30 Days of Chastity: Week Two

Continued from 30 Days of Chastity: Week One


The chastity device is always incredibly tight when I wake up in the morning. I wore the device all day, spending most of the morning on household chores. I went over to my friend’s house and played video games in the afternoon. He had no idea that I was caged. He knows nothing about my slave status, despite having met my Owner when we visited the cabin his family had rented this summer.

The cage was quite awkward at times, mainly because I had to be careful how I sat, to avoid crushing my testicles. Once I got into the game, I was able to ignore the cage for the most part, but the sensation of the cage encasing my package was always present in the back of my mind.

I had difficulty getting to sleep that night. I definitely had too much coffee at my friend’s house. I was also feeling apprehensive about an event that I would be attending with my Domme the following day. The event was something I had not experienced before, so I did not know what to expect. I have high anxiety about being in unfamiliar situations with unfamiliar people.

Usually when I suffer from insomnia, my go-to remedy is to masturbate. Masturbating helps me to disconnect from the logical part of my brain that is burning itself out trying to solve a problem to which I don’t have all of the needed information, and may not even be real. The dopamine and serotonin released during and after orgasm make me feel happy and relaxed. Having an orgasm can be the difference between being able to sleep, and not.

Unfortunately, I was locked in chastity, and I did not have permission to remove the cage. My Owner had already gone to sleep. I had no way to get Her permission. I could not remove the cage, but I knew from past experience that I could make myself cum without removing it.

I put on some porn, shoved a vibrating butt plug up my ass, and pressed my Hitachi Magic Wand against the plastic cage. The trick is to find the sweet spot where the vibrations to the prostate complement the vibrations to the glans of the penis. When I came, it was an intense, full body orgasm. I moaned uncontrollably. Before long, I was sound asleep.

Looking back, I know I should have immediately told my Owner about cumming in the cage. At the time, it did not seem like a big deal. I rationalized that technically I had not disobeyed Her commands. I knew that She would want to know about it, but I decided that I would reveal the event in the upcoming chastity journal that I would be writing.


I woke up in the chastity cage again, and wore it to work. My Domme allowed me to take off the cage for an event that we attended that evening. I was not directed to return myself to the cage after the event. I jerked off vigorously in front of the computer that night. Nothing fancy, just my cock in my hand and some porn on the screen. I can’t remember what I was watching, but it was likely femdom. It was something kinky for sure.


My Domme came over to my place after work that night. We had dinner and watched some TV. She cuddled and kissed me. When She asked me if I had masturbated that morning, I could not remember. Most likely I did, though. Sometimes early in the morning, I’ll wake up just to masturbate. It’s a nice way to start the day. When She left, She directed me to put the device back in place.


When I woke up, the cage was extremely, uncomfortably tight. The device was a constant irritant throughout the workday. The grooves of the plastic ring dug into the soft flesh behind my scrotum. My scrotum was taught around my testicles. My foreskin poked out of the pee hole of the chastity device and rubbed against the inside of my underwear. I was extremely uncomfortable and distracted all day. I began searching for alternative cages online.

I had read somewhere a while ago that metal cages were more comfortable than plastic, but I was worried about the metal being cold in the winter time. I posted a question to a Reddit chastity group asking if anyone had used metal cages in colder climates, and if they had any issues. Several people responded bragging about wearing their metal cages in sub-zero temperatures with no problems whatsoever. Most people who responded said that the metal cage would heat up to your body temperature and stay that way until you removed it.

Once I was sure I wanted to go with metal, I started looking at different metal cages until I found a style that I thought would be suitable. I needed something that was going to be comfortable to wear long term, and in public. I had to make sure the ring would be at least as big as the ring on my current cage. It needed to have rounded edges, and leave a little breathing room for my cock, but not too much.

I came across a device that seemed to have everything I was looking for. It was metal with all round edges, and I liked the black. It had good reviews. Most importantly, it looked like it would be a good fit for my cock. I knew I should talk to my Domme before ordering it, so I added it to my cart and saved it for later.


I woke up in pain. All of the sensations I had felt the previous day were intensified. I begged my Owner to let me out of the cage to shower. She said yes, and I removed the cage immediately. Being out of the cage was an amazing relief.

My cock looked fucked up. The outlines of the cage were clearly visible. My cock had begun to swell out through the ventilation holes of the device, which left some odd looking oval shaped protrusions on my shaft. The area around my scrotum where the ring of the device had been was tender, red, and sore.

The shower was nice, and I felt relieved not to be constricted by the device for a few minutes. Unfortunately, my testicles retreated into my body immediately upon exiting the shower into the cooler bathroom air. I had to kneel in front of a space heater for several minutes to get my balls to drop enough to get the cage back in place.

The device was comfortable for about half of the day, then it began to chafe again. I was relieved to be allowed to remove the cage for swim class. When I saw my Domme, I told Her about the pain that the chastity device had been causing me because of it’s grooved ring, and my desire to procure a new cage. She seemed disappointed that I was having issues with the current cage, but was accepting of the idea of me purchasing a new one.

She asked me if I missed jerking off. Of course I responded with an emphatic, “Yes!”

To my surprise She said, “I want you to jerk off before you put the cage back on.”

“Really?! Thank you Ma’am!” I was both surprised and extremely thankful that She had chosen to take pity on me.

“But only to BDSM porn,” She added with a smile.

“Yes Ma’am,” I said, smiling back. I likely would have chosen BDSM porn anyway. I had a nice long jerk off session in front of the computer that night. My vibrating butt plug and Hitachi wand were put to use again, but no cage this time. It was nice to hold my fully erect penis in my hand again. I took my time stroking and watched a variety of BDSM porn. I came hard with prostate assisted orgasm, and shot my load all over myself. After cumming, I showered and locked myself back in the device. I ordered my new chastity cage that night.

6 thoughts on “30 Days of Chastity: Week Two”

    1. I don’t pretend that I know what the future holds. What I do know is that right now I am in love with two very different and very special women that both love me. Despite all of the inherent difficulties of balancing multiple romantic relationships, I am more happy now than I have ever been. I plan to write in detail about polyamory and how it works for these relationships in an upcoming blog entry. In the meantime, I encourage you to educate yourself on the topic. Love can be so much more than what archaic traditions would allow.

  1. Thank you for your entries, as a Mistress I am totally enjoying reading how your owner teases, plays, and toys with you to her pleasure. And to hear your side if this relationship has me blissfully thinking on the thoughts my sub may have.

    1. Thank you for your kind words! I am always happy to hear that my writing is being enjoyed. I know my Owner will be happy too. 🙂

    2. As his owner, I particularly enjoy his consistency—both in terms of pleasing me and being imperfect. He consistently works to impress me and learn from his mistakes. I am proud of him growing into being owned and becoming my primary.

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.

Leave a Comment:

Your email address will not be published. Required fields are marked *