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bearinchicago.bsky.social
BearInChicago
@bearinchicago.bsky.social
1.9K followers 1.4K following 250 posts
Chi stoner Daddy, Single in his 30s. Body +. Jock Straps++. #findom cash app- $ Chiguy88. Dom tendencies
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bearinchicago.bsky.social
BearInChicago @bearinchicago.bsky.social · May 29
Figured yall would want the video and cum shot from the pic the other day. Pretty verbal and the cum shot was massive.
bearinchicago.bsky.social
Fat ass and a Fat tongue 😈

Am I riding your face, or you riding mine?
December 12, 2025 at 4:26 PM
Reposted by BearInChicago
forestcliff.bsky.social
Just chillin
December 11, 2025 at 4:46 PM
bearinchicago.bsky.social
I hope the truckers saw me 😈
December 10, 2025 at 9:13 PM
bearinchicago.bsky.social
Wood morning 😈
December 8, 2025 at 3:33 PM
bearinchicago.bsky.social
NYC was epic
December 7, 2025 at 7:02 PM
bearinchicago.bsky.social
Did yall find you a big boy for cuffing season yet?
November 22, 2025 at 9:51 PM
bearinchicago.bsky.social
Need rubs
November 19, 2025 at 10:06 PM
bearinchicago.bsky.social
Hi kids! 👋🏼👋🏼
November 14, 2025 at 8:36 PM
bearinchicago.bsky.social
On the road back to Chicago. Of course. I’m being a hoe at the truck stops.
November 11, 2025 at 6:44 PM
bearinchicago.bsky.social
Couldn’t decide if I liked em separate or together. So yall get all 3 😈
November 7, 2025 at 10:50 PM
bearinchicago.bsky.social
Belly Check!
Add yours!
October 23, 2025 at 3:28 PM
bearinchicago.bsky.social
Ya boy needs some road head 😈

Catch all my car antics here

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October 22, 2025 at 5:20 PM
bearinchicago.bsky.social
It’s not hump day, but I was feeling cheeky 😈
October 14, 2025 at 2:57 PM
bearinchicago.bsky.social
Really need some hep with this today.

And don’t forget to slap my balls around 😈 #cbt
September 30, 2025 at 6:26 PM
bearinchicago.bsky.social
Needs to be loaded. Immediately.
September 24, 2025 at 11:23 PM
bearinchicago.bsky.social
A full moon at 8am?

Eat up, fellas 😈
September 23, 2025 at 12:50 PM
bearinchicago.bsky.social
Someone told me I have a “pretty cock”. Thoughts?
September 15, 2025 at 7:34 PM
bearinchicago.bsky.social
Mini road trips means belly shots at truck stops
September 13, 2025 at 2:20 PM
bearinchicago.bsky.social
Just me in the back yard blowing a massive load 💦

Watch it in full onlyfans.com/bearinchicago
September 9, 2025 at 7:13 PM
bearinchicago.bsky.social
You jumpin in or nah?
September 8, 2025 at 6:53 PM
bearinchicago.bsky.social
I’m so heavily addicted to gooning my dick at the park. I need someone’s hand or hole.

Uploading a 7 min video tonight where I cum while locking eyes with the dude in the car next to me 😈

onlyfans.com/bearinchicago
September 4, 2025 at 1:30 PM
bearinchicago.bsky.social
See those indentions?

That’s where your hands go before you smush that face in my belly.

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August 28, 2025 at 5:16 PM
bearinchicago.bsky.social
You pull up next to me at the forest preserve, see me breathing heavy, sweaty, #gooning out in my car. Cock throbbing, balls heavy…..

What do you do?

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August 27, 2025 at 1:00 PM
bearinchicago.bsky.social
All the belly you need, and more 😈

onlyfans.com/bearinchicago
August 25, 2025 at 12:12 PM
bearinchicago.bsky.social
What’re you boys up to, this gorgeous Sunday?

And yea….that spot is from my dick leaking 😈

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August 24, 2025 at 6:03 PM