Chicagoerwin
@chicagoerwin.bsky.social
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.
Reposted by Chicagoerwin
Reposted by Chicagoerwin
Between 7 and 8, definitely closer to 8.
We received a comment asking us to post the "Stages of Chastity" meme! I ( @lockedfist.bsky.social ) have no idea who originally made this or where I first saw it (maybe tumblr? like 10 years ago?).
Anyone know the original author?
Anyone know the original author?
October 12, 2025 at 3:33 PM
Between 7 and 8, definitely closer to 8.
All ya need is a bootlace and a good pain tolerance to give yourself a good time!
October 12, 2025 at 12:21 PM
All ya need is a bootlace and a good pain tolerance to give yourself a good time!
Cage needed a little air while heading to the gym…
October 11, 2025 at 1:40 PM
Cage needed a little air while heading to the gym…
Reposted by Chicagoerwin
My once powerful dick is now caged and useless in service to my Alpha Hadrian Temple. Thank you Sir for holding the key.
October 7, 2025 at 10:50 AM
My once powerful dick is now caged and useless in service to my Alpha Hadrian Temple. Thank you Sir for holding the key.
Reposted by Chicagoerwin
MATURE SLAVES
... can SERVE well into their SENIOR years!
... can SERVE well into their SENIOR years!
August 26, 2025 at 2:27 PM
MATURE SLAVES
... can SERVE well into their SENIOR years!
... can SERVE well into their SENIOR years!
Reposted by Chicagoerwin
Take the leap and do it: bow and kneel. It feels amazing once you do
August 22, 2025 at 1:26 PM
Take the leap and do it: bow and kneel. It feels amazing once you do
Reposted by Chicagoerwin
Born to serve
September 1, 2025 at 7:39 PM
Born to serve
Reposted by Chicagoerwin
Psychoanalytic theory views sex and money as closely tied, two dimensions of power; it's no surprise then that so many submissives crave to be financially controlled, dominated, exploited by Real Alpha Men.
#CashMaster
#CashMaster
September 11, 2025 at 8:15 PM
Psychoanalytic theory views sex and money as closely tied, two dimensions of power; it's no surprise then that so many submissives crave to be financially controlled, dominated, exploited by Real Alpha Men.
#CashMaster
#CashMaster
Reposted by Chicagoerwin
The label says it all… i am a bitch for my Alpha, Hadrian Temple. He is my Alpha and Omega, my everything.
September 14, 2025 at 12:04 AM
The label says it all… i am a bitch for my Alpha, Hadrian Temple. He is my Alpha and Omega, my everything.
Reposted by Chicagoerwin
If everyone adds a day, that’s a fair few years exposed…😈
exxxposeme.com/index.php?im... beg you all to click on link and extend a new round of public website exposure, each time you click the lasts extra 24 hours #gay #muscle #tinycock #exposure
September 13, 2025 at 8:50 PM
If everyone adds a day, that’s a fair few years exposed…😈
Caged for another week of confinement until it comes off again for a good cleaning! Happiness for this faggot is a freshly shaved crotch and a clean cage!
September 13, 2025 at 3:33 AM
Caged for another week of confinement until it comes off again for a good cleaning! Happiness for this faggot is a freshly shaved crotch and a clean cage!
This is what I looked like when I was pretending to be a Dominant Alpha male in Chicago 25 years ago…
Now i am just a proud faggot meant to grovel at real men’s feet and offer my body in service to glorify Alpha males and subjugate myself for humiliation.
Feels good to realize my truest self…
Now i am just a proud faggot meant to grovel at real men’s feet and offer my body in service to glorify Alpha males and subjugate myself for humiliation.
Feels good to realize my truest self…
September 12, 2025 at 11:56 PM
This is what I looked like when I was pretending to be a Dominant Alpha male in Chicago 25 years ago…
Now i am just a proud faggot meant to grovel at real men’s feet and offer my body in service to glorify Alpha males and subjugate myself for humiliation.
Feels good to realize my truest self…
Now i am just a proud faggot meant to grovel at real men’s feet and offer my body in service to glorify Alpha males and subjugate myself for humiliation.
Feels good to realize my truest self…
Served my Alpha and rewarded after 2 hours of cleaning his home by dry humping his boot while wearing my cage. Made a mess in the cage and still had to do a full day of errands before was able to clean up. Best day of errands ever!
September 11, 2025 at 3:18 AM
Served my Alpha and rewarded after 2 hours of cleaning his home by dry humping his boot while wearing my cage. Made a mess in the cage and still had to do a full day of errands before was able to clean up. Best day of errands ever!
I am a faggot. No need to apologize for it. I know what I am and no longer need to go and find myself. It is freeing to admit and accept my status in the community. No shame, no embarrassment just a proud faggot with nothing to prove to anyone else (except to the man a call Sir).
September 4, 2025 at 9:27 PM
I am a faggot. No need to apologize for it. I know what I am and no longer need to go and find myself. It is freeing to admit and accept my status in the community. No shame, no embarrassment just a proud faggot with nothing to prove to anyone else (except to the man a call Sir).
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
September 4, 2025 at 9:23 PM
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
September 4, 2025 at 9:21 PM
Reposted by Chicagoerwin
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
September 4, 2025 at 1:04 PM
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
September 4, 2025 at 1:04 PM
Trying to find a proper sized chastity cage. Purchased 4 already with varying success but not comfortable for 24/7 extended wear.
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Want to invest in high quality but hesitant to pay $200 for yet another short term cage.
Is there someplace that allows returns?
Grew into my leatherman identity as a Dominant top man, creating diverse scenes to keep the bottoms I engaged with coming back for more. Scenes were elaborate and I had the equipment to go from mild to wild in a very short order.
Then I met an Alpha male who showed me my truer more authentic self.
Then I met an Alpha male who showed me my truer more authentic self.
September 1, 2025 at 10:09 PM
Grew into my leatherman identity as a Dominant top man, creating diverse scenes to keep the bottoms I engaged with coming back for more. Scenes were elaborate and I had the equipment to go from mild to wild in a very short order.
Then I met an Alpha male who showed me my truer more authentic self.
Then I met an Alpha male who showed me my truer more authentic self.