Leather boy Jackson Boyd 🔒
@jacksonboyd.bsky.social
He/Him
-Chicago
-Bears, tighty whities, leather, cigars, chastity
-Boy to Cliff Boyd https://bsky.app/profile/chibear20.bsky.social
-💙Property of my Dad🔒
➡️Smokeout
BLUF#5641
RECON: leatherboyjackson
https://linktr.ee/chicagotwcub
BLM, 🏳️⚧️, 🇵🇸, 🇺🇦
-Chicago
-Bears, tighty whities, leather, cigars, chastity
-Boy to Cliff Boyd https://bsky.app/profile/chibear20.bsky.social
-💙Property of my Dad🔒
➡️Smokeout
BLUF#5641
RECON: leatherboyjackson
https://linktr.ee/chicagotwcub
BLM, 🏳️⚧️, 🇵🇸, 🇺🇦
Pinned
Jackson Boyd’s Briefs
jacksonboydsbriefs.bigcartel.com
Get your naughty hands on a pair of my signature tighty whities. They’re versatile like me! You can even wear them on your face!
I also offer various alterations that you can DM me about. 💦 🩲
jacksonboydsbriefs.bigcartel.com?_gl=1*1ynnq3...
I also offer various alterations that you can DM me about. 💦 🩲
jacksonboydsbriefs.bigcartel.com?_gl=1*1ynnq3...
Hey Chicago! Who am I seeing tomorrow at Brief Encounters?
@jackhammerchicago.bsky.social @theholechicago.bsky.social
@jackhammerchicago.bsky.social @theholechicago.bsky.social
February 11, 2026 at 6:05 PM
Hey Chicago! Who am I seeing tomorrow at Brief Encounters?
@jackhammerchicago.bsky.social @theholechicago.bsky.social
@jackhammerchicago.bsky.social @theholechicago.bsky.social
Not once has anyone ever shared an AI image where I went “wow, I’m so glad they shared that”
February 10, 2026 at 5:25 AM
Not once has anyone ever shared an AI image where I went “wow, I’m so glad they shared that”
Reposted by Leather boy Jackson Boyd 🔒
Reposted by Leather boy Jackson Boyd 🔒
Sunday is a day of rest
February 8, 2026 at 4:09 PM
Sunday is a day of rest
Reposted by Leather boy Jackson Boyd 🔒
Reposted by Leather boy Jackson Boyd 🔒
February 8, 2026 at 1:51 PM
Fact about me: I’m the complete opposite of a size queen. Show me your cock at literally any size and I’ll love it. Smaller cocks are often hotter and used better than larger ones anyways.
February 8, 2026 at 3:22 PM
Fact about me: I’m the complete opposite of a size queen. Show me your cock at literally any size and I’ll love it. Smaller cocks are often hotter and used better than larger ones anyways.
Rian Johnson said he’s not sure a muppets knives out movie is possible so I say have Benoit Blanc (not Daniel Craig) as a guest star like the original Star Wars muppet show special episode.
February 5, 2026 at 3:22 PM
Rian Johnson said he’s not sure a muppets knives out movie is possible so I say have Benoit Blanc (not Daniel Craig) as a guest star like the original Star Wars muppet show special episode.
Yeah I have a guilty pleasure with camo
February 2, 2026 at 4:07 PM
Yeah I have a guilty pleasure with camo
Reposted by Leather boy Jackson Boyd 🔒
So apparently Drag Race won't be available to stream/download for another 13 mins, so...should I spam you guys with thirst traps pulled from the archives while we wait? 😉
January 31, 2026 at 2:19 AM
So apparently Drag Race won't be available to stream/download for another 13 mins, so...should I spam you guys with thirst traps pulled from the archives while we wait? 😉
Brief Encounters Night is coming back up! Come join all the dads, lads, pets, and nerds in your most classic old-school underwear that makes you feel sexy. And if you don't have any, borrow some from your dad 😉 #tightywhities #BriefEncounters #gaychicago
January 30, 2026 at 4:01 PM
Brief Encounters Night is coming back up! Come join all the dads, lads, pets, and nerds in your most classic old-school underwear that makes you feel sexy. And if you don't have any, borrow some from your dad 😉 #tightywhities #BriefEncounters #gaychicago
Reposted by Leather boy Jackson Boyd 🔒
Today’s underwear
January 30, 2026 at 12:42 PM
Today’s underwear
The way that even if I was a millionaire I’d still only wear basic tighty-whities.
January 28, 2026 at 8:04 PM
The way that even if I was a millionaire I’d still only wear basic tighty-whities.
Not sure if other feel any similar ways but, topping for me is/was 85% physical and 15% mental whereas bottoming is 60% mental and 40% physical sensation. Because bottoming for me is a space I feel vulnerable and not in control. It’s a headspace thing
January 26, 2026 at 4:40 PM
Not sure if other feel any similar ways but, topping for me is/was 85% physical and 15% mental whereas bottoming is 60% mental and 40% physical sensation. Because bottoming for me is a space I feel vulnerable and not in control. It’s a headspace thing
Having a PA means straight guys looking at your dick in the locker room or urinal
January 26, 2026 at 2:42 PM
Having a PA means straight guys looking at your dick in the locker room or urinal
Does my hole come off as ‘welcoming’?
January 22, 2026 at 1:22 PM
Does my hole come off as ‘welcoming’?
Reposted by Leather boy Jackson Boyd 🔒
A special friend took some nice pics of me at MAL (after dropping a load in me)
January 21, 2026 at 4:33 PM
A special friend took some nice pics of me at MAL (after dropping a load in me)
Reposted by Leather boy Jackson Boyd 🔒
Hump day ☕. Make it a great one.
January 21, 2026 at 1:03 PM
Hump day ☕. Make it a great one.
Reposted by Leather boy Jackson Boyd 🔒
I now have proper briefs for my next spanking. Thank you, @jacksonboyd.bsky.social, for the recommendation to select the Fruits. Classic selection.
January 19, 2026 at 8:31 PM
I now have proper briefs for my next spanking. Thank you, @jacksonboyd.bsky.social, for the recommendation to select the Fruits. Classic selection.
Before and after. (Spanking)
January 16, 2026 at 11:45 PM
Before and after. (Spanking)
Reposted by Leather boy Jackson Boyd 🔒
Reskeet if you’re a bator and want other bators to add you 🤙
November 16, 2024 at 9:30 PM
Reskeet if you’re a bator and want other bators to add you 🤙
MAL bound (later today)
January 15, 2026 at 5:19 PM
MAL bound (later today)