A Life in Hollywood
Chapter 19 - Taylor Swift - Part 3
Taylor pushed back into his hands, ass rippling slightly under his grip. "I've been wet thinking about you all morning. Feel it. Touch my pussy. I'm dripping for you already. Slide your fingers in. I want them deep. And keep squeezing my ass while you do it."
He slid two fingers between her legs from behind, rubbing over her slick folds, spreading her wetness up and down her slit, then pushing inside. She was hot and tight, walls clenching immediately around his fingers. The wet sound was loud in the quiet room as he started pumping them steadily, thumb circling her clit. Taylor's head dropped, hair falling forward, her face visible in the mirror — eyes half-lidded, mouth open, cheeks already flushing darker.
"Yes," she breathed, pushing back to meet his hand. "Fuck my pussy with your fingers. Just like that. I need it hard. Make me cum before I have to go be good on stage. God, your fingers feel so good inside me. Curl them — yeah, right there. Keep rubbing my clit."
He worked her faster, fingers curling to hit that spot inside her, thumb pressing firm on her clit. His other hand stayed on her ass, squeezing and spreading the cheeks, watching the way her body moved. Her tits were still trapped in the sports bra but he reached up, tugged it down so they spilled free — perky, full, nipples hard and already tight. He cupped one fully, fondling the soft flesh, rolling the nipple between his fingers, pinching it just hard enough to make her gasp. Then he moved to the other tit, mauling it, squeezing the weight, thumb brushing the sensitive nipple while his fingers kept pumping into her pussy. He tugged on both nipples at once, rolling them, pulling gently, then harder as she moaned, the soft flesh of her tits filling his palms perfectly.
Taylor's moans got louder, filthier. "God, your fingers feel so good stretching me. I love how you fuck my pussy like this. Don't be nice — I can take it. Squeeze my tits harder. Pinch my nipples. Yeah, just like that. Pull on them. Make me cum all over your hand. Fuck, I'm so close already. Your hands on my tits and your fingers in my cunt… it's perfect."
She came the first time with a sharp cry, pussy clenching hard around his fingers, wetness flooding his hand and dripping down her thighs. Her face in the mirror contorted — eyes squeezing shut, brows furrowed deep, mouth open wide in a moan that turned into a broken sound, cheeks flushed dark. Her body shook, thighs trembling, ass clenching rhythmically as the orgasm rolled through her. Tits swayed with the movement, nipples hard and sensitive under his fingers as he kept pinching and rolling them.
Osiah didn't pull out. He kept fingering her through it, slow and deep, letting her ride the aftershocks while his other hand kept mauling her tits, squeezing the soft flesh, tugging on her nipples. "Good girl. Give me another one. Your pussy is still clenching. You're so fucking wet. Your tits feel perfect in my hands — so soft and full. I could play with these nipples all day. Look at how hard they are."
Taylor's breathing was ragged. "Fuck, Osiah… don't stop. Keep playing with my tits. I love your hands on them. Pinch them harder. Twist them a little. And your fingers — curl them more. I'm so close again already. Keep rubbing my clit too. I need it. Squeeze my ass while you finger me. God, I'm dripping all over your hand."
He did, fingers thrusting faster, thumb working her clit in tight circles, his other hand alternating between her tits — cupping, squeezing, rolling the nipples until she was whimpering — and her ass, gripping and spreading the cheeks so he could watch his fingers disappear into her soaked pussy. He leaned in, kissing the back of her neck, teeth grazing lightly, then sucking on the sensitive skin. Her ass pushed back against him, cheeks rippling as she moved, thighs starting to shake again.
She came the second time even harder, legs shaking violently, pussy gushing around his fingers, a raw moan tearing out of her. Her face in the mirror was pure wrecked pleasure — eyes rolling back, mouth open in a silent scream that broke into loud moans, sweat dripping down her temples, body jerking with each wave. Her tits bounced in his hand as she came, ass clenching tight around his fingers.
He stood up again, fingers back inside her, pumping hard while she was still sensitive. "One more. Give it to me. Cum on my fingers again. I want to feel this tight pussy squeeze every time. Your cunt is so wet for me. Look at yourself in the mirror while you cum. Watch how pretty you look when you fall apart."
Taylor was panting, body flushed and trembling, but she pushed back, taking his fingers deeper. "Fuck, Osiah… you're gonna make me cum again already. Your fingers are so deep — yes, right there. Don't stop. Make my cunt cum for you. Play with my clit too. Squeeze my tits one more time. Pinch my nipples hard. I'm so close — fuck, I'm cumming —"
The third orgasm ripped through her even harder. Her whole body seized, face contorting beautifully in the mirror — eyes squeezed tight, mouth wide open, a raw moan tearing out of her as her pussy pulsed and fluttered around his fingers. Thighs quivered, ass rippling, tits swaying as she came undone. She stayed bent over the vanity, breathing hard, body glistening with sweat, legs barely holding her up.
Osiah pulled his fingers out slowly, rubbed her ass gently as she came down, then ran his wet fingers up and down her thighs, spreading her own juices over the soft skin. Taylor turned around on shaky legs, sports bra still pulled down, tits out, leggings around her thighs, pussy wet and flushed. She pulled him in for a deep, messy kiss, tasting herself on his tongue, one hand cupping the front of his pants where he was hard.
"Fuck," she whispered against his mouth, voice hoarse and satisfied. "Three times and my legs are still shaking. You always know exactly how to wreck me. That was just the warm-up. After the show… you're mine. All night. I want you to fuck me until I can't think straight. I want your cum deep inside me, over and over. Different positions, different places. I've been thinking about it since you said yes to the tour."
She cleaned up quickly, fixed her hair and makeup, pulled the sports bra back into place and changed into the first stage look. The sparkly bodysuit hugged her body perfectly, the fabric catching every curve as she smoothed it down over her perky tits and the firm roundness of her ass. Before she left the room she turned back, gave him one more long kiss, hand on his chest, fingers pressing lightly against the fabric of his shirt.
"Go watch from the side," she said, voice still a little husky from the three orgasms she'd just had. "I'm going to kill it out there knowing what you just did to me. And later… don't make me wait too long."
She headed out, body still carrying that post-orgasm glow under the stage lights, ready to own the arena. Her long legs carried her with that easy, powerful stride, ass shifting under the tight costume with every step.
Osiah stayed behind for a moment, washing his hands thoroughly in the small sink, the scent of her still on his fingers and lips — sweet perfume mixed with the salty tang of her sweat and the unmistakable smell of her pussy. He dried his hands, adjusted his bag, and made his way through the backstage hallways toward the wings as the house lights started to dim and the roar of the crowd began to build.
Osiah stood in the wings as the house lights dropped completely and the roar of the Madison Square Garden crowd hit like a wave. The energy in the arena was electric — tens of thousands of fans screaming her name at the top of their lungs, phones lighting up the dark like a sea of stars, the floor vibrating under the force of all that excitement. Taylor took the stage like she owned it, the opening number exploding with lights, dancers in perfect formation, and her voice cutting through everything with that signature power. She looked incredible in the stage outfit — a sparkly bodysuit that hugged every curve, the fabric stretching tight over her perky tits and showing off her long, toned legs and the firm roundness of her ass as she moved through the choreography. Her tits bounced with the sharp dance moves, the sequins catching the lights and throwing sparkles across the stage as she hit the high notes and owned the space completely.
From his spot on the side, Osiah could see it all in detail. The way her body moved with power and precision — legs kicking high and clean, ass popping with the beats in a way that made the fabric of the bodysuit stretch and release, sweat already starting to make her skin glow under the intense stage lights. The crowd lost it during the big drops, singing every word back to her at full volume, the sound so loud it almost drowned out the band. Taylor fed off it, smiling that bright, genuine smile between songs, talking to the audience like they were old friends in her living room. She killed the ballads too, voice soft and emotional, standing still for a moment under a single spotlight while the arena went quiet enough to hear a pin drop, then switched back to the high-energy numbers that had the whole place jumping and dancing in the aisles.
The show was flawless from start to finish. Osiah watched the production side too — lighting cues hitting perfectly (thanks to the adjustments he'd made earlier during rehearsal), the big color washes landing exactly on the beat when she hit her marks, quick changes happening smooth as silk backstage, the crew calm and locked in with no panic. Every time she came off for a costume switch she glanced toward the wings, catching his eye with a small, private smile that said she knew he was there watching every second. Once, during a particularly sharp dance break, she turned just enough that he could see the way her ass moved under the sparkly fabric, the way her long legs powered through the choreography, the light sheen of sweat running down her neck and between her tits. She mouthed something that looked like "later" before spinning back into the number.
The energy never dipped. She ran through the set with that same fierce focus he'd seen in rehearsal, but amplified a hundred times by the crowd. During one of the bigger production numbers the dancers surrounded her, their bodies moving in perfect sync while her own stayed the center of it all — tits bouncing lightly with every jump and turn, ass flexing as she hit the sharp hip pops, long legs stretching in high kicks that looked effortless. The crowd screamed every time she hit a high note or dropped into a dance break. Osiah could feel the floor shaking under his feet from the bass and the thousands of people jumping along.
When the final encore ended and the house lights came up, the roar was deafening — a wall of sound that seemed to shake the entire building. Taylor came off stage flushed, sweaty, glowing with that post-show high. Her stage outfit clung to her body now, damp with sweat, tits rising and falling with each deep breath, nipples faintly visible through the fabric. Her long legs looked endless under the lights, ass shifting as she walked straight to him with purpose, still riding the adrenaline.
"Fuck, that felt good," she said, grabbing his hand and pulling him toward the exit without slowing down. Her skin was warm and a little slick under his palm. "The crowd was insane tonight. Best energy of the tour so far. But now I need you. Hotel. Now."
The car ride to the hotel was short but charged. Taylor's hand stayed on his thigh the whole time, fingers tracing slow patterns up and down the fabric of his jeans, getting higher with each pass. Her body still buzzed from the show — she was practically vibrating next to him, the scent of her sweat and perfume filling the back seat of the black SUV. She leaned in close at one red light, lips brushing his ear.
"I could feel you watching me the whole time," she whispered. "Every time I looked over and saw you standing there it just made me wetter. I kept thinking about what you did to me in that dressing room… and what you're going to do to me as soon as we get upstairs."
Osiah kept his hand on her knee, thumb stroking the inside of her thigh through the stage costume. "You looked like you belonged up there. Completely in control. The crowd ate it up."
She squeezed his thigh harder. "I was thinking about your fingers the whole second half of the show. How deep they were. How you made me cum three times before I even walked on stage. My legs were still shaking during the first three songs." She laughed softly, a little breathless. "And now I want more. A lot more. I want you to fuck me until I can't walk straight tomorrow."
The driver pulled up in front of the hotel. They barely waited for the car to stop before Taylor was out, pulling Osiah along with her through the lobby and into the private elevator. Her hand stayed locked in his the whole ride up, her body pressed close, the heat of her still radiating through the sparkly costume. The elevator felt too small with the way she kept looking at him, eyes dark with need, lips slightly parted.
They got to the suite — a big, luxurious space with floor-to-ceiling windows overlooking the city, a massive bed made up with crisp white sheets, and a living area with a big couch facing the view. The door barely closed before she was on him again.
This time there was no holding back. Taylor pushed him toward the big window, turning so her back was to his chest. "Right here. Bend me over and fuck me while I look at the city. I want to watch the lights while you stretch me open."
Osiah yanked her dress up over her hips, pulled her thong down her long legs, and bent her forward, hands on the cool glass.
{R-18 Scene Osiah x Taylor Swift 1182 Full Word Count aFireFist on p.a.t.r.e.o.n.}
They collapsed tangled together on the big bed, limbs intertwined, sweat cooling on their skin. Taylor's head rested on his chest, one leg thrown over his, her hand tracing lazy patterns on his stomach. Her body was still flushed, pussy still leaking his cum onto her thighs.
"Stay for more dates," she whispered, voice soft but hopeful. "I want you on the road with me. Different cities, different hotels. Maybe some risky places too — backstage again, the bus between shows, a balcony somewhere with the city watching. I want the adventures with you."
Osiah ran his hand down her back, resting it on the curve of her ass, squeezing gently. "I'm not going anywhere. The tour just got a lot more interesting with you. We'll have our fun, city by city."
Taylor smiled against his chest, pressing a kiss to his skin. "Good. Because this is just the beginning."
They stayed tangled like that, bodies pressed close, the distant city sounds fading as they drifted toward sleep, already thinking about the next show and the nights in between.
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