Wingman

by RejectReality

Copyright© 2019 by RejectReality

Erotica Sex Story: Amelia has always had a pilot fantasy, and she stays in airport hotels whenever she has the chance - always hoping. So far, she's had no luck. When a handsome pair of pilots buy her a drink, she's hoping at least one of them isn't a jackass, so she can fulfill her fantasy at last. She doesn't realize that her fantasy is about to get upgraded to first class with double rewards.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Mult   Consensual   Heterosexual   Fiction   Group Sex   Anal Sex   Double Penetration   Oral Sex   .

It had been a long, tedious meeting, broken by bouts of frustration. Fortunately, it had ended well all the same. Amelia checked her face and long, brown hair in the makeup mirror of her rental car, and decided she was still sufficiently presentable to have a drink in the hotel bar.

A drink she desperately needed.

Upon walking into the place, she saw the bar area was rather crowded. Worse still, most of the patrons there looked to be middle-aged businessmen, who were probably on the prowl, cheating on their wives. That was one of the drawbacks of staying at an airport hotel. There were always lots of businessmen hoping for that exotic one night stand while they were away from home.

Amelia found a booth in the corner, caught the attention of one of the servers, and soon had her drink in hand. The booze did a great deal to relax her, and let her forget the contentious points between the boring presentations she’d been subjected to all day. By the time her drink was nearly gone, she’d almost developed a positive outlook on life again.

The server walked up and placed a second glass on the table. Amelia winced, because she’d noticed one of the middle-aged lechers at the bar drooling over her for the last several minutes. When she looked up, the woman said, “From the fly-by boys over there. They said you looked like you could use some company, or at least another drink.”

She thought, Thank god it isn’t from knock-off Armani and fake Rolex at the bar.

The woman had pointed toward where her benefactors were, and Amelia steeled herself for disappointment. She had always harbored a fantasy about having sex with a pilot. The uniforms made her tingle all over, for some reason. It was why she always chose an airport hotel when the option was available.

Unfortunately, the closest she had ever come was an almost identical situation twice before. The pilots who had bought her drinks were older men, but it was the archaic lines and faux confidence bordering on crass that had turned her off. She’d have happily hopped in bed with a smooth, reasonably handsome, older man in a pilot uniform.

She turned toward where the waitress had pointed - already planning her thanks, but no thanks excuse to send back with the drink. That went out the window when she spotted two gorgeous men, about her age, decked out in full pilot regalia, with their hats sitting on the table. Pilots always seemed to keep part of their uniform, their hat, or something on their person to identify them. Pilot fantasies were common enough to be a minor trope, after all. The two men across the way looked as if they’d stepped straight out of the cockpit into their booth.

The pair raised their glasses in salute when they saw her looking. Amelia swallowed hard, smiled, picked up her fresh drink, and raised it in their direction. The men shared a quick look, picked up their hats, and started her way.

Amelia’s heart pattered in her chest. They absolutely looked delicious. She would have been happy to jump on either of them, and she had a choice. As long as they both didn’t turn out to be jackasses, she might finally be able to realize one of her deepest fantasies.

The two men reached her booth, and the first introduced himself. “Hey, I’m Will.” He then pointed at his friend.

“Charles.”

“Amelia,” she said, sending out the first signal that she might be interested.

Will said, “It looked like you could use some company, and it’s also a bit of a rescue mission.”

Amelia’s brow furrowed. “Hmm?”

Charles said, “Mr. Desperately Trying Not To Look Like Middle Management over there at the bar has been staring you down for about fifteen minutes.”

“And he is pissed at us right now,” Will said with laughter in his voice.

Amelia looked toward the bar and had to stifle laughter with her hand. Cheap Suit was absolutely staring daggers at the two men chatting with her.

She turned back to the two handsome pilots and said, “I noticed. Thank you.”

“At your service, Ma’am,” Charles said.

“So, interested in some company?” Will asked.

“Sure, why not,” Amelia answered. When the two men slid in the booth opposite to her, she gave them a sly smile and asked, “So, what do you two do for a living?”

They looked at each other and laughed. Charles plucked at his uniform jacket and said, “We’re charter pilots. This was a last minute call, right as we were about to go have some drinks. Decided not to wait once we got here. Dropped our bags in our room, and headed straight for the bar.”

Will added, “It’s the only chance we’ll have, really. We’re wheels up again tomorrow evening, and we have another scheduled flight the day after we get home.”

“I almost know the feeling,” Amelia said. “This is my third flight in the last two weeks.”

“Living in hotels can get to you. We’re from Chicago. How about you?” Will asked.

“Small world,” she said, and laughed. “I work in the city.”

That launched a conversation about home, which branched out into other topics, including several anecdotes about rich passengers the pair had ferried around the country. A message alert went off on Amelia’s phone while she was laughing at one such story, and when she checked it, she was shocked to see that almost two hours had passed.

“Something wrong?” Will asked, seeing the expression on her face.

Amelia waved her hand in a dismissive gesture. “No. I just didn’t realize what time it was.”

“Time for me to hit the men’s room,” Charles remarked. “Be right back.”

Amelia found she was at a loss. She’d assumed that one of them would stand out, or one would back off, letting his friend make a play for her. From their demeanor, she assumed they were both interested, and she’d certainly tried to send signals that she was.

The thing was, she didn’t have a single target for her flirtation. They were both good looking, charming, and witty. She felt as if she may as well toss a coin, and she’d come out a winner no matter which way it landed.

She almost reached for her drink out of habit, but stopped herself. Though she’d only finished about half of it, it was her third, and she was feeling it. She had a good buzz, and her inhibitions were practically in tatters.

To those ends, she decided to push a little harder. Will was the more talkative of the two, and she had him alone for a few minutes.

“If you’re trying to pick me up, one of you is going to have to try to outdo the other, you know?” she suggested.

Will looked surprised - though pleasantly so - at the directness. He said, “We could never do that. Chuck’s my wingman. One for all, and all for one.”

“Don’t you need three for that line to work?” she asked.

“It’s nice when it works out that way.” He paused for a moment, his gaze penetrating - searching. Then he sat up a little straighter, drew in a deep breath, and asked, “Want to be our third Musketeer tonight?”

Her train of thought - searching for her next line of banter - suddenly derailed when she realized what he was suggesting. She gasped as a chill shot through her, originating between her legs, where her intimate muscles clenched and a rush of wetness flooded her pussy.

Will asked, “Did I just blow it for both of us?”

“Not even close,” she answered in a voice husky with arousal.

He didn’t miss it, and smiled as he asked, “You want to head up to our room?”

Amelia shuddered and answered, “Oh my god - yes.”

Charles looked perplexed when he saw them sliding out of the booth as he returned from the bathroom. Will turned toward him, and some silent signal must have passed between them, because his eyes widened, and a smile sprouted on his face.

The moment he reached them, Amelia nodded toward the door, and then started toward it. Few people were out and about in the hotel, and many a lusty glance was exchanged as the three made their way to the elevators.

The moment the elevator doors closed, Amelia beckoned them with a waving index finger. They smiled, and put their pilot caps on, which stoked her fires even hotter.

It also freed their hands.

Will pulled her into a kiss, and Charles put his lips to work on the back of her neck. Their hands were everywhere in that brief ride, and Amelia’s found tantalizing evidence of muscle and big, hard cocks.

The three of them pulled apart, and Amelia pushed her skirt back into place when the elevator stopped. A minute later, Charles unlocked the door with his keycard, and all three swept into the room. Both men reached for their hats simultaneously.

“Leave them on,” Amelia asked.

They both stopped, smiled, and smartly settled their hats back in place. Instead, they went to work removing everything else.

As he whipped off his jacket, Charles suggested, “You could leave your heels on, if you want.”

Amelia nodded as she followed their example by quickly unbuttoning her top.

Clothing fell unceremoniously to the floor as the three of them hurried to undress. They all knew why they were there, and there was no sense in putting it off. The two men revealed sculpted, but not overly muscular chests - both shaved bare. Amelia shivered from their hungry stares when she removed her bra, and then moaned when Will dropped his pants. He had a big, gorgeous cock - larger than at least the last three men she’d had sex with, and that covered a couple of years. Charles proved he was a match for his fellow pilot only a moment later, when his cock sprang free.

The two seemed to be perfectly comfortable standing close to each other, buck naked and rock hard. The kiss of cool air on her sex as she dropped her panties testified to how wet she was.

Amelia stepped out of her panties, offered a sultry smile, and sauntered toward them in her heels. Charles climbed into the bed, moving toward the opposite side on his knees. Will held out a hand, and when she took it, he guided her into the bed as well. She couldn’t resist brushing her fingers over the brim of his hat.

Charles slipped his hand around her waist as she drew near, and she let him pull her into a kiss. The moment their lips met, she filled her hand with his hard cock. Will moved in behind her, swept aside the curtain of her hair, and put his lips to work on the back of her neck.

When Charles pulled away from the kiss, he groaned from the feeling of her hand sliding loosely over his erection. Then he cupped her cheek and turned her head toward his friend. She turned her body as well, so she could reach Will’s cock when he moved in to kiss her.

Charles dropped down, turned his head so he wouldn’t lose his hat in the process, and began to tongue her nipple. Amelia whimpered into her tongue-wrangling kiss with Will, and stroked both of them a little faster.

She was in absolute heaven. They were tantalizing her with their lips and tongues. She had a hard, ready cock in both hands. With their pilot hats on their heads, and the rest of their uniforms scattered on the floor nearby, she was living her fantasy in a way she never would have dared dream.

Will apparently couldn’t resist the call of her breasts. She had no reason to argue when his lips left hers, and instead engulfed her other nipple. Her hands roamed over their muscular backs as she looked down at them, breathing hard. Her breath caught for a moment when she felt Charles’ hand sliding up her leg. A high-pitched moan escaped her when he cupped her sex and caressed it with wiggling fingers.

Will released her nipple for a moment. His breath on the wetted nub made her shiver when he asked, “Have a bit of a pilot fantasy?”

“God yes,” she gasped.

“Happy to be of service, Ma’am,” Will said, and then chuckled before returning to suckle her nipple.

She groaned when Charles pushed two fingers into her needy pussy, and sucked her nipple hard. The thick digits stretched her, but slid easily into her slippery canal.

“How wet is she?” Will asked. He didn’t wait for an answer before kissing her hard.

Charles only opened his mouth around her nipple to answer, “Soaked.”

“Oh, ah, oh,” Amelia whimpered. Charles’ curled fingers had almost instantly found her g-spot, and the heel of his hand rolled her swollen clit. Both men grunted when the sensation caused her to tightly squeeze the cocks in her hands.

She let out a sad moan when the fingers inside her slipped free. She turned away from Will’s lips to beg Charles to put them back in, but saw him lifting the digits toward her lips. She sucked them in, shivering from the taste of her juices. Her eyes locked with Charles, and she slid her lips up and down his fingers, growing hungry for something far larger and more mouth-watering.

Will’s fingers replaced Charles’ in her pussy.

“Oh yes,” she cried as Will proved his fingers were every bit as dexterous and knowing as his friend’s. He put his other hand to good use, squeezing and fondling her breast.

Amelia luxuriated in their attention. They kissed, fondled, suckled, and fingered her until she was trembling. The hard cocks in her hands were calling to her the whole time, and she finally had to answer.

“Lie down,” she said to Charles, letting him see the hunger in her eyes. As soon as he sat down to eagerly follow that instruction, she turned to Will and licked her lips.

He nodded, smiled, and pulled his fingers out of her pussy. The slurping sound that made left little doubt of just how wet she was.

Charles was settling on a pillow in the center of the bed when she turned back toward him. She slowly bent over, turned around - wiggling her ass in invitation - and dropped onto her hands over his lap. She gave his cock a long, broad-tongued lick and moaned when his hand settled on her butt.

Will knelt down next to his fellow pilot, putting his cock within her reach, and proving once again that the two men were perfectly comfortable sharing a woman between them. She wrapped her fingers around both hard organs while her tongue glided over Charles’.

“Ah, fuck yeah,” Charles groaned when she parted her lips and took him in.

They were both stone hard and throbbing. Amelia loosely stroked both of their erections while slowly sucking on Charles. He ran his hand over her ass, and dragged his finger through the cleft between her buttocks. She whimpered around him when his finger tip circled the iris of her ass. Will ran his fingers through her hair, and then reached down to squeeze her breast.

She let Charles slip from her lips a few seconds later to tongue Will’s erection. Hands still moving up and down their hard organs, she wetted the tip, and then took him in.

Will groaned and said, “She’s got a hot little mouth, doesn’t she?”

“Hell yeah,” Charles agreed. Though the angle wasn’t perfect, he’d managed to reach her pussy with the tips of his fingers. His hips lifted for a moment in response to her hand. “Mastered dual wielding, too.”

Will chuckled at that - though the sound vanished in a grunt when Amelia gave him an especially hard suck. She only had the vaguest notion of what they were talking about, and didn’t really care. The scent of their manly musk combined with a burst of flavor when Will seeped a drop of pre-cum - making her feel light-headed. When she switched back to Charles’ cock, he provided her with a similar offering.

Amelia moaned and whimpered, switching back and forth between the two wonderful cocks, lost in the moment. The men voiced their pleasure, and demonstrated it with their roving hands, which seemed to be on every square inch of her body.

Aching for more, she was about to ask for it when she slurped her way back to the swollen head of Will’s cock. As if he’d read her mind, he was moving before she could say a word. While he knee-walked in behind her, she gasped, “Yes, please.”

Charles settled his hand on the back of her head when she took him in again. Her lips slid quickly up and down about half his length, while her hand stroked in counterpoint below. She shivered when Will traced the parting of her nether lips with the tip of his finger.

“Nice and wet,” he said, before slipping his finger in.

Amelia moaned and sucked hard on Charles’ big cock.

Charles said, “Whatever you’re doing, keep it up.”

His fingers probing her and teasing her clit, Will said, “Oh, I can do better than this.”

“Mmm hmm,” Amelia moaned in excitement.

Her heart raced as the mattress dipped from his knees moving under him. His fingers slipped out of her pussy, and left a slippery trail as they glided upward along the curve of her buttock. When his hand reached her hip, the other joined it on the opposite side. She sucked Charles hard and fast, making him groan and his fingers entwine in her hair.

 
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