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The time read 5pm on a bright and sunny Thursday evening. A popular coffeehouse located downtown was where most of the hard working dogs went to straight after work. There was a very tall, professional looking business dog having his usual snack named Kaiser Bradford. He was well known all over town.

At that moment, a younger male shepherd, Alexander Madison, entered the bar. His head bowed slightly in embarrassment then very slowly moved towards the older shepherd behind the counter and stuttered something Kaiser couldn't hear. After a short while, Alex turned around from the counter with a large frown on his face.

Kaiser saw the young teenage pup walk into the cafe. Instinctively, he knew that look all too well. The older shepherd couldn't bear to see a pup look so miserable so he decided to introduce himself and try to cheer him up. "Hello there, young fellow! My name is Kaiser Bradford. It's a pleasure to meet you!" Kaiser announced with a smile and held out his paw.

"Oh... hello, sir... my name is Alex Madison. Nice to meet you, too." The teenager shook the older shepherd's paw.

"Why don't you take a seat so we can talk? How are you doing today?" Bradford asked.

The younger shepherd nodded and sat down opposite Bradford. "Good... I suppose... Sorry, I'm just a bit annoyed."

Kaiser gave Alex a concerned look on his muzzle. "I'm glad to hear that you're all right. Is something troubling you, Madison? If so, please tell me what's wrong."

The young shepherd looked down to the floor as he began. "Well... I've been trying to get a job for ages now... But every time I ask about one I get turned down... It's just... really frustrating..."

"I understand exactly how you feel, Alex. There are so many jobs in this town and most of the owners show such a ridiculous amount of favoritism. So your father must be complaining about the bills piling up at home, huh?"

"Wh-What?" Alex looked up at the older shepherd with his mouth gaping open. "How did you know?"

Kaiser began to chuckle. "Well, I've known your dad since high school and we're still good friends today. Just answer one question for me and I might be able to help you start a job in no time. Why should I hire you for a position in my company?"

Alex's mouth hung open again at his question, but then he shook his head to snap out of it. "O-Oh, I'm..." The teenager takes a deep breath. "I'm hard-working, punctual and willing to put 100% into any task I'm given, sir."

"Wow! Spoken like a truly dedicated employee! I was most impressed by how you were able to answer the question under a bit of pressure. Madison, you're officially hired as my personal assistant." Kaiser smiled brightly and offered another paw shake.

Alex sat there in silence for a while, but then he got up and walked around the table and threw his arms around Bradford. "Thank you so much, sir! I promise to work really hard!"

Bradford started to blush and wag his tail happily as the young pup gave him a tight warm hug. "You're very welcome, Alex. I'll be sure to show you the ropes here."

"This is amazing.... I finally have a job..." The older shepherd felt a tear come into contact with his neck.

"Awww...please don't cry, Alex. I'm sure your father can see how hard you've been trying to find work." Kaiser said as he hugged Madison back.

Madison sniffed loudly and wiped his tears away from his face, still hugging the older shepherd. "Okay, sir..."

Kaiser gently nuzzled against Madison as the genuine hug continued for a while longer. Alex's stomach started to growl. "Madison, you've had a rough day. I want to buy you something to eat before we check out your new job."

"Okay, sir. I'll be as quick as I can. Thank you again." The young shepherd got up and walked towards his boss again.

A waiter came over to Mr. Bradford's table and asked if he was ready to order. "Yes, we are. I would like one bacon cheeseburger, a side of macaroni and cheese, a glass of Dr. Pepper along with 3 cinnamon sugar bagels, please."

"I-I'll have the same, without the mac and cheese, thank you." The waiter nodded his head and left towards the kitchen.

Kaiser started to laugh loudly at the pup. "The first order was for you, Alex. Oh well, guess I could use the extra meal."

"Oh, shit! Err... I-I'll get the waiter back..."

"Haha! There's no need for you to change our order now. It's all on me."

"If you're sure... I mean, it could be my first assignment, sir..."

"I'm sure. That won't do as your first task since you'll be getting paid for it." Kaiser winked at the teenage pup while trying his best to maintain his professional image.

"What? You'd pay me already? This assignment must be pretty hard, eh, sir?"

"Yes and I would do anything to help my best friend's son. You'll have to do a few hours of training with me tonight but your first task is tomorrow."

"Oh, that's fine, I'm sure dad will understand."

"Of course he will! This news is sure to save him considerable grief about his finances. Where does your father work at now? It's been a very long time since I've seen him."

"He manages a business and spends a lot of time in his office. I wish I saw him more..."

The older shepherd watched Alex's face frown up again and he wanted to know more about their relationship. "Are you sure? That doesn't sound like the Steven I know at all. You never mentioned anything about your mom, either. Is she doing all right?"

"Mom's fine, but she isn't working anymore. That's why dad had to take responsibility for the family's income."

"Oh, I see now. My poor friend... Does he enjoy working at his current job or not? I'm sure he really hates not spending enough time with you and his wife, Alex."

"Well, he is the owner so it's pretty stressful for him, I think. But he gets by and so do we. Me finally working will help too."

"I'm so glad to hear that, Alex. He's right; it's time for you to start helping him out financially." Kaiser said just as the food arrived.

"Yes. Hopefully, he can take some time off work if I do really well. Thank you." The young shepherd smiled at the waiter briefly before digging into his food.

"Please enjoy your meal, gentlemen!" The waiter said as he walked off. Kaiser's tongue started to drool once he picked up the bacon cheeseburger and took some huge bites out of it. "You're welcome, Madison."

Both shepherds devoured about half of their burgers in seconds then Alex moved to one of his bagels. "So good..."

Kaiser was rather hungry so he finished up the cheeseburger and licked his lips clean. "This place makes the best burgers in town, absolutely delicious!" The older shepherd said while letting out a satisfied murrrr.

"I agree!" Alex shouted with a mouthful of burger, and he blushed a bit. He finished his own burger shortly after and gulped down a bit of his drink.

Kaiser grabbed a napkin and placed it under the hungry pup's neck. "Good, just don't talk with your mouth full." He took a few sips of soda and pretty much devoured the warm Mac and cheese.

The pup started to feel a little embarrassed. "I know... Sorry..." Madison stuffed another bagel in his face.

"Alex, slow down and eat. There's really no rush at all."

"Y-Yes, sir..." The young shepherd slowed down immediately.

Bradford was nearly finished with his meal. He ordered a cup of hot cocoa to go along with his sweet bagels. The boss flashed Madison a quick smirk before checking his phone for work updates.

Alex looked at his boss's plate which was almost as empty as his. He found it amazing, considering his the older shepherd also had the same side order. He picked up his last bagel.

After a few taps of his phone, Kaiser ate every last piece of food off his plate and drank the rest of the warm beverage. He was waiting on the pup to finish so he could give Madison a tour of his headquarters.

The young shepherd savored every last bite of his bagel and drank the last of his drink. "Thank you, sir..."

"You're more than welcome, Madison. If you'll excuse me, I have to go use the restroom." Kaiser said as he walked off.

"Okay, sir." Madison smiled and waved at his boss as he left the table, waiting for his return.

Apparently, the older shepherd had one beverage too many and needed to relieve his bladder in the urinals. He unzipped his pants, pulled out his large penis and began to urinate heavily. "I just couldn't resist having a cup of hot chocolate..."

His break took a lot longer than expected because nature decided to take its course again. Kaiser started to think about the teenage pup in a sexual way. As much as he tried to hide it, Bradford was indeed attracted to his new employee.

Kaiser just stood there and closed his eyes, wishing that Madison was close to him at that very moment. He took a paw and began to stroke his 9 inch cock, moaning softly. The older shepherd became fully erect fast and sped up the pace while fondling his gigantic balls in a fast rhythm.

At this point, Bradford had been gone for quite a while but long enough for Alex to get worried. To set his mind at ease, he walked into the restroom and whispered: "Sir? Mr. Bradford? Are you okay?"

"A-Alex?! Yes, I'm fine. You can come on in...if you'd like."

The older shepherd stood in front of the urinal, pissing out all of the caffeine he had during his meal. His ears pricked with caution and turned to the side as Alex walked into the bathroom. "Sir, are you all right? You've been in the bathroom for a long time."

Kaiser sighed softly as his piss stream ended, and then he began to jerk off slowly, turning to the pup. "Lock the door, Alex."

Madison couldn't help but to stare at the boss's large member. Afterwards, he obeyed Bradford's command. "I have to say, your dick is huge...and a rather beautiful sight to behold, Mr. Bradford."

The older shepherd smirked as he gestured for Alex to come closer with his free paw. "Take a closer look, boy. I know you want to."

Alex slowly walked closer to the boss and reached his paw out to touch Kaiser's thick shaft. "It feels so warm and there's veins growing all over it, sir."

"Mmm that's real nice, Madison..." Bradford grabbed the teenager's paw and helped move it forwards and backwards on his throbbing cock. "Ever done this to yourself, boy?"

"Y-yes sir. I usually rub myself 4 times a day."

The older shepherd leaned forward and whispered seductively in Madison's ear. "Then your first assignment's gonna be easy. You're gonna give me a nice pawjob, okay? And if you do well, your first paycheck's coming early. Got that, Alex?"

"Yes, Mr. Bradford. I promise to get the job done and not let you down." Madison replied. He held the hard member in his paw then started to tease the head with a single paw tip before building up a nice stroking pace.

"Yeah... Thaaaat's it..." Kaiser began to rub up and down the pup's back as he felt him handle his length.

The teenage pup smiled and wagged his tail with joy as the boss complimented him on his work. He fastened a better grip around the growing shaft and stroked faster.

"If my tip weren't... covered in piss, I'd... ask for... more..." The boss began to breathe heavier and moan softly as the young shepherd handled him faster.

Madison giggled at the way Kaiser grunted between thrusts and loved to watch his boss squirm. "I must be doing exceptionally well with this task, right?"

"Oh yeah, Alex... Really really well..." Bradford would thrust into the younger shepherd's paw as he kept stroking its shaft.

Madison smirked and jerked his boss's cock upward, trying to match up with Kaiser's rhythm. He rubbed his paw pad across Bradford's tip and his body started to shake.

"Such a good boy... ahh... Doing reaaaaal good..." The pup felt his boss' cock throb a bit more frequently in his paw.

"Is there anything else that you would like for me to do, sir?"

"Heh... You might not be able to lick my tip..." The older shepherd winked suggestively at Alex.

"No, this is only my first assignment after all."

"Heh. Fair enough, my dear pup. How about you give my balls a rub instead?"

"Indeed I will, Mr. Bradford." Madison took his paw and got to fondle his boss's sack for the first time. It was very large and totally meant for making pups. "Mister...how are you able to walk with those big balls in the way?"

Kaiser let out a chuckle and moaned as his cock and balls were getting the teenager's full attention. "It's not easy... Will be easier soon... You're gonna drain them...for me."

Madison started to gently caress Kaiser's large scrotum and constantly rubbing them to excite the needy boss.

"Almost there, Madison... keep it up... ohhhh..."

Now, Alex decided to rub his paw pads together and let them finish the job. The boss's balls were firming up and begging to be emptied. He tugged on them and rubbed fast.

"Here it comes, boy..." The older shepherd let out a deep, aroused 'murr' as he began to cum hard, with spurt after thick spurt flying an inch or so into the air before landing on the pup's paw.

"Damn sir! You must have been seriously pent up! Why did you hold it all in so long?"

Kaiser could do nothing but moan loudly for a while as his orgasm continued, until the jizz on the younger shepherd's paw started to drip onto the floor. After his last spurt, Kaiser smiled and finally answered Alex. "I've been working hard recently... too hard... thank you..."

"You're welcome, Mr. Bradford. I guess anyone could see that you really enjoyed this. Just say the word and I will be there to satisfy all of your needs."

"Thank you, Madison... And I'm not gonna back down on my side of it either. You'll get your first paycheck soon."

"I really appreciate it, sir. There's something I want to ask you, Mr. Bradford. Were you...thinking about me in a sexual way? Is that why you took so to come out of the bathroom?"

"...Yes, Madison. After I was done pissing, I couldn't help but think about you... so I started stroking my dick."

The older shepherd smirked and gestured down to Alex's bulge. "Why don't you show me?"

"Hehe. I thought you'd never ask, boss." Madison took his pants off and exposed his 7 inch dick to the older shepherd. "Here I am."

"Damn, you're well-hung for your age..." Kaiser reached for it and ran two paw tips up and down the underside of its shaft.

Madison let out a surprised gasp as the horny boss began to explore his teenage manhood. "Thanks, sir. I'm an early bloomer. Mmmm your paws feel very soft..."

"Indeed you are... Mmm that's a tasty looking cock..." Without warning, Kaiser picked the pup off of the ground by his hips until his cock was in front of his nose, and then he pulled Alex towards him and began to lick his throbbing penis.

"Oh...GOD!!! T-that hot...smooth tongue...unngh!" Alex had no choice to moan and literally scream his boss's name. He never dreamed that an older shepherd would pleasure his body like this.

Kaiser smiled up at Madison as his tongue slowly ran up and down his shaft, and then he pulled him back slightly, realigned himself, and began to suckle on the teenager's tip.

"Ahhh...I like this a lot...being alone with you, boss."

"Mmhm?" The boss's head began to bob on more inches of Alex's dick, holding him in place above the ground with his muscular arms.

The teenage pup began to murrrr deeply as he spurted large waves of pre-cum into his boss's muzzle, giving him something tasty to lick. His cock couldn't last much longer since he was still going through puberty. Kaiser was already fully aware of this so he increased his suction and fondled Madison's big sack, which began to drive him wild.

The older shepherd pulled back for a second. "Feed me, boy." As soon as he said this, he leaned his head forward and engulfed Alex's entire penis, bobbing quickly on the last inch or so.

Madison whimpered as he felt like a huge ocean was going to splash out of him instantly. Bradford's suction became too powerful for the pup so he grunted loudly and let go of his pent up orgasm. He unleashed a continuous stream of warm sticky pup cream down his boss's muzzle.

"Mmm..." Kaiser murred deeply as he swallowed every rope of his employee's delicious spunk, pulling his head back off of his softening dick and setting him down on the floor. "How was that, Madison?"

Ohhh boss! That was the most...amazing sexual experience I've ever had in my whole life! Thank you...!" Madison said as he stared at Bradford and licked his lips with full seduction.

"I'm glad you liked it, Alex... If you'd like, we can do a whole lot more while you work for me..."

"I truly loved it, sir. That's exactly what I want for us to do." Madison said as he was trying to catch his breath.

The older shepherd stretched out his arm once again for another paw shake. "It'll be a pleasure to be working with you, Madison."

"Likewise, Mr. Bradford. I'm very excited to start work tomorrow." Alex gave Mr. Bradford the adjacent paw shake. "You certainly don't look like the type of dog who could ever be gay."

"Most people say that to me a lot. I'm proud that I am, because now I have you." The teenager saw Kaiser blush a bit.

"Awww gee...I'm glad that you're gay like me as well. You are a very handsome, sexy older dog, Mr. Bradford."

"And you're a really sexy young man, Madison."

"Thank you very much, sir."

"You're certainly more than welcome, Madison. Now, put your clothes back on and wait for me by the coffeehouse entrance." Kaiser said as he pulled his suit back on and readjusted himself.

"Okay, sir..." Alex, still a bit tired from his orgasm, picked his clothes up off of the floor, put them on quickly and headed out of the bathroom.