Continued from 30 Days of Chastity: Week Three

In the morning, I donned the chastity device again. After work, my Domme came over and allowed me to shave Her legs. I wore nothing but the chastity cage while I served Her. She occasionally gave my caged package a little kick with Her foot. She told me how much She liked the look of the new cage compared to the old one. She said it was, “sexier.” I was so happy that She was pleased by my new cage. She permitted me to don some underwear to sit on the couch and watch some TV with Her.

After She had left that night, I received a text from Her giving me permission to remove the cage for one hour that night and masturbate to porn. “Femdom ONLY!” She said, “Cuckolding OK.” I jerked off for about forty minutes before cumming hard to some femdom enforced cocksucking porn. I got cum all over the place.

My cock really wanted out of the cage that morning. It kept trying to get hard for what must have been two hours, while I kept trying to go back to sleep. It was an incredibly frustrating time. I wore the device throughout my work day, and then out doing errands and having dinner with my Domme. I have fun wearing the cage while out in public with Her. It’s like we’re sharing a special secret together.

The hour was a little after midnight. My Domme had already gone to bed. I was unbelievably horny. I couldn’t possibly sleep. I knew that having an orgasm would help, so I put a vibrating butt plug up my ass, and put on some porn; a compilation of guys cumming while locked in chastity. This particular butt plug can be paired with a phone and controlled with an app, and it features a mode that will base the vibrations off of the sounds in the surrounding environment. I played some music for additional background noise.

With the vibrating butt plug in my ass, and a Hitachi wand pressed against my cage, I came incredibly fucking hard. The orgasm was incredibly intense. I was loudly vocal, moaning uncontrollably, which is rare. I am usually very quiet when I cum. My cock was dripping cum out of the cage. Finally, I was able to sleep.

I woke up with the cage tight around my cock. I went to the bathroom and urinated to relieve the pressure, then went back to bed. I couldn’t get back to sleep though. My cock was relentless, and kept trying to get hard until my alarm went off and I had to get up for work.

I wore the chastity device to work again. I was on the road most of the day, driving. I had to keep adjusting the cage, and my balls, over and over again. I think I need to get some kind of underwear with some more support. The weight of the cage dragged my balls down to the ground, pulling them back in between my thighs until I was practically sitting on them. The cage got twisted around as I was trying to adjust it while driving. I stopped at a rest area to fix it. I had the same issues on the return trip.

I took the cage off before swim class. I was unable to put it back on after because I couldn’t get a private changing room. When I explained the situation to my Owner, She wasn’t bothered. “Don’t wear it to work tomorrow,” She said. “You can have the day off.”

“Oh, thank you!” I was so relieved.

“But you still can’t masturbate,” She added.

“Damnit!”

She laughed. “Is that more cruel?”

“I think so!” I said with a smile. She laughed again.

When I got home, I donned the cage again. I texted my Owner as soon as the device was back in place.

I woke up to my cock trying to get hard again. I laid in bed for another hour with my cock swelling against the chastity cage. My Owner had given me the day off from wearing the cage, but had specifically disallowed me from masturbating, so removing it before getting out of bed really wasn’t going to help me much. I did my best to get a few more winks of sleep before removing the device and getting ready for work. I was scheduled to spend that weekend with my girlfriend, so my Domme allowed me to be free from the cage. I was very thankful for my freedom.

On Monday morning, I began to wake up while my girlfriend was getting ready for work. I jerked off while she was in the shower, then fell back asleep. Sometimes I just want to feel my cock throbbing in my hand as I shoot my load all over myself. I put the cage on before work and wore it throughout the day. I was permitted to remove it later that evening while attending an event with my Domme. I was thankful to be allowed to leave the cage off after the event, while my girlfriend stayed over at my place.

I put the chastity device on in the morning, and wore it throughout the work day, as I have many times before now. As many times as I have worn the cage to work, I don’t think I will ever get used to it. I can feel my caged package swinging around while I walk. I have to take special care how I sit down, so as not to squash my testicles. I feel weird being around my co-workers while caged. Perhaps I feel more vulnerable than usual.

The worst part of wearing the cage at work is the constant distraction it causes. The device is always on my mind, as is my Owner. I find that anything that requires mental focus becomes much more difficult while caged. Whether I am writing or problem solving, I feel that my mental acuity is terribly diminished while I am locked in the device. Although my brain doesn’t necessarily need to be fully engaged for me to get through my work day, if my mind is addled for too long I begin to become extremely frustrated.

I was allowed to remove the device for swim class as usual. I put the cage back on immediately after swimming.

I woke up in the chastity device. I wore it to work again. Later that evening I served my Owner by carrying things for Her, while still wearing the chastity cage. It was a little bit awkward to be doing physical labor in public with my caged package swinging between my legs, but I didn’t mind. I knew that I was being helpful to my Domme, and that She was enjoying bossing me around. I am sure knowing that I was wearing the cage added to Her enjoyment. I am always happy to serve Her.

I woke up in the cage, and wore it to work again. I removed the device for swim class, as my Owner has allowed me to. However, due to inclement weather, we didn’t get to swim that night. I helped my Owner shovel snow instead. I wholeheartedly enjoy assisting my Owner with labor intensive tasks. Performing such duties is guaranteed to please Her. Her pleasure is my pleasure, truly.

When that task was complete, She and I played a card game together; a game that She had taught me how to play. She offered me a special reward if I was able to win. When She asked me what I would like as a reward, I timidly asked Her if She would peg me. She had only fucked my ass with a strapon once before, which was also a reward. My request put a smile on Her face. She told me that She missed pegging me, and has wanted to do it more, but it seems like we always run out of time. I was elated to hear that She was looking forward to fucking me.

When She checked to see if I was wearing the device, I explained to Her that I had taken it off for swim class. I apologized for not bringing the device with me. She told me that She didn’t care. She explained to me that the device is just a fixture. She thinks the device is sexy, and She likes the way it looks, but it is Her control over my orgasms that She really enjoys.

Later, when I had thought about what She said regarding Her control over my orgasms, I realized how badly I had failed Her by bringing myself to orgasm while locked in chastity. I had cum without Her permission. Even though I had not specifically disobeyed Her words, I had done what She did not want me to do. I had taken away Her control over my orgasms, which was the main aspect of my chastity from which She derived pleasure.

Worse, my actions were a breach of Her trust. Even though I didn’t exactly lie to Her, I did not tell Her the whole truth either. I should have told Her immediately the first time I came while caged. I must have known deep down that what I did was wrong, even if I was able to rationalize it at the time. I must have known that She would not approve.

The realization of the immensity of my failure made me feel sad and ashamed. She deserves better. I knew that I needed to tell Her. I don’t ever want to be dishonest with Her. I need Her to be able to trust me as much as I need to be able to trust Her.

I find it difficult to talk about things face to face with people, even when I trust and love them. My anxiety can make it difficult for me to think clearly, and sometimes my brain will get caught in a loop while trying to find the right thing to say, and I’ll just shut down. I decided that I needed to write about my transgressions. Writing would help me communicate with Her effectively, as well as document my failures for all to see, and hopefully learn from.

Inconceivably, I did win the card game. She planned to reward me the next weekend that we were together. Unfortunately for me, I had only asked that She peg me. I had not been specific about which dildo would be used, whether or not I would be allowed to cum, or whether or not lubricant would even be used. I would likely be locked in chastity while She fucked me. I just prayed that She would decide to take pity on me and use copious amounts of lube. I could barely handle two of Her fingers without it.

I put the chastity device back on as soon as I got home that night.

Caged and ashamed

Concluded in 30 Days of Chastity: Retrospect