Charliebear • 1945 - 2019

I am saddened and relieved that My devoted slave Charliebear has passed onto the Other Side. His struggle with lung cancer was mounting but he never let it get in the way of his life. We’ve had many adventures together in person and remotely, with extended house-bound bondage being the majority of our play. He owned quite a collection of shackles and toys and would keep the keys frozen in block of ice to deter escape. Not that he ever wanted to escape. Charliebear was also my record chastity slave, with an impossibly long lock-up of over 600 days being chaste. His favorites were always bondage and chastity. His fascination with chastity drew him to hypnosis and to making these memes with captions he’d found on on other photos.


Before we became acquainted, Charliebear was known to others as Master Charles. He was a community organizer in the NYC BDSM scene and created the very first BBS (Bulletin Board System - essentially a community forum not unlike Max Fisch) for kinksters, called The English Palace. With the internet being in its infancy, people found their way to this bulletin board and were able to share their divergent sexual interests amongst others who were also alike. He facilitated a sense of belonging and community for people who were into kink and BDSM.


The biggest gift that Charliebear gave to Me in a session was allowing Me to perform minor surgury on the carbuncles/cysts on his back. He completely trusted me to roleplay Dr. PimplePopper to my heart’s desire and even film it!!

A slave’s devotion commonly hinges on their abilities and self-perceptions of how capable they are. It is up to the Dominant to mold the slave - to bring up the standard and to effectively mold the slave into one of the highest incarnation. I was never able to mold Charliebear much more than his waistline. His devotion was complete from the beginning, albeit stubborn at certain times. He wasn’t one for spiritual mumbo-jumbo but still respected that his Owner was. At My direction, he meditated. He would be released to do tantric self-pleasure with or without orgasm. He would read the spiritual self-help books I assigned to him. None of these seemed to have much an effect. It wasn’t about transformation with Charliebear, it was about using his will to prove his devotion to Me, which he made very clear.


It took Me a while to understand chastity play. The very idea went against every understanding I had about the men I thought I knew and sought to serve as a service top. When Charliebear first came to Me at the FF Dungeon, I was baffled. “Why would anyone want their cock locked up?!” was My thought for a very long time. But slowly and over time, and with the help of the chastity memes that Charliebear made, I came to understand it was about control. As was bondage, because it was essentially a form of bondage. Charlibear helped Me to deepen My understanding of power exchange through his desire to be controlled in these very specific ways.


On his deathbed is where we had our last emotional exchange. There was a part of Me that was still frustrated about his inability to implement a lifestyle change that would’ve helped his health, but being helpless always frustrates Me. I had to let that go and say goodbye. We spoke over FaceTime every few days until the opiates and lack of oxygen took away his cognitive abilities. On Sunday, May 5, Charliebear left this dimension. His son called Me and let Me know, and we had a kind-hearted exchange on the phone. I am so grateful for having a slave like Charliebear to teach Me so many things, and look forward to seeing him in the afterlife.