Sissy Chastity: A Guide to Locking Up for the First Time

Introduction: Why I Tried Chastity

Lately, I’ve been looking for a push forward with my girly side. For me, dressing up at home has become routine. There’s always a bit of femme in my clothes at home now, even if I’m having a lazy day.

It’s always nice feeling a bit femme, but getting fully dolled up it’s a hassle sometimes.

I’d been looking for ways to intensify my femme mindset while just hanging around or seriously boost it when putting in the effort to go full glam.

I’ve been reading about chastity online for a little while; browsing reddit forums to read about different sissy’s experiences.

I heard about ‘Locktober,’ a challenge where sissies keep their equipment locked for the whole month of October; I grew curious.

Internet content being what it is, I took entries with a grain of salt; each account, from femboys, sissies, subs, whoever was all perking my interest.

People were reporting how being locked up made them feel more feminine. Some said it was because their cock was now out of sight and out of mind. Some others claimed that because they couldn’t use it, their male sex drive decreased, and their feminine urges increased.

I decided to try. For me, dressing is about being the prettiest girl possible, and I still want to feel girly, even when I don’t have the time or energy to do the full transformation. I wanted to know if it would make me feel that way, too.

Preparing for My First Chastity Experience

I ended up impulse-buying a cage online, a pink one that I thought was cute. I’ll admit I should have done some more research and perhaps done some measuring of things before clicking the buy button.

I had it sent to a dropbox for pick up to be safe. I opened the package and looked through the contents. I got excited that I was taking a new step in my crossdressing journey and moving forward with myself.

From what I had read, chastity was going to work best for me as a longer-term experience.

Some girls online said they wore it only during play to enhance the pleasure or for short bursts while doing a task, but the feminizing effect I was hoping for would require more time. I wanted to reinforce a feminine mindset.

I wanted to take the approach that if I couldn’t use it, it wasn’t a dicky; it was a clitty; also I would have to sit to use the bathroom with it on.

My First Time Wearing a Chastity Cage

The first time I tried wearing my cage was an evening after work. I came home, showered, and decided to try it on. It took a bit of effort, but I got it on and locked myself up until bedtime as a little trial. It wasn’t uncomfortable, and I didn’t feel any pains or pinching, which would indicate wearing it was constricting blood flow or anything. I tested the lock a few times and felt more at ease about trying this for a longer amount of time.

The day I decided to try to stay in chastity all day for the first time started off quite normally. I woke up and had my morning coffee as usual. As I stood sipping on my warm coffee I was contemplating what I was going to do and if I would make it to the end of the day.

It was about 10 am and I wanted to get to bedtime, or at minimum stay locked for 12 hours as a first try. I went to take a shower, bringing a razor along to shave and make sure I was nice and smooth to feel as girly as possible.

When I finished my shower and it was nice and dry, I picked up the cage to put it on. It’s easy enough to do, but I had some trouble making things fit properly the first time. Using a tiny bit of lotion helped things to slide snugly into place, and I turned the lock and removed the key. I looked in the mirror and it felt cute to see that my formerly boy bits were now contained inside a little pink cage. It’s interesting to feel, too, that a sensitive area is suddenly semi-immune to touch.

I got dressed for the day, and as it was a holiday and winter, warm clothes were called for. I was planning on spending most of the day at home, but I had to go out for some shopping.

Panties are the norm for me, so I slid on a pair of Brazilian-style bikini panties and a cute camisole for under my winter clothes.

I immediately noticed a rather practical problem. The bikini panties were a low-rise style and there wasn’t enough panty to stay in place on top of my cage. It kept slipping to one side or the other; fine for 2 minutes but it felt a bit weird to have my panties bunched on one side of my cage. I switched to a pair with more coverage, a lacy brief with a higher waist that quickly solved the problem.

Going out didn’t feel odd to me; I wasn’t nervous or anything. I knew I wasn’t going to be discovered. I was conscious of my cage the whole time, though. It definitely reminded me that my clitty was small and tucked away the whole time I was out and about.

I wanted to walk around as well because I had left my key at home. The farther I walked away from home, the more I felt a little flutter of excitement that my confinement would continue as long as I was out; no keys, no unlock.

I spent about two or three hours walking around town. I wasn’t outwardly dressed as a girl, but underneath it all the cage kept me mindful of my place and my outlook.

I went for a coffee and began to wonder what people would think if they knew what was under my trousers. Perhaps someone would think it’s cute or interesting. Perhaps I would see a cute girl and want to talk to her, all the while knowing underneath there was a useless little clitty. As my mind wandered to more risque topics, I was soon given a reminder of the purpose of the cage. More on that later.

After I got home, I swapped my rosy pink girly pajamas and slippers to match my cute little cage. I decided to get some things done around the house; I did some cleaning, folded my clothes, and made sure that everything was nicely organized and taken care of.

Each time I thought of a little job to do, I would tell myself that good girls keep their home tidy and that I wouldn’t unlock myself until I had done something. It really helped me concentrate on a number of tasks that needed doing.

By the time evening arrived some of those familiar urges were bubbling to the surface and my chastity felt more than a bit tight on a few occasions, but nothing that made me run to free myself from confinement.

After dinner, I watched a film and felt the clock countdown to my goal. I can report that I made it to 10 pm plus a few extra minutes. I unlocked myself before bed, and while it felt nice to be free, it was more like the feeling of taking off a comfortable pair of shoes than ripping off an itchy sweater.

Lessons Learned: Does Chastity Work?

After my first 12-hour day in chastity I tried it again a few days later and again a few days after that. Each time, I lasted a different amount of time, once more than my first day, one less. I can say that after a few experiences with the cage on and trying to use it to up my femme feelings in my daily life, I’m a little disappointed with it. Or maybe I didn’t do it right.

Having tried wearing the cage for 12 hours and a few times after that, I had some thoughts. I don’t think that wearing it for a day or a few hours here and there is enough time to really change my mindset. Also, I think that this type of play is perhaps best done with a partner who will add to the mental aspect of it. I can see how wearing a cage for several days or weeks would build up a more feminine mindset, especially with a consenting and trustworthy play partner.

Future Plans: Going Deeper into Chastity

I’m going to try again. I’m going to try for longer. I liked how comfortable wearing the cage is and I like that it makes my clitty look cute in the mirror. I think I really need to make an effort to commit to the mental side of chastity more; definitely more than half of this play method is mental. Mindset is key. Just don’t lose your keys.