Crossdressing 101: Part 2

Good morning class!  
For those who weren't here in the previous lesson my name is Ms. McKnight and I welcome you to Crossdressing 101.  In our last lesson we discussed the origins of the word 'crossdress' as well as how I came to learn who I am.  In today's lesson we are going to go a little deeper and discuss what exactly IS crossdressing and the stigma that the word can have.
Some of you are taking this class because you aren't sure how you identify.  Are you transgender?  Are you genderfluid?  Are you bi-gender?  Personal identity is very, well, personal and we are all on a journey to discover and create who we are and learn to embrace what we want and what we want to wear.  It's not uncommon for us to evolve and change how we identify.  What can make this even more challenging is finding a consistent definition of what each of these potential terms means.  I will be the first to admit that my definition of crossdressing is my own perspective and opinion.  I do not claim to be an authority on vocabulary and I understand that someone else will likely have a different thought on the terminology of all of this.
If we look at clothes and makeup and style as binary, meaning this is for BOYS and this is for GIRLS, then we have a place to start when it comes to definitions and parameters.  I would like to qualify what I am about to discuss is a VERY broad and basic observation.  A shirt is, well, it's just a shirt.  BUT!  If the shirt is pink, it becomes (generally speaking), a GIRLS shirt.   If a shirt has a baseball on it, then it's a BOYS shirt.  Of course, girls like baseball and you shouldn't let your genitalia determine what color you wear, but we (unfortunately) live in a binary world and many people feel the need to classify everything for a specific gender.  When we start going a little further and look at a dress, or high heels, or lipstick, then those objects, those pieces of fabric become GIRLS things.  Boys don't wear dresses or stilettos, so they are for GIRLS.  
When I was a young boy I learned very early that YES!  A boy COULD wear a dress.  The back zipper could be a little tricky but I could, and did, wear a dress.  In secret, of course.
My definition of crossdressing is when a boy wears something that is typically associated with girls.  This can cover things as small as nail polish or something as amazing as a wedding gown.  
Yes?  You have a question Brittany?
Oh, can a girl crossdress?  Yes, I suppose.  But I think when a girl wears boy clothes, such as her boyfriend's hoodie, it is looked at a little differently by most people.  A girl wearing her boyfriend's sweater is cute and a symbol of her love of him.  But a boy wearing his wife's nightgown when he misses her, well, it's not the same thing.  I mean, I think it is, but we are looking at what crossdressing is on the most basic and broadest of definitions.  

Wonderful question, Brittany.  And your lolita dress is absolutely adorable but you need to straighten your seamed stockings.
Is it fair that a girl can wear boy clothes but a boy can't wear girl clothes?  Well, I suppose not, but it's not their fault that the rest of the world doesn't get their panties in a twist when girls wear BOY things.  It's the world that needs to change their outdated and limited thinking when it comes to BOY clothes and GIRL clothes.
So, in summary, every single one of you in this class is, by my definition, crossdressing.  And yes, it is a VERY broad definition and there are more nuances when it comes to gender identity and gender presentation than this very general perspective, but it's a good place to start.  Obviously there are different "levels", so to speak, of crossdressing.  A boy with black nail polish might be considered metal or punk, but still, it's crossdressing.  Yes, even if the nail polish, or even or a dress, is designed and marketed towards boys.  The world in general doesn't care, or see the difference if the panties I am wearing are designed for someone with my anatomy, They are PANTIES and PANTIES are for GIRLS.  Pink and lace are for girls, boys wear gross boxers.  
Going back to the boy with black nail polish, yes, someone might raise an eyebrow when they see him, but compared to a boy wearing a skirt it's not that big of a deal.  It's still crossdressing but the more, well, obvious and noticeable the clothes or makeup is, the more people will point, gossip, and be outraged.  Again, it's not fair, but it is what it is.  
This leads into the next part of the lesson which is the stigma that is associated with crossdressing.  There is a stigma not only within the cisgender world but within the transgender community as well.  By and large (and yes, I know there are exceptions and this is a very broad perspective) looks at a boy crossdressing as BAD and PERVERTED and SEXUAL and KINKY.  This is not going to change.  In our last lesson I discussed how shocked I was to see how crossdressing was very commonly associated with fetishism and sex.  Sex and kink had nothing to do with me wearing lingerie or dresses.  To me, they were just clothes I wanted to wear, and there was nothing arousing about wearing what I wore.  It was then that I started to realize that most of the world thought of crossdressing as a fetish, as a kink, as a sexual thing.  
And anything along those lines can become taboo, it can become a stigman.
Before I continue, I want to make it clear that if indeed this side of you is your kink, if your PVC French Maid dress turns you on, then you go girl.   I am not kinkshaming anyone.  Promise.  But I want to make it very clear that crossdressing may be YOUR fetish, it is NOT a fetish.  
Ashley?  You have your hand up?

Yes, thank you, I can explain.  A fetish is, broadly speaking, an object that arouses someone.  It could be anything from 5 inch stilettos to a rubber catsuit to an elbow.  Yes, some people are aroused by elbows.  It doesn't mean that elbows are sexual, it's just how someone is wired.  
But we live in a world where the loudest people set the stage and control the narrative of everything.  No matter how many of us are out there that wear eyeliner or garter belts because it's what we love, the damage, if you will, has already been done.  I can't see this perspective changing on my lifetime, or in the next few decades.  And that is me being optimistic.  When I was growing up I was terrified of being "caught".  When I got older I was still afraid, but since I learned that crossdressing is viewed (predominantly) as a fetish, I was even more terrified.  The word at one point calmed me, reassured me, gave me something to identify with and as.  But once I learned that it was commonly associated with sex (nothing wrong with sex, of course), I didn't want to be "a crossdresser".  If crossdressing meant fetishism, then it wasn't who I was.  It wasn't the right word.
As time passed I learned to disregard the opinion and perspective of what crossdressing meant to most of the world.  I couldn't control what others thought, and I wasn't smart or ambitious enough to try to change this viewpoint.  It's kind of like the difference between country music and western music.  Yes, I am sure there are nuances and specifics as what distinguishes these genres from each other, but I don't care.  I was just going to keep wearing what I wanted, and explain as best I could to the people in my life that needed to know who I was and what I wore.
Social media and the internet have evolved (in some ways) compared to the online community of twenty five years ago.  Yes, Googling 'crossdress' still brings up mainly fetishy sites and images, but there is more non-sexual representation of crossdressing than when I was in college.  There is an overlap or at the very least, seats at the same table of identifying as transgender.  In our next lesson we will discuss in greater detail this relationship, so to speak.  These days I identify as transgender, or more specifically, as bi-gender.  But I started my gender journey by identifying as a crossdresser.  Even after learning how crossdressing was usually associated with fetishism, I still (sometimes reluctantly) identified as a crossdresser, I just would clarify that it wasn't a sex thing.  I don't think it's unfair to state that many transgender girls likely identified as a crossdresser at some point in their life.  A drag queen could have started their journey the same way I did by trying on their mom's high heels and something just clicking or awakening.
As the transgender term became more woven into our vocabualrly, I started to search for this term online when I wanted to find resources or others like me.  I found others like myself that wanted to, or did, wear what I wore but, like myself, didn't associate lingerie with getting aroused.  I started to identify as transgender as it felt more inclusive and, in a way, less stigmatized the world at large.  But I soon learned that even in the trans community crossdressing was still a stigma.  Many of you are here because you are wondering what the difference there is between identifying as a crossdressing and identifying as transgender.  We will be covering that in greater detail in our next lesson, but it is believed by some that there is a difference.  And to be fair, I think there is but I believe a crossdresser is absolutely a part of the transgender community.  
There are those in the transcommunity who will say that a crossdresser is "just a crossdresser".  I don't think this is a majority view, but that thinking is out there.  Firstly, no one is JUST anything.  Life is hard, and we all have our struggles and let's face it, this side of us doesn't make anything easier.  Some in the transcommunity don't feel that a crossdresser should consider themselves part of the T in the LGBTQ+ community, but I believe that anything that is outside the traditional gender roles and gender norms is absolutely under the transgender umbrella.  Our next lesson will expand on this in greater detail.
My point is that the dominant view is that crossdressing=fetish, or at the very least, crossdressing is only about girl clothes and not part of one's identity.  But really, anything someone does becomes part of their identity.  If you are some guy named Steve and you like to fish, then you are Steve the Fisherman.  I'm sure there is more to Steve than sitting in some silly boat, but there doesn't have to be.  
Oh, there's the bell.  Class, your homework tonight is to practice doing your winged eyeliner and applying false eyelashes.
Love, Hannah


  • Shawna

    I had to rejoin the class to check my question. It seems rude of me to leave the teacher with a question. Also how ill-mannered not to remark how wonderfully fabulous she looks on any given day! Also I'd like to thank her for providing context and a resource. I have thought about my question and must realize that the Beauty to be Enjoyed is found in the one who did the painting; the creator. So that would have to be the person I assume. It couldn't be the paint. The Paint was scraped from the Earth. So the Artist didn't create the paint. So is the Artist a Creator or just a hopeless mimic and manipulator? ..too Dreary Dearies! Hats off to the Artist who created my Beautiful Floral Navy Swing Dress that arrived at my door last week. I introduced them to my Queen Anne Flats and they got along swimmingly! I never wore the flats before (two boats) but some how they work with this dress. I am so glad that Dana commented also… for me its all about spoiling myself.. and the Dancing..!

  • Amyrakunejo

    'Steve the Fisherman', lolz (almost had a Primus reference there 'John the Fisherman')

    Me? I'm a feminine, but non-binary person. Enbyfemme. That has not changed, even if the environment of living has.

    So, I guess I fall under L, Q, mayhaps T? I dunno. To be honest, labels are beneath me, the person matters more, and if that sounds progressive and far more advanced then maybe it is, but really, it's just me; I was raised better, and I was not raised in a place where commercialism and religion ruled, but where no one had any power over another. Right, not gonna go deeply into that.

    A person that presents femininely is to me, feminine. It doesn't matter if they're having fun, making money, are living life, or any of all three.

  • Shawna

    Thank-you Hannah.. I'm a crossdresser.. I wanna be loud.. and I want control a narrative. Sounds like useful fun. I suppose that anything can be a fetish.. what I dis-like is the fetish for being annoying. They drive me crazy..! I think the idea of crossdressing crosses every mind as soon as they know that it could exist for them. The idea is either rejected or kept. I backed shelved the idea (as many may do) to possibly play upon later… it really never goes away. Now is Later. Seperations and the Covid mayhem isolated me. I refused to go to the barber. I started using the Internet more and more.. let my nails grow out.. started on-line shopping. Bought 18 pairs of women's shoes.. I went to En Femme Style and bought every dress that fancied me in 2 sizes each.. every acoutrement.. what fun! It was like Christmas all year long. I love En Femme Style.. when rude people say 'So you wear women's clothes.' I gotta a snappy answer: I say: Absolutely not! There all mens clothes!.. It's just my snappy answer to their annoying question. En Femme sell Clothes with no sizing guess-work for a person with a man's shape and who is used to buying men's sizes. Thats what I like. My question for the teacher is this: What is the point of all this..? It's got to be to enjoy beauty right? Then where is that beauty found? In the person? or in the Paint? ,,Bye..!

  • Dana

    These are some terrific takes. I've often wondered about women wearing men's clothing without really any negativity from society. My wife likes to wear some of my sports jerseys on occasion, and shirts when working around the house. I never really gave it a thought, especially since most of my male "wardrobe" consists of more utilitarian wear like tee shirts and long sleeve work and flannel shirts. I don't think I do this as a fetish. In fact, it seems when I dress, it is almost like some polar opposite time for me. As I said, my man self is very plain, blue jeans, tees and sneakers, could really give a hoot what I look like. When I get to be Dana, I go for the boots, jeggings, panties, the pink shirts, etc, and I try to be as meticulous about my look as I can. I don't really get turned on, per se' by Dana, more like "My God, is that really me!?!?" and enjoy the transformation, and time I get to do it. It is sad that cross dressing has been the "comic relief" for as long as I can remember. I remember my folks watching Milton Berle dressing up and the people laughing hysterically. One movie that always comes to mind for me is "Mrs. Doubtfire". I watched it, being told how hilarious Robin Williams looked dressed as an older woman. I found very little humor in it, mainly because he was forced to do it just to see his kids. In the end, however, his Doubtfire character made him a better man. I also feel Dana has made me a better man. I have no desire to come out of the closet, mainly, my wife would be hurt and never accept it. But, I will never stop dressing.

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