Clickbait and Crossdressing

Every so often I come across a click-baity article along the lines of “Why Having a Husband Who Crossdresses Is The Best Thing EVER”, “How To Come Out To Your Wife” or “How To Get Your Wife To Let You Crossdress”.

And look, this is not to attack or criticize the writers of these pieces or the websites that publish them. I admit they can be fun to read. They tend to be lists with short sentences that are light-hearted and, well, optimistic, I guess.

These articles typically focus on the potential… benefits of having a partner who likes to dress up and/or wear makeup. Some of the pluses are being able to borrow your husband’s eyeliner or accessories, and having someone to shop with.

To be fair, my wife will borrow my makeup from time to time or wear one of Hannah’s necklaces, so yes, in our marriage there are things that you could consider benefits. Early on in my discovery of my gender identity I found I was able to relate to my wife on a different level when we chatted about feeling frustrated when our shade of foundation was sold out or something along those lines. Some of my friends complain about how long it takes for their wife to get ready but once the heels were on my foot I could understand that doing your makeup and selecting an outfit sometimes took longer than expected.

Of course, it took a lot of time and a lot of patience and conversations to get to where my wife and I are today. It took a long time for her to be comfortable and secure with who I am.

These articles seem to be aimed at the partners of a crossdresser, but they often feel like they are written as… hm, talking points for the crossdresser themself in regards to coming out to their wives.

Let me explain.

There’s a million different ways to come out to your significant other. And almost every single way is wrong. There’s really no right way to do this other than being honest and transparent and doing it early in the relationship. Waiting until after the two of you are engaged or married is probably not a good idea. You need to have the talk before there’s an invested commitment, whether it is proposing or having kids or buying a house.

It’s not uncommon for a crossdresser to consider their method for coming out by focusing on the positive sides of having a partner who likes to dress up. Some crossdressers think that “selling” their partner on crossdressing is the right approach. What I mean by this is hyping up a benefit of having a partner who crossdresses.

For example:

“Hi honey, I like to wear makeup and you can borrow my lipstick anytime you want!”

“I know you love to shop for clothes and now we can shop for clothes together!”

“Wouldn’t it be fun to dress up and have a girls night out?”

I am guilty of saying variations of these things to my wife and I quickly learned that her initial reaction wasn’t an enthusiastic agreement. I learned that if my wife wanted to be married to her girlfriend she would have married one of her friends. No, she wanted to be married to a husband and I thank God every day she wanted to marry me.

Over time she would indeed borrow my makeup, we would shop for clothes together, and have many girls nights in. These moments took a long time to get to. They took work, patience, difficult conversations, and trust.

And to be fair, there are times when our significant others DO initially react incredibly positive and supportive and excited when we have The Talk but I think it’s naïve to expect that kind of reaction.

And! If your partner doesn’t respond with enthusiasm to your coming out it does not make them a bad person. It doesn’t mean they hate you or not want you to be yourself. It doesn’t make them anti-LGBTQIA+. Someone’s partner coming out as anything but cis and/or heterosexual is a LOT to take in. It’s a LOT to process. Their partner’s gender/sexual identity impacts their own identity in various ways.

Again, I think some of these articles are targeted towards the crossdresser themselves. They are supportive and encouraging of the crossdresser in regards to coming out to their partner. And yes, it’s important to be honest, it’s crucial to have support and encouragement and talking points, but if often feels that these articles aren’t…. helpful.

They tend to focus on the practical side of being able to share a wardrobe/accessories/makeup/purses/etc. And yes, that is a benefit, at least in my experience. But I think it will take a loooong time and it may take many difficult conversations and intense emotions for someone to see any sort of pluses to having a crossdressing partner if it happens at all. I think some of these articles can be misleading to a crossdresser. They tend to be lighthearted and… well, everything a crossdresser would love to read.

We fall in love with our significant others for some many reasons. They are our crush, our best friend, our… everything. We have emotions and desires for them that exceed anything that we have experienced before. We want to share and experience everything with them.

And I do mean EVERYTHING, particularly crossdressing.

We want our partners to know everything about us and, ideally, share our crossdressing with them. We may daydream about our partners shopping for lingerie with us, dressing up and hitting the town or a million other things. I have had these thoughts too.

Wanting to come out to our partners is sometimes influenced by wanting to do these things with them. But the real reason we should come out to them is because they need to know about this side of us.

And why do they need to know? Well, because this side of us might be a deal-breaker for them. I think this side of us might be too much to ask of our partners. They may not want to commit to someone who is on a journey when it comes to their gender identity.

And that is completely fair. It does not make them a bad person.

Look, if I was dating someone who wasn’t sure of their sexuality, I would hesitate to commit to them. I would want them to be secure and confident of who they were and who they loved and who they wanted. The same thinking can be applied to your partner’s gender identity.

I think these articles (and I admit I am probably taking them too seriously) give a… misleading idea on how coming out to our partners will go and how we should have The Talk. The articles tend to be fun and playful, but this revelation rarely is. They make it all sound so easy.

I also feel that these articles can be a little harmful to our partners. When we come out to our significant other it will more than likely turn their entire world inside-out. It will create a myriad of emotions and fears and questions that feel impossible to find the right words to ask. For some their reactions feel contradictory and even hypocritical. Your girlfriend may be the biggest supporter of the trans community, buuuuut when her boyfriend tells her that he likes to dress up, her reaction may be less than enthusiastic. She may not come off as supportive or excited.

It’s just… different when someone close to you comes out. Their gender identity will impact your relationship. Gender identity is a journey, a work in progress. It’s not an easy adventure. T-girls and crossdressers spend much of their life discovering who they are and our identities shape our life and choices (and vice-versa) as well as what is right for us.

When I came out to my wife while we were dating she had the normal questions. One of those questions had much to do with who I was, where *this* was going, and what I wanted. I knew transitioning wasn’t for me, but she didn’t know that, no matter how confidently I told her that it wasn’t. My crossdressing was an x-factor, a variable that could create a change in my life in terms of my gender identity.

Is it possible that someone who “just crossdresses” may transition? Of course, absolutely. I am sure that many trans girls who live full time or takes (or has taken) hormones thought that *this* was simply about clothes only to realize after some time that *this* was indeed MORE than clothes.

When people commit to each other, they consider the future, they consider if this is the person that they want to build a life with, whether it is traveling the world or raising a family or anything else. A commitment is typically meant to be a long-term plan, it’s usually meant to be forever. People who make this commitment consider anything that could impact their new, shared lives. And yes, someone’s gender identity could potentially impact that.

Look. I’m trans. I heart the trans community. I GET it, as much as one can understand someone like us. However, if I were dating someone who wasn’t quite sure of their gender identity I would hesitate to commit to them. Like one’s sexual identity, I would want that person to know they are. I know from personal experience that *this* is a journey and we need to be as sure as we can be about who we are before we really commit to someone else.

And yes, I know that gender identity and what we want and who we are can change over time, ever after decades of marriage. It happens.

When we come out to our partners, they often do what they can to try to understand this side of us. The internet is what we turn to when it comes to figuring something out, whether it’s how to blend foundation, replace a bathroom sink faucet, or trying to understand why your husband wears panties.

Googling ‘crossdressing’ is rarely helpful.

These search results provides websites about transgender dating, fetishy blogs, and the like. We can tell our wives that *this* isn’t about sex or wanting to be intimate with a man, but search engines can contradict what we say and what we feel and believe.

If your significant other comes across a list along the lines of “Why Dating a Crossdresser is the BEST THING EVER” it might not help them. Your partner is looking for clarity and support, not… naïve benefits. As I said, these lists tend to play up sharing a wardrobe or your wife suddenly has a new best friend to hit the mall with.

Buuuut our significant others probably aren’t (at least initially) super excited that their man wears pink thongs or they have a femme name. Lists like these might contradict what our partners are feeling. They usually portray having a crossdressing husband in a very naïve, overly rose-colored-glasses way. These lists rarely mention the emotional crisis and fears that our partners typically have.

Additionally these lists may even cause our partners to wonder if there is something “wrong” with feeling scared or confused or angry about their man’s crossdressing. The lists discuss how having a crossdressing husband is nothing but a positive thing because you can share mascara or talk about purses… but your partner isn’t there yet, if they ever get there at all.

To put it another way, I recently finished a book that I thought was, well, kind of stupid. But everyone I know who has read it has LOVED it. It honestly made me wonder if there was something wrong with me or with my reaction to it. Did I miss the point of the story? Am I wrong?

Again, I admit these lists can be fun to read from time to time, but I would caution using them as a guide for coming out to your significant other. As I said before there’s a LOT of wrong ways to come out to your partner. Telling them “honey, guess what! You’ve just doubled the size of your wardrobe!” probably isn’t the right way to tell them.

Love, Hannah

8 thoughts on “Clickbait and Crossdressing

  1. I’ve been married—and divorced—twice. My inability to live authentically was a large factor of why we broke up. I don’t blame them as I know now that my fears drove me to try to suppress my inherent identity. True, they were also afraid and unhappy about what I exposed about my true self.

    I’m soon to be 66 years old and start to ponder my life and how more I may have of it. An important learning for me is that living authentically to oneself is so fundamental to my happiness.

    We know that trans authenticity may be a need for occasional crossdressing to full-on transition. All are perfectly valid and human and real.

    It’s thus so important to risk being real with our partners, ideally before marriage or commitment.


  2. These folks don’t really put themselves in their wife’s shoes. How would they feel if their wife was TG? Secondly,I have heard several tales where the wife was originally supportive and then soured on the whole thing


  3. Very well written. And thank you. One of the most realistic writings on this topic I have seen. There is no doubt that there can be wishful thinking, and realistic thinking when it comes to how a relationship will go between two people when “the crossdressing side” is shared. No doubt many who read this will have hard conversations around much of the subject matter here. There are too many places that sugar coat the potential outcomes, and the need to have real and fully honest conversations, and to be honest with yourself all along the way. Thanks for writing this.


  4. I am in a long term committed marriage. We have come to an understanding and a balance about my crossdressing. Yes, I would dress more often if I was alone, but I am not — and she and the marriage is more important to me. I have come to believe that very few cis women “get” and embrace crossdressing. All the recent negativity in the press and the R’s making trans issues a wedge issue doesn’t make it any easier. Thanks for your honest take on this issue. Nancy


  5. Thank you Hannah for another interesting post.

    I married a long time ago – late 90s. But, (and this is only approximate), my crossdressing started (goodness only knows how) around 16 years ago. Did I always have interests? I don’t know. Maybe I did, but I just didn’t know it. I DO have very vague recollections of briefly trying certain garments on as a youngster whilst still living with my parents but it doesn’t resonate beyond that.

    I’ve probably answered my own question there but still, my point is that it was long beyond the point of being able to broach the subject before it was too late. It wasn’t in any part of my thought process when I got married anyway – far, far, far from it.

    Fate is a critical thing. Fate allowed my (lingerie) crossdressing to be sustained (albeit with the odd period of abstinence for whatever reason) until March 2020 when the pandemic struck and affected everyone in the household and the circumstances that allowed my dressing time and the period in which I could ‘do’ it.

    There have been certain indicators over the 16 or so years that tell me it wouldn’t go down well anyway if broached, from general (and sometimes ignorant and inwardly frustrating) conversations in the household on any given day, to that moment of dread when I was caught in a state of partial crossdress, after the significant other had returned home suddenly and for me, unexpectedly and I rapidly began the strip before it was too late. Only it WAS too late despite best efforts.

    I mitigated the circumstances, citing emotional turmoil caused by the transition of someone close to me and of ‘trying to understand it’, when in fact, I understood entirely within. I know. Coward. But right then, it was about protecting everything I held dear, yet had put at risk by my own levels of addiction. It was pure and simply, kink.

    The irony is that, since March 2020, I have been unable to indulge, and are unlikely to be able to do so again as far as I can tell, so I merely accept and appreciate the time that I had and the circumstances that allowed it, albeit in secrecy. Maybe fate has gone some way, but not all the way, towards addressing the balance.


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