I was on a vacation with my best friend and his family. I'd never been to Hawaii and it was a dream come true. His family was super wealthy and his dad got a huge bonus at work, so he decided to treat his entire family. They invited me along because I had been friends with their oldest son, Max, for years. We didn't really talk about his family's wealth; we were too busy hanging out, drinking beer, and watching football.
I'd never met Max's parents or his siblings, but they were all very nice when I arrived at the airport in San Francisco. The whole family was going on the trip: Max, his brother Jules, his sister Amy and his mom and dad. They all greeted me with smiles and hugs. It felt really weird hugging a woman who was almost the same age as my own mother.
On the flight to Hawaii, I sat next to Jules. He was 18 and just graduated from high school. Max and I were 21, so I had always seen Jules as a kid. But, on this flight, I saw him as something different. He'd grown a lot over the past couple of years. He was taller than me, had dark hair and a strong jaw. I don't know if it was because I was feeling relaxed or what, but I found myself noticing his muscular arms and chest.
Jules was also wearing a really nice cologne that made him smell fantastic. He had a huge smile that lit up the entire cabin. His bright white teeth were perfect and he was always laughing. I was instantly jealous. He seemed like the kind of guy who never had a care in the world. Good looking, rich parents, a bright mind and on top of that he was also an amazing athlete. He was a great basketball player. He'd won the league MVP trophy the past two years.
He had everything a guy his age could possibly want and he had the kind of cocky attitude to go along with it. It was almost impossible not to like him though. He had a magnetic personality. People just seemed drawn to him.
I had never spoken to him much because he was three years younger than me, but on this flight I was finding it difficult to think about anything but him. He was so damn good looking. My eyes were constantly moving between his handsome face and his chest. He had the body of a Greek god. I had never felt this kind of attraction to a guy before, but there was something about him. I could see why so many girls were into him. It was widely known that he, just like Max by the way, was a huge player.
He had his pick of any girl he wanted, but he always went after the most beautiful and hottest girls in school. He had a reputation for scoring with the most popular cheerleaders and the sexiest sorority girls. Everyone knew about his exploits and I was surprised to see he hadn't brought one of his many conquests on the trip.
We flew first class and his dad had bought us all cocktails. I had a few and I was getting pretty buzzed. After a few hours, I could feel my cheeks were warm and red. I was also feeling more relaxed around Jules. I could tell he was a little buzzed too. He was looser, less inhibited and apparently also horny as hell.
When the flight attendant came by and offered another drink, Jules flirted with her shamelessly. She was probably a bit older than us, 27 I would've guessed, but she was really cute and dressed nicely in a pair of tight black slacks and a red blouse that showed off a fair amount of cleavage. I'd been watching her walk up and down the aisle, offering drinks and food and Jules was clearly attracted to her.
She came back with our drinks and Jules asked her name.
"Kelly" she replied, smiling back at him.
"That's a beautiful name."
"Thank you" she replied, her smile growing bigger.
"Busy shift?" he asked her, his eyes locked on hers.
"Yeah, it's a little crazy. We have a full plane and they're all drinking. Everyone's having a great time."
"I know why everyone keeps ordering drinks," Jules said with a sly smile.
"And, why is that?"
"Because, you're bringing them. I'd order a million drinks just to see you walk around in your tight outfit."
Kelly blushed and looked at Jules with a look of lust and amusement.
"Are you always this sweet to flight attendants?"
"Never" Jules said, flashing a cocky smile.
Kelly giggled.
"I'm Jules, by the way."
"Nice to meet you, Jules. I hope you enjoy your flight. If there's anything else I can get you, please let me know."
Jules said with a playful smirk.
Kelly giggled and looked up and down the aisle.
"Well, you can check me out whenever you want. I'll be walking up and down this aisle for the next six hours."
"I'm looking forward to it," Jules said, "But I was hoping I could get a more personal plan."
Kelly blushed and smiled and looked around the cabin again. She looked a little nervous, but she was obviously interested.
"I'll be happy to show you our personalized entertainment options when things calm down," she whispered in his ear before quickly walking away. She made sure to wiggle her butt a bit as she walked, turning and giving him a playful smile as she walked towards the galley.
I was sitting there stunned, unable to believe what had just happened.
I was impressed with his ability to flirt and also a bit jealous.
Jules turned to me and had a big smile on his face.
"I bet I'll have her in the bathroom within the hour."
I chuckled.
"You think you're that good?"
"Hell yeah. I'll have her begging me for it."
"No way," I said, shaking my head.
"You want to make a bet? Ten bucks says I'll have her screaming my name."
I laughed and shook his hand.
"It's a deal."
I wasn't serious about the bet, but he was. He leaned back in his seat and had a satisfied look on his face.
"Ten bucks, coming right up. It'll be nice to have a change of pace from the usual school girls."
My jaw dropped. I couldn't believe how brazen he was. I had never even flirted with an older woman, but he had his sights set on a 27 year old. I didn't think it was possible, but his confidence grew and he seemed to sit up straighter. I couldn't help but watch his every move.
