Flying Solo

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A nervous passenger gets an upgrade to the mile high club.
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I was shaken out of my late-night doze when the shrill voiced woman announced that my flight was ready to board. I was going back home to London after several weeks working in New York.

I am quite an anxious flyer! So, to make it easier on myself I spent the previous day getting myself pampered. I had a massage, followed by a long soak in a bath. I had my eyebrows, legs, underarms and bikini line waxed and tidied up. All that waxing might not sound too relaxing, but I have been doing it for years.

To help me relax I was wearing my sexiest lingerie under my drab pinstripe suit. I had brought my sexiest pair of heels in my carry-on luggage. When I am feeling anxious, I chance a feel of the soft leather. I had learned to ignore the inquisitive looks from the security staff as they search my bags.

"This is final call for flight EK22104 to London Heathrow, please make your way to gate 6 as this flight is now boarding."

My tummy was a flutter as I got up and made my way to the gate and nervously boarded the plane.

I was so nervous that I failed to notice anyone else getting on. It was a 3 in the morning flight, but even so there should have been some more passengers.

About 20 minutes into the flight one of the beautiful hostess approached me and said, "Excuse me sir?"

I looked up at the beautiful leggy blonde stewardess and she continued, "There is a space in first class if you would like to upgrade?"

I thought for a second and considered it, it would be nice to be waited on, but there is no one in my row so I had plenty of room and I had intended to lie across the four unoccupied seats as soon as the meal was served.

So, I shook my head and politely answered her, "Thank you but I'm ok here, I don't think I could afford the upgrade." She smiled a big rosy red smile and left me alone.

About 5 minutes later she returned and said, "Hello again, there is only you on this plane, and we have eleven cabin staff, they're all at the front of the plane this would be a free upgrade and would make our job..." She placed her hand on my shoulder clasping it gently and if I wasn't mistakenly suggestively (was I that drunk?) before adding, "More interesting." I wasn't mistaken.

I grinned and said, "Sure if it will make things more interesting."

Standing up and stretching, of course my shirt rode up and if she looked hard enough, I'm sure she would have seen the ivory coloured silk and lacy Basque I was wearing under it.

Stepping into the isle shoeless, revealing the unmistakable sheen of my expensive stocking covered feet.

I reached up to open the overhead cabin bin to retrieve my carry-on bag, she stepped closer to assist me, much closer. As we both reached for my leather bag it tipped over and one of my red patent leather 5" chrome stiletto heeled court shoes fell to the floor.

She bent down in an almost impossible way, seemingly folding in half at her sumptuous bottom. Her cheeks pressed right into my stirring crotch. She lifted the fallen shoe and glancing at it and turning it over in her elegant hand before she handed it back to me saying, "Wow they're lovely, I would love a pair like that. Instead of these boring flats they make us wear here. May I?"

Before I had a chance to answer she had stepped out of her own shoe and passed it to me and slid on mine. I couldn't help myself, and I brought her well-worn cherry red leather flat shoe closer to my nose and inhaled her odour.

The world was passing me by, I was brought back when she smilingly said, "You're a foot guy then?"

I was bright red with embarrassment, unable to formulate an answer!

She had fished my second heel out of my bag and easily slid into it, "They're too big for me."

"Erm, my wife, eh, she has, ah big..." I tried to mumble some sort of excuse about my wife having big feet.

"Don't be silly, no one is here to judge." She said stepping out of my shoes and taking hers back from me.

"You can put yours on if you want, like I said you're the only one on board. We are having a few drinks in first and I would be great if I wasn't the one who ends up naked for a change." With that she gently placed a ruby red lipped kiss on my blushing cheeks.

I declined her offer and put the heels back in my bag and followed the hostess as her beautiful arse swayed with her steps.

She led me up the stairs of the Airbus A380 to the lounge. Up here we had enough room to really relax. They brought me some wine; two of the girls also joined me in drinking. Within the hour it had turned into a small party.

We began playing truth or dare. At first the questions were very tame. But when one of the flight crew joined us it got a little more daring.




"Truth!" I answered the hostess who had come to get me looked super excited.




"Are those heels yours?" she asked through giggles.

"Yes, they are" I blushed. But several minutes later it was my turn again. "Truth" I answered.

"Are you a gay tranny?" Came the question.




"Yes and no." I answered, nearly spilling my wine in the fit of nervous giggles that had come over me. Some of my fellow revellers looked confused.




"I am a transvestite, but I'm bisexual!" I noticed some of the girls smiling and winking to each other, but I passed it off as simply drunkenness.




"Truth" the co-pilot answered.




"Do you like guys or girls?" they asked him, cackling amongst themselves.




"Yes, I like guys and girls!" said the drunken man in uniform. The roars of laughter shock the plane like turbulence!




"Dare." I beamed how could it be my turn again?




"Err?" said the tallest hostess she was a similar build to myself.




"Ok swap cloths with Ursula." said the petite one, pointing to the larger one.





Within seconds I was in an executive bathroom putting on the sexy air hostess's uniform. Kathy, who was the one who, came to get me, had decided to help me she gasped when I disrobed revealing my ivory silk Basque, thong and luxurious lacy Stockings.

I did up the blouse and stepped into the knee length pencil skirt and zipped it up. She pushed me onto the chair, and soon my face was an orange colour with slutty red gloss lipstick. She fixed my blonde hair up and attached the little hat, and scarf.

And for a final touch she fetched my red shoes.




When I emerged, there was an amazing racket as all the girls and Cameron the co-pilot went nuts. Kathy had done a great job. Ursula was sat with the wine looking very drunk.




But the most noticeable thing was Cameron's eyes they were fixated on me. His intense stare startled me! I think the girls must have noticed it as well because they all cooed.




"Truth!" Ursula gasped the girls giggled.




"When was your last orgasm?" the giggling was incessant now!




"Six, no seven months ago!" she shouted the others gasped, and I noticed one of them wink in my direction.




Several minutes later it was my turn again.

"Dare, no truth" I hesitated.




"Ah we need to take your first answer." They seemed to say in unison.




They went into a huddle except for the semi naked Ursula, who was standing over me bottle of wine in hand. No need for glasses at this party. She was about 6-foot-tall and a real woman's build perhaps a size 14 or 16 and she looked good for it. She had large boobs and they still looked small on her.

Her skin was olive tanned, and she had long black hair that had been rolled into a bun high on her head. Her olive-green eyes seemed to shine in her drunkenness.




"Ok we want you to give Ursula what she needs most in the world!" I looked at them they were all grinning and when I looked at Ursula she winked.




As I was dressed in her clothes, she had been standing in her orange satin panties, and black bra. I felt her grab my head and shove my egger face into her groin.




Her musky scent was almost overpowering, my nose was pressed into her gusset her hands pulling me closer to her. I stuck out my tongue and I was amazed that I could feel her wetness through the satin. I began to nuzzle into her crotch. I heard her moan, this spurred me on.





I slipped my manicured fingers between her legs and moved aside her thong and into her soaking pussy.




This drew out a louder sigh. I began to slowly finger fuck her pussy while chewing through her underwear.





After a while of this she pushed my head back and pulled down her panties stepping out of them and tossing them to Cameron. As I followed them fly through the air, I noticed that he had out his massive cock and was gently stroking it.





The other girls were sitting with their skirts hiked up and were rubbing their clits. 

No sooner had I seen this fantastically horny image, than my head was yanked back towards Ursula's hot wet hairy fanny. I sucked her clitty into my hungry mouth and began flicking it with my tongue and I slipped a couple of fingers into her pussy and my thumb into her tight arse hole.




She began to grind into my face and fingers; she was still standing above squatting almost onto my awaiting face. She moaned and then her knees buckled! Her tummy muscles contracted, and her ass closed around my thumb. It nearly broke my neck, but she was cumming hard. She slipped in a post orgasmic daze onto the floor in front of me. A kind of glazed look on her face! I noticed that she had a very liquid cum. To be honest if I didn't know any better, she looked like she was pissing herself.



I looked around me my head a horny blur and my aching cock tucked between my legs and hard. I caught a glimpse of Cameron. He had wrapped Ursula's panties around his massive black cock and was wanking furiously.




"Can I help?" I asked not waiting for an answer, I stood and stepped across the aisle to the co-pilot. I placed my lips on his and it seemed to take him a moment or two before he opened his mouth and I felt his tongue enter my own.

We kissed for a short time exploring each other's mouths, before I reached down and took his manhood in my hand. I'm not a small person, but my fingers just about reached around his tool.

It wasn't the longest dick I have ever encountered, maybe only 6 inches, which as it happens is slightly shorter than mine. But he was thick! Maybe three times the girth I was sporting.

I broke the kiss and slipped to my knees, I was never going to be able to get this into my mouth, well not all of it anyway. But I was going to have fun trying.

I unwrapped Ursula's discarded orange satin thong from his cock and tossed them towards one of the other hostesses. Kathy caught them and instinctively brought them to her face, where she breathed in the mixture of Ursula's and Cameron's musky scents.

The other hostess gave her a quizzical look and drew down her own underwear, this time a rather boring pair of white cotton panties. She passed them to her colleague, who repeated the sniff on her knickers. A satisfied moan escaped her lips, before she slipped out of her seat, positioned herself between the legs of her now commando co-worker, and within seconds of the cunnylingus commencing she was groaning out her wholehearted approval of her colleagues' oral ministrations.

I watched the two while giving gentle licks to Cameron's delicious cock. I tried to open my mouth wide enough to suck him in, but it was never going to happen, well not without unfortunate teeth versus cock consequences.

He gently took my face in his big hands, and said, "Thank you for trying baby, but I'm too big for oral or anal." He shrugged his shoulders, disappointed.

I could see Ursula regain some amount of self-control, she climbed to her feet. Except for her black bra. She was naked, she unfastened her black wonder bra letting it drop to the floor. Her lovely c cup breasts were still full of life and firmness.

She approached us and looked down at Cameron's cock.

She said, "I'm sure his fagot ass can take that. I will just lube you up first."

With that she squatted over the co-pilot and lowered her soaking wet fanny down on to him.

A deep moan echoed out of her as he filled her up.

"Fuck you're big, she screamed." Sinking along his length. All her breath rushed out of her with a groan as her ass met his crotch. He was all the way inside her.

I gave Ursula an impressed look. "Three Children." She smiled back at me.

But she didn't have the stamina to begin to fuck him in any earnest. She managed to climb up along his cock and drop back down only a few times before her knees gave way. And she climbed off him one last time.

The panty sniffer hostess had left the confines of her co-workers soaking lap, she stepped over to us and produced a tube of KY Jelly. I glanced at her quizzically,

"What?" Kathy protested, I did not relent, I wanted an answer.

"My boyfriend likes me to fuck him with my strap on, and he is picking me up at the terminal."

"He is a lucky guy." I Smiled taking the lube.

She replied, "Nope I think you're about to get lucky." As I lay myself down on the countertop in the first-class bar on the top deck of the A380 aircraft, I pulled my skirt up over my waist, and moved my silken underwear to the side. Liberally I applied the lube. Cameron approached me cock first.

He was just going to try and jam that thing into me. "I don't think so, you don't touch me with that until my ass is ready for it."

Smiling he said, "So you want me to get you ready for my cock?"

"Well it's not going to lubricate itself now is it?" I hinted.

Beside me the hostess without the knickers asked the Kathy, "What about the dildo?"

"What do you mean?" Kathy answered.

"Do you have it with you?" she playfully asked.

"Why yes, I do, do you want to see it? Kathy asked.

The commando hostess shook her and puller her skirt over her waist and bent over one of the chairs and said, "I'd much rather you fucked me with it."

Within minutes she was getting properly fucked from behind by Kathy and her massive purple jelly Jay-shaped dildo. The two women were howling in pleasure.

Cameron had two fingers deep inside my ass losing me up, and Ursula was giving me a very pleasant sloppy blow job.

Funny something had taken my mind off just how nervous I was about flying.

Soon Cameron's two fingers became four and I think I was ready. He sensed it, pulling his big digits out of my hole, before he could do anything Ursula grasped his hand and sucked the fingers that were just inside me.

More lube was applied, lots more.

I was ready. Cameron edged his thick cock closer to my opening. I could feel him press against me, I pulled my cheeks as wide apart as I could and braced for it.

Instead of the pain I was expecting I felt full. I have had a very active sex life. This wasn't the first time I have bottomed; it wasn't even the biggest dick I have ever ridden.

I felt a sense of achievement in taking such a massive cock, especially after he claimed that he could not have anal sex.

"I sure showed him." I thought, before he startled me by saying.

"Ok I am going to put it in now."

"What the fuck, was in me." I thought. I felt like I had given birth, but the baby was crawling back into me. It was just the tip. My eyes watered, my ass ached, and my jaw slammed shut as for the next three minutes he eased more of his manhood inside of me.

Every centimetre he paused allowed me to get used to him or adding more lube. Before gently pushing more into me.

Ursula sensed my anxiety and she took my mind off the pain I was feeling, she climbed onto my lap and slipping my fully erect slender six-and-a-half-inch clit into her pussy. Her impressive tits bounced as she rode me like a rodeo bull.

After a few more minutes, I felt the most amazing pleasure. My ass had become used to Cameron's dick, and it was starting to enjoy its presence there.

I felt him pull out and slide back in, patience was giving way to frustration, to lust and to the need to breed my ass. His pace was building, he was breathing harder and harder.

On my own cock Ursula was bringing herself off again. She wasn't riding as frantically now, but she had found her sweet spot, and was using my cock to massage it while she excitedly rubbed her clit.

Beside us two awesome looking women where fucking each other with a strap on. Every one of my sexual senses was being aroused, and I was about to experience my first ever multiple orgasm!

I was on the verge of a complete sissygasm from the best ass fucking I have ever been on the receiving end of.

I was on the precipice of a mental orgasm watching and listening to the two beautiful women beside me fuck each other senseless.

Ursula was riding me toward my first pussy orgasm in months.

"Oh My god. I'm gonna cum." I managed to say, just as Ursula shouted, "Fuck, I'm cumming."

Cameron urgently screamed, "Bitch I'm cumming!"

For an instant, I felt nothing.

I saw nothing.

I heard nothing.

Then the blinding white light and a deafening roar as every sensory nerve ending exploded.

People talking about their orgasms building from their feet. This didn't build up to an ultimate climax.

This erupted out of every cell in my body, every synapse in my mind.

I didn't just cum, I CAME!

When my vision returned to normal, and my breathing and heart rate steadied. I noticed that all four of my mid-air fuck buddies were staring at me.

They seemed concerned.

"Wow." Was all I could muster.

The five of us met a few times over the next couple of months, and while the sex was always mind blowing, it never seemed to get to the same intensity.

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