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Dan the Personal Assistant

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Dan fiddled with the cufflink on his shirt. Nervous would be an understatement for how he was feeling at the moment. He absolutely cannot mess this up.

Sitting in the waiting area, Dan glanced over to see his competition. All the other applicants seemed way more suitable for the job. They looked poised, calm, confident. Ready to start the job immediately. Meanwhile his hair was still a curly mess, his cheap shirt crumpled. He wasn’t sure how he passed the first round of application if these people around him were what the company was looking for.

He’d arrived later than he was supposed to and missed his interview slot, so he was expected to be turned away immediately. But apparently the company President still wanted to meet him, so there he was, about to go for his first job interview in a year. He might finally be employed again. Properly employed, instead of working random odd jobs just to survive. He watched as the final applicant before him entered the room.

Dan gulped, running through common interview questions in his head. What are his strengths? Nothing. What are his weaknesses? Everything? Was his job submission video even good enough to be able to get into this round? He could barely remember what he said in the video. He must’ve bullshitted his way through it and now he has to go even further down the spiral of lies he’d created.

Hell, Dan could barely remember even submitting the video. All he knew was that he was drunk on the final day to submit it, and his phone reminder set off to yell at him to submit it while he was enjoying a lazy drunken jack off. Dan had quickly emailed his submission so he could go back to masturbating, but til this moment he hadn’t checked if his email was proper and formal enough. He didn’t care, he must’ve done it right since he was there now anyway.

He almost jumped out of his seat when the door opened. The applicant before him gave a polite nod, and he nodded back. 

Get yourself together, damn it, Dan thought, If you can bullshit your way this far, you can certainly do it in there. He walked up to the door and knocked on it, mustering up as much confidence as he could.

He heard a faint Come in, and slowly opened the door to enter the room.

“Have a seat, Mr Howell,” The company President smiled at him.

“Th-thank you,” Dan stumbled and quickly sat down.

The boss didn’t look as intimidating as Dan had thought he would be. He wasn’t old, as he would expect an accountant with his own successful company to be. Perhaps in his mid-thirties, so just a little over ten years older than Dan. His smile was comforting, welcoming. And Dan couldn’t help but be transfixed by his striking blue eyes. Dan found himself relaxing into the seat. 

“So Mr Howell, first of all, congrats on passing the first round,” Mr Lester spoke, leaning back in his chair a little, “I quite enjoyed your video. You made it entertaining, unlike most submissions.”

Dan smiled, thanking him again.

“But I do feel like I still don’t know you well enough from the video itself. So maybe we can start this off with, why do you want this job?”

Dan cleared his throat a little. He was sure that he’d explained this part in his video, and he hadn’t prepared answers that were different to his video.

“Well, I did mention in the video that I think I’m suitable to be your assistant because I am meticulous. I, uh,” Dan paused, trying to come up with more half truths and recall what he’d mentioned in his video.

Mr Lester looked at him intently throughout his explanation, running his eyes up and down his face as if trying to memorise every little freckle and blemish. If it wasn’t an interview, Dan would’ve thought that Mr Lester was perhaps checking him out a little.

“Interesting,” Mr Lester offered after Dan finished speaking, “You explained that in your video? I must have missed that part then.”

Dan mentally slapped himself. The boss certainly did not sound like he bought his explanation.

“Yes I would definitely need my admin assistant to be meticulous, it’s probably the most important trait that they need to have in an accounting firm. Some applicants try out for this job when they’re the complete opposite of that,” Mr Lester shook his head and chuckled.

Dan didn’t know how to respond to that so he just chuckled uncomfortably back.

“I mean, I’ve received wrong formats of the video submission. Wrong versions. Many applicants coming to me crying and apologizing and asking me to accept a newer version. There’s no room for such mistakes in this company!”

Dan agreed, although now he was starting to get intimidated. He was slowly accepting the fact that he wouldn’t get the job, and he’d totally be fine with it. He was admittedly a careless person who could risk causing this man problems with his accounts, and he did not need that kind of trouble in his life, no matter how badly he needed the money.

“One person,” Mr Lester chuckled, a mischievous glint in his eye, “even sent me a porn video of himself!”

“What?” Dan laughed, feeling horrified on behalf of that poor applicant.

Mr Lester held eye contact with him, making Dan feel small but somehow he couldn’t look away.

“I know right? I don’t know if he was aware of it at all, because he still hasn’t gotten back to me about it. Do you think those type of people are meticulous?”

Dan shook his head no, unsure where this interview was heading. Was there a need to talk about other applicants like this?

Mr Lester was silent, and Dan bit on his lip. Was he supposed to elaborate on his answer or something?

“Yeah no, I don’t think meticulous is a word to describe that kind of person,” Dan voiced it out in case the boss wanted to hear it instead of just seeing him shake his head.

“Then why did you call yourself meticulous?” Mr Lester’s voice dropped low, deep and intimidating.

But Dan didn’t understand his question. His confusion must have been clear on his face as Mr Lester looked slightly amused. The boss silently turned his computer screen to Dan’s direction.

Mr Lester looked on in amusement as the expression on the boy in front of him changed from confusion to horror in a matter of seconds. The colour drained from his face and his mouth fell open as he sat frozen in his seat.

On the computer screen was Dan having a threesome. A threesome that he had had the day before the video submission deadline. A threesome that he’d watched while jacking off drunk before being interrupted by his phone reminding him to submit his video.

“Oh, my favourite part’s coming,” Mr Lester said very casually.

Fuck. Dan wanted to die right there. This cannot be real. Perhaps if he pinched himself hard enough, he’d wake up from this nightmare. He wanted to leave immediately but his legs couldn’t even work.

Mr Lester’s favourite part of the video was apparently when Dan managed to ride two dicks at once. Dan in the video was moaning loud as he bounced on top of one man, another man flush against his back.

“I-I gotta-” Dan managed to utter as he shakily got up, tripping over his own feet at an attempt to rush out.

This cannot be happening. How had he managed to send that video instead? Dan wanted the ground to swallow him up.

“It’s a shame you gotta go because I was about to hire you!”

Dan froze for a second time. Was this man kidding? Wasn’t the humiliation enough already, now he gotta go even further in his convoluted way of teaching Dan a lesson on meticulousness?

“Was gonna give you a higher salary than the job you originally applied for, too.” 

“What do you mean?” Dan asked softly, daring himself to turn back to the boss.

“Sit back down and allow me to explain.”

Dan sighed. He wasn’t sure if he was able to face the man - the company’s fucking President - who watched him take two dicks up his ass ever again. But at the same time, his rent was overdue and he really needed the money.

He slowly sat back down but avoided eye contact, looking at his lap instead of the boss.

“I never expected to receive something like your video submission, but I am actually impressed by it, so I’m offering you to be my assistant. Not for admin though. Personal assistant, if you know what I mean,” Mr Lester leaned forward, looking dead serious.

Dan couldn’t believe what he was hearing. Was he being offered a job as a personal whore? Did this man really think Dan had no dignity in him?

“Like your personal whore or something?” Dan couldn’t help but sound offended.

“Well it does sound bad if you put it like that,” Phil chuckled sheepishly, “Let’s stick to personal assistant, yeah? I can give you a 5 figure salary for it.”

With the mention of money, Dan realised that he really did have zero dignity left.


 

Mr Lester took hiring him very seriously. Dan was given a contract and 3 days to read it all and sign it. He’d actually already accepted the job immediately, but Mr Lester really wanted to make sure that Dan knew what he was getting into even though he was excited that Dan was willing to do it.

Phil’s personal assistant, Dan read the top of the contract. He wondered if he would be Phil’s first ever PA, or if Phil got tired of his last one and Dan was lucky enough to accidentally submit his porn. Or if he had more PAs that Dan would be having threesomes with one day.

Reading the contract gave Dan the realisation that Phil was one kinky man. He wasn’t complaining though, he loved most of the kinks listed, and for 10 grand, he was willing to try out anything. Phil being hot was an added bonus, and Dan was honestly worried about how his first thought upon reading the kinks was that he wouldn’t mind doing it for Phil even if he wasn’t getting paid.

Dan returned to the office the next day with the signed contract, even though Phil kept asking him to give a proper think if he really wanted to do it.

But Dan really did want to do it. If he’s good at anything at all, it was sex. He would definitely enjoy this job more than some boring admin job. And why would he turn down getting paid to do what he’s good at, plus with the most attractive man he’s ever met?

Phil was more than delighted when he was finally assured that Dan was serious about accepting the offer. He sent Dan home with some instructions to start his first day of work proper the next day.


 

Dan had to come in an hour earlier than everyone else in the office everyday, in case Phil wanted a quickie before starting his day. Dan wondered why a man as rich and handsome as Phil doesn’t have a partner. But he didn’t dwell on it, he’s lucky that Phil was single because if not he might not have this job.

For once, Dan actually arrived on time. He was to go straight to Phil’s room, and he’d been given the key. He locked himself in the room, not sure if the rest of the office was meant to know his presence. Was he going to be Phil’s little secret? Or was Phil going to share him with other bored colleagues? He felt a tingle of excitement thinking about it.

Dan walked around the room, taking in the sight of his new workplace which he didn’t get to do much of during his other visits. Phil’s desk was huge at one end of the room. The walls of the room were all glass, overlooking the city. Dan gulped as he looked at the view, remembering that exhibition kink was listed in his contract. 

There were three little couches and a small coffee table in the centre of the room, and at the end of the room was a little pantry. There was even a connecting bathroom, which Dan was grateful for because he certainly did not want to have to leave the room and face other people in the office if he needed to pee.

Dan was standing in the mini pantry contemplating whether it was acceptable of him to make a coffee without permission on his first day of work when the door swung open.

He turned around in surprise, but relaxed when he saw Phil sauntering in.

“Good morning,” Dan said softly. He knew Phil was a nice man, but he can’t help still feeling a little intimidated by him.

“Good morning, Dan,” Phil smiled brightly at him, and Dan wondered how one can be so cheerful this early in the morning.

“Excited to start your new job?” Phil asked cheekily, smirking at Dan.

Dan blushed, but he couldn’t deny that he was excited, so he nodded shyly.

“Well then first things first, you need to be in proper attire. Your uniform, if you will,” Phil spoke as he busied himself to put away his bag and papers that he was carrying.

Dan looked on curiously, wondering what his uniform was. All blood rushed to his cheeks when Phil continued speaking.

“Strip.”

Dan looked at Phil wide eyed, he didn’t expect to be naked at all times. But the idea of it was very hot, and Dan gave a small nod before turning to head to the bathroom.

“Where are you going?” Phil asked, “Do it here.”

Dan’s cheeks were so warm he wondered if it was possible to blush this much. Phil was leaning against the desk, looking at him expectantly. Dan guessed that he should probably throw whatever little dignity he had left out of the glass wall, and he slowly started unbuttoning his shirt.

“Don’t worry, I won’t let anyone see you. Unless you want to. And except any unfortunate people spying into our window,” Phil chuckled, but his gaze was intense on Dan’s now naked top.

Dan awkwardly let his shirt fall to the floor, and his trousers followed suit. Lastly, he took off his underwear and awkwardly held it in front of his crotch. He glanced up shyly to see Phil smirking at him.

Phil walked up to him and took his underwear out of his hands.

“No need to hide anything,” Phil spoke as he circled Dan, observing his boy.

“Good to see that you’ve followed my instructions,” Phil commented, taking note of how well shaven his assistant’s body was.

When Phil seemed satisfied with what he saw, he went back to lean against his desk again.

“This is how I expect to see you every morning, understand?”

“Yes, Sir,” Dan replied, feeling like it was only appropriate to address his boss as such.

Phil smiled, seemingly approving of being called Sir. He instructed Dan to keep his clothes in a drawer under the coffee table, and Dan hurriedly did so before standing awkwardly in front of his boss again.

Phil was now sat behind his desk, and Dan felt so exposed and vulnerable. He would be lying if he said it wasn’t turning him on. He willed himself not to get a boner this early in his job, it’d be embarrassing.

“Well we’ve still got a bit of time before the office opens. How’s about you show me how qualified you are for this job?” Phil said suggestively, rolling his chair back a bit.

Dan walked over and knelt between Phil’s legs, already guessing where this was going. He stared up at Phil innocently, awaiting instructions.

“Good boy,” Phil breathed, and nodded to give Dan permission to continue.

Dan slowly unzipped Phil’s pants. He’d done this many times in his life, and judging from all his random hookups, he was good at it. But he suddenly felt too aware of all his actions, felt like he really needed to do his best. Perhaps it was because he was getting paid for it this time and he did not want Phil to think he’s wasting money on someone who can’t even give a proper blowjob.

He gently tucked Phil out of his underwear, licking his lips when he saw that Phil was already half hard. He looked back up at Phil for approval. He wanted nothing more than to suck on Phil immediately. Maybe he is a cockslut, and what about it? But he thought that it was only right to let Phil take the lead, so he waited.

Phil gently threaded his hand through Dan’s curls and slowly guided his head to his cock, encouraging him with a smile. He’d watched Dan’s video more times than he’d like to admit, and ever since he saw Dan giving the two other men blowjobs, he couldn’t wait to get that pretty mouth around his own cock.

Dan happily went down, suckling on the tip. He hummed when Phil stroked his hair, loving the gentle touches. He tentatively brought his hand up and slowly wrapped it around the length that wasn’t in his mouth. Encouraged by a breathy moan by Phil, he started to suck further down.

Dan began bobbing his head, hollowing his cheeks and licking the underside of Phil’s shaft. He held the base of Phil’s cock as he sucked. Dan had given plenty of blowjobs before, but he probably only ever encountered someone as big as Phil once or twice. He tried his best to go as far down as he could, but he couldn’t fit all of Phil in his mouth.

To compensate for the lack of deepthroating abilities, Dan fondled Phil’s balls and stroked the parts he couldn’t fit in his mouth. He started to worry that Phil might find him disappointing for not being able to suck all of him in. He even wondered if he was going to get fired.

But Phil was enjoying all of it, moaning every time Dan moved up and licked his slit before going back down.

“You’re really good at this, boy,” Phil complimented, and Dan almost keened at the praise.

All of Dan’s worries disappeared upon hearing his boss praise him, and feeling his hand tangle in his hair. Dan hummed gratefully. Phil could easily push his head down to force him to take all of him in, but he liked how instead of that, Phil was being really tender with him. Perhaps this job was going to be the easiest and most fun he’d ever have.

After a while, Dan went off of Phil completely for some air, lips smacking with a pop sound. He looked up at Phil with doe eyes as he stroked him. The sight of his boss staring down at him through half lidded eyes and panting through his slightly open mouth was perhaps the most beautiful sight Dan had ever seen.

Dan gave kitten licks to Phil’s tip, all the way down to his crotch and back up again before going to suck on him properly again. Phil was throbbing and heavy against Dan’s tongue, and he sucked harder to help Phil reach his orgasm faster.

Phil moaned at the sight below him. The boy’s a natural, he thought. He was so glad that Dan had accepted the job offer, and at the moment he felt like the luckiest person in the world to have come across Dan.

He felt his orgasm approaching, but resisted the urge to fuck into the boy’s mouth. He wanted to go slow on their first day, treat him gently. Once Dan got used to this new job, he’d then gradually go harder and push his limits.

So Phil just tugged on Dan’s hair lightly and muttered a warning that he was close. Dan hummed around him, the vibrations sending shivers down his spine.

Dan could taste the salty precum as he moved faster down Phil’s cock. He swallowed around him a couple of times, earning groans from Phil.

“Gonna come, boy,” Phil warned, voice gravelly.

That signalled Dan to suck harder as one hand massaged Phil’s balls while the other stroked the base of Phil’s cock.

With a tug of Dan’s hair and a loud moan, Phil came down Dan’s throat. Dan swallowed it all, breathing harshly through his nose. He continued sucking on Phil until he couldn’t feel any more cum spurt down his mouth.

Dan only got off of Phil when Phil’s grip on his hair loosened. A string of spit and cum connected Phil’s tip to his reddened bottom lip, and Phil chuckled fondly at the sight.

‘i’m so glad I hired you,” Phil slurred, and Dan smiled shyly.

Dan had gone hard from giving the blowjob, but he barely noticed his own need to come until now. He wasn’t sure if asking to return the favour was a good idea, or if he was even allowed to touch himself. His contract did state that he was only allowed to do things when given permission, so he just sat on his heels with his palms flat on his thighs.

“I promise I’ll try to do better next time, you’re just so. Big,” Dan admitted softly, cheeks turning pink.

“Oh I definitely expect you to get better with time, but don’t worry because I’ll make sure you’ll have enough practice,” Phil smirked, “but you did really good for your first time, you were more meticulous than I expected.”

Dan rolled his eyes fondly at Phil’s praise at the end.

“Well, I better get started on my work. That was a good start to the day,” Phil ruffled Dan’s hair as he spoke.

“Uh,” Dan tried to articulate his need to come by pointing to his own hard on.

Phil chuckled down at him, “You’re getting paid to get me off, not yourself.”

And just like that his intimidating boss was back, Dan thought, and he regretted even trying to ask him for help.

“No touching yourself, got it? I’ll decide when you’ve earned it.”

Dan gulped, “Yes, Sir.”

Phil laughed a little, “Aww don’t look so worried. You’ve definitely been good enough so far to earn yourself an orgasm, but I’m afraid I don’t have time to help you out right now. Perhaps during lunch.”

Dan hoped he’d be able to control himself that long. Perhaps this job wasn’t going to be as easy as he thought earlier.

“You’re free to do whatever in here when you’re not needed. Hide in the bathroom if someone’s about to enter, or not if you don’t care for other people seeing you naked.”


 

Dan ended up spending his time sitting on the rug near Phil’s desk and dozing off. He was still feeling a little conscious about being fully naked in front of his boss, so he mostly sat in front of the desk where Phil could barely see his crotch.

Phil was too busy to even make small talk, but Dan didn’t mind. He enjoyed the comfortable silence that was only broken by Phil typing on the keyboard.

His boner died down soon enough, but he spent lunch receiving the best handjob he’d ever gotten in his life. He was embarrassed to have came all over his boss’s hand, but Phil merely chuckled and called him cute.

“It’s alright, boy, there’s nothing to be embarrassed about. You’ll get used to all this soon enough,” Phil had reassured him.

The rest of the day went by fairly quickly and Dan only had to hide in the bathroom once. Before he knew it, it was time to get dressed and head home.

Dan was certain that he was going to enjoy his new job. He couldn’t wait for the next day already. He can’t believe his fuck up and not being meticulous enough actually paid off.