“I can't believe you finally won an Oscar,” Harry whispered as his hands played with the buttons of an expensive silk dress shirt, removing it completely to tuck himself into the soft touchy feel of a robe, “It’s been, what, 84 years.” He giggled as soon as he recalled that old lady meme everyone had used for such extensive reasons.
Just then a broad male appeared through the door of their lavish bathrooms; some famous hotel the pair had stayed over for a couple days in order to be near the Oscar Awards location, of course.
Leonardo DiCaprio, a man that's known for the finest reasons, stood there with a small smirk, wrapped within a thick, rich, black robe and nothing else. He smiled as he approached Harry who wore a soft, pink, lacy robe, which was very soft in comparison to Leo’s. The Oscar was placed at the side right by their nightstand next to their shared bed all while Leo chuckled and wrapped his arms around Harry’s waist.
Harry sighed in content as he released all tension and allowed his body to melt into the warmth of the older man’s hold. His scent of thick cologne continued to linger his body, the smell that reminded them both of how Leonardo dressed for this glamorous night and won a damn Oscar finally.
“You know how much I hate that Internet meme,” Leo muttered as his hands gripped upon the thick weight of Harry’s hips, squeezing the skin with his hands that had the other squirm in delight, “Can't believe you hopped in on that stupid trend too.”
Harry only giggled once more, which was slightly strained as a shiver of pleasure rushed up his spine from the constant touches of the other’s hands all over his waist. The aura of the room dimmed into a deeper, sensual taste as both their shallow breaths were left to be heard. Harry’s eyes slipped shut as his lips were dropped to an awe as soon as he felt Leo’s lips pepper over his neck and down to the junction where shoulders and throat met. He pushed Harry’s excessively hair down to the side to reveal more skin, maybe slip a few fingers into the hem of the robe to tug it aside, but-
Harry burst out a dry chuckle as he pulled away from the man’s hold and spun around to have them chest to chest as his arms wrapped around Leo’s neck, “Someone’s a bit eager.” He whispered eyes flickered to Leo’s lips.
He shuddered as Leonardo gripped Harry’s sides tighter once more, “Well, after finally winning a fucking Oscar, of course, I’d be a little eager. Don’t you think I deserve something?” He teased.
Harry laughed and completely left Leonardo to himself, who stared back at him as though he were a rejected puppy, “That reminds me,” he walked over to the nightstand and picked up the Oscar award and gasped at the weight of it in its hand. He didn’t expect it to have any weight at all since Leo was able to just wave it around like a toy, “Oh shit.”
“What is it?” Leonardo asked as he moved his way back to Harry and wrapped his arm around his waist once more, his back tight against his chest.
“I didn’t expect it to be heavy-”
“It’s metal, Harry.” The man scoffed, “What did you expect-”
“Just metal?” Harry inquired, “You mean you were all meanie and puffy because you couldn’t get a metal stick? I thought it was gold plated or something! This seems pointless, pretty sure you could get one of these from Amazon Prime-” His words were immediately shut off, though, by a pair of warm lips pressed against his. The heat of both mouths emitting lust and need for each other. Leonardo pulled away after a couple seconds and glanced back down at a stunned, but reddened Harry who, “Was I rambling again?”
“Hell, you were,” Leonardo laughed as he plucked the Oscar away from Harry’s grabby hands, “Now, I am pretty sure that you can’t get one of those from Amazon Prime.”
“You sure, because I’ve seen some nice dildos that look just like that, pretty sure they got an Oscar on there somewhere-” Harry immediately shut his mouth as his cheeks went redder, “I-I mean, not that I looked for anything, but, fuck, yeah.”
“We’ve spent some good quality time with each other and you still blush over buying sex toys?” Leonardo asked, quite astonished if he were honest because Harry was far from decent, especially in bed, “You're too cute it's making me sick.”
Harry rolled his eyes, “Oh shut up, I swear you're more rugged than Louis’ been with me.”
“Well, I am Leonardo DiCaprio.” He laughed.
“Shut up.” Harry laughed, though, because yes he was, no, is Leonardo DiCaprio.
A man with honor, strong ego, incredible talent, amazing acting skills, no limits, like fuck there's literally no limit to what he is and there are definitely not enough words to describe how fucking amazing Leonardo is. Yes, he was a work of perfection from inside out, oh, but oh, what he really appreciated was that pulsating cock sitting underneath a thin layer of fabric. He was definitely gifted there, fucking blessed.
“Oh, baby.” Leonardo laughed, the shake of his hard chest startling Harry. He put up a hand to comb through Harry’s excessive amounts of hair, “You're just too cute, it's- I can't describe it and god the things you make me want to do-”
Harry huffed as he traced the man’s stubble with the edge of his index finger, “Then what're you waiting for- Christ!”
Harry yelped as the Oscar was tossed to the edge of the bed as his body was slammed right into the mess of white bed sheets, gasped out moans leaving his lips as Leonardo crawled over his body to straddle his thighs, grip tightly upon his frail wrists and tighten them up over his head.
“Leo- fuck-” Harry whimpered as the man remained silent, but was confident with his swift strides of sexual tension to kiss along his cheeks, down to his neck, and over the revealed skin of his chest as the pink robe began to loosen off his body from constant pulls and grips, “Oh my god-”
Leonardo made sure to make both of them comfortable, manhandling Harry’s body until he was perfectly laid across the bed in sweet proportion as his legs were split apart, captivating Leonardo between his soft, thighs, which were now revealed as his robe slipped down to reveal his legs completely, jumbled up at his upper thighs.
Harry continued to squirm, every single muscle in his body activated to feel the touches of the man he’s grown so fond of. His skin was laced with overlaps of goosebumps, begging to be pressed and pushed, skimmed over and kissed.
“Shhhh, baby, I've got you,” Leonardo whispered as his lips began to go south.
Harry only whimpered in response, legs automatically tightened around the man’s sides as he felt lips right over the soft skin of his toned stomach. Each kiss had him melt, gone weak where he panted. Blood rushes to his cheeks, his cock, and flushed over his body from feeling the pressures of those lips on such sensitive parts of his body. His back arched and mind screamed more, more, more all while Leonardo had his hands placed over his thick thighs, warning him that he was going down there.
Hands shot up to grip on dark blonde hair, hips forced to keep still and soon a long puddle of whimpers slipped from Harry’s lips, “Oh, oh Leonardo- fuck.” Harry could've just cried and his heart rate spiked as soon as he felt lips pressed against his hole, traced over with the tip of the tongue, “FUCK.”
“I'll get there, calm down.” Leonardo joked and Harry could feel the man’s smirk between his ass and God was this man even real?
Harry squirmed and his eyes darted to the back of his head, hips screaming. He felt lost within pleasure until his eyes were caught upon the Oscar Award that laid there untouched and boring just a few inches away. Leonardo continued to kiss along the junctions of thighs, slipping his tongue into him occasionally that had Harry break out a long, guttural moan.
Harry looked back at the award, though, then reached for it, smiling in content (well tried to since he kept panting out gasps from Leo’s amazing mouth) when his hands were wrapped around the item. He brought it close to his face, holding it with two hands as he admired the item. Harry interpreted the shape and size and wow the Oscar dude had some nice hair shaped into him. He was so intrigued by the thing, how the shape was mesmerizing that he hadn't noticed when Leonardo stopped eating him out and glanced back at him with confusion.
“Are- are you checking out the award while I'm going down on you?!” Leo asked, “Well there goes my self-respect.”
Harry glanced down to the man who put up a fake frown, as though he tried to really look hurt. Harry rolled his eyes and kicked at his shoulder, “Oi! Leave your acting for the movies.”
Leonardo grunted and slipped away from Harry’s thighs to move over Harry’s body and have their chests touch, their robes untied and revealing but not completely off their shoulders. Their hips and groins met, hard cocks pressed against one another that had Harry go weak.
“I-I’m just admiring it.” Harry shrugged, his tone soft from the recent pleasure he received.
“Admiring it?” Leonardo asked, “Thought you said it looked like one of those dildos from online?”
“Who said I don't admire dildos, gosh thought you knew me better,” Harry muttered, “Despicable.”
“Hm.” Leonardo glanced back at the award and a devious grin slipped over his lips, “Say.”
“Hm?” Harry asked.
“Do you reckon one of these things can be used as a dildo?” Leonardo casually asks as he took the award back from Harry’s hands and pretended to examine the item, “It’s long, obviously huge, and has a good grip.”
“Did all this acting get to your fucking head?!” Harry exclaimed, “You want to shove one of those things up your ass?”
“Oh shut up, you know I'm not into having anything near my area like that.” Leonardo quipped out.
“Who the fuck would actually who the fuck would ever do that?” Harry questioned.
Leonardo only stared at the man and smiled, “Pretty sure you know who I’m thinking about.”
“Who-” Harry’s eyes widened in shock, “You fucker I would never-”
“I am pretty sure you would.” Leonardo teased, “I mean, I could make it happen right now-”
“No.” Harry laughed, “Shut the fuck up-”
“Harry.” Leonardo drawled out, “It wouldn't hurt to try-”
“Wouldn't hurt to- what. This isn't like trying some new food off the menu, you twit. You're asking me to shove your fucking Oscar up my asshole.” Harry screeched out, “Wouldn't hurt. Bastard, that'll bloody tear my ass apart. Why would I want that?!”
Leonardo chuckled, “Well they did say we should keep our awards inside a special place-”
“Shut up.” Harry snapped jokingly, “Don't even start with any puns here.”
“Harry come on, I'll lube it up I mean it's not that big-”
“That fucking thing weighs as much as a newborn child!”
“Guess you'll get a taste of what pregnancy feels like-”
“Leo!” Harry shouted, “I’m fucking serious.”
“Baby,” Leonardo pressured as he placed the award down to cup the boy’s face and place a small kiss to his lips, begging to try something horrendous as this, “Let’s just try. If it’s too much we’ll stop, yeah?”
“You're fucking crazy-” Harry gasped out and cried out a whimper as he felt Leonardo’s lips press against his neck, an extra touch of his teeth scratched against his neck, “Bloody wanker, you're too persuasive.”
“Is that a yes?” Leonardo asked, excited.
“Better fucking get to it before I change my mind.”
“I can already feel my ass tearing.” Harry pushed out and his forehead was slick with a thin layer of sweat as Leonardo sat between his thighs and slicked up his beautiful award with excessive amounts of lube.
“Maybe you should've gotten this Oscar, you're overdramatic as fuck.” Leonardo laughed, “It didn't even touch you yet.”
“You're going to shove that thing up my ass how am I being over dramatic?!” Harry cried out.
“It’s just like any other toy, relax.” said Leo and sighed as he placed the lube aside and reached to stretch Harry’s legs apart even further, “I’ll start okay, nice and easy-”
“Fucking Christ, I am this close to bailing-”
“Sh, sh.” Leo whispered and held Harry’s ass cheek apart to reveal his hole that clenched around thin air, “I got you, baby.”
Harry whimpered in response to the pet name and shivered as he felt Leo pull against his robe to shed it off his shoulders and have him lay there, a naked beautiful mess. He placed the head of the Oscar against Harry’s hole while Harry laid there looking up at the ceiling, trying his best to stay calm and keep his breaths steady.
Harry had immediately shut his eyes as soon as he felt the head of the award breach into his intimate doors, perfectly led deep inside him.
“Ugh.” Harry groaned as soon as the head reached in and his eyes rolled to the back of his head as he felt the slick substance attribute to the stretch of his entrance, “Dear fucking god.”
He threw an arm over his face to cover the onslaught of blushes that flooded his face. However-
“Oh don't hide from me, Harry.” Leonardo clicked with the tip of his tongue and tugged the boy’s arm down, “Love to see how much this thing up your ass gets you riled up.”
“Jerk,” Harry grunted out, “You're so mean- fuck.” Harry arched his back as he felt a harsh push of the award into his ass that had him lurch up against the bed.
“But I’m your jerk.” Leonardo laughed.
“You're shoving a bloody award up ass and yet you're being sappy. What has acting done to you?!” Harry joked and yelled as he felt the shoulders of the Oscar taking its turn to breach into Harry.
“Oh, oh, oh god.” Harry panted now and literally sucked in heavy breaths. He felt his body shake in response to the award being placed in deeper, and God fuck the stretch was indescribable, “I swear if my ass tears-”
“You know that won't happen.” Leonardo grunted and his cock throbbed to the sight of Harry’s hold clenching and un-clenching around the award, the irregular shape obviously confusing the muscles as they tried to grip over the thing.
Harry was obviously starting to sweat now as the award was pushed deeper and Jesus was it a fucking stretch.
“Ah! Ah,” Harry cried out and thrashed against the bed, “T-The shoulders, the shoulders are- fuck-”
“Almost in-” Leonardo pressured the award harder now that had Harry throw his legs up and down in surprise, “T-There.”
The man remained concentrated as he pressed in and Harry gurgled within his moans as he cried, a sudden sting in his eyes as soon as he felt those shoulders slip in that almost had him scream. It had to be the widest and thickest part of the damn Oscar and Harry could hardly believe he agreed to this in the first fucking place.
“I got it in there-”
“Don't fucking stick it too far that it gets stuck or I swear to fucking god-”
“At least, you'll literally be an award for me-”
Harry groaned, “Bastard-”
“Kidding! Kidding.” Leonardo whispered and soon he began to move the award inside Harry, slightly jolting a twist to his wrist to turn the award that had the boy scream in response.
“Y-You can move it.” Harry choked.
“Y-You sure?” God, why is the room so fucking hot.
“Yeah, fuck, just pound my ass with it until I cry, Christ.” Harry rambled as much as he could, his mind automated to become distracted from the searing pain and pleasure mixed inside him.
“Alright, fuck, you have no fucking idea how hot you look-”
“An Oscar up my ass is hot, my god Leo, your sex life is astonishing.” Harry teased, “Ah!”
Leonardo smirked to the reaction he was able to extract from Harry’s lips, body, and fuck was he wrecked by all of this it almost had the man lose consciousness. His hand worked now, trying its best to pull the award in and out of Harry's asshole. However, it was an irregular shape, so he couldn't really go fast without the damn shoulders of the thing slamming and forcing Harry's walls apart the worst way possible. Instead, he sighed and pulled the award slowly in and out and allowed the robe to slip off his broad shoulders and puddle around his waist. Both bodies were naked now and he managed to press his chest onto Harry’s, tan an incredible contrast beside pale skin. Harry panted Leo, Leo, please endlessly as his hips stirred and heart quaked.
Of course, though, it's fucking weird to have an award shoved up his ass, but that slipped his mind as his lips were pleasured by the massage of another’s warm mouth. The sounds of slick lube and sucking kisses echoed throughout the room along with the little heavy pants that left Harry’s throat.
“Fuck, fuck, this shouldn't feel so fucking good.” Harry coughed out and his hands immediately wrapped around the other man’s back, blunt nails digging and scratching to encompass the pleasure he felt.
Leonardo grunted in response where their bodies danced against one another and lips touching too much skin as Leo thrust the award in harder, pressed harder that had Harry at a loss for words.
It was too much, too much and all Harry had left to say was a weak cry of Leonardo’s name as he came streams of come between the both of them, the mess a pretty mess that had given Leonardo another reason to smile that night.
“So good for me.” Leo whispered and kissed weak lips once again as Harry panted into his mouth, “So good.”