31 Days of Chastity Meme Day 5: Your First Time

As I shared in yesterday’s post, I engaged a pro keyholder for my first chastity experience and she led me through a 30 day “Chastity Bootcamp.” I had already ordered my first chastity device but hadn’t yet received it when I reached out to her and we made our agreement. The very day the device showed up in my mailbox, per our arrangement, I texted her to let her know I was ready to start.

For those who are curious which device I wore for the first time, you can see it by clicking on the review I posted on the Jailhouse. When I bought the device, you can believe I knew close to absolutely nothing about chastity devices. I chose it because I was familiar with CB devices and essentially the Jailhouse is a stainless steel copy of the CB-6000 with the split base ring, locking pin, and spacers. This turned out to be a horrible device because unlike the plastic CB-6000, it came with only a one size fits all locking pin and a single pair of spacers instead of a variety of those parts designed to give the wearer something close to a customized fit. Frankly, my first time wearing a chastity device turned out to be a comedy of errors.

As soon as I let my keyholder know I had the device in hand, she told me to put it on and to send her a photo. I found it easy enough to put on, thanks to the split ring, and after locking the padlock supplied with it, I took the requested photo with my phone and sent it at around three in the afternoon. As soon as my keyholder saw the photo, she texted me and said she doubted the device would work, enumerating her reasons. She could tell by the photo that it didn’t fit me well. But she told me to wear it the rest of the afternoon and then to remove before I went to bed.

Less than fifteen minutes after I put the device on, my left testicle popped out of the base ring. Since I wasn’t yet using the plastic numbered locks that my keyholder would eventually have me use, I unlocked the device, removed it, put it back on and relocked. That time it took about twenty minutes before my testicle popped out again. I couldn’t understand why that was happening, so I contacted my keyholder again. She told me I needed to try different pins and spacers until I got a fit that didn’t allow my testicle to pop out of the base ring. When I told her the device came with only one pin and one pair of spacers, she told me the device definitely would not work because the gap was too large for me and I had no way to correct it.

No, I did not know what “the gap” was, but felt satisfied she knew what she was talking about and we both agreed I needed to find and order a different device. I chose one, a simpler stainless steel device available on Amazon, mostly because I knew it would arrive in two days and I was eager to get started. Until the new device arrived, we made do with the crap jailhouse and I lost count of how many times I had to remove it and put it back on when my testicle escaped again and again. She actually thought it was all quite funny, but it didn’t feel that way to me and I was so embarrassed by having chose such an awful device.

To my relief, the new device, another cheap made in China stainless steel device called the AO86, arrived two days later. Not understanding what “the gap” was and unwilling to ask my keyholder to explain because I already felt stupid enough, I had decided the problem had been that the Jailhouse base ring was too large for me even though the size I had ordered with it agreed with the measurements I had taken. So, without consulting my keyholder, I ordered the AO86 with a base ring that was 5mm smaller in diameter than that supplied with the Jailhouse. Another rookie error. But at least when I put the device on, my testicles remained trapped. So, I could wear the device for the periods of time my keyholder wanted, but the base ring was too small and produced a lot of discomfort I shouldn’t have had to endure.

I was excited about beginning chastity, but frankly, because of the discomfort, I was always happy to take it off before going to bed each night for the first few days. My keyholder wouldn’t let me sleep in it until she felt certain I wasn’t having any impaired circulation issues and being very knowledgeable and experienced knew my body needed time to acclimate to having a hunk of stainless steel locked on my genitals before I could wear it for long periods without having chafing and soreness. Finally, on the fifth day, she told me to sleep wearing it for the first time and I felt overjoyed.

Yes, I had the same experience as most every other guy who has locked on a chastity device for the first time, with uncomfortable attempted erections waking me multiple times during the night. I didn’t know it then, but the inside diameter and length of the cage was bigger and longer than my flaccid size, and that made the nocturnal erections (with ample space to grow) worse because the cage didn’t immediately suppress them. That lasted for about three nights, and then either the nocturnal erections stopped or else stopped waking me.

I can’t recall for sure how many continuous days she had me wearing the device 24/7, but I know sometime during the second week, she made me remove it before bedtime one night to allow for normal nocturnal erections. Once I put the device back on the next day, it was on baby and I wore it 24/7 for the rest of that first month except for the two releases my keyholder gave me. I stayed locked for eight days in a row before the first release. My keyholder said, “we need to check the plumbing and make sure everything is still working as it is supposed to.” She told me to unlock and to masturbate until I edged, then to continue stroking, just until the moment I felt myself slipping over the edge and passing the point of no return where orgasm was inevitable. When I reached that point, she told me to stop stroking, remove my hand, and to “ruin” the orgasm.

After eight days locked, I didn’t need to coax an erection. Things were already firming up nicely by the time I got the cage and base ring off. I had experienced ruined orgasms before, so I already knew how it was done. I followed my keyholder’s instructions. Once I felt myself approaching and slipping past the edge, I stopped the stimulation and the semen dribbled out pathetically. Satisfied that “the plumbing” still worked, she gave me twenty minutes to shower and clean the cage and then I relocked, this time with a plastic numbered lock.

After relocking, I furnished daily proof of lock photos, but my keyholder didn’t supply any teasing. It was only straight denial as she focused only on getting me accustomed to wearing the device 24/7. I didn’t find it difficult since I was so stoked about experiencing chastity for the first time under the supervision of a dominant woman.

Before the end of of the month-long boot camp, at my request, we had already agreed to her remaining my keyholder indefinitely, so I stayed locked for 18 days after the ruined orgasm until she gave me the next release, this time a full orgasm. I was eager for the orgasm, but to my surprise afterward, I felt empty and depressed. I even felt I had failed her by having the orgasm and just felt generally weird about it. She was terrific with aftercare and shepherded me through those unexpected and intense feelings, which she told me were all very normal for someone experiencing a lengthy period of orgasm denial for the first time.

And that’s how my first time in chastity went, how long I remained locked, and what happened on my release. I continued with my first keyholder through the end of the second month, through the third month, and into the fourth month. By then, she had kept me locked for almost sixty days without a release. She was teasing me regularly by then, which made the denial far more difficult to cope with. On my sixtieth day of captivity, I had had enough. She was a terrific keyholder, and I really liked her, but she had overestimated my readiness for permanent chastity. I texted her I was quitting, cancelled our agreement, unlocked, and had a good wank. And that time, I felt only relief, no depression.

More than once, I’ve regretted quitting and losing a really wonderful, experienced keyholder. Frankly, I never had another keyholder who came close to my first one until I met Lucie. I feel pretty sure Lucie has permanent chastity in mind too, even though we haven’t discussed it. But that’s okay because I’m a different man now with a lot more experience and I believe I’m ready for permanent now. Especially with the amazing woman who now controls the keys.

If you’re enjoying the 31 Days of Chastity Meme series, be sure to check in tomorrow for Day 6, when our topic will be fantasies. I will respond to this prompt:

Describe your weirdest/most interesting Chastity fantasy.

Until then, stay strong. Here on this fifth day of Locktober, things should have begun to feel a little easier. And by this time next week, those who persevere should find themselves squarely in the “Goldilocks” phase when they will be well on their way toward completing a successful Locktober 2023.