This journal will summarise the journey between my keyholder (my Lady) and I. My Lady is also writing one from her perspective so you can get her thoughts on this as well by going here - https://www.chastitymansion.com/forums/index.php?threads/my-journey-of-becoming-a-key-holder.35115/. Hopefully, this will be interesting and informative for those at the start of their journey as well as those more experienced. I was the one who introduced my partner to the idea of chastity, before I told her about it she had never heard of it. She has always said she was very vanilla before we started this. I was the opposite, I have for a long time been interested in chastity and other areas of kink. Some of which we have incporated into our lifestyle and others we have not. While I had self locked before I had never had a keyholder as I had never trusted anyone with this before. It was around two years ago that I first dared to bring up the idea of chastity with my partner. I do not remember the conversation perfectly but I do recall that she could not really understand what the point was. I did not show or explain about the cage at this point, I was really trying to get across the concept that it can be nice to be denied. I feel this went okay, at least it was not a complete disaster. A few weeks later I brought out the actual cage and at that point I think it really put her off. For her it was strange looking and just odd. I did try my best to make her understand it was just an idea and not something we had to do. At some point around this time I wore it for a night and she was not keen as the padlock made it uncomfortable and again it was just odd for her. Shortly after this I stopped wearing it and did not mention it again. Some time after that, a few months, she brought it up herself and we started expermenting with it once more. Making it more suitable for us by getting a new (heart shaped) padlock which also had a much more attractive key. She was keen to wear the key and that was something which excited me as well. At this point we kept to periods of being locked that varied between a few days and maybe a bit over a week. We could try different things and basically have fun with it and so I was delighted that together we were comfortable with it. I do not remember how things worked that clearly now but I feel it was something we would try on and off. As time went on it was more and more but I do think we did in general have time 'off'. I had been aware of this forum and others for sometime but it was in August of 2018 that I joined it with a joint account with my Lady (she now has her own account). We chose that route because this again was a big step for her and so it made most sense to try and step into it gradually. The forum had lots of useful information and guidance but of course there was also a lot of helping her separate the fact from the fiction. As we had been getting increasingly serious about chastity over the months it was at this point we started looking into better cages. The CB-6000 I had been wearing was really a pretty great cage for starting, highly adjustable and broadly comfortable for short periods. Its flaws were really in its wear for longer periods and the length of the it made it awkward for some activities and clothes. After a lot of research we settled on a Steelworxx Looker 02. I am not pierced there so there was no possibility of something that uses PA to secure it such as a Lori device. We got the new cage sometime in mid September and it was night and day a huge improvement over the old one. Measured to fit meant it was no larger than it needed to be and the design made it much easier to clean etc while in use. Not being a PA device it is still of course not absolutely secure and it is still not suitable for all activities but it is a huge step forward and a great cage for us. The downside of this cage is simply that the key is really not suitable for wearing as jewelerry. We searched high and low for a way to customise our key into something that my Lady could wear but got nowhere. One day on the forum we spotted a post by JosieLynn Jewell, my Lady got in touch about a key and lock. Thanks to JosieLynn we now have a very nice key which my Lady loves to wear, we really could not be happier with that result. We also started introducing FLR around this time. Initially this did work well for us but I feel we ended up making our approach to dogmatic. We had spreadsheets and other documents for tracking everything and that ended up being very time consuming and actually probably ended up being a barrier rather than enabler. It felt very right at the time as that it was easy for my Lady to justify a punishment and to spot things that were missed etc. However in retrospect I feel that we do not need that and if my Lady wishes to punish me that is her choice and she does not need proof of an issue to justify it. It may sound negative because after 5 or 6 months this FLR and chastity came to an end. However it was also a wonderful time, my Lady stepped into her role with incredible ease. She was such a natural in many respects at this and I was in absolute awe of her. It is certainly true that in person she was more shy about it but even then she could often do it very well. So she really did make my fantacies come true and it is important for me and her to remember that rather than just think about the fact it did not quite work out. Fast forward to the present day and we have restarted the chastity for a bit over a month. I would say that this time we are trying to be a lot more flexible and less overly structured in our approach. At this point I feel that my Lady can ask and demand anything of me, though if it is not something we have agreed we are comfortable with it may be the case she cannot punish me for not doing it. In reality that does not really matter because it is my ultimate desire to please her and make her proud of me so regardless I am always trying to do whatever she asks as well and as quickly as I can. I am really excited we have started this back up again but I am also glad we had the break earlier in the year. I think the path we had taken was too much too quickly and also very heavy on paperwork rather than actual interactions between us. I believe we have no doubt learnt a lot of lessons from our earlier experience and we will together be able to make this work a lot better this time. I cannot wait to see how this develops and to keep you up to date on the forum. Finally I hope when my Lady reads this she will understand how incredibly appreciative I am of her for taking part in this with me and for being so understanding. I also hopes she will get an idea of just how amazing she has been as a keyholder and that every day she amazes me.