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...
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 😈
Reposted by Leather boy Jackson Boyd 🔒
THURSDAY | 9PM–4AM
Brief Encounters: Tighty Whities Edition Whether you’re serving old-school Calvin Klein fantasy or rocking them your own way, this night’s all about the power of white briefs and the men who fill them.
It’s time to go classic... crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition Whether you’re serving old-school Calvin Klein fantasy or rocking them your own way, this night’s all about the power of white briefs and the men who fill them.
It’s time to go classic... crisp, clean, and barely there.
December 9, 2025 at 11:01 PM
THURSDAY | 9PM–4AM
Brief Encounters: Tighty Whities Edition Whether you’re serving old-school Calvin Klein fantasy or rocking them your own way, this night’s all about the power of white briefs and the men who fill them.
It’s time to go classic... crisp, clean, and barely there.
Brief Encounters: Tighty Whities Edition Whether you’re serving old-school Calvin Klein fantasy or rocking them your own way, this night’s all about the power of white briefs and the men who fill them.
It’s time to go classic... crisp, clean, and barely there.
Reposted by Leather boy Jackson Boyd 🔒
inspired by lovely handsome @jacksonboyd.bsky.social
love tighty whites
love tighty whites
December 10, 2025 at 2:59 PM
inspired by lovely handsome @jacksonboyd.bsky.social
love tighty whites
love tighty whites
Reposted by Leather boy Jackson Boyd 🔒
Happy hump day from the tighty whities crew. Who are we seeing tomorrow night?
@homemadebeef.bsky.social
@jacksonboyd.bsky.social
@homemadebeef.bsky.social
@jacksonboyd.bsky.social
December 10, 2025 at 3:41 PM
Happy hump day from the tighty whities crew. Who are we seeing tomorrow night?
@homemadebeef.bsky.social
@jacksonboyd.bsky.social
@homemadebeef.bsky.social
@jacksonboyd.bsky.social
Reposted by Leather boy Jackson Boyd 🔒
Who is dad seeing in their tighty whities on Thursday? Excited for the debut of Brief Encounters at @jackhammerchicago.bsky.social
See you in the @theholechicago.bsky.social?
Feat: @jacksonboyd.bsky.social & @pocketwolfspitz.bsky.social
See you in the @theholechicago.bsky.social?
Feat: @jacksonboyd.bsky.social & @pocketwolfspitz.bsky.social
December 10, 2025 at 12:29 AM
Who is dad seeing in their tighty whities on Thursday? Excited for the debut of Brief Encounters at @jackhammerchicago.bsky.social
See you in the @theholechicago.bsky.social?
Feat: @jacksonboyd.bsky.social & @pocketwolfspitz.bsky.social
See you in the @theholechicago.bsky.social?
Feat: @jacksonboyd.bsky.social & @pocketwolfspitz.bsky.social
Reposted by Leather boy Jackson Boyd 🔒
December 19, 2024 at 2:33 AM
Day 5 Vintage TWs. Sometimes my finds are interesting. What’s the story here? 1966 so I wonder the brand. Also that man is so hot
December 6, 2025 at 9:25 PM
Day 5 Vintage TWs. Sometimes my finds are interesting. What’s the story here? 1966 so I wonder the brand. Also that man is so hot
Reposted by Leather boy Jackson Boyd 🔒
Thursday 12/11 @ 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.
December 4, 2025 at 7:02 PM
Thursday 12/11 @ 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.
Part 4Vintage TW: would love the context. Reminded me of scouts. Bunch of us got pranked and covered in shaving cream and had to shower. We had a higher ratio of TWs than these photos I’ll say.
December 5, 2025 at 2:29 PM
Part 4Vintage TW: would love the context. Reminded me of scouts. Bunch of us got pranked and covered in shaving cream and had to shower. We had a higher ratio of TWs than these photos I’ll say.
Reposted by Leather boy Jackson Boyd 🔒
Taking Dads L O A D on top of the world 🌎
Any of our followers have an ATV⁉️
Subscribe to see this outdoor 1️⃣3️⃣ min on BOTH platforms ⬇️
🎥👀 justfor.fans/CannaCruisers
✊🏻💦 onlyfans.com/reddandsonn
#beefyguys #muscledad #gingerdaddy #exhibitionism #dadandson #alphadaddy #gingerdad #outdoorsex #alpha
Any of our followers have an ATV⁉️
Subscribe to see this outdoor 1️⃣3️⃣ min on BOTH platforms ⬇️
🎥👀 justfor.fans/CannaCruisers
✊🏻💦 onlyfans.com/reddandsonn
#beefyguys #muscledad #gingerdaddy #exhibitionism #dadandson #alphadaddy #gingerdad #outdoorsex #alpha
March 11, 2025 at 11:09 AM
Taking Dads L O A D on top of the world 🌎
Any of our followers have an ATV⁉️
Subscribe to see this outdoor 1️⃣3️⃣ min on BOTH platforms ⬇️
🎥👀 justfor.fans/CannaCruisers
✊🏻💦 onlyfans.com/reddandsonn
#beefyguys #muscledad #gingerdaddy #exhibitionism #dadandson #alphadaddy #gingerdad #outdoorsex #alpha
Any of our followers have an ATV⁉️
Subscribe to see this outdoor 1️⃣3️⃣ min on BOTH platforms ⬇️
🎥👀 justfor.fans/CannaCruisers
✊🏻💦 onlyfans.com/reddandsonn
#beefyguys #muscledad #gingerdaddy #exhibitionism #dadandson #alphadaddy #gingerdad #outdoorsex #alpha
Part 3 of vintage tighty whities stuff I have. A 1946 print ad of Brooklyn Dodgers pitcher Ralph Branca. I might be a bottom, but I’m definitely an ass guy especially in full cut briefs. I should probably frame this right?
December 4, 2025 at 3:25 AM
Part 3 of vintage tighty whities stuff I have. A 1946 print ad of Brooklyn Dodgers pitcher Ralph Branca. I might be a bottom, but I’m definitely an ass guy especially in full cut briefs. I should probably frame this right?
Reposted by Leather boy Jackson Boyd 🔒
Dad fucking me good, hard and raw in the yard.
w/ @gingerdaddy74.bsky.social
w/ @gingerdaddy74.bsky.social
November 5, 2025 at 1:39 AM
Dad fucking me good, hard and raw in the yard.
w/ @gingerdaddy74.bsky.social
w/ @gingerdaddy74.bsky.social
Part 2 of vintage tighty whities stuff. A sexy pose is great but there is something else about candid pics. Maybe it’s the realism. Bought this on eBay funny enough.
December 3, 2025 at 12:26 AM
Part 2 of vintage tighty whities stuff. A sexy pose is great but there is something else about candid pics. Maybe it’s the realism. Bought this on eBay funny enough.
Part 1 of my vintage tighty whities media collection. An old magazine ad from 1983 of a stud in some BVDs. This kinda stuff was pure sex to me as I was discovering my sexuality and fetish.
December 2, 2025 at 2:57 AM
Part 1 of my vintage tighty whities media collection. An old magazine ad from 1983 of a stud in some BVDs. This kinda stuff was pure sex to me as I was discovering my sexuality and fetish.
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 🔒
