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, 🏳️⚧️, 🇵🇸, 🇺🇦
Before and after. (Spanking)
January 16, 2026 at 11:45 PM
Before and after. (Spanking)
MAL bound (later today)
January 15, 2026 at 5:19 PM
MAL bound (later today)
You in High School vs you now…
January 14, 2026 at 7:46 PM
You in High School vs you now…
What do you sleep in? #tightywhities
January 13, 2026 at 5:13 AM
What do you sleep in? #tightywhities
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”.
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
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.
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?
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.
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.
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?
@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
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
19 as well
October 31, 2025 at 12:18 PM
19 as well