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ChicagoCigarDad 🍆🍑

@chicagocigardad.bsky.social
14.4K followers 16.1K following 1.1K posts

Ask and ye shall receive.

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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 12h
It’s ok. Yippee.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 12h
Happy Fat Cock Friday…….from prison. #fcf #fatcockfriday #chastity #caged #locked
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 15/10/2026
Have a thirsty Thursday.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 15/10/2026
New jockstrap from @sweatyjohnson69.bsky.social discovered that my ass looks better if I bend over. No wrinkles! Now to walk through life at a 90 degree angle. #jocktober #locktober #dadbid #dadcakes
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 14/10/2026
Kinky Hump Day Meat-Up at @chicagoeagle.bsky.social Wednesday.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 13/10/2026
Yes, of course I am.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 13/10/2026
Ah, sweet relief. #fatcock #dad #stroking
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 13/10/2026
New jock, old ass. Happy Jocktober! #jockstrap #jock #jocktober #dad #dadbutt #jockmail #cake
Dads ass in a jock
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 12/10/2026
Wooooooof!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 10/10/2026
Last night’s cage check. #locktober #caged #chastity #dad #dadbod
Dad showing his caged dick
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 10/10/2026
Showing off that VCL with @mrsleather.bsky.social and my Kink 3D Cobra, cause that beast is in prison! #showyourlock #vcl #mrsleather #caged #chastity #locktober #kink3d #cobra #dadbod
Dad showing off visible cage lines in his white briefs for Locktober, promoting Mr. S Leather and their amazing kink 3d cages
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Fair question. Well?
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Love that foreskin. Wooooof.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Happy fat cock Friday! We need a contest! Post them, post them, on the wall, see who’s fattest of them all. #fcf #fatcockfriday #dad #dadbod #chastity #caged #locked
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
I mean, what else you gonna do in #Locktober and this hammock is so restful !
Dad ass up in a sling.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Holy hell that’s thick!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Thick Ass Thursdays…..just to give those fat cocks something worth plumping up for tomorrow.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Showing off that @sweatyjohnson69.bsky.social jockstrap….doing the lord’s work keeping all that junk under control. #jock #jockstrap #dad #dadbod #thick
Dad in a black jock, peeling it down
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 09/10/2026
Cigars at @jackhammerchicago.bsky.social tomorrow night to end the week with a bang or two. Come tease and poke my cage.
As for Hot Ash Smokes At JACKKHAMMER, FRIDAY, 7-10.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 08/10/2026
Enjoy this file footage from the caged days of yore. Reminding everyone I do in fact have a dick.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 07/10/2026
Woooooof
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 06/10/2026
Where did you get this. I need it desperately!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 02/10/2026
Happy Fat Cock Friday! #fcf #fatcockfriday #dad
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 02/10/2026
Sticks and Dicks tonight at @jackhammerchicago.bsky.social
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 02/10/2026
Out celebrating the holidays! Have a happy #fatcockfriday #fcf #chastity #caged #dad #locktober
Dads caged cock in a glory hole Dad showing his caged cock in front of the chastity pride flag.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 02/10/2026
It’s Jocktober. It’s Locktober. How you gonna celebrate? A or B. #locktober #jocktober #chastity #caged #jock #jockstrap #daddy
Dads caged cock in a dirty jockstrap Dad’s ass in a dirty jock.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 01/10/2026
It’s the most wonderful time of the year! Happy Locktober, folks! #showyourlock #chastity #caged #dad #locktober @mrsleather.bsky.social
Dad in his cage showing a happy Locktober sign for the Mr S Leather competition.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 01/10/2026
Yup!!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 30/09/2026
A final moment of freedom before we plunge into #locktober. #pa #princealbert
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 30/09/2026
I am
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 30/09/2026
I am the King of the Caged!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 30/09/2026
Like I get to wait till October. This was just a rare treat because I had to go to the urologist :-(
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 29/09/2026
Who’s up for the challenge? #pa #princealbert #bigdick #dad
Looking up at dad’s fat cock.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 23/09/2026
Join is at the @chicagoeagle.bsky.social tonight!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 18/09/2026
Fat cock tease #fcf #fatxockfriday #dad
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 16/09/2026
Are you saying you don’t remember it?????
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 16/09/2026
What you gonna do about it? #pa #princealbert #fatcock #thicc
Dad’s fat cock.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 16/09/2026
Dat ass is pure jelly.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 12/09/2026
Who’s coming out tonight? Besides my weiner? #jock #jockstrap #dad
Dad in a black and yellow jockstrap and black tank top
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 12/09/2026
Happy #fatcockfriday #fcf what do you thiink. Length or girth, which matters most? #jock #jockstrap
Dads cock shaft
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 11/09/2026
Tonight at 7pm @jackhammerchicago.bsky.social
Dad smoking a cigar in sunglasses, text reads Hot Ash Snokes, Friday, Sept 11, 7-10pm, Jackhammer.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 10/09/2026
All those squats finally paying off. Also, looks like Scrat’s face. #ass #butt #bulge #dad #dadbod
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 07/09/2026
All locked up. I wonder what I’ll do now?? #caged #chastity
Dad in chastity
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 05/09/2026
Hope Saturday brings big things!
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 04/09/2026
The frustrating thing about bull balls is that the more you empty them the fuller they get. Literally a bottomless pit. #balls #bullballs #pa #princealbert #dad #daddy #fcf #fatcockfriday
Dad smoking with his dick out
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 04/09/2026
Fun with shadows and light. And a fat cock #pa #princealbert #fcf #fatcockfriday
Black and white photo of dad naked
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 04/09/2026
Just making the bed, nothing to see here #jockstrap #jock #dad #ass
Dads ass in a jock strap
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 03/09/2026
The bull’s tanks are FULL. #pa #princealbert #bullballs #dad #daddy
Dad having a cigar with his bull balls and pierced cock out.
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 31/08/2026
Kink 3D from @mrsleather.bsky.social
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ChicagoCigarDad 🍆🍑 @chicagocigardad.bsky.social · 31/08/2026
End of one week, beginning of another. Choose kindness this week.
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