Crossdressing 101: Part 1

Hello class, my name is Ms. McKnight and I would like to welcome you to Crossdressing 101!

You are all looking so cute in your plaid schoolgirl skirts and white stockings! And your whole look is completed by shiny black patent Maryjanes. Absolutely adorable.

We are all here today to learn about crossdressing. What is crossdressing? Where does it mean to crossdress? I can't promise to provide you with all of the answers but I will do my best.

Crossdressing, in my opinion, is simply wearing...something, anything, that is typically associated with another gender. This is an overly simplified definition but it's a good place to start.

Yes, Jessica? You have your hand up? And cute pink nail polish, by the way.

Wonderful question. The word's origins are German and is a translation of the Latin word 'transvestit'. 'Trans' means 'across', such as a transatlantic flight or crossing the ocean. 'Vestire' means clothes, such as 'vestments'. Combine the two words and you have 'transvestite', or crossdress. Personally I think 'transvestite' is a little outdated and I wish the word would go away. No offense, Latin.

But yes, a boy wearing nail polish, a boy wearing panties, a dress, lingerie, eyeliner, that is all crossdressing. Unfortunately EVERYTHING is genderized, especially clothes. Colors, styles... everything is 'for boys' or 'for girls'. I hate it, but I also love it. I love wearing 'girl clothes'. Panties are sooo much for fun than boy underwear, femme jeans are more fun that boy jeans. Regardless, my point still stands, if you are wearing anything that is typically associated with something girls wear, then you are crossdressing.

The first time I heard the word 'crossdresser' was when I was around twelve years old. I can remember exactly who said this word to me, and where I was. I don't have the best memory in the word but this was one of the most significant moments of my life. I learned there was a word for people like myself. I was a crossdresser. I never thought I was the only boy who liked to wear panties and dresses, but I had never thought that there were so many of us that there was a word for boys like myself. It was, to be honest, completely reassuring. The idea that there was a word for me made me think that perhaps who I was wasn't so strange. I wasn't so alone. I was scared to death of being caught when I was younger (and being caught now) as I wasn't sure of how to explain why I wore what I wore or why the mannequins modeling beautiful lingerie at the department store made me jealous. I couldn't put who I was into words, but all of a sudden there was a label (if you will) that could hopefully explain who I was. I was a CROSSDRESSER. Why did I sneak into my sister's closet to try on dresses? Because I was a crossdresser. Why did I want to wear pink panties? Because I was a crossdresser.

This revelation cheered me for years. I didn't think of it like this at the time, but I was part of a community. There were others like me. I always felt a little... lonely I guess. I remember being very young and trying on my mom's heels. Wanting to wear lipstick. Wanting to wear cute undies. I was five when I wanted to wear the princess gown that the dress-up box had in my kindergarten class. But despite how strong these desires were, I knew I couldn't. I knew I shouldn't. When we are young we are taught that boys and girls do, like, and wear specific things. Some of it was ingrained in us by society or our parents, some of these gender norms were created by kids themselves. It was silly then and it's silly now but there was a wall in my first grade class that only girls were allowed to touch and another that was for boys. Isn't that silly? Isn't that stupid? But it's not much different than certain clothes, styles, and colors being for a specific gender. I didn't think what I was doing was 'wrong', but I knew it should be kept a secret. Being found out would have branded me as a sissy for life. I would forever be that boy that wore a dress when I was in grade school.

Although I knew I couldn't be the only boy in the world like me, I never thought I would ever know anyone else like myself. It's not like this topic would ever come up. Sure, people ask each other about their favorite bands or what kind of food they like, but could you imagine someone just saying "you know I REALLY love wearing lingerie, have you ever worn a bra? What style of panties do you prefer?" The opportunity to connect with others like myself happened on my first day in college. I sound soooooooooooo ancient when I say this, but the internet was a very new thing when I was a teenager. The school's library had a few computers connected to a dial-up modem (see? I am ancient.) and the very first thing I searched was the word 'crossdresser'. And it was at this moment my world changed again.

I didn't know what I expected to find with this search but I certainly wasn't expecting to find nothing but stories and pictures of men wearing panties and... well, pleasuring themselves, or being intimate with other men wearing lingerie. Scrolling through images and writings and personal ads gave me the impression that a crossdresser was, well, a crossdresser was a fetishist. I was stunned. And a little heartbroken. For years I identified in secret with a word that describes who I was, that explained who I was. But I was not this. There was nothing about lingerie that.. ah, aroused me. I had no desire to hook up with other men. Simply put, there was nothing sexual about my dressing. What dismayed me even further was reading articles that the search provided about crossdressers. Some were newspaper articles, some were tabloid stories, some were "in-depth looks at the world of crossdressing". Almost every single one portrayed crossdressers as fetishists, as perverts, as deviants. I was crushed. I was not these things. Wearing panties, lingerie, was a beautiful part of my life. It brought me peace and happiness. There was nothing "dirty" about who I was, or what I did or wore.

That day was as significant as the day I learned the word crossdresser but in a different way. When I was younger I learned of a word that I thought explained who I was, but on this day I thought that maybe this wasn't the word for who I was, or am. But if I wasn't a crossdresser, then what was I? Who am I? I began to see how people like myself were portrayed in movies and television shows. A boy wearing a dress was played for laughs, portrayed as perverts, and an easy joke. These portrayals not only reinforced the idea that a crossdresser was a pervert to me, but also to everyone else.

I think most of us have tried to stop doing what we do. I have purged so many times it's not even funny. It breaks my heart when I think of this sexy PVC gown that I threw away when I was younger. However as I grew older I knew I had no control over who I was. It wasn't a phase that I would outgrow, this was who I was, even if the word 'crossdresser' wasn't exactly the right fit. When I was in my twenties I was dating a girl that I thought I would end up being with for the rest of my life. But isn't that how all love is when we are that age? I had made the decision to tell her who I was, what I wore, and wanted to wear. I did this for two reasons. One reason was selfish. I had hoped that she would have been accepting and would be okay with me wearing panties. The other reason, and this was a lot less altruistic, was that I felt that she HAD to know. She needed to know who I was. It wasn't going away, I would do my best to NOT dress, but I would always want to.

Long story short, I told her, she put this revelation in the only frame of context she could courtesy of how someone like me was presented in the media, and said I was a crossdresser. The stigma lived on.

I mean, yes, I guess so.

But that word was limiting. It wasn't exactly who I was but it was the only word for someone like myself.

I think this word will be synonymous with sex and fetishes for a very long time. In our next lesson we will discuss the transgender community's relationship with those who identify as crossdressers. Your homework tonight is to pick out a new pair of panties and a nightgown to dream sweet dreams in.

Love, Hannah


  • Rc

    I am so glad I managed to stumble into class. I too am older than the author and remember when we didn’t have any computers and phone were hung on the wall WITH CORDS! I remember trying on my mom’s panties and just feeling so right. But, like so many others I quickly learned how deviant I was and to keep it a secret lest I be labeled and ridiculed. I lived my life like this. Hiding who I was, I got married, had kids, and still I hid all of this. I don’t regret my life at all, but I it has always been incomplete. Recent events have caused me to come out to my wife. To my disbelief she said she had always suspected and was relieved and excited that I had finally told her. She found this website and we have been shopping together. But reading this “class” hits home. It almost brought tears to my eyes because I finally have found others like me! Thank you for doing that for me. Now I need to look some more to find more resources and others that like are like us. This is not a kink for me, I just feel complete when I dress. Thank you, thank you, thank you!

  • Satin

    Oh how I loved to wear satin string bikini panties and satin garter belt with silk thighs and a satin mini skirt over it all. Are used to fantasize how it would feel to feel a hand rubbing my satin miniskirt over my satin panties

  • Ellie

    That really resonated. I grew up thinking I was the only one out there. You have found a partner. I haven’t. Once upon a time there wasn’t internetz connecting all us freaks together.

  • Sina

    I am older than the writer, I was all grown up when the internet arrived. Like Hannah I have had many collections that went in the garbage or to charity boxes. I am once again collecting and I feel a strong need to dress up, hair, make up, nails and jewelry. I’m talking to an online counsellor and working on my poise, fitness and care. I don’t want to be ashamed anymore. Crossdressing gives me a wonderful feeling and if it’s just beautiful and fun.

  • Amyrakunejo

    I'd be the one in the back wearing red heels, black sheer stockings, a red pleated skirt, and a black off-shoulder blouse, Goth-Glam makeup and Metal in my ears, lolz

    Oh yes, the internet's infancy, it was short-lived for sure. Like a Ferrari, it went from zero to sixty quick.

    The whole 'binary gender' thing was coined by linguists mainly for fictional writing and for story telling, though this predates English, or to be specific, predates Anglicized Breton. I know I botched that, but at one point, most of the vocabulary we commonly use, was unheard of, or considered 'dirty talk' (lower than commoner class talk #Classism), and most certainly, back then, being feminine was definitely different as femininity was reserved to the higher class people, those that had wealth were more feminine in appearance. Yeah.

    The whole thing about the separation of masculinity and femininity came about in several stages but was purported by the Church and State CoOp. In America, it started more or less with the Industrial Revolution, and then, from there, different industries took the separation in different directions, eventually making the distinction what it is now. However, the separation worldwide dates back to the Roman Empire waging war against Paganism.

    Back then, Celtic, Saxon, Nordic people were very similar between the sexes, and this was useful because of the roles each sex played (fathers and hunters/mothers and gatherers) but even then, there were many transfeminine, transmasculine, transenby, among others, because the role of the self-made individual mattered far more. This pissed off the Romans, well, no; it was because the Romans wanted their land for nothing and the Saxons said 'F*CK OFF' essentially, and rightfully so.

    It was only after blood was spilled and the Regionals fled, the Romans claimed what was left, and 'cHrIsTiAnIzEd AlL tHe KiNgDuMbS!'

    Oh, and yeah; it was also after that, Rome's frail and diseased, sickly women became the dominant XXV traits.

    Yep. Imagine if the Romans had lost, we wouldn't be discussing this, would we? It wouldn't be crossdressing either, I don't think.
    I dunno, but I do know this. You're always a pleasure to hear from and aesthetically pleasing to look at.

    Love, hugs, and best wishes (did you get a lot of snow from that massive snow storm?)

Leave a comment

Please note, comments must be approved before they are published