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.
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.
yes I know I still have incomplete fics from last year but what do yall think about turning this into a series too? lmao let me know if I should continue it!
(tho I can't promise that updates will be frequent!)
Let's pretend I didn't just change the title of this fic......
(See the end of the chapter for more notes.)
The next day, Phil walked into his office to see his personal assistant already naked, awkwardly sat on the rug in front of his desk. He smiled a little, liking how the boy was naturally submissive without him even instructing. He still seemed nervous, and Phil hoped that he would get used to his new job sooner. He’d try his best to make his boy comfortable, it’s no fun playing with someone who was hesitant anyway.
“Good morning, Daniel,” Phil spoke up as he set his bag down.
Something about the way Phil said his full name out sent tingles down Dan’s spine. He was already excited for the day despite not being sure what exactly was in store for him.
“Good morning, Sir,” he responded quietly from where he was sat.
Dan didn’t know what he should do after he stripped when he entered earlier, so he decided to just wait in the same spot he sat on the previous day. He kind of wished there were steps to follow, like how was he supposed to act when his boss enters? He didn’t think even this could be hard. Perhaps he was overthinking, because it didn’t seem as if his boss was unhappy with him just sitting there. In fact, Phil’s face seemed to have softened when he laid eyes on him. Or maybe Dan was overthinking that too. He chewed on his bottom lip and twiddled his thumbs as he waited for some, any instructions.
Phil wanted to train Dan to be able to take all of him, and judging from the previous day, Dan was equally eager to be able to do a proper job. He would still go slow on his boy, based on how nervous he seemed. Even though Phil wanted nothing more than to shove himself down the boy’s warm throat. He just kept telling himself that he’d have lots of time for that once Dan was trained proper, he didn’t have to worry. Despite how nervous and awkward Dan looks, Phil felt sure that Dan wouldn’t be quitting any time soon.
“Could you be a darling and make me a cup of coffee please?” Phil requested as he settled down at his desk.
Dan nodded and hurriedly stood up, rushing to the mini pantry. Phil looked on at his beautiful view of his assistant’s perky butt. He couldn’t wait to fuck that ass raw, but he had to be patient.
Meanwhile, Dan was having a near meltdown trying to make his boss’s coffee. He was just too damn shy to ask how Phil would like it. After staring at the sugar and creamer waiting for some sort of direction from Phil that didn’t come, he decided to just leave it black and bring the sugar along.
He knows that his boss was really nice, but he still couldn’t shake the nervous energy off. Perhaps it was due to the vulnerability of being stark naked in front of such an important man, or how he really did not want to screw up and risk losing this weird as hell job.
“I uh,” Dan awkwardly gestured at the sugar packets after setting the cup down.
“Two next time, thank you,” Phil smiled up at him.
Dan nodded, making a mental note.
“C’mere,” Phil beckoned, and Dan timidly knelt before him.
“I’m gonna train you to take all of me, alright?” Phil asked, brushing back the curls on his boy’s head.
Dan nodded, keen on showing his boss that he can definitely do better than the previous day.
“Whoa not yet,” Phil chuckled when Dan moved to unzip his pants.
Dan quickly retracted his hand. Damn it he should’ve known to wait for permission.
“Get under the table. And get comfy, you’re gonna be there a while.”
Phil left as Dan crawled under the desk. The desk was so huge that there was enough space for him to sit up on his heels under it. Before Dan could start wondering where his boss went, Phil returned with one of the cushions from the couches.
Phil placed the cushion on the floor and Dan gratefully kneeled on it. As Phil sat down and bracketed him, Dan realised he had a view of only his boss’s crotch. He was effectively in between Phil’s legs, and he could barely see anything else. He peeked up and saw Phil staring back down at him.
“You’re going to be my lil cockwarmer today, yeah? No sucking. No blowjobs, just keep as much of me in that pretty mouth for as long as you can.”
Dan swallowed, already getting turned on by the idea. He slowly unzipped Phil’s pants when finally given permission, and tucked Phil out of his underwear.
“Stay still. Only move off when you really need to, understand?”
"Yes, Sir,” Dan spoke quietly before moving to wrap his lips around Phil’s head.
“Remember the safe gesture?”
They’d come to an agreement on their safewords and safe gestures in the contract. Dan snapped his fingers twice, and Phil nodded, looking pleased.
Phil was only half hard, so Dan easily got all of him in his mouth. He pressed his nose against Phil’s crotch, tickled by pubes. But he was determined to show his boss that he could do better, so he relaxed his jaw and stayed still.
As time ticked by, Dan found that it was getting harder to keep still. Phil was steadily growing in his mouth and he could feel his lips being stretched around the base of Phil’s cock. Dan breathed heavily through his nose and tried his best not to give him any stimulation, just letting his cock rest heavily on his tongue.
When Phil finally got fully hard, Dan felt his tip hit the back of his throat and had to move back a little. He could feel his gag reflex acting up and did not want to gag on his boss on only his second day of work.
Phil didn’t pay attention to him one bit. At one point, Dan even heard him make a phone call. Dan wondered how Phil was able to concentrate on his work when he’s hard and throbbing in Dan’s mouth.
Dan had given a fair share of blowjobs in his life, but he’d never been a literal cocksleeve before. He shifted his weight on the cushion uncomfortably, wondering how much time had passed, how much more time will pass before he’d be let off.
He tried to slowly move back down until his nose pressed against Phil’s crotch again, but couldn’t reach there just yet. He swallowed, and that was the first time Phil looked down at him since the start of the scene.
“When I told you to stay still I mean it. No stimulation at all, got it?”
Dan’s eyes widened and he tried his best to nod. A little saliva dribbled out the corner of his mouth just then, and Phil gave the smallest fond smile before returning his attention to his work.
Soon, Dan’s jaw began to ache. Without being able to swallow, he was drooling uncontrollably down his neck. He still tried his best to reach the base of his boss’s cock, but he couldn’t last longer than a few seconds before having to shift back a bit. This was the only movement that Phil seemed to be okay with, and he supposed that this was the purpose of the task after all. He hoped that he’d soon be able to take all of Phil in without having a gag reflex.
Dan was very hard as well. He hadn’t known that being used like this turned him on this much, plus the lack of attention from his boss made it even hotter.
His toes felt numb, and his knees and jaw were aching. He so badly wanted to touch himself, or to shift his position just a bit. But above all that, he wanted to be good for his boss. So he remained still and dug his nails into his thighs so as not to touch himself. He hoped that he’d be worthy of an orgasm later.
Dan ignored his aches as best as he could, focusing instead on the weight resting on his tongue, on breathing steadily through his nose, on his boss’s musky scent. He ignored the scratchy feeling forming at the back of his throat and instead focused on relaxing his throat further to keep trying to take all of his boss in his mouth. Dan closed his eyes as he fell into a rhythm of taking all of Phil in his mouth until Phil’s tip grazed the back of his throat, until his nose pressed against Phil’s crotch for a few seconds before moving back a bit. He tried to stay longer every time he moved back down.
As Dan moved back down, feeling Phil’s tip hit the back of his throat again, precum unexpectedly leaked. Dan sputtered and coughed, moving off of Phil entirely as his gag reflex kicked in. Phil looked down at him, looking a little concerned.
“Woops, sorry about that. Do you need to stop?” Phil asked, moving back a bit to give Dan some room.
Dan didn’t want to stop, though. He didn’t want to until he perfected being able to deepthroat his boss. It’s almost become a pride thing; he didn’t want to give up and be only average at what he’s supposedly best at.
“No no I’m sorry,” Dan spoke, voice rough and scratchy, as he quickly sat back up to get Phil’s cock back in his mouth.
Phil threaded his hand through Dan’s hair as Dan settled down again. Dan enjoyed how Phil rested his hand gently on his head for a while. In that moment, he realised that he had never wanted to seek approval from someone as much as he did from his boss. He wanted to do his best, as he felt that his boss only deserved the best. And right now he felt that his current best was not enough.
So Dan ended up staying still for almost another half hour. He was honestly impressed that Phil could stay hard in his mouth for that long. Right after another phone call, Phil brought his attention to the boy between his legs again.
Dan blinked up at his boss, eyes teary. He was sure that he looked a mess; he felt flushed and had saliva and sweat running down his chest and pooling on his crotch mixed with his own precum.
“You look so pretty like this, your lips so nicely stretched around me,” Phil commented softly, tracing a finger on Dan’s obscenely stretched red lips.
Dan whined low, Phil’s voice and praise turning him on immensely. He loved how even though he was technically just being used, his boss didn’t make it feel that way.
“Guess I’ve teased you long enough, huh?”
Dan nodded and continued whining. His boss’s musky scent was intoxicating and it was driving him crazy how he couldn’t just swirl his tongue around the throbbing weight in his mouth, how he couldn’t suck and swallow around it.
But apparently his boss wasn’t going to give him what he wanted, as he moved back and off of Dan completely. Dan moved forward to chase after his cock almost instinctively, but Phil gripped his hair loosely and held him in place.
Dan licked his lips, looking desperately at the cock slick with his saliva in front of him.
“I wanna see if you’re as good with your hands as you are with your mouth,” Phil explained, pulling on Dan’s hair a little to tilt his head up to look at him.
“Yes, Sir,” he replied, his throat feeling a little sore as he spoke.
He knelt up, wrapping one hand on the base of Phil’s cock. He began to stroke Phil’s cock, twisting his wrist on the upstrokes and thumbing on the tip. His other hand wrapped around Phil’s full balls, cradling it. He gradually quickened his strokes, noting the way Phil’s breathing got heavier.
“Feels so good, boy,” Phil encouraged, resisting the urge to buck his hips into Dan’s hand.
Phil couldn’t possibly last much longer, especially after spending about an hour in Dan’s mouth. He warned his boy that he was close, which only made Dan speed up his movements even more.
Dan squeezed the base of Phil’s cock, giving the right amount of pressure and friction that he knew would drive anyone crazy. And just as he predicted, Phil came all over his hands. He looked up as he continued stroking his boss through his orgasm, hands now slick with cum. He observed how Phil’s eyes shut and mouth dropped in pleasure, how he groaned low in his throat and how his chest rose and fell rapidly.
Phil looked down at his boy through half lidded eyes as he came down from his high. Dan suddenly felt bold as the striking blue eyes landed on him again, and he let go of Phil’s softening cock to bring his hand up to his mouth. He stared up at his boss with wide innocent eyes and began to lick his hand clean, lapping up his boss’s cum.
Phil felt as if his breath was knocked out of his chest when he saw what Dan was doing. The sight was so hot that he felt as if he could come again.
“You like that, boy? Tasting my cum on your hands,” Phil asked, voice slurred.
“Uh-huh,” Dan whimpered and nodded, making a show of sucking each of his fingers clean.
“God, you’re so hot,” Phil uttered under his breath, but Dan heard it loud and clear and hid his smile behind his hand.
“Well done boy, that was so good. You did so good I’m proud of you,” Phil praised, stroking Dan’s sweaty curls.
“Thank you, Sir,” Dan almost purred, leaning up into Phil’s hand in his hair.
“Go clean up,” Phil said as he noticed how Dan’s chest was glistening with his drool and drying precum.
He helped Dan steady himself as he stood on shaky legs. He deliberately ignored Dan’s hard on, amused by Dan’s slightly disappointed expression when he realised he wasn’t getting rewarded immediately.
But Dan obeyed his boss’s instructions and cleaned up in the toilet, trying his best not to just jerk off in there. When he went back out, Phil was already focused on his computer, so he decided to read the newspaper laid out on the coffee table to distract himself from his hard on.
By lunchtime, he’d gone completely soft so Phil didn’t bother helping him out like he did the day before. Dan would ask for it but he knew his place, and strangely he found that helping his boss orgasm was somehow satisfying enough even if he won’t get the same pleasure in return.
Phil asked Dan to come along with him for lunch but Dan was certain that no one outside the room was aware of his presence, so it’d be weird if he were to suddenly emerge from the room and he wasn’t ready to face that situation yet. So Dan opt to stay in Phil’s room and Phil brought back lunch for him. Phil apparently did not care if people knew about him or not, which made Dan wonder if he did have personal assistants before. He’d have to ask about it when he found the right time.
Dan realised he got bored real easy. Phil mostly used him in the mornings, and he always had nothing to do after lunch. Of course he couldn’t expect Phil to be playing with him throughout the entire day - he had an actual job to do. But Dan didn’t complain, couldn’t complain. Not when he was being paid so much to have sex and then just sit around and look pretty. He couldn’t help but wish that Phil wasn’t taking things this slow, though. Based on his contract, he knew that Phil wasn’t even making him do 10% of what was required of him. Not yet, anyway. He couldn’t wait to move on to all the kinks listed on it.
But Phil seemed determined to train his mouth before going any further. The next day, Dan spent his morning on his knees being a cockwarmer again. This time, Phil fastened a spider gag on him, opening his mouth wider and leaving him no choice but to lock his jaw in place. Dan didn’t like how he couldn’t wrap his lips around Phil’s cock, but he did feel his gag reflex slowly going away.
He did enjoy how Phil was slowly starting to go a bit rough on him. He was still very gentle; hand lingering on his hair and soft strokes on his cheek. But he also tugged on his hair a little more, even pushing his head down to the base of his cock and keeping him still there for a while. Dan moaned throughout, loving the new treatment and hoping his response would encourage Phil to go rough on him more often. He did love Phil’s soft touches, but deep down he was simply a masochist who craved for someone like Phil to dom him completely.
Phil had ordered him to jerk himself off in front of him afterwards. Dan was painfully shy at first, but then he tried to ignore the fact that Phil was his fucking boss, and instead pretended that he was just another hot hook up. Phil had certainly enjoyed the show Dan put on for him, full of desperate whining as he stroked himself on the rug until he came all over his stomach.
The rest of the week went pretty much the same. Dan found it easy to fall into routine. Enter the office, strip, sit on the floor. Greet his boss when he arrives, make him coffee, slip under his desk. Train his gag reflex away to take all of his boss in his mouth. Spend the rest of the day just chilling and drinking hot tea to soothe his throat. Occasionally help fetch items from the other end of the room when his boss asks him to. Leave only when the coast is clear at the end of the day.
Before Dan knew it, two weeks flew by and he was successfully able to deepthroat his boss without his gag reflex anymore. Dan was a little surprised that he made it this far without screwing anything up. His boss seemed happy with him, and he was also warming up to the man real quick. He was glad that all the nervous energy surrounding him at the beginning was wearing off as he got used to his out of the ordinary job.
On days when Phil didn’t grant him any relief at work, he’d spend his night jerking off to the memories of Phil using him earlier in the day and the image of how he wishes Phil would use him. And if he allowed his mind to entertain forbidden thoughts long enough, he’d admit into the darkness of his room that maybe, maybe he’s starting to fall for his boss.
Thank you for all the love on the first chapter and I hope you enjoyed this one too :)
Dan cursed himself as he ran towards the office. His head was still pounding from his hangover, but it was the least of his worries at the moment. He knew he shouldn’t have gone to the club the night before, he knew it was a bad idea. And yet there he went, back on his bullshit again. He’d been doing so well on his job the past weeks as well. The last thing he wanted was to disappoint Mr Lester.
He rushed into the office, stopping in his tracks when he realised that there were already people in. He was so used to being the first in. He avoided eye contact with everyone, keeping his head down as he walked hurriedly to the big door at the end of the office. He felt curious eyes on him and wondered if anyone already guessed right who he was, his place in this office.
He put his key into the lock of the door to his boss’s office only to find it already unlocked. Dan gulped, slowly turning the doorknob. He had no idea how his boss would react to him being an hour late. He really should’ve just stayed home and called in sick. Why didn’t he think of that earlier? Damn it.
Dan quietly stepped inside, and saw Phil already sitting at his desk. Phil didn’t bother to even look at him. Dan bit his lip anxiously, somehow feeling even more disappointed in himself when he noticed that Phil already made his coffee himself. He stood quietly, waiting for Phil to say something. But Phil continued ignoring him so he had no choice but to speak up first.
“G-good morning,” Dan’s voice was barely above a whisper.
“Care to explain?” Phil answered, still not looking at him.
“I’m s-sorry Sir I.. Overslept,” Dan stuttered, still standing by the door.
Phil finally turned towards him, but his nonchalant look made Dan even more nervous.
“You remember what’s stated in the contract for not following my rules?”
“Y-yeah uh, a punishment you deem fit,” Dan answered, his heart beating fast as he wondered what sort of punishments Phil would mean.
“Strip and bend over my desk,” Phil sighed and got up, sounding almost annoyed.
Dan gulped as he quickly got rid of all his clothes, then he placed his palms flat on his boss’s desk and bent a little, his ass feeling exposed.
Phil had gone to take something out of a drawer at the side of the room. As he slowly walked back to his boy, he could see just how nervous he was. He stood behind Dan, so close that his shirt almost brushed against Dan’s skin. He noticed how Dan was trembling slightly. Without warning, he grabbed onto Dan’s hair and pushed him down, until Dan’s cheek was pressed against the cool surface of the table and he was properly bent at the hips.
“This is what I mean by bend over.”
Dan winced a little when Phil grabbed his hair, not expecting to be pushed down. Phil’s voice was so authoritative and Dan knew he was getting punished so was it weird that he was getting turned on by this?
“Yes, Sir,” he whispered belatedly.
Phil stood by the side Dan was facing away from. He twisted the paddle in his hands, studying the pretty freckles dotted around his boy’s back. He softly rested the paddle against his boy’s bum, just to let him guess what he was going to be punished with. He heard a gasp so soft it was almost inaudible, but it only got him more excited.
So perhaps Phil was a sadist who had been waiting for his boy to slip up somehow just to have a reason to spank him. But Dan had been a near perfect sub since day one, and although he was disappointed when he opened his door to an empty office earlier, it quickly turned into anticipation to finally be able to punish his sub. He loved how obedient Dan was, but he also loved having to deal with occasional moments of rule breaking too.
He rubbed the paddle across Dan’s ass for a bit, tapping it lightly to build up the anticipation. His soft taps gradually grew into the first actual hit, the sound of the smack resonating around the room.
Dan bit his lip at the first spank, biting back a whimper. He’d been spanked before, but never as a punishment. In fact, he’d never been punished before; he’d never had a relationship with a Dom. Playful spankings with random hookups couldn’t compare to the emotions that tie in with the spanking he’s facing now. He felt his cheeks heat up, and he couldn’t decide if this was all more enjoyable or humiliating.
At that command, Dan decided that it was both equally humiliating and enjoyable, and he didn’t even know it was possible.
“One,” his voice was unintentionally shaky.
Almost immediately, the paddle landed on his ass again. Dan gasped and jerked forward into the desk a little at the unexpected hit.
Phil’s assertive voice caused the hair on the back of Dan’s neck to stand. He cleared his throat and made sure to be louder as he said Two.
Dan grit his teeth throughout the spanking. He so badly wanted to rub his sore ass or touch his hard dick, but he clenched his fists on the desk instead. He couldn’t quite believe how incredibly turned on he was. Were punishments meant to be enjoyed?
Phil didn’t hold back on his swing. He loved the way his boy’s ass bloomed pink. He loved the little gasps and muted moans, the way his boy jerked forward a little at each hit. He especially loved how his boy was so hard and leaking, clearly enjoying his punishment.
Halfway through the spanking, Dan found himself tearing up. From the pain or humiliation or the guilt of disappointing his boss, he wasn’t sure. He’d never experienced such an emotional spanking before, and the newness of it all was overwhelming. He sniffled a little before gasping out a Ten.
Phil was impressed with how well his boy was taking the punishment. He was accepting it quietly instead of giving any protests that Phil was expecting. Dan didn’t even try to block the spanking with his hand or rub at his sore ass, which Phil had experienced with his old subs before. In fact, Dan even stuck his ass out a little more whether he realised it or not, definitely eager to receive the next hit. Phil was in awe with his obedience, and he knew that Dan definitely was not late on purpose.
He alternated the spanks between each cheek, watching Dan’s plump ass bounce from the impact. Phil could hear little sniffles, and was happy that the point of the punishment was coming across.
“Twenty,” Dan moaned out, the stinging pain on his ass ironically shooting pleasure up his spine and straight to his cock.
Dan felt the paddle being placed on his back. He sighed when his boss’s hand started rubbing on the sore skin, soft and soothing touches that calmed him down. His hand felt cold against his warm and red skin.
“Next time I should give you one for each minute you’re late,” Phil’s voice was still harsh unlike his gentle touches.
“I’m really sorry Sir, I didn’t mean to be late,” Dan whined pathetically.
Phil removed the paddle from Dan’s back and placed it on the desk. He held onto Dan’s shoulder and pulled him to stand straight and face him.
Phil’s heart leapt at the sight of his boy. They were the same height but somehow Dan seemed smaller, especially with the way he hunched in on himself. Dan looked up at Phil guiltily through red rimmed eyes. His bottom lip was a matching red from being bitten so hard during his punishment. His dick was throbbing but still he was being a good boy keeping his hands by his sides, not even moving back to rub his sore ass. Phil loved the sight of his poor boy in front of him. Fuck, I really am a sadist, he thought.
Phil opened his arms welcomingly and brought his boy into a hug. He rubbed his back softly and threaded his other hand through his boy’s curls, gently pushing his head down to rest on his shoulder.
Dan stood pliant for a moment, but as he adjusted to the stark contrast of these soft touches compared to the harsh spanking mere moments before, he slowly brought his hands up and meekly wrapped them around his boss’s waist. He sniffled into Phil’s shoulder, breathing in the cologne he’d become so familiar with.
“You did really well for your first punishment,” Phil praised softly into his ear as he rubbed circles into his boy’s back.
“Thank you,” Dan whispered, “I promise I won’t be late again, Sir.”
“I trust that you won’t,” Phil replied as he let go of Dan.
Dan stared up into the icy blue eyes. But he could see warmth in them, maybe fondness and if he dared himself to think about it, even love. He subconsciously moved closer, their faces so close that he could feel Phil’s breath on his nose.
But as Phil stepped back, he realised that of course Phil wasn’t going to kiss him. He wiped his cheeks, mentally scolding himself for even thinking about a kiss. Why would Phil kiss him when he’s technically just an employee.
“I’ll let you rest now, yeah?” Phil said, already sitting back down at his desk.
Dan nodded, mumbling a thanks. He went to sit at the couch by the coffee table, but realised quickly that the scratchy material against his tender ass wasn’t a good idea. So, he awkwardly moved to lie on his stomach on the rug.
But that was a bad idea too. The friction of the rug against his dick was so sweet, and he instinctively started to grind down onto the rug. He kept his movements small so as not to alert his boss even though it was barely enough.
Phil ignored Dan for a while, letting his boy think that he wasn’t aware of what he’s doing. No matter how small his hip movements are, Phil could clearly see and hear what Dan was doing. He always left Dan alone but he did keep an eye on him, and Dan was oblivious most of the time to his hyper awareness of what his boy was up to.
After a few minutes of Dan struggling to get off on the rug, Phil finally decided to pipe up.
“Was the punishment not enough? Do you need a reminder of another rule?”
Dan gasped and scrambled to sit up. His sore ass grazed the rough material of the rug but he could barely feel it when he was now in shock that he’d been caught. But honestly he should’ve known how unsubtle he was being. Phil’s gaze was still focused on his computer.
“N-no Sir,” Dan answered softly, “I’m sorry.”
His dick twitched at the sudden lack of stimulation. He clenched his fists at his sides to keep from touching himself.
“I’ll let it slide,” Phil side-eyed him, “for today.”
Dan blinked, feeling his eyes water. He really did not mean to be naughty. He’d been on his best behaviour since the first day, and he was disappointed in himself for suddenly breaking rules today. He really shouldn’t have gone drinking yesterday, damn it.
He sat in silence, not caring that his ass still felt tingles of pain against the rug. He used to go to bars or clubs every weekend, getting random hookups for the hell of it, mainly to cover up his loneliness for the night. But no matter how much he’s sticking to that reason for going back last night, he damn well knew that it wasn’t the case anymore.
He’d gone there to take his mind off of Phil. His fucking boss. Who he absolutely cannot fall for. But it just got worse when he started comparing the men there to Phil, and thinking how they’re all no match to Phil. He realised that all he wanted was Phil. And for some reason he felt like if he were to carry on with a one night stand, it’d be as if he’d be cheating on Phil. Which he knew is silly, because for all he knew, Phil could be having random hook ups on the weekends too. But he still felt wrong. So he opt for the next best option: to drink his thoughts away.
Now his hangover was slowly disappearing, but all he’s left with is a strange feeling for his boss that he couldn’t quite describe. He barely knew his boss still. He knew him pretty well in terms of his turn ons, his sensitive spots, the way his breathing goes ragged when he’s about to come. But he didn’t know a single thing about this man’s life outside the office. How the hell could he be falling for someone who was technically a stranger?
And Dan was sure that his feelings weren’t mutual anyway. If anything, the little rejection of his kiss earlier confirmed it. So he had to be professional and just suck it up and do his job. The less he dwelled on it, the better. So he busied himself with scrolling through social media on the rug to let the time pass.
Phil always invited Dan out to lunch, but Dan always refused. He still didn’t want to go out and face the other people in the office, especially now that some already saw him this morning. So Phil would always bring back lunch for him, sometimes even just ordering in and spending his whole lunchtime with him.
Today, Phil ordered in again and they were sat around the coffee table eating their pasta.
“Why do you always spend your lunch with me when you could be out with your other colleagues?” Dan asked quietly, not sure where the thought came from but needing to know the answer.
“If you wanna be alone I can leave for lunch next time,” Phil said, and Dan couldn’t tell if he heard a hint of hurt in Phil’s voice or if he imagined it.
“No I mean… I don’t know, isn’t it boring to stay in here all day? I’m not exactly much fun company anyway,” Dan said, twisting his fork into his pasta.
“I like your company, Dan. Even when it’s quiet. I like how we don’t have to fill the silence with small talk all the time, like what I’d have to face with the people out there,” Phil made a face of disgust, “Anyway I’m their boss. They’d hate for their boss to join in their free time.”
“True,” Dan nodded, recalling awkward lunches with old bosses.
“It’s the same for you, isn’t it? I should’ve taken the hint,” Phil sighed.
“No no that’s not what I meant at all! I just asked because I didn’t want you to feel obliged to keep me company,” Dan quickly explained. He’d much rather have his boss’s company than be alone during lunch, but he just didn’t want to feel like a burden.
Phil nodded and smiled a little, and the conversation ended there. What used to be comfortable silence between them now felt awkward, and Dan regretted even opening his mouth in the first place.
Dan felt too awkward to not try to ease the tension in the air, so he decided to start another conversation.
“So..I realised we kinda don’t even know each other much,” Dan slowly started.
“That’s true,” Phil chuckled, “Well whadaya wanna know? I’m pretty boring to be honest, but I’ll answer anything you got on your mind,” Phil was seemingly eager to ease the tension as well.
Dan wanted to start the conversation slow and simple but he was too damn curious not to start with the question bugging him since day one.
“Is this like…a normal thing in your office?” Dan slowly asked, gesturing his naked form.
He wasn’t even shy about being naked all the time in the office anymore. He got used to it pretty quickly, and perhaps he even enjoys catching Phil checking him out throughout the day.
“I’ve had one before you, yeah,” Phil responded, not giving much else information.
Phil’s answer just piqued Dan’s curiosity even more, but he didn’t know if he should continue prodding since Phil didn’t seem willing to elaborate for some reason. So he changed the topic, instead asking Phil about his hobbies outside of work.
Dan was surprised to learn that unlike the perpetual Dom he imagined Phil to be, Phil was instead just a normal accountant by day, but an absolute nerd by night. Phil loved all the video games he loved, they shared similar music tastes, and Phil even watched some shows that Dan liked as well. They had way more in common than Dan expected, and he ignored the strange feeling of butterflies in his stomach as he excitedly discussed their favourite band.
“You’re not boring at all,” Dan said as they ended lunch.
“Glad to hear that,” Phil smiled, helping Dan clear their dishes.
Before Phil returned to his work, Dan suddenly remembered the question he had in mind earlier before sidetracking.
“Wait, so what happened to the… the one before me?”
“He uh, just lost interest and found another job,” Phil shrugged, sitting at his desk and quickly ending the conversation.
Dan wondered why Phil was so tight-lipped about his previous personal assistant. But even more, he wondered how the previous guy could leave this job. How was the money not good enough for him to stay? Or maybe the guy had more dignity than himself, Dan thought.
Dan went to lay back on his rug and spent the rest of the day wondering if it was even possible to ever lose interest in the wonder that is Phil.
thank you for your comments and kudos <3
yes I know I accidentally went on another hiatus yet again, but at least I'm back before dan in 2k19 I guess that's an achievement? lol
(See the end of the chapter for more notes.)
Phil was pleased to enter his office and see that his assistant was punctual the next day. He smiled as the boy sitting on the rug greeted him softly, still ever so shy. The smell of the coffee already made for him was so inviting.
“Why don’t you make yourself a drink too?” Phil asked as he sat on his desk.
“I may have had a coffee before you entered,” Dan admitted quietly.
Phil smiled, glad that the boy was getting comfortable enough to do his own things while alone in the office. He settled down with his coffee and spent a while reading his emails.
Dan realised that he still couldn’t quite predict how his days in the office would go. Even when Phil was training his deepthroating, he’d change it up a bit each time. He had no option but to sit and wait to see what he’d be spending his day doing.
After Phil finished his coffee, he finally addressed Dan again.
“From your video I assume your ass won’t need training like your throat, right?” Phil chuckled a little.
Dan was confused for a moment before he remembered what video Phil was talking about. He tried so hard not to cringe as his mind replayed the first day he met Phil. How Phil boldly watched the video of him taking two dicks up his ass right in front of him. How that was the first time a stranger watched a sex tape of his. And how strange it is that the stranger is now his boss.
Phil almost cooed aloud looking at how cute Dan was, his cheeks turning pink in embarrassment at the mention of his video.
“I’d still like you to be ready for me, though,” Phil said, standing up and gesturing over his desk, “C’mere.”
Dan quickly stood up and bent over the desk - properly this time. He gasped lightly when he felt cold but gentle fingertips rest on his ass. Phil’s fingers slowly traced the curve of his ass, tickling his skin. Dan wondered if he was finally going to be fucked by his boss. He couldn’t wait and he’d be lying if he said it wasn’t on his mind most days.
The light touches stopped as Phil went to the drawer that Dan has learnt stored all his play things. Dan stayed still despite growing curious as to what Phil was retrieving.
When Phil came back, he took his time exploring more of Dan’s skin. Dan shuddered slightly as Phil stroked his back, from his shoulder blades to the dimples above his ass.
Phil felt goosebumps rising on his boy’s skin everywhere he touched. Slowly, he moved lower to Dan’s ass crack. Dan eagerly stuck his ass out, making Phil smile. Phil continued lower, his fingers sliding between Dan’s cheeks until he felt his hole.
Dan gasped as he felt Phil press against his hole. Slowly, the fingers began to pry his cheeks apart. Strong warm hands holding his ass as one finger explores his hole. Dan tried his best to relax and let Phil’s finger in.
He cleaned himself every morning before going to work as per Phil’s orders. He was proud of himself for improving his shaving skills down there too, spending less time in the bathroom every week. But somehow he still felt nervous as his boss inspected him, feeling as if he might not have done a good enough job. But his boss didn’t say anything as he let go, so Dan sighed quietly in relief.
Dan couldn’t help but jerk a little in surprise when the fingers returned, cold and wet this time. Phil placed a soothing hand on his back and slowly pushed his lubed finger into Dan.
“So tight, hard to imagine that your little hole took two big cocks,” Phil chuckled as he pumped his finger in and out.
“I’m just really good at taking cock,” Dan was really good, and in that moment of boldness he wanted Phil to know what a shame it was that Phil had been denying himself of Dan’s ass this long.
“Oh really?” Phil chuckled, loving his timid boy’s sudden feisty spirit. He took the opportunity to insert two more fingers alongside his index.
Dan wanted to respond with something witty again but ended up biting his lip to stifle the unexpected moan that escaped. Phil was going slower than Dan was used to, and it felt foreign. Dan was used to quick, desperate fucks. He never had someone pay so much attention to detail; pay attention to him this way. His own cock was growing impatient, but he realised that he quite enjoyed this slow pace.
When Phil brushed against his prostate, he didn’t bother trying to keep himself quiet. Phil smirked as Dan moaned loud. He noticed just how hard his boy was, how his breathing had gotten heavier. His boy thinks he’s really good at sex? Well he’s not ready for what Phil could do to him. Phil pressed against his prostate again just to get him more worked up.
Phil took his fingers out and Dan was more than ready for Phil to get in him. He needed it more than he needed air at the moment. He felt himself leak precome. He almost left his bent position to look behind him and beg for Phil to hurry on with it. But although he had no doubt that Phil would love to see him be desperate, he thought that Phil would appreciate it more if he was obedient and stayed still. So he pressed his cheek harder against the desk and waited with bated breath.
He was so certain that Phil was going to fuck him that he was surprised to feel something cool against his stretched hole instead. He felt a buttplug push into him, much shorter than Phil but almost as thick. Phil patted the end of the plug once it was fully inside Dan.
“There we go, now you’ll be ready for whenever I want to take you,” Phil said, satisfied. He then lightly smacked Dan’s ass, indicating for Dan to stand.
Dan slowly stood up, trying to hide the disappointment from his face. He wanted to tell Phil that he was more than ready to be taken, had been ready since the start of this weird job. But of course he had to just be patient and go with Phil’s pace.
And just as he suspected, Phil completely ignored his hard and aching cock. And he was left with his ass plugged the whole day and no more attention received until Phil took it out before leaving at the end of the day.
That became their morning routine over the week. But Dan still couldn’t really predict what would happen, because Phil used a different toy every day. He wondered just how many dildos and buttplugs Phil could possibly own. He had such a variety up his ass over the week; short and wide, long and thin, grooved, you name it, Phil probably has it.
His least favourite was the long and wide one. He did love how it filled him up at first, but it was rather uncomfortable by the end of the day. Other than that, he did love being plugged everyday. The only thing that would be better was if he was being filled by Phil himself, or if Phil paid him any attention at all the rest of the day after plugging him up.
Phil always slowly got Dan worked up by his light touches all over his body and his slow fingering before pressing the plug right up against his prostate. Phil never gave him permission to come, but Dan didn’t complain. He’d just subtly shift himself so it wouldn’t press against his prostate all day. Though he always had to rush home to get himself off.
On Friday, it seemed like just another day of their new routine. The buttplug seemed like a fairly okay one, nothing Dan couldn’t handle. It wasn’t that long and it was the perfect girth to be enjoyable for Dan.
He was laying on his side on the rug when all of a sudden, a jolt of pleasure shot up his spine. Dan yelped in surprise, realising that today’s plug was also a vibrator. He looked at his boss with wide eyes, but Phil paid him no attention as usual. In fact, he looked too busy to even play and Dan started to wonder if he had imagined the one second of vibrations.
But before Dan could second guess himself, the vibrations came again. He bit his lip as the vibrations sent pleasure straight to his already hard dick. He shifted a little on the rug, whimpering when the vibrator brushed against his prostate. The vibrations didn’t stop this time, instead a steady buzz continued in his ass.
Dan dug his nails into the rug to stop from touching himself. After a few minutes and just as he got used to it, the vibrations started going off at a random pace. He couldn’t help the little whimpers that escaped his parted lips as the vibrator pulsed in his ass, sending pleasure in waves.
“What is it?” Phil finally acknowledged him after Dan let out a particularly loud whine.
Phil sounded so genuinely clueless that Dan thought that Phil could try an acting career if he was tired of his current job.
“Sir, the vibe...” Dan whined, unable to continue his sentence as he focused on not touching himself.
“I knew you’d like it,” Phil smiled, then promptly returned his attention to the computer.
Dan had expected Phil to continue ignoring him, so he just clenched his teeth and shifted on the rug more. Just as he thought Phil couldn’t get any cheekier, the vibrations became more intense.
“Sir pleaseee...” Dan panted.
“What do you want?” Phil asked, barely able to keep a straight face this time.
“Please touch me,” Dan asked desperately, almost thrusting his hips into the air.
“I’m busy, boy,” Phil said, sounding fake apologetic.
Dan almost glared at him, but he knew better. Just as he was about to beg again, there was a knock on the door.
Dan looked at Phil in shock. Phil stared back at him, waiting for Dan to decide if he wanted to stay. But he knew that Dan wouldn’t want to, he had always hid in the bathroom when people entered his office even though Phil told him he didn’t have to. Phil knew that Dan wouldn’t want to stay especially in his current state; so hard and desperate and vulnerable.
Dan got up on shaky legs and ran for the bathroom. Just as he closed the door, he heard Phil calling for the person to come in. He could feel the vibrations get slower, probably to the lowest setting. He was grateful that Phil at least wasn’t going to leave him be a desperate mess on the edge of coming in the bathroom.
“What are you doing, Phil?”
Dan could hear the voice of a man. He didn’t mean to eavesdrop, but it wasn’t like he was consciously putting an effort to when the man was so loud.
“I don’t mean that! Don’t act stupid.”
While the man was loud, Phil was so soft that Dan couldn’t hear him at all, so he couldn’t exactly understand the one-sided conversation.
“We all saw him on Monday.”
Dan held his breath. Was the man talking about him? He felt like the entire office saw him entering the office late on Monday.
“Why are you doing this again-”
Dan couldn’t hear the rest of the conversation; it seemed as if Phil had asked the man to quieten down.
Dan gulped. He tried so hard to be invisible but because he was late once, everyone knows about him now. He guessed that he would be found out sooner or later anyway and there was probably no point hiding. It’s not like Phil actively tried to keep him away either. He’d been hiding because he was too shy to face anyone more than anything else. But why was this person so bothered about his presence in the office?
Dan wondered if it had anything to do with the previous personal assistant that Phil had. He waited in the bathroom for quite a while, his mind swimming with questions.
His thoughts were soon interrupted by the vibe in his ass increasing its vibrations again. His boner had died down a little when his mind went wandering, but now he remembered his original problem: his need to come.
He took the increasing vibrations as cue that the man had left the room, so he slowly opened the bathroom door and peeked out. He slowly walked over to Phil when he saw that the coast was clear.
Phil seemed unbothered by whatever exchange happened with his coworker, but Dan still felt the need to help his boss relax somehow. He wasn’t sure if Phil wanted to do anything though, so he just knelt by his chair.
Phil looked down at him and smiled, “Glad that you didn’t use that as an opportunity to get yourself off.”
“I would never break your rules like that,” Dan replied, almost offended that Phil thought he would disobey his rules.
Dan felt the vibrations in his ass stop entirely.
“Do you need anything, Sir?” he asked softly, looking up at his boss with doe eyes.
“Looks like you need something more than I do,” Phil answered, but he felt touched that his boy wanted to serve him.
He had hoped that Dan didn’t hear anything, but by the way the boy was looking at him like he felt responsible to help him somehow, he was afraid that Dan might have heard more than what he’d like.
Dan did feel like he needed to help Phil, but he wasn’t sure exactly what Phil needed help with. From the little exchange that he could hear, it sounded as if the man was agitated and he just wanted to help Phil relax after such a conversation.
He didn’t know how to answer his boss, he felt like his own erection was unimportant at the moment. But before he could say anything, Phil continued talking.
“Just a little while more til lunch,” Phil said before turning his attention back to the computer.
Dan felt the vibrator start pulsing again, and just resigned to feeling somewhat guilty for being late that one time and letting the office see him which caused the conversation that he couldn’t help Phil with.
By lunchtime, Dan was aching with the need to come again. Phil had continued playing with the different levels of vibrations as he was doing before his colleague had entered.
Phil honestly just wanted Dan to forget whatever happened, but he had a feeling that his boy wouldn’t let it go that easily, even in his current state.
He walked over to his boy who was sweating and trembling on the rug with the need to come.
“Get on the coffee table for me, would you?”
Dan struggled not to touch himself, even just to stave off his orgasm. He was so on edge, he didn’t know how much longer he could last. But he managed to lie on his back on the table, wondering if he was finally going to get another of his boss’s amazing handjobs again.
His boss spread his legs apart and pulled him to the edge of the table enough to let his legs be bent at the knees. He admired Dan’s hard on twitching, a small pool of precum smearing his stomach. The vibrations in his ass continued relentlessly, and Dan felt like he could come if Phil so much as lay a finger on his neglected dick.
Dan widened his eyes in shock when Phil knelt down between his legs. With a glint in his eye, Phil locked gazes with Dan mischievously before going down on him.
Dan groaned out loud. His boss’s mouth felt so good around him, so wet and warm. Phil swirled his tongue around his tip and sucked hard, sending Dan into a series of moans and whimpers.
With what little coherence he had left, Dan warned Phil about getting close. He craned his neck to look at Phil bobbing on his dick. Phil didn’t stop, however, instead sucking even harder and even playing with Dan’s balls.
Dan so badly wanted the blowjob of his lifetime to last, but he couldn’t hold it in any longer. Phil wasn’t going slow at all and with the vibrator now pressed right up his prostate, he lost control.
Dan could see stars as he came, shuddering as he felt Phil swallowing around him. He gripped the edge of the table hard and moaned loud as he came. By the end of his orgasm, he felt so spent but at the same time, he’d never felt better.
Dan woke up on the couch. He blinked his eyes open and slowly sat up, looking around him. His lunch was on the coffee table. He looked over to the desk where Phil was sat doing his work.
He looked at the clock to see that 2 hours had passed since lunchtime. His boss must’ve carried him to the couch. He realised that his ass wasn’t plugged anymore either.
His heart ached a little. He had felt the need to take care of Phil after the conversation he had with his coworker and yet there he was, letting Phil take care of him instead.
“You’re finally up,” Phil said, chuckling a little.
“Thank you for letting me come today, Sir,” Dan answered shyly.
“Your lunch has probably gotten cold,” Phil said, ignoring what Dan had said and pretending as if nothing before Dan’s nap had actually happened.
Dan sort of wished he hadn’t fallen asleep after the orgasm, or he wished that Phil didn’t let him come at all, because he originally wanted to spend lunch asking Phil about what he had heard. Judging from how he hadn’t been allowed to come the entire week, he had a feeling that today was supposed to be no different until the colleague came and changed Phil’s plans. Maybe Phil thought to give him an orgasm so good it knocked him out so that Phil wouldn’t have to deal with any questions from him.
Dan sighed, they don’t even talk anytime outside of lunch so he’d just have to drop it and wait for the next opportunity to ask about it. Still, he couldn’t shake off the feeling of being bothered by what he’d heard even though he barely heard most of it. And he didn’t even understand why he was so bothered when Phil didn’t seem to care at all.
I'm rly so grateful for all of you who still stick around even when I take ten years to update, yall don't deserve having to wait so long but thank you for being so patient I appreciate it and I hope you enjoyed the update!!