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Am I a Sissy or am I Transgender?

by Mistress Daphne of


“Am I a sissy or am I transgender?” This question is asked a lot and I hope to guide you to knowing one way or another. I have a great deal of experience in the sissy and transgender worlds and feel I have great information to help you make your decision.

That said, there are gradations and variables on the spectrum of male femininity and only you get to make the final choice of what you call yourself. I will help guide you, but keep in mind, it isn’t uncommon for a sissy to later find/feel they are really transgender… or the other way around.

It’s crucial for you to allow fluidity in the feminine part of yourself.


What Is a Sissy?


A sissy is a man who enjoys his feminine side in certain ways.

He might want to wear panties, usually pretty panties. He might prance around in them in front of the mirror. He probably masturbates while wearing the panties or wrapping them around his cock. He might love being called “girly,” or a girl when in the sissy space.

Sissies also tend to like wearing ultra-feminine clothes, almost exaggerations of what feminine can be.

There are sissy maids who enjoy dressing up as a maid with petticoats, stockings, and high heels. Throw on a maid’s cap and you have the whole picture.

Others might choose to be sissy girlie girls dressed all in pink with frills and bows. Petticoats again are common. Hair with ribbons and makeup very exaggerated, but still pink, not in a sultry way like a sissy slut would do.

Sissy sluts are yet another melodramatic choice for displaying that feminine part of yourself. Do you think of yourself in an extremely sexualized version when you are in that feminine mood? Do you think about seducing a man (or woman!) and having sex with him for hours and hours, smearing your slutty makeup and bright red lipstick? If so, I would put you in the sissy slut category.


What Does Being Transgender Mean?


Just as with a sissy, being transgender can be any number of things. Let’s look at them here.

Some people feel that, for them, being transgender means they feel like they are living in the wrong body. It’s important to know that not all transpeople feel this way, but it is a common feeling and belief.

Did you want a girl’s name when you were younger? Did you ask to be called by a girl’s name? Perhaps people laughed, but was it something you thought about?

Perhaps the clothes you were put in did not feel right, or correct. You felt like you should have been in dresses, not jeans and boy’s shirts. Were you discouraged from wearing “girly” clothes or wanting your hair long, maybe with a barrette in it?

Did you want to do “girly” things like play with Barbies or play dress-up with the other girls? Did people make fun of you if you did do those things? Did you still want to do them or sneak around doing them?

While it’s common for sissies to dress up in a girl’s or woman’s panties or dresses, for a transgender person, they feel “normal” when they dress in feminine attire.

These are external representations of what it can feel like when one might label themselves transgender, but there is internal aspect to address, too.

Transwomen are often shocked when they look into the mirror and see a man standing there. They should be looking at a woman. They find it odd to see a hairy chest instead of breasts. It can be a shock every single morning to see stubble in the mirror and have to shave yet again.


Variations On a Theme


It really is crucial to know and understand that these are generalizations many folks can relate to. These are not the be all and end all to definitions of either a sissy or a transwoman. Please continue searching for other definitions, by sissies and transpeople if possible.

Each of them can speak for themselves. I am speaking from a ciswoman’s knowledge of sissies and transwomen, which is extensive, but by definition, prejudiced and not comprehensive.


Most of all, BE YOURSELF! And be proud of who you are.


Are you asking yourself this question? Give one of our Feminization Mistresses a call, today!