February 3, 2024 at 10:44 am

Cheating Boss Tells Woman To Act Like His Workplace Affair Never Happened, But It Ends Up Costing Him His Career

by Ryan McCarthy

Source: Reddit/AITA/Pexels

Unfortunately, workplace affairs are probably more common than we know. Secretaries and bosses, secret IMs between coworkers, its all quite scandalous!

But even still, having that affair while literally still in your workplace is pretty insane, no?

Apparently not insane enough for the cheating couple in this story to get caught not once, but twice, with the second time costing both of them their jobs!

Check it out!

Hoisted By His Own Petard

The cast: (names have been changed to protect identities.)

Kerry: my friend, and the heroine of the story.

Sharon: the secretary with loose morals.

Roger: IT manager, and villain of the story.

Ivan: the “CEO” and company owner, also owner of three or so other small companies, one of which was in the same office block.

Olivia: Roger’s wife.

Keep that in mind, because this story gets pretty complicated. Now that names are out of the way, we can get on to the good part!

Kerry works for a small IT company as a programmer and Web designer along with about 8 others, including her manager and her newest colleague, Sharon the secretary.

Roger is a womanizing rogue who makes frequent moderately offensive comments about women – customers and staff – like he has no brain-mouth filter.

Sharon is, as Kerry puts it, ‘an upwardly mobile skank’ who will literally (yes, actually) blow the boss if he buys her new shoes, so… One way to get a bonus.

Sounds like a lovely gal! And Kerry’s suspicions were soon confirmed during a late day at the office.

The first Kerry knew about Sharon’s behavior was late one Saturday afternoon, when everyone had left for the weekend, except Kerry as she had a project.

She was beavering away at her desk in a nearly silent office when she heard a squeal.

She immediately got up to investigate, and found her boss’ door ajar. She heard another squeal, and walked in….

Only to find Sharon bent over the desk with her skirt hitched up above her hips, her boss, trousers round his ankles positioned behind her. (Yes, this is artistic licence, but that’s how she described it)

Talk about getting caught with your pants down! Literally! To no one’s surprise, Roger was a little flustered after being caught sleeping around!

Roger’s expression indicated fury and embarrassment.

Sharon had an expression like the cat that had the cream, with no pun intended. She certainly didn’t seem bothered about being caught.

Roger recovers his composure, puts his trousers back on and called Kerry back into the room – she hadn’t stopped to watch – and threatened to fire her if she let slip what she’d seen.

The instruction was “Tell nobody. Act like it never happened.”

This was at the height of Covid, and they were looking at the possibility of reducing staff, something which fortunately never happened, but at the time of this story, nobody was sure.

Ewwwwwww. I would never attend another meeting in that room again. I don’t know where exactly Roger and Sharon have been in there!

Kerry kept quiet.

Roger would occasionally remember that she knew what he was up to, and would give her dirty looks, but little more was said.

Sharon and Roger were still having regular *** at work, and Sharon was getting the bonuses that the team should have received.

But soon a day came where Roger’s warning to Kerry would come back to bite him.

One Saturday, about 6 months after the initial ‘shock discovery’, an opportunity for revenge (and technically malicious compliance) presented itself.

Olivia, Roger’s wife, popped in. The staff were still there, and the office was busy and a bit noisy.

Roger had excused himself to his office with Sharon early as he knew his wife would be in later to meet him and wanted to get his end away before she arrived. She was early.

Olivia was standing at Sharon’s desk – Sharon was the secretary, after all – and Kerry saw an opportunity.

She offered to help, in the absence of the secretary, and Olivia asked to see Roger.

With Sharon gone, thank God Kerry was there to show Roger’s wife to his office! Such a kind coworker to fill in for her like that!

Kerry obliged. The next bit is a little vague, as Kerry skipped some details.

But, apparently, she knows how to get past the lock on his office door, like the door frame is a little too big, and that’s the vague bit.

Kerry was able to open the door as if it wasn’t locked, and hold it open for Olivia, who walked in to see her husband screwing the secretary from behind.

I’m sure the two of them were experiencing some Deja Vu from the last time they had been caught. But this interruption was a lot less peaceful…

Olivia’s eruption was one of incandescent fury, which caused Roger’s excuses to melt away.

He was trying to explain that it wasn’t what it looked like while pulling his trousers up.

Sharon, meanwhile, had tried to discreetly leave, but Olivia had turned her full wrath on Sharon’s direction, so Sharon excused herself by asking Roger why he’d never told her he was married (he had actually told her, but the ruse worked).

With Olivia’s fury focused back on Rob, Rob’s anger quickly found its target in Kerry!

Roger stared daggers at Kerry, but she told him that she’d done as he asked. She had never told anyone, and had acted as if it had never happened. Just as he’d demanded.

Olivia asked what she meant, and she explained in painful detail what had been going on.

But another unexpected guest was coming, one that would turn Roger’s situation from bad to worse!

With Olivia screaming at Roger, nobody heard the big boss, Ivan, arrive. He must have heard the ruckus and come to investigate.

At this point, he’d heard enough from outside the office, and Kerry was asked to leave.

Roger doesn’t work there anymore, and neither does Sharon.

Sharon was dismissed for gross misconduct, and Roger is awaiting a court date – something about fraud or embezzlement or something. Details are sketchy here. No information about his marriage. Sorry.

Kerry is still at the company, but now works as an assistant manager to a newly appointed female manager.

Gotta say, pretty tough day for Roger, but it’s not like he didn’t deserve ever second of it!

Reddit absolutely loved this story of much deserved karma, with many commenting on how stupid Roger had to be.

Source: Reddit/AITA

Some Redditors commented that Sharon’s professional reputation was probably ruined.

Source: Reddit/AITA

And others wondered why Roger would threaten the only person who could ruin his career.

Source: Reddit/AITA

And finally, this user said that while he expected Kerry to just go directly to Ivan, this was MUCH more satisfying!

Source: Reddit/AITA

Obviously folks, don’t cheat on your significant other.

But for all you scumbags out there, don’t cheat on your significant other when you know they are coming in to visit you that same day!

Come on people!

Want to read another story where somebody got satisfying revenge? Check out this post about a woman who tracked down a contractor who tried to vanish without a trace.