LeatherboyKai
@leatherboykai.bsky.social
Trans leatherboy in Chicago | Suits, haircuts and muscle worship | CHC member | switch with hands made for play
Pinned
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.
Reposted by LeatherboyKai
You'll be happier as a mindless statue/mannequin, I promise 😜
#erotic #hypnosis #statuetf #mannequintf
#erotic #hypnosis #statuetf #mannequintf
December 12, 2025 at 6:50 AM
You'll be happier as a mindless statue/mannequin, I promise 😜
#erotic #hypnosis #statuetf #mannequintf
#erotic #hypnosis #statuetf #mannequintf
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.
January 10, 2026 at 4:28 AM
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.
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.
January 7, 2026 at 5:38 PM
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.
Reposted by LeatherboyKai
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.
📸 @gimp-vulcan.bsky.social
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.
📸 @gimp-vulcan.bsky.social
April 7, 2025 at 3:09 PM
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.
📸 @gimp-vulcan.bsky.social
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.
📸 @gimp-vulcan.bsky.social
Happy seeing some great results at the gym.
December 7, 2025 at 11:44 PM
Happy seeing some great results at the gym.
Reposted by LeatherboyKai
Sebastian Coxxx. Appearing in "A close shave"....
December 1, 2025 at 11:36 AM
Sebastian Coxxx. Appearing in "A close shave"....
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?
November 18, 2025 at 6:47 PM
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?
Had a great workout today. Now to head to the office <3
November 17, 2025 at 3:48 PM
Had a great workout today. Now to head to the office <3
Reposted by LeatherboyKai
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
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
October 15, 2025 at 5:46 PM
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
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
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
Victor the vulva and I are just about ready to give our vaginal play 101 class at Twin Cities Leather & Fetish Weekend!
Reposted by LeatherboyKai
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
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
Reposted by LeatherboyKai
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
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*
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
Today’s a rest day from the gym so naturally I’m thinking about the last time I was lifting.
Reposted by LeatherboyKai
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
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
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
Also: some of you apparently enjoy watching reasonably fit middle aged men wash their asses. Win-win.
Full video: justfor.fans/yournewdadxxx
Definitely need a relaxing video game night in for the evening. Playing Legends ZA!
October 31, 2025 at 9:41 PM
Definitely need a relaxing video game night in for the evening. Playing Legends ZA!
Reposted by LeatherboyKai
Unf 🥵
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
subscribestar.adult/spacepupsilver
September 8, 2025 at 8:20 PM
Unf 🥵
Reposted by LeatherboyKai
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
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.
Reposted by LeatherboyKai
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
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
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
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
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
Nothing like a good pup massage after a long day. @pupvidhra.bsky.social always knows what will make Sir feel better. 🥰
Answer in gifs.
October 25, 2025 at 7:27 PM
Answer in gifs.
Reposted by LeatherboyKai
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
#locktober #lockedboy #teamlocked #suitfetish #suitedboy
October 1, 2025 at 2:25 PM
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
#locktober #lockedboy #teamlocked #suitfetish #suitedboy
What’s it like inside your head?
October 23, 2025 at 7:54 PM
What’s it like inside your head?
Reposted by LeatherboyKai
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
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. 🥵
Reposted by LeatherboyKai
MOAR JOURNEYS! This time it's taking photos for Sir in the barber's cape. Of course Sir also chooses the haircut 💈
October 18, 2025 at 11:54 PM
MOAR JOURNEYS! This time it's taking photos for Sir in the barber's cape. Of course Sir also chooses the haircut 💈