In Part 1 of The Complete Sissy Training Guide, we covered the basics of sissification. Think of it as your starting point—those fundamental skills you need to get ready for the more advanced stages of your transformation.
Just like a soldier begins with the basics before dealing with tough tasks or a college student handles general studies before jumping into their major, you need to perfect these girly essentials first.
Before we move on to the next level of feminization, let’s take a moment to focus on something truly personal—your own unique sissy persona.
Your Sissy Persona
Men, whether it’s how they’re born or what society has drilled into them, are trained to act in a way that is far from what you, as a sissy, should be. They’re taught to be tough, quick to judge, and rarely care about listening to anyone. Dominating, achieving, and taking – that’s their thing. They love being right.
But not you, sweet one. You live with softness and grace. You listen with kindness, respond with thoughtfulness, and never rush to judge. Understanding? That’s your true goal.
When things get heated, you don’t fight. You find a way to make peace, to compromise, to smooth things over. You know that being submissive isn’t weakness, but the path to a calm, beautiful outcome. You don’t need to argue or be right. You’re just here to please and be at peace.
In this world, your role, darling, is to give – to please, in whatever way is needed. You’re not about taking, but offering yourself. You aren’t afraid to show your vulnerability, especially with other women. And if you need help, you ask without hesitation.
While men may take the lead in certain ways, you, as a sissy, know that you are happiest being the one who receives. Now, with your new, blossoming sexual nature, we’re going to begin the journey of reprogramming your desires and responses. This is just the beginning of your beautiful transformation.
Sissy Desire – Sexual Reprogramming
To continue the sissification process, it is crucial to eliminate any remaining masculine desires from your mind. This can be achieved by regularly listening to sissy hypnosis files every day.
Sissy Hypno
Oh, sweetie, if I could just bitch slap that masculinity out of you, I would, but for now, we’re going to go with something a little more effective—sissy hypnotic files. You’re already familiar with these from Part 1 of your training, so don’t act shy.
I’ve put together a list of sissy hypno sites over on my sissy resources page. Just scroll down to the “Sissy Hypno” section, and you’ll find them waiting for you.
The whole point of sissy hypnosis is simple: we’re going to program you to think, act, feel, and truly be more feminine. This isn’t just about looking the part—clothes, makeup, heels—oh no. It’s about rewiring your mind so deeply that any trace of masculinity fades away, leaving you unrecognizable as the man you once were.
Sissy hypnosis will shift your gender identity to the feminine side, and trust me, your sexual responses will follow quickly. As you dive deeper, you’ll start to embrace and even crave a small, useless sissy clitty, along with a growing desire for anal pleasure. With these hypnotic audio files guiding you, you’ll transform into a submissive, sexually receptive little sissy.
So, darling, if you want to know exactly what you’ve gotten yourself into, go ahead and download that file. Listen to it. Now.
The next step will be to…
Learn to Pleasure and Release Like a Girl
Listen up, darling. It’s time you learn how to pleasure yourself like a true feminine, girly goddess. You might already know how men reach orgasm—quick, rough, and loud—but that’s not how a proper sissy behaves.
We girls take our time. Our pleasure is soft, sensual, and builds up slowly. An orgasm for a woman isn’t just a burst of force; it can be gentle, tender, and all-encompassing, spreading through your body in the most delicate ways. Sometimes it’s explosive, other times it’s a soft wave of bliss.
To truly cum like a girl, you need to get yourself ready—mentally and physically. Remember, darling, the mind is the key to unlocking your feminine pleasure.
Alright, darling, here’s how it goes:
Set aside a nice 30-minute window just for yourself.
Always make sure you’re wearing at least a bra, panties, and your favorite heels—got to look the part, right?
And from here on out, you’re going to always have something in your pussy—this is key. Associate your pleasure with some sweet, sensual anal play.
Tuck your clitty down into your panties, sweetie.
Now, settle in and listen to your sissy hypno, or watch an erotic video that gets you in the mood.
With one finger, gently play with the tip of your clitty.
With the other hand, tease those nipples or run your fingers over your soft body, feeling every curve.
As the pleasure builds, let out soft moans like the sissy slut you are.
If your clitty starts to stiffen up, stop for a moment. Don’t rush. Let it soften back down.
Forget about any specific outcome. Just let yourself enjoy the feminine pleasure, feel every second of it.
If you release, great. If not, that’s perfectly fine too, darling.
As you do this more often, you’ll start to crave a more feminine release, and over time, your clitty will learn to stay soft, even when you’re at your peak. No need for those messy, masculine climaxes anymore. It’s just not lady-like.
Sexual Denial
Men are often shallow, self-centered creatures who just want quick pleasure. It’s a fast, empty way to live.
But for a sissy, life is all about denial—staying on edge, always a little frustrated, which only makes her more feminine and submissive. She loves the feeling of being constantly aroused, ready to please, but never fully satisfied. That’s the way she was meant to live.
When a sissy finally gets to release, it’s something she treasures deeply. Until then, she gets lost in the feeling of her clitty twitching in her panties while she applies her lashes and lipstick. She loves to fantasize about the sexy lingerie and heels in her closet, letting herself feel the frustration while savoring the aftermath of a ruined orgasm.
For a sissy, this kind of life often means the help of a chastity device. Few things train a sissy like a well-fitted cage, ensuring long periods of denied pleasure, sometimes forever.
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
For an added level of eroticism and thrill to your chastised lifestyle, why not turn it into a game? All you need are two dice. You, or preferably the person in control of your chastity device, roll a pair of dice–one black and one white–to determine the length of time you will be locked away.
I describe how this chastity dice game works in more detail in 7 Fun Sissy Chastity Games.
Attempt an Anal Orgasm aka Sissygasm
The ultimate goal of your transformation is to experience pleasure in a way that only comes from deep, sweet anal stimulation. This is what we call a sissygasm, and trust me, it’s far superior to anything you’ve known before. As you progress, your sissy clitty will become limp and useless – it’s there, but all it does now is leak when you’re aroused, giving you nothing more than a reminder of your true nature.
Achieving a sissygasm takes time and dedication, but once you reach it, you’ll never even think about those old, manly orgasms again. In fact, after a powerful sissygasm, you might just forget you were ever a man to begin with.
Your Sissy Slut Factor
Your transformation is all about discovering a pleasure like no other – the kind that only comes from deep, sweet anal stimulation. This is what I call a sissygasm, and believe me, it’s so much better than anything you’ve experienced before. As you progress, your sissy clitty will become limp and practically useless. It’s still there, but all it does is leak when you’re aroused, serving as nothing more than a reminder of who you truly are.
Reaching that sissygasm takes time and commitment, but once you experience it, those old, manly orgasms will be a distant memory. After a powerful sissygasm, you might even forget you were ever a man.
Sissy Chastity
In the last section, I had you practicing a little “lady-like” fun with your clitty, just teasing through those panties. It was cute, but that’s only the beginning of your transformation.
Now, we’re taking things to the next level, and trust me, you’re going to love this. To really dive deep into the sissification process, we need to bring in some real discipline. That means no more playing with yourself, no more teasing your clitty through your panties. It’s time for a chastity device, sweetie. I’m serious—you’re going to need one. Time to lock that clitty down for at least 7 days, princess.
Why, you ask? Because you’re going to live in a constant state of erotic denial. This will build up your desire and energy, driving you toward becoming a truly dedicated sissy. Remember, that tired refractory period after you orgasm? That’s for boring, undisciplined men. You’re not a man anymore, darling. You’re something much better.
By denying yourself, you’ll channel all that energy into your growth as a sissy. It’ll make you better, not just as a sissy, but as a person too.
And if you don’t have someone to hold you accountable, don’t worry. I’ve got a little technique in The DIY Sissy Chastity Keyholder Method that will help you out.
The ultimate goal here, sweetheart, is to take that clitty, that little thing you’ve been clinging to, and strip it of its power. We’re going to make space for something truly feminine—your sissy pussy. Ready to begin? You better be.
Dildo Training
By now, you should’ve accepted that your pleasure is all about that sweet anal stimulation. If you haven’t already, it’s time to get yourself a dildo—something that’s the right size, not too big or small. It should give you just the right amount of discomfort at first.
But don’t stress, you’ll adjust in no time. Remember, part of your sissy training is all about stretching and opening up that tight little sissy ass. Keep going, you’re doing great.
Practicing Blowjobs in the Shower
Many dildos come with a handy suction cup at the base, so you can easily secure it to the floor for some practice. It works even better in the shower, where the wetness helps it stick perfectly—whether on the floor or against the wall. Stick it to the wall, lather it up, bend over, and let it slide in. Once you’re in, turn around, drop to your knees, and show me how much of a sissy slut you’re quickly 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.
Sissy Training Guide – 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 guide you in becoming a desirable sissy – attractive and pretty to the max. Natural-born women spend an exorbitant amount of time and money on their appearance. As a princess, you will need to put in even more effort if you want to be beautiful. It may be impossible to completely replicate the look of a woman who is a master at beautifying herself, but you can certainly make yourself presentable.
The good news is that there are many natural-born women who, for unknown reasons, do not put any effort into looking feminine and sexy.
A motivated sissy like yourself can fill this gap in the world of femininity by following a dedicated 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.
Makeup
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 Reneereyes.com.
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.
Wigs
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.
Nails
In the realm of male-dominated activities, nail care is often neglected. But that’s not a mindset a feminine person should adopt. Well-groomed nails can greatly enhance one’s femininity.
No need to visit a nail salon; a simple filing and shaping session, followed by a clear or matte coat of polish, can make a huge difference in how you feel about yourself. And feeling as feminine as possible is important.
Additionally, having smoothly-shaped nails with no sharp edges will prevent your freshly shaved legs from snagging on nylon stockings.
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
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!
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
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.
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 of our Sissy Training Guide?
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 Sissy Training Guide Part 3, we’ll be discussing:
- Voice Feminization
- Socialization
- Transition Education
- Total Transformation
Are you ready for that princess?
