Crossdresser Turned Sissy

Take it from a crossdresser turned sissy, Being a sissy can be incredibly freeing. Slowly letting the last vestiges of your masculinity slip away and being replaced with sissy things that make you feel ultra-feminine like…

Panties, bras, nylons, heels, dresses, nails, makeup and so on.

Writing that last sentence made my sissy clitty twitch in my panties.

My ‘sissy style’ is focused around being a fashionably—and fabulously—dressed ultra-feminine but sophisticated sissy. Always wearing perfectly applied makeup and 5″ heels.

For me, being a sissy is all about the clothes. I enjoy going out in public and flaunting my femininity.

If you felt compelled to label me, I could probably be categorized as more of a classic crossdresser-turned-sissy rather than conforming to any sort of classic sissy style.

A classic sissy? You know… a girl dressed in a short A-Line dress with petticoats underneath and perfectly matching moderately-high heels—along with a bedroom decorated in frilly fashion.

You, on the other hand, probably have a different sissy style that suits you perfectly.

That’s the freedom that comes with being a sissy. You get to choose your very own sissy style—not beholden to any preconceived stereotype of what a sissy ‘should’ be or act like.

For instance, you might enjoy being the perfect sissy maid, prancing around in your latex maid’s outfit, serving to your heart’s delight.

Then again, being the perfect bimbo fuck-doll while being forced to submit to your dominant in any way He or She requires, is what does it for you.

Of course there are sissy babies (Little Girls) who get off on diapers, pacifiers and bottles

You might be drawn to be a sissy sex slave—cuffed, collared, chastised and hooded, led around on a leash. If you’re lucky, you might even receive a caning.

Many sissies enjoy the humiliation factor and nothing is more humiliating than being a cuckolded sissy, forced to fluff your Mistress’s boyfriend while locked in chastity.

As a crossdresser turned sissy, Personally, I find several of the above scenarios exquisitely erotic.

What I don’t get off on is wanting to be a cock-craving, cum-eating faggot.

That appears to be how the stereotypical sissy is portrayed by the majority of sissy porn.

And if that happens to be your sissy style, I’m all for it.

But here’s the whole point of this email.

Sissies are complicated creatures with many diverse desires, wants and needs. People will be trying to figure out what’s inside a sissy’s pretty little head until society collapses… never coming close to finding out.

What we—or should I say ‘I’—know about sissies amount to just three things:

  1. Sissies are intensely intrigued by all things feminine
  2. Sissies are submissive and subservient
  3. Sissies are not real men

We gotta have some common parameters that we can all agree upon, don’t we?

As a sissy, you ARE the above—or you’re simply not a sissy.

Beyond that, you’re free to express your sissiness in any way that resonates with you.

Know yourself sissy. Then be truer to yourself than a drug dealer at a Berlin rave club.

Affirming and then embracing your authentic sissy style will go a long way in empowering you to go further down the sissification rabbit hole.

Getting caught up in what type of sissy you think you ‘should’ be will only serve in holding you back.

After reflecting on your sissy style, you might now be wondering…

Are sissies typically gay?

Are sissies transgender?

Should sissies be in chastity?

I’m glad you asked because we’ll be answering those questions, and a few more, tomorrow.

Do us a favor and create an account at our sissy community

In the meantime—as far as chastity goes—you can read more about chastity devices in this informative article.