Why do men cross dress?

As people start to pay more attention to the nuances of conversations about gender identity, we’re slowly improving our understanding of the ways people can define themselves and people. To help, we’re going to look at what ‘cross dresser’ means and share a story from a member of our community.

True Stories

What ‘cross dresser’ means

The term cross dresser means a person who dresses up in clothes traditionally associated with the opposite sex. Typically, it’s used to refer to men who dress as women. However, it can also apply to women who wear clothes typically associated with men. It replaced the term ‘transvestite’, which can be viewed as harmful due to the negative stereotype associated with it. It’s important to note that men who cross dress aren’t necessarily gay, transitioning from male to female or drag queens. Although some are.

You might be thinking ‘Why do men cross dress?’. Truthfully, there’s no one reason. Every individual is different. It’s simply a form of self-expression that some people identify with. The choice to wear a summer dress, for instance, can be a means of embracing femininity or simply enjoying the comfort and freedom it provides, regardless of one’s gender identity. Whether it’s the vibrant colors, flowing silhouette, or the carefree vibe it exudes, the summer dress embodies a refreshing choice for those seeking comfort and style in their wardrobe rotation.

True stories: Dating a cross dresser

Daisy wasn’t shocked when she found out her boyfriend was into cross dress. In fact she was relaxed about it. She tells us what it’s like when you date a closet cross-dresser. We’re handing her the mic to tell her story…

There he was. My boyfriend all glammed up in a dress and make-up. It had been nearly three weeks since he told me he cross-dressed and personally I was all for it. Him being so vulnerable with me honestly increased our sexual pleasure. But as he reached for the sunset red lipstick the same old concern ran through my mind: when was he going to come out to our friends?

Okay. Let me back track a little bit.

First Date

I met Andy when I was 21. I had recently been through a bad break up a few months before and was not looking for anything too serious. So when a friend introduced us at a party I was relieved. He was perfect: really friendly and easy to talk to. Plus, the long blonde hair and tanned skin didn’t exactly hurt matters. 

We decided to go on a date the following week. During which he bought me roses and paid for dinner. Honestly, I couldn’t have been more flattered. I’d almost forgotten what it felt like to be treated that way. But that wasn’t what piqued my interest. His easy going nature had the strange ability to completely disarm me. He made me feel comfortable and special, which can be a hard thing to find. Suffice to say, it wasn’t long before we had arranged a second date.

Little hints about cross dress

My relationship with Andy progressed surprisingly quickly. We had so many things in common. He ended up staying at my house most nights of the week. There’s no other way to describe it other than it just felt right. Eventually, things got even more comfortable. I jumped out of the shower one morning to find him trying on my hair clips. He laughed when I told him he looked pretty. At that point, I just brushed it off as curiosity.

But as these types of situations happened more and more frequently it became more and more difficult to pretend like there was nothing going on. A couple of times I even found him trying on my lipstick. I didn’t have a problem with it – I just wanted to know if he was a cross-dresser. That way he wouldn’t have to face it alone.

Makeover to figure out if he enjoyed cross dress

I decided to be subtle about finding out since I didn’t know how he would react. So after a few too many drinks one night I offered to do his make-up. He said he loved the idea. I was surprised how casual it was. It genuinely felt so natural. Before he had the chance to change his mind, I went upstairs and returned with my arms full of makeup, hairspray and accessories. Once I’d worked my magic, he looked great. Some people might find it hard to deal with but, personally, I thought it was sexy, especially with the red lip-gloss.

Coming out 

The makeovers became a regular night in for Andy and I. I never even gave it a second thought. We had so much fun experimenting with different clothes and styles. It was like going out with my best friend. The only thing that kept niggling at the back of my mind was that none of our friends knew. I never thought it would be an issue. Thing is, when I asked Andy about it he would instantly change the subject and become completely closed off. 

I nagged for months before I took matters into my own hands. Eventually, I turned to one of my close friends. She wasn’t judgmental at all and she listened with an open mind. Perhaps unsurprisingly, when I told Andy he flipped. He said I had betrayed his trust and gone behind his back. He left my house and stopped talking to me for a week. At the time, I couldn’t believe how unreasonable he’d been.

If you’re looking for support with coming out, check out our articles ‘how to come out’ and ‘how to come out to yourself’.

The truth about his cross dress history

Andy finally called me after two weeks. He said we needed to talk. I told him I was hurt after he gave me the silent treatment and he apologised for that. In fact, I felt like for the first time in our relationship he was actually open and honest with me. He told me that only his parents knew about his cross-dressing. Unfortunately, when he opened up to them they were very critical and accused him of being gay. Although they gradually came round and embraced him, he was worried that his friends would react in a similar way. 

He figured that boys would respond differently to girls. That’s why he’d told me. I finally saw it from his point of view. I felt terrible for outing him. With hindsight, I can fully appreciate that that wasn’t my story to tell. After all, it’s still a very taboo subject which a lot of people don’t really understand. That can lead to a lot of unwanted and unsavoury opinions. Still, I suggested that he tell his best friend, Jack; an understanding guy who he had known for years. At least then he would have some support. He said he was open to the idea but it would just take time.

New Beginnings

Things between Andy and I fizzled out. I think after the whole argument he felt I’d been a little pushy. But we stayed in touch and most importantly remained friends. A few months down the road, I found out that Andy had come out and I was delighted. He called me up one day with the news that he had told Jack. Not only did Jack understand, but also he threw him a party where everyone had to come in cross-dress to make him feel more comfortable. I thought it would be hard initially, and some of his “friends” did make some mean comments, but over all people reacted positively. With open-minds.

Now Andy is comfortable enough to turn up to parties in makeup and women’s t-shirts. I’m so glad that he’s now able to be himself without any apologies. He actually taught me a lot about gender expression, why men cross dress and letting people come out on their own terms.