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Chicagoerwin

@chicagoerwin

Leatherman with old school training and adherence to leatherman protocol. Currently caged and in servitude to a Dominant Alpha Male. Vivid and lurid fantasies often result in a hands-free ejaculation.

35
Followers
45
Following
68
Posts
27.05.2025
Joined
Posts Following

Latest posts by Chicagoerwin @chicagoerwin

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Portrait of a submissive…

03.03.2026 17:18 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Those lucky briefs Sir!!!

27.02.2026 21:42 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

You wear leather well Sir and it certainly does NOT wear you.

25.02.2026 19:49 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Your arms could hurt someone!

16.02.2026 02:47 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I serve only you Sir. Thank you for taking this faggot and showing him the meaning of service!

13.02.2026 20:40 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I serve only you Sir. Thank you for showing your faggot boy his true self!

13.02.2026 20:37 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Yes.

10.02.2026 20:39 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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After a big surgery it feels good to be labeled as property, caged and wearing slutty underwear to honor my Dominant Sir Hadrian Temple!

10.02.2026 15:24 πŸ‘ 4 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Lucky briefs!

01.02.2026 15:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Lucky briefs!

01.02.2026 15:59 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Repost if you are a proud one.

24.11.2024 15:20 πŸ‘ 229 πŸ” 74 πŸ’¬ 4 πŸ“Œ 6

Being bald for many years I don’t even know how much a haircut costs! Whatever it costs it makes you look good Sir!

18.01.2026 19:28 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Very interesting and helped me understand the concern a good sadist uses during play.

11.01.2026 13:08 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Show my cage off as well…

06.01.2026 03:49 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I’d treat your body like a temple and worship every inch until I’m free from sin!

05.01.2026 18:30 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

You inspire me…

05.01.2026 00:58 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Like the tee shirt Sir

31.12.2025 13:24 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Would live to be on the floor before you and look into your face Sir.

31.12.2025 00:16 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

I would happily come over and work those muscles Sir. I actually do give a great massage and stretching as well.

31.12.2025 00:13 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

What would you hang from your faggots balls Sir?

30.12.2025 16:48 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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1 link, 2 links, 3 links, MORE!!!

30.12.2025 16:27 πŸ‘ 5 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Beautiful!

30.12.2025 11:33 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Your faggot has never backed away from a challenge… especially in service on you Sir!

29.12.2025 04:22 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I need that pouch crammed in my mouth as a gag when I do my chores next Sir!

29.12.2025 04:20 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

If that happens again Sir think of giving your faggot a hard beating and you should find that energy pretty quick!

29.12.2025 04:19 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Or soak them in piss while I watch and when saturated with golden nectar take the briefs off and pull the waistband over my head and I’ll wear the briefs as a piss hood/collar!

25.12.2025 22:30 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

A faggot ALWAYS makes good on his promises Sir. Well at least this faggot does! Just need a time and a place, your crotch, those blue sport briefs and you to have copious amounts of tea before we meet.

25.12.2025 22:25 πŸ‘ 3 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

I could suck the piss right outta that blue fabric stretching over your crotch Sir!

25.12.2025 22:13 πŸ‘ 3 πŸ” 0 πŸ’¬ 2 πŸ“Œ 0
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Let's see who you're........Rt

03.10.2025 16:34 πŸ‘ 114 πŸ” 54 πŸ’¬ 4 πŸ“Œ 4

You’re enough of a present to make me believe in Santa Claus all over again Sir!

25.12.2025 21:57 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0