Journals and blogs discussion

I’ve made the choice to begin a continuous journal chronicling my time in chastity with my dear Wife. (She has now insisted that I do it!) The purpose is for me to remember, and so she can observe my thoughts and feelings throughout this ongoing journey.

At 32 years old, I am married to an incredible woman who also holds the key. Our relationship has been evolving into a chastity dynamic over the past few years, but she has recently embraced it with much more seriousness. I have noticed that for many couples, there is a specific moment when the keyholder starts to recognize the power and appreciate the benefits of chastity. Once that shift happens, the keyholder takes control, and you begin to understand why everyone warns you to “be careful what you wish for!”.

Some background: Our initial step into chastity happened after I was away on a trip for nearly two weeks. I had been feeling quite horny and browsing online sex shops. (I have always been very kinky; she is somewhat kinky, though typically more submissive to me. However, she could be pushed too far easily and didn’t share the same strong masochistic tendencies that I do). While looking through their selection, I spotted a steel cock cage. Bondage has appealed to me since puberty (perhaps even slightly earlier, though I didn’t fully understand it then), and this was my first time seeing a cock cage. It instantly turned me on, so I ordered one to use when I returned from the trip.

Upon returning home, we met at a hotel near the airport (we live more than an hour away from the nearest airport) and enjoyed some fantastic kinky sex. I wore the cage for a while as she teased and spanked her; it was a great time for both of us.

After that experience, I became obsessed with finding a device that felt inescapable yet comfortable enough to wear without interruption. I tested various contraptions, including a CB6K, Holy Trainer, and several Chinese metal devices that worked well, but I soon realized that without a piercing, it is difficult to truly prevent pull-out. I am a significant grower; if the base ring was tight enough to make escape hard, my balls would ache constantly. Making the base ring larger stopped the constant pain in my balls, but then I would practically slip out the back of the cage on my own. The CB series had inserts for me, but they ended up causing abrasions and cuts on my member and couldn’t be worn for long periods.

I finally got a frenum piercing and started experimenting with ways to secure it inside a cage. I settled on Red Chili chastity devices and had a custom metal cage made that traps my frenum, making pull-out impossible. (You can read more about my specific cage in the archived discussion).

Looking back, I think I probably should have gotten a prince albert piercing since it is by far the most popular option, with many cages designed to work with PAs. Also, I find the frenum piercing to be delicate and easily irritated by too much tugging. However, I am reasonably happy with my setup and can still use a urinal if I ensure everything aligns properly.

So now I had a cage that was truly inescapable. Sure, bolt cutters could defeat it, and the lock is an obvious weak point, but short of destroying the padlock, there was no way to free my penis without her knowing.

Yet, she hadn’t quite reached the point where she understood why this all mattered. Once I got comfortable wearing the cage, she would take the keys, and we would play for a few days. Eventually, she let me out, we both cummed, and that was it until next time. Usually, I had to lock myself back up when horny and make her retrieve the keys. She wasn’t always careful with them, often leaving them on the nightstand or kitchen counter. This disappointed me because my major turn-on is lack of control. I only enjoy bondage if it feels inescapable; same for having my dick locked up. If I can get out, what’s the point!

But over time, she became a better keyholder. In the beginning, she was doing it all to please me and fulfill my fantasy. As we discussed it more, she began taking some interest in it herself. She started locking me back up after playing or making deals like “you can get out and cum now, but you have to go back in tomorrow.” These kinds of things drove me wild.

Then we started a point-tracking game. I needed 3,000 points to be released, but every time I hit 1,000 points, I earned a teasing session. Chores and romantic outings awarded points, meaning I had to work for my release.

The point system worked fairly well, but it still felt like she was doing everything for me. Sure, more housework got done, and I was checking items off the honey-do list, but it started feeling a bit cheap, as if I were paying for her services with tasks. If I earned enough points for a tease but she wasn’t in the mood or the timing was off, and I didn’t get my tease immediately, I felt cheated and got pissy. Still, we were making progress, and the game taught her to be stricter, not allowing me release or orgasm unless I had truly earned it.

But it still wasn’t quite working perfectly. After one of our games ended and I was released, we went two or three months without any chastity routine. I started jerking off daily, sometimes more. The distance between us grew, and our sex life became almost non-existent. (We have been together for eight years with opposite schedules; since I was taking care of my needs on my own, I wasn’t in the mood when she wanted it.) We were also dealing with issues regarding having kids and other relationship matters that nearly ended our marriage. We eventually worked out those external problems and started talking about chastity again.

Next post: A new beginning.