Different Sides of the Same Coin

As hard as it may be to believe, I have a very difficult time talking about myself. I am often embarrassed? Self conscience? about myself.  I am uncomfortable with praise and I struggle to receive compliments.  This could be anything from my boss telling me I did a good job with something or Hannah receiving an email about something I wrote or a photo I posted.

At least in real life.  If I get a nice email or a comment on social media I find it easier to respond to it, probably because I can take my time to process what I am reading and I can take as much time as I need to write and rewrite and rewrite and rewrite a reply.  I often agonize and over-analyze every word I write in a reply to make sure I come off exactly what I mean.  

But it’s not just compliments.  It’s everything.  I have had a website for a long time and I have written a lot about myself, my experiences, my opinions, thoughts, fears, and dreams.  I have bared my soul (not to sound tooooo dramatic) often.  It’s easy for me when I am writing something and then posting it for anyone in the world to read.  

I do feel… awkward when I write something and then someone mentions it when I see them in real life.  If Hannah sees her friends and one of them asks about something I posted on my website then I feel incredibly self-absorbed.  What I post online are not necessarily the same things I would talk about in real life, if that makes sense.  

I suppose I forget sometimes that I have a social media presence and people read what I write and sometimes mention to me what I posted when they see me in the real world.  I think my website makes my life look more glamorous than it really is.  I don’t think of myself as famous, or as a celebrity.  Not at all.  God knows I am easily humbled when I see my reflection or see how many more followers another t-girl has on Twitter.  Yes, photo shoots look glamorous but please know that when I do shoots outside there’s a really good chance I changed outfits, such as in the picture below, in a port-a-potty.  

I know! Shattering so many illusions!

Although I don’t think of myself as famous, I am aware that what I write is read by others.  Whether it’s two people or five hundred, I am just grateful that someone finds what I write about worth spending time reading or commenting on.  

Just as I have a hard time being a (again, this sounds very egotistical) public figure or a voice in the transcommunity (I do believe that ALL t-girls are a voice in our community) I find that in my boy life I have a hard time discussing Hannah and her life.  It’s one thing to talk about a new eyeliner with my wife, it’s another thing to talk to her about an upcoming photo shoot for En Femme or about a big box I receive in the mail of clothes to review.  In my boy life I find it… well, a little embarrassing to talk about Hannah’s life and the things she does or is asked to do.  The lives that both of my gender identities have could not be more different.  I write something on Facebook and I may get a couple of likes.  Hannah posts a picture on Twitter and gets a hundred.  No one cares about the boy’s opinion, but companies send Hannah makeup and shoes to review.

I think I would feel just as awkward if I had the same… ah, status in my male life as Hannah does.  The boy will never be famous, that much I know.  And I’m totally fine with that.  As I get older I am relieved by that, not that the boy does anything that would lead to any sort of notoriety.  If I were to write a book in my male life I would feel just…  weird talking about it.  If I were to be asked to sign someone’s copy or go to a book signing or whatever I would feel really awkward about it.  The boy being in any sort of spotlight is not a comfortable idea for me.  The boy is not, nor does he want to be famous.  Thank god he’s not.  It’s strange enough that Hannah has some level of “celebrity”.  

I started thinking about this last night when talking with my wife about a photo shoot I have scheduled for Saturday.  Sometimes in boy mode I have a hard time talking about Hannah.  On some levels my lives couldn’t feel more different.  I can’t imagine scheduling a photo shoot for the boy, but it’s pretty normal for Hannah.  Sometimes that drastic difference hits me and I feel very self aware and, in a way, kind of silly.  To clarify I don’t feel silly being en femme.  Not at all.  But my god, scheduling a photo shoot?  It’s about as vain as it gets.  Who do I think I am doing something like that?  It’s pure hubris, pure ego.  

In my boy life I never think about  whether I look attractive.  I don’t think about my boy clothes.  I might wonder if my tie goes with my shirt but really that’s about it.  Hannah thinks about cute all the time.  Do I look cute?  Do I feel cute?  Is this dress cute?  

I am often struck by the huge contract in my closet.  A few dress shirts and pants, some ties…  on the other I have everything from gowns to skirts to PVC dresses to… well, the list goes on.  But every once in awhile I think about how different my lives are.  What I do in either of my genders, what I think about, and of course what I wear.  There is very little overlap between Hannah and the boy.  I think this side of me would surprise almost everyone I know in my male life, but photo shoots, writing a book, modeling, running a trans support/social group, having a website…  that would be even more of a surprise.  I know my male life is pretty mundane and predictable to most people and that’s fine.  It’s true!  I like routine, I like planning my day, I am a creature of habit.  But Hannah’s life is anything but.  

Sometimes I’ll be in a meeting at work and I’ll be daydreaming about a dress I ordered.  Sometimes during a makeover I am thinking about an upcoming work project.  I think it’s normal for us to think about other aspects of our lives, but sometimes I wonder what my colleagues would say if they knew if I was wondering if the stockings I ordered would arrive in time for my next photo shoot.  Fortunately that is something I will never know.

I like having two genders, and I enjoy the lives both the boy and Hannah have.  My two genders, my two lives, are a wonderful break from the other.  When the boy life is stressful I can look forward to a makeover and a photoshoot or shopping…   On the opposite side of the same coin, I love ending a hectic but wonderful day en femme unwinding with a book.   

What a Friend We Have in Crossdressing

Years ago I knew someone who had absolutely zero interest in anything.  It’s not like they were lazy or weren’t ambitious or anything, they were a fine person.  Kind, friendly, just really a decent person all around.  As I got to know them I would ask about their interests and hobbies.  They didn’t have any.  They weren’t into music or books or sports or fashion or anything.  I asked what they did when they weren’t working which is usually an indication of one’s interests but again, nothing there.  Some television shows but that was it.  This was privately baffling to me.  We were good friends at one point and in the time I knew them they never mentioned anything that interested them.  They had no dreams, no plans, no goals.

They seemed to be happy and well adjusted but they never spoke about anything they were excited about, or something they looked forward to.  Of course, we all know people who go with the flow and take things day by day but this wasn’t that.  I’ve always been someone who looks forward to things with a lot of enthusiasm (even if I don’t express it).  I get excited about delicious food, going back to a book I’m reading, my next adventure en femme, the mail to see if my new outfit was delivered that day.  I have plans and dreams and goals for both of my gender identities.  Knowing who I am and knowing what made me happy I had a hard time relating to this person.  How could anyone not have something in their life that made them happy?

Of course as time marches on I realize that perhaps they were happy with everything they had.  Perhaps they were simply content and were at the point in their life where they had everything they wanted.  A small, simple life.  If that’s the case, then, well, I’m a little jealous of them.  I sometimes feel my goals are too ambitious and wonder if I will get discouraged if my dreams don’t come true.  Perhaps all of their dreams have been realized.

I don’t think it takes much for me to feel content or happy.  Normally.  I mean, I feel anxious and restless and bitchy and I sometimes have a hard time letting go of something, but once I remind myself how lucky I am, how safe and healthy and satisfying my life is, then I stop feeling sorry for myself (if that’s what I’m feeling) and I start to feel better.  It’s all about perspective, I suppose. I have stressful days at work or a sudden unexpected expense to take care, but really, if I can start the morning with coffee and leggings and end the day in a nightgown and a good book, well, what more could I want?

As people get older it’s not uncommon for them to lose interest in things.  To stop pursuing new interests, new hobbies.  It’s understandable.  Life isn’t easy, the days are long, and we’re all exhausted.  Sometimes it’s all we can do to make it through the day and crash on the couch and zone out for a bit with a television show.  I have days like that, too.  As life passes it’s not always easy to find time for the things that make us happy, things that relax us, that bring joy to our lives.  We know they are important but let’s face it, we all experience burn out, especially as we live through this damn pandemic.  

Many things that we like to do aren’t an option right now.  Traveling isn’t a good idea, spending time with our family and friends isn’t recommended, going out to eat just isn’t fun at the moment.  Frankly everything sucks.  But we will get through it.  Eventually.  Not without scars, though.

Although this side of us does, can, or has caused a lot of anxiety, fear, confusion, despair, turmoil, stress (and a zillion other things), this side of us, once we strip away all the unpleasant emotions and thoughts, this side of us brings us so much joy.  

Isn’t that wonderful?  We are so fortunate to have something in our lives that makes us so happy.  I can’t tell you how happy a new dress makes me, how much I like selecting my panties for the day, slipping on a nightgown at the end of the day, a new shade of lipstick.  I’m sure you feel the same way too.  

This isn’t to say much other than just express how happy I am to have something in my life that brings me such joy.  To bring so much beauty and content and fulfillment into my life.  I hope you feel that way too.  Yes, it’s not always easy to have this side of us and this side of us often brings challenges (to put it lightly) but on the most basic and smallest levels underneath all that stress there is beauty.  

Love, Hannah

Connecting the Dots

I hate the word “journey” when it comes to this part of our lives.  It sounds so trite, so cliched, so…  simple.  I suspect I also hate it because it’s probably the most accurate term for all of (gestures vaguely) this.

How did I get to where I am?  How on earth did I find the confidence (or ego) to do what I do?  Whether it is modeling or blogging or simply going to the mall, I didn’t do these things easily or all at once.  It was a step by step (ugh) journey.  I can go back and connect the dots as to how I got here.  We all can!  Regardless of where you are today you arrived at this moment because of what you did yesterday or last week or two years ago.  If you are wearing panties today it’s likely because you bought them.  And you bought them because you worked up the courage to do so.  And that courage came from accepting this part of you, and acceptance started with acknowledging who you are and what you wanted.

Throughout this journey how we identify might change.  As soon as I learned the word ‘crossdresser’ I identified that way.  A decade or so I identified as transgender.  Although I am still both of these, I feel most comfortable identifying as ‘bi-gender’ these days.  It feels more accurate, more nuanced.  More me.  Not all of us think too much about these labels but based on the emails I get and the search terms that are used to find my website there are a lot of us who wonder if they are a crossdresser or if they are transgender.  

If we wonder who we are and if we are unsure of what describes us best it’s sometimes easier to think about who or what we aren’t.  When I have come out to others I get asked the typical questions:

-Do I want to transition?  


-Oh, so you do drag?


-So, this… turns you on?


-Are you gay?

I am not attracted to men

These questions hopefully help answer if I want to take hormones, who I want to sleep with, or if this is a fetish.  Sometimes I feel that answering yes to any of these questions would help someone understand me a little bit better and easier as these can help frame someone like myself into something that others have some familiarity with.  Most people can name someone who is transgender, most people know who RuPaul is, and (almost) everyone has a kink.  In a way these questions help someone else connect the dots.  “Oh, you wear dresses BECAUSE you’re going to transition” or “You wear makeup BECAUSE you do drag”.  But when someone like myself is outside of those parameters it is a new experience for someone.  We are asked these questions because they help frame who we are to someone else.  Typically men who wear makeup or dresses (according to television shows and movies) are kinky or going to transition.  When we are not these things it kind of puts us in a different light that someone else isn’t used to.  If we aren’t going to live full time and if this doesn’t arouse us, then who are we?

I don’t need to explain who I am to most of those that are reading this, just as you don’t need to explain who you are to me.  I get it.  I get you.  You get me.  We understand each other.  We speak the same language.
Once I moved onto clothes other than lingerie and started wearing makeup and having a femme name I didn’t think I was simply crossdressing anymore.  Transgender seemed to be a better, more inclusive term.  As I mentioned earlier bi-gender seems to be the best fit. I believe that crossdresser, drag queen, bi-gender, agender, gender non-conforming, gender queer and other terms are more specific ways to identify but are all under the transgender umbrella. 

But why?  Why is that the best word?

Well, it’s kind of by process of elimination.  I don’t think of what I do as drag.  I don’t feel I am performing or putting on an act.  Once I felt that wearing “girl clothes” was more about expressing one of my gender identities than it was about the clothes themselves the word crossdresser wasn’t quite enough.  I like being part of the T in the LGBTQ+ acronym but the word does have a certain set of expectations, in a way.  A lot of people think that someone who is trans will or is or has taken steps, legal and or physical, when it comes to making permanent changes.  Yes my gender presentation can change throughout the day as I go back and forth.  The gender presentation I have when I wake up is not always the same gender presentation six hours later.   My mannerisms, my perspectives, my friends, my pronouns, my name, are all different as I go from one gender expression to the other.  Hence bi-gender feels the most accurate way for me to identify.  

Of course, sometimes I feel it would be nice if we could just simply be people and eliminate all expectations and norms when it comes to gender and clothes and everything but that is not happening soon.  Or ever.
I know I overthink labels and at my core I am simply who I am.  Sometimes I get fixated on trying to explain or understand myself (gender identity and in other ways), especially to others (hypothetically).  I suspect it has a lot to do with belonging, having a community, knowing there are others like myself.  I won’t ever forget how happy I was when I first heard the word crossdresser when I was in grade school.  To know that there were others like myself, to know that there were so many like myself that there was a word for us.  That word connected the dots for everything I felt, wanted, and wore.  I had a similar feeling when I heard the word transgender when I was in my early twenties.  As I got older ‘crossdresser’ seemed to be predominately synonymous (with many people) with sex/fetishisms.  Not that there is anything wrong with sex or a kink, but that’s not what it was for me.  ‘Transgender’ seemed to be about who I was, not what I wore, if that makes sense.  ‘Bi-gender’ I feel is the end of my dot-to-dot journey in terms of, well, terms, I guess. 

For those who are comforted by the rainbow of terms that are out there, how did you come to identify as that specific term?  Do you find terms comforting?

Love, Hannah

Hurricane Eye


2020 was a loooong year and I was really looking forward to flipping the calendar to 2021.  I know changing the calendar was really only a psychological thing, though.  However, it was still a little bit of a relief to be out of a really stressful year.  There are more things to be positive and optimistic about in the next few months.  Spring is sloooooowly on its way, vaccine distribution is getting better, and we are getting closer to a normal life day by day. 

For many 2020 was a traumatic year and I don’t use that word lightly.  Trauma is an interesting thing as we usually don’t see the impact of something until it is safe to react.  When something horrible and scary is occurring our brains can shift to survival mode allowing us to simply survive what is happening and we can react emotionally to it when the threat of danger passes.

Last year we saw so many things we enjoy get put on hold, whether it was a vacation or celebrating an event or just going to the mall.  The little things are important as it gives us something to look forward to.  My life is filled with little things that I am excited about.  But when these things aren’t an option, and it’s really unclear when we can plan something, then we realize how important they are to us.  

As things start to improve, I am feeling less stressed, less anxious, less depressed.  I feel the pressure and fear of last year ease its grip on me and I feel… lighter.  Happier.  The idea of walking around a museum this summer without a mask feels like it might actually happen.  Again, its the small things.

But as the stress eases, I realize I am starting to process on an emotional level what the last year has been like.  This is coinciding with getting older and feeling like I have less time to do the things I want to do more than ever before so it’s been real fun dealing with all of this.  It’s not quite a mid-life crisis (at least it doesn’t feel like that) but it’s more about doing things that I want to do before it’s too late, and starting to prepare for the rest of my life. It’s like being in the eye of a hurricane. I feel calm while life and uncertainty whirl aggressively around me.

Feeling peace in the chaos

On a practical level this means making sure my affairs and finances are in order.  I am not saying I am preparing my will or anything like that but when your eye doctor recommends bifocals it’s not hard to think about aging and everything that comes with that.  You know, like death and making sure my wife is taken care of when that happens.

Goodness this is all so heavy for a Friday morning.

My point is that now that certain parts of life are slowly returning I can start planning things again.  Or at least think about what I want to plan.  Some of the things I want to do are a result of me thinking about what I want to do before it’s too late.  Sure, I want to go out to dinner and try on dresses at the mall and these are things I want to do as life starts returning to normal, but what about the other things?  The things I want to do while I still can?  The big things, the milestone things.  Part of life returning back to normal includes being able to travel again, but these days I am thinking about traveling en femme.  Flying pretty is a big goal for myself.  I should do that.  I want to do that.  I will do that.  It might not be until next year when we can hopefully without a mask, but for the first time in a long time that opportunity feels more likely as each day passes.

As I get older I am more reflective and I look at things differently.  And thanks goodness for that.  I feel I am thinking about the smaller, more important things, but also about the big things, too.  Over the last year I have really missed Hannah.  I mean, I am always Hannah even in boy mode just as I am him when I am her.  My clothes and attitude and confidence change as my presentation does but I can’t shut off my other gender, if that makes sense.  My thoughts, feelings, emotions, hopes, fears are often jumbled together between my two genders. 

This past year I’ve learned a lot and I have had a few revelations. How has this year changed you?

Love, Hannah

Ask Hannah!

I decided I wanted to try wearing makeup and wearing women’s clothing. I am married and so far my wife is very supportive and even did my makeup last weekend! I ordered a few clothes on En Femme ( thanks for advice) and may get a wig soon. My question is how long did it take you to “like” how you look as a woman? I fear it’s going to take forever and I feel so old!!

Hi!  It sounds like you have a wonderful wife.  
Being en femme is a humbling and empowering experience.  I think some of us feel that when we have all the “right” items (wig, clothes, makeup) everything will magically come together and our reflection will show the side of us that we have been yearning to see for countless years.  Our first glance into a mirror can create a number of different feelings.  Sometimes we can be amazed at the beautiful girl in our mirrors, sometimes we are crushed with disappointment.

And sometimes we see the potential.  Not quite how we want to look, not quite how we imagined, but…  it’s a start.

When our reflections are not everything we hoped it would be, then we need to make a decision.  We COULD give up, but let’s face it, that’s not easy or likely.  This is not a side of us that goes away.  But I do get it.  It might seem hopeless, our worst fears are realized because we look exactly what we were afraid of: a man in a dress.  Crossdressing takes time, it takes money, it takes patience.  Don’t like how you look in makeup?  Pay for a makeup lesson.  Try a different foundation.  Watch more tutorials.  Your dress doesn’t fit?  Get your measurements and get an outfit that is in your size, not the size you’d like to be.  Stumble in heels?  Strap on those stilettos and practice, practice, practice.

The first time I was completely en femme, which was about ten years ago, I was enraptured.  I didn’t look like a man in a dress and a wig, I was unrecognizable.  At least that’s how I thought and how I felt.  Of all the things I was thinking in those first moments I think the thing that was the loudest was that I could see something I could work with, if you will.  I was on cloud nine the whole evening.  

I quickly learned that dressing up is a different experience and comes with different feelings every single time.  There are times when I will start dressing and feel blah about how I look but then when I do my makeup my attitude improves and turns things around.  The opposite is also true.  I might have a killer dress but sometimes my makeup just doesn’t come together and kills my excitement for my outfit.  These experiences and fluctuating feelings do not stop.  So many small things impact how we feel about ourselves and when I am en femme I am filled with many small things.  My forms, my pads, my outfit, accessories, makeup, hair, my body shape…  It all needs to come together.  It’s like baking a cake, I suppose.  If you don’t have the right ingredients it’s just not going to work.  

The photo on the left is me feeling cute, but not looking cute. The photo on the right is me looking cute, but not feeling cute

AND!  Sometimes everything can go right but sometimes we just don’t feel it.  We might look cute, but we don’t feel that way.  How we feel will win out (for good and for bad) EVERY SINGLE TIME.  I have dresses that I feel are just kind of… meh but if I am in the right mood it becomes the cutest dress in the world.  Of course the opposite is true, too.

So, to answer your question, I more or less liked how I looked right away, but that doesn’t mean I always like how I look.  I still have plenty of times where I feel I look like a man in a wig.  

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

A Better Son/Daughter

Years ago I wrote for Frock, a magazine focusing on the trans community. It is sadly no longer being published. The other day I was thinking about an article I wrote shortly after I came out to my mom.

The article was very much written in the moment and was very, well, optimistic. I had hoped my relationship with my mom would have improved and she would get to know Hannah. In my naivety I had thought that by opening up to my mom would have improved our relationship.

My relationship with her has gotten better, actually. But it’s not because of Hannah. Time did that.

Coming out will always change things. We only have one chance to do it and I wish I had discussed this with her in a different way. I understand myself and gender identity in a different way compared to when I wrote this in 2013. I came out as a crossdresser, not as transgender or bi-gender. Today this revelation would go a different way.

Love, Hannah

I remember sneaking into my mom’s closet all those years ago and trying on pretty much everything.  I was very careful to put everything back how it was.  Every time I would dress up I would think to myself that she could never find out about this.  So last year I was surprised to find myself wanting to tell her about my crossdressing. 

Like my most crossdressers, my hobby has certainly grown and evolved.  Once I accepted I was a crossdresser, I was mostly drawn toward lingerie.  At that point in my life, I would have never dreamed of telling anyone.  As I got into my early 20’s, I started sleeping in nightgowns and wearing dresses and skirts once in a while, though never for very long.  At the time, wearing “real” clothes wasn’t something I was used to.  It wasn’t until my wife taught me how to do make up and helped me buy a wig when wearing a blouse and skirt really felt right.  I adopted the name ‘Hannah’ for when I was dressed up, and soon Hannah had her own life.  Her own website, new friends and in a way, a different personality than the male part of me.  My wife started to notice differences between “me” and Hannah.  Hannah was more patient, she listened better, she was more vulnerable, she communicated better…she understood my wife in ways her husband didn’t.  As Hannah, I feel I can relate to my wife in different ways.  In some ways, crossdressing has really strengthened our relationship through communication, hard work and love.  I am a lucky girl, and a lucky man. 

It was a warm spring night and my wife and I were on our porch having a glass of wine.  I was wearing a blouse, black pencil skirt and stilleto heels.  “So…when are you going to tell your family?” my wife asked.  I smiled, I had been thinking the same thing.  Back when crossdressing was just about panties, the idea of telling anyone was out of the question.  Whether its panties or boxer shorts, no one wants to know what anyone wears under their clothes.  But as Hannah became, in a way, a real person, I wanted people to meet her.  After a few months, I told my sisters and brother.  It’s difficult to explain crossdressing to someone, but I think they understood. 

My relationship with my mom had always been difficult.  In my teens my parents went through a rather nasty divorce.  The divorce was a good thing, it should’ve happened a long time before that, and perhaps that’s where my anger started.  My mom and I fought constantly.  Once I entered my 20’s I calmed down a bit but my mother and I were never really close.  As I got older, I wanted to have a better relationship with her.  I always felt I had a wall between her and I.  When I told my siblings about my crossdressing, I felt a wall came down.  I wanted that with my mom and by telling her, I hoped that it would break the barrier between us.  I would be vulnerable and honest with her.  Telling someone about crossdressing is, in a way, giving them power.  Its saying that they know something about you that few people understand, and to please be mindful as to what you do with this information as it could change the way people see me.  I have been lucky that everyone I have told has been accepting and happy for me.  But if my employer were to find out, I would likely be out of a job.

On a Saturday night, we sat down and I acknowledged our difficult relationship and wanted to be closer to her.  I told her I was a crossdresser.  She was shocked.  I had expected all the normal questions about if I was gay or going to transition…but she never asked.  I told her that I had been crossdressing all my life, how I was never ashamed or confused by it and how happy I was.  She told me that she loved me and that she loved Hannah and she just wanted her children to be happy.  Her reaction and acceptance surprised me just as much as I had surprised her.  The conversation could not have gone better.

I spoke to her after what I told her had sunk in a bit.  She was still digesting what I told her but she still loved me.  Since that night, I have making more of an effort, more than I’ve made in the past, to be a better son.  I hope someday she meets Hannah.  I think she would like her.

Related reading

So, This Happened

Meeting Your Heroes

Ask Hannah!

I wondered if you had ever traveled on a plane en femme? If so how was the experience? I am both terrified and thrilled in equal measure about the idea of sitting down next to a random person for six or seven hours dressed as a lady and seeing how I react. I guess what worries me most is the obvious question of whether I’d get hauled out of the line at security. I am in the UK where attitudes are OK but I still don’t know what they’d do if the scanner picks up a bra wire and breastforms as well as my male tackle. I’m not sure I’ve the courage to risk having down to go down to my bra and pants in a side room to prove I’m not concealing drugs in my breast forms or in some sort of disguise. Any help or experiences much appreciated!

I have yet to fly pretty but it is definitely one of my goals. I had hoped to do that this year but it’s not looking likely. Once masks are no longer necessary then I will start planning a trip.

On a positive note, flying pretty, from what my friends tell me, is actually a lot less stressful and problematic than what we are afraid it will be. The TSA is also well trained for girls like us:

TSA recognizes the concerns that some members of the transgender community may have with certain security screening procedures at the nation’s security checkpoints. TSA is committed to ensuring all travelers are treated with respect and courtesy. Screening is conducted without regard to a person’s race, color, sex, gender identity, national origin, religion or disability.

Have fun and safe travels!

Related reading

Flying Pretty

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

Let’s Talk About Sissys

I fully accept that I will never completely understand why I am who I am.  It could be genetics, it could be nothing more than how I am wired.  I know I also overthink this aspect of myself.  I mean, I never wonder why I like watching documentaries or why I like waking up early.  I know!  SO boring, lol.

The fabulous rainbow we are all under includes so many… types of trans people, for lack of a better word.  My definition, my interpretation, my explanation of the term ‘transgender’ is basically anything that is outside the normal societal perspective of gender in a binary sense.  Someone who takes hormones, a boy who wears nail polish, someone who has they/them pronouns, it’s all trans, baby.  This is a unifying term, this is our common ground.  If you were to create a Venn diagram, a drag queen, a crossdresser, a t-girl, would all overlap as transgender.

It’s similar to how you can be a music lover, but you identify as a jazz fan and dislike country.  And I know no one really “identifies” as a jazz or a country fan, but I think you know what I mean.  Jazz and country are types of music, drag and crossdressing are aspects of being trans.  I don’t know, the analogy makes sense to me.  

Although I don’t do drag, I can absolutely see the appeal of it.  It would be so fun to break out of my shell and perform for others, to wear fabulous dresses, extreme heels, at least for a night.  I don’t feel that taking estrogen is right for me, but I understand why some feel it’s the right decision for them. 

The nut I can’t seem to crack is the whole sissy life.  I mean, the dresses are absolutely adorable, but other than that, I don’t see the appeal.  I also know I don’t have to.  So many parts of life, interests, hobbies, seem to fall under either getting it or not.  I could be wrong, but it seems that a significant portion of sissy life is about humiliation, sex, and submission.

And I know I could be mistaken, or oversimplifying this, and I am likely 100000% wrong in this.  Thanks to the media and top Google results, you could easily assume that crossdressing are those things as well.

Not that there’s anything wrong with that.  I am not here to pass judgement on anything, fetish or otherwise.  Promise.

I get a lot of emails from girls like us and if I am speaking in VERY general terms, it FEELS that MOST (not all) messages from those who tell me they are a sissy, or curious about being a sissy want to put on a frilly pink dress and being at the mercy of a man.  

Please note that this is not an invitation for anyone to send me their fantasies.  Please don’t.  And while we’re on the subject, I don’t know where you can find a sexual partner or where you can go to be sissified.  Kindly stop asking me, please.  🙂  

I mean, I understand sex.  I like sex.  I also know that clothes and presenting as a gender other than the one most people see, can bring out a different side of us, and sometimes that is a sexual side of us.  I get that.  I also understand the appeal of being en femme and enjoying the attention from men, intimate or otherwise.  One of the things I enjoy about being en femme is kind of taking time off from my boy life.  The stress, the responsibilities, all of that.  Spending the day in a pretty dress and shopping for clothes is a wonderful little vacation. 

And although I don’t necessarily relate, I also see the appeal of being submissive.  I listened to a podcast about a guy who visits with a dominatrix.  He has a very stressful life and is responsible for a lot of important decisions with his company and he said that for a few hours a week he is tied up and has no control or responsibilities.  He makes no decisions, he just…  checks out.  He said it wasn’t about sex anymore, it was about being able to unwind (while being tied up) after a hellish week.  No one is asking him to go to a meeting, or make an important decision, or discuss the projected fiscal budget for Q3.  I suppose it’s healthier than drinking or escaping reality with drugs.   

I have a lot of enlightened readers who are so amazing at helping me understand things, so I am wondering if there is something more to this that I am missing.  I mean, on a perfunctory level, it seems like it’s all about wearing a frilly pink dress (again, the dresses are adorable) and getting nailed.  Is that all there is?  Does it need to be about anything else?  I am either overthinking or oversimplifying this, I feel.  Is it similar to the guy in the podcast?

I don’t need to understand every aspect of gender/kink/fantasy and there’s zero judgement about if this is really all about the clothes and sex.  If it is, okay, sounds good.  I just am wondering if there’s something that I am missing, a perspective anyone can offer.

Thank you, you beautiful ladies, you.

Related reading

What is Crossdressing?


Ask Hannah

The T Word

Sexy Monday

Love, Hannah

Maybe She’s Born with It (or maybe it’s genetics)

We ask ourselves why we are like this.

Our partners ask us why we are like this.

It’s just…  how we’re wired.  We’re just born this way.  

I do not think gender identity is a choice.  It’s just who we are.  I believe this side of us is a part of us when we are born.  It may take years, even decades for us for us to realize there is something there inside when it comes to stepping outside of the traditional and societal gender roles.  When I was young, around five years old, I remember seeing mannequins at a department store modeling lingerie.  Something just clicked for me.  A part of my heart, my brain, opened a little bit and I realized that I was mesmerized by these beautiful clothes in a different way than most boys would be.  

Yes, a boyn is often interested in girls and lingerie is a different and sensual world that most boys aren’t involved in, but moments like that made me want to wear lingerie.  I couldn’t stop thinking about what it would be like to wear stockings and a garter belt.  It was then that I started to pay attention to how I felt, what I thought about when it came to “girl things”, whether it was makeup, a beautiful dress, or how boys and girls were “supposed” to think, act, and feel.  

I think many of us think that this side of us might be a fetish.  And sure, it might be for some of us, but lingerie, heels, dresses are not sexually stimulating to me.  When I am en femme, or even simply underdressing, I feel amazing, sexy, beautiful, but never aroused.  

But…why?  I don’t know.  It’s just who we are.  Some people like to link certain events in our lives to this side of us.  I have heard everything from an absent father, a domineering mother, unaddressed trauma, repressed sexual identity as reasons why we are drawn to the other side of the closet.  There may be some truth to that for some of us, but I don’t think that there is anything inherently psychological connecting me to my gender identity.  Sometimes I think I am enlightened and I simply ignore gender norms and do what I want, and where what I choose.  Clothes are clothes, there’s no need to genderize them.

I don’t think any of us can point to a definitive reason and say THIS IS WHY I AM WHO I AM.  Some of us feel we were born with the wrong body, some of us feel were assigned the wrong gender at birth, some of us…  well, we go back and forth like a ping-pong ball trying to find a reason why.  I get tired of looking for a reason why I am who I am.  Ultimately I don’t think it’s anything I’ll understand and I try not to speculate about it.  In many ways, I am comforted by accepting I was born this way.  

BUT!  When we say we were born this way, could there be a genetic reason for it?  What if it’s not trauma, enlightenment, or anything else, but something biological wiring us in this way?  Could our genes impact our gender identity?

We are about to enter the OVERTHINKING ZONE, so fasten your garter belts, ladies.

My friend Marci and I have been chatting about this over the last few days and she sent over a couple of articles you may find interesting.  Ultimately I can’t say if biological factors influence who I am, or who any of us is.  If it wasn’t for spell check I wouldn’t even be able to spell neurologist, let alone be able to make any sort of decision about the link between genes and femme jeans.  I suppose you could make an argument for this as well as against it.

However, would I like this to be true?  Would I want there to be a connection between my brain and my gender identity?  Would I like there to be a biological reason I was born this way?  

I don’t know.  I really don’t.  People fear the unknown, people hate those who are different.  I understand this is rather broad and a massive generalization, but there is discrimination and violence against people of different races, different genders, different sexuality.  It wasn’t long ago that people who were left-handed were thought to be communists.  The trans community is already hated enough as it is, giving people a “reason” to hate on us is something we don’t need.  I mean, if this was true haters are going to say things like “See?!  they’re genetically different!  Their brains are messed up!  There’s something wrong with them!”  And soon enough there will be talk about “fixing” our brains or conversion “therapy”.  

On the other hand, it’s comforting that this is just how I am because of subtle variants in my genes (and subtle differences in my femme jeans, lol).  I don’t think gender identity is a choice, and the idea our biology influences that is, well, it’s kind of nice to have an explanation about why we are the way we are.

What do you think? Do you think there is something to this? Would you like it to be true?

Love, Hannah

Ask Hannah!

Any advice on a first night out en femme?

Going out for the first time is a life-changing experience.  And I don’t say that lightly.  
I felt so many things my first real time out en femme.  I was scared beyond belief.  My nerves were a wreck, my legs trembled, I was jumpy, I was excited. 

Whenever I go out en femme, the first interaction with someone else really kind of sets the tone for the day.  It’s a positive experience it really starts me off in a good mood.  Luckily most times I go out en femme my first visit is for my makeover.  The two artists I see on a regular basis also make me feel welcome and beautiful. 

My first interaction on that crucial day couldn’t have gone better.  The cashier at the coffee shop was smiley and I felt a huge wave of relief.  I accomplished something!  I did it en femme!  I took my coffee and I felt like I was walking on air.  It was wonderful.  I spent the rest of the morning shopping and just soaking up the day.  

As wonderful as the day was, it almost skewed my expectations for the next time I went out.  My second outing was at a busy mall on a Saturday afternoon.  Most people were nice or at least indifferent, but I also noticed more…  confused looks, more stares, more suppressed smiles.  It was depressing, especially after my first time out.

When you go out for the first time, or the hundredth, you should prepare for everything.  This includes practical things, such as what you should have in your purse.

Before I go out, I always make sure my purse has:



-Finishing powder


That’s the fun stuff.  The reality is that I have a lot more in my purse than makeup.  I recommend every t-girl have the following in their purse:

-Cash.  This is pretty obvious but I use cash for everything when I go out.  If I want to get a coffee or need to pay for parking, I use cash.  I like cash because I don’t run the risk of turning over my credit card (with my male name) to a cashier.  I also bring my debit and credit card just in case.

-Proof of car insurance.  If you get into an accident or get pulled over, you’ll need to provide proof of insurance.  Simple enough but plan for the worst.

-Fully charged cell phone.  Pretty self-explanatory.  You’ll need it in case of emergency.  Any emergency.

-Roadside assistance information.  You need to know who to contact if you get a flat tire.  Sure, I can change a tire myself, but no way I am doing that in a dress or heels.

-Driver’s license.  Again, if you get pulled over…

-Spare car key.  If you’re not used to carrying a purse, you might forget to place your keys in it.  A spare key tucked in your purse saves a call to a locksmith.

-Medical insurance card.  Again, plan for the worst.

-A friend.  I don’t mean bring a friend with you, though shopping is a lot more fun if you do, but if you’re out to anyone in your life, drop them a message to let them know you’re stepping out.  It’s good to let someone know you’re out on the town in case you need help.

-I would also recommend downloading the Uber or Lyft app.  If you run into car troubles and need help, having this on your phone can be a lifesaver.  I have an app on my phone and I have multiple accounts associated with it.  One for my male life, one for Hannah.  I’ve used Uber as both genders and I’ve never had an issue.

There is a practical side to being who we are, such as the things listed above, but we can’t ignore the emotional and mental side either.  We can look amazing, but if we don’t feel amazing, then our confidence is shot, no matter how beautiful we are.  If we are so hung up on passing or blending in, then we may never feel ready to go out en femme.  It’s important to remember that not everyone likes us and not everyone will treat us with respect.  It will happen.  You’ll have moments and experiences that range from wonderful and affirming to humbling and humiliating.  Don’t let it dull your sparkle.

And above all, be safe.

Related reading

All Dressed Up and Nowhere to go

Just a Small Town T-Girl, Living in a Lonely World

It Will Never be Okay

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!