Disclaimer: This a work of fiction. It is not real. It did not/will not happen in real life and should not be mistaken as such.
Chapter Twenty-Nine: Welcome To New York
Starring Taylor Swift
Codes: MF, Oral, Swallow
It was quiet in the cabin, apart from the constant hum of the engines, steadily keeping them aloft at approximately 37,000 ft. 3 ½ hours into a 6-hour flight from New York to Los Angeles. Business. Mostly. There was the added bonus of getting out of the city during the dreary winter months. Taylor sat silently, reading a book and Cole was napping. A jolt in the air awoke him and he rubbed his eyes blearily, stretching and mewling like a cat. Craning his neck, he looked around in wonderment.
“I don’t think I’ll ever get over this.” He stated matter-of-factly into the silence.
Taylor perked up from her book. “Huh? What do you mean?”
“I mean all this.” He said, gesturing to the private jet, its cabin decked out with every amenity imaginable. “Traveling in style.”
Closing the book with a snap, she fixed him with that familiar piercing blue gaze. “That’s good. You shouldn’t take it all for granted. I try not to.” She likewise gestured around the aircraft. “But sometimes I feel like I spend half my life on a plane, so it’s only natural I splurge a little.”
“It wasn’t a dig Swift. I guess I’m just still getting used to all this. This lifestyle. Your lifestyle.”
lifestyle.” She corrected him. “It’s me and
you now. That’s all I want.” There was a pause as she squirmed uncomfortably in her seat. “I know that it’s hard… having a million people watching your every move. Every second of every day.”
“As long as one of those people watching is you, I don’t care if it’s a billion. Plus, it’s not all bad. I’d say your personal private jet is a pretty big perk!”
“I knew it. You were only after me for my money!” Taylor said with an expression of mock outrage. “Besides you’ve been on my private jet before. Lots of times.”
“Not before we were dating. A few times, sure, and every time was memorable. But still only a few.” He was unable to stop smirking.
Cocking one perfectly manicured eyebrow in his direction, she matched his shit-eating grin with a sly smile of her own. “Any times in particular stand out?”
“I dunno, how about joining the Mile-High Club?”
“Ugh.” Taylor said, collapsing in an exaggerated dramatic fashion into a seat directly opposite myself. Glancing at her phone, she looked surprised. “Oh my god. Look at the time. I’m so sorry Cole. I’ve been ignoring you the whole flight. I’ve just got a million and one things to take care off. Things with the new album are absolutely insane.”
“Are you kidding me Swift? I’m fine! This is so fucking cool!” I said, staring slack-jawed around the interior of the plane. It had been nearly six hours and I still wasn’t over it.
“Jeez, you think you’d never been on a private jet before. I would have thought the excitement would have worn off by now.” She said teasingly, then paused, forehead crinkling in thought. “Wait. Have you never been before?” I shook my head back and forth, lounging comfortably as I stretched my feet out along the carpeted floor. “I could have sworn we’d flown somewhere before.”
“Nope Swift. We always seem to be headed in opposite directions. Plus, I never wanted to ask. I didn’t want to be that friend
.” I put the word in air quotes. “Seeing you is treat enough itself. I don’t care how I get there.”
Looking touched by my sentiment, she looked down shyly. It was true that we’d seen less of one another as our respective careers took off. Although, now with both of us living in New York that was beginning to change.
“Well then…” She said, steering the somewhat awkward pause in the conversation in an entirely different direction. “If you’ve never been on a private jet before then you probably aren’t in the Mile-High Club.” As she said it, silky smooth legs uncrossed under the pretext of straightening out a crease in her dress.
Staring blankly at her for a moment, I started to laugh, “Can’t say I am, why? Are you a member?”
“Of course.” She responded instantly. Then she covered her mouth with a hand, her eyes bugging out as though she said something she shouldn’t have.
I looked at her, a smile still tugging at my lips, thinking it was a joke. That changed when her expression didn’t. “Wait. Are you serious Swift? You’ve done it up in the air? In this
plane?” Mouth still shut tight, she nodded silently. “What?!?
With who? When? More than once?” Taylor only shook her head silently from side to side, refusing to answer any questions. “Alright then. Wow.” I looked around coolly and said to no one in particular, “Taylor Swift. In the Mile-High Club. Who would’ve thunk? Although, really, when you think about it, it doesn’t seem all that crazy. Especially considering how well I know you.”
Returning to my attention to Taylor, I gave a start. An enormous devilish grin was plastered on her face. Standing up, she swayed slightly as some gentle turbulence rocked the plane and moved in my direction. I knew that look all too well. Stopping just in front of me, she slowly descended to her knees, fingers taking hold of the armrest on either side before slipping down onto my thighs.
“Consider this your official invitation then.” She said seductively, fingers tracing the outline of the hardening bulge in my pants.
“Swift. The flight’s almost over.” I stammered, hard to think straight when all the blood I had was rushing towards my ever-stiffening groin. “We’re landing soon…”
“Sir. Please just sit back and enjoy the remainder of the flight.” She said, her fingers somehow already having undone my belt and now working on my pants.
*ZZZZZIPP* and my fly came down, her nimble hand disappearing inside. I felt her grasp it through my boxer-briefs, responding with a noticeable throb as her grip tightened. A giggle sounded as she squeezed tightly and withdrew, tugging my pants and underwear downwards until they were securely nestled around my ankles. Dick now free, it stood tall, heavy balls spilling out beneath it and ass settling into the warm leather of the seat. Manicured fingers curled around the stiff pole, jerking it slowly while electric blue orbs stared at me above grinning red lips.
“Please ensure that your cock is in the upright and locked position as we prepare for landing!” Taylor said, tracing her nails along the veiny underbelly, up and around the winking tip and along the outline of the swollen crown. Clearly relishing her role, she said gleefully, “Oh my! It definitely is! Sir, how did you get this through security?”
She didn’t allow for an answer as her head descended, lips wrapping about the bulbous bellend, sucking something fierce. Loud wet slurps escaped those scarlet puffy pillows as the pressure intensified, and they slid lower and lower down my length. Tongue cushioning the underside of my schlong, I could feel long broad licks, even as she sucked more air in. The slight bumping and jostling of the plane didn’t seem to disturb her, because in what seemed like no time at all, she was pressed down to the base. Lips stretched accordingly and cute button nose digging into my groin, I felt a vibration that had nothing to do with the aircraft as she gave a throaty gurgling moan of pleasure.
If the plane itself had been going down, I could not have been white-knuckling the arms of my seat harder. Toes curling, my legs stretched, twitching uncontrollably as she dislodged me from her gullet and ascended upwards, a vacuum seal of tightness remaining unbroken. Reaching the tip, she left it with a kiss and I looked down, light-headed and with blurry vision. The shaft was smeared red, her lips much pinker than when we had started. One hand gripped the slick base, wielding it like a spear as she circled the wobbling tip around her velvety smeared gobsmackers before diving back in for seconds.
Blonde strands fell forward, escaping from behind her ears to tickle my thighs and obscuring her big blue eyes from staring up at me. With gentle urgency, I tucked them away, her head bobbing fast now. Each frantic journey to the base sent me quivering as her throat stretched wide only to find myself hurriedly withdrawn and forced back down it once more. Moving from behind a cloud, sunlight burst forth, spilling across us as Taylor released me, taking a deep gasp. Sinking her chin down against the seat, those fingers curled once more around the slick shaft, stroking. Flicking out her tongue, it tickled and teased my balls, licking and lapping at them.
“I do so love airline nuts.” She said, before inhaling one spunk filled gonad into her open maw.
A loud, hard sucking sound emanated from between my legs, her hand squeezing another fresh dollop of precum to ooze down my hard length. Working one nut back and forth with her wet tongue, she released it coated in drool with a *POP* and did the same to the other. Spitting that one out too, she straightened up while still kneeling, and wiped the few scant traces of spittle clinging to her lips with fingers sticky from precum.
“We provide only the best service to our customers on Swift Airways. Are you enjoying your flight so far Mr. Stephens?”
“Uh-huh…” I stammered, barely able to string two words together.
Rising to her feet she moved to the chair opposite me, hurriedly stripping as she went. I got a flash of smooth, alabaster skin, her perky butt, and even perkier tits before panties were tossed playfully in my face. Hanging off my nose, the primal smell of her arousal lingered heavily upon the damp fabric as I pulled them away to find her kneeling on the seat in front of me, arms hugging the back for support. That pale perky ass was now pointed in my direction. Peeking out were her bubblegum pink pussy lips, visibly glistening even from my seated position.
“Can I offer you an inflight meal?” She asked, head turned to face me.
“Absolutely. I’m starving.” I said, nodding eagerly and standing up.
Discarding the remainder of my own clothes, I knelt down behind her, balancing on my knees. She spread her legs as wide as she could within the confines of the seat, clutching the backrest even tighter. Resting my hands on her flawless calves, I stuck my tongue out and was about to dig in when a bit of rough turbulence struck the plane unexpectedly. Flying forward, my head smacked right against her tight toned ass, my outstretched tongue spearing her butthole like a bullseye.
“MHMMHMM!!” I exclaimed, arms swinging wildly as I tried to balance myself, face full of ass and lips puckered against her anus.
“OHHHH!!!” Taylor exclaimed, mostly out of surprise, some out of pleasure. “I’m sorry sir, but we are not offering that course on this particular flight. Maybe next time.” She flashed a wink at me.
Righting myself, I gave quick but thorough lick to her backdoor, swirling my tongue in a clockwise motion before moving lower. Dragging my lips across her taint, I settled in, slurping down her steamy velvet twat like it was indeed an inflight meal. Tantalizingly tasting her labia with my tongue, it roamed from one lip to the other before tickling her clit. Lips pressed tight around her sex, I sucked and licked, lapping up the arousal leaking from her. Hands wandered up from toned calves along smooth thighs, over hips and coming to rest upon her ass. Squeezing and massaging those fit cheeks, my tongue darted in and out of her, flicking rapidly back and forth. Eyes shut tight, I felt her fingers reaching back, running through and tousling my dark hair as I continued munching box. Before long, those same fingers were tugging upwards, urging me to stand and give her something a little bigger.
Rising up, I stood tall behind her, hands migrating to hips. Aligning my cock with her dripping cunt, I teased the sopping entrance before pressing forward, sheathing myself fully inside of her in one swift push.
“Swift…” I hissed. “Fuck. How do you always feel so good…”
Holding her hips like handles, my fingers bite into her skin as I started thrusting. A wide stance let me put power behind each thrust, long and slow at first, letting her really feel every inch. Arms constricting tighter around the seat, each deep dicking pressed the side of her face further into the chair. The speed intensified. Faster and faster. Quickly followed by force, each hump harder than the last. Smeared mouth opened wide, her face was burning red, grunting squeals of satisfaction echoing out. They turned to muffled as her brilliantly white teeth sank into the leather. Blonde hair, usually so styled and shiny was a mess, half of it falling on top of her head as she was squashed harder against the seat. The seat rocked back forth, metal and plastic alike squeaking in protest, not designed for the force being applied to it, far more than any kind of turbulence could provide.
“Yes! Cole! Yes! Keep going!” Words had returned to Taylor, mouth gaping like a fish as she took the full unbridled force of my full hard length.
Still, she wasn’t shrieking her head off as I knew she was perfectly capable of doing when rolling around between the sheets. After all, the pilots were still in the cockpit, even if the rest of the plane was thankfully empty. I was really hitting my stride, totally and utterly focused on pounding Taylor into a quivering sloppy mess. Then turbulence struck again.
The jet wobbled horribly and I reached out in vain to grab onto something. Losing my balance, I stumbled backwards. I half crashed, half landed in my own seat, an almighty thump sounding as my ass hit the cushion. Taylor, holding onto her seat, fared much better and turned around in surprise at the sudden empty sensation of her insides. Watching me fumble and curse up a storm, dick still jutting high from my groin and swinging wildly, she couldn’t help but give a snort of laughter.
“Please make sure that all carry-on items are properly secured during the flight as they may shift during turbulence.” She stared pointedly at my dick. “Here sir, allow me to help secure that.”
As the plane leveled out, her arms came undone and she stood up, strutting over to me. Straddling my lap, the seat was just wide enough for her knees to wedge themselves behind my ass as she sank down upon my cock. One hand reached for the headrest, the other found the seat adjustments. I felt the seat go further and further back, Taylor’s looming form only growing taller above until we were in a deep longue-worthy position. She began to ride.
“Why. Were. We. Not. Do-ing. This. The. Whole. Flight.” Taylor groaned out, a breathy syllable expelled each time she filled her snatch with every meaty inch I had to give.
Sliding along her jiggling thighs, both hands found her ass once more. Clutching a perky cheek in each hand, I squeezed tight, guiding her clapping cheeks along my shaft as she worked her hips.
“Don’t know. I’m gonna put a customer service complaint in with the airline though.” I retorted before my lips latched onto one of her bouncing breasts, sucking hard on the pointed pink nipple staring me in the face.
“I’m. Sure. We. Can. Make. It. Up. To. You. Sir.” Taylor wheezed, bouncing harder than ever before, the seat rattling like crazy. “We want you to ride this airline again Mr. Stephens!” All the words escaping in one huffy pent-up breath. “Oh, fuck do we want you to ride this airline again!”
One hand let go to give her ass a playful smack. I couldn’t see much with my mouth full of tit, but I could feel that satisfactory ripple as I gripped the other even harder, still slamming it downwards upon my fleshy pillar. Towering above me, her arms encircled my head, pulling me in tight, breasts smushed against my face. Her hips had a mind of their own, gyrating, spinning and rocking before resuming the hard up and down of loud fleshy smacking, echoing ever louder throughout the cabin.
“That’s it! Gonna… gonna cum! C-c-cum!” Taylor hissed.
I gave her ass another smack, harder this time. Her nipple was like a bullet between my lips, teeth gently scraping over it. The other was equally hard as I quickly swapped to it, slobbering trails of saliva across her chest. I could feel her muscles tense, the epicenter of the shaking tremors deep in her loins. Eyes flicking skyward, I could see the outline of her beautiful face, mouth open wide, head hanging backwards, sunlight streaming through her golden haloed mess of a head and eyes screwed shut. One final time she sank upon my thick slab.
“Ahhh-hhhh-ahhhhh!!!” She shouted, primal erotic noises the only thing she could vocalize as she climaxed.
Whole body trembling, I held her close rolling my hips upwards in a series of quick thrusts, off the sticky leather of the seat into her suddenly vice-like pussy. Each thrust was met with another spasm until I drove deep and held it there, her body vibrating all over until I finally felt her unclench. Head hanging loosely like an unwanted sleeping passenger, she slowly opened her hazy baby blues to look at me. As our eyes met and I gave a hard throb inside of her, barely holding back my own orgasm.
“Mhmmmm, fuck Cole. That is… the only way I want to travel.”
On shaking limbs, she slithered back down onto her knees on the floor in front of me, the seat quickly returning to an upright position. “Back where we started.” A quick look out the window and we could see the Manhattan skyline laid out before us. “Better hurry.” A quick wink and in the next second my cock had vanished from view.
Smacking my own head back against the seat, I was trembling from head to toe, Taylor bobbing up and down along the entire length with the greatest of ease. Eager to suck the cum, and perhaps my very soul, right out of me. It didn’t take long, the ground growing surprisingly closer with each passing second.
“Tay. Taylor. Swift! Fuck! I’m cumming!” I yelled out in warning, growing inside her gullet as she moaned in anticipation of impending jism.
Seconds later she was rewarded. Piping hot cum sprayed forth, erupting wildly from my cockhead, securely held between her lips, cheeks caved in with pressure. It throbbed, pulsating rapidly, splashing semen hither and thither across her oral cavity. Hand on the shaft she jerked with fast steady motions, milking me for all I was worth. Salty rope after salty rope was unloaded until my member gave one final twitch, balls thoroughly and utterly drained. Digging my fingernails out of the armrests, I looked down at her.
A huge smile decorated her lips, still sealed tight. Staring straight at me, a loud audible gulp sounded and those lips came apart as she smacked them together appreciatively. With a cheeky grin she said, “Mhmmm! Best inflight meal I’ve ever had! Delicious!”
Just then, the buzz of the intercom sounded, the pilot’s voice buzzing through. “Preparing for descent. Please take your seats and buckle up for landing.”
Taylor grabbed her discarded dress, half dressing as she settled in the seat next to me, still licking the last of my cum from her lips. As we descended and the minutes passed, we kept glancing at each other and laughing, the rationality of our brains finally catching up with the irrationally of our bodies in the post-orgasm haze. Before long, the wheels of the plane touched down and we both jolted forward in our seats, gradually slowing as we moved down the runway. The intercom buzzed again. “Welcome to New York Ms. Swift. We hope you enjoyed the flight.”
“I know I did. How about you Cole?”
“Technically I don’t think it counts unless your above 10,000 feet. That’s why they call it the Mile-High Club.” She said matter-of-factly.
“Isn’t that way more than a mile?” Cole asked.
Taylor shrugged, “I think it’s more like two, but you know I hate cardio. Plus, nobody flies at 10,000 ft. It’s around 37,000 ft or something like that.”
“So that would make our second time in a plane our actual first mile high fuck?” Cole asked.
“Are you referring to the time where we had a bunch of champagne before takeoff and you convinced me to do anal? And then I couldn’t sit straight in a seat for the rest of the flight?”
“I seem to recall anal was your idea.” He replied, unable to keep the mirth out of his voice.
“Mhmm. Agree to disagree.” She said before lapsing into silence. Her book remained unread as furtive glance after furtive glance was thrown his way. Eventually, she tossed her hands up in the air and said, “Damn, now it’s all I can think about.” Spinning around in her seat, she hugged the back of it and thrusted her big beautiful behind out in his direction.
Cole laughed and grinned, adopting a polite and professional tone, “Why Ms. Swift, I believe you’ve acquired enough frequent fucker miles for our platinum plus package. And I think you’ll really enjoy it.”
“Get over here and give me that platinum plus package. Right now.” She demanded, yanking down her shorts to reveal her bare bottom, unencumbered by the presence of underwear and gave her ass a slap.
End of Chapter Twenty-Nine