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00:56

Ready for your pegging education?

Chicagomistress@chicagomistress

Pegging 101 begins! Mistress owns your ass, and now it's time to learn how to take what I can give. Let your ass get ready for whatever I desire to put in it! #pegged #strap-on #anal

It's almost Spooky Season!

Wednesday 12:00 PM

Happy Almost Fall! Mistress wants to kick off her favorite season with a personal note to all her Loyal fan perverts! My Summer was fantastic and I would love to keep it going with some great chats and interactions in the fall. Lots more #bondage #feet #latex and #leather content will be posted! What would you like to see? #femdom #mistress #voicenote #voicecontrol #voice

3.99

00:39

Just a Hello!

June 13, 2026

Letting you know I will be available to chat this coming week, plus it's my birthday month! Show you appreciation for Ms Simone

01:22

Big Life changes

September 19, 2025

Mistress has made a very big life change decision. it will affect how I engage with submissives, allowing me more freedom and much less stress to enjoy my power exchanges. Only place to see what my next step is - news blog on my site. So if you want to discover my next adventure - go there. Then let me know your thoughts here and make Mistress happy.

3.99

01:37

Gimp scene ASMR

August 04, 2025

My Gimp loves the sound of my heels in the dungeon as he is bound on my table. Here I share the sounds of my tormenting him with you. My heels clicking on the dungeon floor. My laughter as I tease him. Desire to know what my dungeon sounds like? This clip will give you a taste. #asmr #heelsclicking #dungeon

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5.99

06:06

Unlocked, Bound and Controlled

April 06, 2025

Now that youre on my bondage table, how will I use you? Unlocked,all your parts are mine - some only for my amusement and control. Listen to your next torment as I restrain you and fill your holes. #femdom #audioclip #realdomme #mistress #femdom

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3.99

03:13

Unlocked now

March 15, 2025

What now that Mistress has unlocked you! How will she begin to use you? Unlocking you, I laugh at how small and useless your soft cock and balls are. Leading you to my table, I strap you down...listen for the rest #cbt #humiliation #cocktorment #SPH #judgeyourcock #bull #chicagomistress

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3.99

02:35

Unlocked or not?

March 09, 2025

What will happen to you? Will I unlock and allow you pleasure? Or will you remain caged to my desire? Listen to Mistress as she begins your chastity session.

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5.99

02:04

High heels in dungeon

July 20, 2024

I know you love the sound of my heels walking across the floor to you. Mistress walking towards you while you're bound to my table. Wondering what items of evil she is bringing with her. How will she torment you? As she gets closer, you start to squirm! Her high heels are getting louder now ... you struggle against the restraints and rope. Mistress us almost to you. You start to moan in pleasure and worry. What will become of you? Her heels are right next to you. You feel her presence. Smell her perfume. Feel her heat. Let's see what happens next!

01:32

Testing my method for your control

July 16, 2024

As I am still getting use to online content, it seems my audio clips didn't record so I am doing this short one as a test. please let me know if it works. I really enjoy recording these as it gives me a way to control you just with my voice from afar. warmly, chicagomistress

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3.99

02:00

For the love of bondage

June 10, 2024

Bondage makes me relax, hot and intense. If you follow my career, you know it is my main kink encompassing control over you on all levels. In this clip you hear my thoughts on bondage but what I really want to know is what turns you on with it! #femdom #bondage #mistress #voice #audioclip

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3.99

01:38

Status of My feed and plans for it!

June 04, 2024

It's been awhile since I've been active. Hear why and how I will be posting more and the interaction I would love to engage with all my fans here. I am available for audio and video custom clips. Subscribe for my IRL domination content. #mistress #audio #femdom #voice