Transforming yourself into the sissy of your dreams can be one of the more exciting and erotic adventures you will ever embark upon. It can also seem overwhelming at times. I mean, here’s just a partial list of things that go into the making of a sissy:
- hair removal
- weight loss
- makeup, hair & nails
- walking in heels
- acquiring a wardrobe
- developing feminine mannerisms & voice
- moving beyond male orgasms
- learning to cum like a real girl
All this can make a pretty girl’s mind become blurry behind a cloud of disarray.
And of course, we want all of those sissy things right NOW!
At some point though, your sissy fantasies will come face-to-face with bare-knuckled reality.
The truth of the matter is that your sissification will be a process. A sometimes intense, frequently challenging, but extremely satisfying journey that isn’t going to happen overnight.
Becoming a serious sissy will give you a healthy appreciation as to how much work is involved for a genetic girl to look as good as she does. As a sissy, since your starting off with a boy’s body, you’re gonna have to work even harder than your female counterparts.
The proper sissy perspective is to learn to accept and enjoy the entire sissification process.
When you see a photo of a drop-dead gorgeous crossdresser, it can be illuminative to view her as an iceberg. You are only seeing the top 10% of her, the part that shows.
What isn’t readily apparent is the time she’s spent dieting, exercising, applying make-up, enduring laser hair removal treatments or how many cocks she’s had to suck in order to afford the expensive lingerie and high heels that she’s wearing.
It’s the same with you. Snapping your fingers (with their prettily polished nails I hope), and magically transforming yourself into the perfect sissy would take all the fun and excitement out of things.
It would be like showing up before the start of a football game and have the PA announcer proclaim that instead of playing the game, the final score will be 24-20… everyone can go home now. Both the players and the fans would exit the stadium feeling frustrated and cheated out of experiencing the excitement and drama of how that final score came about.
So, in the spirit of appreciating and enjoying your sissification, let’s take a brief look of how the process might play out, for each of the above checked items.
Sissy Hair Removal
Keeping your body smooth and sexy typically starts with shaving your legs. Many male athletes shave their legs on a regular basis so this will not draw any unusual attention to yourself. It only takes about five minutes… once you get good at it.
The next logical progression would be to shave your entire body. This is becoming much more widely accepted now-a-days so any hang-ups you have about it are in your head and no one else’s.
We’re talking anywhere from ten to fifteen minutes to shave all over but as your sissification process intensifies, it’s a commitment you’re more than happy to submit to. Once every week or so will be often enough, but going longer in-between shaves can definitely turn it into a chore—as well as increase the time it takes.
I eventually began to shave two or three times per week. The shorter the hair, the quicker and easier shaving becomes. By shaving more often you can enjoy having a silky smooth body most all of the time.
Many sissies will stop at shaving but the next step in the process would be to remove the hairs from their follicles by either waxing or epilating. I have personally moved on to the epilator.
Epilating will take some getting used to, especially for the chest area. Hair grows in cycles, so when you’re shaving, all of the hairs are front-and-present at the surface of the skin. Once you begin to epilate though, you will only be dealing with around one-third of them at any one time.
That’s the reason that in between epilating sessions, the hair that grows back will be less dense. Also, since you’re no longer blunt cutting the hairs off with a razor, the hairs will be and feel finer since the virgin, un-cut tips will be pointier and thus narrower.
If you choose to epilate, the first time is the worst as you will be pulling all of the hair from their follicles at once. Subsequently, things get much easier as you’re only dealing with one hair growing cycle at a time. Plus, your skin (and follicles) will adjust appropriately, making the procedure much more bearable.
Don’t believe in the myth that using an epilator will leave your skin hair free for two to three weeks at a time. In my experience, that’s not the case. I have settled into a routine of epilating once per week and then shaving afterwards.
Epilation doesn’t get every single hair, plus you won’t want to let that devious device come anywhere near your private parts, so shaving is still a necessity. Still, my once every week epilating/shaving ritual pretty much leaves my skin smooth and silky for the whole week.
The final step in the sissy hair removal process would be, of course, undergoing a more permanent procedure—either laser treatment or electrolysis. If you’ve got the money, that may be the best way to go.
Weight Loss For Sissies
Other than makeup, nothing will make you look more beautiful and convincing as a sissy than a slim, trim and sexy body. Like everything else about becoming the best sissy you can be, losing weight is definitely a process.
A really great way to begin that process is with this program. It shows you a different method of eating that is an extremely effective way to shed unwanted pounds. It’s the way I eat now.
Look, just about any sissy (or anyone else for that matter) can lose 20-25 pounds in two or three months buy eliminating all crummy carbs from their diet. 99% of the time however that weight WILL eventually come back on. Why? Because to keep the weight off permanently, the image you have of your ideal sissy weight must match (be in vibrational alignment) with what you really think is possible for you.
It can be incongruent for your inner-self to bridge the reality gap between a 185 pound macho man and a 135 pound svelte sissy. It’s problematic to reconcile that large of a discrepancy between your current weight and what you would like to tip the scales at in a more feminine form. The psychological term for this is ‘cognitive dissonance’.
Instead of trying to radically change your inner-most held beliefs about your body weight (which closely coincides with what you weigh right now), it’s much wiser to make it a long term—are you ready for this?—process.
Numerous studies have shown that if you can manage to stabilize your weight for a year, that weight will become your new norm and will likely stay off permanently. It works because you now hold a justifiable inner-belief that this is what you’re supposed to weigh… because that’s what you actually have weighed for an entire year!
Being able to compartmentalize your weight in 10 pound ‘stages of stability’ seems to work well. Allow me to use myself as an example… again. In 2017 my scale showed me in the 150 pound range. Most of 2018 saw my weight in the 140’s. 2019 arrived and I now weigh-in at 135. For my 5’7″ height, I think I’m looking pretty damn good! By the time the end of 2019 rolls around, I’ll hopefully be a perfect (for me) 127 pounds.
If you want to be a slim and sexy sissy, you may want to adopt the mentality of Kate Moss:
“Nothing tastes as good as skinny feels”
Sissies and super models have something in common. They’re both willing to starve themselves down to achieve the desired—and required—look.
Sissy Makeup, Hair and Nails
If there’s one thing that can make-or-break a sissy it’s her makeup.
If there’s one thing about sissification that screams ‘process’, it’s makeup. If you’re not working on perfecting your makeup skills on a consistent basis, then your results in that department will be marginal at best.
Think of it like this… if genetic girls are practicing putting on makeup everyday for years, how are you going to get really good with a once-a-month routine?
Start regularly watching makeup videos on YouTube. Take notes. Buy more makeup. Decide on the sissy image you want your face to project. Promise yourself that you will practice getting that sissy face of yours all dolled up once a week for a year. Do this and you will be amazed by how hot you will become!
Most sissies start off with a cheap, costume type wig. They then graduate to a more expensive, synthetic—maybe already styled—hairpiece. It’s fine to stop here as there are a multitude of moderately priced synthetic wigs now available that are truly stunning.
The next step up with the hair process would be a human hair wig. I recently bought a Remy Hair wig on eBay and didn’t realize that many wigs that don’t come pre-styled will need to be ‘cut-in’. The bangs may be too long for your liking or there may just be too much hair, especially in the front, that makes styling it impossible or at the very least, unmanageable.
If you don’t know what you’re doing, please don’t try to cut your new wig yourself! Make an appointment with a hairstylist, preferably one that has some experience with cutting wigs, and let them take care of you. I had to climb out of my comfort zone to make an appointment with a stylist to cut-in my wig-with-too-much-hair… but it turned out to be no big deal. Allowing yourself to be uncomfortable at times is just part of the process of being a sissy.
If you want to feel ultra-feminine on a daily basis, upgrading your nails will add an extra—and necessary—touch of class. Push the cuticles back and then let them grow out a little longer. Then file the sides so they look narrower and more lady-like. Finally, shape the tips to your liking.
Having a bit of white showing beyond the tips of your fingers—french style—looks oh-so feminine. If your daring, put a coat of clear-matte polish on them and… dare someone to say something.
High Heels and The Sissy
As a sissy, one of the most important requirements you should have for yourself is to foster an addiction for high heels. Ideally, you should become so comfortable wearing them when standing, sitting and walking, that you feel weird not wearing them.
There is no article of feminine attire that is more gorgeous than a sexy pair of high heels. But then you gotta be able to stand up and walk in them.
Many women advise a process of starting off small, with a 2 inch heel. Then gradually working up to 3 inches. Finally, when your ready, graduate up to 4 inch heels. But remember, these are real girls doling out this advice.
To begin with, no sissy worth her shapely shaved legs should ever put her pretty little feet into a pair of heels anything less than 4 inches tall—and I’m not talking platforms sweetie!
Also, I’m going to turn conventional high heel wisdom on its heel. I recommend starting off with 5″ heels, and then practice walking in them like there’s no fucking tomorrow. Your ‘stiletto skills’ will improve faster than you would think, if you strut around in them on a regular basis.
Concentrate on perfect high heel posture:
- shoulders back
- tilt the pelvis—to a neutral position
- activate the core—tuck your tummy in
- elbows should be lightly touching sides—palms turned slightly forward
- land with a slight heel-to-toe
- keep legs straight—front knee locked on landing
- take small, mincing, sissy-like steps
- walk in a perfectly straight line with one foot directly in front of the other
Once you’ve mastered a 5 inch heel, wearing 4 inch pump will be like taking a stroll in the park—which you will be able to do—if you follow this process. For an exemplary example of impeccable high heel form, watch Claire Underwood (Robin Wright) in Netflix’s “The House of Cards” confidently strut about the oval office in her heels.
Your goal is to learn to walk better in high heels than 90% of genetic girls. To be blatantly blunt, that won’t be too difficult for you to accomplish.
Dressing Like a Sissy — All Those Beautiful Clothes!
Dressing the sissy part is mostly a process of consistently adding to your girly wardrobe. Buying bras, panties, nylons, heels and dresses; not to mention accessories such as jewelry, purses and what-not is an expensive proposition, if you haven’t already noticed.
The fun part about acquiring feminine articles of clothing is that the more you buy, the more you want. One pair of panties leads to a pair for every day of the week. Bras beg for breastforms—one of my most cherished purchases ever, BTW. A pair of high heels can, and should, lead to at least a dozen more. Pretty dresses are to die for and you will want several in your closet.
Speaking of which… the inside of your closet will take on a process of metamorphosis. At first your male clothes may outnumber your girly stuff by 10 to 1. But that’s gonna change sweetie. That ratio should constantly be tilting toward the feminine. Begin by getting rid of all male clothing that you haven’t worn in a year. You won’t miss it.
Now you have plenty of room for your new sissy wardrobe. That ratio—male-to-female— will even-out at 50/50 before too long. Eventually your closet will be 90% filled with with ultra-feminine sissy things. Your panty-encased clitty should be twitching at that thought.
I hate to bring this up, but along the way—unfortunately—you will most likely go through a ‘purging process’ where, in disgust, you hide/put away and maybe even throw out or give away your girly clothes.
Don’t you dare do it sweetie! Purging is a normal part of the sissification process. It will pass. The overwhelming urge to be the sissy you were born to be isn’t going anywhere for long—it will return—usually with a vengeance.
Try to maintain a sense of maturity about the matter, and be ready to resume the process of buying even more gorgeous clothes when your sissy desires return… as they always do.
The Way They Walk — The Way They Talk
Sounding and acting like a girl is a process all of its own. Girls stand, sit, walk, cross their legs and eat differently than boys. As a sissy you’ve got some catching up to do. Perfecting a girly posture and adopting feminine mannerisms will take some time. Moving and acting as a male for most of your life will take some informed education and conscious re-wiring on your part… but it’s definitely doable.
Talking like a lady will probably be more challenging, but just like everything else about becoming a sissy, if you’re serious, you’ll find time to watch some of the awesome vocal feminization videos on YouTube.
Intensifying The Sissification Process With Orgasm Denial
If you really desire to stay in the ‘sissy fast lane’ you will want to start limiting your male masturbation/orgasm habit. After a male orgasm, your sissy desires will typically wane… and that’s not a good thing, not if you aspire to be a serious sissy.
One way to proceed with this process is to start limiting your orgasms to once per week, and then allow yourself to cum only like a real girl. It’s called nubbing. Here’s how you do it:
Put on a pair of panties and tuck your limp sissy clitty down between your legs. I always buy panties where the crotch lining is open at the top, forming a pouch of sorts. I can then tuck my sissy clit down inside that pouch. It’s a tight fit, which is what you want. Then put on a bra and insert your breast forms. Finally, slip into a pair of sexy heels and lie down on your back.
Now that you’re properly prepped, began to lightly rub/nub the head of your panty encased clitty with one manicured finger—either the index or middle—only. This will take awhile, anywhere from 15 to 30 minutes, but eventually you will experience an extremely satisfying orgasm… kind of like a real girl would have.
It will build slowly, culminating in a very intense, long lasting climax. Your sissy juice will be deposited inside the pouch of the panties. Your sissy clit will most likely stiffen up a bit during the nubbing, but eventually you will train it to stay limp all the way to the end (aka limp clitty training).
By becoming a sissy, you are voluntarily forfeiting your right to manly ways of orgasm. Consequently, this will be your default way to achieve orgasm; cumming just like a girl does. No more fucking girls. Sissies don’t fuck… they get fucked! No more jerking off. That’s NOT what sissies do!
This is how you will cum from now on… once per week at the very most. Over time, extend the interval to two weeks, then three and finally, stay chaste for an entire month.
If you’re weak, a chastity device—coupled with a dominate keyholder—will ensure that you don’t cheat. You want to maintain a constant state of low-level horniness which is the normal and preferred psychological place that you, as a sissy, should become extremely comfortable with. Having sex on your mind 24/7 will only enhance your sissy experience. Being denied for a month will also properly prepare you for the next step in the sissification process.
Sissygasms — Learning To Cum Like a Lady
All sissies should aspire to reach this advanced level of sissification, which is training/programming yourself to cum by stimulation of the prostate gland only. What this means is that you will be moving past the point of needing any direct stimulation of your sissy clitty to cum… ever again!
This is gonna take some time princess, so be patient with yourself. To achieve this lady-like level of femininity, you will need a dildo or a prostate massager. I have a Nexus Revo—like the one pictured below—but it is a bit pricey. To get a good idea of the various prostate stimulators that are available, you might wanna read this article about prostate massagers.
Although I have yet to cum this way, I’ve heard that prostate orgasms are of the toe-curling/pure-ecstasy variety. Sissies that have experienced these girly-girly-cums say they would never go back to their manly ways of getting off, as those types of O’s pale in comparison.
The ultimate sissy orgasmic experience might be to cum this way with a man inside of you, if that happens to be your thing.
If you would like to read more about how to delicously cum like a girl, then you might be interested in my article, A Guide to the Elusive Sissygasm.
As you’ve figured out by now, there’s quite a lot involved in becoming a sissy. Each area can make for an intensive study on its very own. Becoming sissified requires patiently following a sometimes scary—but always adventurous—path.
Are You Ready For Some Serious Sissy Training?
Sissies have spent years being conditioned by society to play a male role. A feminine transformation requires serious sissy training which involes intensive feminine reprogramming. If you’re ready to be properly trained and sissified, then check out The Complete Sissy Training Guide.