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Snakes and Ladders (A Hollywood SI/OC)

Hollywood, the land of dreams, the birthplace of modern cinema, the-. ah, who am I kidding, it's just a big old game of snakes and ladders. You either go up or down, depending on whether you got a ladder, or a snake in your corner. But what happens if you just, flip the board over? Let's see what happens when Richmond 'Ricky' Stirling attempts to do precisely that. Why wouldn't he? When life is just a game for him. Don't forget to add this to your collections for daily updates, and leave a 5 star review will you? It'll be much appreciated. Do share your honest feedback though. As an author, I strive to improve myself and I can't do that without my dear readers' varied opinions. Also, don't forget to join my discord server: https://disc ord.gg/uh2fS Guatb P.S, here is my p.a.t.r.e.o.n account for additional chapters: https://www.patr eon.com/user?u=42 576719 (remove the spaces after copy pasting the link) or just search 'Archonstine' on patreon... whichever works

Archonstine · Films
Pas assez d’évaluations
69 Chs

The Aviator

Author's note: I now have a p-word as you all know, so if you feel like reading 5 advanced chapters at the measly price of $3, then do join. The link is in this book's bio, or you can just search 'Archonstine' followed by p-word on your browser.

Also, join my discord will ya? For movie and tv-show recommendations and character images. And also it's the one place where I ask you all for suggestions. The link is in this book's bio.

P.S, donate some power stones while you're at it. And maybe... write up a review?

 

6th July 1997 (Saturday)

Ricky Stirling (POV)

I pulled up to the building's entrance at 5:45, parking my car near the sidewalk and putting on rock music on my Walkman.

I kill the engine and sit patiently, fighting off the temptation to needlessly glance at my wristwatch, as I eagerly await the reason for this expedition. You see, Charlize hadn't had any particularly high paying roles yet, and her most famous appearance had garnered a Best Supporting Actress nomination in Golden Globes, thereby serving as her big break. But it was a low-budget independent production, had just about crossed its production budget in gross, and an art-house film at its core.

So no big paycheck.

No big paycheck, equals limited funds, and even coupled with her modeling gigs, she had nowhere near enough saved up to buy a house for herself.

And that I suppose is the reason why I am stewing in my car outside a high-end motel of all places.

I tap the steering wheel rhythmically for the next 5 minutes, bobbing my head to Led Zeppelin, who thankfully exist here, and have released several classics of theirs.

Several, not all. Apparently in this demented timeline, after releasing their legendary 4th album, they… kinda died.

Honestly it didn't shock me that much, considering the fates of several famous personalities are significantly different here, with quite a few of them not even existing.

What did shock me however was the cause of their death… their plane crashed.

Yep, their private plane, the infamous 'Starship', a Boeing 720, experienced a heavy bird strike, and they exploded miles away from the California coastline, in a massive explosion.

In fact, a vagabond photographer who was out and about that night, was somehow lucky enough to perfectly capture the moment in a photo, which he sold for several thousands, and made him an overnight celebrity. He even launched his own photography studio 4 years later to immense success, and married a Scandinavian model, after amassing a net worth in several millions.

Reading about his story in his biography was not only all kinds of shocking, but rather darkly amusing. I mean, the fact that the death of a few people somehow facilitated the success of others, simply due to the enormous spectacle their demise turned out to be… unbelievable.

Just as I was about to sink into my retrospective thoughts, I heard a tap from my right.

It was Charlize, knocking on my car's side glass, and pointing down towards the… the handle.

I swiftly unlocked the door, and took the moment to stuff my Walkman and headphones in the glove compartment… After all, I'll have no need of them, I'm certain my hands will be full, and my mind thoroughly engaged, as I embark on this evening of romance with my date, who looked mesmerizing.

I could be biased, considering I know exactly how well she'll end up looking over the years, but even now, few could even hope to compete with her ethereal allure.

Uma Thurman comes to mind…

No! Bad Ricky!

As I chastise myself for my perverted line of thinking, I hear, "What'cha thinking?" in a teasing tone.

Without missing a beat I reply, "How stunning you look this fine evening, ma Cherie!" I flash a charming smile, as I run my eyes across her body.

"Thank you… What does 'ma sherry' mean- oh don't you dare laugh at me Poly!" She exclaimed, when I let out a light snort at her 'cute' question.

"It means darling in French." I nevertheless answer with a cheeky grin.

"Calling me Darling before we've even set out-" She slowly claps her hands sarcastically, "you certainly are bold for one. Well then, you're the one who insisted on this so tell me, what's the plan?"

I turn the key in the ignition, and my Nissan R390 whirs into life.

Yep.

I got a sports car.

Just the other day actually, and oh boy, was it one of a kind.

A Nissan R390 GT1, a racecar that won at Le Mans this year and is set to race next year as well. Apparently they detuned a model and modified it for road use, and according to their claims, it can reportedly reach a top speed of 220 mph.

And since it was a modified version, and had to be pre-ordered with specifications, it cost me a nice and hefty sum of a million dollars.

Yeah… you heard that right.

A million fucking dollars… for a depreciating asset.

From a financial standpoint, the deal sucks ass… but who the fuck cares?!

Not me!

Even after making strategic investments in real estate, bonds, and hedge funds, I've still got excess of $10 million just sitting in a bank, losing its value in spite of the interest rate offered.

Inflation truly is a bitch.

"The plan… is exactly what we discussed yesterday. Dinner, and then a tour of Tinseltown."

"... Ok, spill. What's the REAL plan?"

"I just told you. Dinner and then a tour of Hollywood… and my amazing company of course. Don't tell me that's not enough for you?"

She gave me a flat look, before turning her head back, "... I'm not going to bother thinking up a response to that."

Have it your way!" I chuckled before stepping on the gas.

"So… dinner. Where exactly?"

"Oh, just this little place on Hollywood Boulevard. I go there all the time really, twice a week minimum. We have a reservation for 6:30, so- get ready for a long drive."

"Huh. Hollywood Boulevard… What's the name of the restaurant?"

"It's just a really old steakhouse-"

"Musso and Frank Grill?"

Oh… she knows. Did not expect that.

A little disappointed at having my surprise ruined, I reply in a slightly disgruntled manner, "Congratulations! You want a trophy or something? Oh wait, you're a consummate professional. How about an Oscar replica?"

She didn't reply with a quip, like she normally does. A quick glance at her pretty face told me exactly what her worries were.

"Oh, loosen up a little will you?! I asked you out, so naturally I'm paying-"

"No! We'll split the bill." She shot back stubbornly.

"... My dear atomic blonde," I begin, "I sincerely doubt you have enough cash to foot even half of the bill we'll rack up. No-no, don't look at me like that, you know it's not a dig at your situation. You think I'm that superficial? Just relax ma Cherie, and enjoy! That's all I ask. I'm the one who planned and set it all up, so naturally it's my responsibility to see it through."

Huh, it seems my words finally soothed her ruffled feathers, as her expression softened.

"Hold on… what do you mean, planned and set it all up? It's a reservation, all it requires is a single phone call I bet for someone like you… Aha! I knew it! You do have something planned after dinner!" She exclaims in triumph, finally disregarding the awkwardness from before.

On the other hand, bloody hell. I spoke too fucking much.

"-Like I keep telling you, we'll take a tour of the city of angels."

"You know? Normally, I would believe you and leave it at that. But that self-satisfied grin on your stupid mug whenever you bring it up, tells me it's gonna be unnecessarily grandiose or somethin'. Now am I right?"

"... Let's just say, we'll be taking the scenic route… and leave it at that. You're not getting another word out of me on that."

"... Fine."

And with that, we settled into a comfortable silence for the next few minutes, occasionally making small talk but mostly, she was content in looking out the window and enjoying the view as we sped through the dusky streets of L.A… until-

"WHAT THE-" I slide the window down before pushing my head out and yelling with fury, "GO BACK TO DRIVING SCHOOL YOU IMPOTENT FUCK-"

"SHUT THE FUCK UP, YOU PEDANTIC ASSHOLE, YOU WANT ME TO COME OUT AND FLOOR YOUR ASS?"

The nerve of this reckless motherfucka! Breaking a red light and almost crashing into my million dollar car?!

Just as I was about to reply-

"Oh PLEASE! THERE'S 2 OF US AND 1 OF YOU!! WE'LL KICK THE LIVING CRAP OUT OF YOU 9 WAYS TO SUNDAY IF YOU STEP OUT THE TIN-CAN YOU CALL A FUCKIN' CAR!" Charlize joined in.

She stuck her head out as well, yelling all kinds of expletives, making gestures with her middle finger that no graceful lady should ever have known, let alone subject others to them… I think I'm in love.

A few seconds later, the man just drove past us, keeping his head down with a sheepish expression, clearly not willing to tango with my kickass date for the evening.

Even after he left, and I started driving, it seems her temper had not simmered down a lot.

"I swear to God, the nerve of some people here! Almost barreling straight into me-"

"Ma Cherie… that was the greatest thing I've ever seen. No, I'm serious! The way you just started going at him, like firing bullets from an assault rifle, it was quite literally the most amazing thing I've ever witnessed on a date-"

"Oh stop! Stop teasing me-"

"That's the crazy thing, I'm not! Teasing you I mean, let me repeat. That was the greatest thing I've ever seen on a date. Period."

Oh, the blush that overcame her face that very instant… in the words of the immortal God of sarcasm… Could she BE any hotter?

We walked towards the door at a sedate pace, arm in arm, as we bonded in our mutual hatred for drunk drivers.

Well… he wasn't drunk, not really. But she didn't know that, she just assumed and started raging at his very memory.

And I was too busy agreeing with her, throwing my own 2 cents in every now and then, to actually correct her.

The doorman opened with a welcoming smile.

"Mr. Stirling! A pleasure to have you with us this fine evening! Please, this way. Your table is ready."

"Thanks Cliff! How's the kid by the way? You give him a name yet?"

"Yes actually! He's now officially Greg Keitel. We named him after my wife's uncle Greg, who passed away last year."

"Oh, that's wonderful! Not the passing away bit, that's tragic and you have my condolences. Greg is a great name though!"

"Honestly- I wanted him to be Harvey, you know after Harvey Keitel and all but-" He leaned in a bit to whisper, "My wife was in labor for 16 hours and his head was the size of a cantaloupe… I wasn't about to argue with her any time soon."

"... You're a wise man Cliff. Anyways, thanks for escorting us, and oh! Do forgive me for my manners! Let me introduce you to the lovely Charlize Theron!"

"A pleasure Ma'am, hope you enjoy your dinner." He took a low bow, before departing to cater to others.

Charlize just looks around the room, awestruck as she recognizes a few faces around us.

"Ok- I know this place serves the Hollywood elite, bu-but this?! A separate room? And the people here- oh my gosh Ricky look! That's Joanne Harlow!" She nearly squeaks out.

"Ah! Aunt Joan! Haven't seen her in months now… are you a fan?" I ask, as we take our seats.

Her gaze doesn't shift away from 'Joan' though.

"A fan?! She's my inspiration! She's the reason I took up modeling in New Yo-. Hold the fuck on… did you just call her, Joanne Harlow, one of the biggest supermodels of the 70s, Aunt?!"

I nod casually, maintaining a calm composure outwards as I start perusing the menu. "Yep. It's what she told me to call her a decade ago… when she was spending a few nights here and there at my home." I clam up, for no other reason than to mess with her.

"Well?!" She asked, finally having lost her patience as her almond shaped blue eyes kept darting over to my dear 'Aunt's' table.

"Well what?"

"Ricky I swear to God-"

"Okay, okay! Relax, just look at the menu and decide what you want to order. I'll tell you the story once the food comes, we've got all night after all!"

"... Fine. Just one thing. I don't know what's good here, my first time and all. So, lobster. They can't go wrong with that I suppose."

"Excuse me?!" I ask, scandalized, "This is Musso and Frank! Nothing ever goes wrong here. But yeah, you're not wrong. Their baked stuffed lobster is pretty good."

"What about Lobster Thermidor? They have that right?"

"... They do, but only on Thursdays. You're out of luck I suppose… Unless you want to come here next Thursday as well? I'm sure that can be arranged, my schedule is wide open-"

"No!"

Huh… the instant rejection, followed by slight panic-

"I-I'm busy next week and-" She fumbles, desperately trying to think of an excuse.

"I'm kidding! I'm kidding ma Cherie, next week's been booked to hell and back for me. Next month actually, cause now all the remaining scenes left are mine. Also, relax will you? If you're not comfortable, just tell me! Don't feel obliged to accept, or even think up an excuse or something! Your frankness is actually an excellent change of pace for me, and just one of the many things that made me ask you out!"

Aha!

STRIKE!

The dumbstruck expression on her face indicates I subverted her expectations in all the right ways!

That's a point in my favor I suppose!

After some chit-chatting here and there, the wine finally arrived.

"From our collection of Pinot Noir, Old World, a 1985 Camille Giraud, from Cote De Beaune." The server opened the bottle before proceeding to pour it into our glasses. "Enjoy, Sir. And Madame." Before swiftly exiting.

We pick up our glasses, "Cheers." before I take a sip-

Oh hell no!

"Wait! Do-don't just gulp it all down! It's a premium 1985 reserve! For the sake of your god, sip it! How else will you taste it!" I cry out at the blasphemy I was witnessing in broad daylight… I mean, enclosed moonlight.

"Sorry? I promise I'll sip the next glass, it's just that- I think I saw Harlow looking at me, and it felt like she judging me or something-"

"That's because she was judging you."

Her eyes widened as if she had just received some devastating news… which I suppose, she had, if taken in the wrong context.

And so I quickly clarify, "She was judging you, for being on a date with me. She's wondering what might have compelled you to sacrifice an evening of your life to the devil in disguise, aka me."

"What?! Ricky, I thought you called her Aunt! Aunt Joan?! Why would she- just what?"

With a sigh, I take another sip of my beautiful red wine, before launching into an explanation. "The food isn't here yet, but I might as well spill the story. So here goes… once upon a time… my dad seduced her. And she kept getting seduced. I had to muffle my ears with a pillow for days, to even get a wink of sleep. And every morning after, she would join us for breakfast, and talk down at me patronizingly, calling me chubby little Ricky, as I just sat there, eating my eggs, taking one for the world. I was sick of it. Plus, her eyes always told a different story. She had fallen in love with my dad, and wanted to marry him… but he didn't want that. For him, she was just a fling, a way to scratch the itch so as to say."

I take a pause, as the food finally arrives, two plates of crab cakes, along with a filet mignon, a baked stuffed lobster, and a Caesar salad.

She continues looking at me with rapt attention, clearly eager to find out what happened next.

So I graciously obliged, "Long story short, he told her no, and she thought I was the obstacle. She never liked me since then. Also… there was an incident that occurred a few years ago… it caused quite the little kerfuffle."

"What incident?"

"These crab cakes are delicious! Here, you should try one-"

"What. Incident."

"... Okay so. My dad was taking her out to this fancy ass dinner one day. The thing is, he had promised to watch the game with me that same night. We were at an impasse, when I might have said…"

"Said what?"

"You have to understand Charlize, I didn't realize she had arrived and was right outside the door, so it slipped out-"

"Said what?"

With a heavy sigh, I dispense the line, "I said and I quote, 'Come on dad! Bros before Hoes!' And then the door opened." I held my face with my hands, as Charlize broke out into enchanting peals of laughter, not even caring about the fact, that I had called her 'inspiration' a whore.

"Oh! My God was that hilarious!" She squealed, still busy laughing at my expense.

… For some reason, it didn't bother me at all. The sound of her laughter was practically music to my ears.

"Oh I just realized! Your father must have spanked you silly!" She gasped, clearly enjoying the mental image she had conjured up on assumptions.

"No actually. He just looked amused, and ruffled my hair a little, before departing. I suppose the lack of scolding, or not defending her, alienated her even more to me. A month later, they broke up."

"But, he didn't punish you or anything? Or even scold you a little? You did call his girlfriend a… whore to her face. In South Africa, you would've been slapped silly." She deadpanned.

"Well, this is U, S, motherfuckin' A. The land of freedom and liberty… My dad didn't punish me, he just told Wyatt to take care of that on his behalf." I switched tracks midway, eliciting another guffaw, as I continued in a self-deprecating tone.

"Wyatt, the butler. The disciplinarian in my life, who would never hesitate to set me straight if I fucked up… For that remark? He made me clean the backyard, do the dishes, and when I quipped about him being too lazy to do his job… wipe the floor of all rooms… It took me hours, BUT! I endured. And I came out stronger than bef- Oh come on!" I give up, as her laughter resurges in full force, her eyes mocking me every second.

Setting a humorous tone for the dinner, we continued chit-chatting for nearly an hour, as I shared one crazy story after another, ensuring not a second goes by where she experiences even a smidgen of boredom.

It also had some fringe benefits by the way. Apparently recalling humorous stories from my past and narrating them in an exaggerated manner was a skill in and of itself.

PING!

Anecdotal Comedy skill has leveled up!

Anecdotal Comedy Lvl 31

The gamer just straight up rules.

"Well… I don't know about you, but the night is still young, and I did promise you a tour of LA."

"Yeah, what's that about? It's been 2 hours, and I still don't know what the hell you've planned?! Rickyyy! Tell me, won't you?" She asked in a husky tone, batting her eyelashes flirtatiously, as pouted a little.

Minx.

"I have told you 8 times, so let this be the 9th and final time, it's meant to be a surprise! So co-operate a little okay? I guarantee you'll have fun."

"... Fine."

"Thank you. Now back to the car. The tour of this city will start from a certain destination, and we need to get there by 8:30 latest." And just then, the valet arrives with my baby-

"What's the destination?"

I glare at her semi-seriously, causing her to finally stop nagging the living hell out of me.

We get in the car, and I promptly open the glove compartment, pulling out a black blindfold and flinging it lightly at her lap. "Put it on, and don't you dare sneak a peek. Trust me, I'll know if you do it."

She looks at the blindfold with hesitation, prompting to reassure her a little, "Do you trust me?"

"What?"

"Do you trust me?"

"... Yes."

"Put it on. I promise it'll be for a half an hour max. We'll arrive by then. I just want to see the expression on your face when you realize what I've got in store for the night." I smirk.

"How long now, Poly?"

"Not that long, 'my sherry'."

"Stop it! Don't call me that!"

"What? Sherry? Nope, you're stuck with that one. It's your fault for not knowing French."

"Well I'm sorry! But we can't all be geniuses Poly!"

"Seriously, how many languages are you fluent in again?"

"Lost count."

"No you didn't! You never lose count of anything!"

"You're goddamn right I don't. Why? Cause I am a genius!"

"Oh shut up will you? Now tell me, can you speak Afrikaans?"

"Nope."

"... jy's 'n idioot."

"Hey! I'm not an idiot!"

"I knew it! You do know Afrikaans! Let me guess, it's a part of your surprise or something right?"

"... You're weirdly perceptive when you're blind, anyone ever tell you that?"

"No! Because no-one, I repeat no-one, has ever dared to put a blindfold on me."

"So what you're saying is, that I'm special."

"... How long, Poly?"

"Just a minute, my sherry."

And this time, she did not raise an objection to me calling her sherry.

"Aaaannnnddd, we're here! You can take off the- okay, you just threw it away I guess. That's fine."

And the moment her eyes land on my surprise…

SNIP

"POLY! Did you just take a photo of me gawking at that?"

"... No?"

"Give me the camera Poly."

"No! You'll have to take it off my dead body!"

"Don't tempt me, you know I will!"

"... Fine."

After deleting the photograph of her dumbfounded visage, she turned towards me again.

"So… how rich are you exactly?"

"... Well that's a weird question to ask sherry!"

"Oh really? See I think it's perfectly valid, considering your surprise apparently consists of a FREAKIN' PRIVATE PLANE!"

Relax, would you? My father bought it this year when I got my pilot's license. I didn't buy it-"

"Hold on… there's no pilot in there?"

"Well, there's one right in front of you! And don't worry, by the time I'm done with you, you'll be able to get a license of your own. Now come on! The tour of Tinseltown awaits!" I strut forward in excitement, dragging her along by her hand, as she holds tight.

I open the door, before gesturing for her to get in, "Ladies first."

She hesitates a little, excited, but nevertheless a little apprehensive.

"Do you trust me, my sherry?" I ask in a joking tone, but my eyes convey utmost sincerity.

She looks deep in my eyes, before rolling them hard and swiftly walking into the jet.

The plush interior aside, the Gulfstream GV has a capacity of 18, 14 passengers, and 4 crew members.

Only this time, there'll be no crew, just me and my sherry.

"Now look below. You see that lit street? That is the world famous Hollywood Boulevard. The sidewalk to the right might seem familiar to you now. Any guesses?"

"The walk of fame." She breathed out, eyes wide, as she took in the sight of the LA skyline, from the co-pilot's seat no less.

"All right! Now last but not least, the piece de resistance, I give you one of the most posh and expensive neighborhoods in the known world, and incidentally where I live… Beverly Hills!"

"Oh… which one's yours?"

Down on your right, you see it?"

"No, all the houses look alike. Plus there's no lights so-"

"Okay, I've heard enough," I say, as I get out of my seat, and move over, leaning behind her seat, as our faces touch sides.

I point towards the veritable fortress that I call home, "See there? Follow my finger- yeah! That one. The one with the soccer field and the swimming pool, yep, that's home sweet home. Ever since I was born."

"... And all of a sudden, I no longer feel bad about you taking the bill at Musso and Frank's." She remarks dryly.

"Really? And it took my house for that to happen? Was my car and plane not enough?" I turn towards her, not moving an inch, as she tilts her neck a little towards the back.

"Not nearly enough. You were just so sweet… I thought I was taking advantage of-" I interrupted her with a scoff.

"Oh please! If anyone's taking advantage of anyone, it's me doing it so please, don't even- go there."

"Ok."

Huh, no snarky comeback. I guess the wine's buzz finally died down huh?

Liquid courage indeed.

"... Hold on… you're here."

"Yes I am?"

"Then who's steering the plane?!"

"Why, you my sherry. Just keep your hands steady, and don't make a move- here, " I lean forward, my arms encircling her seat as I reach for her hands holding the steering mechanism.

"Just keep it steady, and feel the hum through your hands… and look towards the front-"

But she didn't. Look towards the front.

She was looking at me, I noticed as I turn my head towards her.

Our eyes meet again, only this time, our faces are close enough to feel the other's breath on our skin.

We keep gazing at each other for a second, inching closer, but never truly reaching out.

So I took the initiative, and closed the distance.

And fireworks might as well have erupted into the night sky… or deep within my mind as our tongues intertwined.

I take my left hand off hers, and bring it to her cheeks to caress it gently, as we separate for a second… before rushing back in and this time… she was just as enthusiastic as I was.

 

Author's Note: There you go folks! An extra long chapter (4.5k) for those of you starved for romance!

P.S, I have never written a romantic scene before and this is kinda my first time, so please, oh please tell me how you found it in the comments. Your feedback means everything to me.