Saturday Night
By: Selim
Rating: M+
Summary: Toothless has a problem – a big one. About to enter his last year of school, it occurs to him he's the only virgin in his class. In hopes to rectify that, he stumbled upon a number for a prostitute. One night is never so easy.
Pairing: Human-Toothless/Slut?Hiccup
Warnings: Language, Minors having Sex, Protected Sex, Unprotected Sex, Toys, Rimming, Oral Sex, Deep Throating, Frottage.
Disclaimer: I do not own How to Train Your Dragon. This is a piece of fiction and the author is making no monetary gain off its creation.
Berk was a product of the industrial age. Up until Haddock Industries was founded, the island had been unhabituated save for the occasional scouting units by international militant groups during wars. Haddock Industries had started as a one-man shop, selling in commodities across the globe. It had grown over the first decade into a chain of offices across five different countries, the main one being back at Berk. With its design came the employees, working across the spectrum from accounting to zoology. There wasn't a thing in the known world that didn't have Haddock's hand in it.
As the business grew and people came to settle on the island, with it came other businesses. Not one to be put out by its own workers, Haddock Industries created competition that always had better revenue. Some businesses knew when to just give the company a large share in order to survive. Toothless' father had been one of the smarter small businesses, providing to the local schools a meal plan to receive quarterly profit margins.
Students that attended the Private School, making into Third Year, were always offered placement at the Private University on the island where they would receive tutelage in their designated field with a job lined up upon graduation. Students across the globe fought to get into the university because the persons future was golden.
Along the coast, nestled amongst the expensive condominiums and beach homes was Haddock Towers, a glass castle on the horizon. It was a motel that had started with twelve rooms, made to house visiting VIPs for Haddock Inc. As the years grew and the corporation became a power holder, it had also grown in size. Ten floors, including three presidential apartments, it was a gem.
Toothless had never been in the building himself. Having been born and raised in Berk, his family had a nice home above his father's restaurant. Some of the students at the local Academy had parties in the lower rooms during breaks, but this break the place was surprisingly empty as many students opted to leave the island for high-end vacations.
Stepping through the wide glass doors leading into an open floor, Toothless gazed up at the spiraling floors above him. It seemed endless, the amount of architecture placed into this one building. On his left, the concierge desk seemed hard at work just as the front reception bustled at their computers, talking with men wearing expensive suits.
Feeling out of place in his faded blue jeans and loose shirt Toothless shifted towards the shadows and the elevator, pleased that his prostitute had already secured a room. The price was starting to make sense, especially since the overall coverage didn't even pay for one night as this place.
The glass elevators came with a shutter, the wide doors sliding open to release an array of businessmen from various countries. Once empty, Toothless stepped in, hitting the second floor button with ease. His heart hammered as he watched the elevator rise, faster than he thought imaginable. It was only a second before the doors swung open again for the next floor and Toothless fought the urge to let the sliding doors close just to ride the elevator up to the top floor.
Room 227B.
Verifying the number on his cellphone and comparing directions with the plaque in front of the elevators, Toothless started left, his sharp eyes looking over the railing at the wide reception area below him. A limousine had pulled up in front of the doors for the businessmen and Toothless watched as they climbed in one after another. One day that'll be you in those suits. He smiled before disappearing behind the wall leading to the line of rooms.
The room in question was a double, both sides with a "Do Not Disturb" Sign in place. While building up the courage to come today, Toothless had pictured everything that could have gone wrong, from the pimp being in the room ready to mug him or there being the most unattractive, disease-ridden prostitute.
He still came though, with high hopes that there would be a babe on the other side. It's now or never.
With a deep breath, Toothless rapped his knuckles over the thick wood and stepped back. Inside he heard the slight scuffle of drawers being shut and the metal latch sliding open before the handle moved. The heavy oak pulled back an inside stood a decent sized young man, no older than fifteen. He had bright green eyes and the softest brown hair Toothless had ever seen.
"Um…" Toothless looked around. "Are you, um, the person I texted?"
"Looking for good time?" The boy tilted his head back, flashing pearly white teeth. Toothless nodded. "Good, come on in." The boy held the door open, giving the student room to come in. It wasn't lost on Toothless that the boy glanced around the hall before shutting the door, locking the chain once more. "Do you have the money?"
"Yeah." Toothless pulled out his wallet, taking out the folded bills with some despair. His bank account was certainly smaller now, but he kept reminding himself it was going to a good cause. He handed the cash over and watched as the prostitute counted the bills before dipping the money into his back pocket. He shifted nervously. "Look, I've, uh, never done this before."
"Got a whore?" The brunette inquired, unbuttoning his tight white shirt. Under, Toothless noted, was a tight band tee.
Face burning, Toothless nodded.
The boy pierced his lips, staring blankly at the wall. "It's easy. I'm yours until noon tomorrow. Pretty good bargain at that price, don't you think? No scarring, no scat – take a piss on me and I'll kill you. Follow those rules and we should be cool." He licked his dry lips before turning to Toothless again. "You can call me Hiccup. I hope you weren't expecting a woman."
"Um, Toothless." The student rubbed his head, unsure if the name he was given had been a codename. Berk-ian names were always so confusion. "And I'm cool, either way."
He nearly jumped out of his skin as Hiccup fell to his knees in front of him. The boy – Hiccup – was staring up at him with half lidded eyes, plagued with some annoyances. "Good, there were no refunds." His deft fingers pulled at Toothless' fly, unzipping it with haste. The dark haired teen nearly jumped from his skin as the cold hands wrapped around his soft – but definitely hardening – cock, pulling it free from his briefs and through the slit in his pants. Oh gods, this is really happening.
Slumping against the nearest wall, Toothless let his hands fall back to avoid grabbing Hiccup's face and just getting him started. It seemed he wasn't the only one with some reservation about this meeting. For all his going nature, Hiccup appeared conflicted with where to go next, the paid of his thumb brushing the underside of Toothless' cock as his pink tongue stuck between his lips in thought. Finally after some conflict, Hiccup leaned forward and curled his tongue around the dark tip.
Toothless tilted his head back, exhaling heavily as a sharp twinge flooded his body. The next lick moved from the vein under his cock back towards the tip before he was enveloped in the warm heat of Hiccup's mouth. The boy's hands moved down, through the zipper of his pants, to grasps his balls, hanging heavily between his thighs. Eyes closed, Hiccup's face was moving closer to Toothless' body, taking in more and more of his cock. The slither of the tongue against the underside of his penis was indescribable. His own hand was nothing in comparison to the mouth, especially as the tip brushed against the back of Hiccup's throat.
Spongy was his first thought, Fuck yeah his second.
His fist tightened, uncertainty crossing his mind. The need to lace his fingers in that smooth hair, to push his dick in further, was unbearable. If a mouth feels like this, just imagine being balls deep. He groaned as Hiccup pulled back the smallest of moans. The warm breath flooding from his nose made Toothless shutter. Opening his eyes, he watched as Hiccup rolled forward again on the balls of his feet, swallowing Toothless down again. "Shit!" He felt his hips jerk forward. The throat around his tip tightened before Hiccup pulled back, coughing. "S, sorry…"
"Didn't get you, did I?" Hiccup asked, rubbing his jaw.
"No. Sorry, didn't mean to..."
"It's all right. Fuck my mouth." Hiccup's lips curled up. His hands left Toothless' jeans, grasping at Toothless' bigger ones, rougher ones, bringing them forward to rest on his jaw. Brushing his hands over Hiccup's low cheek bone, Toothless leaned forward, nearly arching over Hiccup as he pushed his hips past the plane of puffy lips. Hiccup's tongue rubbed against the underside of his cock again as he pushed against the back of the throat. As he touched the spongy part, he pulled back again, trying to tilt Hiccup's face just right. "You look good like this."
Hiccup's eyes sparkled, begging him to do it.
He pushed forward, easing his hips again into the spot He watched as Hiccup's cheeks hollowed out around him, creating a vacuum. Perfect didn't even cover the feeling he was having. In and out, he thrusts became greedy as he listened to the noises he was forcing from Hiccup. Gug, gug, gug. Hiccup had shifted himself around just right so he was on all four, his mouth parted and ready as Toothless kept him in place. Green eyes were dark with lust, staring up and watching Toothless.
"Shit… shit…" His orgasm was building. His balls were drawing in, belly coiling with each slap. He pulled back, fisting his shaft. The first line spilt against Hiccup's tongue and down his chin the second one creating a line over his nose as Toothless pulled the orgasm. Slumping back against the wall, Toothless watched as Hiccup pulled back, sliding his fingers down his face and through the mess.
And his lap… Toothless took a glance towards the tight designer jeans Hiccup was wearing, proudly defining his own erection. Taking even breaths, the student returned the smile. "I want you on the bed."
Hiccup stood on his knees, taking a cautious step towards the double bed. He leaned forward on the firm mattress, pressing his still-clothed ass out, accentuating his better features. Grinning, Toothless started forward. His open palm slapped Hiccup's back side causing the boy to shout before they slid down to the folds off his ass, grabbing. Leaning his mouth forward, Toothless licked the bare skin along Hiccup's collarbone where it disappeared under the tight black shirt. "Always was an ass man."
"No scars," Hiccup reminded him as his teeth grazed over the skin.
Pulling his mouth back, Toothless pressed the line of his body against Hiccup. Hands moving, he grasped at the button, freeing it and unzipping the tight pants from tiny hips. As if to help, Hiccup worked them hem line down. Counterintuitive to the process, he rolled his hips back. Toothless groaned, pulling his hips back and watched as the jeans slid down until Hiccup could toe them off. Grabbing his own hemline, Toothless discarded his pants, kicking them off towards the corner of the room with his underwear. Next, he pulled his shirt over his shoulders before letting it join his other clothes.
In an equal state of undress, Hiccup raised a knee onto the bed, sending a cool look over his shoulder. "Condoms," he purred, "Are in the side drawer."
"Don't need it yet." Toothless bent down, spreading Hiccup's white globes apart. There, deep in the middle was the boy's pink entrance, winking at him, offering so much on the other end. Just south, nestled between skinny thighs were the boy's testes, proportional to his size, and leading up to a small fat penis. Toothless ran his fingers down the line, from tailbone to perineum. No hair, he noted absently. A very well-maintained prostitute.
He had watched porn in preparation of tonight, not wanting to come in a complete and utter virgin. There was something about being humiliated for his experience he didn't want to relieve, especially when the mockery came from someone he was paying to help alleviate the situation. Hiccup had been good humored about the whole thing, offering the patience and goodwill, apparently used to the greediness of the client.
"You look so good," Whispered Toothless, purposely breathing against the pink orifice. Hiccup moaned, shifting again. His leg, settled net to Toothless' shoulder, stretched out to provide better view. Cupping his hands against the boy's globes, he spread the skin apart and curled his tongue against the rippled edges of the anus. It didn't taste like anything, he noted absently. Hiccup had certainly cleaned up well in preparation, but it was to be expected. He hadn't known if Hiccup was going to be a male or female and Hiccup certainly didn't know Toothless' sex prior to opening that door. He prepared for anything.
He kissed the skin next before bringing his tongue once more over the skin, pressing against the tight muscles blocking his path. Hiccup made a low, muffled sound as his hips shifted back again. Unabated, Toothless brought his thumb against the pink rim, pulling the taut skin back as his tongue once more slid against the velvety edges, the bright pink pulled white before disappearing into darkness. Nosing forward, the dark haired teen wedged his hands in the pull Hiccup's anus open until his tongue slipped firmly between the tight muscles. Saliva slipped from the corner of his mouth as he moved, licking the velvet deepness, enjoying the spicy scent of Hiccup's body wash.
He really was an ass man. Women's asses, men's asses. His screening of porn videos always included this and he had wanted to put his nose between those milky legs on the laptop screen. He wanted to bathe the back entrance with his own saliva and drive those mews forward
As his tongue stretched further in, he scrapped his front two teeth over the rolled up rim. Hiccup gave a startled his second leg sliding back to the ground as his hips shifted back, trying to push Toothless further in. Put his hands on Hiccup's hips, Toothless rolled his tongue out and down against Hiccup's perineum, collecting salty sweat before he moved once more up to the puffy, wet entrance. This time, his tongue was gobbled up greedily. Rolling his tongue, Toothless pulled out before sliding in again, an approving noise escaping his lips as Hiccup clenched his anus muscles.
The thin hips were rolling against the mattress under his palm, dry humping in desperate need. Hiccup's small voice, panting against satin fabric, begged hoarsely, "Please, I need you in me…"
"Let me get the condom." Toothless purposely stood and arched himself over Hiccup, letting his returned erection rub against the cleft of the boy's ass as he reached for the nightstand. True to his word, a box of condoms was in the drawer with a bottle of untouched lube. Forgoing the lube – he wasn't going to need to help masturbate now – Toothless tore open the box and ripped open one of the small aluminum packaging. It fit snug around him, leaving a wet mess on his hand as he unrolled it around his stiff cock.
This was it, Toothless rubbed the slick tip of his cock between the moist folds of Hiccup's bottom. Hiccup was watching him over his shoulder, eyes dark and bloodshot. He made someone need him – even though paid. Hiccup could have just rolled over and taken it, but that (Toothless was sure of it) was the face of a person who not only wanted, but needed Toothless to bring them off. Grabbing the base of his cock, he pushed forward, past the loosened ring of muscles.
Under him, Hiccup hissed. His grip on the bed spread tightened. Toothless placed his heavy hands on the boy's hips, stopping Hiccup from pulling away. Pushing a little further in, he groaned at the tightness around his dick. This, he realized, was far better than the other teen's throat had ever been. No wonder everyone at school is doing it.
He couldn't wait. He bucked his hips forward and pushed the rest of his dick deep inside. Hiccup gave a startled cry, pulling on the blankets. Waiting, the older boy rubbed the bruises already forming on Hiccup's hips, waiting for the boy's breathing to thin out and the obvious pain to go away.
"P, please…" Hiccup whispered, pushing himself on his knees, "Please move."
Nodding, Toothless pulled his cock out until only the head remained pierced inside. Moving his leg around to better angle himself, he pushed forward once more until he was once more balls deep again. Hiccup groaned. Pulling the boy's hips back, Toothless tried again. In, out. Slowly a rhythm built up, the slapping of skin filling the room. It still didn't compare to the porn, Toothless realized as he pulled again, the orgasm building inside him.
He should be begging for my cock. Why isn't he?
Hiccup's head was ducked down, his breathing labored. Between his legs, his erection bobbed back and forth Toothless shifted his hips, trying for a different angle. Pushing his hips forward again, he heard a startled gasp from Hiccup. He pushed again into that very spot, pleased when Hiccup pushed back against him. Body rocking, Hiccup moaned and cried with each thrust. Tightening his grip on Hiccup's hips, the older teen dripped into that spot, relishing in the sounds of Hiccup's moans.
"More, fuck, oh gods…" One of Hiccup's hands moved, wrapping around his balls, attempting to ward off his own orgasm. Grabbing that hand, Toothless pressed it back against the bed moving his weight to push Hiccup down. His other hand moved to grab the brunette's free one, pressing both smooth, pale hands to the bed.
His hips worked fast, slamming into that very spot. His balls kept slapping against the warm flesh of his partner, loud to his ear. He wasn't going to last long, but it didn't seem right to come before his prostitute. "You feel so tight…" Hiccup did. Each thrust seemed to be wrapped in the warmest of gloves that convulsed around with a grip. It was becoming too much for him. His thrusts, once even, were erratic and sharp against that spot.
Head turned, Hiccup wiggled and cried, mouth parted and droll spilling on the comforter. "Oh gods, please…need to…oh fuck…so good…ah! Ah!" He back arched and buttocks tightened as he spilled between them.
The grip around his dick grew even hotter. Toothless tossed his head back as he spilt inside the condom, finally. He stayed still for a few seconds, a few tentative thrusts still in him, trying to imagine what he would have been like to be inside that tight spot surrounded not by latex, but by his own warm seed. Finally, he pulled free and pulled the condom off, tossing it in the waste basket found between the beds.
Sitting up, Toothless took in the mess of a prostitute he'd left under him. Hiccup, eyes closed and breathing heavy, was blanketed in a thin layer of sweat. His hips were red, forming black along the center where his hands hand tightened. There was scratching along the folds of his buttocks where Toothless had pulled the mounds apart and between them, puffy and red and slick with lube from the condom was Hiccup's anus, almost ready for another go.
Dipping his fingers in, Toothless felt a wave of joy go through him as Hiccup's back entrance swallowed his finger with no resistance. Face pressed against the blanket, Hiccup groaned. "I have you until noon."
Hiccup rolled his head to the side. "Mm. I have us on reserve for food as well."
"We'll have to see if we have time to eat." Toothless smirked, curling his fingers against a velvety spot that made Hiccup moan. "There's so much to do and I only have so much time to do it."