Leather boy Jackson Boyd πŸ”’'s Avatar

Leather boy Jackson Boyd πŸ”’

@jacksonboyd.bsky.social

He/Him -Chicago -Bears, tighty whities, leather, cigars, chastity -Boy to Cliff Boyd https://bsky.app/profile/chibear20.bsky.social -πŸ’™Property of my DadπŸ”’ ➑️Smokeout BLUF#5641 RECON: leatherboyjackson https://linktr.ee/chicagotwcub BLM, πŸ³οΈβ€βš§οΈ, πŸ‡΅πŸ‡Έ, πŸ‡ΊπŸ‡¦

11,157 Followers  |  3,304 Following  |  1,498 Posts  |  Joined: 07.07.2023  |  2.1105

Latest posts by jacksonboyd.bsky.social on Bluesky

Fucking hell πŸ₯΅

29.01.2026 01:21 β€” πŸ‘ 1    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

The way that even if I was a millionaire I’d still only wear basic tighty-whities.

28.01.2026 20:04 β€” πŸ‘ 42    πŸ” 2    πŸ’¬ 0    πŸ“Œ 0

I really hope to have this POV one day irl

27.01.2026 22:57 β€” πŸ‘ 4    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
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Sadly no but I did get a tattoo OF tighty-whities. Shorts were on but waistband was very much out

27.01.2026 21:45 β€” πŸ‘ 7    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
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Yup. Did exactly the same on FB

27.01.2026 21:40 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

Wow! Can’t lie, at one point this was almost my first tattoo

27.01.2026 21:34 β€” πŸ‘ 1    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

Nice angels and demons tattoo

27.01.2026 20:34 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

Can confirm. Very good top.

27.01.2026 20:29 β€” πŸ‘ 7    πŸ” 0    πŸ’¬ 2    πŸ“Œ 0

Fucking hell 🀀

26.01.2026 22:48 β€” πŸ‘ 1    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

You look great! Love this waistband

26.01.2026 22:06 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

Exactly. To feel vulnerable but safe

26.01.2026 17:07 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 2    πŸ“Œ 0

Nah you should. It’s my favorite piercing

26.01.2026 17:06 β€” πŸ‘ 0    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

Not sure if other feel any similar ways but, topping for me is/was 85% physical and 15% mental whereas bottoming is 60% mental and 40% physical sensation. Because bottoming for me is a space I feel vulnerable and not in control. It’s a headspace thing

26.01.2026 16:40 β€” πŸ‘ 31    πŸ” 0    πŸ’¬ 2    πŸ“Œ 0
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Having a PA means straight guys looking at your dick in the locker room or urinal

26.01.2026 14:42 β€” πŸ‘ 267    πŸ” 15    πŸ’¬ 14    πŸ“Œ 0

Dumb on them to kink shame. Not everything is made for β€œyou” so what’s hard about letting people like what they like? Glad to see more people join the chastity community

23.01.2026 18:04 β€” πŸ‘ 7    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0
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Does my hole come off as β€˜welcoming’?

22.01.2026 13:21 β€” πŸ‘ 232    πŸ” 9    πŸ’¬ 7    πŸ“Œ 0

Woof

22.01.2026 02:05 β€” πŸ‘ 0    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
A photo taken from between my legs as I sit in a desk chair, wearing a black t-shirt and blue and white plaid boxers. My erect cock and fat balls are pulled through the fly of the boxers, the heavy steel PA ring glinting at the tip of my erection.

A photo taken from between my legs as I sit in a desk chair, wearing a black t-shirt and blue and white plaid boxers. My erect cock and fat balls are pulled through the fly of the boxers, the heavy steel PA ring glinting at the tip of my erection.

Here ya go 😈

22.01.2026 02:03 β€” πŸ‘ 200    πŸ” 16    πŸ’¬ 3    πŸ“Œ 0
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A special friend took some nice pics of me at MAL (after dropping a load in me)

21.01.2026 16:33 β€” πŸ‘ 260    πŸ” 17    πŸ’¬ 7    πŸ“Œ 0
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Hump day β˜•. Make it a great one.

21.01.2026 13:03 β€” πŸ‘ 233    πŸ” 19    πŸ’¬ 4    πŸ“Œ 1
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Was making an outfit video for TikTok, but thought Bluesky would appreciate a little #twt angle to it hehehe

21.01.2026 07:55 β€” πŸ‘ 114    πŸ” 8    πŸ’¬ 3    πŸ“Œ 0

It’s like nasty pig clothes. Is it basic? Yeah. Is it also the only gay clothing brand that makes plus size clothing? Also yeah. Bears are limited on options

21.01.2026 04:21 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

Fucking hot af

19.01.2026 20:33 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0
Me in just white briefs from the front while standing.

Me in just white briefs from the front while standing.

Me in just white briefs from the back while standing.

Me in just white briefs from the back while standing.

Me in just white briefs from the front while bent over showing my butt.

Me in just white briefs from the front while bent over showing my butt.

I now have proper briefs for my next spanking. Thank you, @jacksonboyd.bsky.social, for the recommendation to select the Fruits. Classic selection.

19.01.2026 20:30 β€” πŸ‘ 211    πŸ” 16    πŸ’¬ 6    πŸ“Œ 0

I’m at MAL too… πŸ˜‰

17.01.2026 00:17 β€” πŸ‘ 0    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

Yes

17.01.2026 00:15 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0
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Before and after. (Spanking)

16.01.2026 23:45 β€” πŸ‘ 164    πŸ” 9    πŸ’¬ 10    πŸ“Œ 2

Reskeet if you’re a bator and want other bators to add you πŸ€™

16.11.2024 21:30 β€” πŸ‘ 260    πŸ” 23    πŸ’¬ 5    πŸ“Œ 2

A new blank canvas. Don’t be afraid to show to off on here πŸ˜‰

15.01.2026 23:51 β€” πŸ‘ 1    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

Yes fruits are my go to and jockey in second. I’d say fruits or hanes would be good choices for spanking. Affordable which makes it ok to rip open.

15.01.2026 21:58 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0

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