For today’s blog, I’m going to cover all three days together since I’ve fallen a bit behind on posting. Rather than breaking them up, I want to talk about what I’ve been experiencing over the past three days as a whole.
These past few days have been incredibly frustrating—and not just sexually. Getting used to wearing the cage has proven to be a much bigger challenge than I anticipated. My sleep schedule has been all over the place, and keeping up with being caged takes a significant amount of time each day. Between maintaining hygiene, managing uncomfortable (and sometimes painful) sensations, and trying to keep my irritability and emotions in check while my hormones feel completely out of sync, it has been overwhelming at times.
Despite all of that, I continue to face each challenge happily and enthusiastically. This experience is incredibly important to me. It’s something I’m deeply passionate about and genuinely take pleasure in participating in, even when it’s difficult.
One unexpected moment that I would definitely consider part of the chastity lifestyle happened at a dealership. I went to use the restroom while someone else took the stall on the right and I took the left. While I was sitting there, someone suddenly opened the door—only then did I realize the lock didn’t work. Thankfully, my cage was tucked into the toilet. I stood up to wipe and dry when, unbelievably, someone opened the door again. This time my cage was fully on display. I grabbed the door handle with everything I had, my pants around my ankles, and managed to close it before they could see anything—at least, that’s what I choose to believe. It’s hilarious now, but at the time I was absolutely in fight-or-flight mode.
After bidding closed, it was time to submit our edging videos. Wanting to send something high quality, I recorded mine with my Sony camera using an online metronome and a clothespin on my left ball, following the new rules. I got the lighting and angle just right, but completely overlooked one critical detail: the timestamp. I assumed I could add it later using online software, but I was wrong—especially since the file size was enormous.
I spent the entire night trying to convert the file into something playable on a phone or PC while also trying to solve the timestamp issue. I let Mistress Ashley know that I had the video and was working on adding the timestamp. She instructed me to send the video to her directly right away and to post it in the group once the issue was resolved.
When I realized there was nothing more I could do, I took a photo of the video playing on my camera that showed the date and time of the recording. I sent that to the group along with the actual video, explaining that I hoped it would be acceptable. Mistress Ashley accepted it but reminded me that next time the timestamp needs to be embedded in the video itself—which I completely agreed with. I also made it through another edging session without cumming.
Tuesday, however, was a day from hell at work. I was exhausted, grumpy, and extremely uncomfortable in the cage. I could tell my mood was off, but for some reason I just couldn’t turn it around. When I got home around 6 p.m., the discomfort had reached a breaking point. Everything was sore, and upon inspecting more closely, I noticed small open spots and about an inch of rash right where my penis meets my pelvis.
Reluctantly, I reached out to Mistress Ashley to explain the situation. I really didn’t want to leave the competition, and taking the cage off was against the rules, so messaging her wasn’t easy—but I knew I had to. Before doing so, I ordered a skin barrier film online, hoping it might help.
She told me she hoped the barrier film would work and asked what I proposed doing in the meantime. I suggested removing the cage overnight to rest and mentioned that I had found a couple of other cages while going through my secret stash duffle bag. She asked if I could hang on until the next day, explaining that she was okay with me changing cages and resting at night but had a surprise planned and hoped I could hold out. I told her I would do my best—I definitely didn’t want to miss the surprise.
I searched for ways to reduce friction and switched cages. One of the cages I found was a Holy Trainer with what I thought was a larger ring. It turned out the ring wasn’t actually that big, but wearing it felt like heaven. I’ve always chosen my “correct” ring size by measuring around the base while flaccid, but I now realize I probably should have started with a larger ring. The Holy Trainer’s design left my sore spots untouched, and the difference was immediate.
I posted a verification photo to the group and went to bed. That night, I slept incredibly well—even though I woke up a few times from erections. They weren’t painful, just uncomfortable due to the tube, not the ring. That distinction made a huge difference. I was intensely aroused, but without pain taking away from the experience. I found myself humping the bed and letting out quiet, frustrated moans.
I kept thinking about how every time I felt like I couldn’t take it anymore and reached out to Mistress Ashley, I always ended up still caged—and always stronger for it. The way she handled each situation and guided me through turned me on deeply. I felt a profound sense of being owned. Even now, thinking about it makes my heart race.
When I finally woke up, I felt happy and refreshed. I went to work excited, thinking about the surprise awaiting us. Sure enough, at 9:54 a.m., Mistress Ashley posted in the group:
“While we are waiting on results:
Everyone who has completed their submission for this round may take the next 24 hours unlocked.
If you did NOT cum during edging, you may orgasm once during your unlock.
I expect verification of lockup at 10 a.m. CST on 1/22/26.
I will post results when they are available.
Enjoy your break. Hope it helps.”
I was so relieved—even with the new cage. I expressed my gratitude and told her everything that had happened overnight. She replied, “It sounds like you are enjoying this—frustration of the best kind. I’m glad the Holy Trainer was more comfortable for you.”
After that, I spent the rest of the workday getting used to the Holy Trainer. It was comfortable for the most part; I just need to get a harness to keep it closer to my body.
To be continued…