Lush Life: a Swift Trip

Early October, 2017, New York.

I'd gotten off the flight fairly quickly and throughout the ride to the hotel that Hailee gave me, I kept trying to get more information about Cara's friend. Hailee continued to be stingy, giving me little one-word answers.

Then I dug into my memory. Cara had a lot of girlfriends, but I didn't think Kendall Jenner would be of such high importance that her name couldn't be said over text. Ashley Benson didn't seem that important either. No offense to either of them, but Hailee treated Cara's friend like the president or the queen.

I kept thinking hard until the driver stopped in front of the hotel. I gave him a thank you and put my shades back on. I never worried about getting caught by Paparazzi when I was alone, mostly because I looked like a regular Joe Schmo. I entered the building Hailee described as a luxury hotel and saw Hailee sitting in the strangely empty lobby with her head down on her phone.

When I say the lobby was strange, it was like a horror movie aside from the barren amount of sunlight peeking in through the shudders. There was no one at the receptionist's desk and again, the only person in the room aside from me was Hailee. She clearly didn't notice me open the door.

"Psst." I whispered with my hands in my pockets.

"Shit!" Hailee jumped and stared at me like I wasn't the man she was just texting.

"It's me." I said after removing my hat and glasses.

"Jason!" Hailee kept her voice down as she moved towards me for a hug. She wore a comfy-looking brown jacket over a plain black shirt and blue jeans. Her long and lovely brunette hair smelled like strawberries and her makeup was done in a simple yet sexy, catlike look.

"Glad you could make it. Sorry for the whole... incognito thing but it was absolutely necessary that we keep this whole thing under wraps. You took an Uber right?" Hailee asked.

"Yes." I answered.

"Good. Very good." Hailee turned from me and pulled her phone from her pocket, thumbing away with her bright pink nails tapping the screen.

"So... what's the deal?" I asked.

"Ok," Hailee turned to face me. "I would love to tell you who's coming, but Cara's waiting in the hotel room."

"That wasn't my question. I mean what's up with the spooky shit? There is no one here?"

"Oh, this is just a secret spot. Kinda weird but no Paps even come around this neighborhood. We're expected a few blocks away so that's where they are. This specific hotel is sort of a... a fake." Hailee grinned at the absurdity.

"Is that legal?"

"Not really... but money talks. Besides this isn't the first decoy place you've been in. Look at Los Angeles." Hailee explained as she guided me to our room.

"It's just... this seems like a lot of secrecy."

"Says the guy who lives in the middle of nowhere." Hailee quipped. I kept my mouth shut on asking about the secret person. Hailee knocked at the door with light taps.

"H?" A familiar voice called through the door.

Hailee knocked again. The door clicked and Cara opened it with just a crack.

"Hi Jason." Cara said warmly.

"Cara." I nodded.

"Come in." Cara opened the door all the way and I was taken aback by the room. Even if the lobby and hallways were spruced up, it was like a completely different place. The place looked like a luxury Venice hotel with deep red carpet and walls and a massive couch in the center of it all. At the edge of the couch was a small black backpack.

The single window providing the only light in the place gave everything a dream-like feeling.

"She'll be here in twenty. That means we have time to prepare you." Cara said, quickly tossing her phone to the floor with a thump. Cara wore a simple white tank top with baggy khakis and white sneakers. Her long blonde hair fell straight down her shoulders and her face was makeup-free.

"Wait," I put my hands up. "Who is it?" I asked. Hailee and Cara looked at each other. Hailee's face was curled into a shy grin and Cara's was its usual angry look.

"Have a seat." Cara asked politely.

"Seriously. I don't know if you two are messing with me, but I'd like a little more details considering I flew all the way across the country." I said sternly.

Then there was a rhythmic knock at the door. Almost like it was a code.

"What the fuck?" Cara spat under her breath. She zoomed towards the door and opened it. Then it hit me. I knew why Hailee was being so secretive.

Taylor Swift was standing there.

I wouldn't necessarily consider myself a huge fan, but I rarely dabbled in the music business anyway. Sure I've directed some videos and I've been to the Grammys as a favor, but this was different. Yes, I've met other singers who seemed nice enough, and I met Katy Perry at a party, but this was Taylor Swift.

"You said you'd be here in twenty!" Cara spat in a hushed voice.

"I know, I know. I thought Marco was gonna stop for gas." Taylor said, her voice floating through the room like it was coming through an overhead speaker.

"You said you wanted some prep." Cara said. Hailee and I exchanged an awkward glance.

"I mean... Can I see the guy?" Taylor asked. Cara sighed and opened the door all the way.

"Hello." Taylor waved and gave me a polite smile.

"Um... Hi. I'm Jason." I stammered. Strange isn't it? Someone like me being starstruck. Taylor wasn't even dolled up. Her face had no makeup aside from her simple red lipstick. She of course stood tall and confident, with long near endless legs packed away in a pair of plain blue jeans. Her skin had an almost rosy glow to it and her sandy blonde hair was straight and wavy, giving her a relaxed look that took her down from global superstar status to a regular girl. She finished her normal person look with a plain white T-shirt.

"Hi Jason. I'm Taylor. I hear you're my uh... my dick appointment." Taylor smirked.

"Should we still prep him?" Hailee asked, her voice breaking down the thick, unexplainable tension in the room.

"Sure. Why not? I need to make a few calls anyway." Taylor said before walking towards the chair that sat in the corner of the room. I kept my eyes locked on her, still not really sure if I was just imagining all of this. Before I got into the industry, I, like most people, made assumptions about the celebrities I saw on TV or heard on the radio.

Hearing Taylor Swift of all people say I was her dick appointment knocked the wind out of me. Cara and Hailee guided me to the couch. I sat in the middle, Hailee was to my left and Cara was to my right. Perfume filled my nose as their hands began to caress my body.

"See why I told you he needed to be prepped? He's all antsy." Cara said to Taylor who sat cross-legged across the room. Hailee laughed lightly next to me as her hands massaged my inner thighs through my dress pants.

"He was going to be antsy even if I showed up two hours late. You two know what to do." Taylor waved off Cara with a playful smile.

"Whatever." Cara twisted herself to reach out and start unbuttoning my shirt, her face right in front of me. Cara got the first two buttons popped. Then her expression softened before she leaned in for a little kiss.

"Sorry. I don't mean to be so... rude I just wanted this to happen the right way." Cara sighed. I found myself easing up a bit, especially with Hailee's hands rubbing over my crotch. I let out a small groan before leaning in to kiss Cara again. Cara stuffed her tongue into my mouth while unbuttoning the rest of my shirt. I kept my hands still as the heat of Cara's body pressed against me. As I and Cara kissed, my mind went into the smooth, relaxed state it went in when I was about to have sex.

My cock hardened in my pants while being snugly smothered by Hailee's hands. I heard Hailee moan slightly before I felt her fingers fumbling with the button and zipper of my pants. Cara broke the kiss when my shirt was fully open. I leaned forward to let it slip down my arms, leaving me shirtless. I caught Taylor sitting patiently out of the corner of my eye.

I lost my focus when Hailee tugged my pants down my ass. I helped her out by lifting myself up. Hailee took both my pants and my underwear down so my cock sprang out from between my thighs like a jack in the box.

"Hm." I heard Taylor mumble and then I saw her lean forward to get a better look. My cock pulsed like crazy. Hailee breathed in and removed her jacket, tossing it to the floor. Hailee then hastily stood up off the couch, unbuttoned her jeans, and slid them down her legs. Hailee quickly whipped her shirt up and over her head, whipping her hair back and forth dramatically. Hailee was left in a pair of lacy black panties and a matching bra.

"Lose it," Taylor said casually. Hailee playfully rolled her eyes and reached back to unclasp her bra, freeing her pretty pale tits. She also slung her panties down her legs, leaving her completely naked. Cara gripped the base of my throbbing meat just as it pulsed, forcing a deep groan to escape my lips.

"I missed you." Cara said in my ear. I turned and gave her a grin.

"You can book a flight to America whenever you want. You know my doors are open." I explained.

"That's so cute! You guys are like, actually friends?!" Taylor beamed across the room, her excitement infectious.

"You didn't tell her anything about me did you?" I asked Cara as Hailee got on her knees on the couch next to me.

"I told her the bare minimum." Cara said, failing to hide a smile.

"What's the bare minimum?" I asked.

Cara let go of my cock and leaned back to remove her tank top, leaving her completely topless. She then grabbed the back of my head and guided my mouth towards her tits, but before I could stick my tongue out towards her long pink nipples, she stopped me.

"I told her you had a big dick. I also told her that you knew how to use it." Cara smiled. I nodded in agreement.

"That's about it." Cara said as I felt Hailee's hot breath intercepting my cock.

"Hails?" Cara called.

"Yes?" Hailee whined.

"You have to prep him." Cara said like she was talking to a child. Hailee groaned like one and rolled off the couch. Hailee made her way towards the bag and unzipped it, shuffling through it. I kept my eyes on Cara's tits and Taylor. Taylor, who was still just sitting and watching, had an excited grin on her face. I had no idea when she was getting involved, but her anticipation made me want to up my game by at least a hundred percent.

Hailee grabbed a small vial of clear and watery lubricant and quickly got back on her knees on the couch. Hailee popped the red cap open and tipped the vial so the lube hit the tip of my cock. The room-temperature wetness leaked down every inch of my shaft as Hailee poured out a very small amount. Hailee put the cap back on and carefully placed it underneath the couch.

"Alright. Now stroke." Cara ordered.

"Can't I just,"

"I said stroke, Hails." Cara interrupted her. Hailee held back an eye roll before reaching down with both hands and stroking the slickness into my girth.

"Damn..." I groaned.

"Damn right..." Taylor added.

"I just love this thing... love how I can stroke it with both hands..." Hailee huffed in admiration as her soft, feminine mitts slowly twisted and stretched my throbbing thickness. Good lord, she was good at handjobs. (Which was exceptionally rare.)

I could tell Hailee desperately wanted to suck me, but she was focusing hard on getting every single bit of my size coated in oil. Hailee dropped both hands to my full, bloated nuts, firmly lubing them up even if I thought it wasn't completely necessary.

The only sound in the room was Hailee's hands making my crotch nice and slick. That was until Taylor slightly adjusted herself in the seat, now sitting like a man with both feet on the floor and her elbows on her knees.

"It's throbbing." Taylor huffed. I nearly came right then and there, but Cara finally shoved my face into her tits. I wrapped my lips around her left breast while sliding my tongue over her nipple like it was a popsicle. Cara moaned and forced me deeper into her chest. Hailee upped the pace and pressure of her handjob, this time really getting into the curve of her wrists.

We stayed like that for a while, with Cara forcing me to switch from left to right. I hungrily devoured both of them. Hailee was stroking me just enough so that I was close to cumming, then easing up when I was right on the edge. It was driving me insane and I decided to take out my frustration on Cara's chest.

Cara let out a grateful yelp before deciding to pull me away. My lips and her tits were slick with spit. Hailee was so close to getting my cock into her mouth, her long hair bunched up on my stomach.

"Can I pleeease suck it now?" Hailee asked with a desperate pout.

"Go ahead." Cara huffed, her mind clearly more focused on the thrashing I gave her tits. Hailee let out a pleased sigh and immediately wrapped her lips around my shaft. The ease at which she dove into her blowjob sent my head spinning. Hailee sucked and slurped so quickly that she nearly made all of the lubing pointless.

Cara climbed off the couch and slowly removed her shoes and pants, leaving her completely nude. Taylor gave a little golf clap at the scene that was unfolding. Cara ran her fingers through her hair before getting on her knees next to me on the couch the same way Hailee did.

Hailee was so focused on relentlessly sucking my dick she didn't notice Cara going for my balls. Hailee pulled up with a huff and a gasp, her gooey mouth slathered my cock in spit. Cara wrapped her mouth around my nuts, slowly working them with her tongue. Hailee wiped her lips and returned to sucking my cock, this time stroking the shaft at the same pace as her lips.

"Good lord..." I groaned. Taylor giggled. I looked at her and she looked at me. She then nodded in the direction of both Cara and Hailee's butts. I looked down at the pair of plump, rosy asses. I throbbed in Hailee's mouth as I moved my hands towards both girls glistening pussies.

I stuffed two fingers into Cara, which caused her to moan into my sack. I reached out to feel Hailee's pussy, which was beyond soaked. I could've shoved my whole fist into her folds. I instead teased her lips with a gentle brush of my index and middle finger. Hailee pulled off my cock with a surly smile and a giggle.

"Don't tease..." Hailee begged.

"Alright." I shrugged and shoved three fingers inside of her.

"Haah! Yes!" Hailee grunted before placing her plump lips back around my cock. Hailee bobbed her head at the same pace I fingered her slit. Cara was still glazing my nuts in a warm soak of spit. I felt my body locking up and I didn't know if I wanted to cum yet. I just closed my eyes and kept my attention on Cara and Hailee's pussies. I jammed my fingers in and out of Hailee and rolled my fingers gently inside of Cara.

Then I decided to curve my index finger inside of Cara. The blonde spat my balls out with a hearty sigh.

"Oh Lord... that's gonna make me... Keep doing that. One more finger." Cara begged and drooled against my cock. I did as I was told, forcing a wheeze to escape her lips.

"Ohm..." Cara mumbled as she placed her mouth back on my balls. My hands were now drenched in both girls' slick fluids and my cock was being overworked with spittle. Taylor stared at us while rubbing her slim stomach, teasing the taut skin underneath.

I could've sworn I saw her nipples poking through her shirt. Taylor grinned and lifted her shirt up to her collarbone.

I came. Hard. Like my entire body jumped.

They weren't the biggest or the fullest, but they belonged to Taylor Swift. They were firm, teardrop-shaped, and pretty. I'm sure you know by now that seeing a pair of tits shouldn't make me cum like a geyser, but again, Taylor Swift.

"Hrmph! Glrk!" Hailee gagged as multiple thick shots of my cum barreled down her throat. I removed my hands from their pussies and waited for them to come up. Cara removed her mouth from my balls first, but before I could do anything, Hailee arose with a mouthful of cum.

"Gimmie!" Cara yelped, opening her mouth wide. Hailee raised her head slightly and pursed her lips to share my load with Cara. The spunky concoction fell onto Cara's tongue as easy as butter and Cara moaned gratefully at the taste. Hailee let out a sizable helping of my cum before craning her neck to kiss Cara.

Little droplets of my seed fell back down onto my slightly softening cock. Cara and Hailee looked down at the same time, silently waiting to see who'd pounce first. Then, Taylor stood up and kicked off her boots. Her chest was still exposed and her skin was slightly flushed.

"Alright. Good prep, ladies." Taylor said, her voice slightly husky. She grabbed the button of her jeans and popped it with a quickness that rivaled my stripping. Taylor kept her eyes on us while digging her hands into the waistband of her jeans, keeping a smile on her face the entire time.

Taylor pulled her bottoms down her long, milky white legs and stepped out of them when they hit the floor. No panties. Just pure glistening pink. Taylor quickly got rid of her shirt, leaving her naked. Her long, lively, and statuesque figure combined with her slight hesitation made her look like a one-of-one recreation of The Birth of Venus.

"He's all yours." Hailee giggled before giving Cara one more light kiss. Cara and Hailee then backed up towards the arms of the couch. Taylor eyed me hard before looking up in thought, that little knowing smile never leaving her face.

Taylor then spread her legs, doing a picture-perfect split that hypnotized me. Taylor kept her eyes locked on me as her legs split against the carpet. When she hit the floor, she swung her head to brush her hair out of her face. The whole time it seemed like she was going over choreography for a music video.

Taylor then slinked forward on her wiry arms, her eyes now glued to my pulsing dick. Taylor's lips were a hair away from my shaft. I felt my breathing quicken at an alarming pace.

"Let me just..." Taylor opened her mouth, letting her tongue fall out and smack the part of my cock where my shaft met my balls. Taylor *slowly* licked up the entire length of my dick, catching little bits of cum on her tongue along the way. Taylor swiped at my tip with a smile before leaning back and swallowing.

Taylor's eyes widened at the taste.

"You know not to tell anyone about what's going to happen in this room right?" Taylor said, her voice light and airy.

"Of course..." I nodded quickly, eager to feel those cherry-red superstar lips around me.

"Good." Taylor gave my tip a tender kiss before lining it up and down with gentle pecks. Then she let her tongue fall out of her mouth like a fat sack, hitting my veiny shaft and licking it like it was an envelope.

I heard the faint slick sound of Hailee playing with her pussy and whimpering next to me. I saw Cara giving her slit long swipes with four of her fingers before bringing her own wetness to her mouth. Taylor kept kissing and licking until she had her lips pursed at the top of my cock.

"Oh shit..." I groaned. Taylor beamed and then opened her mouth, swallowing the first few inches of my cock. I wanted to rub the back of her head, but I was completely frozen. I felt Taylor's tongue against my shaft as she began to slowly bob her head up and down. She kept her eyes closed as she focused on technique.

It wasn't the best blowjob in the world, but I figured she was just warming up. I hoped she was warming up anyway. While I didn't expect Taylor to have elite blowjob skills, I hoped that by her hanging out with Hailee and Cara she'd learned something.

Taylor popped off my cock with a little gasp before reaching up to stroke it. Faint bits of smeared lipstick melded with her soft palm and my cock.

"Girls, if you want to get going go ahead." Taylor nodded in Cara and Hailee's direction. Hailee almost jumped off the couch. Cara quickly followed behind. Hailee was on her side with her knees hugged tight to her body. Cara got on her knees behind Hailee's amazing ass and immediately dove in. Cara gently spat a thick line of spit into it and licked it up before it could fall all the way.