Office Boy Pt. 01

It was Tuesday morning that started just like any other for Brian. He was a recent grad with an MBA from a respectable school and had started his career at a medium sized firm in the financial sector that spring after graduation. Now getting into early winter he thought he was adapting well to the professional environment.

Brian had just settled into work at his desk this morning when the owner of the firm, Kelly Jones, arrived, walking past his desk she stopped and said good morning.

"Good morning Brian. I see you got that report I had asked you to take care of sent out yesterday afternoon. Thanks for your hard work on that last week." She said.

"Good morning Ms. Jones," he responded, "Thanks for having the confidence in me to get it done."

"You've been doing great here, Brian, I'd knew you'd be up to it. If you get a few minutes this morning come and see me in my office, there may be a few other things we can get you involved in." Kelly smiled and then continued walking to her office in the corner of the floor.

"Will do," Brian responded, his confidence growing to have been noticed by the owner of the firm. He had always been driven by the desire to please those in authority over him.

It had been a fairly simple task just some standard reporting on a few investment accounts to a small group of clients. It was really just a matter of compiling some numbers and providing a bit of analysis. Something he had done numerous times, though in this case Kelly had finally allowed him to proceed without any oversight.

The acknowledgement from his boss made him feel good about the work he had done; but something had been eating at the back of Brian's mind since he had sent the report. He opened the copy in his computer files and began to go through it again, checking against his notes.

"Oh shit!!" He thought when he saw the error. He had transposed two figures which gave his future analysis a much rosier outlook than the investment actually warranted. The clients of his firm stood to lose a lot of money if this wasn't changed. Those investors already had this report and could already be making decisions based on it.

His mind raced to the repercussions. Best case, he thought, he'd be stuck with his immediate superior checking every report and bit of work he did well into the foreseeable future. Worst case, those clients would already be investing based on this report, it may take a few weeks or months but they might start losing a lot of money and he'd lose his job.

"Ms. Jones seems like a reasonable person," Brian thought, "best to own up to this as quick as I can, take responsibility, and we can figure out how to fix it." He quickly printed off a copy of the report and highlighted the mistakes, then headed to Ms. Smith's office in the corner of the floor.

He knocked on the open door of Ms. Smith's office. "Yes?" she said.

Brian stepped into the large office and approached her as she sat at her desk looking through some papers. "Um...Ms. Smith...I...uh...may have made a mistake in the reporting...uh...I sent out last night," he stammered out.

"Yes, I can see that here," Kelly responded sternly, holding up the papers she had been reviewing, "Do you know what this could cost our clients? What it could cost this firm, and more personally me professionally?"

Ms. Jones had always been professional, but friendly with Brian, this sudden anger apparent in her voice, as well as how he had disappointed her rendered him nearly speechless. "Well...I...uhhh...is there...um...a way we can fix this?" Brian stuttered back.

Kelly knew when she had assigned this task to Brian, though they always strove for accuracy, it wasn't as important as it had been made out. He needed to take it seriously but it was a good thing for him to learn with and correct errors moving forward. They would simply need to edit the report and call the small group of clients possibly affected. She even knew this group of clients was not fast to act on anything and there was plenty of time to amend Brian's error.

Brian didn't know this and she looked up at him planning her next steps carefully. Kelly had liked the look of her newish employee from the start. He was different from the typical east coast finance guys. They always seemed short, vaguely mouse like, perhaps a little soft with too much prep school coddling. Her profession, especially as owner of her own firm, was demanding and she didn't have much time to date. The egos of the men from this social circle, as well, clashed with her need to be in charge. From the start Kelly had kept her eye on the tall blond Midwestern boy she had hired.

Kelly again addressed Brian sternly as he looked down at the report in his hand trying to avoid her strict gaze, "You've already sent the report out, haven't you?"

"I...uh...yes miss," he responded.

"I'm not sure what good an employee who can't even be bothered to double check his work is to me and my firm." Kelly said as she stood. She could now see her young employee from head to foot and enjoyed the view of his toned body through his well fitted button down shirt and khakis. She flushed slightly thinking of how she may be able to take advantage of him.

"I...uh...I mean I thought I did. I'm sorry, miss. It won't happen again." Brian finally looked up. His boss stood across from him behind her desk arms crossed just under her breasts wearing a well fitted black pencil dress under a shapely jacket. He noticed her feet slightly apart and how her crossed arms pushed her breasts up. He was easily a foot taller than her, but as soon as his look met her blue eyes fixed in a piercing glare Brian again looked down and away.

"It definitely won't happen again if you don't have a job," Kelly replied. She noted how his head had dropped and his shoulders slouched slightly under her authority. He was the bigger person in the room but she was clearly in charge of the situation.

"Miss, I really am sorry," Brian did some quick mental math on the situation. If he was fired under these circumstances, surely he wouldn't get a good recommendation from Ms. Jones. Without that and having only lasted a few months in his first job out of school; finding a new job would be hard, especially with no other real ties to the industry. Not to mention the embarrassment he began to feel having let his boss down. "I'm sure if I fix the report and let people know we can make sure the damage is limited."

"You know as a woman in this industry I've had to work very hard to get and maintain my professional reputation. An incident like this is completely unacceptable at this firm!" Kelly chided.

"Yes, miss, I can see how that is the case. I can accept full responsibility." Brian pled.

"Oh yes, you'll be taking full responsibility for this. Like I said, though, what good are you as an employee in your current role if you make these sorts of mistakes? I may have to find a role more suited to your assets; after we determine a suitable punishment for this misstep." Kelly said, her plan fully forming now, she looked her young employee up and down. Her face and chest reddened further and a slight dampness formed in her pussy at the thought of how she could use her young male employee.

Great, Brian thought, already about the lowest on the organizational chart due to being the most junior at the firm, now he was sure to have everything he did double checked. At least, it seemed he wasn't going to lose his job.

"Yes, miss, whatever you think is appropriate," he responded finally looking back at Kelly's face noting again her blue eyes and the pale skin framed slightly by a few loose tresses of her dark brown, almost black, hair that hung out of the loose pony tail she had it tied back in.

"That is good to hear," Kelly said as she moved from around her desk and walked slowly over toward the door. Brian followed her with his eyes, turning slightly as she passed and she continued. "You see to reach the status that I have at this young of an age takes commitment." She shut the door to her office and turned back facing Brian once again.

"Yes, miss, I can see that would be the case."

"I don't have much time for socializing, and when I do, the men that I meet, especially in this industry, don't like a woman who wants to be in charge."

"Umm...yes, miss," Brian responded. He was having trouble seeing were this was going, but it was weird that suddenly Ms. Jones dating life was involved he thought. Wait! What is she proposing!? He thought. Brian had never thought of his boss in any way other than as his boss and a professional mentor.

"Now as my employee, you would, of course, not mind me telling you what to do? You wouldn't mind me being in charge?" Kelly asked staring at Brian unyieldingly.

Brian further slouched and reddened with embarrassment. Of course, his boss was in charge he thought, and he wanted to make her happy with his work and efforts in the office.

"This morning I've realized I can't necessarily rely on your ability in the world of finance," she continued, wetting her lips with her tongue as she again assessed the young man in front of her with her eyes, "but it seems I may be able to use you in a different way."

"Do you have a girlfriend, Brian?" She asked, moving back in front of Brian.

Brian was somewhat embarrassed standing in front of his boss since she had taken this authoritative tone. He looked down at the floor between them sheepishly and was thrown by this question. "I...uh...no miss," he responded.

Now, as the questions turned more personal, how he viewed his boss started to evolve in Brian's mind. What was she getting at, Brian thought.

"But, you've been with women before?" Kelly pressed.

Physically Brian was taller and bigger than Kelly, but in this situation Kelly's presence towered over him. He further dropped his head, embarrassed to admit to his limited experience mostly fumbling around with college girls, hoping they would help him, and tell him what to do; only wanting to please them if they would take some authority.

"Uh...I...uh..."

Kelly stepped close to Brian. He tried to look down and away which only meant he first noticed Kelly's breasts in her professional but low cut dress. With this new line of questioning of his "experience," as he noted her breasts pale complexion and how they moved as she breathed; the scent of her slight perfume or body wash from that morning drifted to his nose and Brian briefly thought of how those breasts would feel in his hands. His cock began to respond.

Kelly grabbed his chin and forced his head up firmly. Brian's eyes snapped up and looked into her blue eyes glaring at him. "Well...spit it out, have you been with a woman before?"

"Uh...yes miss a few." Brian finally responded.

She noted how he tried to demur from her stare, embarrassed yet still submitting to her line of questions. Kelly let his chin go and Brian quickly again looked down to the floor. He shifted trying to adjust and hide his growing erection. Though she was probably 10 years older than him, she was very attractive. He noted her lithe body in her well fitted business wear.

"Hmmmm..." Kelly said stepping back slightly, "With your performance on that report I'm not sure you're the best at following easy directions. To perform these new tasks I have in mind you'll need to be able to do that at a minimum."

"I can miss, I can follow directions." He looked up at her now, almost pleading. The way she had taken charge had sparked something inside of him. Embarrassed by the mistake he had made in his job he now just wanted a way, anyway, to make it up to her. To show his boss she didn't need to be disappointed in him.

"Well, I'm not sure." Kelly further pondered. She knew she had him where she wanted him. As Brian watched she looked him up and down, beginning to think of her next steps her pussy continued to wet dampening her panties under her dress.

With his boss's eyes running up and down his body Brian now knew these new tasks entailed something physical. Somewhere from deep in his subconscious he knew he needed to please his boss in whatever way he could and Brian blurted out, "I'll do everything I can to make you happy! To please you miss!!"

Kelly could see the way her young employee's chest rose with his breath and the pleading in his eyes as he pledged this to her.

"Everything you can to please me?"

"Yes miss!"

"Hmmm..." she said, "Well I guess we're going to have to start with seeing if you might be up to that."

Kelly stood a number of feet back in front of Brian still looking him up and down. She hoped his cock met the same standard the rest of his body appeared to set. He was tall and athletic, appeared strong, but not overly muscled.

"Yes, miss, I'll do my best," Brian responded.

"Good, start by getting rid of those pants," she demanded firmly.

Suddenly the full meaning of what was occurring hit Brian and he wavered. "Ummm..." he mumbled out.

"This is not a negotiation!" Kelly firmly stated.

"Yes, m-mm-miss." Brian quavered as he kicked off his shoes. He fumbled with his belt then pushed down his pants. Letting them fall to the ground, he stepped out of them and kicked them slightly aside.

As he stood straight again, Kelly very briefly made out the growing bulge in Brian's boxer briefs before his shirt fell back in front of his crotch. Brian self-consciously shifted under her gaze. She stood across from him hands on her hips feet slightly apart appraising her "new" employee. Brian noted how the pale tops of her breasts heaved with her breathing as they pushed up in the low cut top of her professional dress.

"So far so good, continue with the shirt now." Kelly demanded as she began to slowly walk around Brian looking him up and down as a predator would prey.

Brian unbuttoned his dress shirt, took it off and tossed it aside with his pants. Then he proceeded to lift the plain t-shirt over his head.

Kelly walked slowly around noting his fit but somewhat skinny upper body. Brian's chest and back where pale and there were distinct tan lines on his arms giving him a somewhat boyish look. His legs seemed fit and powerful, however, and his tight boxer briefs shaped his ass nicely.

Brian watched her circle a few times always slightly averting his eyes in deference. Her loose black pony tail fell down on the back of her well fitted coat. He noted her firm breasts and well-shaped ass as she strode confidently around him. He was somewhat embarrassed to be in this situation, nearly fully exposed before his boss, but as she, sexily, almost strutted around him he felt his cock further harden.

She finally stopped behind him taking in the view of Brian standing there nearly naked except for his tight boxer briefs. She approached and ran her hand slowly from just above his ass, around his hip then sliding down he found the bulge of his cock and grasped it. Brian moaned his legs shaking slightly at her touch. His cock was still hardening in her hand as she stroked it slightly assessing its length and width.

Kelly then grabbed his ass tightly she breathed into his ear, "You'll do nicely."

"Mmmmm...yes, miss," Brian moaned as he felt her continue to lightly stroke his cock through the thin cotton of his underwear. He closed his eyes and started to imagine what it would feel like to fuck his boss.

Kelly could feel through his underwear that Brian's cock was nicely proportioned to his 6'-5" height, perhaps even a little larger than she expected, she noted, as she brought him to full hardness. It would be good to feel in her tight pussy that was now fully wet in anticipation and beginning to soak her thin panties. First, though, Brian would need to learn his place, she thought.

"Don't get too excited, boy." Kelly taunted. Her hand slid off Brian's cock and grabbed his balls, quickly squeezing.

Brian's eyes opened as she did he snapped to attention. The pressure on his balls was not too hard but he did not want it to increase much further either. She expertly manipulated them in her hand noting his reaction to slight increases and decreases in pressure as she lead him, tugging on his balls, over to and in front of a plush chair in the seating area of her office.

"On your knees, boy!"

Brian quickly dropped to his knees. His cock strained in his underwear and absentmindedly he began to rub it through the material looking for some relief. Kelly quickly noticed and slapped him hard on the upper arm. "That is not yours to play with anymore, boy! Put your hands behind your back!"

"Yes, Miss." Brian responded moving his hands behind him interlocking his fingers. Kneeling here nearly naked his cock ached for release, but he found himself fully under the sway of his boss.

Kelly walked around him one more time before settling into the chair. She slowly crossed her legs and Brian thought he could make out, just for a moment, the damp gusset of her panties. He licked his lips.

"If you want to stay employed here there are now some new rules," Kelly began.

"Yes, Miss," he replied.

"You will perform all tasks I assign to you without question, whether in a private setting such as this or professional. If you fail to do so, you will be punished."

"Yes, Miss."

"You will now report directly to me and continue to complete office work as I assign." She continued, "I will check your work and if there is a slip up as this morning, you will be punished."

"Yes, Miss."

Kelly now stood for a moment and removed her fitted jacket folding it neatly over the back of the chair. As she sat, Brian could notice her erect nipples through the top of her sleeveless professional dress. Her firm breasts required no bra thanks to the support built into the tight dress. His cock further strained in lust for his bosses body, but more so at the desire to only please her and make amends for his mistakes.

"The most important role you will now take on is to meet my personal needs. As I said, it is hard to meet men in my social circles who can perform as I wish. I will also assign tasks of a personal nature which you will perform without question, or you will be punished." Kelly said her pussy fully wet at the thought of using her new toy.

"Yes, Miss."

"Based on your age, and what I perceive your experience to be from your previous replies and lack of confidence, you will need some training in these matters." Kelly smiled down on Brian, "I will take pleasure in this training."

Brian swallowed deep at this comment; he was unsure if he was ready for this role and doubted wondering what the "training" would entail. Still he looked to his boss confidently sitting in the chair in front of him dictating terms to him. He could not deny his cock was as hard as it had ever been and still the woman he was with was fully clothed.

Kelly now rose and stepped up directly in front of Brian. She bent down again firmly grabbing Brian's chin tilting his head up to meet her gaze as she looked down on him. His head was close to her waist and he began to smell Kelly's heat emanating from under her dress. Brian breathed deep at the first scent and fell further under her spell.

Still holding his head to look up at her Kelly continued, "Finally, and most importantly, your cock now belongs to me."

Brian gasped slightly at this loss of autonomy. Kelly crouched down in front of him, still sat slightly taller than Brian, and reached down between his slightly spread legs she started once again stroking his stiff cock through his underwear and continued, "I decide when and how you get pleasure."

He moaned slightly and Kelly noticed the precum forming and soaking through the thin cotton. "If you follow that rule this will be all we have to mention of it."