For those of us who are crossdressers, and specifically male-to-female crossdressers, we’re faced with not only a lot of choices, but also a lot of challenges every time we want to express our femininity.

How long do I have to dress? Should I fully shave all the hair off my body? What will my wife/girlfriend/children/boss/family/neighbors say if they find out? Where can I store my female clothing? How much money should I spend on everything I need to transform myself into the woman I want to be? Do I really need the breast forms, hip pads, shapewear, makeup, nail polish, lingerie, dresses, high heels and wigs or do I just want them? Should I go out in public?

And on and on and on…

On top of that, there are also the unspoken fears we carry with us whenever we dress as a woman, and especially if we go out in public. Will I be read? Will I be seen as a man in a dress? Will I be threatened or harmed?

Those are only some of the questions we ask ourselves.

Then there are the bigger questions we ask. Why am I this way? Why do I have this need to dress like a woman? Why aren’t I normal? Should I tell my wife? Will my marriage survive?

These questions and fears are coupled with the overriding desire we constantly feel to express our inner woman and the continuing desire, no, the actual need we have to be dressed, seen, treated, and accepted as women.

As such, crossdressing presents us with an ongoing conundrum.

That conundrum exists because there are so many diametrically opposed opposites about being a crossdresser.

From the very first time we ever crossdressed, regardless of when we began, we know that we’re doing something that’s not considered “socially acceptable.” We know that this behavior isn’t considered to be the norm, so we must hide it. It’s not something we can openly share with friends and family. It’s “wrong,” “strange,” “not normal,” “different.”

So from the very beginning, we learn to hide part of ourselves and our lives. We learn that we can’t share this with anyone. We learn that this is going to have to be kept secret.

In many ways, crossdressing causes us to become two different people.

But intuitively, we already knew that.

We’re two people in one body. A man and a woman. Male and female. A masculine and feminine spirt.

And because of that dual nature, we have to express both parts of our personality, it’s not an option to not do so. Whether it makes sense to anyone else or not, it’s part of who we are, so we have to be able to express our inner woman. And truthfully, we want to be able to share her with the world, but we often can’t.

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Again, a conundrum.

As women we can be creative and stylish and show that by how femininely we dress. We can also be more open with our emotions and feelings. But as men we don’t feel those same freedoms. It’s actually almost the opposite, because, just like when we were little boys, men are supposed to be strong and not show feelings and emotions. So often we go out of our way to show how masculine we are and that we’re “real men” when we’re not dressed as our feminine selves.

A conundrum.

We’re concerned that we’re taking our crossdressing too far because we spend too much money on lingerie, dresses, shoes, makeup, and more, and when we’re not dressed that’s all we seem to think about. We’re constantly trying to become better versions of our feminine self by practicing our feminine mannerisms, how we walk, how we talk, how we act, so that we’re seen as real women. But we don’t try to improve our male selves to the same degree that we do our female selves.

A continuing conundrum.

We’re confused by the thoughts we have and the desires we feel to dress as women, but those thoughts and desires often seem to come in phases and leave just as quickly as they come. Even worse, at times we decide we’re going to purge and get rid of everything we own that is feminine. And then, once those feelings have passed, the old feelings return and we go out and buy everything back yet again, spending even more money to be able to transform ourselves into women.

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A conundrum that never seems to end…

I’m a man, but I want to look like a woman.

I’m the husband, but I want to be the wife.

And when we say and feel these things, at times it seems that none of them make sense!


It’s a conundrum.

And they keep on affecting us and driving our behaviors and actions, and especially our thoughts, every day.

I’m not a woman, but every time I look at a woman I wonder where she bought her outfit and how I would look in it.

I’m not gay, but when I’m dressed as a woman I have all these feelings about men that I don’t know or understand.

I know I should be discreet about this part of my life, yet I want to go out in public as a woman, to be seen and treated and accepted as a woman.

I’m married, but I want to live more of my life as a woman, even while staying married to my wife.

My wife isn’t gay, but I often wish she was so that she’d be more accepting of me as a woman.

As a crossdresser, these are the types of thoughts that often run through my mind. As I’ve spoken with other women like me, they’ve told me they have the same types of thoughts too. These very conflicting aspects of our personalities, these conundrums, persist in every aspect of our lives as crossdressers, whether we’re dressed as women or not.

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And even when we’re in our male roles, some aspects of our feminine desires always seem to come through. Whether it’s something as simple as wearing a pair of panties under our male clothes, shaving our legs and wearing pantyhose at work, painting our toenails, wearing a light application of mascara, or something similar, these are reminders of our crossdressing that we actively include in our daily male lives, as they help remind us of who and what we’d really rather be.

But truthfully, all of these thoughts, questions, feelings, fears and more are also the contradictions about what it means to be a man in today’s world. They’re constantly in our thoughts, as honestly, even we don’t know who or what we are.

And for many of us, especially those who grew up in an earlier generation, before the Internet, personal computers, cell phones, and social media, and before it was so easy to find and connect with others who have similar desires, it was even more confusing then.

Growing up as little boys back then, we were told that “boys don’t cry,” “boys have to be tough,” “boys don’t play with dolls,” and “boys don’t play with girls.” But we knew that was wrong, because we wanted to wear girl’s clothes, we did want to play with dolls and play with the other girls. And even worse, we wanted to try on makeup and paint our nails and wear jewelry. But we weren’t girls, so we couldn’t do those things.

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Instead, we adopted all the outward trappings of boyhood, even while at the same time we wanted to experience the same things we saw the girls going through – learning how to shave our legs, wear a training bra, how to coordinate colors and outfits, how to put on makeup and do our nails, and how to walk in high heels. We wanted to know how it felt to be a girl and to wear pretty clothes. To feel our bodies grow and change as our breasts start to bud and our hips widen, and all the other things that girls begin to experience as they grow into womanhood.

We wanted to be girls. Or at least to experience what they were experiencing.

But that couldn’t be. Wouldn’t be. We were boys, and boys didn’t do those things.

But not knowing “what was wrong with us” or why we “felt that way” made us even more confused. We didn’t understand what made us this way, what made us different, what made us have those types of feelings and desires.

All we really knew then is that when we were able to dress as a girl (and as women as we got older), it just felt right. It provided a sense of comfort, of completeness, of being the person we were really supposed to be.

But we’re males, why would we feel like that?

Again, it’s a conundrum.

So here’s how I sum things up.

Being a crossdresser is a conundrum. It always has been and always will be. We don’t know why we’re this way. We don’t know if something happened in the womb to make us this way or if we’ll ever know.

Realistically, we probably won’t.

So instead, don’t try to analyze it or understand it. Just accept it. Enjoy it. It’s part of who you are, so be glad you have the gift of femininity and that you can experience part of your life as a woman.

After all, we have something most other men don’t, and they’ll never even know what they’re missing – the joy of being a woman.

It’s a conundrum, but we love it!


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Janice Goode
2 months ago

This was such a relatable read! Thank you for putting into words that sense of an ever present duality we often carry. It really is a conundrum!

Karensa Peacher
1 month ago

Holly, this reads like my life story at different times and phases. Glad I reached my happy place with this conundrum, where I can enjoy the girl and still be a family guy. Great article!

Rachel Moore
1 month ago

Wow! You are so very right on the way I feel and have felt like as I tried on my first pair of panties, pantyhose. So much feelings of how good it feels how I felt. Is there something wrong with me. When I am in the really want to be a woman sense of mind how does a woman really feel. Her senses intensity how her breast and nipples feel. I have wondered about those feelings what would it be like to be with a man? I enjoy being with a woman dressed up. Does this mean Iam bisexual,… Read more »

Monique LaFemme
26 days ago

Very well stated. You captured my feelings exactly.

Danielle Anaya
14 days ago

Holly, you’ve been reading my mail. Thanks for the article. So many valid points.

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