I Want to be a Crossdresser

I get emails through my website that are very brief without a lot of information. I respond to almost every message but if the message is crude or if their email address is obviously not real, I don’t.

Many emails tell me they want to book a makeover and ask how much I charge. I don’t offer any services so I am always confused why so many people think I do.

Another common email topic is along the lines of “I want to be a girl” and “I want to crossdress full-time”.

Okay, then do it?? lol What’s stopping you?

I mean, I am not a total bitch, I know that there are probably millions of reasons why someone can’t (or won’t) wear what they want. I never really know how to respond to these questions. Maybe it’s because I like specifics? If my boss tells me to, oh I don’t know, “handle a situation” then I will handle it the way I think it needs to be done. I am capable and experienced and many situations require patience and time to get resolved, but his perspective of handling a situation is making the problem go away as fast as possible.

Rarely do we approach a situation in the same way. And rarely do I handle a situation the way he wants me to handle it. If he wants something done HIS way, then he should do it.

Or he should tell me exactly what he wants done instead of being vague. “Handling a situation” is open to a LOT of interpretation.

So when someone says they want to crossdress I think “well, go buy panties and get started”.

If you break down something to its very essence then it becomes, well, maybe not easy, but you have a very clear first step. The first step becomes obvious. Of course, taking the first step is another thing altogether.

When someone tells me they want to be a girl, my answer is usually not helpful at all. I encourage them to talk with their doctor and to find a therapist that is experienced with gender to guide them through this. Transitioning is a major life choice and working with professionals to determine that this is the right decision is crucial.

Maybe I am being too literal when I read statements like that, though. Maybe they just want to be a girl for a day, or in the privacy of their home or hotel room? I don’t know. This is where being specific is helpful to me but also for them.

Crossdressing is also open to a lot of interpretation. Many of us have a different idea what a lot of the terminology in our community means. For some, crossdressing is wearing lingerie under their male clothes. To others it’s wig, makeup, heels, breast forms, and a dress.

Either of these extremes takes a different path. Obviously buying a pair of panties is easier. I mean, you can buy anything online in relative privacy. So if that’s what crossdressing means to you, then there’s nothing from stopping you.

The key statement in that paragraph is that there is nothing stopping you. That’s not the same thing as not having any challenges or any risk. If you live with someone where they could discover your panties (or anything else) then this aspect of yourself will be revealed. This revelation might be the worst thing ever or could lead to having conversations that could have happened years ago.

Listen, I know we’re all terrified to some degree of someone learning about who we are and that many of us can predict how someone specific in our lives will likely react, but really, you never know. Maybe I am being overly optimistic at the moment but it’s possible there are people in your life that will love you and accept you. It’s happened to me.

However, when I say there is nothing stopping you I am neglecting the reality that YOU are stopping yourself. You are in your own way. Your own finger may be hovering and twitching over the “purchase” button. Why? Oh for many reasons.

One reason is the aforementioned risk of someone learning about this new addition to your wardrobe. Sure, you may hide your new panties in the back of your dresser or in a box that has a key and that box is inside another box and is covered in other boxes hidden in the back corner of your crawl space and they key itself is taped under the inside of a drawer, but if you’ve ever hidden panties from the rest of the world you may be able to relate to the paranoia and fear that someone, SOMEHOW, will happen to find that key and that locked box.

The Telltale Panty, if you will.

Maybe I am being too literal, but I really don’t know what someone means when they say “I want to be a full-time crossdresser”. Crossdressing is… well, it’s who someone IS. Someone isn’t a crossdresser only when they crossdress. You can be completely naked and still be a crossdresser.

Perhaps a full-time crossdresser is someone who is ALWAYS crossdressing. I mean, I guess? I suppose I am always crossdressing (if the definition of a crossdresser is someone who was assigned male at birth but wears clothes that are traditionally worn by girls). I mean, I am crossdressing RIGHT NOW. I am wearing a cute, lacey nightie as I drink my morning coffee. In a little bit I’ll pick out my panties and present as male for the rest of the day.

Of course, someone may define crossdressing as a complete femme presentation. Makeup, wigs, an outfit, heels… If so, then a full-time crossdresser is someone who presents as femme all the time.

If so, then transitioning might be the right step for that person. Transitioning can mean a lot of different things, whether it’s someone legally changing their name, their gender, and/or taking estrogen. None of these steps are *required* to transition, of course. I think someone can be who they are just by… well, being who they are.

So, if that’s what someone means by being a full-time crossdresser, then I would still suggest they talk to their doctor and seek out a therapist who specializes in gender to guide them through this.

This is incredibly practical and overwhelming, but if someone really wants to live their life in an authentic way and that includes presenting as a gender that is different from the one they were assigned at birth, then getting support and help is pretty crucial.

Of course, this is a very serious step if someone is looking to, well, be FORCED to crossdress.

Forced crossdressing is so interesting to me. It’s not really being forced if you seek out someone to “make” you do it. I mean, no one FORCED me to wear a bra for the first time, I was more than happy to do it, lol. I still am.

For some, crossdressing is a fetish and part of the appeal is humiliation. Being punished by wearing a dress or lingerie is very exciting to some.

Which is inherently fine. I mean, you do you. There’s nothing wrong with having a kink as long as it is ethical, safe, and has the willing participation of anyone involved.

I don’t think it’s humiliating to present as femme, but there is a significant difference between wearing a pink, frilly, sissy dress and, well, normal clothes. The pink, frilly, sissy dress is usually meant to be humiliating, just as a latex catsuit with thigh-high boots is meant to be intimidating.

But I don’t think forced crossdressing is always meant to be arousing and/or humiliating. I think there are a lot of us out there who desperately want to be who they are… But they just can’t take that first step. However, if someone MAKES them do it, it becomes a little easier. It’s not about someone CHOOSING to wear a dress, rather that person may tell themselves that they have NO CHOICE and they HAVE to wear it.

That person can tell themselves that they didn’t WANT to crossdress but they were FORCED to. There’s a part of them that can cling to resisting it (even if they know that they were more than willing to get glammed up.

Forced crossdressing isn’t always under the orders of a dominant woman wearing a leather dress, though. Sometimes someone just wants someone to help them start. They want a gentle, supportive, helpful person to pick out outfits, to encourage them, and to help them feel safe and seen and valid.

And I get that. When I was younger I kept hoping that my girl friends (and girlfriends) would decide that I should get a makeover (even though they didn’t know about all of this). I mean, I have seen plenty of movies and the like when boys are “forced” to be one of the girls and it was usually shown as it being fun, as opposed to a cruel punishment.

I suppose that this is a topic for another time but crossdressing=punishment never appealed to me. I never thought there was anything wrong with who I was/am and I never thought it was something that needed to be “cured” or stopped. The idea of being disciplined by way of a dress felt cruel by way of the person who was deciding punishment. THEY felt that “a boy wearing a dress” was humiliating. I didn’t. I don’t.

That type of punishment reveals more about them than myself. THEY are the ones who think that this is humiliating. THEY are the ones that think it’s embarrassing to be a woman. THEY are the ones who think that femininity is degrading.

It’s interesting that for so many of us they feel that they can only… hm, ENTER this world by means of kink. It’s not surprising, though. When “a boy that wears girl clothes” is highlighted in a movie or a talk show, they are almost always portrayed as confused, quirky, or kinky. It didn’t take long for crossdressing to be entwined with a sexual fetish. This more or less shaped how society sees those like us. And to an extent, we ourselves started to believe it.

“Why am I like this? Why do I like to wear panties? Oh it must be because it’s a kink because that’s what I have always been taught”.

Representation is important, and oftentimes we are portrayed in an inaccurate way. If a character in a movie is a crossdresser, it wouldn’t be a surprise if the script was written by someone who didn’t really understand people like us. So, they went with the common tropes and stereotypes of “boys that wear girl clothes”. This is the easier path.

I wonder how shocking it was for some of us to realize that despite what we were told, THIS isn’t always a kink. THIS doesn’t HAVE to be.

Being who I am comes from accepting that people, including myself, are more complex than they seem. That not everyone fits into typical classifications. That we don’t HAVE to. Who I am comes from loving myself and being gentle to myself. It’s about not denying who I am.

I suppose my point here is that YES, wearing what you want (for any reason) is intimidating and frightening and a lot of other things, and YES, we are conditioned to think that in many instances the clothes that we want to wear are associated with kink.

BUT you don’t have to think of this like that. I mean, sure, for some this IS a kink and that’s fine, but it isn’t always the case. It’s not for me and it never was.

Choosing to be “forced to be a girl” is one direction you could go to wear what you want, but you don’t HAVE to pursue that option.

LET yourself be who you are. It’s scary, yes, but it’s empowering to take these small steps yourself. Small steps lead to bigger steps and over time you will get to where you want. This progress, taken on yourself, will help you not only with the practical aspect of all this, but the mental and emotional part as well.

Yes, we may need help with choosing a size that will fit us (that’s the practical part) but gaining the confidence to go to the department store (or a website) and going shopping for yourself requires the mental part that is crucial to getting to where you want.

So, no, I can’t MAKE you do this (for various reasons) but if anything I hope my writings helps someone overcome the mental and emotional barriers that block the door to a beautiful world of femininity and embracing who you are. It’s up to you to open it.

Love, Hannah