Gem DeMilo ♥️ Chicago + Beyond
@gemdemilo.bsky.social
Modern Version of Botticelli’s Venus ▫️ Proud Owner of a Big Butt ▫️Dad Joke Collector 🕸️ https://allmylinks.com/gemdemilo 💘 https://marigoldgift.com/gemdemilo/gemdemilowishlist
Pinned
Would you kiss my ass if I asked nicely? 🌝✨
Forget being your Pilates Princess. I wanna be your Barre Baroness 🩰💕
November 22, 2025 at 7:02 PM
Forget being your Pilates Princess. I wanna be your Barre Baroness 🩰💕
Alexa: Play “One Thing” by Lola Young 🎵💙
November 18, 2025 at 11:47 PM
Alexa: Play “One Thing” by Lola Young 🎵💙
The best foreplay is a riveting conversation ❤️🔥
November 13, 2025 at 11:03 PM
The best foreplay is a riveting conversation ❤️🔥
Reposted by Gem DeMilo ♥️ Chicago + Beyond
Would you kiss my ass if I asked nicely? 🌝✨
September 24, 2025 at 3:41 PM
Would you kiss my ass if I asked nicely? 🌝✨
Which costume should I wear for Halloween tomorrow? 🎃👻
1) The Antler Queen from Yellowjackets
-OR-
2) Alex from A Clockwork Orange
Help me decide!
1) The Antler Queen from Yellowjackets
-OR-
2) Alex from A Clockwork Orange
Help me decide!
October 30, 2025 at 9:47 PM
Which costume should I wear for Halloween tomorrow? 🎃👻
1) The Antler Queen from Yellowjackets
-OR-
2) Alex from A Clockwork Orange
Help me decide!
1) The Antler Queen from Yellowjackets
-OR-
2) Alex from A Clockwork Orange
Help me decide!
Talk about a great pumpkin 🎃🧡
October 27, 2025 at 9:23 PM
Talk about a great pumpkin 🎃🧡
Got my hair done and all the women in my life have noticed the difference. Meanwhile no men have.
In other words, it’s perfect 🤩
In other words, it’s perfect 🤩
October 15, 2025 at 10:11 PM
Got my hair done and all the women in my life have noticed the difference. Meanwhile no men have.
In other words, it’s perfect 🤩
In other words, it’s perfect 🤩
RIP Diane Keaton 💔
Thanks for inspiring all of us quirky sexy women and inspiring us to live life fully and whimsically 🕊️
Thanks for inspiring all of us quirky sexy women and inspiring us to live life fully and whimsically 🕊️
October 11, 2025 at 7:37 PM
RIP Diane Keaton 💔
Thanks for inspiring all of us quirky sexy women and inspiring us to live life fully and whimsically 🕊️
Thanks for inspiring all of us quirky sexy women and inspiring us to live life fully and whimsically 🕊️
My love language is fancy olive oil 🫒💚
Thank you for this lovely gift, A!
Thank you for this lovely gift, A!
October 6, 2025 at 8:39 PM
My love language is fancy olive oil 🫒💚
Thank you for this lovely gift, A!
Thank you for this lovely gift, A!
Kiss me it’s my birthday 💋🥂
October 1, 2025 at 3:34 PM
Kiss me it’s my birthday 💋🥂
Ngl I’m way too excited for this! 😀🙌🍨
Thanks for the lovely birthday gift, B💗
Thanks for the lovely birthday gift, B💗
September 29, 2025 at 10:46 PM
Ngl I’m way too excited for this! 😀🙌🍨
Thanks for the lovely birthday gift, B💗
Thanks for the lovely birthday gift, B💗
🍁Fall Travels🍁
September 26, 2025 at 4:06 PM
🍁Fall Travels🍁
Would you kiss my ass if I asked nicely? 🌝✨
September 24, 2025 at 3:41 PM
Would you kiss my ass if I asked nicely? 🌝✨
You wanted to see me, Mr. Draper? 🍸
September 17, 2025 at 9:49 PM
You wanted to see me, Mr. Draper? 🍸
I wanna take a ride on your disco stick 🪩🩶
September 5, 2025 at 6:14 PM
I wanna take a ride on your disco stick 🪩🩶
Pick a number and I’ll answer!
September 3, 2025 at 6:01 PM
Pick a number and I’ll answer!
Physically I’m back in Chicago 🏙️
Mentally I’m still here 🏝️
Mentally I’m still here 🏝️
September 2, 2025 at 2:48 PM
Physically I’m back in Chicago 🏙️
Mentally I’m still here 🏝️
Mentally I’m still here 🏝️
Catch me while you can ✈️🩵
August 21, 2025 at 6:06 PM
Catch me while you can ✈️🩵
Hot take: if you contact a companion to book an extended date or FMTY and then bail in the midst of making plans for whatever reason, you should buy a little something off their wishlist to show you value their time.
August 20, 2025 at 1:11 AM
Hot take: if you contact a companion to book an extended date or FMTY and then bail in the midst of making plans for whatever reason, you should buy a little something off their wishlist to show you value their time.
Live life colorfully 🌈✨
August 18, 2025 at 10:46 PM
Live life colorfully 🌈✨
From visiting the Space Needle, to seeing the new Nirvana exhibit at MOPOP, to an amazing dinner overlooking Puget Sound & Mt Rainer, to a selection of extraordinary & unique gifts..I couldn’t have asked for a better day in Seattle!
Thank you for such a wonderful time B 💗
Thank you for such a wonderful time B 💗
August 15, 2025 at 4:16 PM
From visiting the Space Needle, to seeing the new Nirvana exhibit at MOPOP, to an amazing dinner overlooking Puget Sound & Mt Rainer, to a selection of extraordinary & unique gifts..I couldn’t have asked for a better day in Seattle!
Thank you for such a wonderful time B 💗
Thank you for such a wonderful time B 💗
Coffee, tea or me? 🩵
August 5, 2025 at 3:19 PM
Coffee, tea or me? 🩵
I just found out that vaginas have the same pH as a glass of red wine. Could pussy be any more sophisticated? ♥️🍷
August 4, 2025 at 9:25 PM
I just found out that vaginas have the same pH as a glass of red wine. Could pussy be any more sophisticated? ♥️🍷
The devil is in the details 😈
August 2, 2025 at 8:32 PM
The devil is in the details 😈