I’ve started a new relationship and feel it’s the perfect moment to start journaling. Welcome to my bizarre sexual adventures.
First, let me share some background on past experiences as an introduction and to set the stage for what’s happening now.
Before I even knew chastity devices existed, I had been interested in them. I’ve always possessed a deep urge to please women unconditionally. As my teenage mind realized there are limits to how happy you can realistically make someone else, unconditional sacrifice became the new goal. I learned to give up my dignity first, planting the seeds of a humiliation fetish that remains with me today. Then, the internet introduced me to chastity devices when I was in my mid-teens. Since then, I haven’t found any better way to satisfy my deepest desires (with just a touch of humiliation now and again!) than by offering myself to a woman while wearing her device.
My first try at bringing chastity into a relationship was a disaster. I was 25, dating a very possessive girlfriend who was only nineteen. She felt terrible about being so controlling, which made me think chastity would be the ideal fix. When I brought it up, she agreed to give it a shot but wasn’t really keen on it. That’s when I realized that if my partner didn’t genuinely enjoy locking me up, I wouldn’t either. In the end, I decided against ordering the device, and she never mentioned it again during our time together.
Four years later, I entered a fast-paced, roller-coaster relationship with an 21-year-old woman. We were madly in love. I introduced her to the kinky side of sex, which unleashed the wildest sexual partner I’ve ever had. A wickedly playful Domme emerged within me—someone who loved inflicting pain and humiliation. From day one, we were incredibly open with each other. I believe I mentioned chastity during our very first time together, and before long, I’d ordered a device and started wearing it 24/7.
My routine shifted from having sex almost daily to being completely cut off, receiving hand jobs just four times a year. I was cuckolded by four or more men, received regular whippings, and had all my darkest desires met. It was intense!
We stayed together for about three years before parting ways, but we remain close friends who hang out every week.
Throughout it all, my friend G (let’s call her that) has been a steady presence as both a confidante and companion. At 25, she has exclusively dated women since age 17. We’ve navigated through her various relationships over the past five years together, so we know each other well.
When we met for coffee on a Saturday about three months ago, I had quite a juicy story to share with her. To make a long but worthwhile tale short: that week, I discovered not only could my neighbors see into my room through their windows, they were also using cameras to watch me. If those cameras have been there as long as they’ve been able to look in, then they must have seen absolutely everything.
It’s a student house; I believe four girls live there who seem to share either their views or videos with quite a few people. For someone with kinks like mine, this situation seemed too good to be true. Of the three people I told (two being my former Mistress and best friend), G showed the least amount of abject horror at my predicament.
She asked me what I planned to do about it. I had been contemplating options while purposely maintaining my habits to preserve the illusion that I was oblivious.
Initially, I thought moving might be wise, but once the initial shock wore off, I reasoned they’d already seen everything—seen me naked countless times and in much worse states than usual. I felt like there wasn’t much left for me to be embarrassed about, so one night I purposely slept above my covers with my chastity cage visible, sealing my fate.
To complete my nihilistic free fall, I told G that I intended to make contact and suggest they blackmail me for the key to my cock cage instead of sharing those damning videos further. I thought they might enjoy controlling when and how a man performs for them through open curtains rather than waiting for me to act (admittedly, they could easily spot patterns in my daily masturbation schedule).
G called it a crazy idea! She begged me not to go through with it. I was listening, but it was such a strong fantasy. The notion of having the keys posted back after weeks or longer of denial by those student girls across the road repeated in my mind as I slept, adding an incredible rush from the possibility that they might be watching me at that very moment.
After coffee and chatting for a few hours, G and I parted ways for the evening. When I got home, I received a text from G saying if it would make me happy, she would hold the keys to my cock cage. I was delighted, but replied that I’d only truly enjoy the chastity if she enjoyed having the keys in some way. She said locking me up seemed kinda funny… Good enough for me! I asked G to send a padlock without the keys enclosed.
Four days later, delightfully, a parcel arrived containing a small but sturdy brass padlock with no keys inside.
I informed G that I’d received her package and would lock up at midnight. I retrieved my cage and prepared for what lay ahead. G lives 15 miles away from me; we see each other about once every two weeks due to our schedules. Once I clicked the steel device shut, there was no easy way out—at least not immediately. Interestingly, I hadn’t even discussed with G how long I’d be locked up!
Before too long, these thoughts sent blood rushing from my brain to my penis as I counted down the minutes until being locked up with lustful anticipation.
G had said, ‘One last wank before you go?’ when I told her I was ready. So at 11:55, I took one final explosive wank over the fact that this was indeed my last chance to decide when I cummed before G’s padlock secured my cage forever.
Even just knowing that G was considering how often I should cum was pushing me over the edge. As pearls of semen left my body in spurts and sexual energy began to fade, I decided to fit the cock cage as quickly as possible so as not to give myself time to chicken out.
I hesitated for only a second with fingers on the lock, then without ceremony pinched it closed with a definite ‘click’. I had passed the point of no return. Now at the mercy of my lesbian friend G, with no other means to orgasm nearby, I soon felt the confines of the cage and that all-too-familiar squeezing of my member and pulling of my balls. The rush of being back in chastity from that moment is still vividly present.