30 Days of Chastity: Retrospect

Continued from 30 Days of Chastity: Week Four

I am still trying to figure out how I feel about being locked in chastity. Being locked for short periods of time is a very different experience from being unlocked for short periods of time. Until recently, my Domme had not kept me locked in chastity very often, or for very long. The longest I had ever remained continuously locked in chastity was less than two days. Aside from a few special occasions, my Domme had generally left me unlocked.

For the last month or so, my Domme has kept me in chastity by default. She has permitted me to remove the cage under certain circumstances and for certain occasions, but I have spent the majority of the time locked in the device. Or at least, it sure felt like it.

Wearing the cage is pleasurable at first. It is a constant reminder of my Domme, and Her power over me. Being caged in public is a bit of a thrill for me. It feels like my Domme and I are sharing a special secret. Mostly, I enjoy the pleasure that She derives from my suffering and Her control over me. Her pleasure is my pleasure.

The device becomes more difficult to deal with the longer I wear it. I am constantly aware of the cage, and I must be careful how I walk, sit, and urinate. I can’t fully close my legs without crushing my testicles.

Driving long distances while locked can be very irritating. In this circumstance, I have difficulty finding a position that is comfortable for both my back and my caged package, and frequent adjustments are necessary. The cage can become twisted around, which can be very uncomfortable.

The cage can be quite painful when my testicles want to retreat into my body and the device won’t let them. When I have this problem, it can cause the ring of the device to chafe my scrotum, and result in long term pain that remains well after the device has been removed.

Being locked in chastity is very distracting, as I am constantly aware of the device. Focusing on anything can be very difficult. I feel like my capacity for problem solving and my ability to write are diminished while I am locked. If I am anxious about something, being caged can exacerbate my anxiety.

Not being able to cum when I want can be challenging. Having an orgasm is a great way to temporarily escape from whatever worries are plaguing my mind, and can help me get to sleep when I have a bout of insomnia. Sometimes I just want to feel my cock pulse in my hand as I shoot a hot load. Sometimes I just need release.

On the other hand, I do have a history of masturbating more than necessary. I used to masturbate at least twice a day. Some days I would spend several hours masturbating. Being caged for days at a time has reduced both the frequency and durations of my masturbatory sessions, leaving me more time to be productive.

I have learned that I was wrong to make myself cum while caged without my Owner’s permission. Although I had told myself that I was not technically disobeying Her commands, by making myself cum without Her permission I had taken away Her control over my orgasms. Despite being able to rationalize my actions at the time, I knew deep down that She would not approve.

I did not realize how badly I had fucked up until that night I beat Her at cards. That night, She explained to me that the device was just a fixture. She likes the way it looks, and thinks it’s sexy, but Her control over my orgasms is the aspect of locking me in chastity that brings Her the most pleasure. She was confident that I would not betray Her and cum without Her permission.

After we had parted ways, I thought about what She had said and I realized that by making myself cum in the cage I had both taken away control from Her, and betrayed Her trust. I felt horrible. I knew that I needed to tell Her what I had done. I knew that She would not be pleased. I should have told Her immediately, but I didn’t. I must have feared Her reaction. I resolved to tell Her about my transgressions in writing.

It was a couple of days later when we were out having dinner that we began talking about Her plans for pegging me, as my reward for winning the card game. She had been discussing it with one of Her favorite bulls, and had mentioned to him Her desire to keep me locked in chastity while She was pegging me. I actually found the idea a little exciting. I had never before been pegged while caged.

She told me that the bull had come to my defense, saying something like, “Isn’t the point of being pegged so he can cum?” It actually isn’t. I am quite adept at making myself cum. Being fucked in the ass by a true Domme is a much richer and more complex experience than just spurting out a load of ejaculate.

I never expected that my Owner would make me cum. One of the first things She had told me when we started seeing each other was, “Know that your wimp dick is the last thing on my mind, ever. I could give a fuck if you ever cum.” I just prayed that She would use lubricant. I also wanted the experience to be as enjoyable for Her as it would be for me. If pegging me while I was locked in chastity would increase Her pleasure, I would be more than happy to receive such a fucking.

I said to Her, “Well, it is possible that I could cum in the cage.”

She was surprised and possibly a little excited. “You think you could cum in the cage, really?”

“I mean, I have before.”

“Really?! When?” She asked excitedly.

“Well . . . “ I hesitated and let my voice trail off.

Her eyes narrowed and Her expression hardened. “When?” The tone of Her voice had changed from excitedly curious to suspicious and accusatory.

I don’t ever want to lie to Her. I had to come clean immediately. I explained that I could not tell Her exactly when without looking at my notes, but I had made myself cum a couple of times while She had me locked in chastity. I don’t remember Her exact words, but She was clearly upset. She was angry, but worse, She was vastly disappointed. I felt incredibly ashamed. I had failed Her.

I begged for Her forgiveness. I explained how I had rationalized my actions, telling myself that making myself cum in the cage was okay because I hadn’t technically disobeyed Her words. I explained to Her how badly I had felt the night She told me what the chastity device meant to Her. It was that night when I realized that Her control over my orgasms was the main aspect of the device that She derived pleasure from, when I realized how badly I had failed Her. I explained that I had always meant to tell Her in writing. She said that I should have told Her immediately; I knew I should have.

I was lucky that I had served Her well that night. Her reaction to my transgressions could have been much harsher, had I not. She did not stay upset with me for long. I knew that I would be punished, as I deserved, but I also knew that She would forgive me. I was thankful to have everything out in the open and know that we would be able to move past it. I won’t make the same mistake in the future. I will continue to progress for Her, for as long as She will help me; I hope it is forever.

Long term chastity has never been an interest of mine. I bought my original chastity cage out of curiosity. I had never worn it for more than a few hours at a time until my Owner instructed me to do so. I enjoy being under Her control, and the constant reminder of Her, but even though my new device is much more comfortable, it still becomes painful and incredibly distracting after wearing it for just a few days.

I pray that my Owner will take pity on me, and not require me to be locked in chastity by default. Being locked in chastity for a day or so on a special occasion is pleasurable. Beyond two full days of being caged, the only pleasure that I feel is derived from Her pleasure. I expect that if I were to remain caged for much longer, I would feel nothing but discomfort, distraction, and distress.

Recently, She has been allowing me to be free from the cage for the most part, but has been controlling my orgasms nonetheless. I know better than to make myself cum without Her permission now. She is my Owner. I do not know what She will require of me in the future. If it pleases Her, I will endure the cage for as long as I possibly can. If it pleases Her, I will not cum without Her permission. Her pleasure is my pleasure. I know that She will take good care of Her property. I will do my best to make Her proud.

2 thoughts on “30 Days of Chastity: Retrospect”

The greatest way for you to please my Owner is to leave comments on these journals. She expects that you will keep your comments related to the content, rather than verbally ejaculating all over the page. You will show Her the respect that She deserves.

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