Crossdressing 101: Part 3

Hello class, please take your seats.


Please pass your essays on the history of lingerie from our last lesson forward and I will return them after I have a chance to grade them. And Ashley, if you have forgotten your homework yet again I will be calling your parents. Again.


Today's lesson is about how crossdressing is under the umbrella, if you will, of identifying as transgender. In my opinion crossdressing is a specific subset of the transgender community. Similar to how romantic comedies are a type of movie, or how ballet is a specific form of dance.


Not every trans girl identifies as a crossdresser, but I believe that every crossdresser is a part of the trans community. And yes, I specifically said trans girl because for the most part society doesn't really see a cis-gender girl wearing pants or a boy's hoodie as crossdressing, but a boy wearing a skirt or nail polish tends to blur the line of gender norms and is quickly slapped with the label of crossdressing, at the very least. I mean, considering how intolerant much of the world is when it comes to breaking gender norms, being called a crossdresser is almost a kindness given there are other, crueler words to describe a boy that likes to wear pretty things.


I like identifying as transgender. I feel it's more representative of who I am. If I wear to strip the words 'crossdress' and 'transgender' down to the barest essentials, I would say, for me at any rate, crossdressing is about clothes, transgender is about identity. I also like and am comforted by being a part of a larger community, a community that understands and embraces that not one's genitalia should not determine my pronouns or wardrobe.


I started to identify as transgender once I started to explore the world of nail polish, makeup, wigs, and clothes (beyond lingerie). As time progressed I felt that who I am and how I wanted to look (occasionally) was more than just about wearing clothes. I have a very male name, and it seemed... uncomfortable to think of myself as that name when I was wearing a wig and a dress and winged eyeliner. Just as my boy name didn't seem quite right when I was dressed to the nines, I felt that thinking of myself as a boy wasn't right either. Slowly I started to think of myself as transgender and all of *this* was more about identity than clothes. I became comfortable identifying as transgender when a friend told me that the term encompasses anything that is outside the societal gender norms. It's a blanket term, so to speak. And it is a fabulous blanket. If this is the definition we're going with, then transgender can include a boy wearing panties to a drag queen to when I am en femme. I like this perspective.


Of course, I still identify as a crossdresser. Sometimes. Another subset (if you will) of the transgender rainbow is identifying as bi-gender. Essentially this is the term I feel most accurately describes who I am. When I am out in the real world, I am presenting in either boy more or en femme. I am either. I am both a boy and a girl, just not at the same time, if you follow me. I feel comfortable presenting as either of my genders. I like my boy life, I like my life en femme. I am never uncomfortable when I am in a boy mode, I don't feel I was assigned the wrong gender when I was born. I don't feel I have the wrong body. I absolutely understand some of us feel that way, but that's not my experience. But I still crossdress. Most of the time outside of my living room I am presenting as a boy. But under my boy clothes I am wearing panties. When I go to bed I wear a nightgown. I feel that crossdressing is when a boy wears something, anything, that most of the world thinks is "for girls".


But when I go beyond panties and have my thigh pads, my breast forms, stockings, stilettos, a dress, wig, and makeup... well, in the mirror I don't see a boy wearing "girl clothes". I see a girl. Of course, I still get hit pretty hard with dysphoria from time to time and still see a boy wearing a dress, but that is more about my self-esteem (or my less than perfect makeup) than anything else.


For the most part going from underdressing to being 100,000% en femme is more about identity and being comfortable with my gender presentation than it is simply or "only" about clothes. But goodness I have cute clothes.


Not only can identifying as transgender can cover a lot of territory there are also different... ah, categories of identifying as trans. And it sounds overly technical to describe who we are in this way, but perhaps a better simile is we're all musicians and some of us play jazz and some play pop music. Today's lesson is discussing some of the different ways to identify as transgender and why it's okay to be transgender.


And that sounds kind of silly, doesn't it? Of course it's okay to be transgender! Just as it's okay to be a crossdresser or like mystery novels or whatever you fancy. My point is that some crossdressers are wary of identifying as transgender. There seems to be an overwhelming perspective that being transgender means surgery or hormones or living full time. Sure, for some of us those are steps that are taken that feel right for themselves, but again I am going to refer to my own (and I stress this is my own but feel free to use it just as I adopted this perspective from a friend) definition and preference for what transgender means and that the word covers anytime someone does something or wears something that is commonly associated with a gender that is not the one someone was assigned to at birth.


And being assigned a gender before we know who we are is like being assigned homework before we learn the lesson.


For some, the term transgender has some weight to it. It can feel political or controversial or...well, not fun. 'Crossdressing' feels more... playful, in a way. There's some hesitancy to identify in this way as it sounds more serious, or other people may have expectations (or fears) with what being trans means, or could lead to. This is not unlike crossdressing being overwhelmingly associated with sex or as a fetish. Some of us have partners that know or tolerate or support or embrace our crossdressing. But once we go from crossdresser to identifying as transgender, the questions of 'where is this going?' and 'what does this mean?' return. And the fears return. If people connect 'transgender' with estrogen or medical procedures than a wife might fear her husband wants to transition. And maybe they do, but maybe they don't. Even though I identify as trans more often than as a crossdresser, overall my life and what I am comfortable with hasn't changed. I like both of my genders, I don't feel uncomfortable in boy mode. I don't feel being en femme is my "true" gender.


As I mentioned previously, since I feel this way, I identify more specifically as bi-gender. And yes, bi-gender is under the trans umbrella. Those who are bi-gender are comfortable having two genders. And I know there are more than two genders, but bi-gender literally means two genders. Besides my wife, the world sees me as EITHER a boy OR a girl. My co-workers see a BOY, some of my friends see a GIRL, some of my other friends see a BOY. My mom sees me as a BOY (except for that time at the mall). It's one or the other. And I am happy as both. Sure, one is more fun and fabulous than the other, but it's also easier (for me anyway) being a boy.


Drag is under the trans umbrella. Sure, performance and exaggerating stereotypes are not uncommon in the drag world, but there's also an activist and a political angle to drag. Never forget that Stonewall started with a drag queen.


Some of the other terms under transgender include agender, genderqueer, and non-binary. It's not easy to agree on definitions for many terms under the transgender umbrella, but let's do our best. I'll be the first to admit I am not an expert or authority on these terms, so if you have some thoughts, perspectives, or a personal connection or experiences, please share with the rest of the class.


Agender, to me, means not identifying as any gender. Therefore one might not feel they have to conform or adapt or fit with any norms or expectations. Someone who is agender will usually have them/they pronouns. Please note these are not one's preferred pronouns, they ARE one's pronouns.


Non-binary, in my opinion, IS a gender. Of course, I am willing to admit I could be completely wrong. Sometimes I feel I am non-binary especially when I am in boy mode but wearing a femme t-shirt and cute leggings. Someone who is non-binary has some commonalities with someone who is agender as they may feel that nothing is off-limits (so to speak) when it comes to what they wear.


Genderqueer is throwing all "rules" out the window. It's the very embodiment of understanding that clothes are just clothes and there's no such thing (or there shouldn't be) as "boy" or "girl" things, whether it is a beard or lipstick. A genderqueer person might wear a shirt and tie and stilettos. A goatee and eyeshadow. It's an absolute blurring of clothes and presentation and gender norms.


There are some similarities between these terms. A crossdresser and someone who is non-binary absolutely has some common ground. There are also some differences. A crossdresser may be very very happy when they're wearing panties or a nightgown and may love the idea of wearing GIRL CLOTHES but a non-binary person may look at clothes, whether it is a bra or a necktie and just see clothes as... clothes.


Again, I will be the first to admit that I am not an authority and much of today's lesson is based on my own opinion and observations. Like yourselves, I am here to learn as well. Your homework for today is to post in the comments your thoughts on these terms and if you feel I am waaaaay off the mark or if these terms and perspectives do resonate with you.


And perfect timing! There's the bell, please gather things quickly so you have time to change for cheerleading practice.


Love, Hannah



  • skye

    Thank you so much for laying out these terms. It allows me to think about where I stand and figure out how to express my self in a way that I feel safe a supported. I have always wanted to express my self as a girl but love my self as a boy as well. I do not want to have to transition full time. The term bi-gender resonates with me and allows me to realize that I can express my femme style without giving up my life as a boy. Being part of the transgender community also makes me feel more supported and understood. Thanks again.


  • Nikki

    Really connecting with this. I’ve been aware of my latent feminine aspect my whole life, and have dabbled in expressing it from time to time, but was always terrified! Terrified to get caught, terrified about “what it means”, terrified about every part of it. In man-mode, I present as a typical male except for my long hair (and my pretty panties), do man things, have mostly male friends, am a dad. In woman-mode, I am free of all the expectations the attend to manhood, and I feel just as genuinely me as I do in Male-mode, but because I don’t know that part of me nearly as well, it’s really exciting but not necessarily in a sexual way (but in that way too) when I get to be en femme. I’m blessed with a wife who is actively supportive in my journey, not just tolerant of it and that’s liberating. BUT… I’m really hung up on what it all means. It’s not typical of me to get involved with labels, but in the case it seems to matter more, and I think it’s because of all the shame that society has attached to crossdressing. Placing it on the trans spectrum is helpful in providing some conceptual distance from that shame, while allowing us to belong to something, rather than being in a state of exclusion from cisgender heteronormative gender roles. I may be bi-gender, I don’t know yet; but, I’m done repressing my feminine expression. Thank you for this thoughtful series of posts.

  • Shon

    Thank you for the wonderful lecture. I’m still wrapping my head around all these terms and myself. Am I bi-gender, transgender, gender fluid, or non-binary? I’m almost 40 and only now realizing that I have no idea what I’ve been denying inside myself. I’m trying but it’s frightening and confusing as hell. It would be so much safer to just go back into hiding. But for now, while I have the courage, I will continue to play with my wardrobe and process my feelings. Hopefully I can figure myself out. Reading things like this helps.

Leave a comment

Please note, comments must be approved before they are published

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.