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!

Ask Hannah!

I’m interested in cross dressing but how can I hid my male parts?

You could tuck, but I prefer a gaff.

Wearing a gaff does require a little tucking, but a gaff makes it easier to do so. I wear gaffs from The Breast Form Store and En Femme. You can read my thoughts and reviews on what the Breast Form Store carries here.

While we’re on the subject, I would love to mention that En Femme carries vegan leather leggings with a built-in gaff. I was skeptical at first but my goodness does it work.

Wearing a gaff takes some time to get used to. If you are in pain, you are wearing it wrong. You’ll know you’re wearing one, but it should feel similar to you knowing you’re wearing a thong or a bra. You notice it, you feel it, but it doesn’t hurt.

You should also wear one for a bit to becomes used to it. Wearing it while walking, sitting, standing…

Hope this helps!

Love, Hannah

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