Dating a Crossdresser

Welcome to She’s My Man – The journey of a dating a crossdresser and being the older sister of another. Thousands of people have fallen in love and care for someone who enjoys dressing in the opposite genders stereotypical clothing. Everyone has different experiences, different thoughts, challenges and enjoyments yet, it’s not often the partners of a crossdresser that are thought about.

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Being a person who crossdresses is not easy. Even though western society is becoming more accepting and open-minded of what makes people happy, there is still prejudice and bigotry. As partners and relatives of people who crossdress, every painful comment and judgemental scowl not only hurt the person we love but hurts us as well.


We yearn to support the people we love and help build their confidence in a world that can be so cruel but, who is supporting us?


You caught your younger sibling trying on your clothes and put it down to experimenting. They’re now borrowing your clothes on a regular basis and owning some garments of their own. You could understand it when you thought it was just experimenting but now you think it’s something more you’re scared and don’t know how to protect them – You’re not alone.

You may have been married for 10/20+ years and you caught your spouse wearing your clothes. The shock, feeling of betrayal and questioning if you even know this person is devastating. The guilt and anger you feel are overwhelming and your world is crashing down around you – You’re not alone.

You’re head over heels in a new romance and your partner reveals their secret, you’ve always seen yourself as an open-minded person and even have many friends in the LGBTQ community but, for some reason, you’re struggling with the news. your partner is no longer who you thought they were and the relationship is taking on a new dynamic – You’re not alone.

Dating someone who crossdresses is your thing, you actively seek out this lifestyle but your partner is in the closet and you’re desperately trying to help them go public and celebrate who they are – You’re not alone.

You’ve known about and accepted your partner dressing up for a number of years now but the frequency has been increasing. You’re worried if this is going to turn into more than just cross-dressing and if they’re going to transition – You’re not alone.

I have read about hundreds of different scenarios and experienced many of my own, all with their own struggles and curiosities that challenged my views, challenged me as a person and challenged my relationships with the people I care about. All while feeling like there was no-one to talk to who could see things from my perspective.


This blog is to share my own experiences that are both bad and good. How I aid in supporting my partner and younger sibling but most importantly, all of the personal, moral struggles I’ve fought with.caring for people who cross-dress has made me happy, sad, scared and most painfully – angry.


Hopefully, if you are the partner of or related to someone who crossdresses, you will be able to find meaningful advice, stories you can relate to and inspiration to supporting your loved one.


If you are a person who likes to cross-dress, then I hope this blog gives insights into the involuntary internal struggles your loved ones may be facing and how you can support them.