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How to Train a Sissy – 7 Steps to All-Out Sissification

how to train a sissy

What Domme wouldn’t love to have her very own live-in sissy. Being in charge of a sissy-maid-slave could make your life so much easier.

If you’re a female supremacist, a naturally born dominate bitch or have a domineering streak loitering just beneath your vanilla facade, training your own sissy has many, many advantages.

You may already have the perfect candidate living with you right now—in the form of a submissively inclined husband or boyfriend. If not, there are an abundance of sissies out there that are more than eager to serve you.

But let me be honest. There are very few sissies that have been properly trained to adequately serve as a sissy-slave-maid-servant-slut. Untrained sissies can be lazy, unmotivated and undisciplined males who think they can throw on a dress and messily apply some lipstick; then proclaim themselves as bonafide sissy material.

They’re actually nothing but delusional wanna-be females—with absolutely no comprehension of what legitimate sissification (Train a Sissy) really entails. And since—with very few exceptions—they’re incapable of properly training themselves, they need a Domme such as yourself that knows how to train a sissy properly.

Be forewarned however: training a sissy is tedious, challenging work. It can take a year, oftentimes more, to satisfactorily complete the job.

Having said that, after the work is finished, your life will never be the same. You will continue to reap the rewards of your training for as long as you require your sissy’s devoted service. Both of you will be living fulfilling, satisfied and complete lives—albeit from opposite ends of the D/s spectrum.

What Exactly is a Sissy?

what is a sissy

A sissy is basically a submissive crossdresser. She may be gay (attracted to males) but often not. A sissy has a fascination for the feminine. She would rather wear beautiful clothes than be with a girl that wears them—although she would enjoy that too.

As a male, a sissy would prefer to go down on a girl than to actually fuck her. Since she’s submissive by nature, a sissy is not typically confident around an attractive woman. Her cock—that will soon be morphing into a limp, useless clitty under your tutelage—is frightened by a cute girl.

A sissy would rather just tuck her clitty into her panties and be an obedient domestic/sexual servant.

While most sissies are heterosexual, they do require a man occasionally, but only as an instrument to validate their femininity. Gay sissies are obviously attracted to men and can evolve into the best fuck toys and cocksuckers on the planet.

To get the full essence as to how a sissy thinks, I invite you to read this article: What Does it Mean to be a Sissy?. Once you understand how a sissy thinks, you can parlay that information to bring her under your complete control.

That’s what you want. And just as importantly… that’s what she wants!

Train a Sissy – Defining Expectations


Just so we’re on the same page, this is all about hard-core sissy training. There is no half-ass-amateur-sissy-bullshit going on here. This will be sissification at it’s finest. You will be expecting a lot from your sissy-trainee… and she will be giving you everything she has.

You need to make sure your sissy is fully aware of the desired end-game of this intense sissy training system. This will result in her being subject to:

  • Complete emasculation
  • Full feminization
  • Permanent sexual (as she now knows it) denial
  • Unwavering obedience
  • Public humiliation
  • Lot’s of house cleaning, washing and ironing
  • Becoming an expert sex slave
  • Losing weight

Yes, like I’ve already mentioned, this is gonna be a lot of work on your part. But once you have her whipped into sissy-shape—and you can use a whip (or a crop) if you so desire—your life will never be the same. And if you ever become bored with your sissy, you can always kick her aside, preferably with the pointed toe of your high heel. Once you know how to train a sissy, the next one will be much easier.

Step #1 Train a Sissy – Elementary Emasculation

elementary emasculation

Sissy training begins with stripping away her masculinity. In order to perform the sissy duties that will be required of her, she needs to start thinking, acting looking like a lady. She’s no longer a man and never will be again, so appropriate measures are necessary.

Women, naturally, don’t have much hair on their bodies. What they do have, they remove. Femininity for a sissy starts with hair removal. She develops a habit of daily shaving… no matter what.

It doesn’t make any difference whether anyone notices or says anything. That should be none of her concern any longer. The only thing that does matter is that she does what she’s told. And you must demand that she has a smooth, hairless body, 24/7.

This is the same for nails. Sexy women always keep their toenails prettily polished. A sissy follows suit. If your sissy still goes to a workplace, her shoes and socks will hide her toenails. Outside, during the summer months, her toenails will be available for everyone to either admire or make fun of.

This is none of her concern anymore. Flaunting her femininity is paramount—and if that involves ridicule and humiliating situations, so be it. She will learn to crave humiliation and this is a good place to begin.

Her fingernails are no exception. A sissy needs to learn to take care of her nails; just like any girl would. This includes filing, buffing and yes—polishing. Allow her initially to pick the color. She’ll most likely choose a clear coat so as to not draw too much attention to herself.

After a few months, demand that she paint her nails a sissy-appropriate color. At first she may balk but remind her that this is what she signed up for. Her workplace will now see who she really is—a sissy. She may even get compliments on her nails from some of the female employees.

The ugly, bushy, unfeminine eyebrows need to also go. Buy her a good pair of tweezers and train her to understand that beauty is sometimes painful. Teach her to create high-arching, feminine brows and require her to keep them perfectly plucked.

The last item of elementary emasculation is to get your sissy’s ears pierced. This is an absolute no-brainer. It’s perfectly normal these days for any gender to have their ears pierced. Sissies are no exception. A simple set of studs will be fine at first. This will lay the foundation for more feminine, girly-girl earrings later on.

Now that the fundamental feminization/emasculation areas are addressed, it’s time to move on to more intense sissy training.

Step #2 – Sissy Sexual Denial

sissy sexual denial

The whole idea behind sissy training is to create a docile, obedient, subservient and fully-feminized creature that maintains a penchant to serve—in any way that you deem useful. This will require enthusiasm on your sissy’s part.

Sissy Shop

The preferred way to make sure that she always maintains an eagerness to please is to keep her sexually denied; and thus erotically stimulated. It will not be necessary for you to stimulate her. That is accomplished by requiring her to wear a chastity cage. Here’s is some very useful information about those devious devices.

Men typically are on their best behavior when they’re horny. Since a sissy retains her male organs, the idea is to keep her horny. During long term sexual denial, her horniness will subside somewhat, leaving her in a perpetual state of low level, erotic arousal.

This is the perfect ‘state’ for a sissy to be in on an ongoing basis. It ensures that she maintains the ‘proper’ sissy-attitude. Permanent chastity will keep her head where it belongs. Her vocabulary—for the most part—will be diminished down to two simple words, “yes Miss.”

As a sissy trainer, you don’t need to worry about supervised orgasms, maintenance orgasms, ruined orgasms, humiliating orgasms, prostate milkings, etc. Agreeing to become your sissy, she has voluntarily forfeited all rights to any and all expressions of masculinity. That includes any sexual release that has any semblance to manhood.

Since she’s no longer a man, she should NEVER be allowed to orgasm as a man… ever again!. Although this sounds harsh—if not out-and-out cruel—permanent sexual denial is absolutely mandatory. She will adapt and eventually become used to it. She will learn to direct her pent-up sexual energy to more important matters—that of making you happy.

It will be necessary to let her out of her cage on a weekly basis so that she can shave her genital area. During this shower-time, she should be aware that that any fondling of (or leakage from) her sissy clitty will be grounds for her immediate dismissal as your sissy. Trust me, she will not want to risk that happening.

Following her shower, the chastity cage goes immediately back on. If she inadvertently becomes erect—which might happen at the beginning of her training—then a bag of ice, applied directly to her genitals will shrink her down rather quickly.

If you happen to have a mean streak in you, then a few well placed strikes from a small cane, directly to the tip of her offending member, will make her small enough to reenter her cage.

This is such an incredibly painful experience that, going forward, just the sight of the cane will cause her to immediately go limp.

Although it may take a week or so for her to adapt to wearing a chastity device, once she is properly sized using this Chastity Sizing Guide, and broken in, then her cage only comes off for weekly shavings. After a year has passed, she will forget that she ever even had a functional cock.

Now that your sissy’s emasculation is more-or-less under control, it’s time to train her to focus on improving the quality of your life. That’s what she will learn to live for.

Step #3 – Sissy Maid Duties

sissy maid duties

You’re now ready to reap the rewards of learning how to train a sissy properly. She is primed to do whatever you wish her to do. In essence, you are in possession of your very own sissy slave. Here is a list of chores that you might assign to her. You are limited only by your imagination.

  • clean the entire house
  • grocery shopping
  • prepare meals
  • wash and iron clothes
  • hand wash your lingerie
  • pay bills
  • paint your toenails
  • fluff your lover
  • worship/lick your ass
  • lick your pussy clean after sex
  • detail the car(s)
  • all of the yard work

Ideally, you want to reach the point where she is a full-time, stay-at-home-sissy. However you may need her to continue to work outside of the home. Her paycheck can be used to pay for your manicures/pedicures, makeup, lingerie, heels and trips to the hair salon.

If that’s the case, then she will need to perform her chores after work. It’s amazing what a chastised sissy can accomplish when she’s pushed. Her whole life revolves around enhancing your life.

An alternate way of generating additional household income is to pimp your sissy out to friends and acquaintances as either a maid or sex slave. A sissy should be required to pay for her existence—one way or another.

Step #4 – Feminization

feminization in progress

Once your sissy has been emasculated, sexually denied and is capably performing her maid duties, the focus should turn to further feminizing her. Once Step #4 is fully underway, the fact that she was ever a man will be only a distant memory for her.

Sissies need to be both sexy and pretty. Your sissy should be applying makeup every day—no exceptions. If she works outside of the home then light foundation, a little mascara and some lip gloss should suffice. On weekends, heavy makeup, including false lashes, will be the norm.

She should be required to watch makeup videos on YouTube five days per week. After one year, her makeup skills will be impeccable—so much so that you would not be embarrassed to parade her around in public.

If anything, a sissy should be skinny. She’ll look much better in her ever-expanding wardrobe plus she will be more desirable as a sex toy. The Sissy Weight Loss Manifesto should be required reading for her. Once her diet is firmly under your control then The Sissy Feminizing Workout for an Hourglass Figure will mold her body into something deliciously desirable.

At this point in the sissy training program, she should be acting, functioning and looking like a female. There’s only one thing missing: a feminine voice. In addition to her makeup, she will need to begin practicing Speaking Like a Sissy. Yes, every day! Voice feminization exercises will do wonders for her confidence—and will serve to strip the last vestiges of any remaining masculinity from her.

An excellent resource is L’s Voice Training. It is a comprehensive MtF TG vocal feminization guide that will have your sissy sounding as good as she now looks.

Step #5 – Sissy Sex Education

sissy sex education

Even though it’s a daunting task transforming a man, with all of his nasty male habits, into a docile, subservient and submissive sissy maid, it’s more than worth it. But now the real fun begins. It’s time to mold her into a perfect sissy sex toy.

A sissy maid is more than happy doing housework. But where she really excels is as a sissy slut. A fuck toy. She is no longer a sexual penetrator. She must now be trained as a sexual receptive.

This begins with anal training of course. Buy her a dildo—not too big and not too small—that will hurt her a bit at first. She should gradually stretch her sissy pussy out by riding it 10 to 20 minutes everyday.

She obviously hasn’t had any type of sexual release for some time now. The tip of her dildo rubbing against her prostate gland will begin to give her some semblance of sexual enjoyment. If she’s lucky, she might feel the stirrings of that ever-elusive sissygasm emanating from deep within.

Sissy Training

The prospect of someday experiencing sexual release in this way will foster a penchant for anal penetration. That will give her much enjoyment as well as provide for future entertainment for your male friends.

As a sexual receptive, your sissy must also learn to be an expert cock sucker. Some sissies crave cock. Others are either indifferent or repulsed by it. It doesn’t really matter as ALL sissies need to learn to—at least capably—suck cock… and then swallow.

Just have her stick the dildo to the side of the shower, get on her knees and practice, practice, practice. There is nothing more disgusting than a sissy going into gag reflex when deep-throating a big, hard dick.

As a Domme, you can use your sissy as a back-up when you’re in the mood for penetrative sex. If your lover or boyfriend is not available, just strap a dildo on your sissy and have her go at it.

Being fucked in this manner has its advantages. There are no premature ejaculations and no less-than-fully-hard cocks to be disappointed with. You have a perpetually stiff cock, the size of your choosing, fucking you for as long as you want.

When stamina becomes an issue for your sissy, and you need more time to reach the promised land, you simply break out the riding crop. A few well placed strokes to her ass will keep her moving with the proper motion and ensure that you get properly satisfied.

There’s something to be said for driving your sissy deeper into submission. Nothing works better for this than to cuckold her. She can be trained to fluff-up your lover before sex and perform clean-up duties—on both of you—afterwards.

It’s a terribly erotic feeling (for both of you) to realize that while she hasn’t orgasmed in over three months, your boyfriend will be cumming three times in a single night.

So you see, sissy sex is a real thing. It just happens in a much more modified manner that what she had become used to as a former man. If you ask her, she will tell you that she much prefers erotic, exquisite sissy sex over superficial and quick-ending male orgasms any day.

Step #6 – Sissy Emasculation – Advanced

advanced emasculation

Now that she’s been properly trained as a sissy sexy toy/fuck doll, its time to fully feminize her. This escalated emasculation process is accomplished in three, distinct ways.

Permanent Hair Removal

Eventually it will be necessary to rid your sissy of all unwanted hair, which means from the head, down. This is accomplished by electrolysis on the face and IPL (Intense Pulsed Light) or Laser treatments on the remainder of the body.

Most everything you and your sissy needs to know about Permanent Hair Removal For the Sissy can be found at that linked article. Eliminating her hair forever is a time-intensive and expensive process, but well worth it.

If finances are an issue, your sissy can either get a 2nd job or you can pimp her out as a fuck doll. I’m fairly certain that she would prefer the latter.

FHT or Feminizing Hormone Therapy

At this stage of her sissy training she should be required to begin taking female hormones. They will soften her facial features and skin. They will also re-distribute fat stores to her hips, thighs and butt area, giving her a more feminine figure.

Just as important though is that FHT will begin to grow her breasts. Universally, sissies want an nice pair of tits that will serve to cement her femininity in place… forever.

This would be a good time to read 10 Questions a Sissy Might Ask About Feminizing Hormone Therapy. Yes, taking feminizing hormones is a huge step; but a mandatory one when it comes to how to train a sissy properly.

FFS or Facial Feminizing Surgery

Although, FHT will soften a sissy’s face somewhat, nothing is a substitute for facial feminization surgery. There are certain features of the male face that simply do not possess the proper structure that a female face has.

Thankfully, this can be corrected with FFS. Since there are several regions of the face that need to be addressed, it would be wise to check out this article that gives an overview of what exactly is involved.

Of course facial feminizing surgery is expensive. But if your desire is to have the most feminine and pretty sissy possible, then FFS is an important step in the sissification process.

Step #7 – Public Humiliation

sissy public humiliation

Okay, you have your sissy trained to walk, talk and act like a girl. She’s dieted down and her posture and feminine mannerisms are impeccable. Her makeup is always perfectly applied. She is now a sexy, highly desirable female.

Just as important, she is proficient at pleasing both males and females sexually. She is the ultimate sex toy—the consummate fuck doll. What more could a Domme Miss such as yourself possibly want? Not much!

Sissy Webcam

But you need to keep her content and motivated. Sure, her perpetually denied state will motivate her. But she needs a psychological boost too. In the spirit of her mental well-being it’s good to remember that…

A humiliated sissy is a happy one!

A sissy craves humiliation and it’s your job to purposefully put her in the appropriate humiliating situations.

Send her alone to the nail salon. She must become accustomed to being treated like a lady. If she doesn’t pass fully as a girl (as she probably doesn’t), then having the female nail technicians attending to her will be—at first anyway—an embarrassing experience.

But in a sexually charged, humiliating way. Her limp clitty will be twitching in her panties while the polish is being applied to her long sexy nails.

Speaking of panties, instead of purchasing them online, have her go to a specialized lingerie shop and have one of the female sales associates help her pick out a few pair of sexy panties. Yes, they will be more expensive buying them this way, but the humiliation factor will make it more than worth it.

This technique could also work at the cosmetic counter of a department store. Having a female cosmetologist help her pick out the correct color of foundation for her skin tone would be erotically humiliating. Your sissy might even be able to score a free makeover session.

Another way to put your sissy in a humiliating situation would be to host a party—with her as the party servant girl/sex slave. Besides serving drinks and snacks she might be required to drop to her knees at the snap of your fingers and serve your guests in alternate ways.

Finally, public face slapping can be a horribly humiliating experience for a sissy. Take her out shopping to a busy department store. Then, with shoppers well within hearing distance, shout out: “don’t argue with me!” Then immediately slap her sharply across the face. You’ll get stares. And your sissy will feel humiliated. And it will turn you both on.

7 Steps to Train a Sissy

trained sissy

To briefly recap, the 7 steps to all-out sissification are:

  • Elementary Emasculation
  • Permanent Sexual Denial
  • Sissy Maid Duties
  • Feminization
  • Sissy Sex Education
  • Sissy Emasculation – Advanced
  • Public Humiliation

I don’t believe that there are too many things that would enhance a Domme’s—or her sissy’s—life more than having her own, well-trained sissy-maid-sex-slave. Yes, training a sissy properly is challenging, tedious and sometimes even expensive.

But once the the sissy training is completed, you will be living a truly extraordinary life.

Sissy Training on Steroids

If the prospect of sissy training turns you on, then you would probably be interested in The Complete Sissy Training Guide. It’s a serious, in-depth guide into all aspects of sissy training. Not much—if anything—is left out.

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