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ChiChicago Bear

@chichicagobear.bsky.social
739 followers 769 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
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 · 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 · 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
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 · 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 · 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 · 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
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
@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 · 27/01/2026
@thatjeffisfunny.bsky.social you are so funny AND handsome ;)
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ChiChicago Bear @chichicagobear.bsky.social · 23/01/2026
Hi Palm Springs. I’m in you
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ChiChicago Bear @chichicagobear.bsky.social · 14/01/2026
First drawing class of the year!
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ChiChicago Bear @chichicagobear.bsky.social · 26/12/2025
If you are watching Strangers Things, you would agree with me that “that room” is covered with cum, wall to wall.
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ChiChicago Bear @chichicagobear.bsky.social · 25/11/2025
Channeling dad vibes
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ChiChicago Bear @chichicagobear.bsky.social · 19/11/2025
Hive mind! I’ll be in California with some free time the week of 01/19. Trying to decide if I stay in San Diego, go to LA or Palm Springs for the weekend. Any input you want to share?
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ChiChicago Bear @chichicagobear.bsky.social · 03/11/2025
Oh, hey there…
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ChiChicago Bear @chichicagobear.bsky.social · 10/10/2025
So is it only me the one who hates the “moments” feature on #scruff ? I wake up with a series of pictures of random folks and have no control over who I’m allowing to connect or follow.
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ChiChicago Bear @chichicagobear.bsky.social · 08/10/2025
Fall on the top, spring in the bottom
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ChiChicago Bear @chichicagobear.bsky.social · 08/10/2025
I was at the Halloweencostumesdotcom site looking for an adult plus size costume and I want to report their model is quite sexy.
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ChiChicago Bear @chichicagobear.bsky.social · 01/10/2025
Memory from Nice.
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ChiChicago Bear @chichicagobear.bsky.social · 29/09/2025
Really nice comeback to normal after a long vacation in Europe. This Saturday was fun, I went to Steamworks and it was a great. Good crowd and not too stressful. Also the steam room was on point.
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ChiChicago Bear @chichicagobear.bsky.social · 22/09/2025
Is the rapture same thing as a fisure?
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ChiChicago Bear @chichicagobear.bsky.social · 22/09/2025
Is there a “hookup apps etiquette” crash course available online? I would like to have that link handy as a reply to some of the messages I’m getting lately.
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ChiChicago Bear @chichicagobear.bsky.social · 21/09/2025
I’ll be in Minneapolis for work in a few weeks. What’s fun there?
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ChiChicago Bear @chichicagobear.bsky.social · 12/09/2025
Hello boys
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ChiChicago Bear @chichicagobear.bsky.social · 10/09/2025
Hi daddy…
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ChiChicago Bear @chichicagobear.bsky.social · 07/09/2025
I guess you cannot get an oligarch hookup in Monaco
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ChiChicago Bear @chichicagobear.bsky.social · 05/09/2025
This dad has been on a plane for over 7 hours. Taking advantage of the airport facilities in BCN to take a shower while waiting for my next flight.
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ChiChicago Bear @chichicagobear.bsky.social · 05/09/2025
It tracks www.instagram.com/reel/DOJY0eZ...
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ChiChicago Bear @chichicagobear.bsky.social · 02/09/2025
I have a solid costume choice for Halloween this year, just need the party.
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ChiChicago Bear @chichicagobear.bsky.social · 31/08/2025
Oh hey there 👋
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ChiChicago Bear @chichicagobear.bsky.social · 16/08/2025
My rule is 3 follow ups and no response… I move on. What’s yours?
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