I am a sissy. I am completely comfortable with this label. There was a time in my life when I self-identified as a transgender woman. I was never truly 100% comfortable with this label. It felt too much like a lie I was telling myself. I have never regarded myself as gay or even bisexual. This is not an essay about gender identity or sexual preference. To me, the defining uniqueness of the label sissy is that it is entirely a matter of choice. By this,I mean it is not about one’s gender identity nor about their sexual orientation and/or preferences.
To a great extent, the journey I outline below is about my personal journey. However, I feel that while not all who self-identify as a sissy will have taken the same journey as me, I am reasonably confident that most will relate to the common and shared aspects of their trip with mine.
Stage One: External Preconditions
Each one of us is born into this world with unique DNA. Our DNA will shape our physical appearance, our mental well-being, and our intellectual capabilities. How we see, hear, feel, taste, and smell the world is different for every individual. One could say that for each of us our DNA gives us some advantages in the game of life and some disadvantages. But it is not determinative of our fate in life. It is simply the hand we are dealt in life.
We are also all born into a uniquely different world. We are born in different parts of the world, different parts of a country, different parts of a city, different families, and different times — unique DNA. When it comes to our earliest childhood, no two humans will experience the same childhood. Experts on childhood development will tell you that who we become as adults is largely set in stone by who we are as children.
Every year, the world’s population grows by millions. Every year, thousands (or maybe millions) of sissies may be born. Or to be more accurate, thousands (or maybe millions) of children are born who have external preconditions that may put them on a path to the life of a sissy.
Stage Two: Social Interactions
We all live in a world of social interactions. As children, we interact with family members, neighbors, other children, classmates, and teachers. We interact with strangers and those who are close to us. We interact by avoiding some, embracing others, and ignoring most of the people around us.
There is a concept called the ‘Butterfly Effect’ that suggests that a butterfly flapping its wings in China could impact the weather in Texas. I will suggest that the same can be said of our social interactions. Regardless of how minor or insignificant a social interaction may be, it has a ‘butterfly effect on the rest of our lives.
I will suggest that anyone and everyone who is a sissy, who self-identifies as a sissy, came to be a sissy in no small part to the social interactions they had over the years.
Stage Three: Curiosity
While the world is changing, we still, for the most part, live in a world defined by the gender binary. Enlightened parents may choose to raise their newborns as gender neutral, but that does not mean these children are free of the power of the gender binary. For the most part, we all go through our childhood years as either boys or girls. Which is not to say that there is any clear definition of what is a ‘boy’ and what is a ‘girl’ that does not rely almost entirely on their genitalia, whether they are born male or female.

When one considers all the factors above, it is no wonder that some boys, some young males, become curious about what it would be to live life as a girl. I have heard it said that most young boys experiment at some time in their young lives with crossdressing. However, this is not about boys who experiment but rather about sissies. In terms of who they are, who they will become, their personal journey begins (as did mine) with curiosity.
Stage Four: Curiosity Leads To Answers
Curiosity is largely the first step to questions. Ideally, the questions we ask will provide us with answers. The boy who becomes curious as to what life could be like as a girl begins to get answers to his questions. These answers suggest to him that — for whatever reasons are important to him — life would be better as a girl. How did they come to this conclusion? I suggest that they came to this conclusion largely because they already knew what they wanted the answer to be.
Stage Five: Experimentation
Every individual on the planet is unique, so of course, every sissy on the planet is unique. How a sissy begins to explore life as a sissy puts every sissy in a room with hundreds of doors — and each sissy goes through the door that is right for them. They may begin by wearing panties under their boy jeans. Possibly, they are intrigued by the power of makeup and will begin learning how to use it to alter their look. Some may simply go to a store and wander through the girls’ wear department.
Stage Six: Positive Feedback

Whatever form of experimentation is chosen by our young sissy, they find it to be a positive experience. They like the way they look in panties. Something about their face with a bit of foundation appeals to them. While they are shopping, they find a dress to buy. Just the act of buying a dress feels good. They have asked the question. What would it be like to be a girl? Their observations of the world suggest life could be better as a girl. At some point, they go a step further and experiment with some aspect of being a girl. The result — all good.
Stage Seven: Resistance
The common trait of all sissy boys is that, bottom line, they know they are boys. Their curiosity about life as a girl is not about gender identity. (That is an entirely different conversation.) They know they are males. They know they are boys (men). They live in a gender binary world. Doubt, confusion, shame, guilt — all of these emotions and thoughts may impact their journey. For some, it will have a minimal impact. For others, it will mean possibly years of denial.

Stage Eight: A Closeted Life
Between the positive feedback and the resistance, the sissy must face a difficult choice. For many, this will mean living a closeted life. I would like to stress that, as I have said over and over again, every individual, every sissy, is unique. What do I mean by a closeted life? I am referring to that point in their life where they have gone beyond experimenting. They have a full wardrobe. They have learned how to use cosmetics. Maybe they even take the occasional late-night drive. Possibly, they have shared their secret with one or two friends. Most likely girls. However, they are still struggling with gender norms and have not yet gone public with their sissy self.
Stage Nine: Full Embrace

The key component of the full embrace of the sissy journey is that the sissy now accepts that he (or she should that be her preference, and probably will be) is a sissy. This is not to say they are living a 24/7 life as a sissy. It is not even to suggest that they have fully emerged from the closet. Life is often more complicated than that. What is does it mean that if they want to spend time as a sissy, they do so. They do so in both private and public settings. They do so with friends. They no longer feel their personal life must be within the acceptable boundaries of the gender norms of the gender binary.
Stage Ten: Let’s Get Sexual
I do not believe that any man becomes a sissy later in life. They may first become curious later in life and begin experimenting at that time. But, I think, that their sissy-ness is still a product of their childhood. Our questions, our curiosity, about life as a girl vs life as a boy are largely questions about gender roles — gender roles as we know them to be as children. We are curious about the clothes girls wear, their games, and their femininity. It is only later in life that we become aware of the sexual nature of being a woman.
Once we have worked ourselves through the first nine stages of becoming a sissy, once we have fully embraced life as a sissy, our feminine desires take us in different directions. Commonly, we want to spend more and more time enjoying the life we know as a sissy. It becomes increasingly important that we look our best, meaning in some cases that we attract the attention of men when we are out.
I have never felt myself to be gay. But I have had a lot of sex with men. But I have never had sex with a man when I was not presenting myself as a woman. I would never walk into a gay bar in male mode with the intent of hooking up with a man. This is not an essay about being gay or bisexual. It is about becoming a sissy.
I contend that the last stage of our shared and common journey is to get sexual with men.
This journey may say more about my sissy journey than about yours. I could have it all wrong — I am wrong a lot. Would love to hear how this journey mirrors your journey. Of how you took a different path.










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