A Life in Hollywood Ch.6 - Anna Kendrick (Rapture-Palooza) (Patreon)

A Life in Hollywood

Chapter 6 - Anna Kendrick (Rapture-Palooza)

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The air on the Rapture-Palooza set was thick with the scent of ozone and cheap hairspray, a chaotic symphony of last-minute adjustments that Osiah was quickly becoming fluent in. His promotion to Production Secretary was a welcome step up from the general mayhem of being a PA. The new role was less about fetching coffee and more about managing the intricate dance of logistics, a challenge he met with quiet competence. The real difficulty, however, wasn’t in the call sheets or travel itineraries. It was the persistent, low-frequency hum of rumors that seemed to follow him, a phantom narrative woven by whispers in makeup trailers and sidelong glances from the female cast. He was the guy with the hands, the guy who could unknot a shoulder with a few well-placed pressures. It was a reputation that was both a blessing and a curse.

He was hunched over a laptop in the temporary production office, a canvas tent buzzing with the drone of a portable air conditioner, cross-referencing flight manifests with hotel bookings when a familiar, melodic voice cut through the noise. “You look like you’re trying to defuse a bomb, not book a flight to Vancouver.”

Osiah looked up to see Anna Kendrick leaning against the doorframe, a playful smirk on her face. She was in costume, a slightly ridiculous but somehow endearing apocalyptic-chic ensemble. “It feels that way sometimes,” he admitted, gesturing to the screen. “Just trying to make sure everyone gets where they need to be without a mutiny.”

She sauntered in, peering at the spreadsheet. “Ah, the glamorous side of movie-making. I was just coming to confirm my travel. You’re my new travel agent, then?”

“Among other things,” Osiah said, a small smile touching his lips. “Production Secretary. It’s a fancy title for the guy who handles all the stuff no one else wants to.”

“Sounds important.” She pulled up a chair, sitting backwards on it, her chin resting on her folded arms on the backrest. The conversation naturally drifted from the mundane details of flights and hotel rooms to the bigger picture. “So,” she began, her tone shifting from playful to conspiratorial, “what’s the verdict? You’re deep in the guts of this thing. Are we making a masterpiece or a glorious, beautiful mess?”

Osiah leaned back in his chair, the plastic creaking in protest. He considered his words carefully. He’d learned that actors appreciated honesty, even if it wasn’t what they wanted to hear. “Honestly?” he said, meeting her gaze. “I don’t think this one’s going to be sweeping the awards circuit. I think the critics are going to have a field day.”

A knowing grin spread across Anna’s face. “I knew it. I can feel it in my bones. Every line I read, I think, ‘This is either going to be brilliant or the most wonderfully stupid thing ever committed to film.’”

“Exactly,” Osiah agreed, warming to the topic. “But that’s the thing, isn’t it? Sometimes you just have to find the fun in it. You get a script like this, you know it’s not going to be Shakespeare. So you just lean into the absurdity. You try to have a good time, and hopefully, that energy translates to the screen.”

“Thank you!” she exclaimed, pointing a finger at him. “That’s exactly my philosophy! It’s like, there are roles you take for the craft, roles you take for the career, and then there are roles you take just because the costume is ridiculous and you get to say things you’d never say in real life. This is one of those. It’s a paid vacation from seriousness.” She sighed dramatically. “I’m just trying to find the fun roles, you know? Right now, in the present. Not always waiting for the ‘perfect’ project that might never come.”

“I get that,” Osiah said, his voice softer. “I’m on the other side of it, I guess. Still paying my dues. Working my way up from the bottom. This secretary gig is a step, but there’s a long ladder to climb.”

They sat in comfortable silence for a moment, the air conditioner’s drone the only sound. It was an easy rapport, a connection forged in the shared understanding of the strange, transient world of a film set. It was then that Osiah decided to broach the topic that was always lurking just beneath the surface of his interactions on set.

“You know,” he started, trying to sound casual, “the new role has been great. No real difficulties with the work itself. The only… slight problem is the persistent rumor mill.”

Anna’s expression didn’t change, but a flicker of curiosity entered her eyes. “Oh? What kind of rumors are we talking about? That you’re secretly the one funding the movie with a Bitcoin fortune?”

Osiah chuckled. “Nothing that exciting. More… personal. About my… skills.” He felt a slight flush rise on his neck. “Apparently, I have a reputation.”

A slow, deliberate smile spread across Anna’s lips. She leaned forward slightly, lowering her voice. “I have to be honest, Osiah. I’ve been dying to ask you about that.”

He raised an eyebrow. “Ask me what?”

“About… you know.” She gestured vaguely. “The hands. The… magic touch.” She laughed, a little self-consciously. “But the conversation was going so well, and I didn’t want to make it weird or ruin it. I even thought about asking for one of your famous massages, but I got shy.”

Osiah’s heart gave a little thump. Here it was. The moment the rumor became a direct proposition. He looked at her, at the genuine mix of curiosity and hesitation in her eyes, and made a decision. “You don’t have to be shy,” he said, his voice low and steady. “And you don’t have to just ask about it. I can give you one. If you want.”

Her eyes widened almost imperceptibly. “Really? Right now?”

“The schedule’s clear for the next hour. My trailer’s a mess. Yours is probably nicer.”

Anna’s smirk returned, wider and more confident this time. “It is. Lead the way.”

The walk to her trailer was short, but it felt charged with a new kind of energy. The chaotic noise of the set faded away, replaced by the soft thud of their footsteps on the gravel path. Inside her trailer, the air was cool and smelled faintly of lavender and expensive lotion. It was a sanctuary of personal space amidst the temporary city of the film set.

“So,” she said, kicking off her shoes and wiggling her toes on the plush carpet. “How does this work? Do I just… lie down?”

“However you’re comfortable,” Osiah said. “Neck and shoulders are usually the best place to start. Lie on your stomach on the bed.”

She complied, resting her head on her folded arms. Osiah moved to the head of the bed, his movements fluid and sure. He placed his hands gently on her shoulders, feeling the tension coiled there from hours of filming. He started with a light, effleurage stroke, a gentle warming of the muscles. His touch was confident, professional, but with an undercurrent of something more, something that made the air crackle.

He worked his thumbs into the knots along her trapezius, applying firm, deliberate pressure. He could feel the tension melting away under his hands, her muscles softening and yielding. A soft sigh escaped her lips. “Oh, my god,” she murmured into the pillow. “The rumors… they don’t do you justice.”

Osiah smiled to himself. This was the part he both loved and dreaded. He did try to give a good, healing massage. He understood anatomy, pressure points, the flow of energy through the body. He wanted to bring relief, to unknot the physical and mental stress that was part of the job. But inevitably, there was a shift. The therapeutic intent would collide with a more primal current, and the women he touched would start to want something more, a different kind of release. They’d want to “repay” him, as they always put it.

He could feel it happening now. The soft sighs were becoming deeper, more breathy. Her body was shifting subtly under his hands, a small arch in her back, a slight parting of her legs. He moved his hands down her spine, his fingers tracing the delicate bones, feeling the shiver that ran through her.

He worked for a few more minutes, maintaining the professional facade, but he knew it was a losing battle. He was rock hard, and he was sure she could feel it when he leaned forward to apply deeper pressure to her lower back.

Finally, she spoke, her voice muffled by the pillow. “Osiah?”

“Yeah?”

“Flip over.”

He paused, his hands resting on her lower back. “What?”

“Flip over,” she repeated, lifting her head and turning to look at him. Her eyes were dark, her pupils blown wide with desire. “I have a theory. And I want to test it.”

He didn’t need to ask what her theory was. He slowly moved around the bed as she rolled onto her back. She looked up at him, a predator’s gleam in her eyes. She didn’t waste any time. Her hands went to the hem of his t-shirt, pulling it up and over his head. Then her fingers were on his belt, undoing the buckle with practiced ease.

“I’ve been wondering,” she said, her voice a husky whisper as she freed his cock, her eyes widening slightly as she saw it. “If those hands are that good… what about the rest of you?”

Before he could formulate a response, she was already moving. There was no hesitation, no shyness left. It had been burned away by the potent combination of his touch and her own curiosity. She shifted on the bed, her movements sinuous and deliberate, until she was lying on her side, her head propped up on one hand, facing him. Her other hand reached out, her fingers tracing a line down his chest, over his stomach, until they wrapped around the thick, heavy shaft of his cock.

“You know,” she murmured, her voice a low, throaty purr, “a massage is a two-way street. It’s about exchange. Energy. Reciprocity.” She gave him a slow, firm stroke, and a guttural groan escaped his lips. Her eyes were locked on his, a challenge and an invitation all at once. “Why don’t you lie down? Let me show you my appreciation.”

He didn’t argue. He stretched out on the bed beside her, the mattress dipping under his weight. Anna immediately moved, her body a fluid shadow in the dim light of the trailer. She swung a leg over his chest, straddling him in a reverse cowgirl position, her back to his face. He was treated to the perfect view of her toned ass and the glistening folds of her pussy, already slick with arousal. The scent of her, clean and musky and intensely feminine, filled his senses.

“Just relax,” she whispered, looking back over her shoulder at him. “Let me take care of you this time.” She leaned forward, her hair brushing against his thighs as she lowered her head. He felt the soft, wet heat of her mouth as she took the head of his cock between her lips.

The sensation was electric. She was good, incredibly good, her tongue swirling and flicking with an artist’s precision. But she wasn’t just focused on him. She shifted her hips, lowering herself down towards his face.

“Why don’t you massage my cunt too,” she breathed, her words vibrating against his sensitive flesh. “While I massage your cock and balls with my mouth.”

It was an offer he couldn’t refuse. He reached up, his hands gripping the firm globes of her ass, and pulled her down onto his face. He buried his tongue in her, tasting her sweet, salty essence. He went to work with the same focused intensity he’d applied to her shoulders, his tongue finding her clit and beginning a slow, deliberate circling motion.

Anna gasped, her mouth momentarily leaving his cock. “Oh, fuck,” she moaned, her body trembling. He could feel the vibrations of her voice through his own groin. She redoubled her efforts, taking him deeper, her hand stroking the base of his shaft in time with the movements of her mouth.

They became a single, writhing entity, a circuit of pleasure flowing between them. Osiah lost himself in the taste and feel of her, his tongue exploring every inch of her slick heat. He could feel her building, her thighs tightening around his head, her breath coming in ragged pants. She was grinding against his face now, using him for her own pleasure, and he loved it.

The first orgasm hit her like a tidal wave. Her whole body went rigid, a sharp cry tearing from her throat as she convulsed against his mouth. He held on, his tongue relentless, drawing out the spasms until she collapsed, panting, on top of him. He had one. She had zero.

But she wasn’t done. After a moment to catch her breath, she was moving again, her mouth finding his cock with renewed determination. She was insatiable, a woman driven by a singular, powerful motivation. He continued his assault on her clit, sucking and flicking, pushing her higher and higher. It didn’t take long. A second, even more intense orgasm ripped through her, her body shuddering uncontrollably. She was moaning continuously now, the sounds muffled by his flesh, lost in a haze of pleasure.

He could feel his own climax building, a tightening in his balls, a familiar pressure at the base of his spine. But Anna seemed to sense it. She pulled away, disengaging from him with a soft, wet pop.

“No,” she said, her voice husky. “Not like that. I want to see you. I want to taste all of you.”

She shifted again, swinging her leg off him and moving to kneel on the floor beside the bed. She looked up at him, her face flushed, her eyes burning with a fierce, almost desperate need. She took his cock, slick with her saliva and his pre-come, in her hand and guided it to her lips.

This was different. This was pure, unadulterated worship. She looked up at him, her eyes locked on his as she took him into her mouth, deeper this time. She was fucking herself on his dick, her head bobbing up and down, her jaw straining to take as much of his massive length as she could. Her hand was a blur on his shaft, her other hand cupping his balls, rolling them gently.

The sight of her, Anna Kendrick, on her knees, so completely lost in the act of pleasuring him, was overwhelmingly erotic. He could feel the last threads of his control snapping. He tangled his fingers in her hair, guiding her movements, his hips thrusting up to meet her.

“I’m gonna come,” he grunted, the words torn from him.

She moaned in response, her efforts redoubling. She wanted it. She wanted all of it. With a final, powerful thrust, he exploded, his cock pulsing as he shot his load deep into her throat. She took it all, her throat working as she swallowed every drop, her eyes never leaving his. She continued to suck him gently, drawing out every last spasm, until he was completely spent.

She released him, a triumphant, satisfied smirk on her face as she licked her lips. “Now,” she said, her voice a low, husky command. “Let’s really fuck.”

She climbed back onto the bed, straddling his hips. She was in control now, a queen on her throne. She reached down, guided his still-hard cock to her entrance, and sank down on him with a single, fluid motion. They both groaned as he filled her completely.

“Let’s do it like this,” she whispered, leaning forward, her hands on his chest. “This position, Face to face.” She began to move, a slow, grinding rhythm that was both intimate and incredibly intense. Her breasts were pressed against his chest, her nipples hard points digging into his skin.

She leaned in close, her lips brushing against his ear. “So you go to actresses’ trailers, massage them, and fuck them senseless, huh?” she breathed, her voice a low, teasing murmur. “Is that your M.O.? Your secret to getting ahead in this town?”

He gripped her hips, his fingers digging into her flesh as he met her rhythm, thrusting up into her. “Only the ones who ask for it,” he growled back, his voice rough with desire. “Only the ones who know what they want.”

She laughed, a low, throaty sound. “Oh, I know what I want.” She picked up the pace, her movements becoming more frantic, more demanding. “I want this big fucking cock. I want you to fill me up. I want to come all over you.”

Her dirty talk was a catalyst, fueling his own desire. He sat up, wrapping his arms around her, crushing her body to his. He captured her mouth in a fierce, possessive kiss, their tongues dueling, their breath mingling. He could feel another orgasm building in her, her inner walls clenching around him, her movements becoming erratic.

“Come for me, Anna,” he commanded, his voice a low growl against her lips. “Come all over my cock.”

That was all it took. With a loud, shuddering cry, she came again, her body convulsing, her pussy clamping down on him like a vise. He held her through it, his own release on hold, savoring the feeling of her coming apart in his arms.

When the spasms subsided, she slumped against him, her body slick with sweat. But he wasn’t done with her yet. Not even close.

He shifted his position, his strength and control taking over. He eased out of her, ignoring her whimper of protest, and maneuvered her onto her back. He grabbed her right leg, lifting it straight up into the air, her body a testament to her flexibility.

“Hold it,” he commanded.

She obeyed, her hands gripping her calf, holding her leg in a perfect vertical split. He knelt before her, his eyes feasting on the sight of her, completely open and vulnerable to him. He entered her again, the new angle allowing him to go even deeper.

He started to fuck her, hard and deep, his hips pistoning, his balls slapping against her with every thrust. The bed was rocking, the trailer filled with the sounds of their flesh meeting, their harsh, ragged breaths, and their shared, filthy litany.

“Fuck, yes! Just like that!” she screamed, her free hand clawing at the sheets. “Don’t stop! Don’t you fucking stop!”

He was relentless, a machine driven by pure, primal instinct. He was hitting a spot deep inside her, a place no one had ever touched, and she was coming again, almost instantly. This one was different, a continuous, rolling wave of pleasure that seemed to have no end.She was thrashing her head from side to side, her hair a wild, dark halo against the white pillows. The sounds coming from her were no longer words, just a continuous, high-p keen of overwhelming sensation. He was hitting a place deep inside her, a place no one had ever touched, and she was coming again, almost instantly. This one was different, a continuous, rolling wave of pleasure that seemed to have no end. She was lost in it, a ship tossed on a stormy sea of her own making, and he was the storm.

He could feel his own climax building, a roaring inferno in his loins. The sight of her, split open for him, her body wracked by relentless pleasure, was the most erotic thing he had ever seen. He leaned forward, his body covering hers, his weight pinning her leg in its vertical position. The change in angle made her gasp, her eyes flying open wide, unfocused and dazed.

“Look at me,” he growled, his voice a harsh command. “Look at me while I fuck you.”

Her eyes struggled to focus, finally locking onto his. They were glassy, wet with tears of pleasure, but the fire was still there, burning bright. He drove into her, harder, deeper, chasing his own release. He could feel her pussy clenching around him, milking him, demanding everything he had.

With a final, guttural roar, he exploded. His cock pulsed, pumping a massive load of hot, thick cum deep inside her. The feeling of him filling her triggered another, final cataclysmic orgasm. Her back arched off the bed, a silent scream on her lips as her body was wracked by the most intense convulsion yet. He held himself buried inside her, his body shaking, as he emptied himself completely.

He stayed there for a long moment, both of them panting, their bodies slick with sweat, the air thick with the smell of sex. Then, slowly, he eased out of her, lowering her leg gently to the bed. She was limp, completely spent, a beautiful, fucked-out mess. She was jelly, just as he’d known she would be.

He looked down at her, a slow, predatory smile spreading across his face. He could see the evidence of their passion, a mixture of his cum and her own arousal, beginning to trickle out of her, glistening in the dim light.

“I have a snack for you,” he teased, his voice a low, husky rumble.

She made a soft, inquisitive sound, her eyes fluttering open to watch him. He scooped up a dollop of the pearly fluid dripping from her cunt with his fingers. He brought it to her lips.

“Open up,” he commanded.

She hesitated for only a second before parting her lips. He slid his fingers into her mouth, letting her taste their combined essence. She closed her lips around his fingers, her tongue swirling, cleaning them thoroughly. Her eyes were locked on his, a look of utter submission and satisfaction in their depths.

“Good girl,” he murmured, withdrawing his fingers. He wasn’t done, though. He looked down at his own cock, still semi-hard and glistening with her saliva and his cum. “You missed a spot.”

He shifted on the bed, kneeling beside her head. He guided his cock to her lips. She didn’t need to be told what to do. She opened her mouth willingly, taking him in and cleaning him with the same devoted attention she had before, her tongue licking every inch of him, swallowing the last remnants of his release.

When he was clean, he pulled away and lay down beside her, pulling her into his arms. She snuggled against him, her head on his chest, her body still trembling with the aftershocks.

“You forgot to add something,” he said, his voice a soft, teasing whisper in her ear.

She made a soft, questioning sound, too exhausted to form words.

He chuckled, a low, deep sound that vibrated through his chest. “You forgot to add that I massage actresses in their trailers and make them drink the cum I pump inside their cunts.”

Anna just whimpered in response, a soft, helpless sound of pure, unadulterated bliss. She was still reeling from the pleasure, her mind a blissful blank. She nuzzled closer, her arm wrapping around his waist, holding on tight. The rumors, she thought, her consciousness starting to drift away into a sated sleep. The rumors didn’t even come close.