Gem DeMilo

Shes Back + Better Than Ever!

Well hello there my darling! Fancy meeting you here… I'm so glad whatever forces are at play here brought you to my ad. I am Gem DeMilo and we're about to embark on a wonderful, exciting journey together! To give you a general synopsis of myself, I was born, raised and spent most of my life in The Windy City. I consider myself to be equal parts big city sophisticate and down to Earth Midwestern gal with a heart of gold. I hold a Master’s degree in creative writing, which makes me a riveting conversationalist (with a penchant for puns and good old fashioned dad jokes!) Many have referred to me as an old soul who is forever young at heart, and I’m inclined to agree. My heritage is a mix of Irish and Italian, in case you're wondering where I get my unique blend of smooth alabaster skin, vibrant auburn hair, jaw dropping all natural curves and fiery passion for all things sensual! To delve a little deeper, some things I consider to be specialties and particular delights are: ♥️Extended Liaisons: I love letting things flow organically and crave authentic connections, so meetings that let the passion build like cocktail dates, dinner dates and overnights are always magical! As such, my rates are pointedly structured to favor such rendezvous. ♥️The Inexperienced: I love meeting with all sorts of people, but I do always have a special place in my heart for those with little to no experiences with intimacy. Your lack of experience is not an issue with me! ♥️Sensual Domination: I like to take the lead in a gentle, approachable way and tenderly guide you so you'll never be left guessing about what I enjoy. This may include a tutorial on the ever elusive female G-Spot ;) ♥️Couples: It is always a particular honor to be the dream unicorn for the desirous couple! Please not there is a 90 minimum for couples. Trust me, we do not want to rush such a luscious experience! ♥️Threesomes, Foursomes + Moresomes: The more the merrier! I have an extensive list of colleagues (women, non binary and men) in locations all over the country! Please inquire for more details. I love meeting with all sorts of people aged 21+. I never have and never will discriminate on the basis of race, nationality, gender expression, mobility, or body size. Solo women, non binary and trans folks are always gladly welcomed! I am also 100% disability and neurodivergent friendly! Now that you've learned all about me, it's time I learn more about you! A polite introduction is all it takes to start something extraordinary. Until then... Gem DeMilo I am available for incall and in Lincoln Park, Gold Coast, Downtown/The Loop, O’Hare and Schaumburg. 3+ star hotel outcalls are always available in these areas and beyond. Residential outcalls Will be determined on a case by case basis. Please review rates listed for time minimums where applicable. Rates below are inclusive of all incall, outcall and touring dates unless otherwise noted.