We Mistresses at Sissy School often get the question of “How do I become a sissy?” .  Let’s take a look at some steps you can take to help get you started on your feminization journey.

Beginner’s Guide to Feminization

Feminization can take many different forms and there are as many nuances to feminization as there are guys who want to be feminized.  When you first begin your feminization journey, there are a few questions you should ask yourself.  First and foremost, is whether you want to be a sissy or a passable cross-dresser.

Do you Want to be a Sissy?

Those who want to be sissies realize they will never be a real man or a real woman so the best they can hope for is to be a good sissy gurl.  There are many different types of sissies and many different variations within each type.

Sexual Preference: If you’ve determined you want to be a sissy the next thing you need to look at is your sissy sexual preference.  Do you want to be a sissy cock sucker or do prefer to think of yourself as a sissy lesbian? Possibly, you don’t even associate being a sissy with sex.

Sissy Style: There are many, many different sissy styles to decide upon and really, you don’t have to settle for just one.  Are you a frilly sissy who likes twirly dresses, ruffled panties and ankle socks and patent-leather Mary Janes?  Maybe you are a slutty sissy who likes wearing short, tight, revealing clothes. Perhaps you prefer being a sissy maid and wearing a sexy/slutty French maid outfit.

Sissy Service: What type of “service” do you enjoy?  Servicing Mistress by cooking and cleaning, drawing her bath and helping her get dressed?  Perhaps you prefer servicing Mistress and her friends sexually.  Maybe you enjoy showering her with money and gifts as part of your service and to show your devotion.

To be Humiliated or Not to be Humiliated?: Do you enjoy being humiliated for the fact that you aren’t a real man and will never be a real woman so you must settle for being a sissy gurl?  Humiliated about how ridiculous you look in your sissy get-up?  Or do you prefer the subtle, implied humiliation as opposed to overt humiliation?

Companion Fetish(es): There are many companion fetishes that go along with being a sissy.  There are sissy cuckolds, sissy cock suckers, sissies who enjoy body worship, punishment and discipline, and so much more.  The best way to determine the things you enjoy doing as a sissy is to give them a try- even if only in fantasy.

If you enjoy feminization but aren’t into being a sissy, maybe you want to be as close to a real girl as you can be, with the hope of becoming a passable cross-dresser.

Do you Want to be a Passable Cross-dresser?

Typically, cross-dressers enjoy dressing and acting like a real woman with the goal of being passable, including having a feminine voice.  Just as with sissies, there are many different nuances to being a feminized cross-dresser.

Sexual Preference: Being a cross-dresser does not automatically mean you prefer sex with men when you are en femme.  Many cross-dressers prefer to be with women, even when en femme, and consider themselves lesbians.  Other cross-dressers consider themselves bi-sexual and enjoy being with both men and women, sexually.

Cross Dressing Style: Just as there are many sissy styles, there are many cross dressing styles. Do you enjoy the timeless, classic look or do you prefer a very sexy, slutty look?  Perhaps you like to be a little of both, depending on the circumstances.

Companion Fetishes: Cross dressing is rarely a standalone fetish.  There are usually components to other fetishes that go along with it. There are as many combinations as there are cross-dressers and fetishes. I encourage you to explore different things to see what you enjoy the most.  Don’t just rule something out because you don’t think you will like it.  You never know until you try!

The topic of feminization is a complex one that can’t be sorted out in just one blog post, though hopefully, this has given you a few things to consider as you get started on your feminization journey.

Until next time, pets~

Your Sissy Training Mistress

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