"H-here you go, S-sir.." James Diamond heard as he looked up from his phone.

The man was lying in his deluxe king size bed while a much younger male brought him a tray with a Martini and one of his cigars on it.

That male happened to be James' assistant. Or, former assistant. The boy had only worked for the older male for almost 3 days.

James was a high class member at a prestigious country club in Beverly Hills. The man came from money and never had to work a day in his life. He became a member of the country club early in his twenties and 15 years later, he practically ran the joint.

Members as special as him were granted personal assistants. They were usually boys fresh out of high school looking for work. The job primarily consisted of golf caddying and fetching the men they served food, alcohol and other items upon request.

James, however, had another job for his assistants to perform. Or, it was more like an initiation. James usually liked to see how good his caddies were at taking a load or two up their ass. Early into their jobs he'd manage to seduce the boys and fuck them in his suite in the club.

If they were lousy, he had them fired and immediately replaced. The job paid well and he knew that there would always be a line of guys at the door hoping to getting the job when a position opened. The boys who were good got kept around and James continued to fuck them until he felt they were 'too old'.

The boy who had just brought him the tray was oblivious that James just sent a report to the club owner that he wanted the boy fired. That's what he gets for being lame in the sack.

The club owner had no problem with what James did. Most of the other members his age were doing the same thing. Those men were James' buddies and most of their conversations included how they fucked their assistants the night before.

Plus James paid well so they were in no position to tell him to leave.

"Thanks, Carlton. Just leave it on the night table." James said, looking up from his phone.

…

"So, is there is anything else I can do for you, Sir?" the boy asked, not even correcting his boss on getting his name wrong.

"You can get your ass out of here. Your shift is over." the man said as he lit his cigar.

"B-but, it's only 6:30, Sir." the younger male replied

"Did I fuckin' ask for the time? Leave." James was angry. Usually after the first fuck his assistants would limp out of the room and find a shower to get cleaned up in. This one was so needy and persistent. It made the man sick.

But, in James' defense, he was still naked with only a thin sheet covering his left leg and crotch. That was probably his reason for not jetting off.

And that was a valid reason in James' eyes. He was a very handsome man. He could have anyone he wanted and had 38 years of evidence. Everywhere he went people practically threw themselves at him. While he could be with another man or woman his age, he preferred to be with much younger boys, none of whom were at all taller or beefier than himself.

Three days later and James was without an assistant. Usually the replacement would be at his front door the morning after. James was beginning to get a little pissed off. Having to pour is own whiskey was exhausting. He knew the next guy hired was getting fucked extra hard for making him wait so long.

The man thought that the more he dwelled on the matter, the longer it'd take. He pushed the annoyance out of his mind and snapped his focus back to the story his buddy Logan was telling to the group of men seated near James on a balcony over looking the club's lake.

"And so I said" Logan chuckled "Daddy's not gonna give you cummies until you buss it open real good." The men amongst James roared with laughter. Frankly, James had no idea what Logan was saying. But, judging by the blush on the boy sitting on Logan's lap, it was something sexual.

Just as he noticed that, a vibration in James' right shorts pocket began. It must've been his phone. He quickly pulled it out and checked to see the message. It was from the guard, stationed out front in the parking lot. He alerted James his new assistant had arrived.

Fucking finally.

Without a word, James raced out of his seat and onto a golf cart parked near the door outside of the rooming area. He was ready to meet his new caddy and more importantly, bust a nut down his throat.

The parking lot was only about half a mile away. The golf cart got him there excruciatingly slow. After maybe 5 years, James hopped off of the golf cart and showed his ID to the guard, allowing him to open the ginormous brass gate doors so the new worker could meet his boss.

James posed while the doors drew away from each other. He wanted his first impression to look hot. What he didn't expect, however, was to think the exact same about the much younger boy facing him.

A slim, blonde male stood across from James. He had a very lazily unshaven amount of hair on his chin and green eyes big enough you could see your reflection. The boy was already decked out in his uniform. A bright yellow polo shirt, plaid khaki shorts and a tan baseball cap, pointed backwards on the boy's head.

"Hello, sir. My name is Kendall. I'm your new caddy." the boy explained, completed with a beaming smile and extending his arm out so he could shake hands with his new boss.

James took a second to come back to reality. He tightly grasped the the younger boy's hand, earning a small gasp, and shook vigorously. "Hello, Kendall. My name is Mr. Diamond." He said with a smirk. "C'mon. Let me get you settled in."

The blonde happily obliged. He set the duffel bag he had brought along with him onto the back of the cart and climbed up onto the front seat, right next to the much older male ready to drive him straight into his new job.

"Tell me about yourself, Kendall." the boy heard the taller man ask. Before getting a chance to let out a single syllable, he felt James' arm creep around the back of his neck and hang over the boy's shoulder. The action effectively led to James pulling Kendall closer to his body.

"Oh." Kendall was very aware of how thing worked around here. He read many reviews of previous workers for the country club, many of them going into great detail about the extra service they had to do. The boy figured he'd have to perform the same acts. And while Kendall was fine with doing said acts for the type of pay he'd be receiving from the club, he didn't expect it to happen right away.

"Well, I'm uh, 19. One year of college. I had to leave because my school dropped my major. I used to live in-" the younger boy shuddered after being cut off. James snaked his right arm down he boy's chest and began to caress one of his nipples with his much larger, rougher hand.

"Go on." James commanded, acting as if he wasn't feeling the kid up at the moment.

"I'm from..uh Minnesota. It's filled with a lot of Norway Pines."

"Very interesting." his new boss said with a smirk and a pull on Kendall's bud, putting extra length on to every syllable to prolong his double entendre.

This was impossible. Kendall was just babbling by this point. It's not like he was to blame or anything. James was deliberately fondling him as their cart passed many of the estate's pampered members.

"Ah! Here we are!" James said trying to look as professional as possible. Despite the look he gave Kendall, both of them were happy as hell to have arrived.

James showed Kendall the basics of the club. He took the boy through a very quick, very hasty tour of the surrounding area of the wing James' loft was in. The man was desperate to make his move and if he waited just one more minute or if Kendall insisted on looking at one more lounge area, he might literally bust a nut.

"And last and certainly not least; my place!" the 38 year old remarked as he proudly displayed his prestigious living area to the blonde.

James' loft was a modern style, one story apartment over looking the nearest gold course. He lived on the highest floor of his building and was the only resident whose home was situated with a balcony.

Kendall walked around the kitchen area, amazed at the marble counter tops and crystal silverware. His apartment looked nothing like this. He and his roommate weren't even sure if they had an island in their kitchen anymore, considering it was so covered is frivolous junk they could never throw away.

And he wasn't about to compare the chair they fished out of a dumpster to James' flat screen and Poltrona Frau Kennedee Sofa (the only way he knew the name of the couch was from James boasting about every single possession Kendall put his eyes on)

Gripping the bags Kendall had set on the floor and tossing them at the boy, James suggested that he should set up some of his items in the guest room designated for his assistants. "And after you're done doing that, meet me on my balcony. I wanna get to know each other."

The boy happily obliged and wandered down the hallway, looking for his new room. James hauled ass to the kitchen and poured himself a mimosa, something he still wasn't used to doing himself. Without spilling a drop, he ran to the balcony and settled himself into one of his lounge chairs. He whipped out a case of cigars from a drawer and lit it with just enough time to unzip his charcoal colored pants and whip out his aching dick.

Kendall had taken quicker to set up than James had planned. Fair enough, though. The man was ready to slam ass *now*.

"Alright, Mr. Diamond. I just put my toothbrush in the bathroom and left my shoes on the floor in there." he said before realizing his new boss was stroking himself.

"Oh..I didn't r–"

"What's wrong? Haven't you ever seen another man's cock before?"

…..

"Well….yeah, it's just that…"

"Just what?" James asked proudly, taking his cigar from in between his teeth and into a nearby ashtray.

"I've just never seen one so big." Kendall replied with the slightest bit of a chuckle in between words.

In the blink of an eye, James leapt from his chair and swept Kendall up bridal style. He carried Kendall to the mater bedroom as the younger boy felt up his boss's beefy shoulders. Even though he thought that this was going by extremely too fast at first, Kendall couldn't deny he thought James was damn fine. And the attitude the man had was pretty appealing too. Kendall loved how bold he was being. Plus the fact that he hadn't even been in James' loft for 9 minutes and they were already about to fuck was astounding. He actually felt pretty proud of himself.

James tossed Kendall onto his mattress and took no time ripping off his sweater. His hairy pecs looked down over the now trembling blonde boy who was fumbling to get out of his clothes.

His boss, fully naked in record speed, yanked this shorts and briefs off, letting his erection spring free.

"You ever been fucked before, Kendall?"

"No, Mr. Diamond."

"Please" James purred, pinching the younger male's taint. "Call me sir."

Instantly kneeling down, James spread Kendall's ass cheeks and went to town. The boy's eyes bulged and his knuckles went white as the older male's tongue darted in and around his hole. The boy had a few drunken hook ups here and there. Nothing serious came out of them. He certainly never bottomed. Having his ass eaten was a life changing experience.

The man shot up and darted to his dresser in hopes to find a bottle of lube. Ass eating wasn't getting the job down quick enough. In the corner of his eye, James noticed something interesting. Something he could use to his advantage. He grabbed the item without notifying the boy and seated himself back in front of his withering hole.

James more or less wasted half a bottle on Kendall's virgin hole. He was clenched tight, but the man was dead set on getting up in there.

Kendall was just thankful that this floor was apparently privately owned by James alone. He would have been embarrassed if any of the other guests heard his desperate cries for James to keep jabbing him.

The brunette shot up with his dick in his hand and a smirk on his face. "You ready, baby?"

"Fuck yes, sir." Kendall said, looking up. All James saw was a sweaty mess who was currently suffering some respiratory issues.

Granted, the boy had never bottomed, so he wasn't sure what to expect. But he really didn't think a cold sphere shaped object was located anywhere on a dick. He tried to sit up and see that James wasn't pushing his dick into him, but instead, a golf ball.

James took notice that Kendall was aware of the situation and took advantage, twisting the ball with two fingers as it was pushed farther and farther into his hole.

"You like that?" the brunette asked, stroking himself to the sight of the younger boy's muscles clinging to the shiny white sphere disappearing inch by inch.

Judging by the nonsensical groan the blonde let out, he did.

James' body shot up after confirming to himself that the golf ball was far enough in there. He bent his body over top Kendall's and hooked the boy's bottom lip in between his own. "I'm not gonna fuck you." he said, locking eyes with him. "Not until you leave the ball in you for 24 hours. Sound good?"

"mmmghhmm!"

"What was that!?" James sternly yelled, accompanied with a shooting dark glare and a strict smack to Kendall's sweat coated cheeks.

"Yes, sir!"

With that, James relocated himself back on his feet. The name he commanded Kendall use on him had sent a surge through his ears straight down to his dick. He tightly gripped his dick in hand, along with Kendall, and simultaneously jacked both of them off.

Not even 2 seconds later, James felt the other male's cock twitch against his and watched as he abruptly came all over his own chest. Letting go of the boy's cock, the older male clenched his teeth and aimed his erection toward the blonde's face, covering his nose and chin with his cum.

The two froze there, with the only indication that they were alive being the rough sounds of their heavy breathing and rising chests. Both were surprised at themselves. Kendall never expected to slut it up for someone he had only just met, or having something in his ass. James was surprised how much he enjoyed it. Usually he found sex with his assistants pretty decent, but never anything this spectacular. Just fingering Kendall and jacking him off pretty much had James reevaluating his entire past. He couldn't imagine what his ass would feel like. There was absolutely no way he could wait 24 hours.

The older gentleman walked into the accompanying master bathroom and returned seconds later, throwing a wet towel on Kendall's stiff body.

"Clean yourself up. I'm hitting the fields in 5 minutes."

Author's Note: I wanted to upload two chapters of this fic at once but I haven't written anything since I finished this 4 days ago and I've felt guilty. There will be another chapter, probably a third too. Not too plot heavy, though. The rest of the story will be 99% smut.