Diana Leah

well hello there...


My name is Diana


I am a Dominatrix and switch based in Chicago

I am an eccentric and eclectic Mistress originally from London, England but I call Chicago my home. I have a magnificent figure, a traffic-stopping ass, unshaven armpits and a collection of beautiful tattoos.  I am 5ft 5 with size 7 feet and dyed (usually orange or pink) hair.  

I have years of experience in the lifestyle. I am positively driven by taboo fantasies. I am a true freak to my core. I love what I do and there are few things I am not willing to try at least once. I am a naturally Dominant woman with a soft feminine touch. I have a very sensual style of Domination but that doesn't make Me any less of a sadist with a lust for punishment. I am never too serious, although I am a strict Mistress (a stickler for proper manners) I am witty, with a very dry sense of humor. I love to laugh and I create a playful environment in My sessions.

Bouncing around both ends of the spectrum- I am a very bratty submissive and I love to play with experienced Dominants. I have mainly played with Dominants from out of town. It seems as if Chicago is quite the "bottom city". I would love to be proven wrong about this. 

I have an impressive collection of leather and latex clothes, lingerie, costumes, boots, heels and other fetish wear. I love to indulge (and tease) a true fetishist so don't spare the details! Tell me exactly what that item of clothing your babysitter wore or teacher wore around you when you were younger that sends you into a trance.  

I am an artist in my day-to-day life. I consider my BDSM practice an art and I am always trying to bring my artistic sensibilities to my sessions. Just as art making is a healing practice, I believe kink and BDSM is also.   I consider safe, sane and consensual BDSM to be a healing practice. Whether it is healing through pain or submission I believe we can heal from many things through play. I also believe in healing the toxicity and imbalance of the patriarchy by surrendering to and worshipping a powerful Goddess such as Myself.  

Before every session we will establish communication surrounding boundaries, limits and code words. 

I have many wonderful, brilliant, gorgeous friends in the lifestyle. Feel free to inquire about doubles sessions. I love to get creative and try new things, don't be shy! Lets explore our weirdest fantasies together...

find me on FetLife to see more pictures: Miss_Diana_leah

escape the stresses of your every day reality


just a few of my interests...

my favorite things 

If you are not sure what exactly it is you would like to explore, let me elaborate on my personal favorites and see if anything inspires you.

Fueling play time with a taboo role-play is by far the thing that gets me going the most, whether it is an in depth story we weave before our time together or a totally improvised scenario, I immerse myself entirely in the fantasy (possibly to a fault, I am a Pisces). Whether it is a classic age play, student & teacher, boss & secretary or something totally off the wall I adore a role-play so don't be shy! Tell me your ideas!

SPLOSH. I love to get messy. Something about disregarding the consequences of making a mess and giving in to a childhood urge to grab a handful of pudding or pie and rub it all over my face is very exciting to me.

Something I enjoy highly that comes very naturally to me is humiliation. No matter what part of your masculinity it is about I will find a way to belittle it. 

  • Slut training
  • Forced Feminization
  • Sissy training 
  • Spanking
  • Corporal punishment (caning, flogging etc)
  • Cuckolding 
  • Forced Bi
  • Showers
  • CBT
  • Splosh/Messy/Food play
  • Tickling 
  • Tease and denial
  • Stocking, feet, leg worship
  • Roleplays 
  • Age-play
  • Bondage