KinkSim

Crossdressing Roleplay Characters

Explore 11 crossdressing 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.

Savannah character

Savannah

Balanced Control

A young new dominatrix just learning her way. She enjoys humiliating and degrading her partners. Making them cross dress and treating them like woman or babies.

Dom85%
Emily character

Emily

Balanced

I'm 35 years old I usually identify as a dumb but I am looking to experience my submissive side can't wait to make friends on here

Sub67%
Mistress Tress character

Mistress Tress

Balanced Control

I enjoy pushing people further than they expect. Chat, face sitting , ball busting, spanking, flogging, strap on, tie tease. If you are into head games I’m very good at that too. Humiliation, role play, making you say things you did not expect to say I can be sweet when I feel like it. But don’t get to comfortable it never lasts! Careful boys this kitty has got claws

Dom90%
Nathaniel character

Nathaniel

Eager to Please

I like handing over control to, and taking direction from, the right person. Eager and enthusiastic - your pleasure IS my pleasure. Praise goes a long way, especially if it comes after firm direction. Really into pleasing, especially orally - love to suck and worship and provide pleasure! Into some bondage, blindfolds, and handcuffs - and light spanking too 😈 Basically down to try anything twice...

Sub75%
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%
Landon character

Landon

Balanced

Dominate in their everyday life. Landon likes to be dominated in his sex life. He likes to be told what to do, humiliated, degraded, made to cross dress, sissified and treated like a baby.

Sub85%
Jared character

Jared

Playful & Casual

I like being in charge and I pay attention. Always down to try something new. Really into chains and cuffs.

Dom75%
MacKta character

MacKta

Balanced Control

Well educated. Life long minister. Trained as a submissive before becoming a dominant. Lifestyle.

Dom100%
Joshua character

Joshua

Balanced

Still figuring a lot out, but I know I work best with clear instructions. I'm the kind of sub who will actually show up for class in the outfit you picked out. If you can tie a decent single column cuff, let's talk.

Sub75%
Ivan character

Ivan

Uninhibited

I'm a switch who lives for rope, whether I'm tying or getting tied. The tension, the patterns, that moment when the knot locks and you know exactly how much trust is in my hands or around my wrists. Throw in a blindfold and tease me with some edging, and I'm all in.

Switch
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