The Caning of the Boss

The Caning of the Boss

Kelly the Sub 2025

A quick story! Please leave a comment! Thanks!

Okay so this is weird. Really weird. But I need to tell someone and I can’t tell anyone who actually knows me, so here we are. I’ve changed names obviously, locations too, but I swear to god this actually happened.

Couple years back. I was working at this law firm downtown, fancy place, all glass and marble and people in expensive suits pretending they weren’t miserable. I was a secretary. Just a secretary, nothing special.

Maybe I should, yeah, okay. I’m K. Mid-twenties then, I guess twenty-seven now? Doesn’t really matter. I’m pretty average looking, like aggressively average. Not ugly but also not the kind of person anyone looks at twice. I can walk through a crowded bar and it’s like I’m invisible, which honestly I prefer most of the time. Some people have called me boring to my face, which, rude, but also... I mean they’re not wrong. I keep to myself. I have thoughts though. Weird thoughts sometimes. Thoughts I definitely don’t share with anyone.

But whatever, this isn’t about me.

It’s about my boss. Miss Harper.

Evelyn Harper. Early forties I think, maybe younger, she was one of those women who could be thirty-five or forty-eight, impossible to tell. An associate at the firm. Everyone respected her. No wait, that’s not right. Everyone was terrified of her. That’s more accurate.

She had this reputation for being... demanding doesn’t even cover it. Demanding and harsh and she expected your work to be perfect, like absolutely flawless, and if it wasn’t? Jesus. I saw her make a paralegal cry once in a conference room. Just destroyed him over some filing mistake.

A lot of people hated her guts. Mr Khan called her a bitter bitch once in a meeting, I was taking notes and my pen literally froze on the page. But people nodded. Like half the room agreed with him. That’s how bad it was.

Of course she wasn’t IN the meeting. Nobody would’ve dared say that to her face.

But here’s the thing: I kind of liked her? Not like, liked-liked her, but I appreciated that she was professional. She mostly ignored me, which was fine, and when she did notice me she treated me with respect as long as I did good work. If I fucked up though, yeah, she could be mean. Really mean.

I remember coming home one time and just sobbing on my kitchen floor because she’d torn into me about some mistake I made. It was tiny but it was also actually significant, like it could’ve caused real problems, so maybe she was right to be pissed. Still wasn’t very nice about it though.

Anyway. Through some combination of luck and definitely bad luck I ended up working more closely with her. Eventually I was basically her personal assistant. Didn’t love that at first but it came with more money, which I desperately needed, so I sucked it up.

This all happened on a Friday.

Late afternoon, almost evening. Most people had already left, you could feel that Friday energy where everyone’s just gone, the office gets quiet and echoey. I was packing up when my phone rang.

“K, I need you to do something for me.” Her voice, clipped and professional like always. “I left the Anselmo files at home. On my desk in my office. I need them tonight, there’s a deadline.”

“Oh, um, sure, of course Miss Harper. I can be there in like fifteen, twenty minutes?”

“Good. Thank you.”

Click. She hung up.

I sat there for a second feeling weirdly smug? Like, she was always so perfect and put-together and she’d forgotten something important. The Anselmo case was huge, like partnership-level huge. For once she’d screwed up instead of me.

I grabbed my stuff and headed out.

I’d never been to her place but I knew where it was, one of those old houses on the outskirts, the fancy part of town where the streets have trees and the houses have names instead of just numbers. When I pulled up I just sat in my car for a minute staring at it.

It was massive. Like, mansion massive. Surrounded by this tall iron fence that looked old and expensive. The house itself was all stone and tall windows, the kind of place that probably had a name like “Willowbrook Estate” or something pretentious.

I rang the doorbell. One of those old fashioned ones that actually rings, not a buzzer.

A woman answered. Not Miss Harper, someone I’d never seen before.

I figured she was like, the maid? Or housekeeper? But she didn’t really look like, I don’t know what I expected a maid to look like, but not this. She was wearing black pants and this grey blouse that was fitted, like really fitted in a way that showed off her figure. Dark hair pulled back. Really red lipstick, the kind that’s almost too red, too perfect.

“You must be K,” she said. Eastern European accent, maybe? “I’m Zora. Please, come in.”

“Oh, I just need to, I brought the files for Miss Harper, so I can just, ”

“She’s expecting you. Come in.”

It wasn’t really a question.

So I followed her inside and the house was even more impressive on the inside. High ceilings, dark wood everywhere, expensive-looking art on the walls, the kind of place that’s almost too nice to actually live in, you know? Like a museum that someone accidentally furnished as a home.

We walked through a hallway and into what I guess was the living room. Big space, fireplace, floor-to-ceiling bookshelves, leather furniture that probably cost more than my car.

And there she was.

Miss Harper was standing near the bookshelf with her arms above her head. They were tied, actually tied with rope, to something on the ceiling. She was wearing some kind of robe or cape thing wrapped around her body.

I stopped walking. My brain just... stopped processing.

“Evelyn, your secretary is here,” Zora announced.

Miss Harper turned her head and when she saw me her face went white. Then red. Then white again.

“Not her,” she said, and her voice cracked. “Please, Zora, not her. Please.”

“We discussed this Evelyn. You ignored my warning and now there are consequences.”

“Don’t let her see me like this!” Miss Harper was pleading now, actually begging. I’d never heard her voice sound like that, high and desperate and small.

I should have left. Obviously I should have left right then.

“Miss Harper, are you, what’s happening? Are you okay?” My voice came out weird and squeaky.

Zora turned to me with this incredibly calm smile. Like we were discussing the weather. “She’s perfectly fine. This is voluntary, completely consensual. It’s her choice to submit. She wants this. Don’t you, Evelyn?”

I looked at Miss Harper, trying to understand what the hell I was seeing. Trying to find some sign that this was wrong, that I should call someone.

“Is that true?” I whispered.

Miss Harper’s face was so red. She wouldn’t look at me. After what felt like forever she gave the tiniest nod. Barely even a movement.

“You see,” Zora said, walking in this slow circle around her, “Evelyn needs structure. She needs discipline. Corporal punishment keeps her grounded.” She gestured toward a big leather armchair near the fireplace. “Please sit. Make yourself comfortable.”

This was insane. I should leave, I should definitely leave right now, this is my boss, this is inappropriate on like seventeen different levels,

But I didn’t leave.

I walked to the chair and sat down. The leather was cold.

Zora moved toward Miss Harper again, deliberate and slow. “Are you ready?”

“Please.” Miss Harper’s voice broke. “Please Zora, not in front of her. Anyone but her.”

“The time for negotiation is over. We discussed consequences. You agreed.”

Zora’s hands went to the robe wrapped around Miss Harper’s body.

“Zora no, ”

The robe fell.

I couldn’t breathe.

My boss, intimidating, professional, always-in-control Evelyn Harper, was completely naked. Every inch of her exposed under the soft lighting. My face felt like it was on fire.

A small sound came out of Miss Harper’s throat. Was that pleasure? Shame? I couldn’t tell.

“She has a safeword,” Zora said, looking directly at me now. “If this becomes too much she can say ‘red’ and everything stops immediately. This is consensual. She craves this. Don’t you Evelyn?”

Another tiny nod.

I felt something shift inside me. Shock and fascination and this dark curiosity I didn’t know I had. Seeing her like this, vulnerable and exposed and powerless, was intoxicating in a way I couldn’t explain. She had all the power at work. Now she had none. And I was watching it happen.

“Tell your secretary why you need this,” Zora said.

“Please...”

“Tell her.”

Long silence. Finally, so quiet I almost couldn’t hear: “Because I need to surrender. Because I can’t always be in control.”

Something in my chest tightened. I understood that feeling. The weight of always being perfect, always being strong. But I never imagined she felt it too.

I settled deeper into the chair, gripping the armrests.

Whatever was about to happen, I wanted to see it.

I wanted to watch her break.