Dear Roe,
My husband and I retired four years ago, we're in our early 60s, fit and still in love. We never had children, by choice. Our sex life has always been good, though not adventurous. My husband has always had an interest in lady's underwear, shoes etc. I often thought he cross-dressed in secret, and lately he wished to wear underwear when we made love and I agreed, though I had some reservations. Later, I asked him why, he said it excited him, he loved the feel of women's clothes. I must admit it gave me an extra buzz. He has asked that a couple of times a month that we both dress for role play. This is certainly not something I can discuss with my friends. I should add that he says he has no desire to go out dressed and would be devastated if anyone found out. He is a kind, private man, with few friends. How should we proceed?
This is one of those letters where there doesn’t seem to actually be a problem at all. Your husband enjoys wearing women’s underwear; you don’t seem to mind this at all and in fact seem to enjoy your husband’s pleasure.
What’s particularly wonderful about this letter is that you’re giving a perfect lesson in how a relationship can grow and evolve over time. You’ve been married a long time and you’re in your 60s, which means that you are in a demographic whose emotional and sexual lives are desperately underrepresented and underacknowledged. But here you are, still in love; still learning about each other; still being curious, open-minded and loving about each other’s desires – and, most importantly, having fun.
You’re trying something new and exciting, not just sexually but emotionally. You say that you suspected your husband enjoyed dressing up in private, but now he’s asking to bring that part of him to your sex life. I hope you realise what a trusting, loving step he has taken – to ask you to know him in an even more intimate way than before, emotionally and sexually. And you have met him where he is, being understanding and open-minded and willing to share a new experience together.
As I have addressed before in this column, “cross-dressing” is a term that is increasingly out of date. Cross-dressing is defined as wearing the clothes or adornments of the “opposite sex”, creating a strict binary between male and female. It perpetuates such a rigid idea of gender and gender expression, to assert that for a man to wear clothes labelled as “women’s clothes” is inherently transgressive. But it’s just fabric.
“Cross-dressing” narratives largely focus on men – although queer women do experience a huge amount of homophobia and transphobia and policing around their gender expression – highlighting how much we demonise men who embrace femininity, or explore their sexuality outside of stereotypically macho and dominant ways.
There’s an inherent suspicion around men who explore their sexuality in ways that don’t align with traditional ideals of masculinity. These suspicions are rooted in homophobia, misogyny and toxic masculinity; the idea that men and masculinity must always be aligned with dominance, and must eschew any trace of femininity.
Experimenting with clothes and lingerie does not have any inherent links to sexual orientation, or gender
This view is damaging and oppressive – and it’s also so boring. Imagine wanting to limit people’s sexual and personal expression so much that you demonise the colour and style of the underwear they occasionally wear; or erasing the complexity of a person and judging them just because they occasionally like wearing dresses? So many of the ways that we police gender and sexuality aren’t just damaging and oppressive and lacking in empathy; they’re also just limiting and joyless.
Which is why it’s incredibly brave that your husband is choosing to share this part of his sexuality with you. Note I said sexuality, not sexual orientation. Experimenting with clothes and lingerie does not have any inherent links to sexual orientation, or gender. A lot of straight cis men experiment with wearing women’s clothes in their private and sexual lives, and it does not mean that they are gay or bisexual, nor does it mean they are transgender. (Though people of all orientations and genders can play with their expression through clothes.)
Cross-dressing is, for many people, a temporary escape; an act of exploration and play; a desire to see themselves in a different way and explore a different side to themselves. Show me single person who has worn a costume, had a makeover, tried some roleplay, or bought some elaborate lingerie and who can’t understand the feeling of putting on clothes to make you feel a different way about yourself.
It’s a testament to your relationship that your husband trusts you and is inviting you to share this exploration and joy with him – and that you’re supportive and open-minded and eager to explore.
You mention he would like you both to dress up – what does he envision you wearing, and are you comfortable with that?
To begin, I’d start an ongoing conversation about the role you both see cross-dressing playing in your life and relationship, so you can both explore your comfort levels and boundaries. Does your husband want to spend entire days and evenings dressed up, or specifically during sex? You mention he would like you both to dress up – what does he envision you wearing, and are you comfortable with that? Do you want to do an entire roleplay with specific lines and acts, and how will you negotiate feeling safe throughout this? Does your husband always want you to be involved in his cross-dressing, or does he also want to enjoy it privately on his own? As you explore, more questions or specifics may arise, so keep communication open. As with all sexual activities, consenting once is not consenting always, and it’s vital that you both feel safe, comfortable, free to stop at any time – and that you’re both enjoying yourselves.
Connecting with other couples who engage in this type of play may be important, so that you have people with whom you can openly ask questions without feeling judged. Online discussion boards and groups will be helpful; as will doing some reading about how common cross-dressing has always been, historically. One warning is that a lot of documentaries and media portrayals of cross-dressing go for salacious or stigmatising representations, equating cross-dressing with moral deviancy or mental health issues. Do not let these discourage you; other people’s ignorance does not define your husband or your relationship.
Have fun. And congratulations on being a great example of a long-lasting, ever-evolving relationship.