Elliot tabbed back to his inbox on his work computer with a sigh. He'd been at this job for over a month. It paid really well, but so far he had just been doing a random assortment of menial tasks with no real pattern to them. He had just finished comparing a spreadsheet to the source data to "check for errors". It had taken almost four hours, and he'd only found 3 trivial typos that didn't even affect the correctness of the results. It felt like he was being tested, rather than doing actual work.
As Elliot looked over the new emails he'd gotten since this morning he saw that there were 3 new tasks, and none of them looked more substantial. Though the copyediting one would at least probably be less mind-numbing than the spreadsheet review had been. The job application had been vague about what exactly he'd be doing which was pretty par for the course these days, but he hadn't expected every task to be seemingly random and have no apparent stakes. Why even hire someone if you don't have actual work for them to do, he wondered. He sighed and opened the oldest email with a task for him and started skimming it. Before he could get to the actual request Kenny walked up and put a hand on his shoulder.
"Hey Elliot, sorry to interrupt but the boss wants to see you" he said, apologetically but with a bit of a grin in it that made Elliot a little nervous. Not that he wasn't already nervous at the prospect of their boss wanting to see him. Kenny had been acting as Elliot's mentor since he started. His actual manager had shook his hand on his first day, but was apparently busy enough that he couldn't spare any time after that. The fact that the boss wanted to see Elliot now felt like a bad omen.
"Oh okay I was between tasks anyway. Where's the manager's office?" Elliot asked.
"I'll show you the way" Kenny replied, with that same grin.
He seemed excited to be taking Elliot to the manager, which was a little weird. Then again Kenny just generally seemed excited to be at work so maybe it didn't have anything to do with Elliot at all. Though that was almost more off-putting, especially if Kenny's work was at all like what Elliot had been doing this month.
Kenny led him through the cubicles to a door on the far side of the office from the elevator. There were doors all along the hallways, but Kenny had stopped at one that was nicer than the others. It looked like it was made of actual solid wood, instead of the cheap hollow kind that was ubiquitous. Kenny knocked on the door, and the sound it made confirmed to Elliot that it was at the very least nicer than every office door he had ever had cause to knock on before. Elliot didn't hear a response through the door, but there was the sound of a lock disengaging and Kenny opened the door and led them inside.
"I brought Elliot, as ordered Boss" Kenny said as they stepped in to the room.
"Thank you Kenny, please wait by the door. Elliot, thank you for coming. Please sit down" said a voice from the other side of Kenny.
As Kenny stepped to the side, Elliot got his first good look at the office and at his boss. The room was completely unlike the rest of the office, decorated with dark hardwood everywhere, and plush soft carpet. The boss was at an equally nice desk, and was standing up to greet them. The office didn't really have a dress code. Elliot had generally felt somewhat overdressed just wearing a button up shirt and jeans since everyone else seemed to be dressed in tshirts and the occasional polo. Seeing the boss, though, made Elliot immediately feel infinitely underdressed. He was wearing a complete suit which looked like completely perfect, like he had put on a brand new suit moments before they walked in. The outfit fit perfectly in the unbelievably nice office, which was also weirdly huge. Elliot was walking towards the chair in front of the boss' desk and it felt like it was taking forever. What did he need all this space for?
Finally Elliot got to the chair and sat down. The bizarre circumstances had made him forget to be anxious, but now that he was sitting right in front of the boss he remembered he had no idea why he was here and immediately felt himself start to sweat, despite the coolness of the room.
"Thank you for coming on such short notice, Elliot. I know we haven't really gotten the opportunity to chat since you started, which I apologize for. It's a bit busy around here right now, which of course is why we hired you in the first place. Have you been settling in?" the boss asked.
Elliot was confused by the supposed busyness, and especially that he might be doing work that was in any way an asset to the company. But this didn't seem like a great time to ask that particular question. So he just said "uh, yes settling in fine" and without thinking about it, added on "sir" after a split second. He didn't usually refer to his bosses as "sir" but the whole environment was so odd it had just kind of popped out. The boss seemed to get a kick out of that as well. Elliot's confusion also must have shown on his face because the boss said
"Yes I'm sure the work and even the job itself are somewhat confusing to you. We don't need to get into it right now, but suffice it to say that while the work you've done may feel menial and pointless, it hasn't been for nothing. Our work is somewhat unusual, as is the structure of the company itself. But we pride ourselves on attention to detail and timeliness. While you haven't been here long, your work has been exemplary so far" then the boss hesitated for a moment before continuing. "That being said, it has been noted that you've been semi-regularly using Grindr on company time"
Elliot was taken aback "How could you possibly known that" he blurted out. Not a great defense, but he knew the cameras in the office couldn't see his phone, and it wasn't like he had done it a lot, certainly not in sight of anyone else.
"I'm glad you aren't denying it, Elliot. That will make this much easier. It's simple really. In order to connect to the office's WiFi network, you had to install an app. This app gives us full access to your phone. Both the terms of service for the app, and your employment contract give us full legal rights to do this, and to use the data we gather in whatever way we see fit." the boss said, smiling at Elliot.
Eliot was momentarily stunned by the enormity of what the boss was saying, and when he recovered enough to speak he said "That can't possibly be true, setting that all up would be absurdly expensive not to mention the legal complexity"
The boss laughed a little "I suppose I can't really blame you for not believing me, it does sound ridiculous for a job like this. Come here" the boss gestured towards his side of the desk, inviting Elliot to come look at the boss' computer.
Elliot stood up without really thinking about it, and in the process discovered that his dick had started to get hard. He straightened his pants to try and cover it, and tried not to blush. As he walked around the desk he couldn't help but notice that the boss seemed to be looking right at his crotch, and he was grinning. He didn't say anything though.
Elliot got to where the boss had indicated. The boss continued, gesturing at the screen "here you can see the screenshots of your Grindr conversations in the office" he said, clicking through photos. Elliot recognized most of them, and immediately lost the battle against blushing as the screenshots very clearly included nudes Elliot had sent on Grindr. "I have to say, I thought you would probably stop after the first couple times since no one responded to you after you sent a nude, but I guess you must be a little desperate" the boss said, laughing again.
Elliot wanted to defend himself, to say it wasn't unusual for people to not reply if they weren't interested. That it probably didn't have anything to do with the nudes. But it rang hollow, and he was sure it would just embarrass himself further. And now that the boss had said it, he found himself wondering if something about his nudes had scared everybody off. It had been awhile since he'd actually successfully hooked up with anyone. Job searching had taken up a lot of his time for several months.
The boss either hadn't noticed Elliot's embarrassment, or more likely didn't care. He was clicking through more photos as he said "You can see here we've also got everything from your photos, including quite a few very degrading videos you've taken of yourself. This one here you appear to be fucking yourself with a cucumber, and quite enjoying it I have to say. Then here we have you telling the camera how much you want to be exposed and humiliated as you hit yourself in the balls. This probably wasn't quite how you imagined that happening though" the boss said, looking back at Elliot with a grin. Suddenly Elliot saw a flash of motion by the door. He had forgotten Kenny was still in the room. He was still standing by the door, with a evil smirk on his face as he stroked his cock through his jeans. Elliot's blush intensified as he realized Kenny had heard all of that, and quite possible had seen it all already. Elliot was distracted from this mortification as he realized that the boss had coaxed him down so Elliot was bent over his knees.
The boss was saying "Of course we don't have any interest in preventing you from seeking sexual satisfaction in your life, whatever form that takes. In fact we very much want you to be fulfilled. However it is not acceptable to be using hookup apps on company time. If you need relief you should be asking either myself or Kenny if I am not available. We have a whole department of horny men who need to get off. There's no sense in wasting time meeting someone else during work hours."
Elliot was getting overwhelmed by how bizarre this situation had gotten in a very short amount of time, and was utterly unprepared for the smack on his ass that the boss delivered. Elliot made a noise of surprise but of course he was wearing pants so one smack wasn't actually painful. He wasn't getting out of here with just one though, he was sure. The boss kept spanking him as he continued "I have to punish you for breaking the rules, even though you weren't fully aware of them. After all most jobs don't want you on Grindr while you work, which you of course knew". After 10 spanks they were starting to smart a bit, even through Elliot's pants. The boss was certainly not holding back. As if on cue the boss undid Elliot's belt and pants, and pulled them down revealing Elliot's skimpy briefs. The boss groped Elliot's cock through the briefs and smirked.
"Ahh you really are into this aren't you, Elliot?" the boss said as he laughed. Elliot thought that had been rhetorical but after a second the boss gave him a swift tap on the nuts and said "Speak when spoken to, boy" Which made Elliot jump a bit as he let out a little squeak that made Kenny laugh. The idea of saying any of this was turning him out loud to this stranger who was also his boss felt unbelievably humiliating to Elliot, but he also knew the boss wasn't giving him a choice. Despite himself he also did not want it to end. Finally he managed to say "yes sir"
"Yes sir, what?" the boss asked with a smirk on his face. He wasn't going to let Elliot off that easy.
"Yes I am turned on by being exposed, humiliated, and spanked for being bad, sir" Elliot said, accidentally looking up at the monitor and seeing the video of him busting his own balls still playing silently, which made his dick twitch.
"There you go boy, that wasn't so bad was it?" the boss said, as he resumed spanking Elliot now without only the padding of his very thin briefs. The spanks were immediately much more intense and Elliot was having a hard time not moaning. That seemed to encourage the boss who was going faster and harder. Finally after 15 more spanks, the boss pulled Elliot's briefs down causing Elliot's rock hard dick to spring up and fling precum on to the boss and Elliot. The boss didn't remark on this, he just wiped some of hit off of his pants and put his finger in Elliot's mouth. Then he started spanking Elliot again. Just once first, but seemingly as hard as possible. Elliot let out a yelp and his dick spasmed again, releasing quite a bit more precum. The boss didn't stop though, and after 5 more of those Elliot's cries were getting quite loud.
The boss beckoned for Kenny to come forward, which was the first time he had acknowledged Kenny's presence after telling him to stand by the door. Kenny walked up and with no further comment shoved his quite girthy cock into Elliot's mouth, presumably to muffle Elliot's sounds. If anything that only made Elliot harder. The boss resumed spanking Elliot, slightly less hard but considerably faster. Kenny wasn't trying to do anything other than keep his dick all the way in Elliot's mouth. His dick wasn't too long, so it wasn't quite making Elliot gag, but it was close enough that if either of them move towards the other it would start to make Elliot gag. Unfortunately for Elliot the spanking was doing causing him to do just that, and the girth of Kenny's dick meant there wasn't much room for maneuvering, or breathing around it. The boss' hits sped up a little and Elliot couldn't stop himself from pushing even further forward onto Kenny's cock finally causing him to gag. Kenny took this opportunity to grab the back of Elliot's head and hold him all the way down on his dick while the boss seemed to speed up the hits even more. Elliot kept gagging and wasn't sure which way he should flinch.
Finally after several seconds Kenny let go and stepped back giving Elliot a chance to breathe. The boss gave him one last spank and then stopped. Elliot thought that might be the end of it, but the boss was opening a drawer by Elliot's face, and Elliot could see he was pulling out a spanking paddle. The boss didn't waste any time, immediately delivering a smack with the paddle that made Elliot's eyes water. The boss kept it up, and Kenny stepped forward to put his dick in Elliot's mouth again, but he didn't shove it all the way in this time. As the spanking continued, the boss started stroking Elliot's dick with his other hand, and Elliot realized he was going to cum. Kenny's dick felt good in his mouth, the spanking was making his eyes water but it was unquestionably turning him on too, and he realized with a start that the monitor had a webcam on it that appeared to be on, and there was no way the boss wasn't recording this. All of this plus the stimulation to his cock that the boss was delivering was too much for Elliot, who couldn't even warn them that he was about to cum with Kenny's dick in his mouth. The boss seemed to know anyway though, because right as Elliot was about to cum he stopped jerking Elliot off and instead delivered a flurry of spanks with the paddle and Kenny thrust the rest of the way in as Elliot went over the edge even without any more direct stimulation to his cock.
Elliot's cock exploded, but the boss had maneuvered his hand to prevent him from shooting across the room. He caught a lot of the cum in his hand, and the rest fell on the floor or into Elliot's pants and underwear. The boss wiped the cum he had caught on Elliot's face as he stood Elliot back up. Then he said "Kneel down" so Elliot did, and suddenly Kenny's cock was in his face again. Instead of pushing back into his mouth though, he was just jerking off in Elliot's face. He must have been close, because he came after a couple seconds. He shot a huge load onto Elliot's face, and Elliot wasn't stupid enough to try and wipe any of it off. He just said "Thank you sir"
The boss smiled and said "Good boy! Now there are technically a couple hours left in the work day, but I think we'll send you home early today. However you aren't allowed to wipe any of that cum off until you get home."
That made Elliot's dick twitch again which got laughs out of both the boss and Kenny. Elliot finally managed to say "yes sir" and started to stand up and get his pants and underwear back on. Before he did though the boss said "Just a second boy" so Elliot froze. The boss gestured for Elliot to bend over his lap again, and Elliot reluctantly did so. Kenny handed the boss something, and then he felt the boss rubbing something over his ass. "Just some balm to make sure your cute ass is ready to go next time". It felt really good, even though there was a bit of stinging so Elliot wasn't about to complain. Finally the boss said "Okay all done, out with you". Elliot got his pants back on, stood up and said "thank you sir" before hesitantly walking out the door.
As Elliot walked back towards the elevator to the parking garage several people he hadn't interacted with much made eye contact with him. Winking, smiling, and one person even whistled. Elliot blushed, wondering how much they knew about what had just happened to him, and thinking about all the cum still on his face.
He got to the garage, and back home without incident. Though his dick kept getting hard every time he encountered anyone else on the road thinking about whether they would be able to see the cum on his face.
Elliot got home and immediately stripped. He looked at his red ass in the mirror and his dick which had already been semi-hard was immediately rock hard again. He laid down in bed and started to jerk off again, but then he thought about how the boss had been able to get at all of the videos he'd recorded before. Elliot grabbed his phone from his pants pocked, set it up on his nightstand and started recording. He showed off his red ass, and even smacked it a couple times himself which strung like crazy, he turned around and showed off how hard he was. Then he laid back down and got back to jerking off. Imagining that the boss was there watching him touch himself. He wanted to edge at least until work was officially supposed to be over, but he came almost immediately. He managed to get even more cum on his face, so he showed that off to the camera too. Then he laid back down. He didn't think he would be able to cum again, but he was still pretty hard, so he just teased his hypersensitive dick for awhile. He wondered if everyone in the office would see all of those videos. That was mortifying, especially because the boss hadn't even mentioned some of the really humiliating ones that Elliot knew were on his phone. The thought of the whole office teasing him about them just about made him cum again though. He backed off for awhile and tried to edge again. He was doing alright for 30 minutes but that mental image kept coming back to him and he came again, though not quite as much. He looked at the camera and finally hit end on the recording. He wanted to go shower but he was exhausted and ended up falling asleep almost immediately.
Elliot woke up in the middle of the night with all that cum still on his face, and his dick rock hard again. He saw he had a work message from Kenny, which was almost enough to make him cum again. He glanced at the message, which was an unbelievably generous offer to help him find another job if he wasn't comfortable keeping this one. Elliot just replied "See you tomorrow" and grabbed his dick again.
