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
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
💌gem@professordemilo.com
🎆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
💌gem@professordemilo.com
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 🙏❤️
Gem@professordemilo.com
So if you’d like to help me recoup my losses, gift cards to Anthropologie, Abercrombie, Nordstrom or Lululemon would be immensely appreciated 🙏❤️
Gem@professordemilo.com
January 12, 2026 at 4:30 PM
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 🙏❤️
Gem@professordemilo.com
So if you’d like to help me recoup my losses, gift cards to Anthropologie, Abercrombie, Nordstrom or Lululemon would be immensely appreciated 🙏❤️
Gem@professordemilo.com
Me as a tree 🌳
January 8, 2026 at 11:00 PM
Me as a tree 🌳
How your email finds me 💌
January 7, 2026 at 5:18 PM
How your email finds me 💌
Reposted by Gem DeMilo ♥️ Chicago + Beyond
If you're looking for SW creators who actually use this app... I made a starter pack of active providers. real people, real content, none of that ghost account nonsense! ❤️ To be added, follow all & comment! go.bsky.app/QGLFqY7
January 7, 2026 at 12:18 AM
If you're looking for SW creators who actually use this app... I made a starter pack of active providers. real people, real content, none of that ghost account nonsense! ❤️ To be added, follow all & comment! go.bsky.app/QGLFqY7
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
💌gem@professordemilo.com
🎆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
💌gem@professordemilo.com
January 5, 2026 at 4:56 PM
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
💌gem@professordemilo.com
🎆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
💌gem@professordemilo.com
How tf does an airline manage to lose a piece of checked luggage on a direct domestic flight??
Beyond pissed…🤬
Beyond pissed…🤬
January 5, 2026 at 12:14 AM
How tf does an airline manage to lose a piece of checked luggage on a direct domestic flight??
Beyond pissed…🤬
Beyond pissed…🤬
Starting off the new year in The Big Easy quietly reflecting and celebrating in my own way:
11qp.substack.com/p/new-year-s...
11qp.substack.com/p/new-year-s...
New Year, Same Great Taste! 🎆
Welcoming 2026 with...not quite a bang. But meaningful celebration and reflection nevertheless.
11qp.substack.com
January 1, 2026 at 7:24 PM
Starting off the new year in The Big Easy quietly reflecting and celebrating in my own way:
11qp.substack.com/p/new-year-s...
11qp.substack.com/p/new-year-s...
Merry Christmas. Say it back ❤️💚
December 25, 2025 at 3:56 PM
Merry Christmas. Say it back ❤️💚
Officially on holiday hiatus ❤️💚
I’m going to be away from this precious dummy for 10 whole days 😭
I’m going to be away from this precious dummy for 10 whole days 😭
December 23, 2025 at 9:12 PM
Officially on holiday hiatus ❤️💚
I’m going to be away from this precious dummy for 10 whole days 😭
I’m going to be away from this precious dummy for 10 whole days 😭
Gem's Top 5 Holiday Movies 🎥✨
Plus some honorable mentions you won't want to miss this holiday season!
tinyurl.com
December 22, 2025 at 6:34 PM
Reposted by Gem DeMilo ♥️ Chicago + Beyond
Spend your Sunday on your knees 🛐💜
June 29, 2025 at 4:16 PM
Spend your Sunday on your knees 🛐💜
Believe me, I’m just as surprised by this as you are
December 20, 2025 at 6:44 PM
Believe me, I’m just as surprised by this as you are
Will you keep me cozy? ❄️
December 16, 2025 at 6:37 PM
Will you keep me cozy? ❄️
Could’ve sworn I put that thing somewhere…
December 11, 2025 at 2:30 PM
Could’ve sworn I put that thing somewhere…
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
There’s just something magical about having martinis in the middle of the afternoon at an old hotel bar🍸✨
December 3, 2025 at 11:46 PM
If you're a sex worker, quote with your fav recent lewd and how long you've been in the industry.
7 Years 💖
7 Years 💖
December 2, 2025 at 9:07 PM
If you're a sex worker, quote with your fav recent lewd and how long you've been in the industry.
7 Years 💖
7 Years 💖
I don’t get on my knees very often, but when I do it’s for you ❤️🔥
December 2, 2025 at 3:39 PM
I don’t get on my knees very often, but when I do it’s for you ❤️🔥
Reposted by Gem DeMilo ♥️ Chicago + Beyond
I just had a vegan Boston cream donut and I’m worried I might never experience joy like that ever again 😔
November 26, 2025 at 2:26 AM
I just had a vegan Boston cream donut and I’m worried I might never experience joy like that ever again 😔
You’ve been visited by three spirits.
The three spirits:
The three spirits:
November 25, 2025 at 1:21 AM
You’ve been visited by three spirits.
The three spirits:
The three spirits:
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? 🌝✨