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.
Pairings: Human-Toothless/slut?Hiccup
Warnings: Language, situations, and themes.

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.

Additional notes: Chapter does contain mild detailed M/F (Toothless/Stormfly).

Ugh, I feel like utter crap not updating in over a year. I'm gonna push to get this fic done for you all still sitting around. I swear it.

The party at Stormfly's was at full swing when Toothless stumbled in. He wasn't typically a drinker - unlike most of his peers, beer and the like had always been accessible since he was younger, all he had to do was ask - but it had been an early night for him. The second Hiccup had left his parents' home; he had taken his father's six pack to his room and attempted to drink himself to a stupor. Alcohol poisoning seemed the best way to go at the moment.

He wasn't ready to leave Berk. He didn't want to live with his grandparents while attending another school in vain hope to make it into a good university. Someone had stolen his sure placement, he just wasn't sure who. All cards went to Snotlout Jorgenson, the prick who could buy his way into anything.

Grabbing a silo cup from the expensive side table, Toothless drowned the amber liquid with a wince of burn as he made his way further into the throng of students. He was on a mission. Fuck all these tight asses flaunting what Daddy's Money could buy them. It wasn't as if he hadn't tried.

Stormfly was leaning against the wall, talking with Barf. Her slender finger was twisting a strand of dyed blue hair around as she giggled so prettily as he leaned into her, ready to press his mouth onto hers. Toothless strode forward and the girl twisted to face him, her face brightening. "Toothy! I justknew you'd come!" She grabbed his arm, a coy smile directed towards her male friend. "All 100 students attending Berk Academy are here! This is going to be so much fun!" She dragged him to grab another drink, this time straight from a bottle. Toothless appropriately nursed it. "What took you so long getting here?"

"Had another lay before," Toothless grunted, twirling the liquid in the bottle with rapt attention.

"You were getting laid?" Stormfly rushed out, eyes wide. "By who?" She took in the room. "I know you've been eyeing Astrid, but she's with Snotlout and then there's Ruffnut, but she's a bit kinky and..."

"Do you still want to fuck?" Toothless drained his beer. "If not, this is a bit of a waste."

Stormfly's expression faltered before an intrigued one took over. Releasing the strand of hair, she placed a dainty hand on his bicep. "Are you really not a virgin?"

"Let me put it this way, I've made my last partner," he leaned forward, pressing his mouth along the shell of her ear. Under his touch he could feel the shiver course through the girl's system as he continued breathlessly, "come untouched."

Her pupils were shot. "Show me."

Weeks later, sober, it wouldn't be his proudest moment. Sex, before the whole 'Toothless is a Virgin' thing, had always been a treasured item, ruined when he took a prostitute to fix a problem. There was no love in this act, only the need to prove to everyone that just because he didn't make it into their school, he was just as good, if not better. Snotlout could have his sports and friends, but he couldn't have that single moment as he took Stormfly to the back room.

It would be the talk of the party that Stormfly was screaming for more. He ate her out, letting her wiggle and moan under his skillful tongue, comparing those sounds to Hiccup's. Everything between the two was different, sight, sounds, and especially taste. Too tipsy to care at the moment, he went forward uncaring to the fact that he should be out with Hiccup. It should have been his prostitute under him, writhing on his covered cock as he plowed a slick hole. It should be narrow but long feet digging into his hips, drawing him closer. Last, it should be the husky voice still raspy from puberty begging him to fuck him.

"Oh, Gods, yes. Eh, eh, fuck, ah, so good."

It seemed so much better coming from Hiccup.

He held shaking hands under his own, keeping the girl from touching herself as he pushed himself forward into a rhythm. He could hear the voices beyond the door, Barf was angry that his girl was getting plowed but the loser. The smirk slid into place as he kept moving his hips. He had riled her up plenty earlier and he could feel the rapidly twitching grip around his cock with the needy whimpers leaving her lips. The tip of his penis slid outside and he rubbed up against the folds before sliding into the heat again, rubbing in just right. The same position he used with Hiccup that made the boy's toes curl and his breathing stop for a second.

"Toothless!" Stormfly tried ripping her hands away, her body pushing against his own. She shivered and shook, a breathless sob leaving her lips as she climaxed again around him, leaving a wet puddle under their bodies. Toothless slowed his thrusts to an almost agonizing pace, waited until the shaking stopped before he picked up speed again. This time she stole her hands out from under his grip, grabbing him around the neck to pull him down into a kiss, trying to hide another startled cry.

She would be talking about this fuck for weeks. Later, to all her friends, she would describe Toothless as the best lay she'd ever had in her young life. Snotlout had given her an orgasm when they fucked, but Toothless had given her multiples and still pushed on without an end in sight. His phone would blaze to life with the calls from the girls he had only dreamt of during Year One and Year Two.

They should never have dismissed him.

He turned her on her front, this way he could play with every nub. His fingers moved skillfully down her body, finding each ingenious zone until she was a puddle under him. With a clenched jaw he filled the condom and released his prey, letting the girl drop under him in her mess. She seemed so shell-shocked, he realized as he cleaned up in her private bathroom.

Grabbing his jeans with the full intent to grab another beer, maybe another quick screw, he frowned as he was stopped. "This has to happen again. Please."

Toothless smiled. "Can't say I can, Stormy." He pulled her bangs back, tilting her head to lay a kiss to her lips. "But I'll let you suck my cock anytime." He grabbed his shoes and left the room.

Snotlout was standing nonchalantly by the door, trying to pretend he wasn't listening in. There were hoots and hollering from his peers, cheering him along and 'damn, he fucked the shit out of that bitch!' He grabbed another bottle of beer and drained it, wiggling his brows toward Astrid and Ruffnut as if to tell them they had their chance.

By the time he left the party he had a several phone numbers from the guys and girls and more than a few drinks in his system. Trying to keep balance as he moved through the streets of Berk, he giggled and laughed as he almost stumbled over.

The Night Fury was located on Third and Main, a dim beacon this time of night, but a testament to home. He moved the opposite direction, towards the Pearly Gates. There, he snorted as he grabbed painted gold gates to stare into the spiraling roads of the rich and famous, laid Stoick Haddock, the man that fucked him over. The phone numbers in his pocket could have meant something if it hadn't been for this man.

He moved along the gates, checking the height of each length until he found the stone alcove of one of the lower mansions. Trekking up it while drunk was no easy feat. He saddled the ledge, raised his arms in excitement before tumbling over and into the Pearly Gates community with a startled shout. Luck would have it he landed in a rose bush, but it deterred him little as he moved through the fresh cut lawn of some high executive and into a lush land.

And into sheep.

Giggling as he folded his hands into the coarse coat of a ewe, he took in the sheer number of the creatures roaming the lands of the next executive.Mildew, he chuckled, taking in the big mansion on the coastal side. It was overpowering with the stench of success, the lands the housed sheep in city.

He remembered a joke once that Dr. Mildew liked to fuck sheep. The man was fixated on them, going so far as to include mathematical examples of the beasts in his final exams. Students in the economy department spoke of nightmares fixated around the creatures.

With sluggish movement he pushed and tugged the sheep towards the gate. The creature provided him a bored glance in front of the marble fence blocking them from the outside world. He groaned as he picked up the heavy sheep, urging it up onto the fencing with planning. Immediately the animal gave a startled cry as she fell onto the other side of the fence. Toothless giggled as he ran back to get another one.

"I, I got an invention," he slurred as he moved another sheep. This one didn't move as well as the other, trying to flee him quickly. "Catapult the sheep," he sung loudly. The thought of sheep flying made him laugh jovially. "Solve world insomnia, have to take me then!" He paused at the storage doors on the gate, confusion etching his face as he glanced between the doors and the tall wall he'd tossed one sheep over. Even in his drunken confusion it took seconds to break the padlock and even less to chase the dozen sheep from the pasture and into the open roads of the Pearly Gates. "Yah! Yah!" He ran after one, laughing as he bleated in fear.

His movements slowed as it crossed the winding road leading up to Stoick Haddocks multi-million dollar mansion. He was probably sleeping snug in his bed, not worried that he screwed up thousands of students' lives by letting in the select few that could give him staff perfect bribes. Shoulders tense, Toothless started towards the wide gates.

He'd just give that man a piece of his mind; let Stoick Haddock know exactly who he wrote off as unimportant.

Only halfway up the driveway he heard sirens. Everything in him went crazy, turning back towards the main gate where he saw the flashing blue lights starting up the hill and into the Pearly Gates. Somewhere under the shrill of sirens he heard the outraged cry of Mildew, "My sheep! Thief! Thief!" Somewhere else he heard the shouting of families being lulled awake by the bleats of sheep trampling through front yards.

Behind him the porch lights of Haddock Mansion came to light. Like a deer on death's door, Toothless froze and waited for the overpowering figure of Stoick to come down, to catch the local menace. He was going to go to jail and never go to college, his parents would be so disappointed and...

"Come on, we got to go!" Hiccup's voice hissed next to him. Firm hands grabbed his slack one, dragging the taller teen back to life. Both boys skirted into the grass, disappearing into the overgrowth off to the side of Haddock Mansion. "Follow me, I know a way out." Hiccup stumbled through the path, carefully avoiding the security lights strung across the property.

"H-Hiccup?" Toothless wheezed.

Annoyed green eyes flashed toward him. "Don't just stop, we have to go." Hiccup moved past a low hanging branch and into an area of heavy foliage. He stopped patiently as voices carried out around them about shadows being seen at the Haddock place. Come on." Hiccup raised some vines, baring open a hole in the concrete wall. "And stay close to the outer wall or they'll never find your body."

That...didn't sound good. Toothless wiggled past Hiccup, through the tight hole that came out onto step ground connecting to the secured forest he had lost his model plane in only two weeks before. Hiccup crawled past him, moving along the steep rock with practice ease. "If you stay a rock there, they'll find you. Mildew's hell bent to find the person that killed his prize sheep."

Killed? Toothless' stomach rolled as he grabbed a ledge.

"Toothless?"

"'On't feel good."

"Hey, what-Oh Gods!" Hiccup reeled back as the darker teen threw up over his shoes. "Ew! How much have you drunk?"

Pinching his fingers and swung forward, Toothless panted, "Just a little."

Scoffing, Hiccup hefted Toothless' arm over his shoulder, moving down the steep ravine. "Yeah, 'just a little'. Ugh, if I'd known you were going to do something stupid tonight, I should have just stayed with you."

"Oh man, how awesome would that be - we could both toss sheep. I'll lift you kept the thing steady." Toothless chuckled. He could have freed a lot more sheep if he'd had a hand and damn, with Hiccup he could have... done something to Stoick Haddock. He snickered at the thought of reprogramming the man's internal computers from the outside.

"Uh, no." Hiccup nearly slipped out from under him on the ledge, but regained his footing quickly. "We would have kept you out of trouble. Gods, your face stinks, what have you been doing."

"Fucking!" Toothless raised his arms. "Made it big!" He gives himself a congratulatory shout that is barely silenced by Hiccup's hand as they continue moving past some old caverns covered in the moss. Hiccup pauses on another spot for a second before continuing forward with more focus in his step to keep Toothless walking.

"So I'm not allowed to fuck around, but you can? You know what, you're a hypocrite. I should alert the cops that you're here." Hiccup almost let go of him, but Toothless (even drunk) is fast. Wrapping his arms around lithe shoulders, Toothless pressed his weight against the firm back, breathing in the familiar scent that is Hiccup. Hiccup still smells of water from the shower earlier.

"No, Baby, it's nothing like that. Didn't wanna do her, had to do here - prove a point. She got banged by a reject. An academy reject. Bet she's gonna be so embarrassed in a few weeks." He chuckles at the thought. "She never does anyone beneath her. Thought I was a student, hah. Bitch." Toothless rubbed his nose against the dip of Hiccup's back where there was an array of freckles. Strange, he realized as he licked (ignoring the annoyed groan from the brunette) the line leading from shoulder to shoulder. "Besides, wasn't you. You make good noises."

Exhaling, Hiccup continued walking, his shoulders dipped to carry some of Toothless' weight. "Let's get your ass home."

They took the bus from the wood line leading into the city, leaving the flashing lights leading up to the Pearly Gate Community. From the distance, Toothless saw Stormfly's party fading away into nothingness, all of the students having fled the scene when the flashing lights came by. "Sit down before you hurt yourself."

Dropping his hands from the rail, Toothless rolled across the back of the bus seats until he nestled against Hiccup's lap. "So happy my Hiccup was there," he nosed the teen's belly.

Pushing on the drunk's forehead, Hiccup grunted. "Damn straight you're lucky I was there. What kind of idiot plays pranks while drunk in the executive district? There are some of people you don't play pranks on and the President of Haddock Inc is one of those people." He crossed his arms across his chest.

Springing up, Toothless pulled himself across the bus seats as they bus entered the city, moving along the length of his street before pulling up a block from his parent's shop. Charging off the bus, he nearly tripped over his two big feet. As he laughed about his misfortunes, Hiccup spoke quietly with the bus driver before stepping closer, fingers tucked into his back pocket absently. "Let's get you home, Big Boy." Hiccup grabbed Toothless' arm, hefting it over his shoulder.

"That's an awesome idea!" Toothless nudged his foot over, nearly tripping the other boy. "I have a summer before I move in with my grandparents. Gotta get plenty in with the people I like."

"I'm not having sex with you, Toothless."

Scoffing, Toothless wiggled away, trying to move on his own. "Will if I paid you enough. Put together that toy you'd suck my cock. Hiccup's gonna suck my dick," he chortled out, dancing around a street light. Under him his left foot caught his right and he stumbled into the road.

"You couldn't pay me enough to sleep with you after tonight." Hiccup grabbed him again, shuffling again down the street. They had to take the stairs one by one, taking breaks as Toothless attempted regaining his balance over and over, claiming the ability to walk on his own. Hiccup scrapped his knuckles over the door, keeping Toothless away from the rail.

Spotting his father immediately, Toothless flailed his arms excited. "Dad, fuck, I got home and it was all-" He collapsed against his father's arm, pointing excitedly, "and I found Hiccup and he's gonna-"

"-Put him to bed, Mr. Fury." Hiccup chimed, pulling Toothless back up to his feet. "I apologize about waking you up, sir. I found him out in the suburbs releasing Mildew's sheep and about to go to m-" Hiccup paused, swallowing heavily, "Mr. Haddock's Mansion. Don't think he'd be in a good mood in the morning in jail with a hangover."

Blinking the tiredness from his eye, Mr. Fury helped gather Toothless onto unsteady feet. "Thank you for bringing him back home. He had been in his room, but..." he shook his head.

Between the two of them, they dragged and lured Toothless upstairs like a sheep ("Heh, sheep," Toothless chuckled too himself), dropping the drunk teen into bed. Shoes removed and tucked into his bed, Toothless reached for Hiccup, "Y, you promised."

"I promised nothing, go to sleep." Hiccup turned off the light, leaving the room.

In his drunken stupor, Toothless vaguely recalled hearing part of a conversation between his parents.

"-Mind if I call my dad...left my phone at home when I saw Toothless stumbling up the street...yeah, I live out in, um, the 'Gates. Dad must be out of his mind; last time cops were called I was in some trouble. Thanks much, sir. Yeah, I know he's a good boy usually, I can tell something's got him upset, just wish he'd tell me what before he did something stupid."

Rolled on his side, Toothless lost consciousness soon after.