Your New Secretary Ch. 02

Author's Note: While I never intended this to be a series, it seems the first chapter really took off. I promise this one has actually been run through a spell check prior to publishing. I struggled thinking up a plot thread I liked for this chapter and went through several ideas. I even started partly writing one before abandoning it. Dana is also a hard character to write for.

***

It was a bright, early Monday morning. James and Dana had carpooled to work after spending their Sunday night together for the first time. Dana had made them dinner and then promptly took James into her bedroom for his regular sexual release. Which, as usual, involved stuffing her throat and pounding her ass. James stepped into the elevator with Dana and shut his eyes, trying to reimagine how she looked bent over her bed, drenched in sweat and spit. Dana couldn't help but notice James spacing out.

"Please try to focus today, James." Dana spoke out in her usual monotone voice. It was enough to shake James awake.

"Of course" was all he replied back, a faint smile still on his face. He couldn't help but feel closer to Dana. Even if their relationship was a strange mix of physical and professional. The two walked into the office, sat down, and started their day. A few hours in, they were all called together for a meeting. James boss, Greg, took the stage.

"It's my pleasure to announce that this year, due to our success in the last major quarter, some of us will be personally attending the biennial systems expo!" The crowd let out a small golf clap. James leaned back against the wall, his mind on other things, like how tight Dana's miniskirt seemed to be today. He could almost make out every curve of her rear end, despite the dark fabric.

"And that's not all! For the first time, we will have our own segment! Yours truly will be discussing projections, and I'm pleased to announce that our very own James has been chosen by the board to give a twenty minute presentation on his recent work!

Another small golf clap filled the room, but James eyes bugged out of his skull. His entire career, he had tried to lay low, and now he was being asked to fly interstate and talk in front of hundreds of people. His vision went hazy, and he felt sick to his stomach. He leaned against the wall for support and forced a smile, but inside he was having a mild panic attack.

Once the meeting was over, he burst into an empty stairwell and clung to the railing, trying to catch his breath. Dana, being the attentive woman she was, followed him in, sensing something was wrong.

"James, are you feeling alright?"

"I'm fine! Fine. Just... I don't want to do this presentation, Dana." James continued to cling to the railing, not even attempting to make eye contact. "There's just no way I can speak to that many people!"

"I understand you may not find public speaking comfortable, but I believe it will be quite helpful for your career. Do not worry; I will accompany you to ensure that everything goes smoothly." Dana replied. James tried to spin around and retort, but Dana had already walked out. And true to her word, that same morning Greg agreed to arrange accommodations for both James and Dana to fly together.

***

They arrived in the city in the afternoon and were greeted by blaring car horns and densely crowded streets. Dana had three bags that were all meticulously packed, while James just rolled a single bag behind him apathetically. The two were dropped off at a hotel alongside some of the higher-ups and were all given their room keys. Thankfully for Dana and James, they shared the same floor. They proceeded to step into an elevator together and began to ride it up.

"We have around 30 minutes to unpack our things and then proceed to our temporary office. Is this time suitable?" Dana looked over at James.

"I guess." Was all James could mutter back. His mind still occupied with how awful his presentation may turn out. Dana pursed her lips, noticing his gloomy demeanor.

"However... I believe no one will question if we are an hour late. Did you wish to use me in my room?" Dana asked, looking over at James with a raised eyebrow.

"No, I'm too tired. I'll just meet you downstairs later for work." James honestly replied. Dana nodded, not expecting to be turned down but equally understanding that James had a fair amount of work ahead of him.

The two went into the office, and Dana helped manage his workload as best she could. She would provide the structure for his presentation, and he would fill it with content. Despite not wanting to do the speech at all, it was clear James wanted to at least ensure it was as good as it could possibly be. His eyes grew heavy as he worked long nights, preparing slides, studying research journals, and compiling his previous works.

A few days passed, and the date of the expo only drew closer. The two had not slept together once since flying to the city, and James attitude around the office and even towards Dana was growing more spiteful. The stress was starting to affect his mental health in a severe way, and Dana was taking notice.

On the final night before the expo, the two rode the elevator back up and began walking to their rooms. Dana once again tried to offer her services.

"James, you seem very overworked. Would you like to join me in my room? I could perform oral or perhaps even-"

"Oh give it a fucking rest, Dana!" James interrupted. "Do you think sex is all I think about? Do you think fucking you is going to make me magically feel better and fix all my problems?"

Dana stared blankly back as James glared at her menacingly, the bags under his eyes on full display.

"Just leave me alone." James muttered with a sad crack in his voice as he walked towards his door, scanned his card, and slammed it behind him.

An hour passed, and James sat at the end of his bed. He wanted to sleep, yet equally feared sleeping as it would accelerate how soon it would bring tomorrow. Suddenly, he heard a knock on the door.

He dragged himself to the door, half expecting to see someone from the hotel staff offering clean sheets. He opened it and was instead met with Dana.

"Hello James, do you have a moment?" Dana calmly asked. A pang of guilt hit James for how he had spoken to her before. So, without saying a word, he slowly nodded his head.

"As your secretary, it's my job to assist you to the best of my abilities. Normally in tense situations, you've taken great relief in more... carnal activities with me." James once again nodded his head, not even attempting to deny it.

However, it seems that in this instance, that may not be enough. So my question to you is, what can I do to help?" Dana leaned forward, as if expecting an answer right away.

Look, I'm sorry for lashing out before. It's just that I'm freaking out over this speech thing. I'm a grown man, and I can't talk to a crowd? That's just embarrassing for someone my age. And then if I fail, I'll make the company look bad, then I'll get fired, and then you'll be out of a job too and-" Dana quickly interrupted James by holding a single hand up.

"James, please take a deep breath slowly, hold it, and then release. Do this three times."

James nodded and began the breathing exercise. He quickly found his own heart rate steadying. As he did, Dana spoke up.

"I can assure you, you will perform adequately. I have seen you give presentations before. Please do not let your imagination run away with you."

James sighed; he knew Dana had a point.

"James, you like burgers, correct?" Dana asked. James nodded, feeling awkwardly like a little kid for doing so.

"There's a well-reviewed burger restaurant a short walk from here. I believe some time away from here will help you. I have a company card we can bill any expenditures to." James lit up hearing that last part.

"Bitching, I could actually go for some grub. Want to come with me?" Asked James.

"That sounds agreeable. I would like to keep an eye on you tonight to ensure you are relaxed at all times."

James reached for his jacket as the two stepped out into the hallway.

***

The pair sat facing each other, waiting for their food. It had been several minutes since the waiter took their order, and not a word was shared between them. Most of the time, the conversations between them were natural. They would either talk about work or when they could next have sex. But now James wasn't sure what to say. Dana continued to glare back at him, almost emotionlessly. Only breaking eye contact to check her watch or to glare at a passing waiter. Finally, James broke the silence.

"So Dana, what do you do in your free time? Any hobbies?" James asked innocuously. Dana paused and titled her head.

"I clean my home, organise my things, and try to attend the gym three times a week." Dana replied back robotically, almost as if mentally reading a script. James let out a sigh.

"Okay, those are fine too... But what do you do for fun? Watch any good TV shows? Read any books?" James leaned forward, hoping to uncover something about her. Dana looked away for a moment and scrunched her face before finally responding.

"No, I don't really do anything like that." Dana continued to stare at James as she took a sip of her water.

"You don't do anything for fun? Yeah, that sounds like you alright. But... don't you get bored? I mean, what's it all for if you don't enjoy it?" James asked, but Dana just gazed back at him, almost confused by his question. James decided to clarify.

"Surely you like something? I like bowling, drinking, music, and-"

"Sex?"

James paused and sighed, nodding his head.

"Well... yeah. I love doing... that... with you. Even if our situation isn't exactly normal. Do you enjoy it?" James asked sincerely.

"James I told you once before, the sex is for your benefit, not mine." Dana replied. James again sighed and rolled his eyes.

"I've got an idea of something you might enjoy after this, in fact, I'd say it's right up your alley." James let out a smile, the first in days, as the waiter finally brought out their food.

***

The two arrived at a late-night bowling alley and approached their lane. James was determined to try to have Dana cut loose while also blowing off some steam himself. James turned to Dana as he tied up his shoes.

"Have you ever bowled before?"

"No. But the rules appear straightforward."

The board lit up with both their names, with James being up first. He stood up, collected his ball, and proceeded to bowl a spare.

"Not a bad start, but I'm a bit rusty. Do you want me to raise the side barriers for you? No shame if it's your first time." Dana shook her head.

"No need. I only see children using the barriers. I don't believe the game will be that difficult."

Dana stood up, adjusted her glasses, and collected her ball. She approached the lane and tried to find her balance on the slippery floor. She lined up her shot, swung her arm back, and rolled her first shot directly into the gutter. She stood there, frozen in place, as it rolled slowly to the end.

"Ah damn. Try not to curve your hand when you release. I'm sure you'll get it next time." Dana nodded and returned to her seat. The match continued, with James scoring decent shots and Dana getting gutterballs every time. Each turn, James would try to offer new advice. Finally, it was Dana's last turn. James decided to go with one last hail mary piece of advice.

"Dana, remember that shitty client we had last quarter? Imagine their face on the first pin." Dana looked at James and nodded before collecting her ball and approaching the alley. She took a deep breath and stood there silently, trying to picture the client's face. Thirty seconds had passed, and Dana still had not yet bowled. James was about to speak up until, finally, she swung her arm back and let loose the ball straight down the middle for a strike. The scoreboard lit up with flames, indicating the bowl speed was on par with expert bowlers.

"Holy shit- you did it!" James yelled, shooting up out of the plastic chair. Dana quickly spun around unsure of what had just happened. She slowly walked back to James, an unusual feeling flooding her system.

"Your first strike! How do you feel?" Asked James, patting her on the shoulder. She looked away and back again.

"Well... I never did like that client."

***

The two walked out of the elevator and back towards their hotel rooms. James hadn't thought of his presentation for hours, and Dana could tell. She felt relieved that she was able to provide some comfort before the big day.

"Hey Dana, are you tired?" Asked James, tilting his head towards her door. Getting his message, she scanned her card, opened the door, and let him into her room.

Mere minutes later, James lay back stark naked in her bed as she crawled between his thighs. She had removed her glasses, let her hair down, and was now running her tongue up the bridge of his semi-erect cock. She sucked one of his balls into her mouth and slowly stroked his increasingly hard cock, maintaining eye contact throughout.

"Fuck... I was mad for turning this down before." James crossed his arms behind his head as he shivered and twitched with each stroke, watching Dana masterfully service his dick. She popped his ball out of her mouth and made her way up to the tip, planting soft kisses before sinking her full lips past the head and down to the base completely.

James bucked his hips, ensuring the full length of his dick was buried in her throat. He even felt her tongue lap at his balls, despite being deep in her mouth. James couldn't hold back; he took hold of her head with both hands and began hammering at her throat, lifting his waist to match each thrust. Dana had her hands at her sides, ready to stop him if things got too rough, but she allowed him to freely use her until, finally, he let loose a week's worth of built-up spunk straight down her gullet. Rope after rope shot out like a water gun, clogging up her throat and mouth.

James moans filled the room as Dana began swallowing as fast as she could. She was used to James loads, but this was unlike anything she had experienced before. Finally, James orgasm began to subside, and he let go of her head, allowing her to emerge for a long gasp for air and to regain her composure.

"Fuck, sorry if I was a little rough. I was starting to see stars."

Dana nodded and reached for a few tissues to wipe her face with as she sat on the side of the bed.

"If that is all, then I will see you tomorrow. Best to get some sleep, James."

James was about to get up, but looking at Dana, he felt a stronger urge than normal to do something for her for a change.

"There's one more thing I want to do." James asked confidently.

"Yes?" Dana replied.

"I want to go down on you." Dana shut her eyes and was ready to re-explain their arrangement, but James quickly elaborated.

"I get it; you have sex for my benefit, not yours. So do this for me too. It will make me really happy and relieved to know I at least tried to do something nice for you." James leaned forward, wide-eyed, hoping for Dana to oblige.

"...Very well. You have ten minutes."

Dana stood up and began to undress, shimmying out of her mini skirt and then unceremoniously dropping her white underwear to the floor. James caught a quick glimpse of her shapely pear ass before she laid down on the bed beside him. Despite her still being dressed from the waist up, James wasted no time getting between her legs and getting an up-close view of her pussy for the first time.

Despite the limited light, James feasted his eyes on Dana's vagina. She was surprisingly completely smooth, which was fine with James as he started kissing up Dana's thighs. Rather than just go in headfirst, he began to try his best to give her the attention she deserved by going slowly and savoring every moment.

"Nine minutes." Dana announced, staring at the ceiling with her eyes half shut.

James, quickly realising the slow approach may not work, dove his face into her pussy and ran his tongue up her lips until he ran over the bump that was her clit. He started lashing at it at different speeds and patterns. Alternating between slow, fast, vertical, horizontal, and even shapes. He was determined to make her feel good.

As for Dana, she continued to stare at the ceiling with a blank expression on her face. Only commenting when another minute had passed.

"Three minutes."

James refused to give up and kept eating her out with as much enthusiasm as he could summon. Until, without warning, Dana's thighs lifted up and smushed James face into place. James tried to pull back in shock but failed, and found he was completely stuck. He tried to call out to Dana but she didn't respond. With this angle, he couldn't see her face, but through her strong thighs, he overheard her say something he never thought he'd hear her say.

"Harder."

James tried to bring his tongue up to lick her clit again, but she kept her thighs locked tight. Dana's hand suddenly gripped a handful of James hair and smushed his face even harder into her cunt. James didn't even have to move, as Dana was now just grinding against his face eagerly. James let his tongue stay buried in her pussy as he relinquished control. He's not sure how many minutes went by like this; all he remembers is trying his best to breathe until finally he felt her pussy tighten up and spasm on his tongue. Her thighs tightened around his face, as did her grip on his hair. James could feel his vision going darker and darker, until he completely passed out.

***

James woke up the next morning beside Dana, still in her room. His body had been shifted upward, so he was lying parallel to Dana. Despite his groggy state, he smiled to himself, remembering the amazing night they shared. He rolled over and fished his phone out of his pocket checking the time. James had slept in; the presentation was starting in thirty minutes.

James spun around and shook Dana's shoulder. Dana's eyes started opening slowly at first before her body clock jolted her awake. She didn't even look at James as she made a mad dash to pick up her clothes around the room.

"James, you have 30 seconds to get dressed before we're out the door. Hurry." Dana urged.

The two scrambled out the door, down the escalator, and onto the main street. And unfortunately for them, the roads were jammed from corner to corner. Cars lined up as far as the pair could see. Just getting a taxi wouldn't work. Dana's eyes then honed in on an alternative: An electric scooter for hire.

After a quick scan with her phone, the two were off. Dana drove the scooter down the street with James holding onto her waist for dear life. And on a few occasions, he grabbed a handful of her chest to retain his balance.

"The presentation starts in under 6 minutes! We'll never make it!" James shouted over the wind pushing them back. Dana ignored him and continued to fly down the street.

***

The two burst into the back of the auditorium and were instantly met by stagehands asking where they had been and if James was ready to go on. Thankfully, the presenter before him had unintentionally gone overtime, giving the two just enough wiggle room to make it. James stood on the side with Dana, waiting to go up.

"Key notes will be presented on the screens in front of you on your left and right. Be sure to talk slowly and make eye contact." Dana reminded him.

"I know, I know. It's just- I'm no less nervous about doing this." James groaned. Dana however quickly spun him around.

"You will be fine. We have created an excellent presentation together." Dana reassured him.

"But I'm still not good at talking to crowds." James responded meekly.

"James, even if you're not good at talking, you're still very good with your tongue." Dana replied, and sudden memories of last night flooded into his mind.