Ask Hannah!

Hi Hannah I would love advice on how to deal with the guilt that dressing causes discomfort for your partner. I’m married and my wife has known about my dressing the duration of our relationship. We experimented briefly but she didn’t enjoy it so I have always dressed in private. 16 yrs later, I’ve come to realize I need to explore this side of me more (I’m not transitioning, just taking my dressing beyond hiding in our bedroom). She is standing with me and we are in couples therapy. I feel so grateful I am finally getting to explore my feminine side in ways I’ve dreamed about for years … but I feel terrible my exploration is putting her in a difficult position (having to work through the associated feelings etc). Any suggestions on how to work through this?

Crossdressing and guilt seems to go hand in hand. In a lot of different ways.

Some of us feel guilt when we crossdress because we are told it’s wrong and it’s against God or societal norms and that it’s a sin. Growing up Catholic I am very familiar with how easy it is to feel guilt when I am “sinning” although I never thought God cared about what I wore. I think God, and other deity, is beyond comprehension and human imposed societal gender norms aren’t anything that God pays any attention to.

I have felt guilty when it comes to my crossdressing for different reasons at different points in my life. The first girlfriend that I came out to wasn’t that enthusiastic about her boyfriend wearing panties. She asked for assurance that I had outgrown that “phase” and I promised I would stop. I tried to NEVER DO IT AGAIN but of course we all know how quitting crossdressing goes.

I failed spectacularly at quitting crossdressing.

In this case I felt a tremendous amount of guilt when I inevitably would wear panties. I felt I was going behind her back and I was breaking my promise to her. I mean, that’s exactly what was happening. I WAS going behind her back. I DID break my promise to her.

Fast forward to where I am today and I still feel guilt but in a different way. Generally speaking I feel I am a pretty selfless person but there are times when my femme life becomes… inconvenient.

Case in point, this upcoming weekend. I have a photo shoot booked to review a couple of items and, if I am being honest, to be a little self-indulgent. Photo shoots take a lot of coordination and planning. The studio, my photographer, my makeup artist, working with designers to schedule upcoming reviews…

This particular shoot has been in the works for almost a month. Whether it’s a shoot or a MN T-Girls event I always chat with my wife to make sure that the date doesn’t conflict with her plans.

Buuuut sometimes stuff happens. As I mentioned the other day we are in the process of moving and it is looking like we are having an open house on the day of the shoot. On one hand we both need to be out of the house anyway, but while I am getting my makeup done or modeling a dress my wife will be taking care of conversations with our realtor and doing any last minute touches on the house.

I will feel a tremendous amount of guilt that day.

It’s not as simple as canceling my shoot as this would impact a lot of people.

These are two examples of feeling guilty. Some of us feel guilt when we are going behind our partner’s back. In this case guilt comes from being dishonest. So, um, stop doing that. And yes, it’s not as simple as it sounds.

And I’ve been there in previous relationships.

Some of us feel guilt when we spend more money on clothes than we probably should. This is similar to going behind our partner’s back. Our significant others may know that we bought on a new pair of stilettos buuuuut maybe we told them they cost much less than they really were.

Again, don’t do this.

I don’t feel guilty about crossdressing anymore. I don’t think I am sinning and I am certainly not going behind my wife’s back.

But I do feel guilt when this side of me takes me away from my responsibilities as a spouse such as this upcoming photo shoot.

It sounds like you are being upfront and honest with your wife and your femme side. That’s good! From what you’re saying it doesn’t sound like you have a secret life. But this side of us does put our partners through a LOT.

Our partners will likely have a lot of feelings and fears when it comes to our gender identity and our wardrobe preferences. Like anything our significant others experience we need to be patient, caring, empathetic, and good listeners.

We also need to be worth it.

Keep being honest with her, take her feelings and fears seriously, and communicate, not only in therapy but in every room in your house.

Love, Hannah

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Bless this Mess and Bless this Dress, and this Dress and this Dress and…

So! We are moving. Don’t worry, I am, and will always be a MN T-Girl but it’s time for a new house.

Life is stressful enough as it is especially now but adding preparing an entire building to look presentable to sell and trying to find a buyer and transition everything we own into a new building just adds to the AAAAAAAAAHHHHHHHHHHHHHH of everything.

Selling and buying a home has a zillion little things to do from fixing things and finding a realtor and the mortgage stuff of course but there’s also the PACKING. And for a t-girl that hearts clothes, this takes on a ginormous challenge.

Annnnd a little heartbreaking, maybe? I love opening my closet and seeing all my pretty clothes, the same clothes that I had been dreaming of for my entire life but they, along with everything else I own, had to be packed and moved into storage for a few weeks.

Last night I reluctantly opened my closet and got to work. And I knew this, you knew this, my wife knew this, but goodness I have a lot of clothes and a lot of shoes.

It took about an hour to do this and I think I could have done this quicker had I not stopped to look at almost every dress and remember the first time I wore it or what I wore it to. I don’t think of myself as a sentimental person but perhaps I am.

Of course I kept a few things unpacked such as my lingerie, outfits for next week’s photo shoot, and a few other items, but for the most part everything is boxed up.

As I took my dresses and skirts and tops and bodysuits off their hangers, I felt an enormous amount of gratitude. I feel blessed to have the life, the wife that I have. I feel fortunate that I overcame anything and everything that held me back from accepting and embracing who I am.

It’s easy to look around our home and feel overwhelmed by the mess that moving and home repairs came bring. But it’s important to take a moment to reflect on how fortunate someone can be to even own a home, own a dress, to have a life they love.

Love, Hannah

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

God Bless the Wing Girls

According to the Urban Dictionary, a wing man is a friend that you can bring to a bar or party in order to find women more easily.

This past weekend at Pride I met a few wing girls. They didn’t visit the MN T-Girls booth with the intention of romance, though. But they all had similar stories.

I have a friend who is just now accepting that they are trans and she needs to meet others like her.

These girls are not much different than a wing man. Their goal is not to help their friend hook up, though. They are helping them find support and friends.

So we chat about the group and how our mission is to be a social and support group for other transfeminine people. Sometimes the wing girl was just scouting out different booths on behalf of her friend. Sometimes she would wave her friend over who was watching shyly further away.

Girls like us need girls like us.

But I think girls like us need cis friends, too.

Besides my brother, I’ve only come out directly to cis women. I say directly because when I came out to my siblings they in turn shared my revelation with their husbands. I knew that would likely happen and I suppose I could have asked them not to out me but from my perspective if I trusted them with my gender identity then I could also trust them to treat the information as confidential.

Aaand as far as I know they have.

My point is that, for the most part (and certainly not in all cases), cis women understand (as much as they can) us.

Buuut perhaps understanding isn’t the right word. Perhaps being able to relate is more appropriate. Many cis women can relate to wanting to look cute, wanting to feel beautiful. Being drawn to a pair of shoes.

Of course, this makes women sound very shallow and superficial and I don’t mean that at all. I mean, I have guy friends who are absolute fanatics about the newest Air Jordans or whatever and sleep outside of shoe stores so they can buy them on the first day.

Sometimes my wife playfully teases me and doesn’t understand why I choose to wear a bra and high heels when I don’t have to. Expectations and standards for men tend to be very low. Society, by and large, expects women to wear certain clothes and shoes and to present themselves in a certain way.

Don’t believe me? Look at the dress code standards that some corporations have for their employees and review the differences between men and women office attire. Of course, this has evolved and gotten more progressive over the years but not by much.

My sisters don’t really “get” this side of me (and that’s fine) but they can nod their head in agreement when we discuss how expensive foundation can be. Again, they don’t understand me, but they can relate to me.

I love talking to my t-girl friends for a lot of reasons, and one of the biggest reasons is that I don’t have to explain every nuance of who I am and why I wear what I choose to. They get it. I get them.

We accept each other unconditionally. Our conversations go beyond the whys and get right to the important stuff (like dresses and makeup, lol).

I love compliments by other t-girls because they can relate to how much work presenting en femme can be. And I love compliments from cis girls. Although they may not be able to specifically relate to how much work can go into contouring a traditionally masculine face to a face that appears to be more feminine, many can relate to just how much effort goes into looking like how one wishes to present.

So, to the cis girls out there who are looking for ways to support their new girlfriend, thank you.

Love, Hannah


According to, a koan is a paradoxical anecdote or riddle, used in Zen Buddhism to demonstrate the inadequacy of logical reasoning and to provoke enlightenment.

Years ago I heard a koan that is typically titled ‘The Strawberry and the Tiger’.

Once upon a time, as a man was walking through a forest, he saw a tiger peering out at him from the underbrush. As the man turned to run, he heard the tiger spring after him to give chase.

Barely ahead of the tiger, running for his life, our hero came to the edge of a steep cliff. Clinging onto a strong vine, the man climbed over the cliff edge just as the tiger was about to pounce.

Hanging over the side of the cliff, with the hungry tiger pacing above him, the man looked down and was dismayed to see another tiger, stalking the ravine far below. Just then, a tiny mouse darted out from a crack in the cliff face above him and began to gnaw at the vine.

At that precise moment, the man noticed a patch of wild strawberries growing from a clump of earth near where he dangled. Reaching out, he plucked one. It was plump, and perfectly ripe; warmed by the sunshine.

He popped the strawberry into his mouth. It was perfectly delicious. 

This stayed with me for most of my life and I’ve often told myself in moments where I feel I am on a precipice to eat the strawberry.

What this koan means to me is that when the abyss is yawning before me, or something that cannot be stopped is in motion, that I should live in the moment, enjoy the sweet taste of a strawberry before death.

I think it’s normal to resist accepting what we fear is likely inevitable. I mean, the five stages of acceptance is a real thing, particularly when it comes to death. But this can apply itself to different moments, too. The end of a relationship, the threat of massive layoffs.

The Sword of Damocles and all that.

I always think there is an option when something wicked this way comes. While there’s life, there’s hope, after all. I tend to think quickly and I feel I can work out the logistics or a backup plan if need be.

But right now I don’t feel this.

I feel the writing is on the wall for a lot of things. Ending Roe V Wade was never the end goal. We know more is coming. The Supreme Court said it itself:

Justice Clarence Thomas argued in a concurring opinion released on Friday that the Supreme Court “should reconsider” its past rulings codifying rights to contraception access, same-sex relationships and same-sex marriage (Politico)

If these items pass, many of my friends could have their marriages nullified and the government’s intrusion into one’s personal life marches on.

You don’t have to agree with same-sex marriage to acknowledge that it’s not up to the government to decide who people choose to marry.

If the goal is to regulate contraception, then it’s not unthinkable that any sort of medical treatment for transgender people could follow.

So, you may feel I am being overly pessimistic but I can’t help but feel and fear that we are on a slippery slope towards any sort of non-binary presentation and medical care being illegal.

What does this have to do with strawberries and tigers? Glad you asked.

Over the last few months whenever I blog or tweet I feel I am being incredibly shallow and superficial. I wonder if people see my posts and are annoyed that I am writing about lingerie while tigers are circling below and snarling above us.

I know the tigers are there. I feel scared and anxious and depressed.

But I also feel helpless.

I don’t know what to do. I don’t know how to stop horrible things from happening. I don’t know how to resist, how to fight for our survival.

And yes, this sounds dramatic and fatalistic and I don’t pretend that everyone reading this will have the same perspective but this is how I feel.

This is also sounding pessimistic. Besides voting for the people I feel have the same values that I do, I don’t know what else to do. I am not a leader in the sense of rallying thousands of people together in an effort to change things. Thankfully there are others doing this.

A year ago things were stressful but even more so today. I can’t imagine what the next twelve months will bring.

All of these fears and feelings of hopelessness were weighing on me especially hard earlier this week. The tigers surround us, the vine we are clinging to is fraying. The question that kept returning to my mind was what do I do?

Like a gentle whisper, the answer came to me.

Taste the strawberry.

So, what does this mean? I will live as much as I can. I will schedule photo shoots and strut through life en femme as much as possible. I will have my head held high. I will have coffee with the T-Girls. I will live a life of quiet defiance.

I hope the vine holds. I still have enough faith that we can pull ourselves and each other to safety but until then all we have is this moment.

The strawberries that I will taste will be sweet.

Love, Hannah