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Miles High Club (Airline Captain to Bimbo Stewardess TG)
🕑 Added 2025-10-06 23:26:50 +0000 UTCBy FoxFaceStories
An Anonymous Story Tier Prompt
Miles is a handsome and cocky commercial pilot who enjoys sleeping around. His chauvinist days will soon be over, however, as with each stop at an airport he finds himself becoming more and more of a bimbo who wants to get a lot closer to her captain. A lot closer . . .
Miles High Club
Miles Larsson grunted with satisfaction as he finally climaxed. The stewardess beneath him moaned in pleasure, her lovely body quivering from the sheer pleasure. He collapsed upon her, and it was only after several minutes that she murmured.
“That was nice, Captain.”
“Surely was,” Miles replied. “This was fun. Let’s do it again some other time.”
He got up and quickly got to changing, alarming Heather, the woman he’d just slept with.
“Wait, you’re not going to stay for a little bit?”
Miles winked as he put on his pants. “Sorry, darling. The life of a commercial pilot is a busy one.”
“We could share a shower together?”
“Oh, I’d love to, honey, but I really gotta go. I’ll shower in the pilot’s lounge. Besides, can’t be seen with a stewardess from a competing airline, can I?”
Heather’s eyes went wide, and then her expression turned to one of indignation. “You - you said you liked me! We went on a date!”
Miles began buttoning his shirt. “Aww, come on, babydoll. You know these flights were just a little interconnecting charter. We’re headed in different directions in the sky, baby. I just saw a sweet tush I liked and went for it.”
“But - but you took me on a date?”
He grinned, adjusting his tie. “Would you have slept with me otherwise?”
Fury filled Heather. Her rage and indignation was obvious. “You - you bastard! I hope you get to feel like I do, one day! I hope you get to know what it’s like to be treated like some kind of - some kind of - some kind of bimbo stewardess!”
At that exact moment, the window of the little airport suite flung open all on its own, sweeping over Miles. It put a chill to his bones, and he shivered, right up until he stalked over and shut the window.
“Well, I don’t think that’s likely now,” Miles said. He donned his cap and smiled, tipping it. “You have a good time on your next flight, Heather. If we don’t see one another again, this was nice.”
“You chauvinist asshole!”
He shut the door behind her. It wasn’t the first irate experience he’d had from a woman he’d seduced, but it was their own fault, he reckoned. Everyone knew the reputation of airline pilots, particularly stewardess. He was just playing the game.
***
Miles winced as he scratched his nipples. His latest landing at Munich had been utterly textbook, but upon landing he’d started to feel . . . strange. He was in need of a haircut, that much was obvious; his handsome 1950’s stalwart hero face was being ruined by his unfashionably longer hair, not to mention whatever shaving cream he’d been using had stopped the hair regrowth on his face.
“Goddamn it,” Miles muttered at his reflection, his voice cracking a little. “Nobody told me my damn uniform was looking loose.”
He stopped touching his oddly swollen nipples and went out into the captain’s lounge. There were some lovely ladies serving, and the handsome ladies man was more than a little interested in scoring some. He laughed with the other captains, shared some drinks during his off time, and swapped stories with them. As he did so, he made sure to give flirty looks to the prettiest waitress in the bar, a beautiful African-American woman with a ripe behind that was his absolute kryptonite. When she approached next, he passed her a tip: fifty bucks and his number on a card. She smiled and took it.
“Call me,” he said.
“I will.”
“Call me tonight,” he restated. “A captain’s a busy man, and I want to make time for a fine lady like you.”
Just an hour later they were in his hotel room, making out and stripping one another’s clothes off. It was a good thing too, because Miles’ uniform felt too big on him, and he didn’t want to feel ridiculous so much as powerful.
“Mhmm,” the woman said, whose name was Tanisha. “I’ve never slept with a captain before.”
“Well, consider it part of the honorary Mile High Club.”
She giggled. “Works for me, since your name is Miles! Oh! What’s wrong with your nipples? Are you having a reaction to something?”
Miles looked down and blushed. His nipples indeed looked swollen, with wide areolas that made them look damn feminine. Even his chest had sprouted out a little, as if growing breasts, and his body hair was gone completely.
“The fuck? I mean, just ignore it! It’s just a reaction I get after flight sometimes.”
She brushed his nipple, making him moan. They were surprisingly sensitive.
“Well, alright then,” she said.
They continued to make out, and soon she was on all fours, her lovely ass presented to him. But there was a problem: Miles was finding it hard to stay hard. He inserted himself into her, thrusting away as he always did, but he kept going limp, and had to close his eyes and focus, focus, focus on his own arousal. His thoughts imagined all the women he had bedded, but then they turned to imagine other prospects, too. Taboo prospects.
Sexy, manly captains.
“Oh God!” he grunted, and he climaxed right away, dreadfully early.
Tanisha looked back with a smirk. “Got you a little too excited, huh?”
But Miles couldn’t even play this off with a silly joke. He was too shell-shocked over what had just turned him on.
“I - I’ve got to go. Got to ready for a flight tomorrow.”
“But this is your suite?”
“Oh, uh, yeah. You’ve got to go.”
***
Miles tried to ignore his annoying nipples and little chest pooches on the flight back to Chicago. His hair was still too long despite him cutting it; had it grown back so fast? And his voice was still cracking. When he’d spoken to the passengers and given them a summary of the flight, his copilot Darren had looked at him and chuckled.
“Got a bit of a ball squeak today, Miles?”
“Shut up, asshole. Just remember you’re only the copilot.”
That had shut him up. Unfortunately said squeak continued, but at least there were no other strange changes to Miles’ body over the long flight home. He was grateful for that; part of him had been worried this might go further, and so it was with a more relaxed mind that he exited the plane after everyone had disembarked and the last checks had been made. He doffed his cap as he entered the captains’ lounge, grateful to be among his peers again. Unfortunately, this was also when his changes started again.
It began with his nipples, of course. He couldn’t stop scratching them, even pinching them. They were sensitive and bulging, and soon the pressure was building up in the flesh as well. The same was true of his hips. He kept on cringing and rubbing his flanks, which seemed to be stretching his pants. It was only when he made one too many faces that Darren, his copilot who’d had one too many drinks by this point, gave him a look up and down.
“Everything okay, Miles?”
“Y-yeah, it’s just . . . does my hair, like, look too long to you?”
Darren shrugged. “You’ve always had long hair, baby.”
His comment gave Miles pause. “It’s just, I feel kinda short. I’m normally a 6’1 guy, but lately I feel . . . not that.”
The circle of captains laughed.
“Please, you’ve always been a cute little shorty, Miles! Ain’t that right, fellas?”
They laughed again, and Miles’ heart beat faster. He excused himself, quickly moving to the nearest bathroom, and almost going into the woman’s by accident. To his horror, he really did look different. He’d changed again. His hair was now past his chin, long and brunette, and his eyelashes were longer too, his lips a little fuller. He was definitely shorter and when he cupped his chest . . .
“What the fuck!?” he gasped, feeling the small breast-like formations that were there. “This can’t be goddamn possible. I need to see a doctor or something.”
But he couldn’t yet, he knew. He had important flights coming up. His next break was in a few days. He just had to hope that by that point, his body would stop having whatever weird reaction was occurring. Then again, what kind of crazy reaction caused a man to lose inches in height!?
***
Another international flight, this time down to Mexico City. A shorter route, at least, though still pretty big, all things considered. Miles was nervous, and leaned on Darren more than he should have. His voice was higher, his skin far too smooth, and all of him just seemed way too soft. But there were no more changes on the flight, at least, and no one noticed anything odd about him, which was weird. He tried to stay in confident captain mode, even winking at the stewardesses who came up to serve him and Darren, but they seemed to react only to his copilot, as if he was the handsome one and not Miles.
When Miles landed the jet, a nervousness hit him. A chill wind seemed to come over the changing man despite being in a tunnel, and he knew instantly that something was very wrong. The pressure in his chest had returned, and the same for his hips, but now it had spread to his waist as well. To his horror, he could feel the pressure molding him, altering his form, bending it to make it more womanly. He didn’t even visit the lounge this time - passing it by, his thoughts were focused on Darren and the other pilots, admiring their forms and how handsome they were - and that was when he knew he needed privacy. His butt shifted more than it should have, his hips starting to sway automatically as he bolted for his room.
“It’s happening at my layovers!” he gasped, voice cracking up another octave. “I change at airports! Oh God, oh, like, God! I’ve totes got to get back into the air again or whatever!”
Miles paused, touching his throat. He was starting to sound like a woman, but his voice . . . the words he’d spoken . . . they were like some sexy bimbo with half a brain and far too much libido, exactly the way he usually liked them.
“What the fuck is happening to me?” he cried. “I don’t deserve this!”
He tore away his shirt, and this time his chest actually jiggled. There was no denying what he had freshly grown there; a pair of breasts that were getting fuller with each landing, and were now much harder to hide. They were definitely B-cups, he knew breasts from his experience holding them, and the changing man moaned as he fondled his nipples.
“Mhmmm, imagine a c-captain touching these. A sexy man who could - no! Fuck no!”
He jolted himself from the aberrant thoughts and removed the rest of his clothing. He was astonished to see that his hips were wider, his penis smaller, and his pubic hair starting to change in shape, becoming more like the classic feminine inverted triangle.
“Oh shit, oh Jesus! I’m, like, turning into a woman!”
Tears formed in his eyes. He knew he had to get help, but already he could feel the pressure upon him, the cold wind of change that was shifting his body ever more female. How long could he stay grounded and remain male? No, he needed to be in the air again as soon as possible. As soon as possible.
Before it was too late.
***
Miles soon discovered that it wasn’t just his body that was changing, but reality itself. When he got into the cockpit of the Airbus, Darren gave him a funny look.
“Look, Miles, I love ya, buddy, but I’ll ask you to give me back my captain’s seat.”
“I - what? This is, like, my seat!”
“Um, no it ain’t. Check your hat, cutie.”
Miles looked at his cap and was shocked to see that it indicated his position as copilot. “No, no, no.”
“Hey, it ain’t so bad, Miles. You put your nice tush in that seat. You get the most relaxing part.”
They took off, and Miles was horrified to realise how submissive he was being. Worse, how much he was actively looking to Darren for guidance. His handsome coworker was far more confident than he remembered, and Miles himself was forgetting ordinary things, things he should know. When he had to ask Darren for help, he found himself giggling in a silly feminine manner, like a total bimbo.
“Sorry!” he declared lightly. “I guess, like, this is why you’re the main pilot, right?”
He cursed himself for saying that, and Darren for chuckling in response. Why was this happening to him? Was it some kind of curse? Some scientific anomaly? None of it made any sense!
But at least he wasn’t changing. This was a long flight across the Atlantic, and for the duration of it he could pretend he didn’t have breasts, despite their clear weight and slight jiggle. He could pretend that his hips weren’t wider or his waist thinner, or his damn dick smaller. The last became obvious, though, when the lovely stewardess Tilda entered the cockpit, and he felt nothing when she made some flirty comments to Darren. Despite her looks, Miles was looking more at Darren, and the arousal wasn’t in Miles’ pants, but with his stiffening nipples.
“Stupid changing body,” he huffed to himself.
***
The changes continued to occur. Miles was correct about the pattern; whenever he was grounded, his body continued to change. His breasts came entirely out of hiding, and were soon full C-cups, a lovely pair of palm-fillers that he found himself playing with. His hips widened and his waist thinned, while his skin lost all blemish. He was even rejuvenating; soon his ID listed him not as thirty five years old, but thirty, and then twenty five, until he finally settled at twenty, much to his humiliation. His dick continued to shrink, as did his brain, seemingly. Despite how much the formerly overconfident captain tried to fight the physical and mental changes, he was increasingly a ditzy, giggly figure. He licked his lips at the sight of a hot man in uniform or a particularly manly passenger, and despite himself, he was moving in more sensual ways, sashaying his hips. He was even unbuttoning the top of his shirts and wearing tighter pants to show off his increasingly peachy tush.
“I’ve got to, like, get in the air again,” he cried when he went to bed at his on-site airport room. “I don’t want, like, to become some kind of bimbo! Ohhh, my penis is super small! And I swear I can’t remember, like, how to even drive a plane, or fly it or whatever. All I know is how to put on bras that make my boobs look super good and how to apply makeup all nice.”
That part was true. Several flights after his Mexico City charter, Miles had found that he had a craving to wear feminine clothing, and especially to finally put on bras and nice makeup. Soon, despite being seen as a copilot worthy to enter the captains’ lounge, the various figures there were flirting with him, asking for him to fetch them drinks, or even squeeze his backside when he turned away. When Peter slapped him on the ass, Miles had actually squeaked.
“H-hey! Don’t do that! It, like, makes me too horny!”
That had been the greatest humiliation, and one he still thought about as he rubbed his bubblebutt, trying not to moan with delight at the memory.
“What if I forget how to do anything at all?” he asked his mirror, desperately trying not to think of the beautiful brunette in his reflection as a woman. “How can I be even a copilot?”
He soon got his answer, because when he next moved to the cockpit there were already two full seats there: Darren and Peter.
“What?” he said, shocked. “What are you, like, both doing here?”
“Uh, we’re the pilots, remember?” Darren said. “What are you doing here, stewardess? Shouldn’t you be doing the demonstrations for the passengers?”
Something in Miles’ blood froze. He paused, and looked down at himself. He wasn’t sure if reality had just changed again in that very moment, or if he’d been wearing a rather attractive stewardess outfit the whole time and not noticed it. He’d even styled his long brunette hair, as well as his makeup.
“Or were you just hoping to see a handsome captain for a good luck kiss?” Peter teased.
Miles swallowed. “I - I’ll go do my routine,” he said. “I’ll, like, totes see you both again soon.”
“Looking forward to it!” Darren announced. “Especially from such a pretty face!”
A stewardess. Miles was now a stewardess. It was the ultimate humiliation, and yet his mind was already filled to the brim with knowledge of how to do this job, all while emptied of his pilot’s experience. Wait, stewardess? Not steward?
He checked his licence. Not, her licence. It said her name was Melissa Larrson.
“Oh no,” she said. “Oh no, oh no.” But the moment she looked up, she felt an undefinable need to do her job. Her new job as a stewardess.
“Like, hello everyone!” she said, pushing back her anxiousness. “My name is Melissa, and I’ll be one of your stewardesses here today. First, I’ll need you to watch and listen to a preflight presentation, and then I’ll walk you through our emergency protocols in the event of, uh, like an emergency!”
She continued, reciting what she needed to, and only occasionally stumbling thanks to her sheer shock as well as her increasingly bimbo-like nature. A number of men looked at her, and others ribbed one another and made murmured comments that she just already knew were about her increasingly sexy body. Strangely, it made her feel better and worse at the same time, as if her new form and role craved that kind of male attention. She felt that way for the remainder of the flight, smiling sweetly at the passengers, and even making little flirty comments back, or giggling when she received them.
“Why thank you! You’re not so bad looking yourself, mister!”
She presented exactly like a highly attractive woman, to the point where she couldn’t do anything but think of herself as such. When she visited Darren and he rested a hand on her thigh, she couldn’t help but softly moan a little.
“Maybe when we land, you and I can have some well-deserved fun?” her former copilot said to her.
A shiver ran through her form, a strong desire, an arousal that couldn’t be contained.
“I - I would sooooo like that,” she said, biting her lip.
She knew it was all wrong. She knew she had to stop herself. But Darren really was handsome. And she was so, soooo close to being a woman.
She kept that thought in mind for the whole flight. The moment the plane hit the tarmac, Melissa could feel the cold wind of change hit her again. She moaned, holding her body even as she disembarked after the passengers. She could feel the changes mounting, his hips widening and her breasts growing one last time, leaving them as spectacular Double-D’s. But best of all was the sensation of her penis. It slid up inside of her, making her moan in ecstasy. Darren must have seen her looking so blissful, because he put an arm around hers.
“Do you want to see a captain’s suite?” he asked.
Melissa shuddered. What was she becoming? But God, she needed this man. He was so handsome, so very sexy. Besides, her body was lustful as all hell.
“Like, soooooo much, you sexy captain!” she declared.
He took her there, and moments later they were ripping one another’s clothes off. Melissa was already wet between her thighs, her new pussy hungry. It was humiliating, but she was desperate to try it out, to feel him inside of her. Darren cupped her tits and sucked on them, making her writhe in pleasure. She snapped her legs wide on the bed and purred with bliss as he entered her.
“Ohhhhh, I can’t b-believe this is, like, happening!”
“Do you like it?” he grunted, sliding all the way in.
Her eyes went wide. The sensation was alien, but addictive as hell.
“I - ooooohhh - God help me, I love it! I love it sooooo much! I need you big cock inside of me! Start th-thrusting, please!”
He did so, which left the sexy stewardess crying out in ecstasy, her high voice sweet and musical as Darren pumped into her. She gripped him with her thighs, wrapping her legs around his lower back and clinging on for dear life. This experience was more wonderful than any copulation as a man, and her bimbo brain wanted more of it. She needed more of it. She needed Darren, every day and all the time.
“I’m gonna c-cum! I’m gonna - YESSSS!!!”
Multiple orgasms hit her like a series of earthquakes. She shrieked, clinging to him as he spilled his seed into her. Her eyes rolled into the back of her head, and it took a long time for Melissa to get a handle on her thoughts. She’d turned into a woman completely, and she had a feeling that this shame would be permanent. And yet . . . her new bimbo self really, really wanted it.
“That was amazing,” she purred.
“Damn straight it was,” Darren said, removing himself from her.
“Does this, like, make us boyfriend and girlfriend now?”
The man smirked. “Oh, sweetie pie. This was just like . . . planes passing in the night. A short little fling, doll. Nothing more.”
It was at that moment that Melissa fully understood how and why karma had hit her so badly, and why it had all led up to this point. Somehow, Heather’s hopes had come true: Melissaa now fully understood what it was like to be in her position, to be a stewardess just used up for sex and seen as a vessel for nothing more than that. And yet, despite this, her reaction was very different to Heather’s. Her body was already warming to the notion of what she could do with it, and she’d acquitted herself rather damn well as a smoking hot stewardess. In fact, she felt a growing excitement at the prospect of her next flight, and of the various compartments she could entice attractive men to join her in. It wasn’t like she was smart enough to fly a plane anymore, after all, but sex? Her body was now made for that, and given recent events, she knew it felt better than any captain’s chair . . . unless she was sitting on the captain’s lap in said chair, of course.
“You know how it is,” Darren continued. “I’m not ready to settle down. Plenty of fish to catch in the sea and all that.”
He smirked condescendingly at Melissa, like she was just another conquest. Instead, she just smirked back, posing sexually and moaning a little too erotically.
“That’s okay,” she said. “I can always find another sexy captain or even a passenger to join the mile high club with me, whenever I want! I’m not ready to settle down either. Now, can I use your shower or what? I want to look good for the lounge when I, like, make my super hot entrance. I bet other captains would like to go a whole load of rounds with me.”
It was all wrong, she knew. It was shameful and embarrassing. But God if she didn’t feel a burning need to be the hottest, sluttiest stewardess in the air. And her future would be just that.
The End
