Mile High Luck

Chapter 1

The fleet manager boarded his flight after a long delay. For compensation they bumped him into first class, which was the least the airline could do. It was a red-eye flight, so even the coach section was pretty empty. There were only six other people in the first class section. All were lounging in the comfortable leatherback seats, with lots of foot room, programming Internet, movies or music onto their personal viewing screen. He put his carry-on bag in the large overhead compartment and got settled. The seat next to him was vacant upon take off.

The pilot made his regular introductions over the intercom, and then the flight attendants did their safety speel. The fleet manager noticed how attractive the stewardess was in his section. He noticed the top 2 buttons of her white blouse were undone and she was wearing a navy lace push up bra. The only accessories she wore were a small brooch, resembling golden wings, and a blue silk scarf tied around her neck. The navy skirt she wore was sexy, and short, with a slit up the side, but not slutty. She wore a pair of high-heeled dress boots, which hugged her muscular calves. He liked the way she ran her fingers up the oxygen tube when she was demonstrating safety precautions. She was giggling and winked at him, as she acted out all of the motions.

That's what he loved about this airline's stewardesses. They were all good-humoured and laid back. And most of them were very attractive and attentive in meeting their customer's needs. Besides who could resist a woman in uniform, with the reputation of initiating passengers to the Mile High Club?

As take-off was approaching the sexy stewardess buckled herself into the designated attendant rest area next to the gentleman. After acceleration and achieving the maintained flight pattern, the auburn-haired stewardess rose from her seat and came around with the cocktail and dinner menus. When she returned, she took his order of a bottle of wine, and the dinner feature.

He proceeded to eat his meal and have a couple of glasses of red. After checking on the other passengers, the stewardess came by and asked if everything was to his satisfaction. He asked her to sample the red wine. She winked and mentioned that she preferred scotch. A nice, smooth, relaxing drink. He asked her what she recommended, and she brought him a bottle.

The traveler asked for a glass of ice, and once again the sexy stewardess came over to make sure his needs were being met. They shared a glass, and poured another as she sat down beside him to rest. The lights were dimmed and most travelers were sleeping, taking advantage of the extra space to stretch out. There was a bit of a draft, so he asked for a blanket and pillow to curl up with. She stood up and went into the overhead compartment next to the lavatory. As she reached up, her skirt and blouse rode up a little, and the gentleman caught a brief glimpse of her bare midriff and upper thighs. She returned with the items. He noticed she brought an extra blanket as well.

Being sky high always made the gentleman horny. It could have been a result of the altitude, the pressurized cabin, the turbulence or the flirty flight attendants. Who knows? All he knew was that he was starting to get an erection. He wondered how many people actually get off during a flight, underneath the privacy the blankets provided.

She passed the items to him, as they each got comfortable under the warmth of the covers. He poured the two of them another dram of scotch and made small talk as the other passengers slept. Once the drink was done, the gentleman propped up his pillow and turned towards the window. He brought the blanket under his chin and tried to drift off for a nap. The stewardess flipped through a magazine until she too became sleepy. Her eyes closed.

When he thought she was asleep, the fleet manager undid his pants and began to stroke his firm cock. He slid is thumb underneath the rim of his purple head and squeezed. Precum was beginning to seep out of the tip. He continued slowly at first, enjoying the build up, knowing he was jerking off next to a beautiful woman. He could get caught, but that added to his excitement. He fisted his cock with one hand and began to cup his balls with the other. He tried to maintain discreet strokes so he wouldn't bring attention to himself while she was snoozing. He had to fight to keep his breathing quiet and relaxed. It was kind of like edging. He fantasized about fucking the sexy little stewardess beside him. He couldn't fully indulge in a big stroke-off session, but the restraint and resistance he had to demonstrate was even more arousing.

He wasn't sure at first, but he thought he sensed movement from beside him. He slowed his pace and shortened his strokes so he could hear. He swore he could hear the wet, smacking sounds of the flight attendant's fingers playing with her hot pussy.

The stewardess did in fact know exactly what the traveler was doing. She was not asleep, and watching him made her extremely horny. She pressed her thighs together and felt her clit swell. She decided to perform a little parallel play of her own, beside him. Underneath the blanket, her fingers pushed the crotch of her panties to one side. She hiked her skirt up a bit so she could spread her legs slightly. As she listened to his ragged breathing, her thumb flicked the tip of her clit, and her fingers explored her pussy lips. She was already dripping, eager to address her sexual energy. Her fingers slid back and forth across her pussy. Every so often she would insert her middle finger and diddle inside a little, lubing her fingers and pussy without full penetration. She worked herself up until she couldn't help but to thrust two fingers inside her clenching cunt. She worked herself hard, gyrating her hips. At this point, she didn't care if the stranger beside her knew what she was doing. In fact, she wanted the gentleman to know. And he did.

They turned towards each other and lifted the armrest between them. The flight attendant reached under the traveler's blanket and replaced his hand with hers, stroking his rigid manhood, feeling the engorged veins against her palm. The fleet manager groaned softly and reached over to feel how wet she was. His fingers slipped easily inside her soft skinned slit. Her fist tightened around his swollen, shaven cock and she quickened her pace. He fingered her faster and with full force. She knew she was going to cum all over him, and from the expression on his face she could tell he wasn't far away from blowing his load, either.

The gentleman began to feel the tingling pressure build up in his cock. His balls tightened, and he could feel a throbbing begin to surge forward and upward, growing more intense. The flight attendant stopped what she was doing and led him by the wrist to the first class lavatory, behind the curtain at the front of the plane. Once inside, she switched the lock over to occupied, and the no smoking sign overhead lit up. "There's no sign saying 'No Sex'", she thought, laughing to herself. The flight attendant embraced the gentleman, grabbing his ass, and pulled him to her. She pressed her tits and hips against him, and felt his penis push back against her. She took a step forward, leaving no option for the man but to sit down on the covered lavatory seat. She pushed his pants down around his ankles and hiked her skirt up to her waist, removed her panties and straddled him. She deliberately plunged herself down onto his stiff, smooth rod. She bucked forward, slowly and forcefully, sending him deeper inside her moist cunt, and then lifted herself up from his shaft pausing a few moments between each downward motion, allowing the tip of his cock to tease her sensitive clit.

He too was being teased. He wanted nothing more but to fuck this horny little stewardess fast and hard. He'd already been worked up to a frenzy when she was giving him a handjob, and his balls were aching to explode his hot cum inside of her.

The sexy stewardess continued to ride him. She increased her pace as she bounced up and down. She opened her blouse and removed her bra so she could play with her nipples as he watched. Her scarf hung sexily between her breasts. She tried to spread her legs wider, but the space was cramped. Her knees kept hitting the sides of the sink and opposite wall. Thump, thnk, Thump, thnk...She was hoping the passengers would sleep through the entire racket they were causing.

Finally, the Fleet Manager positioned the flight attendants legs up and over his shoulders. He liked the cool feel of her leather boots against his hot body. He licked her calves, where the rim of the boots hugged her skin. She arched back with her hands on the floor behind her. She had great thrusting power from this position, and he had a perfect view of her tight little twat swallowing his meat. Not to mention, it was perfect placement for a g-spot orgasm!

The traveler grabbed her ass and plunged up into her as he pulled her down against his hips. He fucked her with his raging cock, and she felt him pound into her pussy, hearing her juices squish and smack with every thrust. He watched his cock disappear into her depths, re-emerging, coated with her honey. He played with her clit with his thumb, and felt it harden against the tips of his fingers. She began to grind against his hand as she fucked him. The sheer pleasure of being filled with his perfect cock combined with his massaging fingers on her own clitoral erection was more than she could take. She wanted him to fuck her hard, fuck her deep and fuck her fast ...NOW! Her sopping wet cunt was quivering, her legs began to convulse as he rammed her full of his massive love muscle. Each powerful thrust stimulated her g-spot just right.

"God, yeah, fuck me, it feels so good right there! Your cock's gonna make me gush!"

Upon hearing this, the traveler could hold back no longer. He shoved his manhood inside of her, three more times and on the third he fucked her so deep and hard he felt her pussy clenching and gushing all over his hot exploding cock. He shot off deep inside of her, creaming her good. It was just about time for her to make her rounds and check on the other passengers. She stood up, and he pulled his exhausted muscle from her tenderized pussy. As he did, white strings of his hot cum mixed with her fluids, seeped down her thighs. She took a couple of the complimentary wet wipes to clean them both up. They washed and were still pretty shaky before leaving the lavatory at separate times. The stewardess smoothed down her skirt, buttoned her blouse, and reapplied her lip-gloss. Just before she left, she pinned the golden wings onto the gentleman's shirt.

The fleet manager inquired about the length of the flight. Two more hours. He found out that the flight attendant was stopping over for two days to stay with her twin sister who was also in the travel and tourism industry. As luck would have it, the sexy stewardess' sister was a chambermaid in the same posh hotel the traveler was booked to stay at! He felt like he had won the lottery! For the next two hours, he fantasized about the two women, watching them, joining in with them, being sandwiched between their voluptuous bodies.

Chapter 2 The traveler always imagined how beautiful it would be watching two sexy, horny women play together. He never dreamed it could potentially become a reality! Before departing the aircraft, the fleet manager and the stewardess made plans to meet in the hotel nightclub later that evening after the business of the day. She had mentioned that her sister might be working in the bar to make extra cash to supplement her chambermaid wages.

The hotel was innovatively designed, offered a variety of nightly entertainment for business travelers and all rooms were executive suites with huge comfy king sized beds. And of course, the service was outstanding...

The fleet manager checked in and went up to his assigned room, 369. The first thing he did was check out the massive bed. Big, fluffy pillows were propped against the headboard. The mattress was a pillow top and the sheets were soft as silk. He looked around the room. There was a big 32-inch television, with an advertisement placed on top for pay TV movies. There was a good sized bar fridge and a cozy sitting area in front of the gas fireplace. Very nice, he thought as he wandered over to the bar fridge. Inside, it was fully stocked with a range of beverages. Above the fridge was a mini bar, with different types of glasses, cognac, scotch, brandy and various liquors. Fruit, chocolate, cheese and crackers were also provided.

The gentleman dropped some ice into a short whiskey glass and poured himself some of the Hennessy XO cognac. He had some time to kill, and was still horny from the flight, so he took a sip of the smooth warm cognac, and decided to shower. As he soaped up his body, he could still smell the lingering perfume and scent of sex on his body. His anticipation about this evening was growing, as was his erection. He soaped up his hands and started to stroke his semi-hard shaft as he imagined the two women making love to each other as he watched. He visualized their bare tits pressing against each other, touching each other's hips and thighs as they kissed passionately. He pictured them with their long sexy legs entwined as they rubbed their slick pussies in tandem. He continued with his slow, erotic jerk-off. His cock was hard now. He knew he'd better not give in to his urge to come. He had to save his energy for the evening, if he was lucky! He would prefer if it didn't come down to manual labour with Mighty Righty in his tighty whiteys tonight. He played with his cock a little more, and then continued to lather up the rest of his body. The hot water felt so good. When he was squeaky clean, he stepped out of the shower and reached for one of the huge fluffy white hotel towels and headed to the bar to make himself another drink. He leisurely got dressed, pausing every now and again to rub and tease his cock. When he finished his drink, he grabbed the cardkey and went down to the club.

The bar was busier than he thought it would be. It was like a classy Cowboys on a smaller scale. The DJ played a mix of country, Latin, techno and hip-hop. The waitresses all had perfectly round tits and pierced navels. The bartenders were sexy in their black tees, jeans and cowboy hats. The shooter girls looked hot in their black tight tank tops, denim skirts and holsters. The music was loud and the atmosphere was lively. The fleet manager enjoyed the freedom of being a stranger in a big city. He ordered a drink and stood by the dance floor and watched as he waited for the stewardess and her twin to show up.

He watched as one of the shooter girls made her rounds. She was across the dance floor from where he stood. She had auburn hair and a pair of tits so round and firm and a delicious looking ass. She offered men shots of Tequila, Jack Daniels or Sambuca. If the guy tipped big, she would place the glass between her voluptuous breasts, hike up her denim skirt and straddle him as she sat in his lap, before taking the bottle out of her holster and pouring it slowly into the glass. She would then perform a mini lap dance as the guy took the shot from between her tits and swallowed.

The fleet manager thought he could probably use a shot to relax his nerves. He had the expectation of a threesome tonight, but perhaps the stewardess' twin wouldn't be in to it. He had to be prepared for either scenario and play it cool. He pulled out his wallet and a 20-dollar bill to get her attention. As she made her way through the crowds, towards him, he noticed the striking resemblance to the sexy stewardess he had just fucked hours ago. It was her twin! They had the same sinful lips, dark eyes and auburn hair. The only apparent difference was the size and shape of their breasts. The stewardess was 'au natural', while he figured the shooter girl probably had a boob job to help boost tips and sales.

"What'll it be, Cowboy?"

He gave her the twenty and she poured him tequila. She danced in his lap, and rubbed her hot crotch in circles against his. He buried his face in her chest, licked the valley between her tits and took the drink. She felt his hardness grow against her.

As the lap dance ended, the fleet manager stood up and the stewardess approached him from behind, embracing him and pressing her firm breasts against his back. She slapped his ass. "Hey, Stranger!" She smiled.

"Are you referring to me or him?" The shooter girl came around and gave her sister a huge hug and kiss on the lips.

"Hey sweetie! Long time no see!" the stewardess laughed.

"Is this the anonymous traveler you were telling me about? He's hot! And I'm off in an hour", called the shootergirl as she sauntered off to her next waiting customer.

The fleet manager felt his face flush. So the two sisters had already spoken. He wondered what the night would offer. He bought the stewardess a drink and they talked a little before heading out on to the dance floor.

The dance floor was packed. Hot, sweaty, dancing bodies were everywhere. Everyone was into their own groove, and there were a lot of couples doing their own versions of dirty dancing.

The sexy stewardess pressed her body against his as they danced. She swayed her hips and touched her lower belly seductively. This little hottie had all the moves. She twisted down, hiking her skirt up slightly. He caught a brief glimpse of her bare, pantiless pussy. As she moved back up, she pressed her body against his, stopping to grind against him for a few beats. They continued to dance; the fleet manager followed her lead, enticing her with his own dirty dancing. He brought her to him and spun her around 180. He slid his hands along the side of her body, feeling the curve of her breasts, and continued down to her hips. She thrust her ass out slightly and wiggled it to the rhythm of the music. He gyrated his hips forward and back to the beat. She felt his hardness. He reached around to her belly and pulled her back against him. He pressed his cock against her hot ass as they danced and moved to the music. As the techno beat got faster, the two of them became lost in their own arousal.

"Mind if I join in?" Shootergirl asked. "I'm off for the rest of the night".

She came around behind the fleet manager and draped her arms around his shoulders as she rubbed her pelvis against his butt. "How about midnight snacks and sandwiches, later?" She suggested.

Again, he couldn't believe his luck! No manual labour tonight! Threes were usually unlucky for him. Not so, anymore! The shooter girl turned out to be just as horny and eager as the stewardess. The threesome continued to hump and grind against each other as they danced. Sometimes the two girls would dance together seductively as the fleet manager watched. The sexy little stewardess raised one leg and wrapped it around her sister's ass as she rubbed herself against the twin's hips. They thrust their pelvises together, as they touched each other's hot and sweaty bodies. It was a huge turn-on for the gentleman. His cock felt like bursting. He'd been in a constant state of horniness since he boarded the plane late last night.

Not wanting to wait any longer, he initiated going up to his room for drinks and continuing the evening up there. Obviously the girls didn't need much convincing, so they all headed up to room 369.

Chapter 3

Upon entering his room, the fleet manager offered the ladies drinks and poured one for himself. He expected awkwardness, but there was none. The two sisters got up on the king-sized bed. They noticed the Pay TV brochure and suggested ordering a porn. Well, the fleet manager needed no convincing either, so he got it set up and joined the two of them on the bed.