So, once I lost Lucie at the end of Locktober, I planned to skip NOvember and then take part in Denial December. But then I met Michele and NOvember was back on. When the chemistry never developed with Michele, I decided I wouldn’t renew our agreement after NOvember ended. And since I’m doing NOvember after all, I reckoned I would take a break in December before searching for a new keyholder. Out of curiosity, I decided to explore Chaster, a keyholding application for chastity device wearers and keyholders, and this is how Chaster changed my December plans.

I have known about Chaster for years and knew some guys on Chastity Mansion who used it. It seemed more an application aimed at helping guys who self-locked to stay honest using timed locks. When I looked into Chaster back then, you needed a box with a re-settable combination lock to store your keys in. Then you set a combination without looking, took and uploaded a photo of the combination to the app without looking at it, and when the timed lock expired, you retrieved the combination from the app. I didn’t find it that interesting and never visited the website again until a few days ago. What I discovered after returning to the site and registering was the Chaster app has changed a lot since its inception. Now there are actual keyholders there who supervise the timed locks.

Most of the timed locks featured on the app are called “community locks” meaning anyone registered with Chaster can take part. Registration is free, although they do have a paid option that gives you access to more features. But I think most people would find the free option meets their needs. There are free community locks, but paid locks also exist that require a financial tribute to the keyholder. The paid keyholders must register as “findoms” per Chaster’s terms of service requirements, but they aren’t all findoms in the sense we usually understand the term. Some are, but many aren’t, or at least there are some who will do straight keyholding without you having to take part in financial domination. You only have to pay the agreed tributes. The findom label is only Chaster’s way of letting members know when a lock requires a payment to the keyholder to avoid any confusion.

Financial domination is one kink I just don’t get at all. Why would someone find it sexually arousing to give a complete stranger money who gives them in return nothing but insults? Sometimes lots of money changes hands. I’ve heard some guys have gone into debt paying findoms with credit cards. Judging from what I’ve seen on X (Twitter) I suspect many of these women aren’t even actual dominants but just garden variety “mean girls” looking for some easy cash.

Obviously, the attraction for fin subs must be the humiliation because that’s what these women dish out. It doesn’t appeal to me, but to each his or her own. I’m not judging anyone who is into the financial domination kink, I just don’t get it. Anyway, my point is not all, maybe not even most of the women labeled findoms on Chaster, are anything close to the findom types you commonly encounter on X who are all about the money and only about the money.

While perusing the community locks last Friday on Chaster, many of which were free, I noticed I found those requiring tributes to the keyholder much more interesting. And I found one woman offering some locks I found particularly intriguing. Many were great as she designed them, but I also read that she would customize the locks to individuals. So, I sent her a DM asking for more information, and enjoyed a delightful chat. She turned out to be a very personable woman and helpfully explained how Chaster worked and what I could expect. Then we chatted a little more about the customization she offers, which mostly has to do with the length of the locked period and the sort of teasing tasks she provides.

Long story short, the more we talked, the more the woman impressed me. We will call her Amanda since I don’t have her permission to use her Chaster identity. Like I did with Lucie, I sensed Amanda was obviously an authentic dominant woman, not someone just playing a role. She told me she had one full-time sub but was looking to acquire a second sub if she found someone who met her standards and seemed a good fit. Then she asked if I was interested in finding a full-time Domme. When I admitted I was, she offered me a seven-day trial during which we would get acquainted and see if we were a good fit. When I said I was interested in the trial, she sent me an application for consideration to complete which would help her determine how much kink compatibility we had.

I’ve completed such applications for Dommes before back in my active BDSM community days. They are quite common or were. But Amanda’s was very comprehensive and well designed. It seemed clear she aimed the questions at determining whether I was a true submissive or just a guy willing to submit during play to satisfy my kinks and have some sexy fun. Besides the questions, there were also sections for me to list my kinks, soft limits, and hard limits. I spent almost two hours completing it and then sent it back to her when I had finished. The application didn’t ask for any private information, just questions about my kinks, interests, desires, and opinions about the D/s dynamic. I felt very comfortable completing it and appreciated how detailed it was. I felt it gave me the chance to provide Amanda with a good idea of what kind of person I am and what I’m seeking.

We chatted again later Friday evening after she had reviewed my application. She told me my responses had impressed her, and she felt comfortable proceeding with the seven-day trial and if it seemed we clicked, we could discuss a more permanent arrangement. Frankly, by the time we said goodbye Friday evening, I already felt more chemistry with Amanda than I’ve felt with any keyholder I’ve had except Lucie and my first keyholder.

We chatted again on Saturday afternoon. I had already told her about Michele and my obligation to complete November for her. Amanda asked if I wanted to take a few days off after NOvember before starting the trial since I was doing NNN back to back with Locktober. That sounded tempting, but since I already felt like I would probably be doing Denial December, I told her I was willing to start whenever she wanted to start. Immediately she said in that case we would begin on December 1. I felt sure that was what she had in mind all along, and I had scored a point in my favor by not taking the offered days off.  She then mentioned if things went well during the seven-day trial, as she expected they would, then we could just continue with Denial December. I fully expect that will happen as Amanda and I seem to get on well. Before we said goodbye, she had me send her photos of all the toys I had available to play with so she could start creating the teasing tasks for the seven-day lock.

Actually, the more I’ve thought about it, the more eager I am to finish off the year locked. Yes, even a brief break would have been nice, but I know I can finish off NNN and make it through one more month. Amanda knows how long I’ve spent locked, so I feel cautiously optimistic she will allow me some type of release after Denial December before we continue. And yes, I’m also optimistic we will continue. I have a good feeling about Amanda. She doesn’t remind me of Lucie because she doesn’t seem to have the sadist edge to her that Lucie does. But she reminds me a lot of the very first keyholder I had who was always my favorite until I met Lucie. Interestingly, Amanda is Canadian as was my first keyholder, so I hope that bodes well.

I will finish NOvember with Michele and then I’ll start another new chapter in my chastity journey with another new keyholder. And I’m very excited about that because I think this time, I’ve found a keeper. If you’re looking for a keyholder, either free or paid, you might want to check out the Chaster app if you haven’t before. It seems like it might be a good place to find one.