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Posts by Gem DeMilo ♥️ Chicago + Beyond

John Forsythe lying naked in a pool of honey

22 hours ago 1 0 1 0

We had a duo 😏

22 hours ago 4 0 1 0
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Back home in Chicago causing the most delicious debauchery with @lydiasupremacy.bsky.social
@audreydavis.bsky.social
@mrosevip.bsky.social
@therayalight.bsky.social
@gemdemilo.bsky.social
@reignrose.bsky.social

Won’t you join us?

6 days ago 78 18 7 0

Très chic! 🖤

6 days ago 2 0 1 0

Exactly the look I was going for 🩷

1 week ago 2 0 0 0

Savage x Fenty! 🩷

1 week ago 1 0 0 0

SHEESH 🥵

1 week ago 1 0 1 0
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In bloom 🌸

1 week ago 106 7 8 0

Discounted to $1000 ($600 deposit + $400 day of)/3 hrs with this location available ✨️

2 weeks ago 6 4 0 0

Date idea: you let @meetjosiequ.bsky.social & I make you a fabulous dinner, then you have us for dessert 🍨 😈

2 weeks ago 17 1 0 0
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Your skin is absolutely radiant, Sophia ✨

2 weeks ago 0 0 0 0
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What’s a line from a book, poem or song that always tugs at your heartstrings? 💘

2 weeks ago 28 2 6 0

I hope these guys are both hanging out together, collars popped, eating a big basket of French fries.

2 weeks ago 5 0 1 0

Do yall remember the guy from back in the curious cat days who would ask every SWer on there what they would do if he was a speck of salt on their French fries?

I wonder how he’s doing

2 weeks ago 27 0 1 0

Some people really don’t appreciate a good one when they have them. This could have opened up a weird, beautiful floodgate of random thoughts to share together. But instead they argued and took it to Reddit 🙄

3 weeks ago 2 0 1 0
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What’s your favorite thing to eat for brunch? ❤️

3 weeks ago 36 2 2 0
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For the record, I’d love to sit on your face 💕

3 weeks ago 40 4 1 0

I cannot adequately express how much I loved Salt N Pepa in the 90s.

3 weeks ago 2 0 0 0
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Ok but I would do unspeakably naughty things to the person who took me to this. Just sayin 🫦

3 weeks ago 19 1 2 0
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Gem seductively eats an olive from the garnish of her extra dirty martini

Gem seductively eats an olive from the garnish of her extra dirty martini

Extra dirty 🍸

2 months ago 95 5 7 1

Ways to spend your tax return this year:
- Book a sex worker
- Gift a sex worker things from their wish lists
- Tip a sex worker
- Spend it all on sex workers because your life will be dramatically improved for it

1 month ago 341 161 11 7

His lawyer was a bad ass too.

1 month ago 2 0 1 0

If you haven’t heard Lemon Pound Cake by Afroman yet, do it now. It is *chef’s kiss*

Enjoy your subsequent internet deep dive…

🍋🥮

1 month ago 12 1 2 1

Happy birthday 🎁 🎂

1 month ago 1 0 0 0

I hope your move is smooth and painless!

1 month ago 1 0 1 0

Oh for sure. Current hotel and airfare prices make it untenable to take those kinds of gambles on touring anymore. Not to mention the delays at so many airports right now are not worth dealing with if you don’t have to. So I’m staying put. Ç’est la vie 🤷‍♀️

1 month ago 1 0 0 0

Thank you darling 💖. Again, nature of the beast sometimes but it’s frustrating, especially when I get asked NOW for dates there 😤. Oh well, at least I’m avoiding the hellscape that is ohare…

1 month ago 1 0 1 0

Things have been picking up at home so at least there’s that. Might be a sign to slow down on touring and spend more time reconnecting with The Windy City 💖

1 month ago 1 0 1 0

Happy St Patrick’s Day gorgeous 💚

1 month ago 0 1 0 0
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