The Crossdressing Life

Although the term is probably outdated, when I first heard the word ‘crossdresser’ I immediately associated myself with it.  By definition, I was indeed a boy who liked to wear women’s clothes.  I was around twelve years old when I started to secretly identify as a crossdresser and although later in life I learned how sexually charged and fetishy the majority of the world thought of the term, I was still a crossdresser with a few caveats.  By and large it felt that the world viewed crossdressing as a kink.  For me, crossdresser didn’t FEEL like a kink.  Yes, I was a crossdresser but it wasn’t really a sexual thing.  I didn’t want to dress up in lingerie and have sex, I wanted to dress up in lingerie and read a book.  

As time passed the word still had it’s complicated meaning (at least to most people) but I started to feel that although I was a boy that liked to wear women’s clothes, it didn’t seem to fit.  I started to de-genderize a lot of things such as clothes and even myself.  A dress wasn’t a piece of cloth (or leather!) that a girl wore, it was a piece of cloth that anyone could wear.  Yes I had “boy parts” and traditionally boy features, but really, did we have to label people as men OR women?  Why not both?  Why not neither?  What difference did it really make?  My journey (ugh) took me from panties to skirts to makeup to wigs to finally a femme name.  The word ‘crossdresser’ simply didn’t feel right anymore.  It didn’t feel… big enough, if you know what I mean.  I was more than a boy that liked to wear women’s clothes.  I was a different person, or at least a different aspect of myself when I was en femme.

I’ve identified as transgender (using my own personal meaning of the word) for a while now.  If I want to get more specific I identify as bi-gender.  I am happy and content in both of my gender presentations.  I don’t feel conflicted about my identity regardless of the pronouns I am using or the shoes I am wearing.  But if we take the words ‘transgender’, ‘non-binary’, and ‘bi-gender’ off the table, and we look at EVERYTHING, whether it is a person or a piece of clothing through a binary lens, then yes, I am a boy who likes to wear women’s clothes.

So!  Let’s talk about that.  I think many of you who are reading my website (based on the comments and emails I get) are like me.  We love panties and lipstick and pretty clothes but part, or even most of our lives, have a stiletto in the boy world.  I know that’s how my life is.  Being bi-gender means I have more than one gender identity and wardrobe.  Having an identity, gender or otherwise, means that identity may come with obligations and responsibilities as well as friends and relationships.  Hannah has friends that my male self does not.  If Hannah’s “job” can be considered blogging and working for En Femme, then her career is different from the career I have in my male identity.  

My point is that both of my lives are very different from each other, as I imagine both of your lives are as well (if identifying as bi-gender is appropriate for you).  BUT! even in my boy life I am always connected to my femme side.  I am connected to Hannah’s world through clothes, whether I am awake and wearing leggings or sleeping in a nightie.  When I am in boy mode (either because that’s the gender I choose to present as for the day or because I have to attend to obligations that my male life has) I am, by definition, crossdressing.  

Of course, what one DOES leads to who one IS.  I believe in nuances and since I separate my life and gender identity (and closet) into two halves, If you wanted to get into the weeks and get specific, I suppose the male me is a crossdresser whereas Hannah is transgender.  Together “we” are bi-gender.  Does that make sense?  It does to me and I think many of you reading this understands and likely can relate.  I do think that I personally put too much time and energy into terms and it’s rather unnecessary but there you have it.

Even when I am presenting as male, I am never 100% “boy”.  Even now I am wearing a femme cardigan, panties, and leggings.  I am also wearing a boy t-shirt and two days worth of facial stubble.  I am a boy wearing women’s clothes (if we insist on genderizing clothes).  As soon as I finish this cup of coffee I am off to the gym where I will wear a pair of black leggings that look like boy workout pants but I know the truth.  Afterwards I will put on boy clothes (and panties, of course) for a doctor appointment.  When the day is over, I will pick out a nightie and go to bed.  And tomorrow the in-betweening begins all over again.  Since so much of my life and day are punctuated by clothes, and since Hannah is always thinking about what outfit to wear on her next adventure, it’s easy to think that *this* is all about clothes and wearing what I want as opposed to gender identity.  But I know it’s not.  It’s more than that.  When I am en femme I am in a different mindset and a part of me emerges that, although is there in male mode, it is more easily revealed.    

I write about my life and my day from a transgender perspective, but since I believe in nuances, I don’t think I write about being a crossdresser (if we are splitting hairs) very often.  When I am en femme part of my mind is in survival mode.  This manifests in a few ways.  Is there anyone I know in this store?  Is anyone following me in this mall?  Is the sidewalk too icy for these heels?  In male mode I am far less paranoid but still aware.  When I choose my panties for the day I need to make sure I am careful if I need to kneel down to tie my shoe if the panties have a high, pink, lacy waist band.  If I am wearing a bra I am very cautious whether or not the strap or band is visible.  I am very aware of who may be around if I am in the lingerie department of a store.

Aaaaand that’s really about it.  But it’s enough.  Yes, Hannah is looking out for a million little things when she is out, but she is not protecting or trying to hide that she is transgender.  I am read very easily and I am fine with that.  I have no problem with people knowing Hannah is transgender.  I know she is transgender.  I am not trying to blend in.  Although there’s no standard as to what a cis women looks like, between my square jaw, height, boy voice, broad shoulders, it’s not surprising that people think that I was identified as male when I was born.  But in male mode, I am fiercely protective of the fact that I am a crossdresser.  No matter which pronoun I am using at any given moment, I am on guard (is it any wonder I have anxiety, lol).  It’s just a different kind of paranoia but I do believe paranoia protects us, even if it drives us crazy.

Being a crossdresser isn’t easy.  It’s exhausting hiding this side of us.  I think on some level it’s harder to explain why a man likes to wear lingerie than it is to explain why someone’s gender identity is different than the one they were assigned to at birth.  But as hard as it can be, it IS wonderful.  I love having my femme life, AND I am also really happy crossdressing.  I love wearing panties every day, I love wearing a nightgown every night.  Clothes make me so happy.  And yes, I know that this is shallow and superficial but I wouldn’t change a thing about me.  

Love, Hannah

16 thoughts on “The Crossdressing Life

  1. I have also divorced myself from the term “cross dresser” because of its fetish connotations, although it is a term that the average person uses to describe a male like me who resists society’s contention that “boys don’t wear pretty non-bifurcated garments”. I prefer the term “skirt enthusiast” because that is exactly what I am and why I choose the clothes I wear when I want to look and feel special. There are women who love dresses and those who hate them, why can’t there be the same preferences amongst men?


  2. It would be most interesting to ask a number of females why they like or love to wear a dress and ask others why they don’t….one woman I know said to another woman that it isn’t practical – the fact that that woman who said that is a lesbian, does this make a difference? Interesting…Anyway, the other, older woman was surprised at this attitude of the younger woman. Is it the way that a woman is brought up? Does their age make a difference? Does this first woman feel embarrassed, that she may be showing her panties or too much leg? Sure makes one wonder.


    1. I think women who came of age in the fifties and sixties were taught that skirt wearing was an expectation of being female and there was enormous peer pressure to comply. Those who matured in the seventies and later were encouraged to decide for themselves how to express their femininity and many of them choose pants for “comfort” reasons, whether it be physical comfort of being able to be active or the emotional comfort of not feeling like they are “on display”. I would contend that between 10 and 20% of American women love wearing dresses, an equal number hate wearing them and avoid them at all costs, and the remainder would wear one if the occasion warranted it but would otherwise choose pants. All I ask for is the freedom to choose for myself, and on a breezy summer day, that would be a tiered ruffled maxi dress!


  3. you are “bi gender” but I note that the femme side leaks in to the boy but not vice versa.if you were forced to make a choice I bet you would opt for Hannah


    1. I GENTLY DISAGREE BASED ON WHAT SHE HAS PREVIOUSLY SAID, particularly her genuine love and affection for her brave and tolerant life partner. Ask her.

      Liked by 1 person

  4. Well, I see we lead pretty similar lives, I too have 2 wardrobes, enjoy my femme side, also I consider myself unusual in the aspect that I don’t know of any Trans people who do Blacksmithing for a hobby(mostly a male thing!) There are a small handful of female smiths out there but Trans? Haven’t met one yet, so definitely male mode for that as the club I belong to is all guys and some of the spouses come along to chat and socialize amongst them selves.


  5. I started as a cross dresser also.Now when I dress it feels different, like that’s who I am. My wife’s girlfriend, and I love it.


  6. A serious suggestion Hannah. The honesty and profoundness of your stated thoughts are extremely valuable to millions of men and women worldwide in understanding and living with girls and boys like us. Put some of your best works like this one together in book form and market it however you would like, but send me a copy autographed to “lerissa”, who explicitly asked me [you,i.e.] to do this for the anxiety ridden world of gender blending in all humans at some level. You are truly a national treasure; your appearance is silver, but your thoughts are solid gold. This is meant as a sincere compliment to a woman who looks beyond the treetops to the stars, and the infinite possibilities brought by allowing all of our innocent selves full expression. Also consider starting your own line of cosmetics and clothing, perhaps working with en femme, formerly , suddenly femme. As Loreal used to say “you are worth it”. Think of what you can do with the royalties you CAN MAKE FROM A LIFE I’M SUGGESTING FOR BOTH YOU AND YOUR SPOUSE . Your considered thoughts have been very good for this old girl, who thinks beards and mustaches are also fetishes, and that fetish is not a pejorative term. lerissa

    Liked by 1 person

  7. “If I am wearing a bra I am very cautious whether or not the strap or band is visible. ”
    LOL! I remember when I took a temporary job after I got out of college in which I lived on a construction site. You had to share a trailer with another person (two entrances and separated) but the washroom trailer was common. I went to the washroom to clean up and was washing my face when my neighbor came in. We greeted each other and continued on with business. I noticed that he was ne was occasionally casting furtive glances at me but shrugged it off (we were both topless, by the way).. After he had had left, I happened to look back over my shoulder at the mirror and saw the clear outline of my bra! Yikes! To his credit, he never said a word. I have been careful ever since… 🙂


    1. I have been turned onto a wonderful product! Evelyn & Bobby from Portland; OR. Make the defy bra and the defy Camisole , Absolutely amazing products , I wear the cami Everywhere & Every day, when wearing them they look like a tank top (just form fitting ) super soft and smooth , like a second skin. I feel naked when not! I so so enjoy the gentle hug it gives, and helps keep me warm on these cool Boston days!!! Also once removed you don’t get those lines carved into your skin from the bra straps and underwires, also great support for my forms I wear C/D size (daily) and these garments are awesome !
      Hope this helps someone love Lily


  8. I for myself an non binary or fluid trans, so I do stand out as a fem guy when I’m not full on fem, which I do about once a week
    People at work know and see me in all kinds of attire that is primarily gender neutral female clothes
    I’ve become very comfortable this way and each day I put on makeup and head for work loving who I am
    This has been a journey for me, yes I know Hannah not your favorite word, but it’s true
    Showing a bra strap at work or wearing obvious breast forms is just a normal day for me as a trans fluid person
    It took time to get here but I now am pretty happy with where I am so yes we all have different paths how we find that happy place on this gender spectrum


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