How to Train a Sissy – 7 Steps to Complete Sissification

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Who among Dommes wouldn’t adore having a live-in sissy? Your life might be so much simpler if you had a sissy-maid slave under your control.

Training your own sissy has a ton of benefits if you’re a female supremacist, a naturally dominant bitch, or you have a dominant streak lurking just beneath your vanilla facade.

It’s possible that you already have the ideal candidate in the form of a boyfriend or husband who prefers to be submissive. If not, there are plenty of sissies who are more than willing to help you.

However, I’ll be upfront. There aren’t many sissies who have received the necessary training to perform the duties of a sissy-slave-maid-servant-slut. Untrained sissies may be slothful, uninspired, and disorganized men who believe they can put on a dress and clumsily apply lipstick and then declare themselves to be suitable sissy material.

In reality, they are nothing more than naive wannabe women who have no idea what true sissification actually entails. They require a Domme like yourself who is skilled in sissy training because, with very few exceptions, they are unable to properly train themselves.

Warning: training a sissy is difficult and time-consuming work. To satisfactorily complete the work, it can take a year, and frequently longer.

Having said that, your life will never be the same after the work is finished. As long as you need your sissy’s loyal assistance, you will continue to benefit from your training. Although you will be on opposite ends of the D/s spectrum, you will both be living happy, contented lives that are complete.

What is a sissy?

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A sissy is essentially a crossdresser who is submissive. She could be gay (attracted to men), but she’s probably not. A sissy is drawn to all things feminine. She would prefer to dress nicely than be with a girl who does, although she would also enjoy that.

A sissy would rather go down on a girl than actually fuck her as a man. Because she is naturally submissive, a sissy rarely feels confident around a beautiful woman. A cute girl terrifies her cock, which will soon change under your guidance into a limp, useless clitty.

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A sissy would prefer to be a submissive domestic/sexual servant who simply tucks her clitty into her underwear.

Even though the majority of sissies are heterosexual, they occasionally need a man, but only to prove that they are feminine. Gay sissies can develop into the best fuck toys and cocksuckers on the planet because they are inherently attracted to men.

I encourage you to read this article, What Does it Mean to be a Sissy?, to fully understand how a sissy thinks. Once you know how a sissy thinks, you can use that knowledge to bring her completely under your control.

You want that, after all. And perhaps most significantly, she wants that!

Defining Expectations

This is all about rigorous sissy training, so let’s get that out of the way up front. This is not some half-assed, amateur sissy bullshit. This is going to be sissification at its best. Your sissy-trainee will live up to the high expectations you have for her, and she will give you her all.

Make sure your sissy understands the intended outcome of this rigorous sissy training program. She’ll be exposed as a result to:

  • full emasculation
  • whole feminization
  • (Now that she knows) Permanent sexual denial
  • absolute compliance
  • humiliation in public
  • Lots of laundry, ironing, and house cleaning.
  • becoming a skilled sexual slave
  • weight loss


Yes, this will require a lot of work from you, as I’ve already mentioned. You can use a whip (or a crop) if you want to whip her into a sissy shape, but once you do, your life will never be the same. Furthermore, if you ever get tired of your sissy, you can always kick her out of the way, preferably with the pointed toe of your high heel. The subsequent one will be much simpler once you learn how to train a sissy.

Step #1 – Elementary Emasculation

Ridding her of her masculinity is the first step in sissy training. She needs to start acting and thinking like a lady in order to carry out the sissy tasks that will be expected of her. She is no longer a man and never will be, so the proper actions must be taken.

Women naturally have less hair on their bodies than men. They take away what they do have. Hair removal is where a sissy begins to feel feminine. She starts shaving every day, no matter what.

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Whether someone notices or reacts in any way is irrelevant. She shouldn’t worry about that any longer. She following instructions is the only thing that matters. Additionally, you must insist that she always have a smooth, hairless body.

The same is true of nails. Pretty polished toenails are a must for sexy women. A sissy does the same. Your sister’s shoes and socks will cover her toenails if she continues to work. Her toenails will be on display outside during the summer for everyone to either admire or mock.

She is no longer concerned about this. Her priority is to flaunt her femininity, and if doing so puts her in jeopardy or puts her in embarrassing circumstances, so be it. This is a good starting point because she will eventually start to crave humiliation.

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Her fingernails follow suit, just like any girl, a sissy needs to learn how to take care of her nails. This encompasses polishing, buffing, and filing. Let her choose the colour first. Most likely, she’ll go with a clear coat to avoid drawing too much attention to herself.

Demand that she gives her nails a sissy-friendly colour after a few months. She might object at first, but reassure her that this is what she agreed to. Her employer will now see her for the sissy that she truly is. Some of the female employees might even compliment her on her nails.

The unattractive, overgrown, and unfeminine eyebrows must also go. Get her a good set of tweezers and teach her that pain can occasionally be associated with beauty. Encourage her to maintain perfectly groomed brows and teach her how to make them arched and feminine.

The final element of basic emasculation is to pierce your sister’s ears. This is a no-brainer in every way. Nowadays, getting your ears pierced is completely acceptable for people of any gender. Sissies are no different. At first, a basic set of studs will do. This will serve as the basis for later, more feminine, girly-girl earrings.

It’s time to start more rigorous sissy training now that the basic feminization/emasculation issues have been resolved.

Step #2 – Sissy Sexual Denial

The goal of sissy training is to develop a submissive, submissive, fully feminine creature with a strong desire to serve in any capacity you deem necessary. Your sissy’s enthusiasm will be needed for this.

It is preferred to keep her sexually denied and thus erotically stimulated in order to ensure that she always maintains a desire to please. You won’t need to stimulate her in any way. She must put on a chastity cage in order for that to happen.

When they are horny, men usually behave themselves. The idea is to keep a sissy horny because she still has her male organs. Her horniness will lessen a little during prolonged sexual abstinence, leaving her in a constant low-level erotic arousal.

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The best state for a sissy to be in all the time is this one. She will continue to act in the ‘proper’ sissy attitude as a result. She will keep her head where it belongs with perpetual chastity. The majority of her vocabulary will be reduced to the two words “yes Miss.”

As a sissy trainer, you won’t have to worry about things like prostate milking, ruined orgasms, humiliating orgasms, or supervised orgasms. She has voluntarily given up all rights to any and all expressions of masculinity by agreeing to become your sissy. This includes any act of sexual gratification that even remotely resembles manhood.

She should never be permitted to orgasm as a man again because she is no longer one. Although it may seem harsh if not downright cruel, permanent sexual denial is necessary. She’ll get used to it eventually and adapt. She will learn to focus her sexual resentment on matters that are more crucial—making you happy.

She will need to be let outside of her cage once a week so she can shave her genitalia. She should be aware that any fondling of (or leakage from) her sissy clitty during this shower time will result in her immediate dismissal as your sissy. She won’t want to take that chance, I can assure you.

She takes a shower and then puts the chastity cage back on. If she accidentally becomes erect during training, which is possible, a bag of ice placed directly on her genitalia will cause her to quickly lose size.

If you have a mean streak, you can shrink her down to the size of her cage with a few well-placed blows from a small cane to the tip of the offending member.

In the future, she will become instantly limp at the mere sight of the cane because this experience has been so excruciatingly painful.

Although it might take her a week or so to get used to wearing a chastity device, once she is broken in and properly fitted using this chastity sizing guide, her cage only needs to be removed once a week for shaving. She’ll forget that she ever even had a working cock after a year has passed.

It’s time to teach your sister to concentrate on making your life better now that her emasculation is largely under control. She will eventually learn to live for that.

Step #3 – Sissy Maid Duties

You’re now prepared to benefit from your knowledge of effective sissy training. She is ready to carry out your instructions. You essentially have your own sissy slave in your possession. You could give her the following list of tasks. The only thing limiting you is your imagination.

  • thoroughly clean the house.
  • grocery shopping
  • making meals
  • Hand wash your lingerie and wash and iron your clothes.
  • paying bills
  • paint your toenails
  • fluff your lover’s hair,
  • worship/lick your pussy,
  • clean up after sex, and do all the yard work
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You want to get her to the point where she stays at home full-time. But you might need her to keep working outside the home. You can spend her salary on things like manicures and pedicures, makeup, lingerie, high heels, and trips to the hairdresser.

She will have to do her chores after work if that is the case. It’s amazing what a pushed, reprimanded sissy can achieve. Her entire life is devoted to making your life better.

Pimp your sissy as a maid or sex slave to friends and acquaintances is another way to bring in extra money for the family. A sissy should be made to pay in some way for her existence.

Step #4 – Feminization

The emphasis should shift to further feminizing your sister once she has been sexually and physically denied, and is capable of carrying out her maid duties. She will only have a faint memory of ever being a man once Step #4 is fully implemented.

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Sissies must be both attractive and sexy. There should be no exceptions to your sister’s daily makeup routine. Light foundation, a little mascara, and lip gloss should be sufficient if she works outside the home. On the weekends, wearing a lot of makeup—including false lashes—will be standard.

She should be forced to spend five days a week watching YouTube makeup tutorials. Her makeup artistry will be flawless after a year, and you won’t feel embarrassed to parade her around in public.

A sissy should ideally be slim. She’ll look much better in her constantly growing wardrobe and be more appealing as a sex object. She ought to have to read The Sissy Weight Loss Manifesto. The Sissy Feminizing Workout for an Hourglass Figure will shape her body into something delectably desirable once her diet is firmly under your control.

She should be acting, behaving, and looking like a female at this stage of the sissy training program. The only thing lacking is a female voice. She’ll need to practice speaking like a sissy in addition to her makeup. In fact, every day! Exercises to feminize her voice will boost her self-confidence and help her shed any last traces of her masculinity.

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Step #5 – Sissy Sex Education

Even though it’s a difficult task, it’s well worth it to turn a man into a docile, submissive, and subservient sissy maid with all of his nasty male habits. But now comes the really fun part. It’s time to transform her into the ideal sissy sex object.

A sissy maid enjoys doing housework very much. But as a sissy slut, she really shines. a sexual toy. She no longer penetrates sexually. She now needs to receive sexual receptive training.

Of course, anal training comes first. Buy her a dildo that will initially hurt her a little—one that is neither too big nor too small. She should ride it for 10 to 20 minutes each day to gradually loosen up her sissy pussy.

It is clear that she hasn’t engaged in any sexual release for some time. She will start to experience some semblance of sexual pleasure as the dildo’s tip rubs against her prostate gland. If she’s fortunate, she might sense the internal stirrings of that elusive sissygasm.

A desire for anal penetration will develop as a result of the possibility of experiencing sexual release in this manner in the future. She’ll enjoy it a lot, and your male friends will also be entertained in the future thanks to that.

Your sister must become a skilled cock sucker in order to function as a sexual receptive. Some girls yearn for cock. Others find it repulsive or indifferent. It really doesn’t matter because ALL sissies should learn to at least competently cocksuck and then swallow.

Simply instruct her to attach the dildo to the shower’s side, kneel down, and practice repeatedly. Nothing is more repulsive than watching a sissy experience a gag reflex while deep-throating a big, hard dick.

If you’re a Domme and want to have intense sex, you can fall back on your sister. Put a dildo on your sister and let her fight if your lover or boyfriend isn’t around.

This kind of fucking has its benefits. There aren’t any early ejaculations or cocks that aren’t fully hard to be disappointed with. You can enjoy as much time as you want being fucked by a permanently stiff cock of the size of your choice.

You just pull out the riding crop when your sissy’s stamina starts to run low and you need more time to get to the promised land. In order to keep her moving in the right way and give you the satisfaction you deserve, give her ass a few strategically placed strokes.

Driving your sissy further into submission has its advantages. Cuckolding her is the best solution for this. She can be taught to fluff up your partner before sex and clean up after it for both of you.

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Realizing that your boyfriend will cuddle three times in one night while she hasn’t orgasmed in more than three months is a horribly erotic feeling (for you both).

So you can see, sissy sex does exist. Just in a very different way than what she was accustomed to as a former man. She will tell you if you ask that she much prefers erotic, exquisite sissy sex to superficial, fleeting male orgasms.

Step #6 – Sissy Emasculation – Advanced

It’s time to completely feminize her now that she’s been properly trained to be a sissy sexy toy/fuck doll. There are three distinct ways in which this accelerated emasculation process is carried out.

Removal of hair permanently

At some point, it will be necessary to remove all of your sister’s unwanted hair, which means everything from the head down. On the face, electrolysis is used to achieve this, and on the rest of the body, IPL or laser treatments are used.

Feminizing hormone therapy, or FHT

She should be forced to start taking female hormones at this point in her training to be a sissy. Her skin and facial features will be made softer by them. In order to give her a more feminine figure, they will also redistribute her fat reserves to her hips, thighs, and butt area.

However, the fact that FHT will start to develop her breasts is just as significant. The desire for a nice pair of tits that will permanently mark a sissy as a woman is universal.

Facial Feminizing Surgery, or FFS

FHT will somewhat soften a sissy’s face, but nothing can replace facial feminization surgery. The structure of some features on a male face simply isn’t as good as it is on a female face.

Surgery to feminize the face is obviously expensive. But FFS is a crucial step in the sissification process if your goal is to have the most feminine and attractive sissy possible.

Step #7 – Public Humiliation

Okay, you’ve taught your sister how to behave and walk like a girl. She has lost weight, and her posture and feminine demeanour are flawless. Her makeup is consistently flawless. She has developed into a hot, attractive woman.

Sissy and wife spreading together

She is skilled at satisfying both males and females sexually, which is also important. She is the perfect fuck doll and the ultimate sex toy. What more could you possibly ask for, Domme Miss? Not a lot!
But you must continue to occupy and inspire her. She will be motivated by her constant denial, for sure. She also requires a psychological lift, though. It’s important to keep in mind that in the interest of her mental health…

A happy sissy is a humiliated one!

It’s your responsibility to put a sissy purposefully in the appropriate humiliating situations because she craves humiliation.

Send her to the nail salon by herself. She needs to get used to being treated with respect. It will be embarrassing to have female nail technicians work on her if she doesn’t pass as a girl completely (which she probably doesn’t).

but in a degrading, sexually charged manner. While the polish is being applied to her long, sexy nails, her limp clitty will be twitching in her underwear.

Speaking of panties, have her visit a specialty lingerie store and have a female sales associate assist her in choosing a few pairs of sexy panties rather than buying them online. Although purchasing them in this manner will cost more money, the humiliation factor will make it well worth it.

This method might also be effective at a department store’s cosmetics counter. It would be sexually humiliating for her to ask a female cosmetologist to assist her in choosing the appropriate shade of foundation for her skin tone. Even a free makeover session could be won by your sister.

Hosting a party with your sissy serving as the sex slave or party servant is another way to humiliate her. She might also be required to serve your guests in other ways besides providing drinks and snacks at the drop of a hat.

Finally, a sissy may find it incredibly humiliating to be face-slapped in public. Take her to a busy department store for some retail therapy. Then, while the onlookers are still quite close by, shout, “Don’t argue with me!” Immediately after, give her a hard slap across the face. You’ll draw looks. Your sister will also feel ashamed. And it will activate both of you.

Here is the complete sissy training Guide if u are looking for more.

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