Journals and blogs discussion

This journal will track the path between my keyholder (my Lady) and me. My Lady is also keeping a diary from her point of view, so you can read her perspective here - on this community page. Hopefully, it proves both interesting and useful for beginners as well as those with more experience. I was the one who first introduced chastity to my partner; before I mentioned it, she had never heard of it. She always describes herself as very vanilla prior to us starting. I am different; I have long been interested in chastity and other aspects of kink. We have incorporated some into our lifestyle while leaving others out. Although I had self-locked previously, I never had a keyholder because I hadn’t trusted anyone with it before. About two years ago, I first broached the subject of chastity with my partner. The conversation isn’t perfectly clear in my memory, but I recall she struggled to grasp the purpose. At that stage, I didn’t show or explain the cage itself; I was mainly trying to convey that denial can be pleasant. I think it went reasonably well, at least not a total failure. A few weeks later, I brought out the actual device, and I believe this put her off for a moment. To her, it looked strange and odd. I did my best to reassure her that it was just an idea, not a requirement. Around then, I wore it overnight; she wasn’t keen because the padlock caused discomfort and again seemed odd to her. Shortly after that stoppage, I stopped wearing it and didn’t bring it up for a while. Some months later, she brought it up herself, and we began experimenting with it once more. We made it work better for us by getting a new heart-shaped padlock that came with a much prettier key. She was eager to carry the key, which pleased me greatly. At this stage, our locked periods varied from a few days to just over a week. We could try different things and generally have fun, so I was happy we were comfortable together. I don’t recall the exact mechanics now, but it feels like something we tried intermittently. As time passed, we did it more often, though I believe we still had plenty of ‘off’ time in general. I had known about this forum and others for a while, but I joined here in August 2018 with my Lady on a joint account (she now has her own). We chose this path because stepping into the community was another big move for her, so it made sense to ease in gradually. The forum offered plenty of useful info and guidance, though there was also much helping her distinguish fact from fiction. As our commitment to chastity grew over those months, we started looking at better devices. The CB-6000 I had been wearing was a solid starter cage: highly adjustable and generally comfortable for short durations. Its weaknesses showed up during longer wear times, and its length made it awkward with certain clothes and activities. After extensive research, we chose the Steelworxx Looker 02. Since I am not pierced, there is no chance of using something like a Lori device that secures via PA (penile attachment). We received our new cage in mid-September, and the difference was night and day—a huge improvement over the old one. The custom fit meant it wasn’t larger than necessary, and the design made cleaning easier while worn. Although not being a PA device means it isn’t absolutely secure and doesn’t suit every activity, it represents a significant step forward and is an excellent cage for us. The only drawback of this particular cage is that the key itself isn’t really suitable as jewelry. We searched everywhere to find a way to customize our key so my Lady could wear it, but without success initially. One day on the forum, we noticed a post by JosieLynn Jewell regarding her keys and locks. Thanks to JosieLynn, we now have a lovely key that my Lady adores wearing; we are very pleased with that outcome. We also began introducing FLR (Female Led Relationship) elements around this time. Initially, it worked well for us, but I feel our approach became somewhat dogmatic. We used spreadsheets and other documents to track everything, which ended up being quite time-consuming and perhaps acted as a barrier rather than an enabler. It felt right at the moment because it made it easy for my Lady to justify punishments and spot missed duties. Looking back, however, I feel we don’t need that level of structure; if she wants to punish me, she can choose to do so without needing proof. It might sound negative since this FLR and chastity phase ended after about five or six months. Yet it was also a wonderful period where my Lady stepped into her role with ease. She seemed very natural in many ways, and I admired her greatly. In person, she was more shy about it, but even then, she often did well. So she truly made my fantasies come true, which is important for both of us to remember rather than just focusing on the fact that it didn’t last. Fast forward to today: we have restarted chastity for a little over a month. I would say this time around we are much more flexible and less rigidly structured in our approach. Currently, my Lady can ask or demand anything from me, though if something isn’t within what we agree is comfortable, she might not be able to punish me for it. In reality, that doesn’t matter much because my ultimate desire is to please her and make her proud; thus, I always strive to do whatever she asks as quickly and well as possible. I am really excited about restarting this journey but also glad we took a break earlier in the year. I think our previous path was too intense too soon, relying heavily on paperwork rather than actual interaction between us. I believe we have learned many lessons from that experience and will be able to make it work better together now. I look forward to seeing how this develops and keeping you updated here. Finally, I hope my Lady reads this and understands just how appreciative I am of her for participating with me and being so understanding. I also hope she realizes how amazing she has been as a keyholder and that every day continues to surprise me.