- Upton Rand
- May 6
- 8 min read
Updated: May 11
Ever wondered what it’s like to put your dick in jail and throw away the key? Spoiler: It’s a wild ride. If you’ve never heard of male chastity devices, the idea is pretty simple. It’s a device that encloses the male anatomy, is rigid, and typically prevents the wearer from achieving an erection. Until recently, I’d had some exposure to these devices but never really dove in for an extended stay. It’s often tied to the BDSM community, but in recent years chastity has seen substantial growth in the gay community—all kinks have! That’s why I write about them so often; they’re really fascinating.
In this blog, I want to tell you guys about my outrageous experience wearing a chastity device for a week. I won’t be the last to wear one of these devices, and I’m certainly not the first. If we’re looking at male chastity and want to get an idea of where they come from, we have to take a little trip back in time. All the way back to 15th century Florence. In this time period, the first fully illustrated manual of military technology was released, called the “Bellifortis,” meaning “strong war.” Written by some old perv named Konrad Kyeser. ;-) While this book didn’t exclusively cover male chastity, it is the first major mention of it in writing. Male chastity in these times was built for function, not a Saturday night at the bathhouse. They had a band extending around the wearer’s hips and a shield covering the dick and balls. They were essentially jockstraps of the early Renaissance period. Things have come a long way since the “Bellifortis” was written! Modern devices are a reclamation and modification of these early devices. They’re lighter, breathable, and designed for everyday use.
So how did this curious cock cage challenge start? I’d seen these devices periodically. I’ve been in situations where men will wear them for a variety of reasons. Most recently, it was around a group of men in an athletic setting. I took a class on nude meditation. There were about 12 men there, and 3 were in chastity devices. It’s too early for math, but I do know that’s over 20% of the guys. This wasn’t really a story though; I was more interested in the why. Flash forward a few months. I’m at the gym doing curls on a bench with dumbbells when I catch this dude’s chastity cage slipping out his shorts a few benches down in the mirror. As he was doing bench presses, it had inadvertently slipped out of his shorts. It was a bright metallic cage. It’s like a shiny little middle finger to my workout focus, glinting all, “Hey, check me out.” I’m just staring, weights forgotten, thinking, “What the hell is this?” I will say this was a gym in Lakewood, a notorious gay neighborhood in Lakewood. I’m not sure if you’d see this at a small-town YMCA, but who knows!
My next exposure was when I roll up to Horse Market, that gay kink fest I wrote about; you can read about it here. I’m not always down to clown, but damn, the energy’s wild at a place like Horse Market. Dudes in cages during that event were strutting like they’ve got the keys to the kingdom, tossing flirty looks that scream, “Good luck unlocking this.” Chastity’s clearly the new hot shit in the queer scene, and I’m like, fuck it, I gotta try this. I made a decision at that event that I was going to try it out.
I hit up my buddies, this couple who basically live for kink, and I asked them about these devices. I knew they were both wearers, as well as customers of Gay Men’s Field Guide, having picked up a couple of my hand-drawn Tree of Life shirts for Pride. (Shout out to Sean and David—thanks for helping me keep the lights on and supporting the guide!) I explained my particular curiosity about them. Since I split from my husband, I’d had difficulty achieving erections with strangers. It’s not that I don’t enjoy sexual experiences; I just enjoy them more when there’s a strong connection. Unfortunately, until I find Mr. Right, that’s not always possible. The appeal of chastity for me was being able to be with another man and take this stress of performing sexually off the table. Many tops accept chastity devices on a bottom unquestioningly. It sort of says, “You can enjoy my body, but the dick is off limits.” Which seemed extremely appealing. Kind of ironic that I was seeking to free my mind by locking myself in a little dick jail—lol. They invited me over one Saturday for a visit and a fitting. They were kindly willing to lend me one of their devices. As I walked into their bedroom, several devices were laid out on the bed. Some black, some plastic, some metal. It was like a whole wardrobe for my dick.
I stood there, unsure of where to begin. Sean approached me and pointed at a small black device, saying, “This is the one I wear.” He pulled down his pants, revealing it fit snugly around him. A woven black plastic cage encased his penis, protecting it like the ones I’d read about in the Bellifortis. His testicles were trapped through a loop and swiveled freely. Each device had three components: a loop through which the balls and penis passed, a hard sheath that the penis slid into, and a prong that aligned with the cage and loop. Once the penis was fully inserted, a small padlock was inserted and locked, preventing the user from removing the device without the key.
Sean gave me a quick rundown on putting on these devices, and before I knew it, I was front and center, in some strange dick fashion show. The first cage was way too small, and my junk was like, “Nah, fuck this.” The next one was so tight it was trying to murder my soul. After a lot of lube and some adjustments, one finally fit, and I was strutting like I just aced a drag audition. My friends were losing it, cheering, and for that afternoon, I’d become kink VIP. They were also kind enough to give me some very high-end hand-me-downs for my trip to Freedom Valley on leather weekend, the location and weekend I wrote a lot of my 3rd book, Gay Campground Revisited. Available now in the store.
But getting that cage on? Holy shit, it’s a nightmare. It’s like trying to shove your balls through a keyhole while your dignity’s screaming, “Abort!” You have to slide one nut through the ring, then the other, like you’re playing Operation with your own balls. Then you stuff your dick in the cage, which sounds sexy but feels like wrestling a pissed-off snake. The worst part? Lining up the cage with these two prong holes to lock it. Those prongs are straight-up evil—pinching skin, ripping hairs. One bad move, and yank, there goes a patch of pubes. I’m yelping, half-lubed, half-ready to quit, wondering if I’m gonna end up on some kink blooper reel. As I lay on their bed, Sean and David were coaching me as I spent around 20 minutes getting the hang of it. They watched on, guiding me on what to do next.
“Ok, now tug on your balls, and slowly slide the head through.” “Gently slide the prongs in, while clearing any hair in the way.”
I felt like I was getting instructions on baking a cake.
Finally, I was locked in. I just slammed my head into their pillow, exhausted, needing to catch my breath. David gave me a waistband that secured to the side of the ring and ran around my lower back, offering additional support.
I got a little cocky and wore the cage to work the next day, thinking I was some kinky badass. That was a huge mistake! Picture me, a grown-ass man, waddling like a penguin to the bathroom, praying my ball doesn’t stage a full prison break. I was in my workshop, trying to cut through a steel plate, when I shifted and—pop—one ball slipped out. I was dying, sweating profusely like I was in a sauna, and clenching my jaw so hard I could crack a walnut. My boss was droning on about blueprints, and I was praying nobody heard me dying inside as my testicles were squeezed apart, one in the ring, one not. It felt like a vice. I was side-eyeing the bathroom door, ready to dash in there. I took a quick bathroom break to readjust the device, much faster than my first time! Once adjusted, I managed to survive.
I felt like a locked-up rockstar over the week. It seems like the more I wore the device, the more comfortable I got with it and the easier it got to take it on and off. It’s definitely tricky to get the hang of, but once I did, there was just something about it. I wore it in all kinds of places: walking my pug Max down the street, in press interviews, I even wore it to my doctor’s office LMAO. I went to get my PrEP shot recently, and they give me the shot in my butt. As I dropped my pants, I can’t help but feel like the nurse saw it but really didn’t know what to make of it, so she didn’t say anything at all. In reality, the lighter the device, the easier it is to do your daily activities in it. Through late-night coding sessions in JSON, Upton’s language of choice, to recovery meetings. The device mirrored my movements for a week. Once I became accustomed to it (which takes time), it became something I didn’t even think about.
Sure, the prong-pinching and rogue hair issues are unpleasant, but the rush is worth it. It’s all about trust and control, whether you’re giving it to someone else or, like me, claiming it proudly for yourself. Whoever holds the key holds access to that part of your anatomy, which is significant. Human sexuality is deeply ingrained in our DNA; it’s the reason for our survival as a species, but it can also be incredibly stressful in the modern world. I wouldn’t say I’m addicted to chastity, but I can certainly understand its appeal after walking that path for a week. For couples who explore chastity together, there’s a certain dynamic of control involved. For individuals who do it alone, there’s another dynamic of control. It’s not about completely locking away your body; it’s about owning it and choosing who to share it with. Call me crazy, but I believe that’s incredibly empowering. Since starting this blog, I’ve come across several gay couples who practice chastity. It’s gaining popularity, and after this week, I can see why. It’s a constant reminder of possession and control, which is at the core of BDSM for many. For me, it was a way to separate the stress of sex from my anatomy.
After my marriage ended, I transitioned into demisexuality (read more about it here). To get really into a guy sexually, I have to know them and trust them now. That wasn’t always the case, but it is now. That doesn’t mean I don’t enjoy being close to other guys sexually; I just don’t always orgasm. Chastity allows me to enjoy time with other men naked, without my anatomy being a factor. To me, they’re a shield against judgment. I wear them in the spirit of the soldiers of Florence in the 1500s; they’re armor for me. Perhaps the Bellifortis in 15th century Florence was onto something!
There are numerous ways to feel free, and for many, this is just one. This week has been both enlightening and surprising. I changed my entire perspective on chastity. I had always assumed it was something negative or cruel, but I understand that for some, it can be a form of kindness. While for many, like me, it’s a way to reclaim control over our bodies, regardless of the reason. I leave this experience with a deep respect for this kink.
Chastity offers a unique blend of control, sex appeal, and, if you’re fortunate like me, even the opportunity to participate in “dick fashion shows.” I gotta admit, these devices can be challenging to size correctly. If you’re considering getting them, I highly recommend seeking help from someone who can assist you in finding and sizing the right ones. They can be quite tricky to work with. If you haven’t tried this kink, give it a shot!
![Are your friendships one-sided? 🤔 Upton Rand explores skewed transactional & "Vampiric" relationships. TRIGGER WARNING: Includes discussion of rape. Read more: [=] #friendship #toxicrelationships](https://static.wixstatic.com/media/d5b722_1eb5bffa6e1c40038ba766f1d0019e6c~mv2.webp/v1/fill/w_800,h_800,al_c,q_85,enc_avif,quality_auto/d5b722_1eb5bffa6e1c40038ba766f1d0019e6c~mv2.webp)
