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 🔒
Hope everyone is staying warm through the storm. Come on out to @jackhammerchicago.bsky.social on Sunday, December 7th to mingle with some fellow chastity enthusiasts. See you there!
So excited that we have a home bar at @jackhammerchicago.bsky.social now! All are welcome, locked 🔒, key holders, or cage curious. #chastity
@chicagochastity.bsky.social @chastity.social
@chicagochastity.bsky.social @chastity.social
December 1, 2025 at 1:49 AM
Hope everyone is staying warm through the storm. Come on out to @jackhammerchicago.bsky.social on Sunday, December 7th to mingle with some fellow chastity enthusiasts. See you there!
Reposted by Leather boy Jackson Boyd 🔒
Reposted by Leather boy Jackson Boyd 🔒
Black Friday sale! 50% off the OF all weekend. Treat yoself!
November 28, 2025 at 7:26 PM
Black Friday sale! 50% off the OF all weekend. Treat yoself!
Reposted by Leather boy Jackson Boyd 🔒
Some more Tubby Bear in Pants 🩲🌈🐾🧸🔁
More Stuff --> linktr.ee/bluboosh
More Stuff --> linktr.ee/bluboosh
November 26, 2025 at 3:14 PM
Some more Tubby Bear in Pants 🩲🌈🐾🧸🔁
More Stuff --> linktr.ee/bluboosh
More Stuff --> linktr.ee/bluboosh
Reposted by Leather boy Jackson Boyd 🔒
Happy Thanksgiving to everyone (even if you don’t celebrate you should still enjoy the day). Thank you to all the beautiful people that keep making my bsky experience what it is. I may not know you very well, but there are more than a few of you that i like more than some of my irl friends. 😉
November 27, 2025 at 10:30 PM
Happy Thanksgiving to everyone (even if you don’t celebrate you should still enjoy the day). Thank you to all the beautiful people that keep making my bsky experience what it is. I may not know you very well, but there are more than a few of you that i like more than some of my irl friends. 😉
Reposted by Leather boy Jackson Boyd 🔒
inspired by @jacksonboyd.bsky.social
Thanks for sharing me what is
#tightywhities 😘very sexy
________
commissions open and patreon open
Thanks for sharing me what is
#tightywhities 😘very sexy
________
commissions open and patreon open
November 27, 2025 at 5:48 PM
inspired by @jacksonboyd.bsky.social
Thanks for sharing me what is
#tightywhities 😘very sexy
________
commissions open and patreon open
Thanks for sharing me what is
#tightywhities 😘very sexy
________
commissions open and patreon open
I really connect with my queer identity under a masculine perspective, but we also have to recognize that masculinity has been used as a tool to deny and impose misogyny upon the world for too long. We should be finding what makes our masculinity positive and nourishing that.
November 27, 2025 at 5:40 PM
I really connect with my queer identity under a masculine perspective, but we also have to recognize that masculinity has been used as a tool to deny and impose misogyny upon the world for too long. We should be finding what makes our masculinity positive and nourishing that.
Reposted by Leather boy Jackson Boyd 🔒
Dad offering up some bulge on this tighty-whitey tummy Tuesday
June 17, 2025 at 7:19 PM
Dad offering up some bulge on this tighty-whitey tummy Tuesday
Reposted by Leather boy Jackson Boyd 🔒
Hey slugger! You enjoy coming to the cigar lounge with your old man?
November 24, 2025 at 1:17 PM
Hey slugger! You enjoy coming to the cigar lounge with your old man?
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?