Chastity Training 101: A Beginner’s Guide to Male Chastity Training

If you’re new to male chastity training, you probably have some questions. That’s likely true whether you’re the person getting locked up or you’re the keyholder. Here’s an introduction to male chastity training, complete with tips for dipping your toes into the chastity lifestyle.

What is Chastity Training?

Chastity training is the process of being “trained” to only orgasm with a keyholder’s permission. The idea is to get to the point at which the male wears his chastity cage for as long as the keyholder desires. The keyholder dictates if and when the male gets to cum – she is in total control.

Outside of that, there is no one-size-fits-all approach. Different couples might have different ideas in mind, from simply enjoying a few hours of chastity play at a time – perhaps where the male serves his mistress – or building up to long term or even permanent chastity. The important thing is to make it your own and have fun with the process, no matter what your end goal is!

Chastity Training Tips

These tips can help you get the most out of your chastity training and ensure both the chaste male and his keyholder have a positive experience.

1. Define your chastity training goals

As mentioned, chastity training doesn’t necessarily mean the same thing for every couple. Start by considering what you want the outcomes to be. For example:

  • Wearing a chastity cage 24/7
  • Adding an element of control and subservience to a femdom or female-led relationship
  • Sissy chastity training – “sissifying” the male and forcing him to wear women’s panties, lingerie, clothing, makeup and hairstyles, or having him shave all his body hair
  • Slave training – turning a husband or boyfriend into a slave who serves his wife, girlfriend or male partner
  • BDSM and femdom roleplay, such as forced chastity training
  • Cuckold chastity training for a hotwife or shared wife relationship
  • Simply exploring something new with your husband or wife, otherwise known as husband chastity training

Check out these chastity games to play with your partner

When it comes to chastity play and chastity training, there is a multitude of different ways you can take it. You can go for occasional use, or you can make it a 24/7 experience. It all depends on what you and your partner’s expectations are. Really ask yourself what you want out of it, what are your goals? What are your wife’s or partner’s goals? How far are you willing to go? Explore the options and see what fits best.

If you are freshly starting and have no experience in any BDSM or femdom relationships, it can be tricky to figure out exactly how you want to integrate it into your life. If you want to start off a bit tamer, then jumping into sissy chastity play and 24/7 wear is not the way to go. You want to work up to these experiences as to not overwhelm or discourage yourself.

Starting with daily use for a few hours and then practicing orgasm denial and mental discipline at night is an excellent way to build up to the more involved play. Cut to the Chaste wrote an excellent article where they connect the similarities of chastity training to military training, discussing how it involves discipline and walking before you run.

Since your partner will be such a significant part in the chastity training and play, see how intense a role he or she wants to play in the experience. For men with wives or girlfriends, you can incorporate a lot of femdom play. Things like forced chastity training or sissy chastity play, where you are being sissified by your partner with panties and female lingerie. 

You can even go a step further and do cuckold chastity, where you watch your sexy wife make another guy cum while you are pulsating in your chastity cage. Whatever you decide to do, make it fun and take it slow. 

2. Find the perfect fit

Finding the perfect fit to begin your chastity training is the most essential part of the process. Not only do you want the perfect fit to avoid any discomfort that might discourage you, but you also don’t want to allow for escape.

With larger chastity cages, there is a potential to allow for rubbing and playing with your cock, which breaks the rules and could upset your keyholder. You also want to make sure your chastity cage isn’t too tight. This could lead to medical issues, such as pinched nerves and cutting off blood circulation.

  • Find a chastity cage that fits
  • A cage that is too small could be uncomfortable or even dangerous
  • A cage that’s too large could facilitate escape – exactly what you don’t want

Looking for the perfect chastity cage? Here are the best places to buy one

3. Establish a chastity agreement

It is important you and your keyholder understand the terms and expectations regarding chastity training and chastity play. A consensual agreement is paramount if you are working outside of a relationship and adopting a dominant female to help with play and training. A physical agreement that is written down is the best option, and House of Denial has a wonderful guide to help you through the process.

The trust you put in your keyholder can be scary at times, so knowing the keyholder well and fully understanding the expectations is important. Adopt safe words for when you feel completely uncomfortable with the situation and ALWAYS make sure everything is consensual.

  • Only train with a partner you trust
  • Establish a chastity agreement, whether formal or informal, to clearly define limits and expectations
  • Create a safe word in case training gets too intense for either party
  • Always make sure everything is consensual

4. Start slow

Chastity training does not have to be scary, and it does not have to be a fast transition. Moving slow and making sure you are fully comfortable is the main objective here. Sexual desires are different for everyone. You want to make sure you are gaining pleasure from the experience as well, and all your consensual needs are being met, so ease into it.

Trial and error are key. Don’t get discouraged if it takes a few different cages to find the perfect fit. Never start with 24/7 chastity right off the bat: ease into it and try a few hours at a time, then try an overnight, then a full day, then a few days, etc., until the male can wear his cock cage full time (or for as long as the keyholder desires).

  • Ease into it
  • Trial and error, and don’t get discouraged
  • You might need to try multiple cages before you find the right fit

5. Explore different ways to play

There are many different ways you can incorporate chastity play into your sexual lifestyle. As part of your chastity training process, you can explore different ways to play, including:

  • Anal and prostate orgasms
  • Subservience: doing household chores and sexually serving the keyholder, etc.
  • Small penis humiliation (sph)
  • Sissification (dressing the male as a female)
  • Verbal humiliation
  • Gentle dom – being sweet, yet still keeping them locked up
  • Chastity roulette – a game to randomly decide how long the male stays in chastity
  • Tasks and rewards – give the male tasks that must be completed to be let out of chastity
  • Ballbusting and CBT (cock and ball torture)
  • Cuckolding/wife sharing
  • Vibrator on cock cage – to orgasm
  • Edging and ruined orgasms
  • Letting the male out of the cage, edging him, then caging him back up
  • Female worship, such as foot worship
  • Facesitting
  • Forced to watch the female masturbate
  • Other BDSM activities

Interested in chastity panties? Find them here

6. Keep it clean

Personal hygiene and cleanliness are critical to successful and safe long term chastity play. Choose a cage that allows enough access for regular cleaning, which is both sanitary and healthy, or allow for regular cleanings.

Many couples have supervised cleanings, where the female removes the cage and makes sure the male doesn’t pleasure himself while he cleans (or she ties his hands up and does the cleaning for him), then she puts the cage back on. It’s a great way to incorporate cleaning into chastity play.

  • Cleanliness and hygiene are critical
  • Schedule regular cleanings
  • Cleanings can be supervised to make sure the male doesn’t pleasure himself – make it part of your chastity play

7. Have fun

The utmost important element in all of this is to just HAVE FUN! We all have desires, and it is amazing when we can have our desires and fantasies played out. Making it the best experience possible by securing the knowledge to do so will be beneficial in the long run.

Here are some resources that offer additional chastity training tips: