LeatherboyKai
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leatherboykai.bsky.social
LeatherboyKai
@leatherboykai.bsky.social
380 followers 290 following 150 posts
Trans leatherboy in Chicago | Suits, haircuts and muscle worship | CHC member | switch with hands made for play
Posts Replies Media Videos
leatherboykai.bsky.social
Victor the vulva and I are just about ready to give our vaginal play 101 class at Twin Cities Leather & Fetish Weekend!
November 8, 2025 at 7:09 PM
Reposted by LeatherboyKai
dukerough.bsky.social
The one thing that gets me to the gym is being able to workout naked, @leatherboykai.bsky.social being a dork is just icing on the cake. #NakedFriends #PigletAdventures
November 4, 2025 at 12:13 PM
Reposted by LeatherboyKai
pupvidhra.bsky.social
I promised Sir @leatherboykai.bsky.social I would post this adorable as fuck picture of us, me in his ascot and him in his barber cape *wags*
November 3, 2025 at 9:33 PM
leatherboykai.bsky.social
Today’s a rest day from the gym so naturally I’m thinking about the last time I was lifting.
November 1, 2025 at 6:18 PM
Reposted by LeatherboyKai
yournewdadxxx.bsky.social
I shower a couple times a day, everyday. But on Saturday mornings, I video them to track my body’s progress.

Also: some of you apparently enjoy watching reasonably fit middle aged men wash their asses. Win-win.

Full video: justfor.fans/yournewdadxxx
November 1, 2025 at 10:33 AM
leatherboykai.bsky.social
Definitely need a relaxing video game night in for the evening. Playing Legends ZA!
October 31, 2025 at 9:41 PM
Reposted by LeatherboyKai
pupvidhra.bsky.social
Unf 🥵
spacepupsilver.com Silver 😵‍💫🐶🧠✨ @spacepupsilver.com · Sep 8
You want to try being Arcanine so badly you ask your psychic pokemon to switch your minds... you didn't quite think about how Arcanine felt about this though.
subscribestar.adult/spacepupsilver
A 6 panel comic showing a trainer and an arcanine swapping minds. Panel 1. a trainer in a baseball cap is shown excitedly stood next to an arcanine with a kadabra standing the background. The trainer says: Hey Kadabra! Use your psychic powers to swap me and arcanine's brain, I want to know what it's like to be a big fire dog! Panel 2. Kadabra looks bored but lifts it's spoon and says: Kadabra. Panel 3. The image shows the brains of the trainer and the arcanine lifted up. Panel 4. The brains have been shown to be exchanged, a much smaller brain now in the trainers skull whilst the arcanine has a large brain floating above it to suggest the minds have been swapped. The arcanine, now a human, looks at it's new hands with excitement. The human, now a dog, looks at it's paws with happiness. Panel 5. The arcanine in the trainers body has a huge grin and says: Hey kadabra! Use your psychic powers to make 'arcanine' forget he was ever human. The kadabra opens it's eyes wide to continue it's psychic powers. Panel 6. The arcanine is looking dumb as it can't remember anything. The trainer lifts a pokeball up and says: Arcanine, return.
September 8, 2025 at 8:20 PM
Reposted by LeatherboyKai
bionicslingshot.bsky.social
If anyone asks why I’m so tired tomorrow, I’ll just tell them it’s because of baseball and definitely not because I was playing video games and using various sheet masks and serums until 2:00 AM.
October 28, 2025 at 6:05 AM
Reposted by LeatherboyKai
lefaun.bsky.social
Locktoberfest Chili is now a thing!

A friend and I submitted a beer, brat, and sauerkraut chili to a competition, winning second place!

(Yes, I sewed a zipper into the lederhosen for the singular purpose of showing the chastity belt during the competition). #StayLocked
October 27, 2025 at 1:57 PM
leatherboykai.bsky.social
Nothing like a good pup massage after a long day. @pupvidhra.bsky.social always knows what will make Sir feel better. 🥰
October 27, 2025 at 3:24 AM
leatherboykai.bsky.social
Answer in gifs.
October 25, 2025 at 7:27 PM
Reposted by LeatherboyKai
slimsuit.bsky.social
23days locked, starting locktober with a pink tie. Excepting I’ll success my first locktober, I hope in formal attire the more as possible 🔐👔

#locktober #lockedboy #teamlocked #suitfetish #suitedboy
October 1, 2025 at 2:25 PM
leatherboykai.bsky.social
What’s it like inside your head?
October 23, 2025 at 7:54 PM
Reposted by LeatherboyKai
leatherboykai.bsky.social
Donald Duck in Modern Inventions (1937). He tries to scam a robotic barber chair & it forces him to get a haircut. He falls and winds up having his lower half caped, cut & combed. 🥵
October 22, 2025 at 5:51 PM
Reposted by LeatherboyKai
pupvidhra.bsky.social
MOAR JOURNEYS! This time it's taking photos for Sir in the barber's cape. Of course Sir also chooses the haircut 💈
Photo before the haircut in the barber's cape Photo requested by Sir of me in the cap mid cut. That hot towel felt AMAZING 🤩
October 18, 2025 at 11:54 PM
leatherboykai.bsky.social
Such a pretty puppy.
October 20, 2025 at 1:18 AM
leatherboykai.bsky.social
We’re getting things underway at @mirubber.bsky.social! <3
October 17, 2025 at 5:33 PM
Reposted by LeatherboyKai
frankr0d.bsky.social
Barbershop Play 5
@heathenhalo.bsky.social
@markusstonexx.bsky.social
@menatplaycom.bsky.social
October 16, 2025 at 10:11 PM
leatherboykai.bsky.social
Ready for MIR!
October 16, 2025 at 8:44 PM
Reposted by LeatherboyKai
seamusoreilly69.bsky.social
Sooo day 5 never posted 🥲
Day 5: Domestic Servitude. “Put a toy up your ass and clean your house wearing only a collar”

Submission can be found in the most mundane tasks, but that doesn’t mean you can’t spice them up a little 😉#KinktTober

Mantra: Today i serve in any way i am able.
October 6, 2025 at 9:48 PM
Reposted by LeatherboyKai
douglasdegenaars.bsky.social
Clothed. Commanding.
Naked. Obeying.

The Naked Men and the Clothed Men Who Enjoy Them Book Series
📖 douglasdegenaars.com

#CMNM #DomSub #GayErotica #ExposureKink
October 5, 2025 at 1:16 PM
Reposted by LeatherboyKai
fabledfaun.bsky.social
T-shot day has been made extra horny thanks to @spacepupsilver.com 😵‍💫
Two panel comic. First panel shows nude chaste himbo doctor in a lab coat holding two blue syringes labeled “boy juice (boy flavor)” towering over a puppy boy on their knees. The pup wears a green hood, green trans tape, green tail plug and a black tattoo saying “MUTT” across its back. The doctor says “alright mutt, it’s time for your monthly shots!”. Second panel shows himbo doctor showing his butt to the now swol pup. Doctor says “now could you help me with my daily shot?”. Swol pup is still knelt down but now with two blue syringes sticking from their butt. Pup’s face is foaming at the mouth with desire. “Horny noise” says the pup.
October 9, 2025 at 1:44 PM
leatherboykai.bsky.social
I love a nice headshave 🥵
seamusoreilly69.bsky.social Seamus O’Reilly @seamusoreilly69.bsky.social · Oct 1
Day 1: Head Shaving. “Record and post a full, wet, razor #headshave. 🪒🪒🪒”
i chose to start with this one to get me in the right mindset and prepare for my month of submission and fetish. #KinkTober
Mantra: Today i prepare my body for servitude.
October 8, 2025 at 11:50 PM
leatherboykai.bsky.social
Thoughts @pupvidhra.bsky.social ?
spacepupsilver.com Silver 😵‍💫🐶🧠✨ @spacepupsilver.com · Oct 6
To be a 'Sex dog™' you need to have all the matching accessories and the 'Sex Dog™ Dream Dungeon'.
subscribestar.adult/spacepupsilver
A two panel erotic comic showing a muscular man in leather pants, the handler, and on his knees in front of him with a big dick is a man in a rubber latex suit wearing a puppy mask. Panel 1. The handler is holding a clipboard and says: Alright... Dog hood, Dog Suit, dog collar, dog harness, dog tail, dog kneepads. What Am I missing...? The dog looks up with a huge smile, happy for the attention. Floating next to his head is the symbol from the video game "The Sims" that shows friendship is increasing. Panel 2. The handler is beaming, he is so happy, he realised what was missing, he exclaims: Dog chastity cage! The dogs dick is now in a chastity cage and the dog looks very unhappy about it. The symbol for friendship has now tripled and all three of them show negative friendship.
October 6, 2025 at 6:00 PM
leatherboykai.bsky.social
Hey @pupvidhra.bsky.social you may need to sit down for this…..it’s just too cute.
spacepupsilver.com Silver 😵‍💫🐶🧠✨ @spacepupsilver.com · Oct 3
Oh no! The Pokémon broke free!
Shoot! It was so close too!
-
I think it's @tstoater.bsky.social in there...
October 4, 2025 at 5:12 PM