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LeatherboyKai

@leatherboykai

Trans leatherboy in Chicago | Suits, haircuts and muscle worship | CHC member | switch with hands made for play

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22.09.2023
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Latest posts by LeatherboyKai @leatherboykai

Wooden paddles and leather straps. Text: [There is no objective data indicating how humans should behave sexually because this is a philosophical question.]

Wooden paddles and leather straps. Text: [There is no objective data indicating how humans should behave sexually because this is a philosophical question.]

Quote from When Is Sex Abnormal? by Paul J. Gillette in Sexology (March 1971). Photo from the LA&M mail order catalogs collection.

10.03.2026 21:29 πŸ‘ 34 πŸ” 11 πŸ’¬ 0 πŸ“Œ 1

Waiting between leg curl sets makes me feel like I'm sitting in a high chair waiting for dinner.

06.03.2026 02:39 πŸ‘ 42 πŸ” 1 πŸ’¬ 3 πŸ“Œ 0
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After 25 minutes in the kneeling frame, I gave Pup Skip @baddoguk.bsky.social a lie down. I left him hooded & didn't explain the rules of this game but he was a fast learner.

For you the rules were: keep your feet & legs up to avoid electric shock to the glutes. It's an abs and legs training game!

04.03.2026 16:11 πŸ‘ 198 πŸ” 23 πŸ’¬ 4 πŸ“Œ 4
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Back at it again! Feeling swole and happy.

16.02.2026 01:01 πŸ‘ 17 πŸ” 1 πŸ’¬ 0 πŸ“Œ 0

Thank you!!! Every day is a chance to grow!

13.02.2026 15:00 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
A 3 panel erotic comic of a man being brainwashed into a butler.
Panel 1. A young man with a tshirt that says brat on it is pointing and smiling. "So you know how to hypnotise people? Make me into a sex slave! Deck me out in rubber and have me as ap ortable fuck toy. How absolutely awful for me would that be, right?"/
Panel 2. The man hears a couple of finger snaps, he looks down and is suddenly naked, he covers his crotch with his hand. "Hey! Where did my clothes go!? I don't want to be a naked slave! I want to be a rubber one!".
Panel 3. The man is now dressed as a butler holding a silver tray, spirals in his eyes. "Mater, I have finished making the canapΓ©s. Is there anything else you would like assistance with?".

A 3 panel erotic comic of a man being brainwashed into a butler. Panel 1. A young man with a tshirt that says brat on it is pointing and smiling. "So you know how to hypnotise people? Make me into a sex slave! Deck me out in rubber and have me as ap ortable fuck toy. How absolutely awful for me would that be, right?"/ Panel 2. The man hears a couple of finger snaps, he looks down and is suddenly naked, he covers his crotch with his hand. "Hey! Where did my clothes go!? I don't want to be a naked slave! I want to be a rubber one!". Panel 3. The man is now dressed as a butler holding a silver tray, spirals in his eyes. "Mater, I have finished making the canapΓ©s. Is there anything else you would like assistance with?".

Your version of being a slave: Decked out in rubber being fucked silly all day long.
Their version of you being a slave: Doing ALL the household chores whilst dressed up as a prim and proper butler boy.
subscribestar.adult/spacepupsilver

13.02.2026 08:50 πŸ‘ 259 πŸ” 31 πŸ’¬ 2 πŸ“Œ 3
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13.02.2026 14:08 πŸ‘ 62 πŸ” 7 πŸ’¬ 0 πŸ“Œ 0
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Himboification: Would you trade away your brain and cock to have a perfect body, a tiny nub, and simple-minded happiness?

24.01.2026 04:20 πŸ‘ 142 πŸ” 17 πŸ’¬ 5 πŸ“Œ 0
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Haircuts as always but fussing with a guys hair to get a tall pompadour

07.02.2026 14:36 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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….good job puppy

25.01.2026 20:08 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I love the guys pomp! So sexy

19.01.2026 06:28 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Good dog!

15.01.2026 00:02 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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You'll be happier as a mindless statue/mannequin, I promise 😜
#erotic #hypnosis #statuetf #mannequintf

12.12.2025 06:50 πŸ‘ 46 πŸ” 7 πŸ’¬ 0 πŸ“Œ 0

πŸ‘€

10.01.2026 21:46 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Does this help? :D

10.01.2026 17:18 πŸ‘ 4 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Thanks! It was named by a brother at camp!

10.01.2026 17:18 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Had a fun scene with my boy @jlink0222.bsky.social who gave me some insane height on my hair by putting it in rollers. Definitely was fun. Can’t wait to see what other fun he has in store for my hair.

10.01.2026 04:27 πŸ‘ 7 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Back in Chicago. Invited my pup @pupvidhra.bsky.social over for cuddles and some TV time, then decided his hair needed a little attention too. Rollers in for extra height, a very clingy pup insisting on being part of the process. Honestly, the best way to get ready.

07.01.2026 17:38 πŸ‘ 16 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Duck paws lovers, where you at? πŸ¦†πŸΎ
Silicone, squishy, and ready to turn you into a duck.

#New #Duck #Paws #Silicone #Transformation #AD #fetish #Kink #Gpawz

29.12.2025 08:13 πŸ‘ 457 πŸ” 81 πŸ’¬ 24 πŸ“Œ 36
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Talk about a new level of helplessness.
As the zip ties slowly get tighter, you know there is no going back. Add the belts for extra snugness and security.
There was no fast way to be let out. I knew I was a stuck bondage toy.
πŸ“Έ @gimp-vulcan.bsky.social

07.04.2025 15:09 πŸ‘ 464 πŸ” 58 πŸ’¬ 8 πŸ“Œ 3

Thank you, I’ve been feeling better and better when I consistently workout. The physical benefits are also very nice.

11.12.2025 00:50 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Happy seeing some great results at the gym.

07.12.2025 23:44 πŸ‘ 108 πŸ” 2 πŸ’¬ 5 πŸ“Œ 0

That’s a lot of hard work!

06.12.2025 18:44 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Sebastian Coxxx. Appearing in "A close shave"....

01.12.2025 11:36 πŸ‘ 317 πŸ” 88 πŸ’¬ 3 πŸ“Œ 3
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Single arm cable rows!

18.11.2025 18:59 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Finished a heavy back and shoulder day at the gym with some calf work thrown in. My pump is preventing me from properly showering. Anyone up for helping me reach my back?

18.11.2025 18:47 πŸ‘ 105 πŸ” 3 πŸ’¬ 4 πŸ“Œ 0
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a cartoon duck is hanging upside down on a beach . ALT: a cartoon duck is hanging upside down on a beach .

Awe thank you

17.11.2025 22:29 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Had a great workout today. Now to head to the office <3

17.11.2025 15:48 πŸ‘ 46 πŸ” 0 πŸ’¬ 2 πŸ“Œ 0
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Is Deaf Pup Culture real?

Yes. But finding community is hard. I worry it could disappear. I'm creating content to build a bridge for disabled pups and keep our culture alive. Your shares help! 🐺🀟

#pups #pupplay #deaf #deaffurry #asl #pupplaycommunity #disability

15.10.2025 17:46 πŸ‘ 1263 πŸ” 513 πŸ’¬ 36 πŸ“Œ 20

Looking fantastic!

09.11.2025 03:25 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0