Crossdressing among straight men is little understood, and wants to straighten things out. Resident writer Alex Hopkins speaks to two heterosexual men who share their crossdresser stories and how wearing women's clothes makes them feel.


Mother’s clothes

“My first time crossdressing was in my pre/early teens,” says Simon Walter Hoare, aged 56. “It was initially my mother’s clothing. If she left anything lying around, I was liable to try it on.” 

For Simon, who defines himself as a practising heterosexual who is very gay/trans and bi-friendly, crossdressing has been an escape, a way of making a fantasy a reality. “It’s also a way of identifying with certain perceived (fantasised) elements of femininity,” he explains. “I don’t have any pretence that it gives me any insight into what it means to be a real woman. But I do know how some of the clothes and shoes make me feel. So for me, it has always been a sensually and sexually driven way of bringing fantasy into real life.”


The power of heels

When it comes to crossdresser clothing, Simon has never wanted to achieve what he refers to as the 'full look'. “I’ve never aimed for a convincing portrayal of a woman. It would certainly be a doomed quest in my case,” he laughs. 

“I have always just chosen certain aspects which I particularly like, which would always definitely involve heels, it could never even start without them, and then the addition of other elements, like stockings and dresses. Most often without wigs and quite often without makeup. So yes, a guy in heels, stockings and short dresses. Does that mean transvestite? I would say absolutely, yes it does. We are all placed at some point along a spectrum of sexualities. For me, I only choose the trans elements which I think work for me.”


The anxiety and sadness of illusion

Like Simon, Andrea aged 40, got into crossdressing in his teens, finding himself increasingly drawn to the fashion pages of women’s magazines. “Crossdressing creates an inner battle. It feels good. Not in a sexual way but in an ‘I look good in this!’ and ‘this feels really nice’ way. At the same time, it creates anxiety and sadness because the body does not match the illusion I want to create. I am not trying to be a man wearing a dress. I am trying to get as close to a female appearance as possible.”

Young man in women's closet with a bra on his head.
"It was initially my mother's clothing"


“I was jealous of my female partner”

Andrea now wears skirts and dresses at home whenever he can. Coming out to his female partner, however, was, he says, extremely difficult. “When I saw a woman on the street, tube or in a café in a gorgeous outfit, I was jealous of her, because she could wear it and I couldn't,” he explains. “It was not a passing feeling or thought anymore in my relationship and resulted in several false fights with my female partner. I started arguments over nothing because I felt permanently jealous of her and had no way to escape it. But when I finally came out to her, she was open and accepting. We bought my first skirt together almost the next day.”

Simon’s wife is the latex designer Atsuko Kudo. “She is encouraging of all alternative sexualities so long as they are safe and consensual, as am I,” he says. “Previous partners have been the same. But you must choose your partners and friends based on an honesty about what you are and who you are.”


Support for ‘kinksters’

Both men have also found support in the crossdressing scene. “The community in the fetish scene has been particularly close and supportive,” says Simon. “London’s fetish scene over this period has grown to encompass a rainbow of kinks which I find to be particularly inspiring. There is nothing so good as seeing a myriad of kinksters having a great time bouncing off each other’s peccadilloes!”

“Fetish and LGBTQ forums exist en masse,” adds Andrea. “My advice is to find one to get tips and spend some time talking to someone. These forums make you realise you’re not alone.”


Transcending ‘normality’

“We are now living in an age where some of what we took for granted as freedoms are coming under threat,” warns Simon. “This makes it more important than ever to celebrate and encourage ‘difference’. I think crossdressing is one of the key parts of an open and healthy sexuality because it’s simply about expressing a desire to be something slightly different, more glamorous, more exotic. It’s about transcending normality and the every day, and fulfilling what’s in your heart. Such fleeting moments of joy can live with you forever. If you can share them with those closest to you that’s even better.”


Cover image from Flickr Creative Commons users: Eileen Healy

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I.  started by trying my mom's panties and pantyhose.  She encouraged me to expirement. 

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