Locktober 2025 Chastity Cage Guide：My First-Time Journey & Tips for Beginners

Locktober is a widely known internet challenge in the crossdressing, sissy, or femboy community. I’ve known about Locktober for years; in the past, I found it amusing. I wondered why anyone would do such an absurd challenge. However, I’d recently had a change of heart. Summer 2025 involved taking some big steps forward as a crossdresser; experimenting both with fashion and pleasure, I managed to get more in touch with myself.

Part of my summer experimentation was to wear a chastity cage for a few days. Since this was a positive experience, and October was approaching, I decided to attempt the challenge. I was curious to see how an extended period would affect my mindset. It was certainly an interesting experience for many reasons. I’d like to share a bit about my Locktober 2025.

Starting Out

When I decided to take part in Locktober, I spent some time ruminating on how to do it. Most participants seem to take it to quite an extreme, and not remove their chastity cages for much more than daily hygiene. As an inexperienced user, I wasn’t sure this would be realistic for me. Also, I felt it wasn’t appropriate to bring my sissy or sexual thrill to work.

I began to think in terms of more positive goals or principles to follow as opposed to making restrictive rules for myself. Sometimes framing things as goals or stars to shoot for can be motivating. Moreover, because this was going to be a longer-term lock-up, I felt that having daily, weekly, and monthly goals for the month would press me more to look past short-term impulses.

My positive principles for Locktober 2025 were relatively simple. From the evening of October 1st, I’d endeavor to lock up my sissy clitty each night until morning. I could be flexible with sleep as long as I tried it with the cage on each night. Days off work would be spent locked up, and going out meant being locked up in some boy’s clothes. Each week, I’d try to spend at least 2 days in my full femme persona at home, dressed up with girly brain activated. And finally, there would be no pleasure seeking through my sissy clitty, any sexual pleasure to be found would be found with the cage on.

The last and final goal was to have the elusive sissygasm. I had seen clips online, and the expression of the sissies led me to believe that they were experiencing a feeling I had never had. I didn’t know how, but I resolved to try and make it happen.

First Weeks

With my rules in place, I took the plunge and locked up on the evening of October 1st. It was a Wednesday evening, and for most of the first few hours, I didn’t notice it much. For the next two days, I locked up my sissy cock in a metal cage in the evening and would take it off in the morning. The first Weekend was much the same; I’d tried wearing the cage for a few days at a time, so I wouldn’t be broaching the unknown for a few more days. Generally, I felt calm and at ease with myself.

As more days began to pass by, I got closer and closer to my previous maximum time in a cage, which was about 8 or 9 days. When I got to October 7th, I began to get the feelings of frustration that come with being in chastity that many sissies adore. I also felt more and more committed to my goal of making it through the month; the frustration led to motivation to be a better sissy and try new girly things.

The first two Locktober weekends were spent locked without interruptions for the most part (other than showers). I began to notice that I would take more time browsing shop windows and dressing myself mentally in new outfits. Of course, I bought some new girly clothes, and each Sunday afternoon, I would have a lovely little mirror fashion show.

Also, with each passing day, I began to feel bolder and more daring. Posting photos of my outfits, joining locktober group chats & having flirty conversations online. The validation a sissy can find from some anonymous flirtations; being addressed and treated as a delicate, feminine girly is super affirming.

Last 2 weeks

I passed my personal best time for being a locked-up sissy on October 11th; each day after that was a step into the unknown depths of chastity. Entering the 2nd half of the month, I was feeling quite proud of myself for sticking to my principles. I found it easier and easier to get into a more femme mindset instinctively.

As I was now stepping into the unknown, so to speak, I began to look for more ways to upgrade my sissiness. By far the most affirming was to speak with other sissies and Locktober participants online. Joining a group chat with other girlies who were also locked was a great decision. We were able to keep each other motivated; when sharing experiences or pics, the compliments and positivity would bring on a feeling of feminine glee. It was so lovely to talk to other girls from around the world.

Now, as I’m sure you’re wondering, it was very easy to get lost in frustration and arousal because of a lack of release for such a long time. Chats would often turn steamy, and then my thoughts would wander to what other fun activities I might be able to get up to. I had been trying to be a good sissy and not unlock or have a traditional male climax during the month. Many sissies report that being in chastity can make them feel submissive and more open to suggestion. I hadn’t felt this, but had definitely had a more girly brain.

However, one simple addition to my evenings changed that. Eventually, curiosity, frustration, and desire overcame me, and I had to play. I didn’t want to climax as I usually did, but as a sissy. After sixteen days of being locked up and minimal sexy play time, even my smallest sissy toy began to drive me wild. The feeling of being locked up in front and plugged in the back sent my brain into a spiral of submissiveness. From the moment I popped it in, there was a near instant change, and I suddenly understood the submissive mindset that I’d read about.

When IT happened

I had been curious about the sissygasm for a while. I’ve always been curious how it feels to be a woman in bed, to be penetrated, and the seemingly more intense, longer-term pleasure women get. With my small toy inside me, I could feel waves of arousal and pleasure that must have been similar to it. Thoughts of being treated like a girl, and experiencing a more feminine pleasure filled my mind when I’d add my toys to the locked setup.

The sissygasm happened on a Friday. My level of horniness had reached a point where I needed to have a release. I resolved to try not to stop until it happened. I guess for each girl it’s different, and I needed to understand my body a bit more. But through an evening of joyous and semi-torturous exploration, I was able to find a way to have my first sissygasm while locked in a cage. I can report that the feeling wasn’t as powerful as I had anticipated, but the buildup beforehand and come down afterwards were the real experience. Building up to sissygasm was one of the most intense pleasures I’ve felt; every step up in intensity didn’t bring on tiredness, but a need to try harder. After that evening, it happened again the next evening. And again, the next. 

Reflection

Now it’s been about a week or two since the end of Locktober. I’ve been thinking back on my experience with fondness. I wasn’t able to complete the month for professional reasons; I was sent to a meeting out of town and couldn’t go caged. All in all, for me it was about 26 days locked. I managed to gain a lot of confidence in my femme self in the process. It felt nice to engage with my girly side on a regular basis. Adding the element of only girly-style sexual fun, even if just home alone, was a very pleasurable new element I’d not had the gumption to try before. I felt like I’d made progress getting to know my girl side, I’d learned more about my own body and how I can manipulate myself to find fun in new ways.

On the other hand, there were difficult moments as well. Sometimes doubts about possibly impacting my sexual health would crop up from time to time. Every so often, a bit of a cringey, ‘what am I doing?’ feeling would pop into my head. Lastly, though, I think I may have overdone things in my final week. I had found the sissygasm in a way, and while it was lovely, having them a few evenings in a row may have been a mistake. Each one was a bit less intense than the previous one and harder to achieve. I guess this is normal, much in the way that the first bite of an ice cream sundae is the best, and too much of a good thing makes it a lot less exciting. When I got to the end of my time, I was happy to return to a freer existence. I was proud of my experience, too.

Conclusion

It’s been a few weeks since I unlocked and returned to normal existence. While I’ve not been locked up or dressed up much since the end of my first Locktober effort, I’ve been thinking about it a lot. I was able to get in touch with something that I hadn’t before. I’m looking forward to the next chance I get to spend a prolonged period in girly sissy mode.

Sometimes I’ll find myself scrolling through some of the many photos I took of myself during Locktober, lying in bed before sleep, perhaps having a moment of contemplation with a cigarette. I certainly value the memories and feelings that the month brought up. Aside from the fun I was able to discover by treating my body in a different way, I have reminded myself that I’m capable of taking on a little project and pushing forward with it.

I’ve already started mentally planning for the next time I’ve got an opportunity to have a semi-prolonged locked sissy time. I think I’ve found a window, so stay tuned for updates.