Reposted by Jackson Bradley (Chicago)C. @thenewboyintown.bsky.social · 01/10/2026give it a follow 📸 www.instagram.com/cgt.photo?st... 3777
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 07/10/2026Perfect weather for hoodies and no undies! 020
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 07/10/2026Let’s start a follow thread! If you want to be a little more in touch with me, FOLLOW ME ON INSTAGRAM. Share yours and I’ll give you a follow! 040
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 06/10/2026Where are my batebuds at? Comment below! 😈💦 150
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20/11/2024Who wants to keep my ass warm? #humpday #chicago 2222
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 23/11/2024Good morning 😉 0201
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 12/12/2024Who’s going to keep me warm tonight? #humpday 1253
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 30/12/2024Happy Monday yall. 0273
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 12/02/2025Happy #Humpday 1231
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 20/02/2025Hope yall had a good #humpday Goodnight 😈 #gay #scruff #repost #daddy #woof #ass 0571
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 05/03/2025You share my hump on #humpday I’ll give you a discount code 🍑💦😈 Onlyfans.com/jacksonbradley #gay #men #daddy #sexy #ass #hump #Wednesday #wet #shower 1472
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 27/03/2025It’s still hump day right? 1131
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/05/2025Happy Hump Day! #humpday #ass #fatass #gay #daddy #sexy #woof #follow 1614
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 06/08/2025Repost with your favorite #humpday pic! #gay #daddy #zaddy #sexy #scruffy 1511
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 29/10/2025It’s my favorite day! So let’s see you asses out! Post your favorite #humpday pic! 1483
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/11/2025Peekaboo, my ass needs you! #humpday 3443
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/10/2026I really need to go back and recreate this with someone. 😈 020
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 02/01/2026New Year, Same Queer! Show Daddy love! #happynewyear #daddy #chicago #gay 2362
Reposted by Jackson Bradley (Chicago)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 3424
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 07/05/2026Sometimes attention is deserved… Do I have yours? Let me know in the comments. #humpday #daddy #sexy #gay #chicago 3502
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/10/2026Who conditions their pubs? Lol 020
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 01/10/2026Let’s see those #humpday photos! Drop them in the comments! My fav will get a free subscription! 😈💦 030
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 29/09/2026I wanna know who uses toys and what kind! Show me your favs! 😈 120
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/09/2026It’s another way for people to promote theirs OFs and content. Just depends on how you keep up with it. 001
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/02/2026What’s your best glute workout? I wanna see that ass! #humpday #ass #gay #daddy #woof #scruffy 2505
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/02/2026Shower before bed… come dry me off! #shower #clean #gay #reshare #follow #daddy #repost #sexy #scruff #bush 0492
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 26/06/2026It’s #ThirstyThursday… Tell me you want more in the comments! #gay #daddy #share #woof #sexy #chicago #pride #scruff 3534
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 28/07/2026Daddy is signing off. Goodnight boy…. You better say it back… #gay #daddy #chicago #scruff #zaddy 1222
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 06/08/2026It’s gonna be an amazing weekend 020
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026Just some more of my work with @luxgogo.bsky.social 020
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026Who took and edited this stunning photostatic.klipy.comSuspicious Baby Side Eye ReactionALT: Suspicious Baby Side Eye Reaction 010
Reposted by Jackson Bradley (Chicago)Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026Just catching the golden hour in Chicago and had to show the jock some love! What’s your favorite jock! Show be in the comments. 1171
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026Can I be your #mancrush Monday? 070
Jackson Bradley (Chicago) @jacksonbradley.bsky.social · 04/08/2026Just catching the golden hour in Chicago and had to show the jock some love! What’s your favorite jock! Show be in the comments. 1171
