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🔒
➡️MAL➡️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🔒
➡️MAL➡️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...
Reposted by Leather boy Jackson Boyd 🔒
Id tell you that my eyes are up here, but it looks like you've already spotted the reward for being such a good boy for dad.
Catch dad in my tighty whities hosting at @jackhammerchicago.bsky.social every second Thursday starting in December for Brief Encounters.
Catch dad in my tighty whities hosting at @jackhammerchicago.bsky.social every second Thursday starting in December for Brief Encounters.
November 25, 2025 at 3:28 PM
Id tell you that my eyes are up here, but it looks like you've already spotted the reward for being such a good boy for dad.
Catch dad in my tighty whities hosting at @jackhammerchicago.bsky.social every second Thursday starting in December for Brief Encounters.
Catch dad in my tighty whities hosting at @jackhammerchicago.bsky.social every second Thursday starting in December for Brief Encounters.
Yall know I’m #tightywhities obsessed. It runs deep in me since early childhood as did the shame. My upcoming TW monthly event at @jackhammerchicago.bsky.social is not just important to me for being fun, but as a statement I’m proud of my funny little fetish and I’m happy I’m not alone anymore.
November 26, 2025 at 5:42 PM
Yall know I’m #tightywhities obsessed. It runs deep in me since early childhood as did the shame. My upcoming TW monthly event at @jackhammerchicago.bsky.social is not just important to me for being fun, but as a statement I’m proud of my funny little fetish and I’m happy I’m not alone anymore.
If you see this post your getaway vehicle
November 26, 2025 at 12:26 PM
If you see this post your getaway vehicle
I know having a crush on Jason Kelce is basic af but come on…look at this man and tell me you wouldn’t watch a someone like this change in the locker room.
November 26, 2025 at 4:45 AM
I know having a crush on Jason Kelce is basic af but come on…look at this man and tell me you wouldn’t watch a someone like this change in the locker room.
Reposted by Leather boy Jackson Boyd 🔒
August 15, 2024 at 4:34 PM
Goals
November 23, 2025 at 8:35 PM
Goals
Reposted by Leather boy Jackson Boyd 🔒
Come out to the first #tightywhities night at @jackhammerchicago.bsky.social and sport your favorite skivies.
November 19, 2025 at 5:14 AM
Come out to the first #tightywhities night at @jackhammerchicago.bsky.social and sport your favorite skivies.
Reposted by Leather boy Jackson Boyd 🔒
obsessed with small penis
inspired by @jacksonboyd.bsky.social
inspired by @jacksonboyd.bsky.social
November 20, 2025 at 6:22 PM
obsessed with small penis
inspired by @jacksonboyd.bsky.social
inspired by @jacksonboyd.bsky.social
November 20, 2025 at 1:34 PM
@bobren.bsky.social makes me look so cuddly
November 19, 2025 at 1:21 PM
@bobren.bsky.social makes me look so cuddly
Come out to the first #tightywhities night at @jackhammerchicago.bsky.social and sport your favorite skivies.
November 19, 2025 at 5:14 AM
Come out to the first #tightywhities night at @jackhammerchicago.bsky.social and sport your favorite skivies.
@bobren.bsky.social liked my #tightywhities so they drew my butt in some. Anyone want to run their hands on me like this?
November 18, 2025 at 4:08 PM
@bobren.bsky.social liked my #tightywhities so they drew my butt in some. Anyone want to run their hands on me like this?
Reposted by Leather boy Jackson Boyd 🔒
something happened in the elevator🥵
November 6, 2025 at 4:38 PM
something happened in the elevator🥵
@bodieswithbooks.bsky.social
#bodieswithbooks
#bodieswithbooksproject
The new show has been so good too
#bodieswithbooks
#bodieswithbooksproject
The new show has been so good too
November 18, 2025 at 3:11 AM
@bodieswithbooks.bsky.social
#bodieswithbooks
#bodieswithbooksproject
The new show has been so good too
#bodieswithbooks
#bodieswithbooksproject
The new show has been so good too
Something so hot about sightings like these
November 17, 2025 at 6:16 PM
Something so hot about sightings like these
Reposted by Leather boy Jackson Boyd 🔒
Bearracuda tonight in PDX! Jock or Tightey Whiteys?
November 16, 2025 at 1:57 AM
Bearracuda tonight in PDX! Jock or Tightey Whiteys?
Reposted by Leather boy Jackson Boyd 🔒
In case you didn't know, @seattledad.bsky.social and I met and it was everything I've ever wanted. 30+ minute video going up on JFF later today also feat. @chibear20.bsky.social
August 29, 2025 at 6:49 PM
In case you didn't know, @seattledad.bsky.social and I met and it was everything I've ever wanted. 30+ minute video going up on JFF later today also feat. @chibear20.bsky.social
The face / the cheeks
November 13, 2025 at 1:03 PM
The face / the cheeks
Come out to @bearunion.bsky.social at @cellblockchi.bsky.social 3-8PM
Hosted by @chibear20.bsky.social @chicub87.bsky.social @gazbearington.bsky.social
Hosted by @chibear20.bsky.social @chicub87.bsky.social @gazbearington.bsky.social
November 5, 2025 at 12:27 AM
Come out to @bearunion.bsky.social at @cellblockchi.bsky.social 3-8PM
Hosted by @chibear20.bsky.social @chicub87.bsky.social @gazbearington.bsky.social
Hosted by @chibear20.bsky.social @chicub87.bsky.social @gazbearington.bsky.social
Reposted by Leather boy Jackson Boyd 🔒
Saddle up! Photo shoot with Grant.
October 25, 2025 at 1:53 AM
Saddle up! Photo shoot with Grant.
For #locked day 100 Dad said he wanted me to fuck my hole and rub the loads on my mustache. A good boy does as he’s told. (Love doing video requests)
October 24, 2025 at 3:37 PM
For #locked day 100 Dad said he wanted me to fuck my hole and rub the loads on my mustache. A good boy does as he’s told. (Love doing video requests)
Cooking up something soon…
October 23, 2025 at 11:07 PM
Cooking up something soon…
Reposted by Leather boy Jackson Boyd 🔒
Tighty whities Dad at the very end of humpday. And you can see even more of Dad at the link in my bio. #dad #daddy #tightywhities #whitebriefs #humpdayworthy #humpday
October 23, 2025 at 4:55 AM
Tighty whities Dad at the very end of humpday. And you can see even more of Dad at the link in my bio. #dad #daddy #tightywhities #whitebriefs #humpdayworthy #humpday