Hello everyone,
I’m keeping a small journal of my chastity journey. I hope you enjoy reading it.
My initial reason for coming to CM was that I believed chastity would help me curb my masturbation and porn habits. It felt like the right place to figure out how to introduce this lifestyle to my wife as my Key Holder (KH). Before, I knew very little about chastity beyond seeing it in porn—often worn by sissies and cuckolds (which reflects some of my interests:0)—but as I dove deeper, I realized it’s not just a physical device but also an emotional experience.
I ordered an inexpensive Chinese cage (my pink one) and waited patiently. During the wait, I made several blunt comments on @MistressS’s photos. She corrected my mistakes and adjusted my attitude, explaining more about FLR, chastity, and what it truly means. When I mentioned my wife and my goal of having her become my KH, she offered suggestions that seemed helpful. Unfortunately, despite our many conversations regarding both our needs, my wife isn’t very interested.
Even before the cage arrived, frustration grew as discussions with MistressS helped me discover more about myself. After some pleading on my behalf, MistressS agreed to help me learn further and stepped in as my KH until I could persuade my wife to take up that role. Almost immediately, she began directing my behavior and questioning what I liked, quickly identifying me as a closet sissy (which surprised me). I accepted her commands and instructions.
She started by asking for a photo of my flaccid, uncaged clitty—I was no longer permitted to call it ‘mine’ or anything else but ‘clitty’. I obeyed. At first, I felt exposed; I would have preferred sending an erection picture, but that wasn’t what she wanted. I had to learn that it was hers now. This realization turned me on more than expected because there was something liberating about letting go of ownership. Next, she told me to buy panties and stockings and post photos without showing the clitty. Though I’d bought underwear before for others, never for myself. The embarrassment made me repeat ‘not for me’ too many times to the shop cashier, yet knowing they were actually mine thrilled me. I was suddenly eager to get home and dress up for MistressS.
As soon as I returned, I put on black panties and stockings and took some pictures. I was surprised by how good they felt and how sexy—but slightly embarrassed—I looked. I sent the photos where I thought I appeared best, and Mistress posted them here for everyone to see. To be honest, I was terrified of what people would think, but surprisingly, I received many likes and compliments on my appearance. This also turned me on more than anticipated.
Since then, either I or MistressS have shared numerous pictures of me, including one where she ordered me to raise my Boi pussy (no longer just ‘my ass’) high with my chest pressed to the floor as if ready for pegging. I did it and felt incredibly embarrassed and nervous; I nearly asked her not to post that image. Fortunately, she decided to share it anyway. It has become one of her favorites because she sends it back to me almost daily as a reminder that I am hers.
As many of you have noticed in my comments on MistressS’s photos, she looks amazing. She also asked if I wanted to masturbate one last time before the cage arrives, and I readily agreed. It had been nearly a week since my last orgasm, so I was past my usual abstinence period. As soon as I said yes, she reminded me that learning what it’s like to be a sissy or a good husband requires learning how to clean up properly. So, just for a moment, the urge dampened until MistressS rekindled it, and I declared ‘oh hell with it,’ wondering how bad it could really get. Afterward, I put my own semen into my mouth (honestly, I almost struggled), finding it warm and salty. I had to take a photo as proof that I’d done it (not the best picture). As promised MistressS, I swallowed everything down. Since then, whenever given permission for an orgasm, I must clean up. As MistressS put it, you never know when your wife might want you to tend to her, so you need to be ready. Eating my own cum is something I still need to work on; my initial reaction remains ‘ewww’ rather than ‘hmm,’ but MistressS assures me I will learn to enjoy it.
Finally, the cage arrived (a lovely sissy pink one), and I was told to wear it to work while sending pictures of myself in stockings and panties. It was a thrill and quite a learning curve. I attended board meetings with several important directors, feeling more nervous than ever: could they see it? Was it sticking out or looking lumpy? Did my leakage show through? I was excited, and the clitty kept trying to get hard almost constantly. After a while, I ached to be released but held on for most of the afternoon before being allowed freedom. The sensation with the cage on was amazing; it felt like MistressS had a permanent grip on her property, letting me know it was no longer mine. As expected, she posted pictures of her caged sub for everyone to see.
Since then (as you may have noticed), I’ve been posting photos proclaiming myself as MistressS’s property. This proved more embarrassing than expected because I am now telling everyone that MistressS is my owner and I no longer hold control. As an alpha male, this was both exciting and awkward, but since becoming accustomed to it and openly acknowledging her dominance over me.
My journey of self-discovery still has a long way to go, yet already I notice changes in my attitude at home as well as my willingness to please MistressS according to her commands.
I have several tasks ahead that I view with equal parts anticipation and dread. Especially the one where I must dress up fully: bra, panties, stockings, heels, and a short skirt/dress. Mostly because I know MistressS wants me to learn how to take a dildo and start milking; it seems inevitable given the attire.
That is a brief (ish) summary of my journey so far.