Ask Hannah!

Today, for the first time and with my wife being home due to Covid, I actually wore my favourite fitted bra under my t shirt which did show that I was wearing a bra. If my wife asks tomorrow if I was, shall I just tell her that I am a crossdresser or what?

I am hesitant to give advice on anything that will likely impact a marriage or any relationship.

To be clear, I am not a marriage counselor. I am not a gender therapist.

Basically, I may not know what the hell I am talking about.


Every relationship is different. Two people interact with each other in different ways compared to other relationships. There are aspects in your marriage that are unique and different than another marriage. There’s no such thing as a “one size fits all” piece of advice that works for every relationship. You know your spouse better than I do.

If your wife noticed you were wearing a bra but didn’t say anything about it it doesn’t mean approval. She may have been too shocked to say anything. She may be processing it and considering what to say. Again, you know your spouse better than I do.

Before you consider anything I write about, I will absolutely, one hundred percent encourage you to get the perspective of a therapist or of a marriage counselor. They know what they are talking about, I probably don’t.

That being said, if you still want my perspective…

Short answer is yes, probably.

Long answer is… well, it’s going to come off as preachy and perhaps bitchy, I suppose, but here goes. You can’t turn back time but you probably should have disclosed this side of you before you two were married. Our significant others need to know as much about us as possible before a real commitment is made. The conversations about whether or not you want children or an open marriage are pretty important. Conversations about religion, politics, future goals, career dreams, sexual history, sexual identity, and gender identity are also crucial.

I do not think crossdressing is a phase or something someone can stop doing. This is who someone IS.

If you are mature enough to make a decision about marriage, you probably are self-aware enough to know that this is a part of you that you won’t grow out of.

On a somewhat related note, whenever I write something along the lines of “I do not think crossdressing is a phase or something someone can stop doing” I usually get at least one email from someone that says they used to crossdress but they grew out of it and don’t do it anymore. I’m like… good for you? Also, if you’re no longer interested in crossdressing how did you find my website, a website about crossdressing?

But I digress.

My whole thing is that a) crossdressing isn’t a phase and b) we should be upfront about this side of us with our significant others.

I guess that’s two things.

So, should you tell your wife you are a crossdresser? Yes, probably.

I qualify my “yes” with a “probably” because I know that coming out is going to very likely completely impact your relationship. It’s likely going to change EVERYTHING. Your partner will likely look at you and think of you in a completely new light and they may not like this revelation.

Could they have a positive reaction to this? Yes, anything is possible but it’s not something you should expect.

Could this conversation be swept under the rug? Yes, and if that’s the case they are communicating to you that they do not want to discuss this side of you any further.

Could this revelation end your marriage? Yes. And again, this sounds bitchy and scary but this is a possibility.

It’s not always the crossdressing ITSELF that causes a relationship to erode. It’s the “why didn’t you tell me this BEFORE we got married?” as well as the perceived (and typically accurate) dishonesty that this side of us can bring. Listen: If you ever told your wife you were on a business trip but instead took a couple of days to dress in a hotel room or visit a city en femme, well, that was a lie. Suddenly the connection between lying and crossdressing is linked.

Trust is gone, or at least has taken a hit that could take years to repair (if it ever repairs at all).

Marriage (or any committed relationship) likely has shared finances whether it is the two of you owning a home or shared debt. You may have children. These are parts of a life that will be impacted by the end of the relationship and will need to be sorted out.

Yes, I think you should have come out before you were married. But it’s too late for that now.

Yes, I think you should be honest with who you are.

BUT. I would hesitate to advise someone to come out to someone (whether it is your significant other or family member or anyone else) if you think it will do permanent damage to your life. If you think your crossdressing will end your marriage, then you may have a choice to make. It sounds completely simplified but it may come down to crossdressing or your marriage.

(Again, please seek out a counselor.)

Love, Hannah

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3 thoughts on “Ask Hannah!

  1. My answer would be “tell her!” But, I’m kind of privileged in that area… my wife knew I crossdressed before we even started dating. It took, and continues to take a LOT of work, but we are making the reality that I’m a trans woman (who is now transitioning) work. It’s still a (I know you hate this word Hannah) journey, but it’s such worthwhile work!

    Liked by 1 person

  2. Excellent well reasoned advice. I agree…definitely tell your SO the truth. The telling itself may also help an cross dresser better understand themselves.

    I would caution against doing little things to see if she notices. Silence is not approval. I would also caution against incrementalism. Your SO is not a frog in a pot…you cant gently turn up the heat and expect her to grow tolerant.

    Liked by 1 person

  3. You nailed it ! Dont test the waters with a bra! Man up! Tell her! But first be ready to answer the questions with truth! Why do u do it? Are u gay or bisexual? Do u want to transition? And be ready to answer them over and over again! Declare you love for her and tell her that will not change ! Tell her y you didn’t tell her earlier

    Good luck its a difficult situation

    Stevie/ Steff


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