Review: Lara Underbust Corset

If you’ve spent more than a minute on my website you will likely realize a few things:

-I heart clothes

-I overthink

-I overthink about clothes

I tend to associate a lot of memories, meanings, and emotions with a particular piece of clothes. Well, femme clothes. I have a lot of neckties that I absolutely have no idea where they came from. On the other hand I have an incredibly beautiful floor length ball gown which fit perfectly before I lost weight that I will never ever get rid of because it was one of the first dresses my wife bought for me.

I am enamored with certain items because of their beauty, even if they aren’t, well, practical. My six inch rose gold platform stilettos? I’ve worn them like twice but my goodness they are magnificent and will forever have a permanent spot in my closet.

Lingerie is a perfect example of pragmatism versus beauty. Tights are more practical than thigh high stockings held by a garter belt, but I chose stockings almost every time.

For years a corset was a perfect example of something that was visually stunning but not something I felt could be worn for long periods of time. But that was because I was wearing them wrong and I didn’t have a proper corset. My introduction to proper corsetry started with my Dita Black Satin Corset from Glamorous Corset.

It’s a stunning piece of lingerie and my goodness did I learn quickly that it required proper training as well as commitment. I had never heard of seasoning a corset before but I learned. Corsetry requires an insane amount of dedication and at first it was kind of intimidating but I quickly realized the benefits of following through.

While preparing for a photo shoot over a year ago I decided to wear my corset which I rarely did for long periods of time. This would be the first time I would wear it for more than several hours and it would be the first time I would wear it outside of my home when I would be getting in and out of a car, going up and down stairs, and doing a lot of walking. Again, it was intimidating and there was a learning curve but it didn’t take long to see the benefits of a proper corset and the results of the hours I put in seasoning it.

Since then I have worn my corset every time I present en femme. Yes, it’s a stunning corset but its equaled by the practical benefits of it. A perfect balance.

I was thrilled when I was contacted by Glamorous Corset asking if I would like to review their Lara Black Cotton Corset with Hip Ties corset. Yes please!

A corset takes dedication and it also requires accuracy. Measurements are absolutely key.

I sent in my measurements and within a few days I received a black velvet bag with the Lara corset in it.

Although I’ve been wearing my first corset for a while and I am very much used to it, I was still taken aback by the beauty of it not only in terms of appearance but also in construction and design of it. I love small, subtle attention to clothes, whether it is a small fabric rose on the front of a pair of panties, and in this case of the Lara I was drawn to the side ties of it. This is a steel boned corset which helps create a more defined (curvier) figure and helps with my posture. I couldn’t slouch if I wanted to.

My second impression? Yes this is beautiful but I have a certain affinity for my current corset and I couldn’t imagine wearing the new one in place of it. This thinking would change.

I spent about a week seasoning it and was quickly reminded that although I am used to A corset it doesn’t mean I am used to ALL corsets. When seasoning one you should wear it for about an hour at first and over time wear it a little longer as you progressively adjust the lacing. A quick reminder if what you’re wearing hurts (be it a gaff or a corset) you’re wearing it wrong. I wear my current corset for up to 14 hours at a time and I naively thought this new one wasn’t going to be as much of a learning curve as it was.

After thirty minutes or so I was very much aware of what I was wearing. It was a relief to take it off however over the next few days as it adjusted to my body it became more and more comfortable and by the end of the week I was wearing it for up to ten hours (in boy mode).

This was one of the items I wore for my most recent photo shoot and although one of my first thoughts was that I would continue to wear my Dita corset I realized that my Lara would now be my go-to corset.

Photo shoots can require a lot of creative movement and posing. This could be reclining or balancing on one stiletto. The Lara moved with me and complimented my figure with every gesture. The seasoning and expert design of it paid off.

I was a LITTLE concerned about stealthing (essentially subtly wearing a corset in public) but this wasn’t an issue as shown in the photo below.

This is a stunning corset. It marries beauty and practicality. It demands commitment. And isn’t that what this side of us is all about?

Love, Hannah

Let’s Talk About Money

Crossdressing takes time, patience, and money.

And Lord knows I have invested a LOT into who I am. It costs a LOT to look like how I look. I like to think (perhaps naively so) that HE and SHE look very different from each other. If Hannah is going out on Saturday morning, HE looks into the mirror on Friday night and wonders just how in the world THIS is going to work.

At the end of the week HE has worked close to fifty hours, has had a lot of meetings, and hasn’t gotten enough rest or enough coffee. His face is tired, he has bags under his eyes, he needs a shave.

And by what is seemingly magic, HE is replaced by HER the next morning.

But there was no fairy godmother involved, just a really good foundation and expensive clothes which made it happen.

When I get asked how to crossdress, or how to present en femme, I try to be realistic about how much time and patience *this* can take. This information is usually easier to process and accept than when we start looking into the financial aspect of it.

A bra costs HOW much?

Lipstick is HOW much?

I spent $18 on stockings and one snagged after only an hour?

This $190 wig looked cute online but I HATE it

These things can be jarring, especially when we aren’t accustomed to shopping for these items.

And for me, there’s a LOT of items. This can consist of a pair of clip-on earrings that I bought on Amazon for $15 or a hundred dollar dress. And then there’s everything in-between. And everything UNDER the dress.

So, let’s break it down.

Well, BEFORE we break it down, I want to stress that none of this is necessary to be feminine. You don’t NEED to do ANY of this to be who you are. You don’t need to get a second job if to afford to be a girl or to crossdress. You are a girl if you identify as one, you don’t need to have a specific figure or body size or body parts or to wear certain clothes. A girl can be tall or wear a size 14 heel. A girl doesn’t have to wear a dress to be feminine. You are crossdressing with a pair of panties that cost a couple of dollars.

This breakdown is what I have invested (financially and over time) in how I look, how I dress, how I present.

Here we go!

I am not an accountant so my math is probably a little off but this outfit, this look, this… EVERYTHING cost about ten thousand dollars.

Well, not really.

What’s not reflected in this is the amount I have invested in clothes that didn’t fit, the hours on the Stairmaster to tone my legs, wigs I purchased but weren’t right for me, the makeup lessons I’ve paid for, and other things over the last ten years.

If you were to see me on Friday night compared to Hannah on a Saturday morning, I don’t feel you would think that HE has the potential to look like HER. HE is not gifted with a feminine frame, clear skin, or a (somewhat) hourglass figure. He is in his mid-forties, he is tired. It’s true that HE is the foundation that Hannah is built on, but what he has and what he is, well, it’s not enough. My corset gets tightly cinched, my face gets an expensive makeover, silicone breast forms are tucked into a bra, pads on my hips, the right wig on my head, and clothes that are (hopefully) flattering.

HE is not pretty. But HE invested a LOT of money into looking how Hannah looks.

And my God, I know I invest a lot of money into all of this, but to see it… ah, itemized like this is a little eye-opening.

But this is reality. I mean, it doesn’t HAVE to be. None of this is really necessary for someone to be a girl or to a crossdress. The point of this post is to address a question I am often asked: “How do I look like you?”

Again the answer is time, patience, and money.

Listen.

No matter how much money I invest and how patient I am as time passes, I will never look like the beautiful t-girls that I admire. I look like ME. You won’t look like me, either. You will look like YOU. And you are beautiful.

Love, Hannah

Ask Hannah!

I read your article on corsets and was wondering how to go about purchasing one. Not sure if I want a corset or a waist cincher.

Like a lot of clothes and heels that we shop for, we need to purchase what FITS, not what we WANT to fit. I would love to be a size 8 stiletto but no matter what it’s 11.5 for me.

Corsets are very much the same. Of all the items you can add to your closet, corsets are the trickiest. This is where measurements are key. I might be a size 12 in a dress and a size 8 in a skirt, but this means absolutely nothing when it comes to a corset or a waist cincher. Yes, I might WANT a 24 inch waist and a corset will help with reducing my waist size, but I don’t think there’s a corset on the planet that could do reduce my waist that much without damaging my organs. Corsets are not to be be messed with.

Get your measuring tape out and order accordingly. Glamorous Corset has a very helpful guide when it comes to how and what to measure for with different body types.

I have two corsets from Glamorous Corset and before I ordered each one I took my measurements and then contacted them with my sizes and asked for a recommendation. I disclosed I was a transgirl and had a “boy” body. They suggested a style and a size after seasoning them both corsets are a perfect fit and I can’t imagine presenting en femme without them.

It does take a little work to find the right size and style, but remember, *this* side of us takes time, patience, and money. Spending twenty dollars on a skirt that may or may not fit is one thing. A quality corset is a little more of an investment. You can likely return a dress that doesn’t fit, but probably not a corset.

Have fun!

Love, Hannah

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


Let’s Talk About Catfishing

Like many terms in our little world, such as “passing”, “being read” and “clocking”, catfishing means something other than what you’d think it would.

‘Catfishing’, or ‘fishing’, is used a lot more broadly than it used to. According to Urban Dictionary, it’s defined as the phenomenon of internet predators that fabricate online identities and entire social circles to trick people into emotional/romantic relationships (over a long period of time).

But for a while it was used to describe a t-girl who really, ah, enjoyed “tricking” cisgender heterosexual men into them thinking they were a cisgender girl. Usually the reveal occurred during an intimate moment, if you know what I mean.

I’ve always hated this. And here’s why!

First of all, there’s no such thing as what a girl should look like, whether she is transgender or cisgender. Girls can be tall or have a penis or need to shave their face. Catfishing typically involves a t-girl looking SO FEMININE that men are duped into thinking that she is a cisgender girl. Look, I understand and can relate to wanting to dress and present as feminine as someone possibly can. I attempt this with every outfit I wear and with every makeover I get. But I do what I do and wear what I wear because this is how I want to look and how I want to dress. I don’t think any of us needs to meet certain standards to be feminine, to be a girl, to be pretty.

Secondly, intentionally deceiving people is not a good look for the trans community. Some haters like to think that transwomen are trying to deceive men into thinking they are cisgender. And to be fair, that’s kind of what catfishing is. But I don’t think most transwomen are trying to deceive anyone.

This is also potentially very dangerous for someone to do. When we come out to someone we never really know how they will react. Someone learning that the cute girl they are in bed with has a penis could turn violent. There are too many stories of men getting angry when they learn that they are talking with a transwoman when they believed they were speaking with a cisgender girl. In situations like this it’s not uncommon for someone to use the “gay panic defense”. Citing Wikipedia, this is when a defendant claims to have acted in a state of violent, temporary insanity, committing assault or murder, because of unwanted same-sex sexual advances, typically from men. A defendant may allege to have found the same-sex sexual advances so offensive or frightening that they were provoked into reacting, were acting in self-defense, were of diminished capacity, or were temporarily insane, and that this circumstance is exculpatory or mitigating.

Again, I absolutely understand and can relate to wanting to look as femme as possible. But how I present is 1000000% about ME. I don’t dress for anyone else. I don’t dress to pass or to blend in. I don’t care if anyone “knows” I am transgender and it’s not a compliment if someone thinks that I am cisgender.

Finally, catfishing has an element of competition to it as well. Some t-girls and crossdressers who catfish sometimes gloat about how successful they are in tricking men and can criticize others for not looking “fishy” enough. Can we stop doing this? Can we stop competing with each other? Can we stop bringing others down?

We’re all in this together. We always have been, and we will always need to be, now more than ever.

Stay safe, stay pretty, support each other.

Love, Hannah

Ask Hannah!

Hi Hannah. I’ve been following your blog for a long time and was asking for advice. I identify as a transgender woman. I was wondering how you came out to your family that you are transgender. I could really use the advice.

I’ve come out to maaaaaybe a dozen people in my life. Siblings, a parent, friends, girlfriends, and a roommate. Every time I’ve come out to someone it’s been a very different conversation from person to person. I have and have had different relationships and different dynamics with each person. I’ve come out to people for different reasons and there’s never been, not there ever will be, a conversation that works for every person in your life.

I came out to two different girlfriends because they HAD to know. I came out to a roommate in case she wondered why there was a nightgown hanging in the bathroom we shared. Both of these conversations were very different. Coming out to my girlfriend was complicated, my roommate? Not so much. She was very accepting and really didn’t care what I wore, just as long as I paid my share of the rent. I didn’t come out to every roommate I’ve ever had, but at the time I was just… tired of hiding this side of myself and I wanted to be able to wear what I wanted to in my own home.

My gender identity, like every non-cisgender person on the planet, has been a journey. I learn more about myself all the time and this was especially true in my youth. In grade school I was a boy who wore girl clothes. In junior high I learned the word ‘crossdresser’ and identified as such. In college I learned the term ‘transgender’ but it would be about twenty years before I identified as such. A few years ago I felt, and still feel, that ‘bi-gender’ is the six-inch patent black stiletto that fits best.

As I mentioned, every person I’ve had The Talk with has been different. But the commonality is that when I came out I came out as a crossdresser, not as someone who is transgender. These conversations were, if I want to oversimplify it, me revealing that I was a boy who wore girl clothes. These talks were alllll about clothes and nothing to do with gender identity. It was about what I DID and what I WORE and not about who I AM. If that makes sense.

I came out to my mom and siblings as a crossdresser about ten years ago. If I had that conversation today I would come out as transgender. Although I consider a crossdresser as someone who is indeed transgender, I’ve never come out in real life as a t-girl.

Essentially I have ZERO experience in coming out as transgender, ironically.

When someone is preparing to come out, there are a few things I would recommend keeping in mind:

Every person you come out to will react differently. If they respond positively and supportive it doesn’t mean the next person you go out to will react the same way… the opposite is also true.

Every time you come to someone, no matter how many times you do so, will be a new and different conversation.

Prepare for the worst.

Be gentle. This conversation will likely forever change your relationship with them and will, in a sense, rock their world.

Don’t come out if you feel it will be unsafe. If you are living at home and you think there’s a chance your parent will, well, react badly and you think you may find yourself thrown out of your home or that your life will be a living hell, then coming out MIGHT not be a good idea. If this is your situation, rest assured it will get better in time.

Talk to a gender therapist or if you are a student, a school counselor if you feel it is safe. Some states require school counselors to report to the parents of a student that comes out to them as anything other than cisgender or heterosexual. Know your state’s laws.

Don’t get your hopes up. This, of all the advice I’ve ever given, is what I wish I had kept in check for me personally. I love my sisters and I wanted nothing more for them to see Hannah as their sister. I dreamed of days shopping and getting a coffee with them but that hasn’t happened, annnnnd it probably won’t. My sisters are fine people and are supportive of the LGBTQIA+ community, but it can take some… getting used to when a family member comes out.

Know WHO you are, as best as you can. When I came out (again, as a crossdresser) I was asked a lot of the same questions from everyone I came out to. I imagine I would be asked the same questions if I were to come out as transgender. Be prepared for the normal questions about sexual identity and transitioning. It’s okay if you don’t know the answers to questions like these, but be prepared for them.

I hope this is helpful. There’s no roadmap to coming out but you can prepare.

Be safe and good luck.

Love, Hannah

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

The Ledge

So I have stepped back from the ledge.

A little.

Disclaimer: Don’t try this at home. Standing on a window ledge in heels is… not smart

Recently I wrote about how things seem to be going backwards and I do my best to avoid…ranting on my website. When I post I try to have engaging, relevant content, even when I am being totally superficial and raving about lingerie.

After I posted that particular update I calmed down a bit. Writing can be very cathartic. I read your emails which were very supportive and encouraging and empathetic. Of course some were along the lines of “Shut Up and Sing” but that was to be expected. My perspective is still very much the same and I am still angry and scared but I’ve decided a few things.

I know that my feelings and thinking may be pessimistic and perhaps not the same as everyone reading this, but it’s hard to be optimistic when legislation is being written and being passed into law that can and will negatively and dangerously impact our lives. And yes, this perspective may come off as fatalistic to some but I still can’t shake it.

Gender affirming care is being made a felony in certain parts of the United States and for now most of them are focused on people under the 18 years of age but it’s not hard to see where this is (probably) heading.

Could presenting as a gender that is different from the one you were assigned at birth be made a felony? I think that is very possible. I hope I am wrong.

I feel that time is running out. I feel that the things I do, the clothes I wear, the pronouns I use, could all be prohibited in a few years because the ‘M’ box is checked on my birth certificate. Again, I hope I am wrong.

So, knowing this, and with feeling these things, what do I do?

As I mentioned, I have stepped back from the ledge and it’s time to reassess. What do I do? What can be done?

I will continue to vote against people that have different values than I do. But other than that, I think I need to do what I would like to do, while I still can.

Not long ago I wrote about looking forward to the years ahead. It’s funny (and depressing) how the excitement of that post has been replaced with fear. It’s… like a deadline approaching, or the Sword of Damocles.

Over the last few months I have been thinking about what would be the safest thing to do if, for lack of a better phrase, identifying as transgender was considered illeagal.

And yes I know this sounds extreme. But in a country were you can earn a reward for reporting people who were involved in an abortion, even if it’s just the unknowing Uber driver, then I don’t think it’s that far-fetched for someone to be given money if they report a trans person at the mall.

Some of the potential actions are disbanding the MN T-Girls or no longer stepping out en femme. Hopefully it won’t come to these things.

For now, I am “safe”, or as safe as it is to be trans in Minnesota but things could change.

It’s best to prepare for the future even if planning is not my character, at least not in my femme identity. But let’s do some (pessimistic) speculating.

Before I dive into ANYTHING, I’d like to remind ya’ll that I am not a Democrat. I think the Democratic party, despite their best intentions, are incompetent and clueless. They’ve earned no praise, recognition, or votes.

And! I’d like point out a few facts:

The “Don’t Say Gay” legislation in Florida was proposed by Republicans.

The horrifying legislation in Texas was proposed by Republicans.

The military transgender ban from 2017 was proposed by Republicans.

This little disclaimer is about the facts about these proposals, as well as who in the government is writing and supporting laws like these. My point is that it seems that all the recent legislation that impacts the LGBTQIA+ community in a negative way has all been proposed and supported by Republicans (and yes, not all Republicans).

Anyway, as of this writing the Democrats control the White House, the Senate, and the House. If the Democrats REALLY wanted to do what they said they’d do when they campaigned, whether it was student loan forgiveness or protecting someone’s health care, they could have done it by now but I don’t think they know HOW to do what they said they would do.

It’s looking like the Democrats will lose the Senate in November’s mid-terms, and possibly the House. I don’t think there’s a single Democrat in the country that has a chance of winning the White House in 2024.

My thinking is that in a little more than two years all three branches of our government will likely be controlled by Republicans. If the last few years and the recent pieces of legislation have taught us anything, it’s that I think it’s safe to say that more laws against the trans community are a given. Oh sure, they will be written under the guise of something else, like preserving the sanctity of gender or whatever, but the intentions will be clear.

If this happens, and I think it’s likely, then my thought is that I have about two years of being able to “safely” present en femme and identify as transgender. After that, it could be a very different world.

So, what do I do until then? And yes, I know this all sounds very fatalistic and pessimistic and I hope I am wrong with all of this, but if there’s something I want to do en femme, it’s time to it now. Although this feeling of time running out is very depressing and frightening, there is a little bit of… hm, ambition I am feeling at the moment. Do I want to fly pretty? Do it now. Do I want to dress up as a princess? Do it now. Do I want to do a bridal photo shoot? Do it now. Attend a transgender conference? Do it now.

I am excited about doing these things, even if they are due to a very horrible reason.

I’ve swung back and forth recently about I should be doing. Part of me feels I need to…hm, reduce my visibility a bit to prepare for what I feel is the inevitable need to “go back into the closet” if legislation is passed to “regulate” gender identity/gender presentation. The other part of me feels that I should be as, ah, LOUD and as out there as I can possibly be before I no longer have the freedom to present and identify how I wish. Both options are extreme and at the opposite ends of the spectrum.

Stay safe. Stay true to yourself.

Love, Hannah

The comments section has gone completely off the rails and I have disabled them for this post.

Girly Mags

My late teens were explosive in terms of gender identity.

This very formative part of my life coincided with discovering designers like Xdress which was a huge moment for me. The idea that there were designers who knew that boys wanted to wear cute panties and made lingerie for people like myself was earth-shattering. I remember going through their very glossy Victoria’s Secret-like catalog with pages of pretty lingerie designed for MY body.

It was like… crossdressing was going mainstream. Like listening to your favorite band, a band that you thought only you knew of, getting played on the radio. It was like that maybe, just MAYBE crossdressing was “okay” and maybe, just MAYBE it was acceptable.

Oh, the naivety of youth.

Oh, the optimism of youth.

I still remember the first cute cami and matching panty set I ordered from Xdress. It was the first lingerie I wore that was designed for my body.

Without hyperbole, Xdress was a significant moment for me. It was around this time when an another huge moment occurred when I saw an advertisement in the back of Rolling Stone for a magazine called ‘Transformation‘. It was a small black and white ad and pretty much the only thing I learned is that it was a magazine about crossdressing.

Another earth-shattering moment. There was a magazine, an entire MAGAZINE for people like me.

(Of course, it was years later when I learned that Xdress wasn’t the first designer to make lingerie for people like myself and that Transformation wasn’t the first publication about crossdressing, but as far as I knew they were indeed the first and only.)

I called a few bookstores in Minneapolis that carried a lot of LGBTQIA+ literature (anyone in the Twin Cities remember A Brother’s Touch??) but was finally able to track down an issue of Transformation.

Aaaand I couldn’t help but feeling letdown.

The magazine was filled with advertisements for questionable estrogen pills and had layouts of very pornographic photos. It wasn’t primarily a pornographic magazine mind you, it did have articles about crossdressing that didn’t always focus on the fetishistic side of all of *this*.

I suppose I had different expectations of something along the lines of Cosmopolitan or something. I thought it would be articles about those who crossdressed, photos of clothes, fashion advice… you know, the kind of things in a lifestyle magazine.

Discovering this magazine was also around the time when I first searched online for the term ‘crossdressing’ and quickly learned that there was a huuuuge kinky aspect to people like myself. Transformation really, really highlighted this aspect.

And please know, I am not trying to be a bitch to the writers and editors of the magazine. The publishing world is not easy and getting even just one issue out is an achievement in itself. I’m sure the magazine had its audience and target demographic and likely some success but this magazine wasn’t for me.

And that’s okay! Not everything is for ME. Not everything is MEANT to be for me. I’m sure this magazine was absolutely a godsend for many people who lived outside the gender binary.

Fast forward a few years I found Girl Talk magazine (not to be confused with a magazine from the UK with the same name). THIS was the magazine I had hoped to find. It was very high quality in terms of photo spreads, absolutely beautiful t-girls, interviews and featured clothes and was just… perfect. Unfortunately the magazine had a very short publication life. But goodness that star shone bright when it did.

Frock, a digital magazine from the UK, was also very well written. I was fortunate to have written for Frock when it was still being published. The editors and staff couldn’t have been kinder. I miss Frock. Tapestry was published for over twenty years with over one hundred issues and was very much ahead of its time.

There will never be a shortage of magazines that sexualize us but if that’s not your thing, we do currently have Transliving, also published out of the UK. This magazine is available in print as well as in digital form. This publication is the highest quality transgender related magazine I have ever seen. High quality printing, beautiful t-girls, and just a really positive vibe cover-to-cover.

There are a few magazines that are written for the LGBTQIA+ community. It’s important and empowering to have representation for those who aren’t cisgender or heterosexual. I do daydream a lot about my femme life and most of my fantasies are about photo shoots or things I want to do en femme. From time to time I am inspired to launch a magazine but even I know that is too ambitious considering everything I have going on.

I know there are probably many other trans related magazines out there, but are there any that I’ve overlooked?

Love, Hannah

Ask Hannah!

i want to learn how to be a woman

I get this Ask Hannah! question, is, or variations of it, from time to time (well, ALL the time).

And to be honest I have no idea how to answer them.

Essentially it comes to what you feel you need to do in order for your whole BEING to align with your gender identity.

For some of us, we NEED a vagina to be a woman. For some of us, we need to LEGALLY be a woman. For some of us our legal status or our anatomy have nothing to do with our gender identity.

If you feel your gender identity is different than the one you were assigned to at birth, then your magical journey of hard work and dysphoria will begin. It is up to YOU to decide what your gender identity means to you and what you feel needs to be done in order for you to be at peace with your gender.

Depending on the steps you feel you need to take, you may need to schedule an appointment with your doctor and/or a therapist specializing in gender.

Love, Hannah

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

Truth or Dare

Crossdressing is sometimes portrayed as a challenge.

No, this isn’t about the challenge of trying to find the right foundation to cover up our stupid facial hair, this is about the… crossdressing DARES that we see online from time to time.

Do you know what I’m talking about? They seem to be mostly aimed at the “crossdressing is a kink” crossdresser (not that there is anything wrong with that).

These challenges are usually broken down into steps with the first “challenge” being something rather small and progressively becoming more advanced and tend to push people out of their comfort zone.

Not that this is a bad thing. This is EXACTLY what building up the courage to go out en femme requires. Baby steps. If they are thoughtful and well written, they can be immensely helpful when it comes to providing… ah, step-by-step guidance as to what you do first, what comes next, and so on.

These challenges almost always concentrating on what I call the practical side of crossdressing, such as focusing on clothes and heels and makeup. Which can be important! I think they are! However, they usually skip over the emotional and psychological aspects that crossdressing and presenting en femme usually requires.

What I mean is that it’s easy to find a wig, but often the wrong wig can trigger dysphoria. There are countless dresses that will fit us, but if we don’t like how we look in them it can be hard to feel that yes, we CAN be, and that we ARE beautiful. We can follow along with a makeup tutorial on Youtube, but if the products used aren’t right for our face shape or skin type we probably won’t look like the supermodel that we were expecting.

These disappointments can trigger a lot of negative feelings and frustrations and hopelessness.

In a lot of ways the practical sides to crossdressing are a zillion times easier than the psychological parts. Essentially a dress can fit, the heels can be comfortable, but if we don’t FEEL cute, if we FEEL we look “too male”, the clothes don’t matter at all.

Does that make sense? I hope so because I don’t know how to explain it differently.

Sometimes the challenges are a “point system” where you award yourself points for the different tasks you complete. Once the points are added up you can find out how much of a sissy you are, or whatever. Again, these tend to be mostly kinky in nature with wearing panties is worth one point but dressing up in teeny-tiny schoolgirl skirt while having anonymous sex with a stranger in the backseat of his 1993 Honda is worth ten points or something.

It’s sometimes jarring at how quickly the sexual nature of these challenges can escalate. The first challenge is tiny and innocent, but then all of a sudden you are getting dared to put on a frilly pink French Maid dress and having a gangbang at a truck stop.

I tended to score very low on these. And I have nooooo problem with that.

Like other things out there, these lists can be fun but also play up the sexual aspect of crossdressing. Again, there’s not anything wrong with that. But many of us dress how we do for so many reasons and kinkiness isn’t even relevant. There’s the fantasy aspect of this for some of us but for some this isn’t our truth.

From time to time I think about writing my own version of something like this, but I think the “challenges” would be, well, not fun. It’s easy to dare someone to buy a cute bra, it’s another thing to actually do it. Buying a bra is not as easy as it sounds, even if you’ve been wearing one for years. Cup size and band size are too be considered, and there are different bras for different outfits and different bodies and different, well, GOALS, I suppose.

But I suppose this is how ANYTHING is. Telling someone how to change a tire SOUNDS easy but, well, it’s NOT. Everything is easier said than done.

I am also hesitant to write something like along the lines of “instructions” because we all have different goals when it comes to this side of us. When someone asks me “how do I crossdress?”, I struggle with how to respond because, well, crossdressing could be as simple as painting your nails or as time-consuming and expensive as hair removal, breast forms, thigh pads, a $90 makeover, an expensive wig, and a killer dress with matching heels. It’s kind of up to you.

And! Step-by-step doesn’t always work for each of us. Our journeys are not linear or identical to everyone else (which is a tiny reminder that we shouldn’t measure our progress or self-worth in comparison to anyone).

I know I often sound like a wet blanket when it comes to crossdressing. I focus a lot on the reality of this side of us which can be a buzzkill. But please know that I absolutely understand that expressing our femme identity or wearing what we want (for any reason) is important AND I think it is really super fun. Yes, it’s a lot of physical work to shave and wiggle into a dress and cinch my corset and strut all day in stilettos, but it’s SO MUCH FUN. I love it. I love every minute of spending the day en femme. I love getting ready. I love shopping for clothes and wearing new panties for the first time. The magic is always there.

I suppose these challenges and the idea of awarding points is similar to thinking about what we SHOULD be, what we SHOULD look like, and so on. It’s easy to look at a list like these and feel that we are not femme or brave enough if we’ve only done half of the “challenges” and the rest feels intimidating.

Sometimes these “challenges” include something along the lines of “tricking” a guy at a bar that you are a “real” girl. UGH. So many things are wrong with that. There’s no such thing as a “real” girl. I KNOW that this is referring to “fooling” someone that they are a cis gender girl but girls are girls, trans or not. And! you don’t need validation from some loser drinking beer at some stupid bar. A guy being attracted to me isn’t a victory, in my opinion. It’s not the compliment that we are led to believe.

Listen. This side of us is super fun and amazing but it’s also some of the most difficult parts of our lives, especially on the emotional side of who we are. We don’t need to make it any harder by measuring our progress and what we do or what we wear against some silly list or by comparing ourselves with anyone else.

And yes, like changing a tire, this is easier said than done. Sometimes I feel cute but then I feel absolutely monstrous in comparison when I see photos of Heidi Phox or Farrah Moan.

On the flip side I do feel like a supermodel when I look at a recent photo of myself and compare it to a picture from a few years ago.

But maybe that’s the point?? Maybe we need to focus on our own personal growth and be happy with any progress we make, no matter how small or how long it takes.

Love, Hannah