Bears Best Assisstant

Story by JaketheCoon on SoFurry

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A young raccoon, moi, receives an unexpected promotion as the CEO's personal accountant/assistant. Doesn't help that he's a sexy as hell bear!

Story written by: smounged1989

The buzzing of the alarm jolted the young raccoon from his restful sleep. With a low groan, he rolled over and slapped the small plastic box several times until the buzzing stopped. A soft sigh escaped from between his lips as he stretched out his long, lithe body. The small sound of his back popping as he stretched was followed by a long low moan of pleasure that brought a smile to the coon's face. Opening his hazel eyes, Jake pulled off his covers exposing his skinny body to the cold morning air. His fur stuck out at odd angles after a night of tossing around under the covers. Sitting up straight, the young fur swung his legs over the edge and hefted himself up, stretching once more.

He stood at no more than five feet five inches tall and weighed no more than one hundred and ten pounds. Many of his female friends had told him in the past that they would kill for his body. Short, tight and eternally thin no matter what he ate. The widest part on his body were his hips. The meaty hips making his rear stick out firmly and perky. He always got complements on his ass. Either verbal ones or subtle gropes/pinches while he walked down the street. Scratching absently at his flat belly, Jake stumbled sleepily through his tiny apartment. His tail swinging lazily behind him as he made it to the bathroom.

Turning on the shower, he let the water heat up while he set about his normal morning routine of brushing his teeth, using the toilet and cleaning out his ears. By the time steam filled the small bathroom, the raccoon was almost fully awake. Stepping into the hot spray, he instantly let out a sigh of relief as the hot water soaked quickly into his fur, making it lay flat and tight against his body. Grabbing the bottle of special silky smooth soap, the young male set about cleaning his grey and black striped fur. During his wash, he tried to prepare himself mentally for the day ahead.

Jake worked in the accounting department of a large business. He wasn't any of the overly important accountants, he was just one of a half dozen others who worked the books for the big wigs. Even though he took pride in his work. He had his own little cubical that no one else ever entered unless they needed him. He had a small group of work friends who he enjoyed talking with and having lunch with as well. The only real problem he had at work was his boss. His name was Morgan Jackson, an over weight rat who did nothing at all except yell at everyone else and take credit for the work they did.

Jake hated him. He seemed to pick on him more than anyone else. He would of gone to HR but he was too worried that the rat would find out he was the one who complained and then make his work life even worse. Shivering, Jake realized he had been lost track of time and that the water in the shower was starting to turn cold. Quickly rinsing off the rest of the soap, he turned the spray off and stepped out. Using two towels he began to dry himself off before grabbing his special brush to comb his fur until it was silky smooth. With a faint smile on his lips when he looked in the mirror, he winked and blew himself a kiss before shutting off the lights and going to get dressed.

Thirty minutes later, Jake was running down the side walk, a thermos of coffee in one hand and a file folder of papers in the other. Since he had spent so long in the shower, he was now running behind and was having to run in order to catch his bus to work. While he had been running out the door of his apartment building, he had almost ran head first into his neighbor from across the hall. Jake didn't know his name, but he was a big burly black furred wolf. He had a very muscular build even though he had a bit of a belly. His golden/green eyes where always glaring around like he was pissed off at the world. Every time the raccoon had seen the guy, he wore nothing but dirty and torn blue jeans that kept slipping down his large rear and a dirty stained wife beater shirt that showed off his large arms and chest as well as rode up on his beer belly. A large hooped piercing hung from his nose and he smelled heavy of sweat and musk.

The guy had growled at the raccoon when he ran into him and muttered under his breath something Jake couldn't hear. Not wanting to waste anymore time, he said he was sorry and ran off to catch his bus. Having only just caught the bus before it roared off, Jake sat in the dirty lumpy seat, panting hard as he tried to catch his breath. Closing his eyes he let out a heavy sigh before opening his thermos and taking a small sip of the hot coffee inside. The rush of the bitter drink settled his pounding heart and made him smile.

"Running late, huh?" A soft voice said from beside him.

Jake turned to see the smiling face of a female husky. She looked to be about the same age as he was but several inches taller and a good thirty pounds heavier. He felt the inside of his ears blush slightly and nodded. "Y... yeah, spent too long in the shower and almost missed the bus."

He coughed slightly, having only realized that what he had said could lead the women to believe he had been doing something very naughty in the shower. She smiled at him and flipped her long white hair over her shoulder. "I know how that is. Yesterday, I almost missed my bus to work too. It's just so hard to get out of the shower in the morning."

Her words made Jake smile. She had understood what he had been trying to say. The two of them continued to chat for a while longer, the raccoon slowly getting over his shyness and opening up a bit to the husky who, in turn, smiled at him and eventually gave him her number so they could possibly hang out some time. "I don't want you to think I'm hitting on you or anything." She said as Jake's stop came closer. "I mean, after all, I know you're gay and everything..."

Jake cut her off mid sentence. "Wha... how do you know I'm gay?" He asked, his ears burning as blood rushed to his face. It was true and he had a crushing feeling that he knew her answer.

"Come on honey, your more feminine than I am!" She said, taking hold of his hand and giving it a soft squeeze. "It's not a bad thing dear, just makes it obvious. Hasn't anyone ever told you that before?"

The raccoon nodded softly and sighed. "I'm sorry, I thought I was getting better at not being so..." He trailed off and just flapped his hands in a limp wrist fashion that made the girl laugh loudly.

"Oh hush now, don't you go trying to change yourself just to make other people happy or whatever." She pulled him into a tight hug. "You're adorable, charming and very funny. Just be yourself and don't listen to what anyone else says!"

Before he could reply, the bus lurched to a stop and he stood to leave. Before he got off, Jake turned back and smiled at the husky. "Thanks." She smiled and said you're welcome. Hopping off the bus, Jake waited until it drove off before crossing the street, heading to the large building that he worked at.

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For the most part, Jake's day was uneventful. He crunched the numbers of several different accounts for a few hours until it was time for lunch, at which point he went off to the small break room and sat in the back corner with his few work friends. They chatted and joked about random nonsense for thirty minutes or so, then they all headed back to their little cubical to crunch more numbers until almost three in the afternoon. It was a universal truth that the work day always slowed down after lunch time. As if it was trying very hard to stretch the time between one o'clock and five o'clock to double its actual span.

True to form as the small digital clock at the bottom of the raccoon's computer hit three he felt like he had already been there for an extra six hours. Leaning back in his small chair, Jake stretched and arched his back, moaning as a few loud pops sounded from his back as his spine decompressed. "Ooohhhh yeah!" He moaned out as the small rush of pleasure ran through his body from the action.

A hard bang against the flimsy wall of his cubical made him jump and spin around in his chair. Standing at the entrance of his small space was his fat rat boss, Morgan Jackson. Jake didn't know how he had missed the slob sneaking up on him. The guys BO was usually so strong you could smell him before he even got off the elevator. He must of taken one of his rare monthly showers cause he didn't smell as bad as he normally did although he was still a bit ripe.

"CoonStrum." The rat hissed out his large, flabby belly jiggling with every panting breath the guy took. "My office, now."

The rat didn't even wait for a reply before turning and walking away. Jake gulped hard. Everyone knew that you only got called into the rat's office when you were in very serious trouble. With a barely held in sigh, the slim raccoon saved his work on the computer, brushed himself off and headed off to meet his doom. As he walked through the forest of cubicles, Jake spotted several heads poking out to watch him as he made his way over to the office at the far end of the floor. His normal cheerful swish in his step was replaced by the slow and stiff walk of a condemned criminal.

During his long walk to the gallows, Jake tried hard to remember any bad or wrong doings that he had done to warrant this call. His mind instantly went to a point in time a week ago were he had sent in a report claiming that there where some massive problems with one of the accounts numbers. He had spent an entire day trying to account for several hundred thousand dollars worth of product and revenue that was mysteriously missing from the books.

"Maybe that's what this is about?" He muttered to himself, his bushy tail dragging over the carpeted floor. "Maybe he's going to yell at me for being too stupid to figure out that the missing money was subdivided into another account or something."

In the back of his mind, Jake knew that didn't make sense. But with his brain focused fully on this ending with him either being suspended or fired, he wasn't listening to logic. He stood in front of the office door that was oddly shut even though the rat had to of just gone through it. Taking a deep breath, the raccoon opened the door and stepped into the office. The smell was the first thing that hit Jake. It reeked of musk (and not the good kind), sweat, dirt and a bunch of other unpleasant things. The smell made Jake's eyes water slightly and he had to blink several times to get the tears to go away.

The next thing that he realized, which was by far more shocking than anything else so far, standing, or rather leaning, against the front of the rat's desk was the massive form of Richard Bullion. The bear stood at almost nine feet tall, his arms, chest and legs bulged with muscle. He had a massive belly, but unlike the rat's it was firm and hard rather than soft and flabby. Thick dark brown fur covered his whole body and his eyes blazed with an intense internal fire that always sent others scurrying away or agreeing with whatever the guy said. These things helped him rise to the powerful position of CEO of the company within the short time of only ten years. Not bad at all for a thirty eight year old bear.

The tailored suit the bear wore hardly seemed able to contain his massive bulking body. His firm belly alone looked about ready to burst out of the fitted button down white shirt, let alone every seam on the jacket, and the pants looked about ready to rip apart to expose the bulging muscles. Jake gulped harder than before. If Richard Bullion was here, he was in so much trouble that he might as well dig his own grave and throw himself into it.

"Shut the door." The bear said. His voice was deep and rich like dark chocolate, but there was a small growl hidden inside that spoke of bad things if even this simple command wasn't followed. Like an obedient servant, Jake closed the office door, locking all the horrible smells inside. Mr. Bullion didn't look like the smell bothered him at all. "So, this is Mr. CoonStrum huh?" He asked crossing his arms over his massive chest.

Jake could feel the bear's eyes burning into his very soul as he looked him up and down. Jake tried to say 'yes sir,' but his throat was too dry to do more than let out a small squeak. From beside the bear, Morgan Jackson glared daggers at the raccoon before letting out a small huff. "Yeah, that's him." There was an extra venom in his voice that Jake had only heard on a few rare occasions when the rat was forced to acknowledge someone else accomplishments.

The bear stared down at Jake for several long moments before a large grin spread over his face. "Well god damn kid, no need to look so scared!" His voice suddenly had a higher note to it. As if he was extremely happy about something. "Damn Morgan, didn't you let him know that he wasn't in trouble?"

The rat curled up his lip exposing several sharp needle like yellow teeth. "It must of slipped my mind." He grumbled.

"I'm sure it did." Mr. Bullion grunted pushing off the rat's desk and stepping closer to Jake. "Mr. CoonStrum," he took the 'coon's hand in his own very large one and shook it firmly. "I want to thank you for all you've been doing for the company and after last week I had to come down and get a look at you for myself."

Jake was extremely confused. He tried not to wince at the painful grip the large bear had on his hand. "Um... thank you sir. And please call me Jake." His voice sounded so weak and small compared to the bear's.

"Jake it is then." He boomed, his smile never leaving his face. "When the report came across my desk last week, saying that one of the accounting guys found a major problem with one of our accounts, well I almost threw my desk out the window!" He laughed. "I was sure that it was either some kind of joke or a major mistake on someones part. But then I checked and double checked the numbers and hot damn if you weren't right as rain!" Jake's head was lost in the words coming from the bear's mouth. "Um... oh!" He said, finally catching up. "It was nothing sir. Anyone who had the account information would of been able to find the mistake."

The bear shook his head. "Oh no, son. You see, the person who usually handles that account is normally my personal accountant/assistant!" A soft growl came to the bear's throat as he spoke now. "That no good little fucker's been skimming money from our accounts for years! Had he not been sick last week and that account gone to him instead of someone else, then who knows how long it would of been before we found out about it!"

Jake felt his ears burn with embarrassment at the bear's words. In truth, he hadn't done anything special at all. It was just pure luck that he had been given the account instead of one of the other workers. But Mr. Bullion didn't seem to be interested in hearing that sort of thing.

"Anyway, when I found out what was going on, I had to come down here and see the employee who did such an amazing job!" His large hand came down on Jake's back several times, patting it firmly and knocking the wind out of the small raccoon's lungs. "Of course, we had a small problem finding the person who had done it, didn't we, Morgan?" The bear glared at the rat who had seance enough to look ashamed of himself. "Apparently someone had been trying to take credit for work that wasn't his..." The rat's head lowered. "But that will be sorted out later on." He continued happily.

"Well... I'm happy I was able to point out the problem sir, and that it can be fixed." Jake said, wishing that he could go back to his cubical. Being so close to the large male was starting to... affect him. He carefully tried to move his hands in front of his pants to block the small tent starting to form there.

Mr. Bullion patted Jake's back a few more times before pulling away slightly. "Yes, yes indeed." He muttered. "But you see, Jake, now that the problem has been pointed out and dealt with, it's brought up a whole new problem that needs to be addressed right away." The bear looked down at him, the fire back in his eyes as he seemed to finally get to the meat of the situation. "Obviously someone who as been stealing money from the company can't be allowed to remain employed here. My assistant, or should I say former assistant, is no longer with us." He smiled softly and his eyes unfocused slightly as he absently patted his large firm belly and gave it a few rubs. After a moment, he seemed to snap out of his day dream and cleared his throat. "So that brings me to my main point. I need a new assistant/personal accountant. This person needs to be smart, task oriented and willing to put in long hours both here at work and on their off time, since they will also be in charge of my personal finances."

Jake instantly began to think of several of the other workers who he thought would be great for the job. "Well sir, if you'd like I can make a few recommendations..."

Mr. Bullion paused looking down at the raccoon, his eyes wide for a moment. Then with a barking howl of laughter he thumped Jake on the back several times, almost sending the smaller, thinner male crashing to the floor. "Oh god, if that ain't the funniest thing!" He laughed for several moments before wiping a tear from his eyes. "Whoo... I needed that..." He chuckled a few more times. "I was actually already thinking of someone for the position." He gave the raccoon's back a few more pats, gently this time. "What do ya say kid?"

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Jake felt like he was in a daze. Even though it had happened almost a week ago, he still couldn't wrap his head around the fact that he was now the personal assistant/accountant to the CEO of the company. The day he had been offered the job, and accepting it, cause honestly who would be crazy enough to turn it down, he had been sent home early with a company credit card with the direct orders from the big bear to get at least three new high class suits for his new station.

The raccoon had done just that, even going so far as to buy a nice new pair of leather dress shoes and a slick tie or two as well. Every day for the following week he had shown up at the office and instead of getting off at the fourth floor like normal, he rode the elevator up to the fifteenth, the very top floor not counting the roof. He had been shown his desk, which was larger than his cubical had been, by a very happy and eager Mr. Bullion. The large bear seemed to take an instant liking to the raccoon, who was finding it harder and harder to control his arousal around the massive male. The guy seemed to be everything he found attractive in a man. He was big, manly, assertive and dominate and didn't seem to mind his more effeminate traits. In fact, on several occasions, the guy had told him that he didn't need to put on such a show of being butch when he clearly could tell that it wasn't how he normally behaved.

So there he was, sitting behind his heavily wooden desk in a pressed dark black pin striped suit and red silk tie. His fur was combed and brushed until it shined and he had even got an expensive bottle of smelling spray. Slowly he was beginning to relax in his new position and felt comfortable enough to act like himself. For the most part, his new job wasn't much different than his old one had been. He still worked on accounting, only now it was for their more important clients as well as budgeting Mr. Bullion's personal accounts. Already he had managed to save the bear almost two grand by doing some fancy accounting, which made the bear very happy. Every so often he had needed to pause in his work to fetch the big guy lunch or coffee. He was also suppose to set up the board room whenever a meeting was about to happen.

To say Jake was happy would be a gross understatement. Jake was on cloud nine! He was actually able to have his desk decorated the way he wanted, which had been a huge no no before since any sign of personality would get stomped out by the fat rat. But the bear seemed happy to see the raccoon's personal touches to his work area. Often times he would spend a few minutes each day chatting with him about some of the things he had on display. It had taken a while, but finally Jake worked up the nerve to tack up a small calendar and the wall behind his desk. It was one of the special edition hunky firemen calendars they sell at novelty shops. Each month had a different hunky model dressed in firefighter gear, or at least as much of the gear as they could get away with wearing without it being a straight up porn calendar.

Jake hummed happily to himself as he typed away at his top of the line computer. It was almost lunch time and he was just thinking about what he might get from the diner across the street when Mr. Bullion's voice came from the small phone speaker at the corner of his desk. "Jake, can you come in here for a moment?"

Quickly clicking the small red button that let him answer, Jake replied. "I'll be right there sir."

Typing a few more things into his computer, Jake quickly saved his work and closed the lid of his laptop. Standing, he left his suit jacket on the back of his chair and walked briskly to the large double doors of the CEO office. They where heavy oak and he had to use two hands and all his weight in order to push one of them open. When he managed to open it enough for him to slip inside, he did so before the heavy door could close on him.

The office he found himself in was massive! The ceiling was a good fifteen feet high and painted a dirty brown color. The walls were of a similar color and the carpet was a plush and deep red. Two large sofas sat on the right side of the room, one against the wall and the other facing the wall. A large coffee table was set between them. Jake had seen Mr. Bullion use this area before for non formal meetings or to eat his meals when he wanted to continue working while eating. On the left wall was a huge forty five inch flat screen television that was on and showing the news. The volume was off but the subtitles where flowing across the bottom of the screen.

At the far end facing away from the large wall window was a massive red oak desk. It was hand carved and decorated with many different swirling designs. An assortment of papers, books, binders and folders where laid all over the surface along with a laptop computer and a desktop computer as well. Jake had asked Mr. Bullion why he had two computers on his desk like that the first day he had started his new job. The bear had told him that the only way he could get all his work done was to multitask several things at once. The two computers allowed him to do all his work without over crowding any one device. He also had a small hand held tablet and PDA that he also did smaller work on.

Unlike Jake's work space, Mr. Bullion didn't have much personalized items set up. He had a few trinkets here and there but nothing that spoke of his personality or home life. Jake was very interested in knowing more about his boss but had been to afraid to ask anything personal. After all, he had only been working for him for a week. Looking around for a moment, he found the massive bear spread out on the couch pressed right against the wall. His jacket was off and thrown over the second couch. Elastic suspenders stretched tightly over his massive frame, helping to keep his trousers up on his muscular thighs. His firm belly stuck out threatening to bust open his shirt and his chest would be doing the same had he not undone several of the buttons exposing the tightly stretched white tank top undershirt he wore under it. His head was resting back on his broad shoulders and his eyes where closed slightly as he stared at the ceiling absently.

"Sir?" Jake asked softly, not wanting to startle the bear.

Raising his head, Mr. Bullion's face broke into a small smile and he chuckled slightly. "No need to act so scared. Come sit for a moment." He gestured to the small space on the couch next to him. The raccoon would of preferred to sit on the other couch so as not to risk an uncomfortable situation but he didn't want to refuse the bear. So very carefully he sat down in the small space left open to him next to his impressively massive boss. After a moment, Mr. Bullion's large arm moved down to rest on the back of the couch behind Jake's head. A moment later he curled it around the raccoon's shoulders and used that grip to pull him closer to his side. Jake felt the heat rush to his face as he was pressed against and almost pulled into the large males lap.

"Ya know Jake..." Mr. Bullion started after several moments. "Being the boss of a company like this folks probably think that its all fun and games. That I can do whatever the fuck I want and not do any real work." He said the last part with a small huff. "Yeah, I wish. Sometimes I wish I was just a regular worker. Clock in at nine leave at five, have days off where I don't have to worry about the company or anything. Actually have a social life and someone meaningful to come home to."

Jake's blush began to fade and he felt his heart rate slow as the bear seemed to be unloading some pretty deep and stressful information on him. It sounded like this was stuff the bear had on his mind a lot and never really got the chance to vent. "I would imagine..." Jake said slowly. "Its not very easy having the position you have. Even if you met someone, it would be hard to tell if they actually liked you or just wanted you for your connections or money."

A soft chuckle came from the bear. It was deep and vibrated through the bear and into Jake, making his heart speed up slightly again. "It kind of sounds like you know a little something about that huh?" Jake nodded but didn't say anything else about it and he was grateful when Mr. Bullion didn't press the issue. "Yeah, most of the time if I'm not here doing work, then I'm at home doing work."

The two fell into a small silence for a while before the bear grunted and patted Jake's shoulder. "Enough of my pity party. Why don't you order us some food and we can have lunch?" Letting out a huff of air, the bear lifted himself off the couch and moved back over to his desk. Jake was about to do as he was told before the words registered in his mind.

"You... you want me to eat lunch with you... sir?" He asked, his voice soft and unsure.

"Well of course!" The bear replied looking at the raccoon. "I think it's about time we got to know each other a bit. After all, being my assistant means that I'll be calling on you for personal matters. Sometimes I may need you to run to my home and get something I forgot. I'd like to get to know you a bit before hand. Wouldn't be smart to just let some random person into my home, right?"

Jake nodded slightly. It made sense. Turning and leaving the office, he pulled out a menu from a Chinese delivery place from his desk drawer. He didn't know what Mr. Bullion would want, so he just got a few different things and hoped for the best. He made sure to get several orders, since he was sure that the bear could eat his weight in food. His mind was playing over the conversation he just had. Had Mr. Bullion called him in there just so he could confide in him? It wouldn't be so surprising if he had. Even powerful CEO's like him needed to unload their problems every now and then. He felt a small twinge of pity for the guy. He seemed to have everything except the real important things, like friends and loved ones. It would explain why he was so interested in other people's lives and why he didn't have anything personal in his office.

Taking the steaming bags of food when they arrived into the large office, he set them out on the coffee table between the couches. For the next hour, the two of them sat on the couches, eating the hot tangy food and chatting. Mostly they talked about Jake and what he liked to do and so on. Over the course of the meal, they began talking about past relationships. Jake was surprised to find out that Mr. Bullion, who by this point had insisted on Jake calling him Richard, hadn't even been on a date for almost ten years! Jake had confessed that he hadn't dated in over a year, not since he had broken things off with his last boyfriend.

"Walked in on the fucker in bed with the apartment's maintenance man." Jake had said with venom in his voice. "Needless to say, I packed my stuff and left. He tried to call me over a dozen times for the next few days. He finally left me alone when I told him I would get a restraining order and file charges against him for stalking."

This made Richard laugh which, in turn, made his firm belly bounce around. Jake felt his eyes lock onto the large belly and he had to fight the urge to not get a hard on right then and there. Clearing his throat slightly, he stood up and began carefully stuffing all the empty containers into the plastic bags they came in. The raccoon continued to clean up after their meal, even pulling out some sanitizing wipes and running them over the coffee table a few times. All the while the large bear watched him with a small smile on his face.

"You know, you're already better than my last assistant." His voice, while still rough and rumbling, had a softness to it now. "He never would eat with me like this when I offered it to him. As soon as noon hit he was out the door faster than you could blink."

Jake hummed softly before standing up and stuffing the used wipes into the bags of trash. "Maybe he was intimidated by you." He could feel a small blush forming on his face and for the first time in his life, thanked the fact that he was covered in fur so it didn't show. "I mean, a high powered business man like you. Not to mention..." He made a vague up and down gesture that encompassed Richard's whole massive body. "You're not exactly the smallest guy around."

The bear laughed again which was followed by a soft grunt as he pushed himself up from the couch. "Yeah... you're right about that." He slapped at his belly making it bounce a few times. "Not much to be done about that, I'm afraid. I've always been a big guy. If I didn't do the small work out that I do, then it would be all fat and I'd have to be rolled from place to place."

Jake had a quick image of the bear being as round as a ball with hardly the use of his hands or feet, needing a personal assistant not only to help with work, but also to roll him around town. The image made him snort and laugh hard, which only made his blush grow more. He didn't usually like when someone made him laugh so much he snorted. Richard however seemed to find it just as funny and the two quickly were in a fit of full body laughter that lasted for several minutes. Once they got control of themselves again, Jake said good bye to his boss and took the bags of trash out of the office to throw them away. He had a smile on his face for the rest of the work day and it was still on his face when he went home that night.

The next few weeks went by without too much excitement happening. Jake would eat lunch with Richard every day in the big office, with the exception of a few times when the big boss had to work through lunch due to some important meeting or business call. But Jake always made sure that the bear never skipped his meal. He would always leave a decent amount of either take out or something he made at home on the large oak desk. Richard showed his gratitude for the kindness by entrusting the raccoon with more and more important and high profile tasks. On several occasions, he had been sent out in a fancy company car to pick up important clients from hotels or airports and bring them back to the office for their meetings with Mr. Bullion. He was also sent out to pick up the oversized dry cleaning and drop it off either at the bear's large house or bring it back to the office so he would have a spare set in his closet just in case.

Jake's bank account was also starting to feel the gratefulness of the bear. With every biweekly paycheck that he got, his checking and savings account grew larger. He was beginning to have more than he truly knew what to do with. After the end of the third month of working as the bear's personal assistant, he came home and looked around his small apartment and had a thought. He really should move. The small apartment, while not the worst place he'd ever lived, was far too small for him now that he payed attention to it.

So within the course of another few weeks, Jake was moved into a slightly more upscale apartment building. It was still a simple one bedroom, but it had more square footage that included a nice, big living room and even a decent sized dining room. The kitchen had been what sold it for him though. The large space was stocked full with a large fridge, stove and plenty of cabinet space. He was so excited that he even began to bring bigger and better home cooked foods to work for him and Richard to split at lunch time.

Yes, things where going very well for the young raccoon. All except for one small thing. The more time he spent with the large bear and the more he got to know him, the more intense his feelings for the guy became. It quickly got to the point where Jake would wake up in the middle of the night, his crotch covered in cum from yet another intense wet dream involving the bear. He tried with all his might to ignore the urges. After all, not only would it not be proper for him to even try to connect with his boss on that particular level, but from their talks the bear's last encounter with that sort of thing had been with a female leading Jake to the belief that the bear was very much straight as an arrow.

"I just don't know what to do with myself." He complained, slamming his head down on the table of the bar he was at. "No matter what I do I can't fight these feelings I have for him!"

A gentle hand came to rest on his hunched shoulders and a soothing female voice sounded out through the din of the bar. "Oh honey... I'm sorry."

Tilting his head, Jake looked at the female husky that he had met on the bus that fateful day six months ago. The two had talked increasingly over the past few months and she had ascended to the level of his very best female friend. He, in turn, had become the much sought after gay best friend for her, which she told him with delight made all her girlfriends very jealous. She was currently looking down at him with a soft smile and patting his shoulder, trying to find the words to comfort him.

"Office romances don't usually work out, even if both parties are interested." She said, taking a small sip from her apple martini.

"You're one to talk." Jake replied sitting up straight and gesturing over to a tall, well built stallion who was currently standing at the bar, talking with a small group of other males. "Didn't you and Josh meet at work?"

The husky blushed and gave the horse a long loving glance. "Well...I never said it couldn't work out, just that it usually doesn't." She said taking another drink from her glass.

There was a small roar of cheers and boos from the area of the bar as the crowd the horse was in. All were watching with rapied attention to some sports game that was playing on the flat screen above the back wall. Jake rolled his eyes and looked back at the husky. "I just.... I don't know."

"What you need is to get fucked." She said flatly, making the raccoon almost spit out the drink from his own apple martini. He coughed several times, feeling the alcohol burning his throat. Glaring at the female, she tried to hold in a smile and a laugh. "What? You've said it yourself, you haven't dated in almost two years now and I'm guessing it's been about that long since you last let some stud have his way with you."

Jake felt the blush creep over his face and looked away before slumping his shoulders. "Yeah... it's been a while."

"Well then, maybe a good pounding from some sexy stud will get you out of your funk and let you start to think straight again." She drained the last of her drink and looked up at the bar where the tall stallion was standing with a mug of beer in his hand and chugging it while the other males around him egged him on. Bringing her fingers up to her lips she let out a long loud whistle that got the attention of everyone in the bar. When the horse turned to look at her, she dangled the empty glass from her fingers and raised an eye brow. A look of sheepish embarrassment came over the guy and he quickly ordered another drink and rushed over to join them.

Jake sat and talked with them for a while longer before the husky and horse began to get a little to handsy for his taste and he politely excused himself. Time continued to pass for Jake and for the most part he was incredibly happy with how his life was going. He threw himself fully into his work, making sure that every need and want of Richard's was taken care of. He had even joined the bear on a small out of town business trip for a few days which had been a lot of fun. It wasn't until almost seven months into his new position that something bad happened.

One of their major accounts was threatening to take their business somewhere else. If that happened, it would be a massive blow to the company and would result in several thousand people losing there jobs. Richard began to get irritated and angry. Some days he would even stomp through the building and into his office yelling at everyone not to bother him and instructing Jake to not let anyone in or not to transfer any calls to him unless it was from the owner of the account.

This went on for almost a whole week and everyone was feeling the strain. Richard had stopped being his normal cheerful self and began to turn into a slight recluse. He wouldn't even eat the home made meals that Jake brought in for him. The raccoon knew that he wasn't doing these things on purpose. He was just under a lot of stress about keeping the account. The bear's heart was made out of gold and he took every lost job as a personal failure on his part. Jake had seen him almost break down when he had to let go an employee of almost ten years because the board had decided to merge his position with another, meaning that they only needed one person to do both jobs. He had seen none of this behavior when he fired his old assistant but that was probably due to the fact the guy had stolen from the company. The bear had fought against it but the vote had been unanimous and there was nothing he could do.

When the following Monday came around and things still hadn't improved, Jake decided to try and help. Around lunch time he carefully opened the door to the bear's office and stepped inside. His tail curled around his legs nervously and his ears where pinned flat against his head. He saw at the far end of the room, Mr. Bullion hunched over his desk, a scowl on his face and his large fingers typing rapidly over his key board. He didn't even look up when Jake was standing in front of him.

"What?" He growled, not taking his eyes off the screen.

"Um... Mr. Bullion." Jake felt his knees shake slightly and he had to take several deep breaths in order to calm his racing heart. He didn't know if it was the use of his formal name or the small note of fear and apprehension in his voice that finally made the bear look up, but suddenly Jake found himself looking into the over tired and stress filled eyes of his boss. The sight made his heart stop racing and made him feel horrible. The guy looked like he was running on fumes and bad coffee. His fear left him and he could feel his voice evening out.

"When was the last time you slept?" He asked, forgetting what he had been originally going to say. "You look terrible."

"Well golly, thanks." The bear grumbled rubbing at his eyes. "I don't have time to sleep. If I can't find a way to give these fuckers a lower rate on their account while still giving us a profit, then over nine hundred fucking people will be out of work and on the streets!" His voice took on a growl and he clenched his fists tightly. "No matter what I do I can't figure out a way to do it though."

Jake could see the weariness fighting to drag the bear down into a much needed sleep. "Richard..." He said softly, moving over to the other side of the desk and putting a small hand on the bears large shoulder. "You'll never be able to work properly if you don't give yourself time to rest and recover. You're so stressed I bet your blood pressure is through the roof! You need to relax. I'm sure that if you do, you'll be able to find the answer."

"How the fuck am I suppose to relax!?" He growls. "Every time I close my fucking eyes I see all the people I'm letting down! They have families who depend on them and if I don't do something..." He trailed off and grabbed at a mug of old, cold coffee and drained the whole thing. His face scrunched up at the bad taste and he slammed the cup back down causing a small crack in the bottom.

The two stood/sat in silence for a while. Jake racking his brain to try and think of some way to help the guy relax. The raccoon began to go over all the things he does to relax, but quickly throws them all out when he realizes that none of them work fast enough. Well... normally when I need to relax super fast I just jerk off. The thought clicked on a small light bulb and made his heart rate double. He knew of one thing that he could do to help his boss relax. But he didn't think the bear would go for it. A part of him thought that maybe he was just trying to use this as an excuse to get what he wanted from the bear. Maybe he wasn't as pure hearted as he thought if he was thinking of taking advantage of his boss. But then again, it could work. In his experience, not only is it a fast way to relax, but most guys fall asleep right after, which would also help the big bear out.

Taking in a deep breath Jake let it out slowly. "Richard, I think I know a way to help you relax and think straight, maybe even help you sleep."

The bear looked up, his eyes blood shot and looking about ready to drop at any moment. He grunted, apparently not able to form words at the moment. Jake took it as a sign for him to continue. "Just... just bare with me." He placed his hand back on the bear's large shoulder and gently pushed him back until he was reclining in his large leather office chair. The bear put up no resistance, which was a clear sign of just how far out of it he was. Turning the chair slightly, Jake maneuvered his boss until he was facing him. The bear's massive legs where a bit harder to manipulate, but after a moment the raccoon had them spread open.

"Wha... what are you doing?" Richard asked, his voice already husky.

"Shh... don't worry sir." Jake said softly, rubbing the thick muscular thighs. "Everything will be alright." Sinking down onto his knees, Jake began to fumble with the thick belt and zipper of the bear's suit pants. When he had them open, he could smell a heavy musky scent that rushed to his head and instantly made him hard as a rock. He shivered slightly and licked at his suddenly dry lips.

Above him the bear rumbled softly and shifted one of his hands onto his large belly. Taking a few deep breaths, Jake reached into the dark folds of the open fly and began to carefully fish around. He was very surprised to find that Richard didn't wear any underwear, so when he reached inside, his hand instantly brushed against a large thick tube of hot soft flesh. Above him, another long, low moan sounded out. Pulling out the bear's soft shaft, Jake let out a small gasp. The bear's dick wasn't overly long, only about five or six inches. What made him gasp was the thickness of it. Jake had never seen what others call a beer can sized dick before but if he were to guess, Richard had one and then some. Wrapping his hand around the middle of the thick shaft, he found that he was barely able to make his fingers touch. Gulping hard and wondering for a moment if this was truly the smartest thing to do, Jake fished inside the bear's pants again and pulled out his massive testicles.

Each one weighed at least two to three pounds and were the size of oranges. The bear was quite obviously a very potent male. Smacking his lips some more to make sure they were wet, Jake leaned forward and opened his small mouth. The head of the bear's shaft just fit inside his mouth and the moment his tongue touched the sensitive flesh, the taste exploded over it. It was a touch ripe from a day or so of unwashed; but other than that, it had a slight spicey taste to it which seemed to go straight to Jake's cock making it harder than ever before. Closing his lips around the head he began to suck lightly and lick over it trying to wake the sleeping beast.

It didn't take long at all. Within moments, Richard's shaft began to grow harder and harder. Thankfully it stayed the same length and only swelled in thickness by another inch or so. Before Jake really knew it, the shaft was rock hard and leaking pre into his mouth. Sighing happily at finally having the source of his night time emissions in his hands and, more importantly, in his mouth. The raccoon pushed his head forward feeling his lips stretch as he tried to take more of the incredibly thick length into him. He only managed to get two or three inches into his mouth before it threatened to stretch his jaws past the point they could handle.

Deciding to brush off his dusty skills, Jake began to bob his head up and down the length of the shaft, using his hands to jerk off what he couldn't fit inside. A constant series of moans and groans came from the chest and throat of the large bear above him which made Jake very happy, knowing that his actions where having the desired effect. Dropping one of his hands from the shaft, he quickly filled it with the two massive orbs hanging just bellow. They felt heavy and full of cream and he wondered how long it had been since the bear had jerked off. He knew that he hadn't been with anyone in over ten years but Jake wondered if the guy had jerked off in that time frame. He could almost believe that he hadn't from the size and swishing sound coming from deep inside the nuts and he knew that this was going to get pretty messy.

This observation was reinforced when a hard pulse from the shaft sent a large amount of pre into Jake's mouth. It covered his tongue and began to run down the back of his throat and he couldn't help but moan at the taste of it. It had been far too long since he had tasted another males sweetness and he was fully enjoying it. His head began to move faster up and down. The bear's large belly blocked Jake from seeing his face.

Suddenly a heavy pressure slammed onto both sides of his head and it took Jake a moment to realize that it was from Richard's large beefy hands. The bear had apparently gotten enough control of himself to grab hold of the raccoon's head and was even starting to thrust his hips slightly, forcing a little more of his hard, thick length into the too small mouth. Jake began to panic slightly hoping that his boss didn't try and force his whole shaft into his mouth. He doubted that he could take it.

"Oooohhh fuck!" The long low words came from above him. "Fuck Jake that feels amazing!" A small smile tugged at the corners of his mouth at the words. "Fuck I've been dreaming of your sweet little mouth wrapped around my cock since you first came up here!"

Those words took him by surprise. He didn't know if they where truth or just said in the heat of the moment and the bear's sleep deprived mind. For the moment, though, he let himself believe that it was true. Closing his eyes he sucked harder letting Richard thrust into his mouth at his own pace. The bear's thrusting began to get more and more forceful which in turn made more and more of his thick length push into Jake's mouth. Small tears began to form at the corner of his eyes as he felt another inch slide over his tongue. The large flared head of the bear's cock teased against the back of his throat. He almost gagged a few times but thankfully he still remembered enough to control the reflex.

Both hands where now on the bear's large balls and he happily squeezed and rolled them around enjoying the heavy weight of them. A hard pulse from the shaft added with a quick tightening of the ball sack told Jake what was about to happen. The bear's thrusting picked up speed and he began to snarl and snort like a wild animal.

"Oh fuck!" He gasped out. "Here it fucking comes!" His grip on Jake's head tightened slightly and he began to shove in harder, trying to bury every inch of his thickness into the tight wet mouth. He wasn't able to manage the last few inches, however. But with one last hard shove, he roared out and his whole body stiffened and locked up.

Jake's eyes grew wide as the first hard and heavy blast of thick hot bear cum flooded into his mouth. He wasn't even given a choice on if he wanted to swallow or not. Richard's grip on his head was so strong that he had no hope of pulling away. Not that he even wanted to. Happily, Jake began to gulp down the thick and sticky fluid. Rope after heavy rope of cum shot into his mouth from the pulsing cock of his boss. The seed was hotter than any other he had ever known. The taste was unlike anything he had experienced before and it made him moan and groan. Almost a dozen thick shots of cum flowed into his muzzle and down his throat. There was so much that a good amount even began to dribble from the corners of his mouth.

All the while, Richard continued to snort and growl low enjoying the most intense orgasm of his life. After several long minutes the flow of bear seed began to slow down until it was just oozing the last drops out of the large cock head. Jake felt the bear's hands fall away and a moment later a dull thump came out as they hit against the chair. Letting out a soft sight through his nose, Jake suckled on the bear's cock a few more times, making sure to get every last drop from it that he could. His belly was full to busting with heavy seed and the moment his mouth was off the thick bear cock, he let out a small burp that brought the heavenly taste of seed back to his mouth.

Smacking his lips happily he enjoyed the musky taste and shivered with pleasure. His mind was blank with pure bliss at finally fulfilling one of his major fantasies from the past few months. A loud and rumbling snore ripped through the quietness of the office. Jerking his eyes up, Jake saw to his great relief Richard's head reclined back on his chair, his mouth wide open and his eyes closed tightly. Another loud snore came from the bear's open mouth and it made Jake smile. It had worked, he had managed to relax the big guy enough that he finally fell asleep.

Slowly standing up, his belly slightly bloated from the amount of cum it now held, Jake carefully tucked the bear's shrinking cock back into his pants and zipped it up. Walking over to the coffee table, he grabbed the container that held the sanitizing wipes and began a quick clean up of any loose cum that he hadn't been able to drink down. Once he was happy with his appearance and the look of his impromptu work area, he quickly rushed back out to his desk and pulled out a few scented candles. Going back inside the office he placed them on the coffee table and lit them trying to cover up the heavy smell of musk and cum that was quickly spreading through the large room.

Wiping his mouth on the back of his hand he smile hearing another loud snore come from the bear. Carefully shutting the door to the bosses office, he sat down behind his desk and sighed heavily. A large smile spread over his face. He couldn't say for sure how he knew, but Jake was positive that when Mr. Bullion woke up he would feel better than he had in a long time and that he would be able to come up with a way to make everyone happy with the new contract without any one losing their job.

Rubbing over his full stomach, Jake scooted in his desk chair and began typing away at his computer finishing up a small report. A smile on his face and whistling a small tune as he worked.

To be continued.