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ChiChicago Bear

@chichicagobear.bsky.social
742 followers 770 following 283 posts

This is my #NSFW account. Consider yourself warned. Gen X. Martinis, dachshunds, nudism and awkwardness are my superpowers. Here for the noods, the flirts and the occasional NSFW sharing. Chicago is home 🇨🇱🏳️‍🌈🇺🇸 Not good at flirting but I’m a good kisser

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ChiChicago Bear @chichicagobear.bsky.social · 26/09/2026
Airport shower after a 8 hours flight.
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Reposted by ChiChicago Bear
Grandpa Chub Bear @handfree.bsky.social · 08/09/2025
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ChiChicago Bear @chichicagobear.bsky.social · 12/08/2026
Me, my belly and my nosey dog
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ChiChicago Bear @chichicagobear.bsky.social · 12/08/2026
Dick is dicking today.
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ChiChicago Bear @chichicagobear.bsky.social · 10/08/2026
Oh man, you have no idea. I miss the subtle coded approach, the kindness and even the bluntness that made things real.
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ChiChicago Bear @chichicagobear.bsky.social · 10/08/2026
I love when the randomized location situate profiles in impossible locations. i.e. In the middle of a lake
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ChiChicago Bear @chichicagobear.bsky.social · 10/08/2026
For those wondering what became of us after Market Days: some of us returned to the lake, as is tradition. We now hibernate in the silt, growing barnacles and dreaming of next year’s crowds. Do not disturb the water. Do not speak of us. We will emerge when the season calls. We always do.
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ChiChicago Bear @chichicagobear.bsky.social · 03/08/2026
It was brought to my attention that my butt looked cute. So here it is, you tell me.
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ChiChicago Bear @chichicagobear.bsky.social · 31/07/2026
In this economy?
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ChiChicago Bear @chichicagobear.bsky.social · 27/07/2026
❤️ hi cutie
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ChiChicago Bear @chichicagobear.bsky.social · 27/07/2026
So sexy
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ChiChicago Bear @chichicagobear.bsky.social · 25/07/2026
In a few days It’s going to be 10 years since I moved to USA. It feels time ran trough my fingers. Grateful for the people who welcomed me for who I am and I can call friends.
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ChiChicago Bear @chichicagobear.bsky.social · 24/07/2026
😈
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ChiChicago Bear @chichicagobear.bsky.social · 23/07/2026
Living my best #chunk era
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ChiChicago Bear @chichicagobear.bsky.social · 07/07/2026
Hi 👋
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ChiChicago Bear @chichicagobear.bsky.social · 02/07/2026
I would have liked that
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ChiChicago Bear @chichicagobear.bsky.social · 02/07/2026
Once, someone went too hard on my dick—doing some kind of nibbling while giving me head—and I got a nasty bruise on the shaft. I called my penis ‘Bruise Dickinson’ for a week Thank you for your attention.
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ChiChicago Bear @chichicagobear.bsky.social · 12/06/2026
Business in the streets, tighty withies in the…
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ChiChicago Bear @chichicagobear.bsky.social · 26/05/2026
He is gorgeous
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ChiChicago Bear @chichicagobear.bsky.social · 18/05/2026
I might or might not go to Atlanta next week, from Tuesday to Wednesday. That’s all, throwing that into the universe
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ChiChicago Bear @chichicagobear.bsky.social · 11/05/2026
New shirt
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ChiChicago Bear @chichicagobear.bsky.social · 04/05/2026
Handsome
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ChiChicago Bear @chichicagobear.bsky.social · 30/04/2026
Love Rafaella, and those are facts!
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ChiChicago Bear @chichicagobear.bsky.social · 27/04/2026
You’re very kind 😘
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ChiChicago Bear @chichicagobear.bsky.social · 27/04/2026
Oh hey, hi 👋
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ChiChicago Bear @chichicagobear.bsky.social · 04/04/2026
Who said butt?
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ChiChicago Bear @chichicagobear.bsky.social · 23/03/2026
*Slowly applauding, signaling approval
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ChiChicago Bear @chichicagobear.bsky.social · 22/03/2026
Ha! In this economy!
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ChiChicago Bear @chichicagobear.bsky.social · 22/03/2026
Consult by DM
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ChiChicago Bear @chichicagobear.bsky.social · 15/03/2026
Felt sexy, might delete later
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
Looking back, that was probably my first crush on a man that didn’t come wrapped in shame. I was feral Just a smile, a locker room, and a very confusing internship perk I definitely did not list on my résumé. 😅 (7/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
Was he flirting? Or just being nice to the awkward dude? Probably the latter. But I will admit there was at least one day I had to take a quick “strategic regrouping” break in a stall just so I could go back to my cubicle and pretend I was thinking about journalism. (6/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
There was one guy I remember in particular. Big daddy-looking press operator. We made eye contact a few times. He smiled once while we were waiting for the bus outside. Another time when I was heading toward that bathroom. We never spoke. We only smiled. Maybe he knew. Maybe he didn’t (5/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
Big working-class dudes casually walking around naked like it was the most normal thing in the world. Meanwhile I’m there at the urinal trying to act professional while my very gay brain is going: “Cool. Cool. Very normal me all dressed in my cheap suit, peeing surrounded by naked me” (4/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
That bathroom connected to the locker room for the press operators. The presses ran 24/7, so guys were constantly coming and going, ending shifts, changing clothes, showering. Which is how I learned those guys had zero locker-room modesty. (3/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
During my explorations I discovered something operationally important: The “office people” bathroom was farther away than a shared bathroom near the printing floor. As a responsible intern committed to efficiency… I optimized. (2/7)
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ChiChicago Bear @chichicagobear.bsky.social · 11/03/2026
This picture triggered a core memory 🧵 My first internship was at a big newspaper. My cubicle was in one building, while the printing press lived in the building next door. Important context: the whole place was a labyrinth. 1/7
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ChiChicago Bear @chichicagobear.bsky.social · 03/03/2026
So, I’m heading to Gardiner, NY for work. What’s fun in there, I’ve never been and I’ll have some free time
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ChiChicago Bear @chichicagobear.bsky.social · 03/03/2026
Happy monochromatic Monday for the ones who celebrate
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ChiChicago Bear @chichicagobear.bsky.social · 11/02/2026
Men of a Certain Age thread. 40+ besties drop a (non nude) selfie.
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ChiChicago Bear @chichicagobear.bsky.social · 08/02/2026
My favorite snack betrayed me. Now with the crown of my molar split in two I’m asking for respect and privacy as the rolled corn tortilla chips and I re evaluate our future together.
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ChiChicago Bear @chichicagobear.bsky.social · 07/02/2026
New game: every time I see guys in full gear, wearing long sport socks with a squared shaped bump I wonder: Poppers or ankle monitor?
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ChiChicago Bear @chichicagobear.bsky.social · 02/02/2026
Love is so obvious and so hard to explain sometimes.
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ChiChicago Bear @chichicagobear.bsky.social · 31/01/2026
My friend’s idea: “Let’s host an orgy at the theater where Melania’s documentary is screening” I believe that idea has legs, it’s gonna be empty anyways.
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ChiChicago Bear @chichicagobear.bsky.social · 30/01/2026
You are more than welcome
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ChiChicago Bear @chichicagobear.bsky.social · 30/01/2026
Well, I guess we must to spend quality time at NAB, otherwise I’ll not see you until next year
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ChiChicago Bear @chichicagobear.bsky.social · 30/01/2026
@cuddlechunk.bsky.social hey babe, I’ll see you at NAB and WX ?
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ChiChicago Bear @chichicagobear.bsky.social · 28/01/2026
Me easily lifting the aisle armrest in a commercial flight, looking at the dude across, trying to do the same and failing.
media.tenor.com
a woman wearing a t-shirt that says trust the sience
ALT: a woman wearing a t-shirt that says trust the sience
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ChiChicago Bear @chichicagobear.bsky.social · 28/01/2026
Licks 👅
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ChiChicago Bear @chichicagobear.bsky.social · 27/01/2026
@thatjeffisfunny.bsky.social you are so funny AND handsome ;)
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