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 🔒
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)
Reposted by Leather boy Jackson Boyd 🔒
You in High School vs you now…
January 14, 2026 at 7:46 PM
You in High School vs you now…
Reposted by Leather boy Jackson Boyd 🔒
What else am I supposed to do when there’s no one to hump on hump day? #tightywhities #hairybear
January 14, 2026 at 6:10 PM
What else am I supposed to do when there’s no one to hump on hump day? #tightywhities #hairybear
Reposted by Leather boy Jackson Boyd 🔒
Bulge bumping mode activated 😈 Happy #TummyTuesday #TightyWhitieTuesday!
January 14, 2026 at 2:52 AM
Bulge bumping mode activated 😈 Happy #TummyTuesday #TightyWhitieTuesday!
What do you sleep in? #tightywhities
January 13, 2026 at 5:13 AM
What do you sleep in? #tightywhities
Reposted by Leather boy Jackson Boyd 🔒
Someone poke this bear
January 13, 2026 at 2:40 AM
Someone poke this bear
Reposted by Leather boy Jackson Boyd 🔒
These seem more controversial… what do we think of tightie whities? Those who like em, love em, and those that don’t usually really dislike them. It seems not many people are in the middle. I’ve warmed up to them mostly because I know some people love em and I like to experiment, where do you fall?
January 7, 2026 at 3:43 AM
These seem more controversial… what do we think of tightie whities? Those who like em, love em, and those that don’t usually really dislike them. It seems not many people are in the middle. I’ve warmed up to them mostly because I know some people love em and I like to experiment, where do you fall?
Reposted by Leather boy Jackson Boyd 🔒
Now I know that @pocketwolfspitz.bsky.social can not be the only good pup that wants to come out and play with @jacksonboyd.bsky.social and daddy this Thursday down in @theholechicago.bsky.social 😈
Brief Encounters
THIS Thursday | 9pm
@jackhammerchicago.bsky.social
Brief Encounters
THIS Thursday | 9pm
@jackhammerchicago.bsky.social
January 5, 2026 at 11:24 PM
Now I know that @pocketwolfspitz.bsky.social can not be the only good pup that wants to come out and play with @jacksonboyd.bsky.social and daddy this Thursday down in @theholechicago.bsky.social 😈
Brief Encounters
THIS Thursday | 9pm
@jackhammerchicago.bsky.social
Brief Encounters
THIS Thursday | 9pm
@jackhammerchicago.bsky.social
Reposted by Leather boy Jackson Boyd 🔒
Happy New Year all!
That means it’s a week from more tighty whities fun at Brief Encounters hosted at @jackhammerchicago.bsky.social 🎉🩲
That means it’s a week from more tighty whities fun at Brief Encounters hosted at @jackhammerchicago.bsky.social 🎉🩲
January 2, 2026 at 5:31 AM
Happy New Year all!
That means it’s a week from more tighty whities fun at Brief Encounters hosted at @jackhammerchicago.bsky.social 🎉🩲
That means it’s a week from more tighty whities fun at Brief Encounters hosted at @jackhammerchicago.bsky.social 🎉🩲
Reposted by Leather boy Jackson Boyd 🔒
Thursday 1/8 @ 9PM
It’s time to go classic — crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition, where we celebrate the iconic look that started it all.
It’s time to go classic — crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition, where we celebrate the iconic look that started it all.
January 2, 2026 at 4:04 PM
Thursday 1/8 @ 9PM
It’s time to go classic — crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition, where we celebrate the iconic look that started it all.
It’s time to go classic — crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition, where we celebrate the iconic look that started it all.
Reposted by Leather boy Jackson Boyd 🔒
Started my new year off right with a bulk order of tighty whiteys. Come help me break them in next Thursday at Brief Encounters at @jackhammerchicago.bsky.social
January 2, 2026 at 6:32 PM
Started my new year off right with a bulk order of tighty whiteys. Come help me break them in next Thursday at Brief Encounters at @jackhammerchicago.bsky.social
2026 New Years Resolutions:
1. 25 books (non grad school)
2. Graduate
3. Get some tattoos
4. Continue to grow and establish Brief Encounters
1. 25 books (non grad school)
2. Graduate
3. Get some tattoos
4. Continue to grow and establish Brief Encounters
January 1, 2026 at 9:08 PM
2026 New Years Resolutions:
1. 25 books (non grad school)
2. Graduate
3. Get some tattoos
4. Continue to grow and establish Brief Encounters
1. 25 books (non grad school)
2. Graduate
3. Get some tattoos
4. Continue to grow and establish Brief Encounters
Reposted by Leather boy Jackson Boyd 🔒
When dad’s finished his meal, he starts rubbing and slapping his gut and gives you that look…Time for you to service his cock #tummytuesday
December 30, 2025 at 4:01 PM
When dad’s finished his meal, he starts rubbing and slapping his gut and gives you that look…Time for you to service his cock #tummytuesday
I took down the post about the possible n*zi. I have friends who know him IRL and can confirm it’s someone using his pictures with the added “tattoos”.
December 29, 2025 at 2:49 PM
I took down the post about the possible n*zi. I have friends who know him IRL and can confirm it’s someone using his pictures with the added “tattoos”.
Reposted by Leather boy Jackson Boyd 🔒
Reposted by Leather boy Jackson Boyd 🔒
Tightie whitie Sunday
December 28, 2025 at 10:48 PM
Tightie whitie Sunday
When we DM a kinkster we should start including names/titles we preferred to be called too. Mine would be:
Jackson Boyd (he/him) Son, boy, faggot, hole
In into (fill in the rest here)
Jackson Boyd (he/him) Son, boy, faggot, hole
In into (fill in the rest here)
December 28, 2025 at 10:48 PM
When we DM a kinkster we should start including names/titles we preferred to be called too. Mine would be:
Jackson Boyd (he/him) Son, boy, faggot, hole
In into (fill in the rest here)
Jackson Boyd (he/him) Son, boy, faggot, hole
In into (fill in the rest here)
Reposted by Leather boy Jackson Boyd 🔒
I blame @gilbertsnodgrass.bsky.social for dressing this way. 😤💙
December 9, 2025 at 10:50 PM
I blame @gilbertsnodgrass.bsky.social for dressing this way. 😤💙
Reposted by Leather boy Jackson Boyd 🔒
This is what happens to naughty boys like @jacksonboyd.bsky.social when they sneak around and find Santa late at night! @chibear20.bsky.social
#santakink #santaporn #gaybear
#santakink #santaporn #gaybear
December 24, 2025 at 11:52 AM
This is what happens to naughty boys like @jacksonboyd.bsky.social when they sneak around and find Santa late at night! @chibear20.bsky.social
#santakink #santaporn #gaybear
#santakink #santaporn #gaybear
Reposted by Leather boy Jackson Boyd 🔒
Morning my lovelies near and far
December 13, 2025 at 4:06 PM
Morning my lovelies near and far
Reposted by Leather boy Jackson Boyd 🔒
Can’t wait till the next Brief Encounters. So many hot men in tighty whities, I lost it 🤤
Thank you all for a great night!
Thank you all for a great night!
December 14, 2025 at 2:08 AM
Can’t wait till the next Brief Encounters. So many hot men in tighty whities, I lost it 🤤
Thank you all for a great night!
Thank you all for a great night!
Reposted by Leather boy Jackson Boyd 🔒
So excited to see everyone tonight at @jackhammerchicago.bsky.social for Brief Encounters: A Tighty Whities Night. Whether I’m your nerd dad, nerd bro, nerd son, or just a nerd you haven’t met yet, I’m excited to see so many butts and bulges in briefs!
December 11, 2025 at 2:33 PM
So excited to see everyone tonight at @jackhammerchicago.bsky.social for Brief Encounters: A Tighty Whities Night. Whether I’m your nerd dad, nerd bro, nerd son, or just a nerd you haven’t met yet, I’m excited to see so many butts and bulges in briefs!
Reposted by Leather boy Jackson Boyd 🔒
Don’t forget! Tonight at @jackhammerchicago.bsky.social it’s Brief Encounters: A Tighty Whities Night (no cover)!
So get those tighty whities ready! Whether that’s getting them extra tighty or maybe not so whitie 😈
So get those tighty whities ready! Whether that’s getting them extra tighty or maybe not so whitie 😈
December 11, 2025 at 4:40 PM
Don’t forget! Tonight at @jackhammerchicago.bsky.social it’s Brief Encounters: A Tighty Whities Night (no cover)!
So get those tighty whities ready! Whether that’s getting them extra tighty or maybe not so whitie 😈
So get those tighty whities ready! Whether that’s getting them extra tighty or maybe not so whitie 😈