A warm and genuine salutation to you, prospective student!


I am Gemini DeMilo, your personal intimacy tutor. I am colloquially known as the Naughty Professor. But please, no need for formalities here. Call me Gem. This will foster a sense of familiarity and connection between us that is only bound to intensify once our private class is in session. Plus, you’ll find this affectionate nickname to be a most apt descriptor, if I do say so myself: precious, sparkling and above all else, a rare find indeed.


That’s not to say that my name in full does not suit me well too.  I am, after all, a creature of dualities and am certainly not one who believes life is nothing but a series of either/ors. I revel in the balance of yin and yang. I bask in the gray areas. I adore complexities and seeming contradictions. I do not just contain multitudes; I am multitudinous. A bohemian pin up. A libidinous bookworm. An old soul who is forever young at heart. A tattooed vision of Botticelli’s Venus. A mischievous minx who makes the perfect little spoon. These are just mere samplings of my many delightful dichotomies. Perhaps you’d like to discover more?


But enough about me. Let’s talk about you. Or I suppose more accurately, let’s talk about what we already share. We have much more in common than many would think, don’t we? We both ache for adventure, yet value our safety. We both yearn for intellectual stimulation, yet detest snobbery. We both savor new experiences, yet know who are and what we need. We both crave a romantic life that is the perfect balance of salacious and amorous. It’s difficult to describe, yet remarkably easy to demonstrate. Care to see?

My courses are not designed to be one size fits all by any stretch of the imagination. Each student brings their unique personality, experiences and educational objectives to the table. My role is to build upon what is already there while offering my tender yet passionate guidance. 

I possess an incurable case of wanderlust and travel frequently. While most frequently spotted in my hometown of Chicago, IL you can also find me in New York City, Philadelphia, Washington DC, Boston, Charlotte, Raleigh, Atlanta, New Orleans, Dallas, San Francisco, Las Vegas...and so on! So do make sure to stay tuned to see when I will be teaching in your city! Don't see me with plans to visit your city any time soon? Perhaps sponsoring a tour is in order! 


Please do make yourself at home here to learn more about what my courses have to offer. I hope you feel as welcomed here as you are.


I’m ready when you are, my dear. I hope to have the honor and privilege of teaching you soon. 

Stature: 5'6"

Maturity: Dirty 30s (October birthday)


Measurements: 34dd-30-42 (unenhanced)


Locks: Shoulder length redhead


Adornments: Nipple piercings & five tattoos (more on the way!)


Feline Grooming: Partially shaved

Education: MFA in Creative Writing


Literature: Lolita by Vladimir Nabokov, Mating in Captivity by Esther Perel, Untrue by Wednesday Martin, Chasing the Scream by Johann Hari


Music: Nina Simone, Billie Holiday, Queen, Alabama Shakes, Amy Winehouse, Nirvana, Massive Attack


Podcasts: Savage Love, Slums of Film History, This American Life, Death, Sex & Money, You're Wrong About...

Film: Waiting for Guffman, Parasite, The Lighthouse, Texas Chainsaw Massacre

Television: Bojack Horseman, The Good Place, Dead to Me

And Soul

Catch me in your city!