Crossdressing is defined as the act of wearing clothes traditionally or stereotypically associated with a different gender. I.e. men dressing in women’s clothing.
Socially, it means different things. Drag (Queens or Kings) is cross-dressing as a performance art.
If a girl/woman wears her boyfriend’s clothing it’s considered cute, or gay. There’s even a style of women’s clothes called ‘boyfriend jeans’ and ‘boyfriend shirts’.
The crossdresser stereotype
If a conventionally attractive man crossdresses, he’s seen as brave and challenging gender stereotypes. If a man not considered conventionally attractive crossdresses, he’s seen as a weirdo or a freak and someone to avoid.
And when someone does something evil or criminal while cross-dressing, it tends to have an unfair negative impact on the community and public opinion. There’s not one thing that defines a crossdresser. They can dress for comfort, performance, confidence, sexual pleasure, or a multitude of other reasons.
There’s nothing bad or wrong about it, and it doesn’t necessarily mean the person is gay or transgender, but some might be cross-dressing for those reasons.
A surprising fact I found out when my ex started crossdressing, is a large majority of crossdressers, who are men, are cisgender heterosexual men. Many crossdressers only wear their clothes at home and are so secretive about it, for fear of what others might say or think about them, that even their partners don’t know.
I was one of these partners.
A suitcase full of women’s underwear
My ex and I broke up and got back together many times. During one of these break-ups, I was packing his things and noticed a suitcase full of women’s underwear he had hidden under our young child’s bed.
My first thought was that he was cheating on me, and he’d kept these as creepy reminders.
When I confronted him, he told me they were his and he enjoyed wearing women’s underwear. I didn’t have a response at that time because I was in shock, and even though I was very open-minded at that point in my life, I wasn’t as open-minded as I am now.
Also, we were breaking up, so I didn’t see a point in exploring the issue further.
Cut to a year later and he was back in town and back into my and my kids’ lives. One day, I was doing laundry and noticed all of his underwear were silky or lacy women’s underwear.
We had another conversation where he told me he still enjoys wearing them and they help him feel sexy and he liked the way they supported him. I shrugged it off figuring no one can see his underwear.
His new wardrobe choices
A few years later, when our child was graduating from primary school, his personality suddenly changed. He started giving me the silent treatment and leaving without telling me where he was going and spent a few nights at the house of a ‘friend’.
After about a week, he came back and seemed like he was back to normal except he started wearing women’s athletic wear around the house.
If any of us questioned his new wardrobe choices we were yelled at or ignored.
There was no ‘hey babe, this is what’s going on with me’ chat and no explanation to the kids who were very confused and concerned for me.
In no time at all, he had a wardrobe twice the size of mine and the kids combined. He stopped contributing financially and the majority of his income would go on cross-dressing, even though, at this stage, he would only cross-dress at home.
He could walk in high heels better than a lot of women I know.
Going public
The first time he wore these clothes in public was unintended. We were on our way back from a weekend down the coast and he was wearing a bra with rolled-up socks in it to simulate breasts, stockings with black booty shorts over the top, and thigh-high boots.
He overtook a car when he shouldn’t have and got pulled over on the highway and had to exit the car to talk to the officer.
I remember my middle child talking about how embarrassing it was for him. After this incident, I noticed the kids stopped inviting their friends over because women’s clothing was all he wore when he was in the house.
It made them very uncomfortable and he didn’t seem to care. A few months after this, he started wearing the clothes out in public when he went to the supermarket.
I supported him as best I could
I didn’t judge him, I defended him and I let him use my online shopping portals to purchase the fake breasts, female body suits, wigs, and other things he wanted that he couldn’t get locally.
I taught him how to do his nails and looked up makeup tutorials for him.
When he grew unhappy with his job, I spent hours looking for jobs he could do where he could crossdress in comfort and safety.
When he started wearing the lingerie and breasts while we were being intimate, it didn’t turn me on but I didn’t have the confidence within myself to speak up.
Was it me?
I tried to understand him better. To understand why he was cross-dressing.
Was it me? I wasn’t very feminine and didn’t enjoy wearing makeup and I was the one doing the ‘traditionally masculine thing’ by paying all the bills.
My inner feminist was screaming at me to wake up and stop blaming myself, but she was being silenced by depression, anxiety, and
fear.
I’m someone who likes to understand human behaviour and I really tried to rationalise this in my head, which frustrated me to no end. I have two kids in the LGBT rainbow. One of my best friends is gay. I am someone who believes people should be able to wear whatever makes them comfortable.
I have bought my oldest child dresses in the past before they came out as trans.
So why was I having so much trouble accepting my partner as a crossdresser?
I still don’t have an answer for that.
My failure as a woman and partner
When he told me he wanted to look into getting actual breast implants, my mind spiralled again. Did it mean he was trans or non-binary? He said no, he just liked wearing the clothes and they made him feel more confident and more sexual.
I internalised all of this as my failure as a woman and a partner.
Especially now that we’re not together and he’s not cross-dressing as much.
Was it a mid-life crisis?
Was it something deeper?
I have no idea.
I have talked to many women who’s partners crossdress and their stories are very different to mine, so my experience definitely is not the standard. Not all of these women stayed with their partners, the cross-dressing being a key factor in their break up.
But it wasn’t a key factor in ours.
What I learned from this experience, is communication is vital. Especially with big life changes and when there are young people involved. Everyone is different and we all have quirks about us that make us who we are. There is nothing wrong with being a crossdresser.
But it’s not everyone’s cup of tea, and if you are someone whose partner happens to enjoy cross-dressing or anything else, and it makes you uncomfortable, it’s okay. It doesn’t make you a bad person if you end the relationship.
Everyone deserves to be with someone who accepts them for everything that makes them who they are. I also learned to stop judging people for making choices in their lives that I wouldn’t make in mine.
I don’t have to walk in their shoes, nor do they mine.
What to read next
- Sexpert Warns against this Dangerous Sex Act that Many Couples are Doing
- Dating Red Flags for Single Mums – 12 Things You Should Not Ignore
- Yes, My Husband and I Have Sex on a Schedule
Support Services
- The Gender Centre
- CrossDresser Heaven (Find Local Support Groups)
- Check Facebook for various Support Groups in your area
