Crossdressing 101: Part 4

Hello class, welcome to the last day of Crossdressing 101.  It's hard to think about how much time has passed since you first sashayed into my classroom in one inch patent pumps.  Pretty soon you'll be strutting across the stage in five inch stilettos on graduation day.  

Over the past few lessons we have discussed crossdressing and different ways one can identify as we go beyond the world of "boys wear blue and girls wear pink".  I thought for today's lesson we would discuss our own personal gender identity.  While I was grading your homework I learned that many of you are wondering if you are more than a crossdresser.  Some of you seem to be scared of the idea of identifying as transgender.  To begin, there is nothing scary about being transgender.  And in my opinion everyone in this classroom is indeed transgender.  

Ashley?  Could you please put away your eyeliner and remind the class what identifying as transgender means and doesn't mean?  

Yes, thank you, perfectly said.  Transgender does not always mean transitioning.  It does not necessarily mean hormones, estrogen, surgery, or anything permanent.  I am transgender, but I have no plans to transition or change my legal gender or anything like that.  Being transgender is simply doing or anything that is outside what society views as traditional gender norms.  Identifying as transgender is anything that is outside of the traditional gender norms.  From there, there are different, ah, segments of identifying as transgender, such as crossdresser, bi-gender, gender fluid...

But I get it, I really do.  If you think that being transgender means you MUST or WILL or HAVE TO transition, well, it's understandable to be apprehensive about such a big change.  But that's not what it necessarily means, so please don't be scared of being trans.

Some of us start wearing lingerie and dresses and painting our nails because, well, it's so super fun.  I love looking cute, I love getting dolled up.  I love going shopping en femme.  Not only is this side a crucial part of who I am, it's also a side of me that I accept and embrace.  I love being who I am.  And that means I love BOTH sides of me.  I identify as bi-gender because I am comfortable presenting as either a boy or a girl.  True, stockings and stilettos are more fun than trousers and neckties, but I'm comfortable and feel like myself no matter what I choose to wear.

And that's the key.   

Is this side of you MORE than just having fun and expressing a side of yourself?  We know this side of us won't go away.  And why should it?  It makes us so happy to wear lipstick and panties.  But many of us wonder if this is a bigger side of us than, well, just a side of us.  How does one know if they are "just" a crossdresser?  How does one become sure that transitioning is or is not right for themselves?

Before I go any further, I want to address that gender identity is a VERY serious and personal subject.  Do NOT let me, or anyone else decide who you are.  If you are wondering if going to the "next step" is right for you, you should immediately meet with a gender therapist and your doctor.  Full stop.  They know more than I ever well.  I can teach you how to apply foundation, but when it comes to whether or not you should take estrogen that is not something I can, or will, answer.  

But I can discuss some things to consider.  As someone who has never felt like it was, well, wrong for me to be a boy, I want to make it clear that I don't know what it feels like to be unhappy that I am male (at least part of the time).  I have never felt that I was assigned the wrong gender when I was born.  And this is why I am bi-gender.  I am happy in both of my gender identities.  I know a lot of girls who have transitioned and they have all told me the same thing, that they felt unhappy, unconformable, depressed, and even angry when the world thought they were a gender that is different than how they felt.  They simply did not like being a boy, dressing as a boy, having to do boy things.  They felt a pull in another, more feminine direction. 

I can relate to being fascinated and drawn to pink and dresses and makeup and heels and lingerie.  But I never felt that wearing pants and such was ever, well, wrong.  I just wanted choices, I wanted options, I wanted to wear what I wanted when I wanted to.  And I started to.  And I still do.  

I don't feel anxious in boy mode.  I don't feel depressed when I wash off my makeup and take off my wig.  I don't feel a sigh of relief when I am en femme.  I don't feel that either of my genders is my "true self", or "the real me".  I always feel true to myself, I always feel real.

And that's how I know how I personally identify is the right fit for me.  When we embrace and accept this part of us (and please note that accepting and embracing are not the same thing), it's easy for us, and for others, to wonder where all of this is going.  When I went from lingerie to dresses and makeup and a femme name, it was natural for me (and for my wife) to wonder and perhaps be afraid of where all of this was heading.  As much as I tried to reassure her that transitioning wasn't right for me, it wasn't easy for her to, well, believe me after seeing me go from only panties to going out en femme over the span of a few months.  To her I'm sure it felt that me taking estrogen was only a few weeks away.  

But that wasn't the case.  It took her years to understand that where I was is where I belong.  Some of us have the same thoughts as our partners.  On some level I didn't know where all of this was going either, but I knew that my (ugh) journey did not include anything permanent.  No legal name change, no hormones, no plans or desire to live en femme full time.  How did I know?  I knew because I didn't hate being male.  My reflection, although incredibly boring, didn't make me cringe.  That's why I personally feel I am at the end of my journey when it comes to how I identify and where all of this is going, and where it has ended.

When we are en femme, it's easy to want to stay in "her world".  It's a beautiful world with so many fun clothes.  This side of us, when you take away the stress, the dysphoria, the paranoia, the fear, well, it makes us completely happy.  Who doesn't want that?  When I am en femme I am usually spending the day shopping, seeing my friends who are girls like us, at a museum, attending a play...  basically a lot of activities I am too busy to do in my boy life.  It's easy to associate being en femme with doing fun things, with being able to take a small break from the stresses of my boy life.  But it's risky to think that being en femme, or living full-time is a permanent break from the stresses of the life we have as a boy.  If I transitioned I'd still have the same stressful job, the same unreliable car, the same home.  There have been times I have spent the day en femme only to come home and catch up on a few things for work... while still in stilettos.  The things in my boy life are still there even when I am beautiful.  They are waiting for me "when I get back", so to speak.  

Please remember that this is my personal experience and feelings.  Is this the standard that you should measure when it comes to your own gender identity?  Of course not.  Bottom line is that if you feel anxious or confused by your gender identity and by this side of you, I would absolutely recommend speaking with a gender therapist and/or seeking out a transgender or a LGBTQ+ support group.

And with that ladies, our lesson is over.  You have all been the most attentive schoolgirls and it's been my honor to teach you.  Please push in your chairs and unless I am seeing you for detention, have a fabulous summer.

Love, Hannah


  • Bobbi Bubbles

    Super read! I’m like totally at awwe WOW!!! Really key points that have been on my mind for ever finally understand lots !! Thank you so very much 😘


  • Jane Elizabeth Mansfield

    Hello Hannah, terrific to read your input. I agree about crossdressingI dont hate being male, but love being enfemme.
    I appreciate CDH and TGH, and keep on with your sage comments. Jane

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