orinthsone A New Chapter in My Chastity Story

“Create a journal,” she instructed. “If I have the power to command, consider this an order.” So here is my journal. Three days ago, I was secured in a chastity cage. The timing of when it might be removed depends on a very close friend who agreed to keep the key. It’s really that straightforward. In reality, I could remove it whenever I wish. However, doing so would reveal what I’ve done. If I take it off now, I’ll likely regret it (assuming this arrangement lasts). Her phrasing was: “It will be Serious Business.” And that is precisely how I want it to feel. I have been interested in chastity devices for years. Until perhaps a dozen years ago, I wasn’t aware they were such a modern trend or had ever been designed for men, but since then, I’ve practically obsessed over the concept. I experimented with plastic models on occasion, but they never fitted well or functioned properly. Two to three years back, I commissioned a custom metal cage with most of the available options (well, mostly). For those curious, it’s a Jail Bird model by Mature Metal. It was vastly superior, yet I lacked a keyholder at the time, and my life circumstances weren’t right for seeking one out. Plus, I experienced some chafing and comfort problems when wearing it beyond just a few hours. Also, it wasn’t fully secure; I would need a piercing for that level of security. Though never forgotten, I set it aside. Fast forward to about two weeks ago. For reasons unknown, the chastity cage was on my mind, so I decided to try cycling while wearing it. To my surprise, it worked perfectly fine with zero discomfort. I got excited. For once in a long time, long-term confinement seemed like a practical option. I had to share this news. So I told Ms. Jilly. “Are you looking for someone to hold the key?” she asked. I believe we’ve been internet friends for nearly ten years. She lives across the country from me; I visited her once several years ago. Despite the distance, she is one of my closest confidantes—perhaps even the closest—and I am equally close to her. We share everything with each other. For instance, I told her about my chastity fetish. We had discussed the possibility of her being my keyholder a few times previously. “Consensual nonconsent” didn’t quite appeal to her back then, and she didn’t seem particularly interested in BDSM generally. Recently, however, she has begun exploring her sexually dominant side and is seeking subs. Before she asked me that question, I hadn’t realized she had changed her mind. But she had. “I’ve embraced my Goddess nature.” She enjoys having control. I posed a question to her: “I trust you would let me out if it truly became necessary. But are you willing to say ‘no’ even when I find the situation difficult?” “Yes,” she replied without pause. It was possibly the hottest response she could have given me. I possess both a security screw and its key, along with an extra hole that accommodates a plastic padlock seal. She asked if I could pull out (remove the device temporarily). Admittedly, I could do so, but my testicles would remain trapped inside. We discussed getting a Prince Albert piercing for true security. She thinks it sounds very appealing but remarked, “One step at a time.” I honestly couldn’t have imagined a better person to hold my key, and she seemed entirely on board. For the following week, I wore the device according to my own schedule to sort out any kinks. I wore different types of pants with it. I took it to work, to the grocery store, and around my family. I exercised in it, showered in it, and slept in it. New underwear resolved all my comfort issues. I decided that while a smaller base ring would be better eventually, that adjustment could wait. Otherwise, there was no practical reason I couldn’t wear this chastity device continuously. During that week, we discussed boundaries somewhat. I want the ability to remove the device quickly and independently in an emergency. But I don’t want it so easy that she doesn’t know; I want this to feel real. I mentioned that public humiliation isn’t really my thing. Other than that, I am happy for everything to be on her terms. She said that pleased her. Ms. Jilly and I also chatted about our relationship dynamics. It’s a new direction we are taking together. We agreed to build upon our friendship rather than replace it. We would be opening doors, not closing them. The bond we already share is cherished by both of us, and neither of us wants to lose that. I mailed one of the keys to her via post. I told her I was ready to surrender control. Her internet connection had gone down, so we planned to finalize everything over a phone call. I stayed aroused all day long. After putting her daughter to bed, she called me. She invited me to enjoy one last release before lockup, but feeling self-conscious, I declined. She warned that she hadn’t decided how long the confinement would last yet: “It could be a single day, or it might stretch to a month.” I held firm and declined again. Once my cock softened sufficiently, I placed the cage on, tightened the security screw, and locked it with a numbered plastic seal. I emailed her a photo of the setup. It was now official. I slept without trouble. I woke up once or twice as my erection tried to form, causing some discomfort, but that was expected. I went to work and had a productive day. I found myself noticing breasts more often, and I was very aware of my cock. It attempted to become erect repeatedly; the pressure made this keenly noticeable, and it felt like it had no control over itself. The thought of masturbation haunted me several times during the morning. In the afternoon, while filing documents away, I caught myself fantasizing about receiving a blowjob. It was an intriguing day. The next day began well enough, but by mid-afternoon, my enjoyment waned. I started missing having access to my cock. You know that feeling when you wear shoes all day—even if they are comfortable—and especially after falling asleep in them? You just feel like taking your socks and shoes off so they can relax and breathe? That is exactly how my cock felt. It wasn’t even about sexual pleasure anymore; I simply wanted to hold it and squeeze it, perhaps reassuring myself that it was still there. I began considering asking Ms. Jilly for some free time. Although I didn’t ask, the thought occurred to me. I hadn’t given up on the experience itself, but I wondered if this particular predicament had nothing more enjoyable left in store for me. I think I was getting a bit depressed. Last night proved tougher still. My cock worked harder to get hard, and it became somewhat painful. I woke up repeatedly to use the bathroom and urinate. I thought I understood that this aspect would improve over time rather than worsen immediately, but apparently not right away. This morning, I called in sick to work and stayed in bed. I told Ms. Jilly my experience was no longer so enjoyable, though I did not request a change in status. Then something interesting occurred. Ms. Jilly updated her profile for finding subs and let me view it; it now included this statement: “I have a boy in chastity now, and I find myself enjoying the process.” Immediately and solely because of that, my appreciation for my situation grew. If Ms. Jilly is gaining something from enforcing my confinement, then apparently, so am I. It wasn’t even a particularly emphatic declaration, but it made all the difference to me. I am eager to discuss her side of things with her more. And that is where I stand currently.