Gem DeMilo ♥️ Chicago + Beyond
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gemdemilo.bsky.social
Gem DeMilo ♥️ Chicago + Beyond
@gemdemilo.bsky.social
3K followers 630 following 540 posts
Modern Version of Botticelli’s Venus ▫️ Proud Owner of a Big Butt ▫️Dad Joke Collector 🕸️ https://allmylinks.com/gemdemilo 💘 https://marigoldgift.com/gemdemilo/gemdemilowishlist
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gemdemilo.bsky.social
Extra dirty 🍸
Gem seductively eats an olive from the garnish of her extra dirty martini
January 28, 2026 at 6:53 PM
gemdemilo.bsky.social
Staying hot in the cold 🤍🔥
Gem lays by the fireplace in a white turtleneck bodysuit
January 19, 2026 at 4:27 PM
gemdemilo.bsky.social
Welp, it’s official. My luggage is lost and the airline is not going to offer me a full reimbursement of everything I had 🤬

So if you’d like to help me recoup my losses, gift cards to Anthropologie, Abercrombie, Nordstrom or Lululemon would be immensely appreciated 🙏❤️

[email protected]
Gem lays in bed one great exposed. A gall can’t stay naked forever!
January 12, 2026 at 4:30 PM
gemdemilo.bsky.social
Me as a tree 🌳
January 8, 2026 at 11:00 PM
gemdemilo.bsky.social
How your email finds me 💌
January 7, 2026 at 5:18 PM
gemdemilo.bsky.social
New Year, New Travels ✈️

🎆January
Charlotte NC: 1/25-28
Richmond VA: 1/28-29
Washington DC: 1/29-31

❤️February
Boston MA: 2/17-19
NYC/Long Island: 2/19-20
Philadelphia PA: 2/20-22
Tampa FL: 2/22-24

💌[email protected]
January 5, 2026 at 4:56 PM
gemdemilo.bsky.social
Merry Christmas. Say it back ❤️💚
December 25, 2025 at 3:56 PM
gemdemilo.bsky.social
Officially on holiday hiatus ❤️💚

I’m going to be away from this precious dummy for 10 whole days 😭
December 23, 2025 at 9:12 PM
gemdemilo.bsky.social
Believe me, I’m just as surprised by this as you are
December 20, 2025 at 6:44 PM
gemdemilo.bsky.social
Will you keep me cozy? ❄️
December 16, 2025 at 6:37 PM
gemdemilo.bsky.social
Could’ve sworn I put that thing somewhere…
Gem sits at the edge of a tub, her ample perfect behind on full display
December 11, 2025 at 2:30 PM
gemdemilo.bsky.social
There’s just something magical about having martinis in the middle of the afternoon at an old hotel bar🍸✨
December 9, 2025 at 10:49 PM
gemdemilo.bsky.social
Duos with the beautiful @meetericaxoxo.bsky.social!

You know what to do ✨
December 3, 2025 at 11:46 PM
gemdemilo.bsky.social
If you're a sex worker, quote with your fav recent lewd and how long you've been in the industry.

7 Years 💖
December 2, 2025 at 9:07 PM
gemdemilo.bsky.social
I don’t get on my knees very often, but when I do it’s for you ❤️‍🔥
December 2, 2025 at 3:39 PM
gemdemilo.bsky.social
You’ve been visited by three spirits.

The three spirits:
November 25, 2025 at 1:21 AM
gemdemilo.bsky.social
Forget being your Pilates Princess. I wanna be your Barre Baroness 🩰💕
November 22, 2025 at 7:02 PM
gemdemilo.bsky.social
Alexa: Play “One Thing” by Lola Young 🎵💙
November 18, 2025 at 11:47 PM
gemdemilo.bsky.social
The best foreplay is a riveting conversation ❤️‍🔥
November 13, 2025 at 11:03 PM
gemdemilo.bsky.social
Talk about a great pumpkin 🎃🧡
October 27, 2025 at 9:23 PM
gemdemilo.bsky.social
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 🤩
October 15, 2025 at 10:11 PM
gemdemilo.bsky.social
RIP Diane Keaton 💔

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
gemdemilo.bsky.social
My love language is fancy olive oil 🫒💚

Thank you for this lovely gift, A!
October 6, 2025 at 8:39 PM
gemdemilo.bsky.social
Kiss me it’s my birthday 💋🥂
October 1, 2025 at 3:34 PM
gemdemilo.bsky.social
Ngl I’m way too excited for this! 😀🙌🍨

Thanks for the lovely birthday gift, B💗
September 29, 2025 at 10:46 PM