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ChiTownHole

@chitownhole.bsky.social
2.3K followers 3.1K following 2.2K posts

Alt account for my slutty ways🔞 Aspiring cumdump 🕳️ looking for tops, bate buddies & friends. Absolutely no 🎉 or MAGA gays. 🏠Chicago | 🏳️‍🌈 | 🖖🏽 #teambottom #chicagobottom #rawislaw

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ChiTownHole @chitownhole.bsky.social · 1h
🔥
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ChiTownHole @chitownhole.bsky.social · 14h
Thank you!
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ChiTownHole @chitownhole.bsky.social · 14/10/2026
Thank you. I am told it looks even better when balls deep in it 😈😘
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ChiTownHole @chitownhole.bsky.social · 14/10/2026
Magnificent
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
I call those tops, “true gentlemen”.
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
One day I wish to get a photo like this
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Also I had a fun encounter with another bottom who made out with my hole so deeply and passionately it caught the attention the many voyeurs.
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
static.klipy.com
David Rose's Iconic 'Obviously' Moment
ALT: David Rose's Iconic 'Obviously' Moment
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
I do love getting pounded to within an inch of my life by an anonymous guy but I also love making out with a guy as we bate together.
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Fear of this exact scenario is why I bought a denim apron because I am always naked at home.
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Need to do this
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Magnificent
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Woke up today and my hole is not sore at all. The human body is amazing!
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ChiTownHole @chitownhole.bsky.social · 13/10/2026
Oh my that was an intense night at the bathhouse. I was fucked by some of the largest cocks I have encountered in a while, back-to-back. I had 3 prostate orgasms, thereby losing all coherency of speech to the poundings I was taking. I became a babbling gaped hole. It was amazing.
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ChiTownHole @chitownhole.bsky.social · 12/10/2026
This weather has me feeling feral as f**k. Thinking of going to @steamworkschi.bsky.social tonight for the @cumunion.bsky.social party. Any others of #gaychicago going?
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Reposted by ChiTownHole
John Coons/Teo @johncoons.bsky.social · 11/10/2026
CHICAGO! We're bringing our show Double InDUMBnity back to the Newport Theater 11/19 for a victory lap! If you missed out last time because we sold out, this one is for you! www.eventbrite.com/e/john-jonah...
eventbrite.com
John & Jonah in Double InDUMBnity
Following their shows BLEAK! and Nocturnal Omissions, your favorite adult cabaret clowns, John and Jonah are back at the Newport Theater!
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Reposted by ChiTownHole
Pup Zane @pupszane.bsky.social · 09/10/2026
Happy #fcf 😏🤭🍆
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ChiTownHole @chitownhole.bsky.social · 11/10/2026
Suddenly I want to be a table.
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ChiTownHole @chitownhole.bsky.social · 11/10/2026
Getting fucked with a view of the ocean is next level.
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Reposted by ChiTownHole
𝗕𝘂𝗹𝗹𝗕𝗼𝘀𝘀𝗝𝗼𝘀𝗵 @bullbossjosh.bsky.social · 10/10/2026
During my lectures we explore every inch of your slutty black hole 🕳️
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ChiTownHole @chitownhole.bsky.social · 11/10/2026
Oh my gape!
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ChiTownHole @chitownhole.bsky.social · 11/10/2026
Why is this turning me on so much?
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ChiTownHole @chitownhole.bsky.social · 10/10/2026
Goals
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ChiTownHole @chitownhole.bsky.social · 10/10/2026
Asstastic
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ChiTownHole @chitownhole.bsky.social · 09/10/2026
Magnificent
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
True cumraderie is taking turns holding the bottoms cheeks apart so your fellow top can get in deeper.
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Sincere admiration
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
This #Jocktober it seems nobody is posting what should be the official song of the month: youtu.be/h5kw9xqEed4?...
youtu.be
Jockstrap
YouTube video by HungerFF - Topic
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Oh my yes!
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
These cakes’ gravity pull is too strong for this world.
static.klipy.com
Fat Tony Fat Tony Dies In A Black Hole
ALT: Fat Tony Fat Tony Dies In A Black Hole
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Pure genius!
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Until the piano on the beach was on fire.
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Damn so much cake it give me the diabeetus
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Red
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
static.klipy.com
Sisqo - Thong Song Music Video
ALT: Sisqo - Thong Song Music Video
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ChiTownHole @chitownhole.bsky.social · 08/10/2026
Magnificent
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Reposted by ChiTownHole
Sunday Bunday @sundaybunday.bsky.social · 07/10/2026
Help me, Bluesky! You’re my only hope! *sound on*
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
static.klipy.com
Madonna Getting Wet in Water Splash
ALT: Madonna Getting Wet in Water Splash
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
I have a special tool that can be used to get an objective answer to this question.
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
Magnificent. As a man who likes suits do you like me also wear a jockstrap with a suit?
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
Wasn‘t planning on taking loads but got hit up by a regular I had not seen in a minute. He gets off when I talk about how other guys will use his cum as lube. So as to not be a liar, I took 2 other loads tonight. #feralfall
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
static.klipy.com
Lion King: Mufasa & Simba at Sunset
ALT: Lion King: Mufasa & Simba at Sunset
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
What if we fell in love getting a facial from the same cock?
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ChiTownHole @chitownhole.bsky.social · 07/10/2026
Magnificent
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ChiTownHole @chitownhole.bsky.social · 06/10/2026
I support this
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ChiTownHole @chitownhole.bsky.social · 05/10/2026
The only proper length for jorts:
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ChiTownHole @chitownhole.bsky.social · 05/10/2026
Nothing like a morning romp to put a smile on my face for this Monday morning.
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ChiTownHole @chitownhole.bsky.social · 05/10/2026
Magnificent
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ChiTownHole @chitownhole.bsky.social · 05/10/2026
I looked up “smoldering look” in the dictionary and I found this hottie staring at me through my phone.
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ChiTownHole @chitownhole.bsky.social · 05/10/2026
Well done!
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