Flying High

Miles sat in the airport lounge waiting for his connection. He had been booked on a direct flight back home. Unfortunately that flight had been cancelled, so his airline had booked him on the next quickest alternative; a regular commercial flight to this airport, almost in the middle of nowhere, and then a flight in a small plane run by a small company called ‘The High Flyers Club.’ He’d never heard of them, which, with him being a pilot, was fairly unusual. But they had a scheduled flight that would happen to take him home.

He flicked through their brochure, and smiled at the phrases their marketers had used; “Your pleasure is our business,” and “We like all our passengers to enjoy a high quality personal service.”

He wondered what the plane would be like. He’d been on some services where it felt as though the plane was held together with string, and powered by elastic, with seats that had been fruit crates in a previous existence. He wasn’t particularly looking forward to the flight, but it would be for less then two hours, and then he’d be home.

A lady walked over to him. He couldn’t help but notice her; beige stilettos with a strap above the ankle, tan tights covering her long slender legs, beige midi skirt, white blouse, dark blue jacket with gold flashes, dark blue hat covering her dark hair, and impeccable make-up; she wouldn’t have looked out of place as a stewardess on a 1940’s aircraft, though there were no markings or insignia to show which airline she worked for.

She smiled the kind of smile that gave most men a twinge.

“Good evening. Captain Stokes?”

He nodded.

“I’m Tilly, from the High Flyers club. Your flight is boarding. Can I take your bag?”

“No, that’ll be fine,” he said. It was only an overnight bag, which he could drag along on its wheels.

“That isn’t a problem, sir.”

Before he knew what was happening, she’d taken his back with one hand, and with her other arm, she linked in with his as soon as he stood up, before guiding him, at a relaxed pace, to the boarding gate.

“I must be honoured, getting such a personal service,” he said, recalling the words from the brochure.

“We aim to please all our travellers,” she replied, as they sauntered onto the ramp to the aircraft.

At the aircraft door, another lady was waiting. Same uniform. Long, slender legs again. Blonde.

“Good evening, Captain Stokes. I’m Ursula, and I’ll be looking after you on the flight.”

She took the bag from Tilly, who turned, kissed Miles on the cheek, and proceeded back down the ramp, after wishing him a pleasant flight. Miles was a little stunned.

Ursula then took Miles’ arm, and led him on board.

“It’s a rather quiet flight today, sir. You’re our only passenger on this flight.”

Miles smiled. “So I can be assured of you best attention then.”

“Our travellers are always assured of that, sir.”

She led him to his seat. The seats were slightly wider than normal, and looked a little different. There were also a lot few of them than he expected, all in pairs. As he sat, it found his seat incredibly comfortable. He sat back, the seat was slightly reclined, and Ursula buckled him in, before stowing his case, and taking the seat beside him. He looked at her, a little surprised at cabin staff sitting next to a passenger, but she smiled back; another disarming smile.

The plane began to taxi; Miles hadn’t even noticed the door being closed, and hadn’t seen or heard any of the regular signals for the cabin crew. So far, he’d been looked after impeccably. The plane began its run to become airborne; Ursula’s hand moved on top of his, gently squeezing, and she gave him another warm smile.

After the climb, the aircraft levelled, and Ursula unbuckled herself.

“Let me make you more comfortable,” she offered, her voice soft and warm.

Miles didn’t object as she pushed his seat to recline a little further back. She unbuckled him, and started to loosen his belt, and untuck his shirt.

“Would you like a drink?”

“What do you have?”

Ursula smiled. “Pretty much anything you can think off. Would you like something hot, or cold? Or something alcoholic? We have a good selection of wines, beers and spirits. All complimentary.”

“What would you recommend?”

“My personal favourite is the Chilean Merlot.”

“Well that’s what I shall have then.”

He was a little surprised that instead of her going off to get the drink, she unbuttoned his shirts, and started to caress his chest, lightly circling his nipples. She loosened his trousers more, pulling them, and his trunks, down. She started to stroke his thigh with one hand, whilst the other took his cock, gently massaging it.

Another girl appeared, dressed in the same uniform, with a bottle of wine, and two glasses. She pulled out a table, and placed them down upon it, and pour out some wine into the glasses, before quietly withdrawing; Ursula continued regardless.

Ursula took off her hat, and unpinned her hair, letting her long hair fall. She resumed working on his cock, allowing her hair to drape around it, along his thighs and belly; Miles loved long-haired women for that reason. She pulled back his foreskin, and began to lick gently around his glans. Miles sighed, and began to realise just how personal the service of this airline was. She held his cock upright, whilst she slowly licked down the shaft, flicking his balls when she got down to them.

She stood up, and removed her jacket, neatly folding it and placing it on her chair. She untucked her blouse, and unbuttoned it slowly, revealing a white bustier underneath. Then she unfastened her skirt, allowing it to drop to her feet, revealing her long thin legs clad in tan stockings; Miles was most impressed.

She stroked herself between her legs, and looked at Miles, smiling.

“Would you like something to…” she paused as she looked down to her groin. “Eat?”

Miles took the hint. “I believe I would!”

She straddled him on the seat, moving up so that her pussy was by his mouth, and held onto the back of the chair. She still had her knickers covering her, so he licked at her clit and pussy lips through the material. However, as he licked, the material dissolved away, leaving a sweet taste behind. He moved his hands up to hold her thighs, and pull her in closer still, so she was almost sitting on his jaw, while he let his tongue go to work on her. He made everything very wet, to ensure the knickers disappeared quickly, allowing him unrestricted access. Ursula’s breathing deepened, as Miles continued licking at her pussy.

Ursula climbed down, and crouched between Miles’ legs, and began long, slow, gentle licks on his manhood. Miles could not help himself but to lean back, and push his pelvis up slightly, his cock quickly rising to attention. She looked up at his face, and smiled, before placing her lips around his glans, and slowly working her way down his shaft, taking his whole length in her mouth. She massaged his balls with her hand as she fellated him slowly and gently. Miles felt his heart beating faster in anticipation.

Then she stopped. After running her finger between her legs and seductively licking it, she spoke.

“Would you like me facing you, or facing away?”

“I’m sorry?” Miles was a little confused.

She moved up, to whisper in his ear.

“Would you like to see my breasts bouncing as I fuck you, or would you like to see my ass, as your cock goes in and out of my,” she licked her lips before finishing, “cunt?”

Her voice was velvety, and coupled with her talking a little dirty just turned him on more.

Miles paused, grinning. She leaned into him again and whispered.

“Or, if you’re feeling really fucking horny,” she pronounced each and every word precisely, emphasising the ‘g’s at the ends of the words; “you could use your big, throbbing cock to fuck my tight little asshole? Mmmm! Would you like to see your cock in my ass?”

Miles smiled broadly.

“That sounds… lovely.”

Ursula smiled back.

“Well let me get your cock nice and wet first; it’ll make it easier later.”

She climbed onto him, and straddling his, lap held onto his cock, and lowered herself down, until his cock was just inside her pussy. She paused for a moment, before gently pushing down, slowly sliding his cock inside her. When she was all the way down, she tightened her vagina muscles, giving Miles a gentle squeeze; Miles jolted slightly. She leant forward, her hands palms down on his chest, and her hair brushing around his chest. She moved a little more, so her head was close to his, her long hair above his head, shielding their faces. She moved in close, and gently kissed his lips; Miles twitched inside her. She kissed him again, this time longer, and Miles moved his hands to caress her thighs, stroking them gently, caressing. He wanted to touch her skin on her body, but she still had on her bustier. He settle for gently gripping her sides, massaging, squeezing.

After a while of gentle, sensuous kissing, Ursula started to gyrate her pelvis, grinding slightly into Miles’ lap. Miles responded by pushing his pelvis up, try to get even deeper inside. She moved up along his shaft, and back down again, and he met her on each trip, pushing his pelvis up slightly. As they continued with this rhythm, they kissed again, some short and soft, other longer and more probing, tongues meeting and dancing within their mouths. Their breathing quickened, and their thrusting became more intense; deeper and quicker.

Then Ursula stopped. Miles looked at her in puzzlement.

“I almost forgot,” she said, slightly breathlessly.


She climbed off, and gently held Miles’ cock, while she gave it a long, slow lick; the cock twitched.

“Hmmm. That should be wet enough now.” She smiled.

Miles still looked puzzled.

Ursula bent over the adjacent seat.

“I don’t normally get chance to do this,” she said. “But as there are no other passengers…”

She indicated to Miles to stand, and take his place behind her. Holding his cock, she guided it to her asshole, and pushed it in, wriggling a little in the process. Miles felt the tightness of her anus around his cock, and kept still; he wanted her to be comfortable before he started to move. She slowly pushed back, slowly, until he was all the way inside her. Then she started to move again, along his shaft, back and forth, her asshole squeezing it even tighter than before. Ursula moaned a little, and reached back to touch him with her hand.

“Mmmm. Yessss,” she breathed.

Miles felt a compelling urge to thrust. At first, he started gently, before gradually building up the pace.

“Yes, yes, yes,” she murmured on each of Miles’ thrusts. His worries had evaporated when she’d started encouraging him, and he thrust a little harder.

“Ooooooohhhhh!” she groaned.

Miles gripped onto the sides of her hips, and thrust harder and faster. She continued to urge him on. He looked down and saw his cock plunging into her ass, and out again, her cheeks wobbling slightly with each thrust, along with the slapping sound. He knew there was at least one other stewardess who was near, who could probably hear what was going on, and it turned him on a little more.

Ursula squeezed her asshole tighter around him, and he tightened his grip on her hips as he felt his climax rising. His cock seemed to get even bigger with more blood pumping through his veins, and he felt it throbbing, hard.

He slowed down his thrusting as he approached his orgasm. She tightened her anus muscles around him, squeezing him as tightly as she could; Miles exploded in her ass with a grunt. With each shot inside her, he thrust again, and again, until his cock was fully spent.

They remained in position a little while longer, until they had caught their breath. Then Miles slowly and carefully withdrew his flagging cock from her. Once out, she turned around, and sat him down.

She reached under the seat, and withdrew some wipes, and started the process of cleaning him up. The coolness of the wipes caused his erection to diminish even quicker. Once he was completely clean again, she put the used wipes into a small plastic bag, and placed it on her seat. She then dressed him again, being careful when moving his trunks and trousers up, and even tucking in his shirt after buttoning him up again. She quickly gathered together her uniform, leant over, and gave him a peck on the cheek, before picking up the bag of wipes.

“I need to go freshen up a little,” she said. “But Anya will take care of you until I get back.”

Miles looked up, to see the redhead who’d served the wine take the seat beside him. He smiled at her, and his eyes followed the still half dressed Ursula as she walked down the aisle.

“I hope Ursula has been taking good care of you,” she smiled.

“Ah, yes. Indeed.”

She reached over and picked up one of the wine glasses.

“You’ve hardly touched your wine,” she said, handing him the glass.

“Oh, thank you,” he said. “I guess I was a little occupied.”

She stroked the back of his hand that was resting on the chair arm. Miles hoped he wasn’t expected to perform all over again.

“It won’t be long before we land,” she said, as if reading his thoughts.

Miles was a little puzzled by something. “You don’t have any of the regular announcements and alarms, so how do you know?”

Anya smiled broadly. “We don’t like our travellers to be disturbed by such things. So we have a very discrete system.”

“Oh really? How does it work?”

“Ah,” she grinned. “That’s a company secret.”

Miles laughed.

After a few minutes, Ursula reappeared, looking pristine, and relieved Anya, who returned to the back of the plane.

“We’ll be landing shortly,” she said, as she leaned over to buckle him in, returning his seat to the upright position.

“Well that didn’t seem to take long,” he said.

“No,” she replied. “Time flies when you’re having fun.”

She winked at him and smiled. Miles grinned.

When the plane had landed, Ursula escorted him to the door.

“I hope you enjoyed your flight, Captain Stokes.”

“I most certainly did.” He smiled back at her.

“I hope to see you travelling with us again soon.”

She leant closer and whispered in his ear.

“Welcome to the mile high club.”

She gave him another peck on the cheek, before allowing another uniformed beauty to escort him to the gate.

“I hope everything was to your satisfaction, sir.”

“I couldn’t fault a thing,” he answered.

He later learned the cost of such an exclusive flight, and didn’t expect to use that airline again; certainly not if the company could help it. Well paid as he was as a pilot, he couldn’t even justify to himself that expense just to see Ursula again.

A few months later, he was preparing for a transatlantic flight. He was talking to a couple of the crew members by the door; Sophie and Guy. Rumour had it that between them, they’d bedded about 90% of the male staff of the airline, quite a few from the other airlines, and a smattering of male passengers too.

Something caught his eye; he looked down the gangway to see Ursula walking down, in her full uniform.

“I’ve heard about those,” Sophie said quietly, crinkling her nose a little. “The High Flyers Club airline.”

“I’ve heard stories of what they get up to on those flights,” added Guy, conspiratorially.

Miles leaned in. “I bet there no different to what goes on on some of our flights.”

Guy and Sophie looked at him, slightly embarrassed.

“Good morning,” Miles welcomed Ursula. “I hope you are well.”

He wanted to say something else, but would certainly say nothing in earshot of the other two.

“Captain Stokes.” Ursula remembered him. “I’m sure I’m in for a pleasant flight.”

She smiled broadly.

“I’m sure Sophie here will see that you’re properly looked after,” he put in wickedly. He turned to Sophie.

“Could you see if there are any seats available in Business class for our guest,” he said.

“Captain,” Sophie said coldly. “It seems our guest already has a business class seat.”

Miles looked at the ticket in Ursula’s hand.

“Our company likes to look after its staff,” Ursula added sweetly.

“Then I shall leave you in Sophie’s more than capable hands.”

“Thanks you.”

Ursula flashed him another smile, before Sophie escorted her to her seat. Miles turned to see Guy’s slightly astonished look on his face.

“I’d better get back to the cockpit, and start to get us off the ground,” he said.

A couple of hours into the flight, Russ, his co-pilot, offered to get some drinks.

“Sophie must be busy, as she’s usually brought them in by now,” he said.

Miles knew he’d been having the odd bit with Sophie when the chance arose. But he was right about Sophie not appearing with the drinks.

A few moments later, Russ returned, looking a little pale.

“What’s wrong?” asked Miles.

“I’ve just been down to the galley.”


Russ paused before continuing. “Sophie’s got her head up the skirt of some girl dressed as a 1950’s trolley dolly.”

Miles laughed.

“I’m surprised you didn’t stay to watch.”

Russ quietly took his seat.

After landing, the usual routines took place, and the passengers started to disembark. Miles decided to skip out, and see his special guest off the plane. He met up with Sophie and Guy checking the passengers off the plane. Sophie was grinning from ear to ear.

“You seem happy,” Miles remarked.

“Lucky cow has been offered another job,” sneered Guy.

Miles looked at Sophie. “Really?”

“Yea,” she answered. “I was chatting to Ursula earlier…”

Guy started coughing and spluttering.

“… and she was telling me about the pay and conditions, which are much better than ours, more than double. And she said there was an opening that I could take, if I wanted it.”

Guy spluttered again; Miles smiled at her unintentional use of phrasing: “…opening I could take.”

“Congratulations,” Miles offered.

“Thanks.” Sophie grinned.

She fit right in, thought Miles.

Ursula appeared, immaculate as ever.

“I hear you’re taking our Sophie away from us,” said Miles.

“I think she’ll fit right in,” said Ursula.

Sophie turned to Guy.

“We’d better get everything sorted for the turn around.”

Sophie and Guy left Miles and Ursula alone.

Ursula moved closer to Miles.

“You know we’re an expanding company, and we’re looking for new pilots,” she said, gazing in his eyes.

Miles laughed.

“And what special services are pilots expected to offer?”

“Just to fly the plane. Nothing more.”

Miles raised an eyebrow.

“Does it pay a lot more than any other pilot’s job?”

“A little more. For discretion,” she added.

“I see.”

“I think you should work for us though,” she said, stroking his arm.

“Why’s that then?” Miles gazed deeply into her eyes.

She moved in and embraced him.

“Because then,” she said, running her fingers down his chest, “I could see… a … lot … more … of … you.”



About ~T~

Saucy scribbler of fun, filth and fornication. Gentleman and Master of his own Domesne. On Twitter @Author_TMasters & View all posts by ~T~

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