Ask Hannah!

How long did it take you to learn how to do your makeup? My second question is do you tuck your male parts? What do you recommend i use to tuck my male parts? Do you use silicone breast forms in your bra? What do silicone breast forms cost? Where do I buy silicone breast forms? Do you wear a slip under your dresses and skirts? Do you wear pantyhose? Do you wear a girdle? How do I learn to walk in stilettos and high heels? How do I learn to move as feminine as a real woman? Do you have a feminine voice? How do I feminize my voice? How often do you shave your facial and body hair? And finally how often do you feminize your eyebrows? And I am also wondering how you take your coffee black or cream and sugar or just cream or just sugar? And what size shoes do you wear in women’s shoes?  What is your favorite coffee shop? Do you or have you ever smoked cigarettes?

Okay, let’s jump in.  Round two..?

How long did it take you to learn how to do your makeup?

Makeup takes a lot of practice, mistakes, and money.  It took me about three months to be able to do a decent job and it’s something you’ll get better at the more you do it.  Don’t get discouraged.  Booking a makeup lesson is probably one of the best investments you can make.  You’ll probably never stop learning new techniques.  Just the other day I learned something new regarding eyeshadow.


My second question is do you tuck your male parts? What do you recommend i use to tuck my male parts?

I am afraid I cannot advise you on this.  I’m sure you can Google this with…varying results.

Do you use silicone breast forms in your bra?


What do silicone breast forms cost?

Quality forms can cost anywhere from $100 to $700.  I’m sure you can get them cheaper, but notice I used the word “quality”.

Where do I buy silicone breast forms?

I get my forms at The Breast Form Store.

Do you wear a slip under your dresses and skirts?


Do you wear pantyhose?


Do you wear a girdle?


How do I learn to walk in stilettos and high heels?

Slowly.  Start with a kitten heel (one or two inches) before the six inch stilettos.  Heel to do, glide a little, keep your leg straight, shift your weight and practice practice practice.

How do I learn to move as feminine as a real woman?

There is no standard as to how a woman is supposed to move

Do you have a feminine voice? How do I feminize my voice?

…or sound like.

How often do you shave your facial and body hair?

Each week, typically the night before I go out, if I am going out that week.

And finally how often do you feminize your eyebrows?

I don’t look at it as feminizing my eyebrows.  Again, there is no standard as to how a woman should look or dress or speak or move or style their eyebrows.  Yes, they may look more feminine but I think they also look better when I present as either of my genders.  I do get them threaded about every three weeks.

And I am also wondering how you take your coffee black or cream and sugar or just cream or just sugar?

Cream, no sugar.

And what size shoes do you wear in women’s shoes?

Depending on the shoe, it can be anywhere between an 11 to a 12.

What is your favorite coffee shop?

I used to love going to the Blue Moon Cafe and Cafe Southside, both were in Minneapolis and sadly they are both closed.

Do you or have you ever smoked cigarettes?

No and no.

Whew!  😉

Love, Hannah


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


Ask Hannah!

Hi Hannah may I ask you a few questions because I am a crossdresser just starting out. Do you dress full time? Why do you crossdress? Do you carry a purse in public? What do you keep in your purse? Do you go out in public dressed to such places as stores restaurants bars and coffee houses? Do you have a wife? Does your wife support your crossdressing? Do you want to become a transgender woman? Who does your makeup? And finally what restroom do you use in public?

That’s…a lot of questions.  Let’s get started!

Do you dress full time?

No.  I underdress full-time, though.

Why do you crossdress?

Any one of us could write a book on why we are who we are.  I write a little about this subject here.

Do you carry a purse in public?



What do you keep 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.

Do you go out in public dressed to such places as stores restaurants bars and coffee houses?

Yes.  I don’t drink so bars are not my thing but I have been to everywhere from gas stations to museums to a church to Target.

Do you have a wife?

Yes.  She’s gorgeous.

Does your wife support your crossdressing?

Yes.  Marriage and who are are is a lot of work, requires a lot of patience, understanding, and communication and is not very easy.  I write a lot about relationships here, here, and here.

Do you want to become a transgender woman?

I am transgender.  However, being transgender means something different to everyone.  I have no plans to transition or live full-time, if that’s what you mean.

Who does your makeup?

I do my own makeup but for special occasions and photo shoots I book appointments with Corrie Dubay.

Cherry Dress 3
Photography by Christi Williams

And finally what restroom do you use in public?

If there is a unisex bathroom I use that.  If not I use the restroom for the gender I am presenting as.  Refuge Restrooms is a good app to have on your phone.  According to their site, Refuge Restrooms is a web application that seeks to provide safe restroom access for transgender, intersex, and gender nonconforming individuals. Users can search for restrooms by proximity to a search location, add new restroom listings, as well as comment and rate existing listings.


Whew!  We did it!

Love, Hannah


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


Ask Hannah!

I’m curious if you’ve ever felt any hostility from the trans community regarding your definition of transgender? I mentioned on a Reddit post that I consider myself transgender even though I’m ultimately just a guy who likes to dress up every now and then, and I received a large amount of hostility and even some relatively harsh replies. I think I deserved some of it (saying I’m just a man who likes to dress up can definitely act to group others on the more “transition” side of things as an attempt of grouping them with me), but I was shocked at some of the comments (such as “no… you’re a crossdresser, and that’s it. Don’t use our term!”)

I’m just curious if you’ve ever had any similar responses, or what your view on the whole thing is.

This is a pretty familiar conversation our community has.  I have a friend who has a little joke about this:

What’s the difference between crossdressing and transgender?
Six months.

This is also a pretty common question we all ask ourselves.  Many of us start by identifying as a crossdresser and many of us will transition (no pun intended) to identifying as transgender.

I think some people feel that if it’s all about, and only about, the clothes, then it’s just crossdressing.  But once feelings and gender identity are factored in, then it crosses into trans territory.  Others say it takes hormones to strut into trans-land.

It’s not easy to explain who we are.  Usually we stumble through coming out and get frustrated because it’s hard to really pinpoint the reasons we are who we are.  It’s even harder for someone else to understand.

It may be hard but if we want others to understand us then we have to do the best we can to communicate with them.  Of course, you are under no obligation to explain to anyone (besides your significant other) who and why you are who you are, but if you do, then you need to take the time to do some soul-searching and kind of sort yourself out.  To this day my mom thinks I am a crossdresser as opposed to being trans.  Why?  Because that is how I can out.  I came out to her about five years ago and I didn’t quite do it correctly.  I told her it was about clothes, about dressing up, and that I didn’t know why I did it.  It is what it is.  Perhaps I downplayed it in an effort to spare her feelings or calm her worry?

But pulling these punches did me no favors.  Were I to come out today to her, or to anyone else, the conversation would be more about my perspective on identity and not feeling restrained by societal and gender norms and how I don’t know why I am who I am and that I don’t really care about figuring it out.  Just like I don’t lie awake wondering why I like coffee I don’t lose sleep over why I heart mascara.

The sticking point is that there are many perspectives and opinions on these terms and there’s no universally agreed upon definition.  I suppose it would be fair to say that these terms are open to interpretation and your definition is likely different than someone else’s.

What this thinking falls under is that there is no right or wrong way to be trans.  Just like there is no standard or expectation you must meet to be able to identify as a girl, you do not have check off certain boxes to be able to identify as transgender.  You do not have to wear a size 8 in heels to be a girl, you do not have to transition or live full-time to be transgender.

Just like you can’t let anyone tell you that you are or are not the gender you identify as, you can’t let others tell you if you are transgender or not.  If you say you are, you are.  Personally I would say you are transgender but my opinion means nothing.  It’s all about what you identify as.  I think the transgender term can, and does cover more specific ways to identify.  Some identify as gender-queer, agender and non-binary.  I think I identify as a bi-gender.  Crossdressing, drag, all of these terms fall under transgender.


If you haven’t done so already, I recommend reading Mia Violet’s book ‘You Are Trans Enough’ which talks about this better than I could.  I have never experienced any push back from our community about my definition.   In many ways my definition is my perspective and my opinion.  Were I to be challenged on it I wouldn’t fight to the death trying to convince someone else of my definition.  I would impress upon them that this is my opinion and no one has to agree with it.

I hope this helps!

Love, Hannah



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


Ask Hannah!

Hello, I really love to know how I could be more femme.  I am a very tall guy which I really hate.

There’s a zillion things you can do, and what makes one feel femme is different for everyone.  For some nothing is more feminine than bright red nails, or a matching bra and panty set or literally anything else.

You specifically mention being very tall.  How tall is too tall to be feminine?  Remember, there is no standard that one has to meet to be a woman.  I am also tall but once I learned to embrace my height I was that much happier.  I used to want to blend in.  I didn’t want to be noticed, I didn’t want to be seen.  I thought being tall would make me stand out more.  But I realized that I am going to stand out no matter what.  I wear bright pink dresses.  My makeup has more drama than a high school.  There’s nothing about me that blends in, so why not wear whatever I want?


So I rock the sky-high heels and I am hard to miss.  It’s funny, wearing tall heels makes me feel more feminine that I ever thought I could feel.

The best advice I ever heard about being a tall girl and heels was given by talk show host Wendy Williams.  She says it better than I ever could.

The best thing we can do is embrace ourselves.  Embrace all of you.  Your height, your body, everything.

Love, Hannah


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


Ask Hannah!


pink skirt 5
My eyes are up here, boys

I really want a nice breast form plate!   I have a more masculine chest and neck and would like it covered!   Do you have any suggestion! Price is not a problem just want something that looks real and is quality!   It will really help with my confidence! 

Thank you so much!

I don’t have much experience using forms or padding, though I (finally) started wearing breast forms about a year ago.  I actually really like them and I am surprised at how natural they look and feel.  I resisted them for a very long time as I wanted to be as natural as possible but I really feel that my forms are a part of me.  I was afraid that they would unattach or create some sort of wardrobe malfunction but no worries yet!

Suddenly Femme (also known as The Breast Form Store) sells a rather large variety of breast forms and breast plates, including one that looks rather convincing.  I’m glad price isn’t an issue, though.  🙂

Glamour Boutique also has an array of options.  They have a really nice page dedicated to reviews of different options that I would recommend you look into.

I hope you find one that you like!  If any readers have any suggestions please comment!

Love, Hannah


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

Ask Hannah!

untitled-1So last week in MN must have been really cold, yet you went out in that short skirt! Do your nylons provide any sort of warmth?  I doubt it.  So how does a girl stay fashion forward in such cold temperatures?

It was cold.  It will be even colder this week.

I hate the cold and one of the primary reasons is that I don’t like letting the cold tell me what to wear, and therefore I am usually freezing.

No, the stockings do not provide any sort of warmth.  I suppose I could wear thermal tights or leggings, but to be honest, I work really hard to keep my figure and I am especially proud of my legs.  I like to show them off.

I admire girls who can pull off a really cute and stylish look when the weather turns nasty.  When I see a girl wearing leggings and a cute sweater I always wonder if I could make a look like that work for me.  It would certainly be more sensible than a skirt like that and matching it with four inch stilettos.

What’s amazing about women’s clothing (and I don’t think there is such a thing as “men’s” or “women’s” clothing, but you know what I mean) is how cute, fun, and how varied it can be.  In male mode it’s shirt and tie…every. single. day.  But on the other side of the closet, it’s hoodies and yoga pants, skinny jeans and tank tops, t-shirts and jean skirts, dress pants and blouses, summer dresses and sneakers.  The options change with the seasons.  Right now the weather is giving us an excuse to wear infinity scarfs, tights, boots, cute jackets… the options are endless.  I never feel more jealous than when the seasons shift from one to another.

I do tend to dress on the more…dress-uppy side of things.  I love heels, dresses, dramatic makeup… I tend to stand out.  Not because I am amazing or anything like that, but I am a six foot tall t-girl.  Taller in heels.  People tend to notice me anyway.  Some girls dress to blend in and I think that’s wonderful, but I don’t think I’ll ever be able to do that.  So, if I can’t blend in, I may as well dress exactly how I want.

I do think about going a little more casual from time to time, but that hasn’t happened yet.

What are some of your favorite winter looks?  Comment below!

Love, Hannah


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



Ask Hannah!

Has Hannah affected your relationship with your wife?  Has your wife seen Hannah? Has she had “girls nights in” with Hannah? How does she feel about Hannah?  How has her relationship with Hannah evolved since your early  days of blogging?

I could probably write (and maybe I should) a book about the dynamics and evolution and impact that crossdressing/being transgender has on a relationship, but I will try to keep this concise.

Being who we are is likely hard on our partners.  This is not a part of us that will change or go away, so we will never “outgrow” this part of us, this is not a phase we are going through.  Too many of us try to suppress this part of us when we meet someone and start a relationship because we don’t want to scare this person away by revealing this part of us.

But of course no matter how hard we try to deny it, this is who we are and we shouldn’t try to do that.  What we should do is be honest with ourselves and be honest with our partners.  I get emails from people like us who tell me that they don’t plan on telling their partners about this side of them until after they’re married.  Their thinking is that it’s too late for them to go anywhere.  This is hurtful, cruel, unfair and dishonest.

I told my wife about this part of me after a few months of dating, once I knew I wanted to marry her.  I’ve come out to a few partners in my life when I felt the relationship was strong and serious enough.  At the time I came out to her, I felt that this was all about under-dressing and I didn’t have a “male mode” or a “female mode”.  I was just a man who wore panties.

But people change and evolve.

After we’d be married for a few years, she asked if I ever wore makeup or clothes other than lingerie.  I had, but never really to the point of a full makeover or head to toe with a wig and heels.  She did my makeup that night and helped me order a wig.  Up to that moment she didn’t really understand why I liked lingerie but she understood the feeling of wanting to be beautiful.

I started to buy dresses with her help.  My wardrobe grew and our relationship now had a new part of it.  We were both learning about Hannah and getting to know her.  We had constant and honest communication about what… all this meant.  There were times where she was concerned about me wanting to transition and where all this was leading to.  Those concerns faded over time.

It’s easy to understand her concern.  I went from wearing panties to doing my makeup and having a closet full of heels in a few months.  My evolution accelerated and it was like going from a nice leisurely drive to a million miles per hour.  But eventually I stopped my gender exploration and landed where I am today and her concerns about me wanting to transition subsided.

This part of me has allowed me to be more open, honest, vulnerable and transparent with my wife.  Not only as Hannah, but as in my male side as well.  This took a lot of patience on her part and a lot of effort to try to understand me.  It took a lot of time, sometimes difficult communication and open and honest conversations.

So yes, she has seen Hannah.  We both met her at the same time, in a way.  We’ve had many girls nights in, whether it was a nice quiet night in wearing leggings or me rocking an amazing gown with winged eyeliner.

My wife and I used to feel that Hannah and my male side were two very different people.  Of course, we have very different wardrobes but over time Hannah and I have kind of… well, balanced out.  Hannah would tend to be more relaxed and chatty whereas I was more preoccupied with whatever was going on or needed to be done.  I don’t relax much, but our girls nights in gave me a chance to dress up and slow down and watch a movie or sit and talk.  My wife and I don’t feel there’s as much of a difference between my two genders (besides physician appearance and presentation) as there used to be.

I make all of this sound very easy and idyllic, but as with any relationship things are always more complicated and nuanced than it sounds.  I am lucky to have my wife for many reasons, not only because of this.

Love, Hannah