Your New Secretary

Author's Note: I've revised this story from top to bottom to address all the spelling mistakes and structural problems I could find. I've gotten quite a few comments from people who seem really frustrated by my grammar. And some who are just agitated by the story's content. I'm a new writer, and an amateur at that, who does this for fun. I make mistakes. And my aim is to write stories that I enjoy reading.

***

"Morning James, Have you met Dana? She'll be your new secretary."

"Huh?" Was all James could muster out, lifting his tired head from the dimly lit laptop screen. He had pulled another all-nighter, and its effects were obvious. He had sunken eyes, a slow response time, and a yawn that just wouldn't cease, but he had never experienced audible hallucinations until now.

"Did you not get the email? As a new member of the senior staff, you are now entitled to have your very own secretary. She'll sit next to you and help out with your day-to-day scheduling." Explained James boss Greg through a corporate fake smile. Dana stepped forwards and stretched out her hand.

"Nice to meet you, James. I look forward to working with you." She asserted herself both coldly and clearly. There was not a hint of a smile on her face or anything even remotely resembling emotion. Just a thousand yards straight into James's soul. However, she was far from off-putting. She had her black hair done up in a bun, wore a fitting business dress, and had some cute glasses on with sharp frames. The only blemish was a small beauty mark on her left cheek. For a secretary, she put in much more effort than she needed to.

"Same here, Dana." I said, lazily reaching out my hand and shaking hers.

She sat down next to James and began to unpack her things. A laptop, pens, and various notebooks. James was unsure why he needed a secretary and was quite nervous at the idea. He had always considered his job to be easier than everyone realised. And having someone work closely with him meant that someone would be in on just how little work goes into his day-to-day life. It wasn't long before Dana spoke up.

"I've downloaded your calendar and can see you have a meeting at 4:00 PM. Has the work been completed for that meeting?" James leant over, and sure enough, he did have a meeting booked. However, the work would take him an hour at most, and it was still early in the morning.

"Oh yeah, that. I'll work on that in a bit, don't worry." He replied casually, not wanting to rush things and focusing on trying to wake up his tired brain.

"And what time might that be? I would also like to schedule some time to discuss your overall work schedule. I believe there are numerous optimisations that you could make in order to increase your efficiency." She commanded. James stared at her, almost stunned.

On the first day of working together, was she going to try to dictate his entire workflow? Of course not, he thought to himself. This new secretary was clearly more trouble than she was worth so far for James.

***

Dana continued to pester James throughout the week. If work wasn't completed, he would be sent reminders every 15 minutes on the dot. If there was an email he had yet to reply to, she would pester him about how he would like her to respond. It seemed like just managing his own secretary had become his job.

James was beginning to crack and considered his options. He could tell his boss? But surely they would be insulted and probe him as to why he didn't want a secretary. He couldn't risk losing this job. Maybe he could sit her down and try to explain to her that this wasn't his prefered way of handling things? But that would cause some awkward conversation about what he does with the rest of his time during the day. The truth is that he was listening to music or watching TV on his phone.

Monday morning came, and fatigue hit James once again like a truck. He dragged himself to work and sat down a few minutes later, which was enough to prompt a line of questioning from his secretary.

"James, you're 7 minutes late. Was there traffic? Or was something wrong with your car?" She probed.

"There's nothing wrong... just traffic..." James groaned, too tired to even try to sound convincing.

He expected her to dig deeper, but instead she got up without saying a word and entered the kitchen. A few minutes later, she returned with a hot cup of coffee.

"Here you are, James. I saw you make it once and memorised your preferences. I hope it is acceptable." She lowered the cup on my desk on a coaster that, strangely, wasn't there on Friday night. I took a sip, and sure enough, it was just how I normally make it.

"Thanks, Dana; I appreciate it." James replied, genuinely thankful for a change.

"While you drink that, I was hoping we could discuss why you were awake between the hours of 11PM and 4AM last night." She asked innocuously. James whipped his head towards her, now on his toes and a bit defensive.

"Why do you think that?" James replied slowly, feeling like he was suddenly on trial.

"Because, you have the work messaging application on your phone, and it showed me that your phone was still online between those hours last night. This isn't the first time this has happened, as I have been documenting your sleep schedule over the last week. Are there problems at home that keep you from sleeping? Dana asked inquisitively. James was offended, to say the least.

"I don't exactly appreciate being spied on." James said, ready to step up from his desk and march to his boss, Greg. It didn't matter if he outed himself anymore. He considered this woman insane.

"I understand it is not comfortable, but my role is to assist you in any way I can. I believe for the good of this company and your role here, we should discuss it openly. Why are you up so late?"

"It's none of your business! I can work on a little sleep just fine. You can see that, can't you?" James retorted.

"Your proficiency at work is admirable, but it can be improved if you get more rest. Tell me, do you stay up late to view pornography on your phone?" Dana asked, keeping the same blank stare that she always did. James was taken aback.

"W-What?! That's absurd, and again, it's none of your business what I do in my spare time!" James hissed back through clenched teeth. He made sure to keep his voice low, considering just how volatile this was becoming. He didn't want to suddenly be blamed for aggressive workplace behaviour.

Dana kept a stern gaze at James. He looked back and locked eyes for a few seconds. Her gaze was too much for him, and he looked away as if confessing her assumption to be true.

"I see. James, this cannot continue. If you keep feeding this habit, it will affect your job more and more. We must correct this. Do you have a partner?" James impotent, rage-filled silence answered her question.

"Very well. Then, if you can assure me you will get a full night's sleep, as your secretary, I will assist you in this matter to the best of my abilities." James stood there, staring at her. Until a moment ago, he was ready to kick his boss's door down and demand she be moved to a different department. But now all he could think about was, "Just what did she mean by assisting me?"

"...Excuse me?" Was all James could muster, before being cut off again by Dana.

"5PM. I will keep your schedule clear. Until then, you have work to do."

***

The clock ticked over to 4:59 PM. James had quite an unproductive day. Dana was being her usual overbearing self, but that wasn't the case. He kept replaying in his mind what exactly she meant by assist.

5 PM stuck, and like clockwork, Dana approached him.

"James, please follow me." Dana asked in her typical cold tone.

James timidly got out of his desk and followed her down the hall, around some bends, and finally to an empty, vacant office.

"Sit." Is all Dana said, motioning her head towards an old two-seater couch. James slowly walked towards it and parked himself squarely against the arm rest on one side.

Dana, on the other hand, was still pacing around the room, doing small robotic tasks. She had turned the shutters completely closed, so no one could peer into the room. The blinds looking out into the parking lot had also been completely drawn shut. The only source of light was now a small lamp in the corner of the room. Dana approached the door and turned the latch, preventing anyone from the outside from barging in. Dana then walked straight towards James.

"You may remove your pants." She coldly instructed.

"Now hold on a fucking minute, Dana. I want to talk. Just what the hell is going on? You drag me here; barricade us in. Just... what the fuck?" James wasn't the best with words, but he feels he managed to get the gist of how he felt out to Dana.

"It's my job to help make sure you work at 100% efficiency, James. Correct?" Dana said, tilting her head as if confused by the pushback. James nodded.

"I understand that to some women, that would mean just helping you handle your emails and your meetings. But I operate... differently." Dana's eyes looked away, For the first time, James saw an emotion he hadn't glimpsed in Dana before. Insecurity.

"If I can see a way to improve the habits of someone I work for, then I will see to it that it is done. Answer me this, James. If you had a girlfriend, would you stay up late watching pornography on your smartphone? Or would you sleep with her instead?" Dana quizzed. James realised that, in a way, she was right. The porn was somewhat of a quick fix for his physical needs.

"James, I cannot force you to do anything you do not want to do. But just know that, as your secretary, there is very little I won't do to help you. Do not hesitate to ask. If the result is a higher standard of work, I will see to it that it is done. No questions asked." Dana explained, with some faint hints of tenderness in her voice.

"I... I see." James managed to spit out. He felt his heart racing. He didn't know what to think anymore. He still thought she was insane. But maybe a more respectful type of insane.

"So, if you do want me to assist you in this sort of way, You need only ask me. Otherwise, I am content to open the blinds and act like this conversation did not occur between us." Dana froze and stared James down. A moment of panic struck James like a lightning bolt as he realised the ball was in his court. And if he didn't answer soon, she would walk out.

Moments passed in silence until Dana began walking back towards the blinds to re-open them. Until she was cut off by James.

"Blow me."

Another cold silence filled the room. Dana stared at James for a moment. Was this all some sort of trick to catch James on grounds of sexual harassment?

Dana walked towards James, her hips swaying ever so slightly, until she was exactly in front of him, looking down.

"Very well." Was all Dana said back, squatting down in front of James and undoing his belt. James couldn't believe what was really happening.

His belt was undone with almost surgical precision, and his fly went with it. With one quick tug, his pants were now around his ankles, leaving him in his boxers. She repeated the same motion with his boxers as his cock flopped out unceremoniously. James tried to relax back onto the couch and calm himself down as Dana took his member with one hand and peeled back his foreskin. She could see a few specks of dick cheese around the head of his cock.

"S-Sorry. I meant to shower this morning, but I had to rush, and I-" Was all James could say before what happened next.

Dana had opened her mouth, wrapped her lips around his entire head, and began sucking like an industrial vacuum. Her tongue swirled around his cock, cleaning every inch of it. Slurping sounds filled the room as the once trim and proper secretary began sucking like a pro, complete with enough lewd noises to put the most hardcore of hentai to shame.

"H-Holy SHIT!" Exclaimed James, throwing his head back as Dana continued to suck him off like her life depended on it. One hand massaged his balls while another helped guide his cock into her mouth. Dana had increased her speed, and his once flaccid cock was now scraping the back of her throat. She pushed herself even deeper, until both her lips were kissing the base. She had very little gag reflex, despite James's generous size.

James moans and various expletives echoed through the small office. He shivered and raised his lips as if trying to breed her mouth. It wasn't long until he felt his own orgasm peek out on the horizon. He shut his eyes and threw his head back as he began to cum, not holding anything back.

Dana, sensing this, lifted her mouth up to the head and flicked her tongue at his frenulum as he shot rope after rope of thick spunk into her mouth. After the sixth and final spurt, James's orgasm began to subside, and he sank back into the couch, utterly spent.

Dana moved herself off James's cock and, rather than swallow, began to swish the cum around her mouth as if sampling wine. The thick, porridge-like reward clung to the corners of her mouth. Finally, she shut her eyes and gulped loudly, having to swallow a few times just to ensure it all went down. She looked at her reflection in the window and began lifting off the stray pubic hairs glued to her cheeks. As she did this, she finally spoke up.

"I expect to see you fully rested tomorrow." Was all Dana said before lifting herself back to her feet and fixing her attire, which was now somewhat ruffled. In his groggy state, James lifted back his boxers and pants and relooped his belt. In a minute, the two walked out together to the parking lot, where they finally parted ways. It wasn't until James was in his car that he realised that the only thing he wanted to do when he got home was go to bed.

***

This relationship had been ongoing for a month, and almost once a day, Dana would find time to give James a blowjob. The two would confidently walk to an empty office in the late afternoon, and Dana would perform her secret extra duties as secretary. There were times when the offices would be locked or unavailable, and Dana offered alternate solutions. On one occasion, the two managed to get away with oral sex in a seldom-used disabled bathroom. On another, Dana guided James to the backseat of her car, parked somewhere secluded around the corner, and made him cum so hard that some came out of her nose. But in typical fashion, she would simply lap it back up, swallow, and regain her composure.

To say James's performance improved would be an understatement. His sleep schedule was solid, and his work output was overflowing. In just a month, he had gone from one of the lesser-known workers to one of the most reliable in the company. There was even speculation that he would earn the somewhat coveted employee of the month award.

But like most men, James got used to his pleasure and slowly grew to crave more.

***

"I'm afraid sex is out of the question." Dana said coldly, tying back her hair in a bun in preparation for her daily oral services.

"Why? We've already gone this far." James asked back.

"Because I am saving myself for my future husband. Research shows that suitors prefer partners who are virgins, so I have taken great pains to remain one. I do not want to lose the opportunity for a profitable partnership if the chance presents itself." Dana replied. James could only stare in bewilderment.

"You're a strange woman, Dana. What about anal?"

"That's fine." Was all she replied.

Minutes later, Dana was bent over the desk with her legs spread wide. James didn't waste the chance to savour an eyeful of her rear before he popped her anal cherry. He took two hands and spread her two pale cheeks apart. Her asshole had a slight brown tinge but was very neat, with a small freckle on one side. He lowered his gaze to her pussy and noticed she was covering it with one hand. Not masturbating, but preventing James from getting sidetracked by the wrong hole. Or rather, the right one.

Dana had blown James for a few minutes, and he was slick with spit, hard as diamonds, and ready to go. With one hand on her hip and another on his cock, he positioned himself at her starfish and slowly pushed. He could feel the muscles keeping him out slowly begin to recede and make way, until finally the head of his prick slipped in.

"Fuck you're tight. How are you holding up?" James asked. Despite the odd relationship the two had, James never wanted to hurt her. He looked at the back of her head and saw her nod almost uncaringly. He began to look away but noticed her hand on the desk was in the shape of a claw, digging into the wood for dear life. Dana wouldn't admit it, but this hurt.

James took that as his cue to slow down and let her adjust. He stood there with his cockhead in her ass for a few minutes until he noticed her hand slowly relax. He took that as his sign to push more in and would stop when her hand took that familiar claw shape and dug into the wood. It took almost 10 minutes, but finally he was completely inside her rear.

"It's completely in..." was all James could say. The squeezing and contractions of her ass were almost begging him to cum, despite just standing still. Dana simply let out a slight nod. When suddenly a ringtone filled the room.

"My apologies, James. Mind if I take this? You will not need to stop, but I will ask you to please be quiet." James was taken aback at how calm she sounded for someone whose ass was gaping wide open. He nodded, and she lifted her phone to her ear.

"Good evening, James office; who may I be speaking to?" Small chatter could be heard on the other end. James realised it sounded like a client of some sort who wanted to reschedule a meeting.

"Of course we can do Tuesday instead to review the specs." Dana continued. Idle chatter still going back and forth. James grew impatient and boldly withdrew his cock halfway out and sank it back in. Dana's composure didn't change, nor did the tone in her voice. He took this as a sign she could handle herself and started to really fuck Dana's ass.

Her entire body jostled forwards with each thrust. The amount of fat around her waist, despite her thin figure, was rippling with each plough. This was all too much for James, as he already began to feel his orgasm building.

"Mind if I put you on hold while I log your request? Thank you, one moment." Dana said, hitting the mute button on her phone. She gently placed it down and looked back at James for a brief moment in a way that communicated "Let me take over" without having to say anything.

James slowed down his thrusts and stood there, catching his breath but still firmly inside her. Dana placed both hands flat on the desk and began throwing her ass back onto his cock. Each twerk created a large slapping sound between them as his cock plunged in and out of her anal cavity. James could only hold onto her ass for support as her twerking made him climax balls deep in her buttocks. Dana, sensing this, pushed back as hard as she could to ensure she wouldn't spill any on the carpet. Once she was sure James was empty, she unmuted her phone and rested it against her head and shoulders so she could talk hands-free.

"Are you still there? Thank you for waiting; I just want to confirm a few final things with you." Were the last things James heard her say as she walked out. She had simply pulled up her leggings and underwear and rolled her dress back down. James saw her walk past their colleagues, and they were all completely unaware of how his cum was currently staining the seat of her underwear.

***

And so, the two continued to fornicate over the next few months. James had his choice of her mouth or her ass, but never her pussy. He had simply accepted that such a hole was just too off limits and did not want to risk biting the hand that feeds.