What’s So Funny About Peace, Love, and Underdressing?

Most of us discover this part of ourselves early in our lives. Like, EARLY in our lives, usually in childhood. I think most of who we are as adults is formed in that time. I mean, they are called our formative years for a reason, right?

When I was a child I didn’t think I was doing anything *wrong* by trying on every dress I could find. I never thought I was *bad* for wanting to wear the beautiful lingerie I saw on department store mannequins. Despite this, I knew, and I am not sure why, I had to keep this side of myself a secret.

It’s possible I felt that it needed to be a secret because I was borrowing my sisters’ clothes without permission and that in itself was wrong, not because I was a BOY that wanted to wear a dress, if you follow.

I was blissfully unaware that there was anything taboo about who I was or what I wore. I mean, of course I didn’t tell my friends that I wanted to wear what the girls in our class were wearing, but I think that had a lot to do with assimilation. It’s not uncommon for kids wanting to fit in and to do and say and be interested in the things that the “cool kids” were into. The popular boys in school weren’t talking about pretty clothes, so I didn’t either.

As my childhood progressed (and I am talking about being around 7 and 8 years old) I started to connect the dots about this side of me in terms of how the world thought of someone like myself. These revelations further reinforced the need, almost a survival method, of keeping this side of myself a closely guarded secret.

When I was in my late teens I learned that “crossdressing is a fetish” was seemingly the prevailing perspective. But until then, I was taught that a boy who wore girl clothes was HILARIOUS.

I mean, I was also taught that it was shameful and in a way a punishment but those are things for another day. Instead, let’s chat about how HILARIOUS crossdressing is and was portrayed.

Why is this funny?

I mean, it’s not. It never was. A lot has changed since I was six years old. I wouldn’t say we are more enlightened these days when it comes to gender not being a binary but we’re slooooowly getting there. It’s like walking to the sun.

If someone saw a boy wearing a dress forty years ago they would have been mocked and punished. A boy wearing a dress today, well, there is a very good chance they will still be mocked and punished but there will be those who understand the complexities and simplicity of gender identity.

It wasn’t uncommon for cartoons and movies to have “comedic” moments showing a man wearing a dress or lingerie. It was and still is a cheap joke and the writers probably weren’t too interested in gender identity awareness. I mean, look at how racist and sexist cartoons used to be. Cartoons with characters in blackface or mocking women drivers were pretty normal for a long time.

I don’t really remember exactly the first time I saw a someone even remotely similar to me when I was growing up but I know for certain we weren’t represented in a way that I was, well, proud to be associated with. If a character was shown in their underwear it was probably meant to be funny. Most kids watching a cartoon would probably think it was.

But if the character was wearing pink panties instead of, oh, I don’t know, polka-dot boxers? Peak comedy right there.

We were told that a boy wearing pink panties was meant to be funny. So, we learned that a boy wearing pink panties WAS funny.

Again, these years are called our formative years for a reason. But not everything we learn or are taught is right.

A boy wearing pink panties is funny for the sole reason we were taught that it’s funny.

Was this done maliciously? I don’t know. It’s impossible to say. Like a lot of things in entertainment, certain elements are duplicated if they are successful. If one type of movie makes a billion dollars it won’t take long for similar films to be made. If a joke about a boy wearing pink panties gets a laugh… you get where I’m going with this.

How did this start? Oh, I have no idea. But my guess is that this is rooted in the thinking that anything feminine is shameful and embarrassing.

The cartoons I watched when I was very young showed women as bossy or unintelligent or lazy or emotional or bimbos or lazy. Women were fodder for comedy. The entertainment industry was (and still is) predominately white, cisgender men and how women were written is and was influenced by that.

I mentioned early cartoons mocking women drivers but this type of humor was the rule, the norm. Wilma Flintstone was a gossipy housewife who yelled at her husband. Jane Jetson spent all of her husband’s money on clothes.

Mocking women was “funny”. It probably didn’t take too long for some writer to think it was hilarious to attribute feminine traits to male characters with the intention of mocking them. A female character cooking was “normal”. A male character cooking was shameful and an easy way to ridicule him.. and he was probably wearing a frilly pink apron.

Thus began the dangerous and harmful perception that feminine = shame and humor.

Well, not really. The “tradition” of male actors and male characters playing women for laughs goes back centuries all around the world. Essentially this humor has been around for a very long time. Is it any wonder that reversing the perception that crossdressing ISN’T funny/kinky is unlikely going to happen? We’ve got centuries against us.

As I said earlier I didn’t think what I was wearing was shameful but it needed to be a secret. But I never thought that it was HILARIOUS. I knew if I was “caught” I would be ostracized from my friend group. The reason for this was not because of the clothes per se, but because at certain points in your life if you wanted to fit in, if you wanted friends, you had to like the same things, you had to think the same way, you had to enjoy the same music and movies as everyone else. And that extended to what you wore.

But I never thought (and perhaps I was naïve) that there was anything comedic about wearing what I wore and what I daydreamed about wearing. Sure, I knew it wasn’t normal for a boy to wear a dress but the way I perceived my fashion choices was similar to that one kid you knew in third grade that liked jazz when everyone else liked Van Halen.

If that makes sense.

It was… I don’t know, it was weird when I realized that male cartoon characters wearing girl clothes was supposed to be funny.

I didn’t know why at the time this was funny or meant to be funny. I realize now that this was probably related to anything feminine was meant to be hilarious or embarrassing. Essentially anything that wasn’t traditionally masculine was intended to insult or ridicule.

How did this impact us?

It was yet another nail in the “keep this side of us a secret” coffin. As if we needed another reason.

It’s a shame this side of us was ever played for laughs. How different of a world would this be if femininity was never ridiculed?

Love, Hannah

Walking Around in Women’s Underwear

The holidays are here and the world is doing everything it can to remind us. DO YOUR SHOPPING! VISIT THE RELATIVES THAT YOU HATE! MAX OUT YOUR CREDIT CARDS!

Each year I try to use the end of year festivities as a chance to rest and recuperate. Of course that never happens. Work holiday parties and family gatherings, although can be very nice, chip away at any down time and any hibernating that we look forward to and likely need.

With Christmas Eve and Christmas day two weeks away (my God, TWO weeks away??) I am once again looking forward to slowing down a bit, even if it’s just for a couple of days. But I know it’s not going to happen. Each year Christmas and then New Year’s come barging in and then abruptly leave and I realize that no, any downtime I had looked forward to just didn’t happen.

And I think to myself, well, maybe next year. But I know it won’t happen.

….

This is starting a lot more introspective than I had planned.

Anyway, I was raised in a house where as soon as the first of December hit, the needle on the record player would drop and Christmas music was playing in the background for the next few weeks. These are some of the first songs we learn and possibly love. When we get a little older we realize that some songs (looking at you, 12 Days of Christmas) are just… stupid. We realize that just because a song is a classic, Christmas or otherwise, it doesn’t mean it’s actually good.

But in the years between childhood wonder of Christmas and the teen years of Christmas cynicism, we discover the world of parody, specifically the satire of holiday music. As kids we thought “Jingle Bells, Batman smells…” and “Joy to the world, the school burned down…” was peak comedy.

It felt rebellious, in a way.

I don’t remember when I first heard the revised lyrics of “Walking in a Winter Wonderland” in a little tune called “Walking Around in Women’s Underwear” by Bob Rivers.

Lacey things, the wife is missing.
Didn’t ask, for her permission
I’m wearing her clothes,
Her silk pantyhose.
Walking ’round in women’s underwear.

In the store, there’s a teddy.
With little straps, like spaghetti.
It holds me so tight,
Like handcuffs at night.
Walking ’round in women’s underwear

In the office there’s a guy named Melvin.
He pretends that I am Murphy Brown.
He’ll say “Are you ready?”
I’ll say, “Woah man! Lets wait until the wife is out of town.”
Later on, if you wanna,
We can dress, like Madonna.
Put on some eye shade, and join the parade.
Walking ’round in women’s underwear.

Lacey things, missing.
Didn’t ask, permission.
Wearing her clothes, silk pantyhose.
Walking ’round in women’s underwear.
Walking ’round in women’s underwear.
Walking ’round in women’s underwear……

For very obvious reasons, I was mesmerized by that song. YES, I DO want to walk ’round in women’s underwear.

I knew that the song was supposed to be hilarious and it kind of annoyed me that there was one more thing out there that portrayed this side of me for laughs, but I still loved the song.

Looking back I can see what parts of the lyrics stood out to me. “Straps like spaghetti” and “silk pantyhose” piqued my attention. Like… this song gets it. Of course, the song also discussed opportunities to dress increased when your family wasn’t home and goodness I could relate to that.

I hope Santa brings you a new negligee this year and that we all have a little time to strut (or rest) in the clothes that make us happiest, the clothes that make us whole.

Love, Hannah

Announcing the Hannah!

This side of us has dreams and desires that are wildly different than what many people in our male lives (if we have one) would ever guess.

I mean, I can’t imagine my coworkers would ever even begin to speculate that one of my life goals is to be a bridesmaid.

A while ago I realized I had a dream of, well… I mean, it sounds kind of silly but I think many of you will understand.

HommeMystere makes beautiful lingerie for girls like us. I have quite a few of their bras and panties in my wardrobe and I love wearing their matching camisole and panty sets or teddies to bed. It’s not uncommon for their designers to create a cute set with a name, such as Charlotte or Juliette.

I’m sure you can see where this going.

I thought it would be amazing to have a bra and panty set named after me.

A few months ago I received an email from HommeMystere and like magic, my dream was real.

They sent a beautiful tartan bra and panty (and a flirty little skirt) and like everything else they design, it fit perfectly. Modeling it at a recent photo shoot was an unreal experience.

I am thrilled to show you this beautiful set. I hope you like the pictures and I hope you like the lingerie.

The Hannah will be available in early 2023!


Love, Hannah

Unwrapping

It’s my birthday!

And what do we do on birthdays (besides reflecting on another year passed or dreading what is to come or having an existential crisis)? Well, if you’re lucky you can unwrap a present!

In celebration of my birthday I would like to post the last set of pictures from my most recent photo shoot. And yes! They are lingerie shots to go along with the unwrapping metaphor.

Unwrapping? Undressing? Let’s just go with it.

And yes! Not very introspective but I’m working on a lot of thoughtful entries at the moment so I am giving my brain a little break from serious thinking and just indulging in my love for pretty lingerie.

Love, Hannah

Ask Hannah!

I read your post – the one in which you feature a photo of you on a couch – and I’m curious… and how to ask this? I’m curious to know what your goal or hopes where about taking that photo. I’m wondering what brought you to that decision.

Oh, you mean this one?

I love this picture and I’ll use any excuse to post it, lol.

I don’t think I had any goals or hopes. Sometimes I intend a photo to communicate a certain emotion or feeling but it usually falls up short. I realized that if I try to express… anything it comes off as insincere or forced unless it is a truly genuine emotion.

And honestly? It usually is forced. Trying to look like a badass or whatever is the opposite of what I am actually feeling during a shoot. I love shoots. Switching it up to a serious facial expression contradicts the fun I am having.

On a similar note, trying to come off as sensual or sexy is also a little forced. Despite what the photos suggest, these shoots are not, well, erotic. Modeling lingerie (at first) was nerve-wracking. I am usually cold, lol.

The pictures I like the most are the ones where I remember feeling something very strongly. For example, this photo:

This was taken in November of 2020. We were months into the pandemic and the holidays were approaching. The optimism that we would have COVID under control by the end of the year was quickly disappearing. The likelihood that holiday gatherings were going to need to be changed or canceled were increasing. It was, well, it was sad. The year had been stressful and had taken it’s toll on all of us. We were all tired. We were all mentally and emotionally exhausted.

I remember feeling very calm when this photo was taken. I don’t know why. Probably because the afternoon of this shoot was one of the few days of the year where I could… kind of pretend the frightening events of the year weren’t really happening.

And in that letting go I felt very connected to myself. The peace of the moment came over me. I closed my eyes and just breathed.

Shannonlee took the picture.

The click of her camera brought me out of whatever trance I was in and I was back in the real world.

I like to think that this picture captures the brief calm I felt. A rare moment of peace in a tumultuous year.

The photo of me on the couch was also a moment of feeling very connected to my emotions. As time passes I feel more and more grateful for the life I have. I’ve had enough experiences in my life to know how quickly things can change. I could lose my job today. A family member could have a life-alternating injury or medical emergency. I plan for a future that may never happen.

I’ve always hated the idea of living every day like it’s your last. I mean, if I did that, and I mean if I REALLY did that I would quit my job and my wife and I would hop a plane to Italy.

Aaaand of course if I did that and it WASN’T my last day of my life I would have no job and no savings… but I would be in Italy so there’s that, I suppose.

I was feeling very beautiful on this day. The key word is FEELING. Whether or not I THINK I was beautiful or whether or not I WAS beautiful isn’t important here. I am over six feet tall, I have man feet, I have countless physical masculine characteristics. No one would see my body and think it belongs to a cis girl.

The body belongs to me. And I am grateful for it. I am grateful for my legs which allow me to walk. I am grateful for my healthy heart which allows me to exercise and stay in shape. I am grateful for my stubborn mind which keeps me sober.

On the Saturday this was taken I had escaped another stressful week at work. We all have had days that end on a note that you just know will make the next day difficult. A lingering problem, an unexpected situation that comes out of nowhere that causes worry and stress. On those rare Friday afternoons when this doesn’t happen I am grateful to enjoy a weekend without the Sword of Damocles suspended over me.

The absence of work problems, combined with a surge of gratefulness and cute lingerie came together for a really fun photo shoot. I was having a really nice afternoon and honestly? I was just in a good mood.

Many of my photos from this shoot captured me just living in the moment and responding to the camera and the studio. Who knows how much longer any of us have? Who knows what could change? It’s not always possible to do so but my God, if I can taste the strawberry I will.

I am forever getting older, I am forever slowing down. I knew I would never be this young ever again. I may never feel this confident in lingerie ever again.

I sat on the couch, did a few poses and leaned back. Shannonlee knows me well enough when to take pictures and when not to. There are always moments when I am contemplating how to position myself or thinking if a pose would be a good picture. Of course, she is an excellent photographer and will always guide me as well. I mean, after all, I REALLY have no idea what I am doing. Any picture that is halfway decent should be credited to Shannonlee’s guidance and her talent (and my makeup artist and the clothes themselves).

I laid down, crossed my leg, and turned my head. In the same moment I was living in my skin like never before but also felt separated from any fear of whether or not I looked femme. It was HIS body, HER mind. OUR heart.

…That got a little deep, didn’t it?

As long as I can remember lingerie has had an enormous impact on my life. I couldn’t stop thinking about what it would be like to wear stockings and corsets and bras and garter belts and all the wonderful, beautiful articles of clothing I saw mannequins and Victoria’s Secret models wearing.

Over time this pull never dissipated. This desire created courage. Courage led to purchasing my very own lingerie. It led to me wearing these beautiful clothes. I’m forever grateful to have gathered the bravery it took to nervously look for a bra and panty that would fit my body as I haunted the lingerie section of a store. The bravery it took to face the cashier.

It also took acceptance of who I was. I was someone who wanted to wear lingerie, no matter what body parts I had, regardless of what my birth certificate and drivers license said.

Wearing lingerie is a remembrance of the courage it took for me to be who I am. I am fortunate to have conquered any fear, any reluctance I had about my identity. I’m blessed to have overcome the thoughts and doubts that could have held me back.

Being who we are requires an enormous amount of self-love and courage. Whether you are trembling with fear as you browse the lingerie department for the first time or talking to a gender therapist or the million other things that we might do because of who we are, we should all be celebrated.

Love, Hannah

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

Beautiful Vulnerability

I absolutely believe that t-girls and non-binary people EVOLVE. I have a love/hate relationship with the term JOURNEY… it’s cliched and makes it sound the challenges and bliss that we experience are almost trivial and naïve. I suppose it’s probably one of the more appropriate terms for our lives, though.. But like a stiletto that is a half-inch too small, it doesn’t quite fit right.

Maybe evolution is a better term? I mean, we start with this longing in our heart for pretty clothes or we become aware that the gender everyone says we are isn’t quite right. As time passes and as we experience, uh, experiences we start to realize that the world is bigger than black and white… and pink and blue.

We go from wondering what it would be like to wear a dress to being conflicted by this desire… and then we go from looking at them at the store or online to plucking up the courage to buying it… sooner or later we are wearing it… perhaps in our living room with the curtains pulled… and then maybe one day we are rocking it at the mall.

Evolution, baby.

I was thinking about this as I was looking at pictures from my most recent photo shoot. A girl needs outfits for a shoot and although it sounded impossible at one point in my life I chose a little lingerie for the shoot.

Evolution, baby.

I heart lingerie and I’ve gotten past any reservation and shyness when it comes to showing off my, ah, intimate apparel (as the department stores call it). A big part of why I love lingerie shots is because of what they represent to me.

Not only are they a reflection of confidence (I mean, I think it’s pretty brave to do this) but it’s also (at least to me), the ultimate final strut of my personal journey/evolution when it comes to how I feel about my body.

Dysphoria is a bitch and over the years I have hid my shoulders or have been too terrified to leave the house because I didn’t “pass”. I went through (and still do) periods where I believed that certain parts of me were too masculine to wear ANYTHING, especially if it was a dress with thin straps.

But thankfully I have moved past that. Of all the things I’ve accomplished or will accomplish in my life, getting over the invalid thoughts that held me back will always be my biggest victory.

Someone dressed in lingerie is showing the WORLD (or just their partner) their body. Every beautiful “flaw” and every beautiful imperfection.

Complete vulnerability. Letting your guard down is intimate and courageous.

When I was growing up it was the scariest and bravest thing in the world to let my eyes linger a little tooooo long at the pretty dress the mannequin at the department store was modeling. Over time I found the courage to follow my heart when it came to beautiful clothes, especially when it comes to what we wear that only we ourselves see. Eventually I found myself (trembling all the while) wandering around the lingerie sections feeling completely giddy and overwhelmed and terrified. It felt like it took forever to take the step when it came to buying panties. And then a bra. And then stockings. And then everything else.

It was braver still to wear them, even in the quiet privacy of my own apartment. It felt like conquering a mountain the first time I underdressed outside my home or slept in a nightgown.

But I did these things. I did more than these things.

Everything about me had to evolve. How I felt about crossdressing itself to how I felt about my body to finding the courage to learn my measurements and how sizing in femme clothes worked.

But I did it! And everyone reading this evolved in some way. Whether you are wearing panties under your boy clothes or you strut out the door en femme every day or have simply and quietly acknowledged that you WANT to explore this side of you… you’ve made progress.

I hope you can relate to these words.

And I hope you like these photos!

Love, Hannah

Ask Hannah!

I recently told my wife of 16 years, about Rayne. She’s seems to be supportive, right now, and very confused, as I have been for almost 40 years, why I’m attracted to womens clothes. Nothing frilly, past that stage, I love the new styles, and I do have a desire to go in public. I was wondering, do you wear panties everyday, and who does Hannah’s laundry?

Preparing to do laundry

Hi! Yes, I underdress every day. Mostly it’s just panties but sometimes I’ll wear a matching cami as well. As for household chores, we split them pretty evenly and I usually do the majority of our laundry.

Please show your wife kindness and patience as she navigates this part of her life. These posts may be helpful to both of you.

Love, Hannah

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

I Dreamed…

When I was in college I took a design class and we studied a lot of older advertisements. It was shocking at how casual some of the ads were when it came to things like smoking and how sexist some of them were, but one series that stood out to me was the Maidenform Bra ads.

These ads showed very happy women doing random things from shopping to putting out fires all while wearing the above mentioned bra.

You can see more of these bizarre ads here.

I can only speculate what the purpose of these ads were. My guess is that the Maidenform Bra fit perfectly and you could wear one all day long and never feel uncomfortable in it.

Of course, as a crossdresser, the ads took on a different meaning for me.

I also had dreams of wearing a bra while I went about my day. Of course, I would be underdressing but still, I could wear a gorgeous bra while I did mundane, everyday things.

My daydreaming went beyond a bra, however. In time I dreamed of going to the mall en femme. I dreamed of sleeping in a nightgown. I dreamed of makeovers. I dreamed of skyscraper stilettos.

If I had known that later in my life I would have the wardrobe that I have now or would have the adventures that I do, I wouldn’t have believed it.

Some dreams come true.

Love, Hannah

It’s Like Whatever

Hi!

Guess what? I have a photo shoot booked for next month. I know, I can’t believe it either.

I have a couple of new dresses that I can’t wait to wear as well as at least one item to review.

For the item I am reviewing I was asked if I would be comfortable wearing it. After last year’s lingerie shoot I can’t imagine saying no to much anymore.

But I did recently turn down a few items that just weren’t in line with what I want to model or review as they were mainly synthetic… think feminine masks and breast plates and things along that nature. I feel that realistic synthetic vaginas are more for the fetish crossdresser (not that there’s anything wrong with that) but perhaps my perspective is wrong on this?

I started to think about how nervous I was the first time I modeled lingerie and was very glad to be done. Buuuut it was kinda fun once the shoot was over. I’ve since done a few more shoots where I’ve reviewed and modeled other items and do you know what? My attitude turned into more or less “like, whatever”. I no longer cared or felt self-conscious that I was standing in a studio wearing lingerie while Shannonlee fiddled with the settings on her camera or adjusting the lighting.

What changed? I don’t know.

Perhaps once the first set of pictures were uploaded to my website and my social media it was like I wasn’t wearing anything (or revealing anything) that people hadn’t seen already. Perhaps it was something else.

At my last shoot I was just… vibing, you know? Just standing there in my stilettos and stockings while Shannonlee set up the shot. And soon I was standing in front of a window.

I didn’t care. Maybe I should have? Regardless it’s freeing to just let go.

Love, Hannah