The Friendly Skies

Chris arrived at the airport late, leaving twenty minutes to get checked in, go through security, and find his gate to board the plane. He hadn’t planned on being late, but Anna’s surprise visit was filled with her crocodile tears, begging him for forgiveness and endless promises that she’d never cheat again. He wasn’t interested in getting back together with her, but calming her down took time, and this put him behind schedule.

The agent at the front desk saw that Chris was running late, so he managed to check him through quickly and called the gate to let them know he’d be there shortly. The security check was remarkably quick, and 15 minutes later, Chris had boarded the plane and was walking down the aisle towards his seat. He found his row and put his carry-on in the compartment above his seat. He usually requested a window seat because he rarely had to get up during a flight, and he was looking forward to watching San Francisco fade away, leaving Anna – and her multitude of issues – behind him. Once he stored his gear, he noticed there was already someone in the window seat. The lithe brunette had her head down, focused on her phone as her thumbs worked the keyboard.

Chris cleared his throat, and said, “Excuse me, but I think that’s my seat.”

The brunette kept typing, not acknowledging Chris’ presence. Eventually, she replied, “I know I’m supposed to have the middle seat, but would you mind switching? I’m already set up and comfortable here.”

Chris had already had more than enough arguments for the day, so he said nothing. The man sitting in by the aisle moved his knees so Chris could get by to take his seat.

“Ma’am, you’ll need to turn off your device before we take off,” said the petite flight attendant, her red hair tucked into a neat bun. The brunette sighed loudly and made a big show of turning off the device. The flight attendant thanked her, gave the three of them a polite smile, and proceeded to check on the rest of the passengers. As soon as she’d moved a few rows ahead, the brunette took the phone out and began texting again.

This was an indicator of how the rest of the flight to Maui would be. The brunette turned out to be an entitled little bitch, demanding drinks from the flight crew, complaining about the meals and service, and regularly disrupting Chris and the other man so she could “stretch her legs.”

On one of her many trips to the lavatory, the man in the aisle seat told Chris about the brunette’s attempt to be upgraded.

“It was pretty funny. She’s pretty hot, so I noticed her while we were waiting by the gate. She was all sugar and sweet to everyone, especially the flight crew. I overheard her asking if there was any chance she could be bumped to business class for free. The person at the gate told her she didn’t think it was possible, but the onboard flight crew would give her the final answer. Once she was on the plane, she started to lay it on thick. ‘Oh, your outfit is so cute – that color really looks good on you’ and ‘I’d love to be a stewardess, y’all do such an important job.’ As soon as she found out she wasn’t going to get bumped, she became the little darling you see now.”

The flight attendant was beginning to get frustrated with the brunette’s demands for free drinks, free blankets, and generally anything she felt entitled to. Each time she responded to the buzzer, Chris gave the cute attendant an apologetic look, and she politely smiled back.

Once he’d had enough of the terrible music spilling out of the princess’ headphones, loud enough for him to hear while watching his movie, he got up to use the lavatory. As he made his way to the back of the plane, he saw the attendant preparing the cart for its next round. She was wearing the typical uniform for this airline, a light blue skirt, white blouse under a blue jacket, and a white and blue neckerchief neatly tied into an ornate bow. According to the badge on her chest, her name was Cara. Despite being a uniform, it hugged her form nicely, giving Chris a hint of the sexy body beneath the fabric.

“Is everything OK with your partner, sir?” she asked him.

Chris gave her a puzzled look and then realized what she meant. “Do you mean the little princess beside me? No – we’re not traveling together. This was my first – and hopefully last – time meeting her.”

The flight attendant gave him a knowing smile, and asked if there was anything she could help him with.

“I just needed a moment away from her. It’s a long flight, but I guess I don’t need to tell you that. I hope you don’t have people like her on every flight.”

“Not quite like her, but there’s usually someone like that. It’s ok – I like pretty much everyone,” she replied.

“Would you like a drink?” she asked.

“Actually, given the day I’ve had, yes. I’d love a double rum and coke, but I left my wallet at my seat. I’ll have to get it the next time you come around.”

She reached into her cart and mixed him the drink, handing it to him as she said, “If someone else were sitting beside her, I’m sure the level of drama would have been through the roof already. This one’s on me.”

“Thanks for this. Not gonna lie, this is the best thing that’s happened to me in the past few weeks. I booked this flight a few months ago to spend some time on the beach with my girlfriend. Unfortunately, I found out last week that she’s been screwing my next door neighbor. I managed to get her ticket refunded, so I guess it’s my fault the princess is sitting beside me. Oh well – another few hours and I’ll be on the beach in Kihei, sipping a Mai Tai and watching that gorgeous sunset.”

They chatted a bit longer, and then Cara excused herself to do her rounds.

Chris went back to his seat and tried to enjoy the rest of the flight.


There was a knock at the door and Chris jumped to his feet, hoping it was the airline with his missing luggage. He’d spent 45 minutes at the carousel, waiting for his bag to arrive, but it never did. After a quick stop at the airline’s counter, he learned that because he’d checked in to his flight so late, it didn’t get put on his plane. Instead, it was loaded onto the next flight heading to OGG, but they’d deliver it to him when it arrived.

Chris opened the door and was surprised to see Cara standing at the door of the condo with his suitcase. She had changed out of her uniform and was wearing a white t-shirt and boy shorts. Chris could see her colorful bikini top under her shirt, and he was surprised at how full it was. Her uniform certainly didn’t do her justice.

“Hey Cara – thanks for bringing this, but you really didn’t have to go to that much trouble.”

“Well, since I knew you were going to be spending the week alone, and I’m only in town for the night, I thought maybe I could help you take your mind off your troubles.”

And with that, she reached her arm up and Chris felt her hand on the back of his neck as she pulled his lips to hers. They kissed, and she could taste the rum on his breath. The slight sweetness was far from unpleasant.
Cara broke the kiss and stepped back. Her cheeks flushed and she was breathing quickly. She closed the front door and locked it, then took Chris by the hand as she went looking for the bedroom.

“Don’t get the wrong idea – I don’t do hookups often, but I thought you were really sweet and cute, and, well, it’s been a while since I’ve had any real fun.”
Chris was wordless; he wasn’t going to say anything that might fuck this up.

Cara found the bedroom and sat Chris on the edge of the bed. She pulled out her phone and a few moments later the sounds of AC/DC filled the room and she started to groove along to the beat.

She ran her hands along her lithe frame, her fingers exploring her sensitive skin, goosebumps rising as she teased herself. As the music sped up, she slipped the t-shirt over her head, tossing it at Chris as she giggled. She danced towards him, bending her neck slightly to catch his lips with hers. Chris ran his fingers over her soft skin as they kissed; her tongue teasing his, sucking it into her mouth.

Chris undid the bows of her bikini top, letting it fall to the floor. He slid his hand from her back, feeling the slight bumps of her ribs as he moved closer around her chest. He felt the swell of her breast, and she gave a little gasp when he found her hard nipple. He kissed down her neck, enjoying the smell of her perfume and perspiration. After a few minutes of sucking her nipples and playing with the warm flesh of her breast, he reached a hand down to her thighs, feeling the soft flesh below the hem of her shorts. He moved his hand further up, feeling the light fabric against his skin, and her heat beneath it. He started to rub her through the shorts, feeling her push back at him, grinding her pussy against his hand.

Cara pulled away from him, stepping back to catch her breath. She puffed a strand of loose hair away from her face, locking eyes with Chris as he sat on the bed. She undid the snap on the front of her shorts, and in an instant, they were laying on the floor beside her bikini top. She moved back to Chris, pushing him down so he was lying on his back, and then gave him a quick kiss before wriggling her way up his body to straddle his head. She leaned forward to brace herself, and Chris dove face-first into her gorgeous pussy.

He started licking her outer lips, enjoying the sweet taste of her juices. He grabbed her ass with both hands, massaging her as he licked. She moaned regularly, loving the attention he was putting on her sensitive spots. He slowly licked up and down, be sure to hit her swollen clit on every upstroke. As her juices began to flow, Chris focused his attention directly on her clit, sucking it into his mouth and caressing it with his tongue. Cara responded by bucking against his face, but Chris held her firmly in place so she could enjoy the ride.

Chris kept working on Cara’s orgasm, and as he felt her building up to it – her body arching towards him, muscles taught and clenched – he pinched her nipples gently, pulling them slightly to trigger her orgasm. And it worked.
Cara rocked hard against Chris’ tongue as the waves of pleasure overtook her. He continued to lick and suck as she started to tremble, but the sensation was too much. Her body was always sensitive immediately after she came, and now it was her turn to pleasure him.

Cara pulled away from Chris, sliding down his body until she could feel his hard cock through the fabric of his shorts. She undid his belt and slipped them off of him, giggling as his cock sprung free like a jack-in-the-box.

“Oh, that looks delicious. It’s the quiet guys that always have the biggest dicks,” she said, making him blush.

And then she inhaled his cock, taking his full length into her throat. He resisted the urge to fuck her face, allowing her to do what she obviously knew how to do. She pulled back and began stroking his cock with one hand, the other caressing his balls, and then took him in her mouth again.

Chris was in heaven; a gorgeous redhead looking up at him with a mouthful of his cock. Her stretched lips were smiling as she sucked, and he knew he wouldn’t last long with this much attention on him.

He took her by the shoulders, and they both laughed at the slight pop as his dick came out of her mouth. He lifted her off the bed, placing her just above his glistening cock. She took it in her hands, and guided it inside her, lightly rubbing his head along her slit before slowly sliding him into her. Cara chose the pace, rocking up and down in tune with the music. Chris wished a slow song would start playing, as he was dangerously close to the edge, but when the next some game on, Cara started moving even faster.

She was in the zone, and was nearing another orgasm when Chris said, “Slow done, I’m gonna cum.”

This just made Cara move faster. As she bounced up and down on his hard shaft, she used her internal muscles to gently massage his throbbing cock. A second later, she felt him tense his body, and then she felt him release deep inside her. The blasts of cum pushed her over the edge, and she started cumming along with him.

They collapsed into a sweaty heap, and as they drifted off to sleep, Cara whispered, “Sorry this was just for the one night, but it was damn nice to meetcha, Chris.”