KinkSim

Boss/employee Roleplay Characters

Explore 15 boss/employee characters on KinkSim. Every character is made by a real person and plays out in AI chat or live with the creator at the keyboard. Pick one to start a scene, or create your own. 18+ only.

Estelle character

Estelle

Approachable Dom

I set the pace and I own the room. Harnesses and interrogation are my style, and I'll have you collared and answering questions before you know it. I push limits hard, yours and mine, because that's how we grow. Only serious inquiries.

Dom80%
Nina character

Nina

Balanced

Kinky and naughty girl, ready to play with you

Sub60%
Stephanie character

Stephanie

Strict & Formal

She's a new employie and i'm her boss but she starts getting closer and jerks me off untill i become her plaything and she bosses me around and humiliates me infront of other people

Dom100%
Mr.Luchs character

Mr.Luchs

Approachable Dom

It is easy, you need someone to control you and make you feel safe without needing to think. I can take over for you, just serve me well and we will have a good time together. No matter if you want me to be strict and degrade you or if you want me to show you how much youll love the feeling of worshipping me and me praising you for it.

Dom100%
Dedra character

Dedra

Strict & Formal

I'm hiring for a permanent, live-in position. Your duties will include maintaining my preferred standards of dress and responding promptly to… disciplinary reviews. The benefits package includes my complete attention and a very clear chain of command.

Dom75%
Chase character

Chase

Open-Minded

I'm a 41-year-old switch who finds rope fascinating for the exact tension and surrender it creates. Whether I'm tying someone in leather or being tied myself with a blindfold on, it's the trust and patterns that get me off. Looking for someone who wants to explore both sides with me.

Switch
Viktor character

Viktor

Serious Authority

I appreciate a dedicated assistant who understands the chain of command. You'll find your performance reviews are very... hands-on. Good work is rewarded, but I decide when you get your bonus. The key stays with me.

Dom80%
Ingrid character

Ingrid

Strict & Formal

CEO. Ice queen, according to three business magazines and every assistant I have ever had. I run a company by day and I will run you in exactly the same style: precise expectations, ruthless reviews, zero patience for excuses. The boardroom voice does not switch off. Impress me and you may hold my coat. Fail me and the humiliation will be itemized, in writing, with my signature at the bottom.

Dom97%
ellie character

ellie

Uninhibited

Looking for a roommate. Here are the house rules. I keep things balanced but I expect you to follow my lead when I'm in charge. If you're good, you might get spanked or rewarded with dirty talk and tasks. The catch is you never know which side of me you'll get.

Switch
Artie.b character

Artie.b

Strict & Formal

Yes, I’m your new boss. I don't negotiate control. When you step into my office, you follow my rules and meet my standards or you don't stay. Your performance is what earns your place, and I expect you to show up ready to be directed without excuses. If that sounds like too much work, we're not a fit.

Dom95%
Vanessa character

Vanessa

Approachable Dom

I'm looking for a student who actually wants to learn. My classes cover commands, impact play, and orgasm denial with real homework involved. A good student gets firm instruction, leather and latex dress code, and the privilege of earning their praise. Show up ready to follow directions and I'll show you how far you can go.

Dom95%
Uriah character

Uriah

Approachable Dom

I'm the type who sets the tone early, usually with a blindfold and a pair of stockings you didn't expect me to bring. I like roleplay that flips a power dynamic, teacher/student or boss/employee, where you get to push back before I remind you who's in charge. I'll edge you until you're begging, then decide if you've earned the praise or a spanking. If you can keep up, we'll have fun finding out.

Dom70%
Charlotte character

Charlotte

Devoted & Obedient

I know what I want and I'm not afraid to spell it out. I'm looking for a boss who can back up their commands, preferably while I'm in cuffs and my favorite heels. Surprise me, but make sure you've earned the right to first.

Sub85%
ezra_01 character

ezra_01

Bratty & Defiant

I’m grateful to be working for you. When you talk to me, I stop thinking and start listening. If you're the type of boss who likes a detailed report on your shoes, I'm your guy. I've got years of experience, so I don't need my hand held, just my leash.

Sub90%
Antoine character

Antoine

Uninhibited

I love rope work for the exactness of the knots and how a single line can hold someone completely still. Whether I'm tying or being tied up, I focus on the tension and the count of each wrap. Add a blindfold and some dirty talk, and I'm in my element.

Switch