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Chastity Training: From Zero to Hero

Ringed metal cock cage

Jail Bird Cock Cage

It’s not as simple as slapping on a cage and saying “look at me, I’m chaste”. Chastity is an ongoing journey, and to make the most of it you’ll need practise and training.

What’s Your Chastity Goal?

Before you can start your journey, you need to know where you’re going! Take some time to identify what your goals are from male chastity. Some examples include:

Some goals will be easier to reach than others, but in general the process you’ll go through will be quite similar.

Setting the Ground Rules

Once you know your goal, it’s important to spend some time discussing with your partner what the rules of your pledge will be. This is most often laid out in a chastity contract.

At first, your rules might be quite simple, just laying out when the cage must be worn, and how the slave should behave while caged. As time goes on, you can add more to your contract to reflect your changing relationship. Each time the contract is changed though, it should be discussed to make sure both parties are happy with the changes.

Start Off Slow

No matter what your endpoint is, you’re going to want to start off slow. Spend some time making sure that your cage is the right one for you, and fits correctly. You might find that it takes trying a few cages to get it right, but that’s completely normal. It’s worth spending the time and money though, because it makes all of the next steps much more enjoyable.

Next, start wearing it! You might find being caged a little uncomfortable at first, due to the weight of the cage, extra bulk in your pants, or any other reason, so don’t worry about keeping it on for long periods straight away. Even just a few minutes a day works. Over time, gradually increase how long you wear it until you’re approaching a comfortable duration.

If you can reach the point where you’re spending an hour caged with no breaks, that gives you plenty of opportunity to start experimenting and letting the real training begin.

Lockink Cellmate cage

Cellmate V2 App Controlled Chastity Cage

Chastity Training for Sex

The most basic kind of chastity training a couple can try is training for sex. You might choose this kind of training for a variety of reasons, including:

  • Helping with premature ejaculation or a man who finishes too quickly to satisfy his Mistress.
  • Teaching a man to be better at pleasuring his Mistress.
  • Helping a man orgasm faster.
  • Pegging.
  • Role-reversal (letting the woman be in control).

Generally, this kind of training will involve keeping the man caged until his Mistress is finished. That might be after one orgasm, or ten! Only once she’s satisfied will he be uncaged and allowed his pleasure.

Aside from that, this kind of training will usually involve becoming much more attentive to Mistress’s needs. Figuring out what works for her, and perfecting the techniques to bring her to orgasm. After all, the faster she’s done the sooner you cum.

For things such as pegging and female dominance, take the time to research each activity and ease into it the way you would if you were doing it outside of chastity. Don’t pull out a giant strap on ten minutes after a man first puts on a cage!

Chastity Training for Obedience

Obedience training is usually the most common kind of chastity training. This involves using the cage as a tool to teach a man his place in the relationship, and have him faithfully following Mistress’s instructions.

The easiest way to accomplish this is allowing him out of the cage when he behaves properly. It’s extremely simple, but you’d be surprised the effort men are willing to put in when it’s their only way of having an orgasm.

At first this might be quite simple, such as keeping him caged until all the housework is done. Rewards will usually be plentiful, but over time as he gets used to behaving the way he should, you can taper down the rewards and save them for truly exceptional behavior.

For example, while you might reward him each night for the first few weeks (as long as he behaves), a couple of months in you might only reward him twice a week for several days good behavior. Then as time goes on, you can save the rewards for special occasions like completing a major DIY job or going two weeks without any bad behavior.

Black ringed cock cage

Black Steel Male Chastity Cage

Chastity Training for Humiliation, Sissification and Emasculation

Once the basic training is out of the way, you might start to move into more hardcore aspects of BDSM such as humiliation, sissification, and emasculation. As we mentioned earlier, this should only be done with both parties permission. It’s not for everyone!

It’s difficult to give any comprehensive tips on this kind of training, as what you do will depend on which kinks you’re into, and what’s in your chastity contract. Generally though, it’s always good to take things slow and gradually build up the intensity over time.

For example, you might start by simply ridiculing him when you see him caged or making him wear frilly panties. Then over time, up the ante. Start showing pictures to his caged cock to friends or forcing him to wear make up. If he’s still up for more you could build up to full humiliation by parading him around in front of your friends, or even cuckolding him.

Think about what you enjoy as a couple, what’s off limits, and start to design a gradual program that will ease the man into any new aspects. You should also give him plenty of opportunities throughout the process to opt out, dial things back, or change his mind. It’s a good idea to have regular conversations (not during chastity play) to see how things are going and if everyone is truly happy.

Chastity Training for Permanent Chastity

The final challenge for most chaste men will be wearing their cage 24/7. This can take a long time to work up to, and has it’s own hurdles.

After he’s used to wearing it for an hour or two, you’re going to want to gradually increase the duration of lock up time until he can make it through an entire day. Then you can try a full night.

Men will naturally get erections throughout the night, so staying caged overnight can be difficult. It may be painful, and may affect his sleep cycle. If it’s causing too much problem, the best advice is to just let him out overnight, and put the cage back on in the morning. For all intents and purposes, he’s still locked 24/7 and the morning and night routine can become a ritual part of your chastity relationship.

Once you figure out how to deal with night-time, it’s simply about increasing the duration! Go in stages, and don’t be frustrated if a man needs a break from the cage. It’s a big lifestyle change to be permanently chaste.

You’ll also need to start milking his prostate! Over longer periods of time without orgasms, a man’s prostate will naturally build up an excess of prostatic fluid. Regular prostate milking will help him expel this fluid, and as an added bonus will help make him even more horny and desperate than usual.

Benefits of Chastity Training

By now you’re probably wondering if chastity training is really worth the effort. It sounds like it will need a lot of time and effort, and you’re having plenty of fun just using a cage occasionally for a little kinky time.

Proper chastity training can bring a host of benefits, including:

  • Better orgasms for both Mistress and slave.
  • A more attentive, caring slave.
  • An empowered Mistress.
  • A closer, more stable relationship.
  • More confidence in your own preferences.
  • The freedom and willingness to explore other new fetishes.

Start your training today with our simple tips, and experience everything that your chastity relationship can bring.

Michael Cole Author Profile Picture

Michael Cole

Michael is the author of the Total Chastity Diary and has been in and out of chastity since his mid-thirties. He’s now 41. He lives and works in Boston, has a white-collar job, and is single by choice. 

“There’s nothing hugely special about me. I’d describe myself as your typical modern, forward-thinking guy. I enjoy sports, staying healthy, love my family and friends, and have a satisfying career that pushes me to work hard so I can enjoy some of life's luxuries. 

I’m whatever constitutes as “normal.” It just so happens that I also enjoy the feeling of putting my cock in a cage, leaving it there for a week or two, then reaping the benefits of being released from my cage. 

Starting my chastity journey felt like starting any other new hobby or interest. I wanted to make sure I was doing it right and had good equipment to help me achieve the results I wanted. But when I began looking into male chastity and cock cages, what I found was a lot of fetish talk. 

While I accept this is what male chastity means for some - dressing up as a sissy, being spanked by a Dominant and whatever - the kinky kicks aren’t what I’m into. 

My hope with the Total Chastity  Diary is to bring a more matter-of-fact voice to chastity experiences.”

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