs of his legs, and up the insides of his thighs again. What he didn't expect was for Toothless to pull one of his cheeks aside and swipe the damp cloth up and down his crack more than a few times. He couldn't stop a moan from leaping from his throat as his pink hole was glossed over. He clasped onto the back of the chair and bent forward, pushing his rear-end outward.
"You like that, eh?" Toothless asked, leaning in and resting his chin on Hiccup's shoulder. Hiccup, realising what he'd done, stuttered and stumbled to find a response.
"It's cool." Toothless chuckled. "Jack's the exact same. One touch back here," He emphasised the point with a wet prod of the rag to Hiccup's back entrance. "and he turns to putty in my hands. Would you like a taste? Jack's not here to see." He asked in a deep, husky tone.
Hiccup flushed scarlet at the proposition but he couldn't help but be intrigued. He'd only ever experimented in complete privacy, never daring to do more than a nudge in here and there. But to have someone with experience, like Toothless, play with him there, the offer was just so much.
"If you don't say anything, I'm gonna take that as a yes." The man said, a finger poking at Hiccup's pink hole while a hand went around to rest on his stomach. "Y-yes!" Hiccup lurched, backing his rear onto Toothless' digit.
"Thought you'd say that." Toothless smirked. With that, he made his prodding finger glow green, a translucent gel leaking from it as he poked a bit into Hiccup's virgin entrance. "If it becomes too much, just tell me to stop and I will."
Hiccup nodded. His back arched as he felt himself properly breached for the first time. He bit his lip as a brand new sensation overtook his lower half.
"Oh!" He yipped, crossing his ankles and clenching his toes as his member stood to full attention. He bit his fist when Toothless edged in an inch more and pulled out again.
"How was that?" The dark man asked, rubbing Hiccup's soft tummy to soothe any misgivings.
"G-good." Hiccup admitted, his knees knocking.
"Then, I'll go on." He whispered into the boy's ear.
And on he went. Toothless inched his finger in to the knuckle, touching parts of Hiccup that hadn't been touched by another person before. He felt so stuffed! So full, like there wasn't any space back there at all. Yet Toothless delved further in, his finger ghosting against that spot in him.
"Toothless!" He cried, clapping a hand over his mouth.
"You okay?" The man asked, ceasing any further movement.
"P-please! Touch it." He begged, backing his rear onto Toothless' finger.
The man chuckled, and without another word, he curved his finger and pressed onto the spot that made Hiccup see stars! The boy shuddered and moaned as tremors bounced and vibrated through the entirety of his tiny body, moans jumping from his throat against his will.
Toothless saw his chance and wrapped his fist around Hiccup's pulsing member with the cloth, stroking and pumping it in time with his pushes on the boy's delicate P-spot.
"Oh, oh- OH~!" Hiccup moaned, his chest heaving as he bucked into Toothless' fist. The coil in his gut snapped like elastic and he squirted strings of watery cum into the damp cloth.
He slumped, his breath heaving.
Toothless pulled his finger out and continued to wipe down Hiccup's crotch and legs with the cloth as if nothing out of the ordinary happened. As he finished, Jack came down the spiral staircase, a steaming towel in hand, his loose shorts still sagging down his hips.
"Did I miss something fun going on down here?" He asked with a childish pout.
Hiccup and Toothless looked at each other and grinned. "Only a little." Toothless cheekily insinuated with a wink.
"Hmph!" Jack turned his nose up at Toothless and nudged the man out of the way. He smiled at Hiccup and enveloped him in the towel. Hiccup suddenly found himself nested in a cocoon of warmth, a chill he didn't know he had felt vanishing. Not to mention, it felt nice to be covered up again. Jack took Hiccup into his arms, carrying him like a bride to the couch and plopped them both.
"You feeling any better?" He asked the nude boy as he rubbed the fluffy towel up and down his wet legs.
Hiccup nodded, a red tint colouring his cheeks. His…activity with toothless had made him momentarily forget that he'd wet himself like a little boy.
"Don't mind me, I'm just gonna clean up after the dinner I made." Toothless snarked from the kitchen, tossing plates and cutlery into the sudsy water he'd been washing Hiccup from.
"Thank you." Jack replied, pulling Hiccup in closer. "But, do tell, what'd he do to you to get you moaning like that?" He asked, leaning in close and whispering in Hiccup's ear.
The boy went red at the thought of saying it out loud. It also lit something in his groin that would've made him stiff had he not cum only a few moments ago.
"He…he put his finger up my…you know, and pressed on the…t-the thing." Hiccup managed to stutter out, his neck, chest and ears all going deep scarlet as he spoke.
"Really?" Jack said, genuinely surprised. "He waited a while before doing that for me." He said, his lower lip puffed out. "Lucky kid." He placed a kiss on Hiccup's cheek, enjoying how flustered it made the boy.
"Oh come on, you just got fingered to orgasm, a kiss can't be too much for you." The older teen chuckled, pulling the towel out from under Hiccup, leaving the boy bare once more. His hands rushed down to cover his modesty, a gesture Jack found immeasurably adorable.
"I've never been…" Hiccup paused, his hands wringing over his junk. "Kissed..." He finished, burying his face in Jack's neck.
"Really?" The older teen asked, a brilliant notion dawning over him. "You want your first one?" He brought a hand up to Hiccup's cheek and brought him out of his hiding spot. He looked deep into those forest green eyes. Despite being a similar colour, they were nothing like Toothless'. Hiccup was a meek and timid soul whereas Toothless was fiery and explosive, though he hid it well.
Hiccup felt his heart pound in his chest. The idea of Jack of all people being his first kiss was mind-addling. He thought of it before during his nightly fantasies. Almost every time. He often found himself wondering what they would feel like, what they would taste like, and whether or not he'd be any good.
"Y-yes." He muttered, his every limb trembling.
"Hoped you'd say that." He smirked. He shifted Hiccup's position so that the younger teen was straddling his lap. He raised his hips and shook his shorts, which were already down so far that his trimmed white bush was visible and his bare cheeks were out, down the rest of the way. He kicked them off his ankles and enjoyed Hiccup's reaction to them being so close naked.
"Now those go here." He said, pulling Hiccup's hands away from his boyhood and resting them on his own shoulders. "Much better." He said, biting the inside of his cheek when he glanced at the boy's hard-on. In a single movement his own popped up from under Hiccup and the pair were parallel to one another.
Jack rested his hands on Hiccup's hips and licked his lips. His body and mind wanting to give the boy a noteworthy first kiss. Jack's hands slithered around and cupped Hiccup's soft, round cheeks. His reaction was worth it. He was already red and flustered and this only added to it.
"You like that?" He asked, grabbing a cheek in each hand and pulling them apart. He ran a finger down the middle and lightly prodded his hole. He wasn't going to do what Toothless did, but a little teasing couldn't hurt.
Hiccup buried his face into Jack's neck. His breath hitched and he clenched his rear. His cocklet dripped a small bead of white and he bucked into the older teen's member.
"You're very sensitive there, aren't you?" Jack asked, sliding his hands away from the boy's behind. He brought him out of his hiding space and tilted his chin up. Their faces were only inches apart.
Jack smirked, feeling like he could get lost in Hiccup's eyes. It was like looking into a lush forest that was teeming with life. He imagined walking into the brush and getting tangled in a mess of vines and resting there for the rest of time.
Jack leaned in. His eyes drooped closed and he brushed his lips against Hiccup's. It was so gentle that it could've been a ghost, but it wasn't. Hiccup let out a deep breathe and leaned in too. He didn't know what to do, so he just puckered his lips against Jack's. They were cold, but not in an icy, freezing way. It was more like pressing his lips against an ice-cube on a sweltering summer's day.
It was a relief, something he wanted more of.
Jack brought a hand up to the nape of Hiccup's neck, keeping him steady as he went in harder. He parted his lips and slipped his tongue out. That caught Hiccup by surprise, but he too opened his mouth just the tiniest bit and let Jack in.
The older teen was careful not to be too forceful. He slowly ran his tongue across Hiccup's, slowly and gently coaxing him to play back. He moved his free hand to the small of Hiccup's back and pulled him in closer so that their cocks were squashed in between their bodies. This made Hiccup moan and clench down on Jack's shoulders.
A moment later, they parted for air.
"How was that?" Jack asked, his hands settling on Hiccup's velvety cheeks again.
"A-amazing. Unbelievable!" Hiccup answered through heavy breaths. His heart was pounding, his member throbbing, his chest heaving! He just had his first kiss! And it was a great one too! He'd bet his drawing hand that not one of his peers had a first kiss that amazing.
"Good to hear." Jack winked. He ran a hand through the boy's hair and brought their foreheads together. "Now, to take care of our other problems." He smirked, his eyes dating down.
Hiccup flushed crimson and nodded, ready to let Jack to whatever he wanted to do.
Jack shifted their positions, with Hiccup now sitting on the couch and he himself on the floor, kneeling between the boy's shaky spread legs. He didn't say anything, but with a look and a smirk he let his intentions be known.
Hiccup gulped when Jack's hands ran up and down the insides of his thighs. The older teen pushed them further apart, giving him better access to Hiccup's bald, barely pubescent boyhood. Jack licked his lips and pinched the base of the cock. He stroked it carefully a couple of times before pulling the skin at the tip back, revealing the bright pink, sensitive glans.
Hiccup mewled, his toes curled and his hands trembled.
Jack smiled at him, giving him one last wink before he brought his lips to the pink tip, kissing in gingerly before sliding the whole cock into his mouth.
Hiccup's chest fluttered like a swarm of butterflies as he moaned out loud, his back arching as a new sensation of warmth and wetness enveloped his most sensitive part.
"J-Jack!" He groaned, his hands getting tangled in the white locks as his body tried to register this new feeling.
Jack had barely started though. His tongue swirled and slid around the narrow shaft, easily covering the entire length as he bobbed up and down on the small thing. Hiccup writhed as this new onslaught of sensations made his whole body heat up. He closed his thighs tight on Jack's head as he felt an intense build-up in his gut. The fiery intensity exploded into a blazing inferno when one of Jack's fingers pressed against his hole and then, in a heated crescendo, that blaze reached a tipping point and he blew his light load into the older teen's mouth.
"God…" Hiccup breathed between deep gasps, his body going limp as he tried to recover from his second intense orgasm of the day.
"You enjoy that?" Jack asked after pulling off of Hiccup's glistening, flaccid member. He flopped down by the boy's side and slunk an arm around his shoulders and pulled him in close.
"Do you really need an answer?" Hiccup snarked, thinking his involuntary vocals would've more than broadcasted his feelings.
"No." Jack smirked. Then he leaned in and placed another fluttery kiss onto Hiccup's lips, filling his tummy mind with anticipation of what he would do with these men in the future.