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Jackson Bradley (Chicago)

@jacksonbradley.bsky.social
1.7K followers 653 following 457 posts

📍Chicago Photographer Content creator linktr.ee/Brad421

PostsRepliesMedia
Reposted by Jackson Bradley (Chicago)
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20/11/2024
Who wants to keep my ass warm? #humpday #chicago
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 23/11/2024
Good morning 😉
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 12/12/2024
Who’s going to keep me warm tonight? #humpday
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 30/12/2024
Happy Monday yall.
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 12/02/2025
Happy #Humpday
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20/02/2025
Hope yall had a good #humpday Goodnight 😈 #gay #scruff #repost #daddy #woof #ass
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 05/03/2025
You share my hump on #humpday I’ll give you a discount code 🍑💦😈 Onlyfans.com/jacksonbradley #gay #men #daddy #sexy #ass #hump #Wednesday #wet #shower
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 27/03/2025
It’s still hump day right?
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/05/2025
Happy Hump Day! #humpday #ass #fatass #gay #daddy #sexy #woof #follow
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 06/08/2025
Repost with your favorite #humpday pic! #gay #daddy #zaddy #sexy #scruffy
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 29/10/2025
It’s my favorite day! So let’s see you asses out! Post your favorite #humpday pic!
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/11/2025
Peekaboo, my ass needs you! #humpday
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 19h
I really need to go back and recreate this with someone. 😈
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 02/01/2026
New Year, Same Queer! Show Daddy love! #happynewyear #daddy #chicago #gay
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 30/04/2026
“Be honest… is it the eyes or the view that got you?” Don’t lie…. #humpday #sexy #goldenhour #scruff
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 07/05/2026
Sometimes attention is deserved… Do I have yours? Let me know in the comments. #humpday #daddy #sexy #gay #chicago
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 19h
#humpday throwback time
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 19h
Who conditions their pubs? Lol
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20h
Let’s see those #humpday photos! Drop them in the comments! My fav will get a free subscription! 😈💦
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 29/09/2026
I wanna know who uses toys and what kind! Show me your favs! 😈
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/02/2026
What’s your best glute workout? I wanna see that ass! #humpday #ass #gay #daddy #woof #scruffy
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/02/2026
Shower before bed… come dry me off! #shower #clean #gay #reshare #follow #daddy #repost #sexy #scruff #bush
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/06/2026
It’s #ThirstyThursday… Tell me you want more in the comments! #gay #daddy #share #woof #sexy #chicago #pride #scruff
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/07/2026
Daddy is signing off. Goodnight boy…. You better say it back… #gay #daddy #chicago #scruff #zaddy
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 07/08/2026
#fatcockfriday anyone?
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026
Just some more of my work with @luxgogo.bsky.social
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026
Just catching the golden hour in Chicago and had to show the jock some love! What’s your favorite jock! Show be in the comments.
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026
Can I be your #mancrush Monday?
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026
Just catching the golden hour in Chicago and had to show the jock some love! What’s your favorite jock! Show be in the comments.
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Vox the Dog @voxdoggo.bsky.social · 14/06/2026
Had a lot of fun in a dungeon this week. Videos going on my OF. First one is already up.
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/08/2026
Cakes by the ….
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20/05/2026
Just a little pup shoot!
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/07/2026
Wanna see how I cool off in this heat… Repost and share for an exclusive OF surprise! #gay #shower #daddy #zaddy #wet #chicago #scruff #chudai
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/07/2026
Someone was a good boy.. #pup #kink #gay #sniff #goodboy #chudai
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/07/2026
So hot I can’t seem to find my pants! #humpday #chudai #daddy #naked #men #gay
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 08/07/2026
Just a pup teasing daddy … If you want more like this… Share and like! #puppyplay #pup #gay #daddy #woof #sexy #kink #chudai
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max goldensun @xxxgoldensun.bsky.social · 31/07/2026
mic check (out now linky bio)
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Z. @ztafterdark.bsky.social · 31/07/2026
Booiiinnnngggg
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1-900-DAD-GOON @clarkstreetclone.bsky.social · 31/07/2026
Dad’s got your dinner ready. #fcf
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Former D-list Pornstar @alluvialmeat.bsky.social · 01/08/2026
one more for #fatcockfriday #fcf #gay #gayotter #gayhairy
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1-900-DAD-GOON @clarkstreetclone.bsky.social · 31/07/2026
Think with your heart not with your head. #fcf
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/08/2026
Great shot
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🐴 @obscureverses.bsky.social · 01/08/2026
Goodnight
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Joseph the Gray @josephthegray.bsky.social · 31/07/2026
Hotels make me #horny #fcf view while I help you take off my big boy pants
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 31/07/2026
Felt cute for #FCF might delete later…. Should I delete it or you gonna share it 😈 #fatcockfriday #gay #daddy #woof #chudai #gag #suckmydick
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 30/07/2026
Just reactivated my JJF! Stay tuned 😈
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/07/2026
Daddy is signing off. Goodnight boy…. You better say it back… #gay #daddy #chicago #scruff #zaddy
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 22/07/2026
Great shot and such a stud!
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 08/07/2026
Just a pup teasing daddy … If you want more like this… Share and like! #puppyplay #pup #gay #daddy #woof #sexy #kink #chudai
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Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 08/07/2026
Should I get a pup mask?? 🐾
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