Stiles rolled up to the fancy golf club in his baggy blue jeans, purple and pink striped shirt, and white sneakers, the same clothes he was wearing the night before at a college party.
He looked himself over in the car mirror, eyeing his messy bed hair before letting out a sigh and reaching over to his glove compartment, grabbing his lucky baseball cap and placing it on his head backwards. He then turned off his jeep and headed inside.
The teen ran his hands down his shirt trying to smooth out any wrinkles before heading over to his boss. It was his first week on the job and he was already showing up late. He had his alarm clock to thank for that.
He set his alarm for nine in the morning, or maybe it was set for nine at night? Either way, he made it to work.
"Where were you? You're late, and I had to take time out of my busy schedule to show your nine o'clock the grand tour." His boss snapped.
"My alarm…" Stiles started to say.
"Save it. I don't want to hear it. Get to the back, change, and meet me back here so I can show you to your clients, now. Hurry up." The older man said annoyed, glancing down at his watch.
Stiles rolled his eyes but did as told, heading back to the staff locker room, undressing, and placing his clothes in the locker before grabbing a fresh pair of white shorts and a white shirt with the Gulf Club logo in gold trim on them, throwing them on quickly. He then locked up his stuff and placed his backwards cap back on, meeting his boss back at the reception area.
"Stilinski, there you are, took you long enough. Fix that hat." His boss ordered, taking it off the teen's head before turning it around, and placing it back on facing forward.
"This is an upscale place, not some run-down pub with a gang crew running it. Now, follow me and be on your best behavior, you will be dealing with one of our high rollers this morning, the CEO of Hale Enterprises, and some of his friends." The older man announced as he led the uninterested teen down the stairs to the small café area, where a bunch of middle-aged men were sitting around a table, all dressed up and ready for golf with a drink of tea in their hands. The men laughed it up as they had their own private conversation as the pair came up to greet them.
"Here we are, gentlemen. This Is Stiles and he will be your caddy today. If you have any questions or concerns don't hesitate to ask." The boss said reaching his hand out to shake the main guy in charge's hand.
"Thank you, I'm sure we can manage." The man replied back with a smile on his face.
Stiles took the time to look him over, he was a pretty attractive middle-aged man. He had short black hair, and a salt and pepper beard, wore fancy silver, reflective glasses that hid his eyes, and complimented his facial hair, and he wore a bright smile on his face, showing off his pearly whites.
"I'll leave you to it, gentleman. Have fun." The boss called out over his shoulder, on his way out of the room, before whispering to the teen, "Don't mess this up."
Stiles just nodded and waited until his boss was out of view before taking his cap off and switching it back around, letting it sit backwards on his head.
The CEO guy took notice and smirked amused.
"Okay guys, if you're done with your teas, we are going to head out to the green." Stiles voiced towards the group of men, waiting for them to get up and grab their belongings before following him out.
"After you." The teen said, holding the door to the outside for the group of men to head out to the golf cart.
The CEO was the last one out the door with his golf bag on his shoulder, he stopped short turning to the teen.
"Hi, we haven't officially met, I'm Derek." The man stated, giving the teen his outstretched hand.
He shook it lightly, "Stiles, nice to meet you."
"Likewise." The man said with a smirk on his lips.
The teen glanced over at his golf clubs.
"Here, let me take that for you, it is my job after all. Go ahead and join the others, I'll be there shortly."
"Oh, thanks. I appreciate it." The man replied, sliding the heavy bag off his shoulder and handing it over to the teen.
Stiles watched as the older man met up with his friends, taking a seat on the cart, as the teen huffed and dragged the jam-packed bag over to the back of the golf cart, setting them inside. Once done, he pulled out his keys and got in the front seat.
"You guys ready for an adventure?" He mused, turning to face the men.
"Yeah!" They shouted back excitedly, some laughing, others cheering as the golf cart went into motion, taking the group of men off to the green they were in search of.
After Stiles took his clients to the first hole and unloaded their clubs and balls, he headed off to the side, out of the way as they started taking turns shooting.
He did this time and time again; at each new hole they came upon. Eventually, another group came over to play and decided to join the current group, playing together, meaning Stiles got to chat it up with one of his coworkers who was caddying for the other group of players.
"How are you doing man?" His fellow coworker, Scott, asked as he came up to wait by him.
"Dude, I was at this killer party last night, the music was banging. I danced my ass off. Shit, I'm still a bit buzzed."
"Stiles, you're crazy. You're the only person I know that would come to work buzzed." He chuckled.
The teen just shrugged, and took a sip of water from a squeeze bottle, eyeing the rich stiff CEOS as they played out on the green.
Stiles couldn't help but eye Derek's ample ass in his tight shorts, and his muscular arms, as the man took his swing, hitting the ball.
"Damn, I'm going to be hitting that nice piece of ass later, just watch." He joked.
Scott raised an eyebrow intrigued, "Really? Care to make a bet?"
The teens were so engulfed in their conversation that they didn't even realize when the big-shot CEO man himself, came up from behind.
"Excuse me."
Stiles jumped in surprise and blushed slightly. Wondering how long the man was standing there or how much he could have possibly heard.
"Wha…uh. Yes, sir. How can I be of service? Would you like a new club, a drink perhaps?" Stiles voiced, trying to act professional.
Derek arched one of his thick eyebrows up and smirked amused at the teen's panic state.
"No, I would like a ride back to the front. Can you handle that?" He teased.
"Uhh, sure. No problem. I'll be right there." Stiles said before turning back to Scott.
"Hey, you can watch the rest while I'm gone, right?"
"Sure man. Good luck." He said, holding up a thumbs up as Stiles rolled his eyes before heading back to the golf cart, finding Derek already sitting in the passenger side, waiting for him.
Stiles got inside the driver's side and took off down the path they came from. The ride was silent.
Once they were halfway to the building Derek stopped him.
"Pull over here."
"Wha… I thought you wanted to head to the front." The teen replied confused.
"Pull over." The man repeated, a bit sterner this time.
"Ok, you got it." Stiles said, stopping the cart by some bushes, worried he was going to get a verbal lashing for his crude talk earlier with his friend.
He just hoped the older man wasn't going to tell his boss. He was already on thin ice with him and he needed this job.
He glanced over at the handsome CEO, about to apologize for his behavior earlier, only to freeze up in his spot as the man started to unzip his shorts.
"Woah, Wha… holy shitballs! He exclaimed as the man took out his swollen cock in his hand."
"Is this what you wanted?"
Stiles eyed his cock hungrily, licking his lips in anticipation
"Fuck yeah."
It didn't take long for the golf cart to start shaking and squeaking, with sounds of manly moans and honks of the horn going off and on from their actions.
Once done, the pair dressed, and got back in their seats.
The older man turned to Stiles, "So, how much money did you bet?"
"What do you mean?"
Derek gave him a stern look.
"Fifty bucks," Stiles said as his cheeks filled up with color.
"Hmm, I bet two hundred."
They both turned to look at each other, and chuckled.