Mile High Club

Jessica held her laced black panties up and peered at them with squinted eyes. 

Hmm. Skip. 

Instead, she picked up its matching bra and slipped it on. While panties were not necessarily a ‘must’ for international flights – in fact, her stewardess uniform was so obscenely tight that anything other than her specially curated collection of paper-thin satin panties would create visible panty-lines of varying degrees – bras were definitely required. While attention was not something Jessica usually shied away from, protruding nipples were not something her head-stewardess, Beatrice, appreciated. 

That said, Jessica’s choice of lingerie was more importantly motivated by the fact that Benjamin – a new, young, hunk of a pilot – was on duty for the New York-Shanghai flight, and she’d had her eyes on him from the first day he showed up for work. Though conservatively-built, she loved his boyish grin, his tufty, black hair and his sharp, chiseled features. Jessica always found herself attracted to younger men, and Benjamin was no exception. Fresh out of flight school at twenty-three, Benjamin was the second-youngest pilot to ever be hired by her airline, missing breaking the record by a matter of days. Fortunately for Jessica, younger men were also thoroughly attracted to her – the twenty-nine-year-old stewardess’ ‘hobby’ was working out, and when she wasn’t in the air she was in the gym, sweating it out on the treadmill. 

Her ironically unhealthy obsession with fitness aside, Jessica’s fit figure, beautiful skin and exotic features meant that she had first pickings of the attractive men that worked the same flights as her. While her immediate boss was not particularly fond of Jessica’s flirtatious manner, Beatrice had little choice but to stay in Jessica’s good books because the pilots, most of whom were (perhaps regrettably) male, were thoroughly in favor of having Jessica on their flights. 

In any case, Jessica’s target for sexual conquest this time wasn’t just any pilot, it was the young, fresh-faced Benjamin. While she didn’t often struggle to lure a man into her hotel room after touchdown, she derived great pleasure from watching them writhe and squirm as she spent the flight slipping in and out of the pilot’s cabin, teasing them to death before she did.


“And this is Jessica, my favorite stewardess,” grinned Peter, the older, more experienced co-pilot on the flight, introducing Jessica to the younger Benjamin.

Jessica did a half-curtsy in jest, before casually placing her hand on Benjamin’s chest.

“I’m sure, I’ll be your favorite too,” she winked, running her hand down his body and lifting off just before she ran into his belt. 

Benjamin, smiled, flustered. His cheeks had turned a shade of pink, and by the time he had lifted his hand to offer Jessica a handshake, the stewardess had already turned around and slipped out of the pilot’s cabin, hips swaying. Quietly, the two men admired Jessica’s sensual stride for a moment, before snapping out of their trance and returning to flight preparations. 

“S-she’s uh,” Benjamin sputtered, still recovering from Jessica’s ostentatiously flirtatious nature, “Very attractive.”

“Mmhmm,” Peter grinned, slapping the young pilot’s shoulder, “And she loves pilots. Especially the new ones.”


“Will that be the red or the white wine, ma’am?” Jessica asked, leaning over the seat of the passenger she was serving. 

“White, thank you, doll,” the woman replied, flashing her a charming smile. There was a pause, as Jessica served the wine into a glass, before the woman asked, “Do they still put you poor ladies in these obscenely tight uniforms? I was under the impression that it was 2019.”

Jessica laughed. Before responding, she took a quick look around. Seeing that the business class seating area was relatively empty, she took the liberty of speaking more casually with the friendly passenger. 

“Ah, well, seems our CEO’s not been updated on the developments,” Jessica said, smiling, as she set the prepared glass of white wine down on woman’s fold-out table. 

Jessica paused for a moment and eyed the woman she was speaking to. Maybe a little older than Jessica, the woman had a carefully styled head of tomboy-length blonde hair, sharp, red lipstick on her full, plump lips and foxy, make-up accentuated features. 

She seems like fun. 

“Not that I’d want a scraggy new-age uniform, really,” Jessica continued, now confident from her assessment that the passenger was someone she could speak with ease to, “This sexy little number is what gets the pilots in my hotel room when we hit the ground. And sometimes… some other special stranger.”

“Well, more power to you then… Jessica,” the woman grinned, catching the name tag sitting just above Jessica’s right breast. “I’m Marie, by the way,” the woman said, flashing her gorgeously bright smile again. 

Jessica paused again, her mind whirring. She rarely did this, and even less so with women, but Marie was positively electric. Quickly looking around to ensure Beatrice wasn’t lurking in an aisle nearby, she slipped a piece of paper out from under her serving cart and scribbled her number down on it. 

“In case your first night in Shanghai gets a little lonely,” she winked, and slipped it under Marie’s glass, “I have the night there today before we fly back.”

Marie gave Jessica a look of pleasant surprise. Carefully, she slipped the paper into her clutch and mouthed ‘definitely’ to Jessica, who gave her newfound passenger friend a mischievous grin, blew her a kiss, and then continued down the aisle with her serving cart. 


Closing the door behind her, Jessica slipped into her rest cabin and kicked off her heels. Laying in bed, she let out a long, relaxed sigh. She enjoyed her little breaks quite some – Jessica always found that being in close proximity with the men she was eyeing for sex mean that she often had quite a bit of sexual tension that she enjoyed releasing mid-air. 

Sliding her dress up smoothly to her hips, she lay in bed and flipped through the notifications on her phone while she absent-mindedly diddled with her sex. When she’d cleared the pressing messages in her various social messaging inboxes, Jessica tossed her phone aside and began massaging her clit in earnest.

Marie seemed like an enigma, but a fun one. Jessica’s intuition told her that she would get a call from her, though that might put her in the position of having to choose between Marie and Benjamin – a tough choice to make. 

Obviously, Jessica would have loved if she could have both the young pilot and the distinguished passenger together in the same bed, but she suspected that Marie’s tastes likely only swung in one direction. 

As Jessica massaged her sex, dabbing at her wet slit and toying with her clit, her thoughts alternated between Benjamin and Marie. The sexy, female passenger looked like an absolute treat in bed – her thick, juicy lips and the perfectly-grabbable set of breasts she had hidden under her thin, white dress drove Jessica’s mind wild with lust. It had been more than a year since she’d been with a woman, and Jessica longed for a woman’s gentle, nuanced touch. 

But then, her thoughts wandered to Benjamin. He was so, so cute. His fresh-faced innocence was a charmer, and there was nothing more Jessica loved than taking the lead with a younger, more inexperienced man. Something about showing an eager-to-please college boy the ropes and blowing his mind with sex girls his age could never possibly provide turned her on immensely. She mentally undressed him, imagining the flustered young pilot’s throbbing hard-on begging to find its way into her tight, wet pussy. 


She could put Benjamin off for their next flight together. After all, he was just starting off with Atlantic and there wasn’t going to be a shortage of opportunities to seduce him in the coming months. Still, she was wary of the other stewardesses – not only were they just as adept at snagging the pilots’ attentions, but they were also in the (rude, in Jessica’s opinion) habit of strategically tying down the most proficient ones into ‘exclusive’ relationships. This meant that Jessica would be shut-out from the best dick on a layover till their chemistry petered out.   

She had to give Benjamin a taste of good, experienced pussy before anyone else claimed him, but she was similarly taken with the idea of spending her only night in Shanghai with Marie. 



“All good in here?” Jessica asked, shutting the pilot cabin’s door behind her. 

“Better now that you’re here,” Peter said, flashing his trademark cheeky smile. 

“Hah, ever the charmer,” Jessica smiled, before leaning down and planting a small kiss on his cheek. “How’s the rest of the trip looking, Captain?” she asked, resting a hand on Benjamin’s shoulder.

“U-uh, pretty good, actually,” Benjamin quickly answered, looking up, “Smooth sailing from here – clear skies and a moderate tailwind, so we’re thinking we might hit Shanghai half an hour earlier than expected.”

Mmmh, perfect,” Jessica said, massaging Benjamin’s shoulder between her slender fingers. 

She felt the young pilot stiffen under her grasp, and giggled, tickled by his adorably shy nature. Gripping his shoulders, she eased him into a gentle massage, trying to loosen the tenseness she had created in him.

Very tense,” Jessica said, leaning down and whispering in Benjamin’s ear, “I wonder if you’re as stiff down there as you are up here.”

Jessica smiled as she watched Benjamin’s cheeks flush, and him shift sheepishly in his seat. He chuckled softly in response, as flustered as he was the first time he saw her. She saw that the crotch of his tapered pilot’s uniform had tightened, and that the faint outline of his rod was beginning to crease against it. Leaning in closer, her fingers still massaging Benjamin’s tense shoulders, she took the opportunity to sidle up to him from behind and press her plentiful breasts against the side of his neck. 

“So, Captain,” Jessica said, her hands running smoothly down from the young pilot’s shoulders to his chest, “Gonna’ be a smooth flight, hmm?”

“Y-yup, we don’t expect any hitches from here,” Benjamin sputtered, angling his head slightly to face Jessica. 

Jessica turned to Peter. 

“Think I can borrow pilot-boy for a bit, then?” Jessica asked Peter, winking. 

“He’s the Captain,” Peter shrugged, “Ask him.”

“Whaddya’ say, sir?” Jessica asked, whispering in Peter’s ear, “I hear the pilots’ rest cabins are a lot roomier than ours.”

“I, uh,” Benjamin mumbled unsure, his eyes darting to Peter. 

“Go on, kid,” Peter said, giving the young pilot a friendly smirk, “I can take care of things back here.” “You owe me one,” Peter said, wagging his finger at Jessica as she towed Benjamin out of the cockpit. 

“I’m looking forward to paying you back,” Jessica cooed as the door shut behind her. 

Jessica turned to Benjamin. 

“Now,” she said, slipping her hand between his legs, grabbing at his crotch, “Time for me to show you how we do things on Atlantic.”

Benjamin’s response was the excited, gleeful grin that spread across his face. 


“This is roomy, shit,” Jessica said, looking around Benjamin’s rest quarters, marveling at the fact that it was nearly twice the size of her comparatively claustrophobic rest cabin. “If I’d had known, I wouldn’t have spent all these years waiting for the fucking plane to land,” Jessica mumbled to herself, thinking of all the times she’d diddled herself in the privacy of her own tiny cabin despite the fact that there was a hunk of a pilot not a hundred feet away that was so hot for her his cock was bursting out of his pants. 

“Hmm?” Benjamin murmured, not quite catching Jessica’s under-her-breath ruminations. 

“Nothing,” Jessica said, spinning around and stepping deliberately toward Benjamin. “What’s important is I have you, here, now,” she whispered, her lips brushing against his ear, “And I’m going to fuck the living shit out of you.”

The tension between the two had hit its peak. The second Jessica pressed her lips to the side of Benjamin’s face, kissing him, he in return pressed his face into her neck and kissed her back, hungry for her. The two kissed, their tongues flitting against one another’s skin, tasting one another, before they lips finally met and devoured one another. Kissing passionately, the sounds of the pilot and stewardess’ lips smacking filled the room, before their mouths opened and their tongues danced with one another’s. 

As they kissed, Jessica ran her hand down the young captain’s back, grabbing at his ass through his tight uniformed pants and digging her fingernails into his solid, muscled cheeks. Groping his tight, sensual form through his cotton trousers was enough for Jessica to moan in satisfaction, her lips breaking away from her fervent kiss as she breathed against Benjamin’s face. 

“You are so, fucking, hot,” she whispered, gripping his butt firmly between her fingers, before smacking it firmly in her palm. 

Releasing her grip, she brought her hands to Benjamin’s chest and ran them down his body, before slipping inside his suit and pulling his blazer off his shoulders and down his arms. Benjamin shook it off compliantly, and watched eagerly as Jessica brought her hands to his shirt. Gripping at his white, silk uniform, she tore it open easily in one, deft sweep, to the surprise of Benjamin. Two of the buttons in his shirt popped out from the force of Jessica’s yank, catching him off guard. 

“H-holy, shit,” he whispered.

“I’ve had a lot of practice,” Jessica grinned, before running her painted fingernails against Benjamin’s bare chest. 

Then she slipped her hands into the waist of his pants, before gripping at the buckle of his belt and undoing it in one, smooth movement. Then, she swiftly pulled it off his waist and cracked it in the air, eliciting a flinch from Adam.

She giggled. 

“Relax,” she smiled, dropping the belt to the floor, “I reserve the kinkier shit for my more experienced friends.”

Benjamin’s chuckled nervously, noticing the mischievously sharp glint in Jessica’s eye. Then he watched her unzip his trousers and pull them down to his ankles. He lifted each of his feet and let the stewardess pull them off, now on her knees, inches away from his throbbing, burning crotch. 

Jessica brought her face up to the pilot’s black, Calvin Klein boxers and watched as the outline of his cock throbbed against the confines of his underwear. A wet spot had already begun to form against the fabric where the head of his cock pressed against his boxers. Pre-cum was oozing out of it, and the musky scent of his sex was in the air. 

As much as Jessica was enjoying teasing the greenhorn, watching him ache with pleasure as he waited patiently for her next move, the sight and smell of Benjamin’s desire for her was stoking her own, fiery drive. 

Bringing her face up to his underwear, she locked eyes with Benjamin as she ran her tongue very, very slowly against the outline of his rod, feeling its heat emanate against her cheeks each time it throbbed excitedly. The tip of her tongue stopped against the wet splotch, and she immediately tasted the sweet-salty taste of his pre-cum. She kissed, sucked and licked against his heated crotch through his briefs, feeling his hands dig into her hair, wordlessly begging for her to remove the barrier of fabric between her lips and his cock. 

Now, Jessica reached between his legs and gripped his balls firmly through his briefs. Holding them tight, she locked eyes with Benjamin again, whose face was now a bright, bright shade of flustered pink. 

“What do you want?” she asked, her hand firmly squeezing his balls.

“I-I,” he sputtered, a tinge of a wince beginning to form on his face from the slight pain, “I want you to take my boxers off.” 


“And for you to s-suck my… uh, my cock,” he said sheepishly.

“Louder,” Jessica said, commandingly, her fingers curling more tightly around his prized jewels. 

“I want you to suck my cock, please,” the young pilot sputtered out, louder this time.

“That’s better,” Jessica said, breaking her serious demeanor with a devilish smile.

Releasing her grip on his crotch, she pulled his boxers to the ground, and watched with glee as his fully erect cock bounced in her face, free from its prison. With her idea of foreplay already completed, Jessica wasted no time – she impaled herself on his tool with a smooth efficiency that elicited a loud, pleasured groan from Benjamin. 

“Oh my g-god,” he whispered, marveling at Jessica’s ability to take his well-sized member down to the hilt with such ease. 

The stewardess bobbed her head against his cock with the energy usually associated with women much younger than her, slurping, sucking and licking at Benjamin’s cock ravenously. As she did – her lipstick smearing all along the length of the pilot’s cock – she fondled and groped at his balls, toying with them roughly in her hand. 

Above, Jessica heard Benjamin’s pleasured grunts and groans. He hung his hands limply by the side, still intimidated by Jessica’s sexual stature and thus unsure if he could place his hands on the back of her head, and guide her oral ministrations. Jessica, still tickled by the young pilot’s bashed demeanor, gripped his right hand and pressed it to the back of her head, closing his fist around a clump of her long blonde hair. Encouraged by this, Benjamin began guiding Jessica’s bobbing, slowing and upping the pace to ensure that he didn’t blow his load too early. 

As that went on, Jessica reached between her legs, her dress having ridden up enough to give her easy access to her bare sex, and pressed her fingers up to her lips. Teasing them gently, she smeared her juices along her pussy, and then diddled her clit while she willingly gagged herself against Benjamin’s cock. With Benjamin being shyer than usual, Jessica had no qualms about impaling herself on the young pilot’s cock to get the rough, primal satisfaction that came from having a sizeable cock pulling her lips apart and threatening to nudge the back of her throat on her own.

When she was satisfied with the job she’d done on Benjamin’s cock, evidenced by the sheen that remained on his rod from her spit, Jessica slipped his tool out of her mouth and stood to her feet. Riding her dress up to her tummy, she fell into bed and spread her legs open. 

“I did a good job with yours,” she grinned, “Now you’d better do a good job with mine.”

Benjamin understood the stewardess clearly, and dropped to his knees at the edge of his bed without a second word. Diving face-first into Jessica’s pussy with boyish eagerness, he pressed his lips up to her cunt and ran his tongue along her slit hungrily. 

Jessica moaned, and sunk her fingers into his hair. Another thing Jessica liked about inexperienced, younger men was their over-the-top eagerness to please. She was never one for unnecessary foreplay, and the way Benjamin buried his nose into her pussy without a ritual of ‘tease and release’ was refreshingly erotic. 

As Benjamin devoured her sex ravenously, his tongue lapping at her warm juices, Jessica began rocking her hips against his face, gyrating them to the rhythm of his frenzied sucking and licking. While she enjoyed his enthusiasm, his degree of precision when it came to hitting the ‘spots’ she needed him to was questionable. As he continued working her sex, Jessica decided to re-position herself. 

“I need you here,” she directed, patting on the bed, “Face up.”

Benjamin climbed into his spacious bed and got into position. Jessica then climbed over him, straddling his chest.

“Take a deep breath,” she said, before lifting her hips, and bringing them down onto his face. 

She let out a long, satisfying moan as she felt her pussy press up to his lips, and his nose nudging almost perfectly against her clit.

“Your face was made for this,” she smiled, not remembering any other man whose face was such a perfectly molded fit for her to sit on. 

She ignored Benjamin’s muffled reply, and began to rock her hips rhythmically, happy that now she could control just exactly how she was going to be eaten out by the pilot. Gripping onto his hair for leverage, she shook her hips back and forth forcefully, grinding her pussy against Benjamin’s face with desperate desire. When she felt was necessary, she would give Benjamin a few seconds to catch his breath before returning to her sensual, forceful gyrations. 

Minutes later, Benjamin’s face now liberally smeared with her juices, Jessica felt herself approach orgasm. Moaning, she collapsed over the pilot, her sex quivering uncontrollably, and her hips shuddering with unadulterated ecstasy. 

“Oh fuck, fuck, fuck, fuck,” Jessica panted, wave after wave of pleasure setting her body alight. 

As her orgasm ebbed to a close, she slid down and kissed Benjamin on the lips, tasting herself on him. The red-faced pilot was panting too, catching his breath after what had been an intense few minutes of being used as Jessica’s fuck-toy. 

“You… did a pretty good job,” Jessica cooed, running her finger along his lips, “Even if it meant just sitting there and taking it.”

“Thank you,” Benjamin grinned, as he wiped his mouth off with the back of his hand. 

“You are such a cutie,” Jessica laughed, rolling off him and laying in bed, catching her breath. “He looks like he’s ready to go,” Jessica said, reaching down and grabbing Benjamin’s erect, throbbing cock in her hand and stroking it casually. 

Immediately, Benjamin groaned, enjoying the stewardess’ exquisite touch. She smiled, relishing the pleasured contortions on his face. As experienced as she was, affirmation from a lover in the form of raw, wordless expression was always a welcome boon. 

Pulling off his cock, Jessica slipped off the bed and stood to her feet. Pulling her dress down to her thighs, she faced her back to Benjamin.

“Unzip me,” she said.

Benjamin stood to his feet and acquiesced, slowly pulling her zipper down. It ran all the way to her hips, giving Benjamin a small, tantalizing peek at her cheeks. When her zipper was down, Jessica slipped out of her dress, and unsnapped her lacy, translucent bra. Throwing it to the side, she pushed the pilot back into bed and climbed over him.

Gripping his cock in her hand, she climbed over him and smoothly slid it into her sex without a second look. Already thoroughly lubed up from her earlier orgasm, Jessica was able to take Benjamin’s rod into her pussy in one, fell swoop. 

Benjamin’s eyes widened as he felt his cock sink so smoothly into Jessica’s cunt, both surprised and overwhelmed by how easily she had invited his quite reasonably sized rod into her. Her pussy tightened around his cock once it had taken him in, and began squeezing and releasing his tool firmly as she rocked her hips back and forth, adjusting to his size. 

“T-that was amazing,” he stammered still surprised.

“Then you haven’t seen anything yet, cutie,” she grinned impishly, pushing him down by his chest and beginning to bounce on his cock. 

Grunting and groaning, Benjamin grabbed Jessica’s shapely, perky ass in both his hands, and eased her along her bobbing motion, bearing a part of her physical exertion. 

“Spank me,” she suddenly said, gripping at his neck between her fingers. 

“S-spank you?” Benjamin asked, unfamiliarly, having never had the pleasure of such a rambunctious sex-partner before.

“Spank me,” Jessica said again. 

Jessica was still riding his cock, though she had eased back down to a slow grind, allowing the pilot to fulfill her request more easily. Raising his hand with uncertainty, Benjamin brought it down on Jessica’s left cheek. A small slap rang out, but Jessica was far from satisfied. 

“Do it like you fucking mean it,” she said, her fingers curling around his neck, a hint of venom in her voice.

Benjamin raised his hand again and brought it down with more force and sting on her butt. Jessica let out a small moan, and slowly ground her hips against Benjamin’s cock. 

“Again,” she said whimpering, “Hurt me.”

Jessica felt Benjamin’s cock pulse with excitement inside her upon hearing her words. Jessica usually held a tight rein over dominance in her sexual encounters, but knew that releasing that control momentarily was probably as arousing for her lover as it was for her. She had a complicated relationship with pain, and right now, all she wanted was to have her cheeks reddened by the pilot she was riding. 

Benjamin raised his hand again and sent a stinging smack across her cheeks, finally executing a spank she thought was worthy of repetition. Leaning over, she pressed her face up to Benjamin’s and kissed him, before nuzzling up to his ear.

“Again,” she whispered, gently bouncing her rear on the pilot’s cock as she spanked her again, and again, and again. 

Minutes passed, and Benjamin alternated between giving the stewardess the sensual pain she craved, and soft, massaging rubs on her ass. The two moaned, kissed and fucked for what felt like an eternity more, with Jessica expertly regulating the bobbing of her hips to a slower, eased motion when she sensed that Benjamin was having trouble holding his orgasm back. 

Holding his cheeks in her hands, she brought her face up to his and kissed him hungrily on the lips. 

“I want you to cum inside me,” she commanded, suddenly speeding the rhythm of her bouncing. 

Benjamin immediately began groaning heavily, the change in pace causing his cock to throb excitedly inside the stewardess. His face straining, he dug his fingers into Jessica’s ass as he struggled to hold on for a little while longer, still eager to please the experienced woman. 

“Let go,” Jessica giggled, amused by Benjamin’s futile insistence on holding his orgasm back for her, “It’s okay.”

Her words were enough to drive the pilot over the edge. Grunting, Benjamin released his seed into Jessica. Shot after shot of his warm, thick cum spilled into her cunt, his hips rocking each time he felt his cock throb, painting her insides. 

Jessica eased her gyrations, coming to a halt as the last of Benjamin’s cum filled her cunt, and his cock began to lose its rigid structure. Pulling off of him, she kissed him on the cheek and sat on the edge of the bed. 

“I enjoyed you, Captain,” she grinned, as she cleaned herself with the tissues by his bedside, “Perhaps we’ll get a little more adventurous on our next flight together, hmm?”

“Y-yes ma’am,” Benjamin panted, still splayed out on his bed. 

“I have to get back to work,” Jessica winked, slipping her underwear and her dress back on, “See ya’ round.”



The flight had landed, and Jessica was rolling her luggage down to the taxi stand in the Shanghai airport, when her phone buzzed.

I’m shacked up at the Hilton. 

Ask for Ms. Jameson. Marie Jameson. 

I’ve told them to let any pretty-looking woman asking for me up.