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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6 thoughts on “Ask Hannah!

  1. Letting go of the guilt associated with wearing these clothes has been the focus of the therapy I’ve been doing the last five years. I initially thought I was going to therapy to deal with issues related to my marriage, parenting, my health and my anger issues. It turned out all of those issues were never going to get better until I accepted the fact that there doesn’t need to be a reason that I love these clothes and need to present myself in them. Why do I like certain foods or music or films? Does it matter? Just enjoy the unique qualities of what speaks to your soul.
    A few months after I started therapy, I started showing up dressed feminine. My therapist reinforced the importance of my own authenticity. Sometimes I presented full-on in heels and makeup, sometimes genderqueer. Soon I started making a day of it, shopping for groceries or clothes, meeting a friend for lunch. I really don’t think my wife knows I do this since I leave and return in drab. I know she gets angry when I go to a T-girl event that is public like the theatre or a museum. I’m at the point where I don’t care if she finds out. If I can’t be out on a beautiful summer’s day in a tiered smocked ruffled sundress, then I have nothing left to lose.


  2. I agree and support everything Hannah said. I also felt tremendous guilt about hurting wives (been married twice) and girlfriends. Also, tons and tons of shame. I also once swore that I would throw it all out and never ever do it again. I always assumed I needed some kind of wake-up call to get over what I thought was a compulsion.

    Thankfully my wife at the time insisted I return to therapy. I also started to explore this side of myself, but more in the direction of trying to develop an understanding of it. Was it a compulsion that could be cured?

    I spent about a year reading every book and academic article I could find and determined (for myself) that we are born with these feelings, these needs. When I started this work eight years ago I had not even heard the word ‘transgender’. I spent another year determining via lots of self-study, workbooks, therapy… that I am transgender. It’s not a choice and, like being gay, we cannot be ‘cured’ of it. It literally is what it is.

    So here’s the thing, consider the difference between guilt and shame:
    – Guilt: I did something bad, and I feel guilty. Well, for us, whatever we do to even manage our gender dysphoria isn’t bad. But of course we feel terrible about hurting others. Like Hannah, it’s all about (healthy) communication which is very hard for all parties.
    – Shame: I am bad. I felt this way for so long that it’s hard to shake. But the fact is that I am not bad. In fact, trans people are as normal as anyone else. It’s merely an adjective in a long list of other traits that define who are as a human, such as hair color, handedness, skin color, eyes, sexuality, and on and on.


  3. Hi Hannah – once again you have made an enormously helpful and actionable contribution. I should let you know that all of your readers are secretly plotting to support you in some way. I could send a jar of homegrown honey and a nice bottle or red wine from my nieces wine club

    lot’s love


    Liked by 1 person

  4. Yes – we have two committed founding members – i am thinking of re-routing my trip to Iowa to stop in Minneapolis 🙂 – lots of love bri

    ps- i have two ideas for board members


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