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Gem DeMilo

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Gem DeMilo
Chicago Escort

+I Can Teach You A Thing or Two…

Home City



Escorts, Kink

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Your personal phd in passion, affection and naked ambition awaits…

Tour Dates

Chicago: Now-2/11

Washington DC: 2/12-2/15

Richmond VA: 2/15-2/17

Raleigh NC: 2/17-2/20

Hello, I’m Gemini DeMilo: your personal PhD in passion and sensuality! But please, call me Gem!

I’m Gemini DeMilo, your personal intimacy tutor. But please, call me Gem!

The best part of seeing me is that I am the best of both worlds: wise beyond my years, yet spry and spontaneous. Smart as a whip, yet grounded and down to earth. Elegant and sophisticated with just the right amount of edginess. Equal parts charmingly romantic and delightfully saucy. Whether we meet for a short and sweet hour during your lunchbreak or a sumptuous night on the town, you’re bound to revel in my enchanting, seductive company.

Let’s let the world melt away together, shall we?

In order to proceed, please send me an email. You will receive an instant auto reply with information about appointment and screening options. You’ll also gain access to more content and my text only phone number!

When in Chicago, I have incall available in Lincoln Square (default), Gold Coast and Schaumburg (by special request)

The Look

Gem DeMilo is a 5'6", curvy, 35 year old caucasian woman with medium length red hair and blue eyes.

She is available for Male, Female, Couples, Trans, Disability, Groups, and Non Binary.


Reading is my second biggest passion (the first being rather obvious, my darling!). I have been especially interested as of late in non fiction relating to evolutionary sociology and the study of relationships. Favorite current authors include Dan Savage, Esther Perel, Brene Brown and Daniel Bergner.

I also love cinema, particularly films that came out in the 70s. It was a brave new frontier then in so many ways!

I could listen to Podcasts for hours, and am always finding new favorites.

Yoga and barre will always be my second favorite forms of exercise (again, the first should go without saying).

My second favorite vice (I’m beginning to sound like a broken record!) is coffee, and I would love to receive a bag of your favorite locally roasted beans. Whole bean or course ground only for my precious French press!


Traditional Companionship (NYC + SFO add $100)

1 Hours $400

1.5 Hours $600

2 Hours $800

Extended Discourse

3 Hour Cocktail Date $1000

4 Hour Dinner Date $1300

6 Hour Outing $1600

8-10 Hour Clock-Free $2000

14-16 Hour Overnight $2800

Strictly Domination

1 Hour $300

1.5 Hours $500

2 Hours $600

While 24 hours is always preferred, same day appointments can be arranged if I have 3 hours notice.

Screening is necessary for all courses via references, employment verification, ID Verification or RSAVS Membership. P411 members may send an invitation to view their profile.

Any message containing crassness or vulgarity in any capacity will be ignored. But you’re better than that anyway, aren’t you my dear?

Contact Info