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Hello there,
my darling!

I’m so glad the stars aligned and brought you here today! Please, make yourself at home here at my little corner of the world wide web. If you were here with me in person, I’d pop open a bottle of bubbly or perhaps get us a bourbon on the rocks, depending on what whets your palette. But for now, I hope this introduction will suffice.


I am Gem DeMilo, and I cannot wait for us to create magical memories that will last us both a lifetime. 


Born, raised and having spent most of my life in The Windy City, I am charming blend of cosmopolitain sophistication and genuine Midwestern warmth. And while I officially call Charlotte, North Carolina my home now, I have an incurable case of wanderlust, you can find me touring from time to time, and am always up for a bespoke jaunt through a Drive Me to You or Fly Me to You!


I have been described by many as an old soul who is forever young at heart, and I wholeheartedly agree. I am mature enough to hold my own with poise, grace and a quiet sense of self assuredness. I possess an MFA in Creative Writing, which makes me a gifted conversationalist who never runs out of things to discuss. That paired with my razor sharp wit and love of wordplay means the conversation will always be riveting and stimulating. At the same time, I have a spontaneous and playful nature that ensures I am always learning, always growing and always up for adventure.

In my spare time, you'll find me free writing in my journal at an independent coffee shop, working on my form and posture at a ballet barre or yoga class, volunteering at the local animal shelter, listening to podcasts, playing vintage video games (Mortal Kombat II, anyone?) or embarking on an escapade to a new destination, be it near or far. Anything that stimulates my mind, body and soul is par for the course.

I like to take the lead in a gentle, approachable way that puts sensuality and mutual enjoyment above all else. In other words, you’ll never have to play guessing games as to what I enjoy. I will assertively yet tenderly guide you, so you'll feel confident in the knowledge that our time together is as sincere and real as it gets. This can sometimes translate to explorations that go beyond a classically vanilla encounter. I consider myself a natural soft dominant, meaning that things like tease and denial, edging, light bondage, sensory deprivation, role play and certain fetishes are most definitely in my wheelhouse!

Perhaps you find this exciting, yet nerve wracking. You may even be seeking this out because you'd like to gain experience or move past confidence/body image issues. I completely understand both your excitement and apprehension. Rest assured, you are in caring, capable hands. I approach every person and every encounter with curiosity and compassion, not judgement and preconceived notions. I identify as pansexual, which means I am attracted to people of all genders, races, sizes, abilities and adult ages 21 and older. I never have and never will discriminate on the basis of race, ethnicity, gender, sexual orientation, disability or body size. My pansexuality also means that I thoroughly enjoy the company of men, women and non-binary individuals alike. Ergo, I absolutely adore time with couples! I also love any opportunity to play with my esteemed colleagues for duos (or trios and more!)

Like you, I value genuine connections and authentic experiences. As such, my rates are structured to favor amounts of time that allow things to unfold organically. I relish the chance to meet for a drink, share a meal, or plan an outing together before retiring to the private sphere. Encounters such as these are meant to be savored, so why not take our time and fully explore ourselves and each other together? 

I encourage you to peruse this site to get to know me even further. I assure you, my detail oriented nature has ensured that this site will provide you with all the information necessary to book an extraordinary time together. 


Now that you know all about me, I'd love to learn all about YOU! Let me find out what makes you tick, what excites you, what you've been craving.


I'm ready when you are, my darling.

Until then...



Gem DeMilo

photo jul 15 2023, 5 17 57 pm.jpg
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