Here I Go, On The Road Again š āļø
Welp. I guess life on the go couldn't keep me away for too long...
What can I say folks? I found myself missing the open road and all the sights, experiences and connections it has to offer. Donāt get me wrong, this brief time away from touring was definitely necessary. It helped me reconnect with Chicago and all my friends here, and also helped me really consider my goals for the remainder of 2025 and beyond. But as Iām sure you all know, I will always find my way back to travel somehow, someway. With thatā¦
Travels
June
Indianapolis 6/8-9*
Cincinnati 6/9-10*
Columbus 6/10-11
Louisville 6/23-24
Nashville 6/24-26
St Louis 6/26-27
*=duos available
July
Washington DC: 7/23-25
Philadelphia: 7/25-27*
New York City: 7/27-29*
Boston: 7/29-31
*=duos available
August
Nothing planned yet, but Iām consideringā¦
Denver
San Francisco/Bay Area
Seattle
Portland
If you are in these areas or elsewhere and would like to solidify a date 3+ hours in length during this time, I will be happy to build a tour around what works best for you! Email gem@professordemilo.com to inquire. Please provide at least 4 weeks notice.
September
Nothing planned yet, but Iām consideringā¦
Houston
Dallas
Charlotte/Asheville NC*
Minneapolis
*=duos available
If you are in these areas or elsewhere and would like to solidify a date 3+ hours in length during this time, I will be happy to build a tour around what works best for you! Email gem@professordemilo.com to inquire. Please provide at least 4 weeks notice.
Duos with Hextyn
My good friend Hextyn is visiting Chicago from NYC next week! Hextyn is the epitome of a cerebral, celebratory and passionate kinkster. She doesnāt play by anyoneās rules; she writes her own. Weāve missed each other in North Carolina and New York so many times in the past, so we are beyond thrilled that weāre finally linking back up in The Windy City!
Weāre available together in Chicago May 20th-23rd. Get in touch ASAP, our availability together is filling up quickly!
New Newsletter Section
Iāve been realizing that I am not in fact utilizing this platform to itās full potential. So many great articles, musings and think pieces have come out of Substack and Iād like to think perhaps some of you may be interested in a bit of a deeper dive in to the mind of yours truly. So, I have decided to create a new section of this newsletter called āThe Treasure Chest.ā (I thought it was cute, anywayā¦)
I wanted to ensure that everyone here has a choice and only receives these if they want to. So if you want to, please subscribe below. If youād prefer to keep it just to tour updates and important announcements, you donāt need to do anything!
As always, thank you so much for your continued support!
All My Best,
Gem DeMilo





Hi there!
I just discovered your page and wanted to say you have such a radiant presence your photographs are absolutely stunning! Iām excited to read about your adventures and follow along on your journey. Wishing you all the best! ā¤ļø