Ask Hannah!

I am very attracted to trans women. I’m not sure exactly why or what it is about them that causes this attraction. Although I’ve never been with a trans women before, I feel drawn to them.
I guess my question is, am I gay, bi, or attracted to the woman I see within a trans woman?

Hi!
Trans women are women.  Being attracted to a woman, trans or cis, doesn’t mean you are gay or bi.
All women are more than the body parts that she has.
Love, Hannah

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

Ask Hannah!

I am having a hard time finding people, male or female, that accept my enjoyment of wearing female attire. My roommate is gay and does not accept it, nor have any of my past gay friends. Yes, I would like to explore gay sex but the guys I have met have been too aggressive sexually. I know that I am border line on everything but you must have come across boys like me that want more and can’t find the right folks to learn, explore, and grow with. I am open to all and any advice

Although we don’t need approval to be… anything or anyone we are, acceptance is pretty necessary.  Or, at the very least, we would like to not be shunned or judged based on who we are.  Even though it is almost impossible to predict how someone will respond when we come out to them, typically (and this is being VERY generalizing) the reaction falls into one of there three scenarios:


-Thank you for being honest with me!  I encourage you to be true to yourself and dress how you want

-I may not understand this part of you, but it doesn’t change how I feel or think about you

-This side of you is weird and confusing and feels wrong and strange to me.  My opinion of you has changed significantly 


Again, these are very broad and certainly don’t cover every possible outcome, but I think for the purpose of this question these sum it up rather succinctly.


Part of accepting ourselves as a crossdresser also comes with the understanding that this side of us, this preference and enjoyment of wearing lingerie or heels or countless other beautiful things, can’t REALLY be explained or understood.  And trying to understand it is really unnecessary and impossible.  It can’t be expressed in a satisfactory way.  If we try to, the person we come out to usually just responds with wanting to know more.  Sometimes there ISN’T more to be said.

I like to wear dresses.

–But WHY?

They’re comfortable and make me feel good

–But WHY?

Pretty soon we get to the point where there’s nothing more that can really be said.  The WHYs, for the most part, are really asking “but you’re a BOY, how can you resolve that you are a boy that wears girl clothes?”.  I don’t know, I just wear what I want.  Again, a highly unsatisfactory and not very helpful response.  Lady Gaga nailed it, we are just born this way.  

Of course, I don’t need to explain this to a t-girl or a crossdresser, or anyone non-binary.   What I’m trying to do is explain how someone who is cis gender may process this side of us.

Anyway!  Back to your question.  Yes, it is hard to find others that will accept this side of you.  Most people have the need to understand… ANYTHING before they can accept it.  And, like I said earlier, this side of us can’t REALLY be understood.  I’ve been wearing “girl clothes” for decades and I’ll continue to do so and I will never understand WHY (beyond me just… WANTING to).  I’ve come out to three romantic partners in my life.  One hated it, one loved that I was open and honest with her as well as with myself, and of course, the third married me.  I’ve come out to a few friends and my siblings and each reaction has been varied and has fallen anywhere between “that’s awesome!” and “please never discuss this with me ever again”.  It stings but it is what it is.  You can’t MAKE someone accept who you are.  At the most, you can just hope they come around.  

Although you would (logically) assume that someone in the LGBTQ+ community would accept someone else who is also LGBTQ+, it’s not always so, and truthfully, it’s not really an equivalent.  Gender identity and sexual identity are pretty separate as far as I feel.  Wearing stilettos and makeup doesn’t change who I am attracted to.  My brother is gay and, like my cis gender sisters, doesn’t really get why I have a closet full of dresses, but they still love and accept who I am.  Of course, this doesn’t mean that they want to get a coffee with Hannah, but they know who I am.  

As for being curious about sex with men (or with anyone else), I am afraid I can’t be much help when it comes to that. 

It’s natural and normal for a crossdresser to want to share this side of us.  But what does that mean to you?  I knew what it meant to me when I came out to my wife.  I dreamed of getting dressed and going to the mall with her.  Although that hasn’t happened we’ve had countless girls nights in and it’s been absolutely magical.  You mention wanting to learn.  Are you looking for another crossdresser to teach you how to walk in heels or select the right clothes and sizes?  Are you looking for someone to teach you makeup?  If so, you may need to broaden your search a bit.  I learned how to do makeup thanks to three different teachers:


-My wife.  She showed me the differences between highlighters and bronzers and concealers.  She taught me the basics and broadened my horizons when it comes to makeup beyond just eyeliner and lipstick.  She showed me how to apply foundation and the basics

-Other crossdressers.  I read a lot of websites and forum comments and watched makeup tutorials about having more traditional masculine facial features and how to wear makeup and what products to purchase.  I learned a lot of techniques, such as beard covering, this way

-Finally, a professional makeup artist.  I booked a private makeup lesson and learned how to contour and minimize and enhance different aspects of MY face.  Every face is different and techniques that work for some faces won’t work for others.

You may, of course, also need to alter your expectations.  Many of us want to find an amazing person to have a fulfilling and incredible life with.  BUT you add in crossdressing to that relationship (or really, ANY relationship) it’s going to complicate things.  Coming out to someone you are romantically linked with will FOREVER alter your relationship. 

Before I came out to my wife (my girlfriend at the time) we had a good relationship.  Skipping ahead all those years later, we still have a good relationship but coming out to her has not always been easy but through communication and patience we adapted.

Before my wife I dated a girl who was 100000% accepting of what I wore, but goodness that relationship was not healthy for either of us.  When we ended it, part of me wondered if I would ever find someone who accepted my crossdressing the way she did, but staying in an unhealthy relationship BECAUSE they accepted my wardrobe choices was not a good idea.

In my opinion, if you want a relationship and you want crossdressing to be a part of it, you need to start with finding the right person, and then coming out to them.  Work on developing that friendship, that trust, that honesty.  Of course, you need to come out to them while you are in the early stages of dating, especially if them accepting your crossdressing is essential when it comes to a committed relationship.   

There are places online one can go to when it comes to finding other crossdressers.  I would recommend joining crossdressers.com or urnotalone.com.  Although I am rarely on these sites anymore, I have made friends through them.  Go to the site, create an account, and look in the forums and discussion posts for others in your area.  

To summarize, you can’t MAKE anyone accept your crossdressing.  I never made my wife accept it, but after some time passed she grew to understand that this side of me was, well, a part of me that wasn’t going to go away.  As two people create a life together they soon learn there are aspects of the other’s life that they may not understand or even like, but through honesty and communication they may come to accept the other person’s habits and personality and even clothing preferences.  

I really hope this rambling and almost aimless response helps, lol.

Love, Hannah

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

Ask Hannah!

Recently a young associate at work declared his choice to be gender neutral in a vanilla work space. Not sharing my own perspective with them I was a sympathetic listener. Yesterday the person in question showed up with blue nail polish and received a cackle from female associates. The anxiety of the moment led me to change the subject and move the associate along. Wondering how best to assure my own fears, and adapt to the situation. I have cross dressed many decades myself but remain closeted. Your thoughts?

There are always, always, always going to be those who mock people for just about any reason.  People criticize others for their race, their sexuality, their gender identity, and just about anything else.  This will not change anytime soon.  And if I am feeling pessimistic, I don’t think it ever will.  It’s painful to be reminded that there are others that we know, others that we work with, and even others that we are related to who will go out of their way to be cruel to someone.  The associates you mention made a choice to be mean.  They could have kept their comments to themselves but it sounds like they wanted to openly mock your co-worker.  It sounds like you did your best to de-escalate the situation.  Good for you!  It is not an easy and comfortable position to be in.  

Many of us are terrified of being outed.  At the same time, part of some of us would like to be out to more people in our lives.  We long for that for a variety of reasons, whether because we ourselves want to wear blue nail polish or because we are exhausted from keeping who we are a secret.  We may wonder who it would be safe to come out to.  Of course, there’s no way we can ever predict how someone else will react to this revelation, but sometimes people will show their true selves and will telegraph their thoughts and opinions to others.  It sounds like that was what happened here.  It shouldn’t be this way.  We all should have the right to express our gender identity and wear what we want.  It might be legal (from a human resources and legal perspective) for a non-cisgender person to wear blue nail polish but that may not stop others from mocking that person.  

As for adapting, we live in a world where people are cruel to others regardless of the laws or the workplace protections that are in place.  An office can implement policies banning discrimination (in all it’s forms) but that still isn’t enough to stop some people’s reactions.   Sometimes I will hear one of my co-workers say something about someone who is LGBTQ+ and I will think to myself that I will have to be extra careful to not let myself slip up when it comes to my own gender identity.  Of course, were I braver I would confront that person but I am not.  Well, perhaps it’s not about courage but realizing that some people just cannot change.

Of course we don’t have to adapt.  We can be the change.  Talk to human resources if you feel that there are others who are creating a hostile or toxic work environment.  This, like any effort to transform a culture, takes a tremendous amount of courage but change happens when one person speaks up.  We live in a world where people are intentionally cruel to others, but it doesn’t have to be this way.

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

Ask Hannah!

I am 59 yrs old and am happy as a male. But I’ve know for most of my life that there was another me trying to get out. I decided this week to begin that journey. My question has to do with overload. There is just so much to research and so many places to look I am beginning to get frustrated. I know my decision is good and true. I just don’t want this to turn into a train wreck. Any ideas or thoughts?

This is a very good question.

When some of us have accepted and embraced who we are, it is common to feel excited and giddy.  Once we accept who we are (or at least an aspect of ourselves) we have, in a sense, given ourselves permission to be who we want and dress how we feel.  This can easily lead to The Pink Fog, however and we sometimes need to rein it in a bit.

But feeling overwhelmed is also pretty common and it’s not something we talk about enough.  When we come out to someone, it’s not uncommon for them to feel overwhelmed by this revelation.  The whole… concept of who we are to them has been changed and they will very likely look at us in a completely new light.  Coming out to someone can feel like taking a weight off our shoulders but that weight is often transferred to the person we come out to, particularly if that person is one’s significant other.
But before we can come out to someone else, we need to come out to ourselves.  We need to say to ourselves “I am a crossdresser.”  “I am transgender”.  “I am non-binary”  Or even “I am not sure who I am or how to identify, but I like to wear panties.”  Once we do that, we will (hopefully) slowly begin to embrace ourselves.  


Aaaaaaand then what?

No matter how you identify, the commonality is that you are not cisgender.  There is something wonderful about you that doesn’t align with the traditional expectations of the gender you were assigned to at birth.  Like you, I am happy in my male life, AND I am happy with my femme life.  I don’t want to choose one gender over the other for the rest of my life so I happily bounce back and forth.  I do, however, keep my toe in my femme life when I present as male as I am always wearing panties.  So, there’s that.  Embracing your new non-cis life and new gender identiy doesn’t mean you have to do EVERYTHING or even do ANYTHING.  Yes, I am transgender but that doesn’t mean I HAVE to take hormones, live full-time, come out to anyone, or transition.  I’ve identified as transgender for almost ten years and my life and gender identity hasn’t changed that much.  

You mention starting your journey.  Think about what you want our journey to look like.  You write that you are happy being male so my assumption (and I admit I could be wrong) is that you don’t feel transitioning isn’t your destination or goal.  I can relate.  I don’t feel that way either.  My journey started before I turned five years old by trying on my mom’s heels.  Over the last few decades I evolved.  I did a lot of reflection and tried on different clothes and thought about gender and read about gender and even spoke with therapists.  Through all of that I realized who I was, who I wanted to be, and what I liked to wear.  I also realized who I wasn’t and what I didn’t want.  This was my journey.  Today my gender presentation is either BOY or GIRL or somewhere in the middle.  I work from home and I am usually wearing leggings and a femme hoodie.  Unless I am on a Zoom call, lol.  Being comfortable and happy in these identities took time and patience.  

Let your heart be your guide.  Don’t feel you have to rush into anything.  Find out what is right for you.  Don’t feel you have to commit to a gender identity.  Take your time.  Take a break.  If you feel frustrated, do something else.  Take time away from the internet.  Slip into something you like to wear and watch a movie.  Enjoy the journey.  Talk to a gender therapist.  Your journey isn’t going to be a linear path.  It isn’t going to be smooth or without obstacles or setbacks.  Go easy on yourself.  Think about what WANT to do.  Think about what you want to wear.  Yes, it can be overwhelming to think about changing your gender presentation and everything that could go with it.  Going from boy to girl for me requires forms, padding, shaving, makeup, wig, clothes, heels, and false eyelashes.  It’s exhausting to just type that.  Just remember that there are no rules or standards when it comes to your gender presentation.  

And yes, I can relate to feeling overwhelmed.  When I was in my early twenties I had just gotten out of a relationship with the first person I came out to.  Coming out to her was also a sign that I had accepted and would soon embrace who I was.  She wasn’t too fond of my crossdressing (which is how I looked at who I was at the time) so it wasn’t a part of myself that I could talk about, let alone DO.  After I had begun to move on after the break-up I decided to see what this side of me was all about.  I knew I loved to wear lingerie, but was there more to this?  I went to a store in Minneapolis that sold a lot of fetish wear, including shoes.  I had owned heels before but there were the boring, kitten heels that places like Wal-Mart sold.  They weren’t cute and weren’t really my size and I would always purge them after a day or so.  But one evening I decided I wanted a pair of stilettos that fit.  I drove to the store and started to look at the selection.  The girl working there showed me some options and pretty soon I was trying them on.  It was amazing.  She offered some advice and soon I was strutting around the store as if I was born wearing four-inch heels.

“I have something else you may like,” she said.  Still in the black patent stilettos, I glided to the counter and she took out a pair of breast forms.  I had never seen breast forms before and was amazed by them.  They looked real, they felt real.  As I was looking at them she told me she had a friend who did drag and they would love to help me with makeup if I wanted them to.  At this point I felt a little anxious and overwhelmed.  I went into the store because I was ready to buy (and keep) a pair of stilettos.  I wasn’t ready for anything else.  I didn’t know if presenting femme was what I wanted.  At that point in my life I just wanted to wear lingerie and stilettos. I politely declined the offer, bought the heels and left.  It would be another ten years before I was ready to consider my next step in my journey.  Today I own several pairs of breast forms, have had makeup lessons and had more makeovers than I ever thought I would have.  I wasn’t ready for these steps then, but goodness I am now.

Enjoy this side of you.  Be kind to yourself.  Be patient with who you are.

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

Ask Hannah!

Hi I’m a straight guy look to date a Trans women. I’m sick of the same old thing with women. I’ve decided that I would like to date a trans women. I don’t know how or where to do so. I’ve been on the dating sites and I hate it. I have not let my family or friends know, but am just so in love with trans women. Do you have any pointers for me this is all new to me I have never been with a trans woman or guy.

It’s easy to misinterpret anything that is written or said.  I want to be as gentle and as kind as possible when it comes to any Ask Hannah! question.  I recognize that it takes a lot of courage and nerve to ask for advice and the last thing I want to do is make anyone feel bad or silly when they need help and guidance.  One of the reasons I have a website is to educate others when it comes to everything from relationships to walking in heels.  I would never claim to be an expert on anything and I am honored and humbled when someone asks for my advice or perspective on something.  


Of course, I also want to avoid embarrassing anyone when they need help.  I take no joy in humiliating anyone or calling someone out.  I do get a lot of emails and Ask Hannah! questions about relationships and that includes asking about dating t-girls.  To be honest, I usually just delete them without replying as they tend to be crass in nature.  However, I thought it might be helpful to gently and kindly touch on a few things you wrote in your question.  


If identify as straight, you are (presumably) attracted to women.  Transwomen are women.  Being attracted to a woman, cis or trans, simply means you are attracted to women, or at the very least, that woman.  If you are attracted to a t-girl, it doesn’t mean you aren’t straight.  Does that make sense?  Also, dating or, in your words, being with, a transwoman is certainly not equal to being with a guy.  I do cringe a little when I get an email or comment along the lines of “I’m not gay but you are beautiful”.  Like everyone else on the planet, I am more than my anatomy, I am more than my genitalia.  


You write that you are sick of the same old thing with women.  Why do you think dating a transwoman would be any different?  Be careful to avoid generalizing anyone.


I understand you may be hoping I could direct you to a dating site or something similar.  I am sure Google could assist with searching “dating trans women”.  The help I am (kindly and sincerely) hoping I am providing is perhaps some perspective and clarification.  I hope you find happiness, I know it’s painful to be lonely.

Love, Hannah

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

Ask Hannah!

I’d love advice on how to further explore going out into the world en femme.

Leaving one’s home en femme for the first time is one of the most significant things you will ever do in your life.  It’s not something you will ever forget.  It does get easier over time, however.  


Like most aspects when it comes to gender identity and gender presentation going out en femme is a series of baby steps.  The first time I went out was at night and I went to an LGBTQ+ bar.  The bar hosts drag nights and a girl like me is a pretty common patron there.  No one batted a false eyelash at me.  I went to the same bar a couple of times before I was ready to go out during the day and to frequent a place that wasn’t specifically for the LGBTQ+ community.  I had a beautiful dress that needed altering so I made an appointment with a seamstress at her shop and went to several fittings before the dress was finished.  It was an amazing experience and my confidence and comfort grew and continued to do so.


I have written a lot about going out whether it is about what to have in your purse, going out if you live in a small community
, as well as not letting the fake concept of passing holding you back from strutting out en femme.  Just stay safe and have fun!

Love, Hannah

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

Ask Hannah!

With Halloween coming just around the corner my wife and her sister would like to go as Charlie’s Angels.  They bought me this cute green dress to wear. My question is what heels do you think are the most comfortable to wear for longer periods of time? My wife does not know anything about my crossdressing and maybe this is also a good time to hint to her that I really enjoy it.  What do you think?

Every foot is different so I can’t say definitively what heel is right for you.  I choose my heels for the day (or night) based on how much walking I am going to be doing and what outfit I am wearing.  As much as I want to wear my six-inch rose gold stilettos, I know it’s not the best idea if I am walking outside on slippery, icy sidewalks during a Minnesota December.

If I am doing a lot of walking or standing I tend to select a lower heel.  Again, sky-high stilettos are my jam, but let’s face it, your feet (and eventually your legs and back) will start to hurt before too long.  On the other hand, I have tall heels that I can and do wear for hours and hours at a time without any sort of discomfort.  Again, every foot (and heel) is different.  

I recommend picking out the heels you WANT to wear, the heels that work with WHAT you are going to wear and practice wearing and walking in them for a few hours.  Practice going up and down steps.  Think of it as test driving your heels.    

As for using Halloween as a way to come out to your wife, every relationship (like every stiletto) is different.  How one person comes out to their partner isn’t necessarily how someone else should.  What I do know is that coming out to your partner will irreversibly and significantly impact your relationship FOREVER.  Coming out to my wife while we were dating is still up there among the most important and life altering conversations we have ever had.  And that conversation still continues (on some level) to this very day.  Coming out to your partner is something that can only be done once.  Regardless of how well you know your partner (or anyone else you may come out to) you really have no way of knowing how they will react.  They may be angry, hurt, confused, excited, relieved, or emotional. 

It’s important to treat coming out (and any potential reaction) with the appropriate gravitas.   Casually mentioning that you enjoy crossdressing, or hinting at it, might be appropriate for some relationships.  It wouldn’t have been the right method for when I came out to my wife.  Yes, perhaps if I had casually mentioned it to her after only a couple of weeks of dating that would be different.  But by the time I came out to her we had known each other for a long time, we dated passionately and deeply and intensely.  We spoke of getting engaged and moving in with each other.  I should have come out to her before we had conversations about our future.  By the time two people are married they have made serious and important commitments to one another.  Coming out after getting married is waaaay more serious than coming out while dating.  Treat the conversation as serious as it deserves to be.  Again, coming out to anyone will likely bring up a lot of emotions and conversations so please consider the weight that this revelation will likely have.

Love, Hannah

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

Ask Hannah!

What were your feelings and your thoughts the first time you used the ladies room?

The first time I used the ladies room was at a LGBTQ+ bar which is probably as safe as it gets.  I was still a LITTLE nervous, though.  Thankfully it was an uneventful experience.  I did take a few selfies and reapplied my lipstick just because I could, lol.


Since then, I have used the ladies room countless times and they have been without incident.  I do use a family restroom if there is an option to do so, but so far every visit has been fine.  Indeed, if anything there’s small talk with the other ladies about shoes or the outfits we’re wearing.  


I am fully aware of me being a t-girl in the ladies room, though.  I never want to make others feel uncomfortable but I am conscious of the fact that a transgender person in a bathroom is a political hot topic.  This… controversy seems to have died down a little over the last few years but I know at any time someone might react in a negative way and might cause trouble.  


I will always recommend the app Refugee Restroom when it comes to non-binary people looking for a bathroom.  


Love, Hannah

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

Ask Hannah!

Are any of the MN T-Girls transitioning?

As much as I cringe at the word, everyone, cis or trans, is on a journey.  We are all at different points in our lives and as time passes we will continue to change and evolve.


That being said, some members are transitioning, some are still figuring that out, and others are perfectly content to going back and forth between gender presentations.  The group has existed for almost ten years now and many girls have been members for almost as long.  I have gotten to know so many amazing t-girls over the years and have been fortunate to see my friends evolve and change over time.  Of course, this evolution and change isn’t necessarily transitioning, it can be more about becoming more comfortable and confident in who they are.  It’s always amazing to have a t-girl attend her first monthly outing only to find out it’s their first time EVER leaving their home.  Within a few months they are strutting confidently in a busy mall or have come out to their friends.  


Of course, I am not immune to changing either.  I have known for decades that transitioning wasn’t where my journey was going to take me.  Despite countless times going out en femme and doing all sorts of things, I know that Hannah’s world, her life, isn’t where I want to live 24/7.  I am happy to live two lives, to have two gender identities.

The changes I have gone through have more to do with becoming more comfortable in stepping out and interacting with the rest of the world.  I care less about what others might think of me.  It might sound a little strange, but I forget I am a t-girl when I am out in the real world.  I am just a girl living her best life… for a little while, anyway.  I always go back to my boy life but I have a good life regardless of my gender presentation and I am blessed to have options.

Love, Hannah

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

Ask Hannah!

Is it okay that I love to dress up even if I will never pass?

For starters, it will never be “okay” to present as a gender that is different from the one someone was assigned to at birth.  At my most pessimistic I don’t think the world as a whole will ever be accepting of a boy wearing a dress or nail polish or anything femme.

At my most optimistic I also don’t think most of the world really cares.  Most people are too preoccupied with their own lives to really care what someone else is doing or wearing.  Sure, they may think that a boy wearing a skirt is a little unusual but after a few moments they probably won’t give it a second thought.  But I exist for myself.  I dress for myself and I am not going to stop being who I am because of someone else.  


Also!  Passing isn’t real.  There are no set standards one must meet in order to be “allowed” to be a girl.  No one, cis girls or transgirls, are too tall, too… anything to be a girl.  


So, to answer your question, yes!  It is absolutely okay to dress however you like.  True, not everyone will be thrilled or accepting but you need to live your own life and not be concerned with what others might think.  And yes, I know, it’s easier said than done, but I promise you the more you dress the less you care about how others might think.  

Love, Hannah

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