My journey began with a dare.

In October 2019, I was a member of the website Tumblr. I followed a few blogs about classic cars. I met and chatted with a guy named Jeff that was restoring a car. Occasionally his wife would log on and chat. I discovered they live in an FLR. It was explained to me what that entailed. I continued to chat, following the progress of the car restoration.

One evening, his wife got me into a discussion about chastity. I learned that night how important chastity was to their relationship. She kept her husband locked 24/7. I could not understand how someone would do that. I laughed, thinking about how people might choose to explore chastity. The wife (let's call her Sandy) gave me a challenge. She said I couldn't judge the actions without knowing firsthand for myself.

In my weakness, I took on the dare. She told me to buy a chastity device and follow a schedule for seven days. Once I completed this, we would chat about it.

Schedule:

Day one: two-three hours locked at home.

Day two: three plus hours and out running errands.

Day three: wear to work and try to last half the day.

Day four: all day at work.

Day five: wear it when I sleep.

Day six: keep it on for half the night.

Day seven: keep it on all night until after my morning shower.

I took this dare, not thinking where it could lead. it just was a dare that I took on for kicks and giggles. I knew I would spend a little money on the purchase of this device. My time fooling around with the cage would occupy my time. I was single and so no reason to worry about being discovered. I think I was a little bored and needed something.

I found a lot of variety in cages. I was concerned about the bulk of the padlock, showing through the clothes. I found a modern cage that I liked. The cage was controlled through a phone app. I purchased the cage arriving about a week later. I may have spent the day, trying to figure out how to get it on properly. I was ready to start this challenge.

My first day was nothing. My second day made me nervous, but that feeling disappeared. I left for work on my third day and felt confident. If I had run into trouble, I had my phone removed from the bathroom. Only at Lunch during a trip to Home Depot did I get scared. I walked out the doors when the alarm beeped. Luckily a customer had a purchase that triggered the alarm.

Now, a full day at work was more difficult. I wore my cage for ten hours. My erection was building, which made the situation awkward. A couple of nights of trying to sleep was the worst. I felt the cage on and just couldn't fall asleep. The third night I was tired, and I fell sound asleep with the cage on. The incredible pain in my groin woke me. I had morning erections contained in my cage. The throbbing pain was intense. However, I had rules to follow and couldn't just remove the cage.

I jumped into the shower and started to clean up for work. My erection subsided, and so did the pain. My schedule dictated I wear the cage to work. I chose not to remove it. Strangely I felt a sort of euphoric feeling. A few hours later I was at work and standing at the urinal. I was still wearing the cage and never took it off. I entered the stall at this point.

The following day I logged on and sent a message to Sandy and her husband. I did not get a response for over a week. Once I did get a response, it was simple. My message read, hello little fella. I learned they were on vacation and are now back at home. I responded by asking about the last text. Was it meant for someone else? Sandy typed back and said the message was for my penis. I laughed online about it, telling her that it was funny. Then Sandy told me not to laugh. Then sent me a question and wanted an immediate answer. "Are you wearing your cage right now?"

My heart raced, and I started to sweat, feeling very confused. She sent another message, telling me not to make her wait.

Online my embarrassment was not showing. However, my screen was blushing. The next week my cage was on and off. I was currently wearing it and almost forgot about it.

"YES," I typed.

It felt like hours before she responded, only a minute or two. She typed her message, "Good Pet." Her comment made me feel aroused. I enjoyed being called that name, by a stranger. I looked at my aroused cock sitting inside the cage. The cage stayed on from that moment on.

We didn't chat for a while after that. It may have been a month or two since we spoke. Sandy's husband had just finished painting the Camaro. He knew everything that had gone on and gave me some advice. Go in search of a Keyholder and give over control. I was shocked by the advice she gave me. She warned me to be careful and chat and get to know the person before giving my key to someone.

My search was about to begin. My profile changed on Tumblr. I began to follow chastity and Femidom blogs. Very quickly I found my inbox filled with supposed mistresses that wanted to play with me. I was surprised at all the different fetishes that were listed. This newfound interest opened my mind up to so many new things.

One night I chose to seriously look to find someone that would teach me, and take my key. It was not going to be a quick or easy decision. In the following ten days, I was able to cut my list down to three possible mistresses. The day I made my choice. I was speaking to one I didn't choose. I told her the truth, that I am selecting another. She seemed to be sad and re-confirmed the warning. She told me to be careful and not get hurt. What she meant to say is not to get scammed or blackmailed.

I was a novice and ignorant.

I would soon learn.