How do you tell your wife, girlfriend or partner that you are a lifelong crossdresser?

How to Have the Conversation

This is the question I get asked the most. And it’s an understandable one. Most people have a reaction to discovering their partner is a crossdresser. It’s oddly a kind of final taboo that remains ‘shocking’, when in reality, it’s pretty harmless. It’s also a label that is individual to us all. Some of us are at the trans end, others at the occasional ‘fun in bedroom’ end, and the near infinite rainbow colours in-between.

That said, I get it. I really do understand why so many of us choose to live a kind of inauthentic life. Most of us have learned that revealing ourselves will lead to catastrophe. Sometimes destruction of lives, loves, hearts, egos, identities, I could go on.

It’s why so many of us have hidden in the shadows of guilt and shame.

But as we have grown older, so the desire to live a more authentic self has grown.

As relationships become more mature, as the end of the tunnel goes from a tiny pinprick of light to a giant glare in our faces, we start to ask, ‘if not now, then when?’

I have been lucky in that my partner knew very early on in our relationship and has embraced it. She doesn’t adore it for sure, but she is happy to see me happy and will indulge me when I ask.

Everyone is different and there is no silver bullet, no right way, no ‘safe’ way to share your truth. And for some, maybe it should stay a secret. Only you will know. It’s a risk either way.

My decision came about when I considered what I would regret on my death bed. And my hidden identity was number one.

That’s when I told my partner about Jenny Raven, the website, the books, the socials, the podcast. She took it on the chin, after all she know I was a crossdresser. She expressed that she felt lied to as I had not shared about Jenny Raven and our crossdressing in the bedroom days had long ended. But she understood. And now this bitter truth-pill is in the past, and with very little drama. 

OK so here are my tips should you be thinking of sharing your truth…

The Sooner The Better
There is never a good time, so the sooner the better. This is especially true if you are early on in your relationship.

Share The Trauma, Scale, Depth and Timescales
Help her see beyond what she will think of as just a ‘kink’ and a ‘lie’. Tell her your story. What happened as a child. How you have hidden this part of you in order to survive. How much it means to you now. The past trauma and way you may have experienced childhood and your feminine side will likely help her feel more and judge less.

Give Her The Power
Tell her you love her and that you will respect any and all of her decisions. Tell her you want this to work, and that you will put in the effort to do so. She may have a revelation of her own too, so be prepared.

Tell Her The Complete Truth
What seems to be the bigger trigger for most partners is not the crossdressing, but the fact that you ‘lied’ about it. Lie feels like too big a word, but it’s HER truth. So get it all out in one session. Hopefully sharing the trauma you experienced as a child (if there was any) will help her understand why this part of you has  been hidden. If you can convey that staying hidden is how you learned to survive as a child, she may understand. Again, prepare yourself, she may share a truth with you too.

Let Her Have Her Reaction And Respect Her Feelings
However she reacts, she is right. For her at least. Let her feel it her way, and show her the empathy and compassion you would like reflected back at you. It’s a leap of faith and as such, you must give up any and all attempts to control the outcome.

Establish Some Rules and Boundaries (which could mean you lose her)
If she accepts, it’s often a variant of three outcomes. First, ‘OK, but I never want to hear about it again. Keep it to yourself’. Second is, ‘OK, you can play with it with me on VERY rare occasions, and I will tolerate it’. Third is, ‘Oh yeah baby, let’s have some fun!’ Of course the final option is that your relationship fails totally. If this is the case, I would suggest that crossdressing is either stepping over some fundamental and likely religious ‘law’, or that your relationship was already in serious trouble.

Respect HER Wardrobe, DON’T Pinch Her Panties
This is a personal one for me. Don’t dip into her wardrobe unless invited. It’s HER clothes, and not yours to play with. This may seem like a strange boundary, and one you may have crossed, but only go there if and when invited. Your unwanted visitation may seem like a violation.

Investigate Why She Has Reacted Negatively and Empathise
If she reacts badly, investigate with an open heart and don’t make her wrong or argue. Simply try to understand. Her reaction is usually down to social norms, religion, or it could be the revelation shakes the foundations of male and female roles you have become used to in your home. See it from her perspective. Over time, so long as you don’t create friction, if she loves you and wants it to work, she will likely soften.

Be ready, she may want to open your Pandoras box
Yes, it might be terrifying or thrilling, but she may well want to see those shiny red six inch platform heels. And you need to show her if she asks. Show her it all. This may result in her laughing and having fun. Or shock and horror. Or even silent ambivalence. But if she asks, show her. If she is playful in your revelation, you might offer to show her too.

Ask Her To Accommodate: Most Likely Your Desire Will Diminish If You Are Allowed To Explore Freely
This is advice from me personally. Part of our desire is based on our needs being locked away. Once they are out, their power diminishes. Yes, you may go crazy for a month and spend a ton on Amazon, go to some events, play in the bedroom, but quickly that may subside as reality floods back in. Help her to understand this. Be clear that this is NOT about you changing gender, being gay or wanting an affair (unless of course you do want any or all of those things). She will likely make up stories in her head about what it means. We all do this.

Ask Her To See It More Like Cosplay
The more I have thought about it, the more I think, for me at least, crossdressing is like sexy cosplay. If she can see you as a fireman, maybe she can see you as the woman you want to be in the bedroom. It’s a HUGE ask, but it may also be the acorn from which your relationship flourishes.

And it may all go badly
Yes, she may leave. She may punish you. It’s your choice to stay. It’s your choice to remain hidden. There are no right or wrong answers. It’s about what we will tolerate and what we are prepared to live life with, or without.  I know from the surveys that I have conducted that many of us feel trapped in a relationship where it cant be revealed or has and it didn’t go well. I will post about this dilema in another article, I just wanted to acknowledge that for many, this situation is VERY real. 

OK lovely. Stay strong. You have one life. Lean on friends. No matter what you choose, it’s the right choice for now.

JRx

To understand the crossdresser experience better, read real stories in the 2025 Community Survey. For the partner perspective, listen to Episode Seven: Anna, The Crossdresser’s Wife on the Gurl Talk podcast.