Difficulty level: Beginner
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While a so-called fem-boi is perfectly happy to pull a pair of panties over his hairy ass, then spend 5 minutes (or less) jacking off to some sissy-porn, a more serious sissy is at the opposite end of the femininity spectrum.
Her desire is to turn herself into an incredibly hot, sissified slut—one that would make any GG girl drool with envy.
A true sissy is more-than-ready to play the long-game of sissification. She understands that total transformation into the fuck-doll of her dreams will take more than just a pair of pretty panties, painted toenails and a tube of lipstick.
She’s spent her entire life trying to be something she isn’t… a man. It’s going to take a good amount of time, effort and commitment to strip away all vestiges of her remaining masculinity.
We’re not talking about a remodel project—or even a renovation. This is going to take a complete tear-down and rebuild from the bones up.
To be both fair and honest, becoming completely sissified—from the inside out—is not for every sissy. There are a multitude of life-circumstances that can prevent many girls from going all-the-way.
This Complete Sissy Training Guide is for the sissy who is ready to hold her nose and fall backwards off the 10-meter platform. It will involve training tasks that may seem cruel, intense conditioning practices, and strict behavior modification.
If you’re really ready for some scary and super-serious sissy training, then you’re in the right place.
DISCLAIMER: once you reach a certain point in this sissification process, it will be pretty much impossible to turn back.
Sissy Training Basics
We’re gonna start at the very beginning. The basics of your sissification journey are not necessarily exciting and sexy . However they are mandatory. This sissy training guide will be—if anything—thorough. You’ll be guided along by taking one, small and perfectly placed high-heeled-step in front of another. The first of which will be your sissy name.
Your Sissy Name
I’ve noticed that initially, many sissies use a form of their male name for their sissy one. Mike becomes Michelle. There is absolutely nothing wrong with this other than it’s not very creative. To be honest, it’s taking the easy way out.
Why not spend some time online researching other possible names? Search for both first and last names. Not that you need a sissy last name at this point but last names can work as first names too. For example the last name ‘Maddison’ would also make for a cute sissy first name.
Your Sissy Email
Your email should also reflect your sissy status. Michael Brown—truckbuilderATemail.com—doesn’t quite sound like a sissy now, does it? Michelle—sissyfuckdollATemail.com—is much more appropriate. Your sissy email is basic stuff… so no questions, just go do it.
Financing Your Sissification
It’s going to take a modest amount of cash to get started with your sissification. Being a sissy will become one of your tip-top priorities. There are things like butt plugs, dildos, lip gloss and panties that a sissy absolutely must have to get started. You will need to budget these expenses in.
Start off by buying one pair of panties. Depending on the brand and style, panties will look and fit differently on you. That’s why it’s best to begin with only one pair. This will give you a good idea as to what style and size works best for you.
A good place to start your panty search is B2BODY (formerly Barbra Lingerie). Their panties tend to have a larger front panel to accommodate your soon-to-be-shrinking male anatomy. They also have an open-ended gusset/crotch liner that will be put to good use later on. Plus they’re on the fairly inexpensive side.
Serious sissy training requires that you track your sissification progress: in writing. You will need some sort of notebook or app to serve as your sissy journal.
Things such as: sissy habits, behavior changes, body measurements, weight loss and orgasms need to be documented. Your sissy journal will also be a handy place to keep a ongoing list of the feminine things you will need to acquire.
Take a break and spend some time to get these sissification basics in order before proceeding further.
It would be nice to flip a switch and instantaneously go from boy to girl. Unfortunately, years and years of male conditioning makes that virtually impossible. It will be necessary to re-condition and re-program yourself.
Transforming a male-mindset to one of an obedient sissy will require a complete brainwash. With enough work—and this sissy training guide—morphing from masculine to ultra-feminine is entirely doable.
To start off with, you will need a sissy mantra that you will be repeating to yourself often. One mantra to begin with is fine. Later, you will want to add others. Affirming who you really are is an essential part of the sissy conditioning process. Here are a few examples:
- I like being conditioned to obey
- Wearing pretty panties makes me horny
- Being girly and feminine is empowering
- Sexual denial is what I crave
- I need to look feminine and pretty
- I become aroused when I obey
To help you along, here is a free Sissy Mantra mp3 file that you can download.
Daily Sissy Arousal Ritual
A properly trained sissy lives her life in a continual state of low-level, erotic arousal.
This is in stark contrast to the way the typical male goes through life—experiencing the high of sexual anticipation and orgasm followed by the ambivalent low of the inevitable refractory period. Males are wired to act, more-or-less, like dogs.
A sissy is trained to behave in a much more refined, controlled and consistent manner. You will become a feminine form of grace and dignity, using your sissy-sexuality to make the world a more loving and accepting place to live.
In order to train yourself as a creature of compliance, it will be necessary to establish a daily arousal ritual. It’s time to put that pair of panties on princess.
First collect twelve photos of beautiful women and save them to your phone. They can be GG, CD, TG, sissies or a combination of the above. These pics should be of their entire bodies, not just their faces, and should epitomize of who you aspire to be. They will act as your sissy role models.
This is one of my sissy role models.
Now pick a 15 to 20 minute time segment, preferably at the same time every day. Tuck your cock—soon to be transformed into a limp, little clitty—down into your panties, between your legs. If your panties have an open-ended panty liner or gusset, this is the perfect place to stuff your clitty down into.
While scrolling through your photo collection of hot girls, you are to gently begin rubbing, or nubbing, the tip of your clitty with one finger only.
This nubbing is to be done only through the soft, sexy material of your panties. This arousal session will serve to condition you in three ways:
- You will learn to pleasure yourself in a feminine manner
- You will associate this pleasure with an image of who you aspire to be
- You will condition yourself to be aroused without achieving an orgasm
While performing this daily sissy arousal ritual—while repeating your sissy mantra—you want to eventually train your clitty to stay soft and limp. Although this will take some time to achieve, it is imperative that you begin to change how you have been conditioned to respond to sexual stimulation.
Sissy training will enable you to become aroused without needing to cum. Most women don’t have an orgasm every time they have sex. And as a sissy, neither will you! But it is not advised to go cold turkey. On the contrary, you will still get to experience orgasms—for the time being anyway.
Establishing an Orgasm Schedule
While nubbing your clitty, you will become super aroused. You will want to cum and you probably will. When you do, just make sure any leakage occurs while gently rubbing the tip of your clitty—through your panties—with the tip of one finger only!
It will be necessary for you put yourself on a STRICT sissy orgasm schedule. To begin with, it should be no sooner than one-week intervals. Establish one day of the week where you reward yourself for exemplary sissy behavior. If you cannot make it one week between releases, then you are not ready for this sissy training, simple as that.
At this seemingly too-early point of the sissy training process, it’s important to establish that there will be no more male-like orgasms allowed. No jerking off with a death-grip around your cock. No penetrative sex whatsoever. If your partner (if you have one) needs to be fucked; you can either wear a strap-on or find her a boyfriend.
At some point in your sissy conditioning phase, it will be necessary to extend the time between orgasms. Long-term denial greatly enhances sissification training as it places your psyche where it belongs: in a helpless, obedient, subservient and sissified state of mind. In support of this goal, locking your clitty up in a chastity device is encouraged—and in most cases, required.
In anticipation of this event, now would be a good time to get an idea of how to size yourself correctly for a chastity cage. You can use this helpful sizing guide to get familiar with the fitting process.
Long-term chastity means just what it says—Long. Term. Because of that inescapable fact, a properly sized and comfortable chastity device is of upmost importance.
You can expedite your sissy conditioning by listening to or watching sissy hypno files. If you prefer sissy training videos, you can find a wealth of them online.
The advantage of audio files is that you can listen to them anywhere and at anytime. I’ve made a list of several sissy hypno sites over on my Sissy Resources Page. Just scroll down to the Sissy Hypno section.
Most all women apply either lipstick or lip gloss to their lips everyday. You need to be doing that as well. If you haven’t already, purchase some lip gloss and begin applying it multiple times per day. This is one more subtle way to augment your sissy conditioning program.
Fashion Magazines and Sites
It’s imperative that you begin reading women’s fashion magazines on a regular basis. They will give you fashion and makeup ideas that you otherwise wouldn’t be aware of.
Of course there are sites such as Pinterest where you can glean fashionable ideas from too. But having few ladies magazines around the house will make you feel like… a lady.
This is a partial list—with links—for sissy fashion ideas:
- Marie Claire
- VIVA (Japanese)
- Cromos (Spanish)
Get Your Ears Pierced
Get Your Ears Pierced
There is absolutely no excuse for any sissy to not have her ears pierced. Even if you’re still presenting as a male to society, it’s perfectly acceptable for men to have pierced ears now-a-days. If you’re serious about your sissification—and you should be if you’re going through this sissy training guide—then just go get it done.
Under no circumstances, do not have your ears pierced at the mall where they blast through your earlobes using an ear piercing gun. You want the piercing done with a specialized hollow piercing needle. These needles actually remove a minuscule, circular section of ear tissue, making a clean, round hole.
If you don’t want to incur the expense of going to a professional ear-piercing studio, it’s easy enough to DIY at home. Sterilized, 16 gauge piercing needles can be purchased online as well as 16 gauge stainless steel piercing studs. I like to use a 16 gauge needle as it leaves a nice-sized hole to accommodate various sizes of earrings for later on.
Don’t believe the popularly-parroted opinion that you should only have a piercing professional perform this job. Nothing could be further from the truth. This is not rocket science. Here is a YouTube video to prove it:
The one thing that she doesn’t do in the video—and what I always do—is to use an ear piercing stud that is sized to to fit inside the piercing needle. Then, after you have the needle through the ear, simply place the stud inside the non-pointed end of the hollow needle and push everything through, all in one smooth motion.
Doing it this way doesn’t give the hole time to close up before you can get the earring through.
The main mistake most sissies make when piercing their ears is that during the aftercare phase, they tend to play around with the studs too much: incessantly turning and fiddling with them. Other than cleaning them with rubbing alcohol or hydrogen peroxide everyday, just leave the piercings alone and let them heal up.
As a sissy, it’s imperative that you have a smoothly shaved body. Just like with ear piercings, no one bats an eye these days over a man who shaves all over. Remember, this is all about conditioning you to think and act like a girl.
Girls don’t have hair all over their bodies. Ladies, at the very least, shave their legs, armpits and pussys. Sissies shave their entire bodies.
There’s no nicer feeling than pulling a pair of nylon stockings over freshly shaved legs. First shave your legs; then get the nylons here.
Sissification is all about turning yourself into a girly-girl. So it’s time to start acting like one. If you need some shaving and/or hair removal pointers, I wrote an article about each:
Sissy Nail Care
It’s time to begin taking care of your nails; just like a girl would. Oh, you already are a girl so it’s just a matter of matching what you look like on the outside with what’s going on inside of your pretty little sissy head.
Begin by letting your nails grow out to the end of your fingertips. That’s not so long as to affect your everyday life in any way. Then you will need to keep them filed and shaped. Applying a clear, matte polish will be the final touch.
Your nails need to look as well-kept and feminine as any GG out there. Keeping the ends smoothly filed will prevent your from running your nylon stockings when pulling them up over your smoothly shaved legs.
Begin Growing Your Hair
If you have enough hair on your head, it’s time to begin letting it grow. As with pierced ears and shaving, there are plenty of men who wear their hair long—so you can too.
It takes a while for hair to grow out, so no one will really notice that much. You can keep the ends trimmed so it looks under control. When it gets long enough towards the end of your sissy training, you can practice styling it.
If you’re not lucky enough—or young enough—to have have thick enough hair, then that’s why most sissies wear wigs.
Anal Stimulation and Stretching
You will need to condition your sissy pussy to comfortably accept penetrative devices. There are three reasons for this:
- You are no longer a sexual penetrator but now a sissified, sexual receptive
- Even if you’re a sissy who is not into men and cocks, much of your sexual pleasure will be coming from dildos and vibrators
- As your sissification training intensifies, your erogenous zone will naturally begin to move backwards, from the base of your former cock, across the perineum, to your sissy pussy.
No matter how tight and inexperienced you happen to be right now, it’s entirely possible—and even mandatory—to stretch things out down there so you can accommodate whatever may come your way. If that happens to be a well hung hunk, then you will need to be able to take him in without too much distress.
A good place to start is by inserting a butt plug during your daily sissy ritual. Having something in your pussy, repeating your sissy mantra while nubbing yourself through your panties will condition you to associate sexual pleasure with being penetrated.
Once you get used to wearing a butt plug, you will need to upgrade to a dildo. Don’t buy the biggest one as it will take some time to stretch your pussy out. Go for something small-to-medium-sized, then size-up later. You can find a nice selection of dildos over at TooTimid.
Towards the end of your sissy training, you will be more-than-eager to have your pussy filled up. Eventually, you will come to crave it.
A Flat Feminine Front
It is imperative that a sissy present a flat feminine front to the world. Depending on how big (or in your case, small) you are down there, it may not be necessary to incorporate any sort of sophisticated tape tucking system or to buy a fancy gaff in order effectively hide things.
Do you remember earlier about how panties are designed with a crotch liner or gusset? Most of the time the panty liner is of the open-ended variety. This narrow liner provides the perfect place to tuck your limp clitty down into.
It’s also possible to push your nuts back up and into the sockets located inside your abdominal cavity. Yes, there is a place where your balls used to live—before they dropped down—and can still be used to temporarily hide out.
If you aren’t able to accomplish this for any reason (such as a hernia patch), no worries. You can pull your nuts up near the top of your panties and it will give you a sexy camel-toe look. Don’t be too concerned about becoming aroused while being tucked as that doesn’t typically happen when you’re being restricted like this.
Besides, after listening to lots of limp clitty training hypno files, having a small, soft clitty will become the new normal for you.
To help motivate you in that downward direction, this Itty Bitty Clitty mp3 file will inspire your clitty to be what it was meant to be—perpetually limp… and useless.
With your clitty tucked down and away, inside your panty liner, you should be good to go; except maybe to the beach. If you’re gonna be wearing a bikini bottom then you will most-likely need to tuck using tape.
Here’s a YouTube video explaining how to do just that:
Now that your sissy conditioning is well under way, we can turn to outward matters: how to properly physically present yourself as an ultra-feminine sissy.
Sissy Poise, Presence and Comportment
Sissy Poise, Presence and Comportment
While many sissies concentrate on makeup and fashion—as well they should—it’s also important that you learn to move and act in a feminine manner. Women carry themselves differently than men do. They tend to move with grace and fluidity, whether it’s washing the dishes or walking down the street.
Going to the bathroom could just as well been put under conditioning as sitting to pee will make you feel like a girl. Might as well get used to it. So start making it a habit to pull down your panties and pee in the gender-appropriate fashion.
When you have yourself looking good enough to venture out in public, you will be using the women’s restroom and you will definitely have to sit to pee in there.
Hopefully you’ve noticed that women eat differently than their male counterparts. They eat in a more delicate and unhurried manner. Also, their portions are much smaller than manly-sized-pig-like helpings.
Girls also open their mouths wider and use the teeth to pull the food from the fork or spoon. This lady-like eating technique will keep your lipstick on longer.
Next, girls eat slower by taking smaller bites, then chew those smallish bites for a longer time. In between bites, women place their utensil back down on the table—slowing the eating process down even further.
Lady’s are acutely aware of how to properly hold a knife, fork and spoon. It’s always in a light, dainty manner; never in a cave-man-like grip.
Lastly, when drinking, women hold the glass or cup with the thumb and first two fingers only. The last two fingers are femininely flared out, never touching the glass.
Proper sitting posture is a dead-give-away as to your gender. Sissies should always enter the sitting position with a straight back—then keep it straight-as-a-board while sitting.
If you’re wearing a skirt or dress, then you want to lightly spread your dress out under your ass before settling into the seat of the chair or couch. This helps to keep wrinkles from forming in the material.
While in the sitting position, your legs should be either crossed or angled off to one side with the knees together. Never, never, ever, sit with your legs open—even while wearing jeans—or with one ankle crossed over the knee like a man.
This video will show you how to sit elegantly, like a lady:
The feminine form is all about proper posture. Girls stand with their shoulders pulled back, the pelvis tilted slightly forward and the legs straight. This naturally pushes your breasts out, showing them off in a not-so-subtle manner.
Your arms can be left lightly dangling at your sides, palms facing forward. One hand can be placed on the hip—but never both! It’s also permissible to lightly fold your arms together in front of you.
The feet should be positioned with one foot slightly forward, placed at a 45 degree angle. Standing with both legs wide apart is considered a dominate stance and never appropriate for a sissy.
Bending down—or squatting—to pick an item up, or to get a better look at something placed at a lower level, requires the proper technique. Sissies should never bend at the waist. Although that might be the easier way—especially while wearing heels—it’s not the feminine way to do it.
Just like sitting, bending should be done with the back perfectly straight and the head up. You can glance down with the eyes in order to see what you’re picking up while still keeping the head up.
Walking in Heels
The feminine walk begins with the standing posture mentioned above; shoulders back with the pelvis tilted forward. We’ll talk about walking in high heels since a sissy should eventually reach the point where she’s wearing heels 90% of the time.
Assuming the feminine-like stance already mentioned above, simply walk in a straight line, one foot placed directly in front of the other. These are short-carefully-placed-steps, allowing the heel to contact the ground slightly before the ball of the foot comes down.
The leading front leg should be perfectly straight (knee locked) when the foot makes contact with the ground. The elbows should be lightly pressed to the sides of the body while the forearms sway lightly, fore-to-aft, with the palms facing slightly forward. The gaze is fixed confidently ahead to where you’re going—not down at the feet.
Confidently strutting about in heels is the hallmark of femininity. Not many will question your gender when you can walk properly in heels. Here’s a video you should watch:
Females carry themselves with a smooth and gentle grace that is the antithesis of masculine. Be aware and watch how girls confidently move their bodies. Whether it’s sitting, standing, bending down or walking; modeling—and then mastering—feminine gracefulness should become an obsession with you.
Sissy Elegance and Refinement
Female Body Differences
Realizing the differences between the female and male body will help you to understand the feminizing measures that must be taken to overcome these shortcomings.
Obviously, a girl typically has wider hips and a smaller waist that gives her that coveted hourglass figure. She also has narrower, more delicate shoulders.
For the face, she—for the most part—doesn’t have much facial hair to deal with. A woman also has a smaller head, a narrower jaw and chin, and a much less prominent browline. Much of your facial-feminine-shortcomings can effectively be taken care of with skillful application of makeup.
Makeup will be covered extensively in Part 2 of this Complete Sissy Training Guide.
It’s important for a sissy to establish a body benchmark so as to track her feminine refinement progress. Obtain a cloth or fabric tape measure and record:
- underbust (necessary for bra sizing)
- left and right thighs (separate measurements)
- upper arms
You will want to re-measure every couple of months so as to track your progress. As you lose weight while working out your booty in the quest for that beautiful bubble-butt-of-your-dreams, those measurements will be changing in the proper direction.
Once you have figured out what size and style of panties you prefer, it’s time to buy at least seven pairs—one for each day of the week.
From this point forward, you’ll be wearing panties every day and also to bed every night. No exceptions! This is important to firmly implant your femininity into your psyche.
Bra and Breast Forms
It’s also time to buy your first bra. Like panties, purchase just one at first so that you can dial-in your proper size and preferred style. Be aware that lingerie companies size their bras differently. One size from one brand does not necessarily mean it will fit the same as another brand.
With those things in mind, here is a bra size calculator—for sissies—that will help immensely.
Not too-many things will make you feel more feminine than a set of silicone breast forms. Upgrading from stuffing your bra with panties or nylon stockings will make a HUGE difference with how you feel about your femininity. Although these do not need to be expensive, buying the best quality that you can afford is being sissy-smart.
Newer, less experienced sissies tend to over-do things in the size department. In reality, a ‘B’ cup is usually plenty big enough. Tits tend to look bigger under a tight fitting sweater or blouse.
Anyway, buy your bra, then get appropriately sized forms to fill it out. For me, a set of breast forms were the best girly thing that I ever bought—and that’s coming from a high heel fetishist.
Padded Butt and/or Hip Enhancers
One hindrance to your sissification process will be the inability to make your hips wider through diet and exercises. Your butt is an exception, but it will take a metric-ton of work to turn it into a bad-ass-booty.
To help achieve that much-sought-after-bubble-butt, you can buy butt-lifting and hip-enhancing shapewear. Although not inexpensive, these sissy things can make a big difference in how you present your ass to the public—or to your mirror.
A great site to see what’s possible is over at LoveMyBubbles.
Sissy Workout Outfit
In order to refine your femininity, it’s imperative that you improve the look of your body. That means exercise. Since you’re going to be working out anyway, you might as well do it in sissy-style.
All you’ll need is a nice pair of exercise tights and a sports/workout bra. These will make you feel super-feminine while you’re developing a more more feminine-like figure.
You can use your newly acquired workout clothes to do yoga. Practicing yoga will take your femininity to a new level. You’ll become more flexible—like a girl is—and learn to move more gracefully.
If you can’t join a yoga studio, it’s easy enough to practice yoga at home. There are way-too-many awesome YouTube yoga channels to mention here. It’s also well-worth reading my article: 7 Reasons Why Every Sissy Should Practice Yoga.
As already noted above, men have a protruding browline. You can make that part of your face less prominent—and much more feminine looking—by shaping your eyebrows. Buy yourself a quality pair of tweezers and start tweezing away.
Yes, it might hurt a little but… beauty is a bitch. Always tweeze from below. You’re going for a high-arching brow, which means that you want to leave the upper hairs while removing the lower ones.
Nothing is more important to refining your feminine look than makeup. You don’t need me to be telling you this, but you do need to begin practicing. Genetic girls have spent most of their lives practicing makeup everyday. No wonder they’re so damn good at it!
Just doing your makeup once-per-week will enhance your femininity significantly. It will take some time to get good, but good you will get. If you’re serious about sissification, then becoming skillful at applying makeup is non-negotiable.
Head on over to YouTube and start watching makeup tutorials. Decide what look you’re going for, then take a couple of hours each week and begin practicing. Here’s a video to get you started:
You can get a multitude of makeup and fashion ideas from reading women’s fashion magazines. I already gave you a list of them (with links) earlier in this article. You can read them online but it’s a good idea to have a few hard copies around the house. They will make you feel girly just seeing them laying around.
Fashion magazines have a way of presenting clothes, shoes, makeup and fragrances in the most appealing manner. They are marketing geniuses at making a girl feel beautiful and sexy; and those are exactly the type of elegant, feminine feelings you want to instill in yourself.
This is the End… of Part 1
You’ve come a long way sissy. Up to this point we’ve covered:
- The Sissy Basics
- Sissy Conditioning
- Sissy Poise, Presence and Comportment
- Sissy Elegance and Refinement
Part 2 of The Complete Sissy Training Guide includes:
- Establishing Your Sissy Persona
- Sissy Desire – Sexual Reprogramming
- Your Sissy Slut Factor
- Developing Your Sissy Body