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The Complete Sissy Training Guide
Part 2

the complete sissy training guide part 2

In Part 1 of The Complete Sissy Training Guide, we covered the basics of sissification. Basic training is just that: sissy things that must be mastered that serve as a prerequisite for more advanced and sophisticated training.

A soldier must complete basic training before they are taught advanced weaponry.

A college student spends much of their first two years taking general education courses that will help prepare them for their major field of studies.

A sissy needs to become familiar with basic girly-girl stuff before progressing to more advanced sissification training.

But before we get to these advanced feminization techniques, let’s talk about your sissy persona.

Establishing Your Sissy Persona

sissy persona

Males are either wired at birth or conditioned by society—or perhaps both—to behave in a manner that is the exact opposite of a demeanor that is more appropriate for a sissy.

Men, in general, are quick to judge, can be insensitive, and are typically not very good listeners. They feel compelled to dominate, achieve and take. More often than not, they have a penchant for being right.

Sissies on the other hand approach life in a kinder, gentler way. They listen with a compassionate ear, then reply in a thoughtful and gracious manner. They don’t feel the need to judge, but to understand.

Instead of contentiously arguing a situation, sissies tactfully ameliorate it using compromise and negotiation. True to their nature, they submissively submit to a peaceful and graceful outcome—whatever the situation calls for.

Sissies have no desire to fight or be right.

As a sissy, your role in society is to be a pleaser—in whatever way that is required. You’re not a taker but a giver. You’re not afraid to show your vulnerability, especially around other women. If you need help with things, you willingly ask for it.

While men play the role of sexual penetrators, you, as a sissy, are happy being a sexual receptive. In light of your evolving sexuality, this Part 2 of The Complete Sissy Training Guide will begin by focusing on reprogramming of your sexual responses and desires.

Sissy Desire – Sexual Reprogramming

sexual reprogramming

In order to proceed further with your sissification process, it will be required to strip away all vestiges of any manly sexual desires remaining inside of your pretty little sissy head. This is accomplished by regularly—which means everyday—listening to sissy hypno files.

Sissy Hypno

If it were possible to bitch slap the male out of you, I would certainly do that. Instead we’ll focus on a tried-and-true form of sexual reprogramming—sissy hypnotic files. You’re already familiar with them from Part 1 of this sissy training series.

I’ve listed a few sissy hypno sites over on my sissy resources page. Just scroll down to the Sissy Hypno section.

The idea behind sissy hypno is to condition yourself to think, act, feel and be more feminine. This of course goes beyond clothes, makeup and heels. It reaches down to the very core of your being and—much like a glacier—scraps and scours away what’s left of your manhood until you are unrecognizable as a male any longer.

Sissy hypno effectively flips your gender identity to the feminine. Your sexual responses soon follow suit. Over time you learn to accept, and even yearn for, a useless and limp sissy clitty. At the same time you are conditioned to crave anal stimulation. Sissifying hypnotic files will transform you into a submissive sexual receptive.

To give you a clear idea of what you’ve signed up for, download this file and listen to it ASAP.

A Sissy’s Greatest Sacrifice

The next step will be to…

Learn to Pleasure and Release Like a Girl

It’s time to learn to pleasure yourself in a feminine and girly-girl manner. You already know how men orgasm; in a grunting and forceful fashion. That’s not appropriate sissy sexual behavior. Girls cum with a more relaxed and unhurried approach.

A woman’s orgasm is more of a sensual experience: it requires a certain amount of time to build-up to. Her O can range from incredibly explosive to soft and gentle. They can be centered on her clit, pussy or spread across the entirety of her body.

In order to train yourself to cum like a girl you will need to properly prepare yourself, both mentally and physically. Orgasms—especially the female type—are triggered mainly in the mind.

Here’s the setup:

  • Give yourself a 30 minute block of time
  • Always wear at least a bra, panties and heels
  • Always have something in your pussy (from this point forward it’s imperative to associate sexual pleasure with anal stimulation)
  • Tuck your clitty downwards into your panties
  • Listen to sissy hypno or watch an erotic YouTube video
  • Nub the tip of your clitty with one finger only
  • With your other hand you can play with your nipples or sensually rub/caress your body
  • As you become more aroused, moan like a sissy slut
  • If your clitty gets hard, stop nubbing until you become soft
  • Don’t become attached to any specific outcome, just focus on experiencing feminine pleasure
  • If you do happen to release, that’s nice. If you don’t, that’s fine too

Once you experience sexual stimulation—if not satisfaction—in this way several times, you will gradually lose the desire to orgasm in a crude, manly-like fashion. It’s just not lady-like. Eventually you will train your clitty to remain limp throughout, even while climaxing.

Sexual Denial

Men tend to be shallow, spoiled sexual creatures. They typically want to experience orgasm often and in quick fashion. That can be a dismal and unfulfilling way to live life.

In stark contrast, a sissy’s life revolves around erotic denial. Going through the day in a perpetual state of semi-arousal enhances her sexuality and reinforces her docile, eager-to-please demeanor. For a sissy, delayed sexual gratification is the only proper way to live.

When a sissy is allowed an occasional release, she deeply cherishes it. In between those long stretches of denial, she loves how her clitty twitches in her panties while she’s applying false lashes and lipstick.

She enjoys diddling her clitty, fantasizing about the sexy lingerie, beautiful clothes and stiletto heels in her closet while allowing the evidence of a ruined orgasm drip slowly into her mouth.

To support her desire for a chastised existence, most sissies acknowledge that they will need the help of a chastity device. Not many things can train a sissy to accommodate long—perhaps permanent—periods of sexual denial than a properly fitted chastity cage.

In anticipation of this soon-to-be-happening part of your sissy training, now would be a good time to get an idea of how to size yourself correctly for a chastity device. You can use this helpful sizing guide to get familiar with the fitting process.

Sissy Chastity Dice Game

To make your chastised existence even more erotic and exciting, why not turn it into a game. All you need is a pair of dice. You, or preferably the keyholder to your chastity cage, rolls a pair of dice—one black and one white—to determine your length of lock-down.

I describe how this chastity dice game works in more detail in 7 Fun Sissy Chastity Games.

Attempt an Anal Orgasm aka Sissygasm

Total sissy sexual reprogramming culminates in the ability to orgasm only by anal stimulation. This is commonly referred to as a sissygasm. This advanced, and preferred, method of sissy sexual satisfaction is accompanied by a permanently limp and useless sissy clitty. Yes, your clitty is still somewhat of a sexual organ, but only leaks into your panties when you are aroused.

It can take considerable conditioning to experience a sissygasm but once you do, you’ll forever forget about manly-type orgasms. In fact, a leg quaking sissygasm might make you forget that you were ever a man at all.

Your Sissy Slut Factor

sissy slut

The main difference—as I see it—between a CD and a sissy is the submissive factor. Sissies exist to submit and serve dominate men, women and TG. There is both a psychological and sexual aspect to submissiveness.

Other than clothes, not many things will make you feel more feminine than having a cock in your mouth or up your sissy pussy. Even if you’re not into men, it’s imperative that you condition yourself to embrace your evolving existence as a slutty sexual receptive. Sissies don’t fuck… they get fucked.

Sissy Chastity

In the previous section on sissy sexual reprogramming, you were encouraged to practice orgasming like a lady by nubbing your clitty through your panties. Although that is a very nice way to cum, it is meant to serve only as a bridge to something greater.

That something greater will require taking sexual denial to a whole new level—with the help of a chastity device. Yes, it’s fun to play with your clitty through your panties but to satisfactorily progress through the sissification process, it will be mandatory that you stop all sexual stimulation of your clitty.

sissy chastity sissygasm

This is possible only by wearing a chastity cage. It’s now time to purchase one princess. It will be mandatory to keep your clitty in lock-down-mode for a minimum of 7 days.

The idea is to keep yourself in a perpetual erotic state of denial so that you can maintain the enthusiasm necessary for your complete feminization. That nasty refractory state experienced after orgasm is for unmotivated and undisciplined males. Since you’re no longer a man, you need to adopt and embrace the higher standards required of a sissy.

Denying sexual gratification will allow you to funnel your stifled sexual energy into making you a better sissy… and also a better person.

If you require an accountability partner in denying yourself (and you don’t have one), you can use the remote keyholder technique that I describe in The DIY Sissy Chastity Keyholder Method.

The ultimate goal of sissy sluttification is to de-emphasize—and eventually eliminate—your clitty as a functioning sexual organ and replace it with something more sissy-appropriate: your sissy pussy.

In order to accomplish that, it’s time to begin intensive…

Dildo Training

dildo training

Hopefull you’ve come to embrace the fact that your sexual satisfaction will now be coming by anal stimulation only. It’s time to buy yourself a dildo, if you don’t already have one. Not too big or not too small but…just the right size for you. It should be big enough that it hurts a little at first.

Don’t worry, you will learn to accommodate its size soon enough. Part of sissy training is stretching out your too-tight sissy ass.

Practicing Blowjobs in the Shower

Many dildos come with a suction cup at the base so you can practice riding it while it’s secured to the floor. This works even better in the shower as the wet environment will make the dildo stick really well—to the shower floor; or to the wall.

Stick it to the wall, soap it up, bend over and let it slide right in. Then turn around, get on your knees and practice being the sissy slut that you are rapidly becoming.

Caged and Plugged While Fondling Your Body

If you wanna feel super slutty, lie down on the bed and stick the dildo up your pussy. Pull on a pair of panties over your chastity cage and fondle your titties while fantasizing about being fucked silly.

Create that scenario enough times and you’ll be compelled to go out and find yourself the real thing. Once you do that, you are a bona-fide, card-carrying sissy slut.

Watch Videos of Your Favorite Fantasy

Since you’re a sissy, you’ve probably already done this a few—or a bunch—of times. My fantasy would be being fucked by a Domme wearing a strap on. Your visual might be something more like this?


Watching that video should make you feel super slutty. This is what a sissy slut’s sex life is all about. Your paramount purpose should be to look as sexy and desirable as possible so you can be used as someone’s fuck-doll.

The Humiliation Factor

Knowing that your caged clitty will be slowly shrinking in size because of non-use should put you in a humiliated state of being. That’s exactly the place where you want to be… sissified, emasculated and humiliated.

Sexual humiliation is an indescribably erotic feeling. That’s one of the perks of being a sissy. You want to begin looking for ways to purposely place yourself in humbling and demeaning situations. Here are a few ideas:

  • Walk up to a makeup counter and ask the sales girl what type of foundation would be appropriate for your skin tone
  • Make an appointment with a salon to have your toenails manicured and polished
  • Go to a department store (in male mode) and purposely browse through the lingerie section
  • Wear high-waisted panties that not-so-subtly show above your jeans
  • Have your belly-button pierced

By practicing putting yourself in embarrassing situations, you will become addicted to feeling that erotic rush that a humiliated sissy craves.

Dollification – Beautification


This section on dollification will have you focusing on becoming a desirable sissy—as attractive and as pretty as possible. Genetic girls spend a metric-ton of time and a ridiculous amount of money on beauty.

You princess, will need to invest even more of an effort if you want to be beautiful. You may not be able to approximate the look of a woman who’s on top of her beautification game, but you can certainly make yourself look presentable.

The positive part is that there are so many GG—for reasons that are inexplainable—who don’t make any effort at all to look feminine and sexy. A motivated sissy such as you can fill that gigantic gap in the feminine world with a conscientious dollification program.

Hair Removal

There’s is absolutely no reason for any seriously-minded sissy to not be smoothly shaven from the neck down. There is virtually no longer any social stigma attached to males shaving their entire bodies these days.

A firm foundation for femininity starts with a razor and removing all of that disgusting male hair. Shaving once-a-week (at a minimum) should become a feminine ritual for you. Read this helpful article on Sissy Shaving Tips.


In order to be a sexually desirable sissy, you will need to get good at makeup. It takes a ton of time and practice to get good however. For starters, check out these basic sissy makeup tips over at

Next, you’ll want to head on over to good old YouTube and start watching makeup videos. There are some really good ones from GG, CD, TG and drag queens alike. Depending on the look you’re after, you can learn something unique from most all of them.

Here is good video to get you started:


The one thing that GG know that sissies generally don’t is the importance of taking care of your face on a daily basis. Women spend a lot of time exfoliating, moisturizing and nurturing their skin. They understand that starting with a healthy looking, flawless base makes for flawless makeup application.

Most men typically don’t spend much time at all taking care of their faces. They don’t necessarily need to. But as a sissy, you will have to change your ways. The better you can get your skin looking good, the better your makeup will turn out.

It’s time to get intimately familiar with face masks, exfoliating scrubs and moisturizing/hydrating creams. The beauty industry is huge because women—and sissies—will do most anything in order to look their most alluring.


If you’re not blessed with a full, healthy head of hair an/or can’t grow it out, you’ll need to buy a wig or two. The great news is that there are a multitude of inexpensive, synthetic wigs that look fabulous.

Here’s the tricky part: They probably won’t look quite as good when they arrive at your front door as they do on the wig model on the website.

Sometimes wigs are good-to-go out of the box. Sometimes the bangs—if it has them—will need to be cut-in or styled. Since there are so many other things (like makeup) that sissies have to spend time on, I would advise getting a low-maintenance, easy-to-manage wig from the get-go.

Capable hair styling requires a skill-set not to be taken lightly. There’s a learning curve required that can eat-up a lot of time. You don’t need to be doing that at the beginning of your sissy career… unless you really want to. There will plenty of time to learn how to style hair later on.


sissy nail care

Nail care is another beautification item that seems to fall by the way-side in a man’s world. That’s not an acceptable attitude for a sissy. Nicely manicured nails will certainly enhance your femininity.

No need to go to a nail salon. Just some filing and shaping, followed up with a clear or matte coat of polish will make a world of difference in how you feel about yourself. And you want to feel as feminine as possible.

Not to be overlooked is the fact that having smoothly shaped nails, free from any sharp edges, will enable you to pull a pair of nylon stockings over your freshly shaved legs without the fear of running them.

Makeover Time

Sometimes, as a sissy, it can be difficult to visualize what your dollification potential actually is. When your makeup skills are in the formative stage, you will often not be able to get an accurate picture of the possibilities that await you.

Because of that, I recommend getting a makeover from a professional makeup artist. Sometimes, you can find a cosmetics expert at a makeup store or counter to do one for free. It can be quite inspiring—and motivating—to see how good you can actually make yourself look once you perfect your makeup application skills.

Developing Your Sissy Body

sissy body

After makeup, there’s nothing that will enhance your sissification efforts more than transforming your body into a slim and sexy one. You should aspire to becoming a skinny sissy.

There are many advantages:

  • When you’re slender, it’s much easier to pass as a girl
  • You can buy sexier, form-fitting clothes that will look fantastic on you
  • You will be much more desirable as a sexual plaything
  • If you’re an attention whore, you’ll get much more of it
  • You will look younger, feel better and live longer

If you want to be a skinny sissy, the easiest way to accomplish it is with your diet. As a former personal trainer I can tell you that weight loss is 80% diet. It’s time to change the way you eat sweetie.

Skinny Sissy Diet

Our culture has conditioned us to eat a diet high in crummy carbs. A crummy carb is ANY carbohydrate that is not a fruit or vegetable. Cutting those crummy foods out of your diet will work wonders.

Now would be the perfect time to check out The Sissy Weight Loss Manifesto where I go into great detail about how a sissy such as yourself can lose weight… permanently!

Sissy Webcam

In support of my writings, I recommend this program to learn how to eat like a sissy should.

Once you begin eating this way, you’ll never want to go back.

Booty Workout

To enhance the look of your slim and sexy body, you will want a bubble but sticking out the rear. A firm, round booty makes men’s cocks stiffen and women’s pussys twitch. As a sissy, that should be one of your prime objectives—to turn your admirers on. And keep them turned on.

Obtaining a beautiful butt will take a lot of work. To see what you need to do, head on over to 6 Sissy Butt Popping Exercises That Work. I spent tons of time researching that article and use these booty exercises myself.

To augment and speed up the butt building process, I recommend this amazing, no-bullshit program. It strips away all the ignorance and misconceptions surrounding how to develop an ass-to-die-for.

Sissy Waist Training

waist training corset

To be a super-feminine sissy, you will want to work towards that highly desirable and much coveted hour-glass figure. A wasp-like-waist with a bubble butt directly to the south is a tough combination to beat.

A skinny sissy diet will help slim down your waist of course. But to speed matters up, you will need to incorporate some type of waist training. I wrote about how to do that in The Sissy Guide to Corset and Waist Training.

Obviously, if you’re serious about developing your sissy body to its full potential, you will need to buy a corset or waist trainer. My favorite place is Bunny Corset.

A sturdy but stylish corset that will do the job while not falling apart in the process can be pricey. Bunny Corset’s pricing makes it affordable for any sissy to add a corset to her growing lingerie collection.

Are You Ready for Part 3?

Part 1 of The Complete Sissy Training Guide covered the nuts-and-bolts of the sissification process. It’s meant to serve as a primer on how to train a sissy.

This Part 2 took things to a deeper, more intense level. We went over:

  • Establishing Your Sissy Persona
  • Sissy Desire – Sexual Reprogramming
  • Your Sissy Slut Factor
  • Dollification – Beautification
  • Developing Your Sissy Body

Part 3 will take the sissification process to new—and even scarier—levels.

In Part 3 we’ll be discussing:

  • Voice Feminization
  • Socialization
  • Transition Education
  • Total Transformation

If you have the desire (and circumstances allow), Part 3 will inspire you to—and show you how—become a full-time sissy. You will begin to experience what it’s like to live a sissy lifestyle, along with everything that entails.

Are you ready for that princess?

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