How do I tell my girlfriend about my secret cross-dressing?

Dear Roe,

I’m a guy in my mid-30s who’s always had a penchant for cross-dressing. I’m in a long-term relationship and would really like to tell my partner but I’m unsure about how she’ll react to it. I have a profile online on a swinging website and I’m constantly being told I look great while I’m dressed up. It’s not something I’m looking to stop doing and would love to introduce my partner to that part of me.

I think it’s wonderful, and really important that you want to tell your partner about this aspect of your life. In a long-term relationship, it’s vital that we feel safe and supported and loved enough to live honestly and authentically – because otherwise, what’s the point?

I will say, on a slight side note, that I hate that “cross-dressing” even needs a label, or a coming out, of sorts. Cross-dressing is defined as wearing the clothes or adornments of the “opposite sex”, creating a strict binary between male and female.

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But biological sex is not the same as gender. While a person’s biological sex (male or female) refers to their chromosomes and internal and external sex organs, gender refers to the socially constructed ideas, behaviours and roles associated with being masculine or feminine – and how a person identifies with these ideas. Many people, such as transgender people, find that their gender and biological sex do not align. For example, someone who is assigned male at birth based on their biological characteristics may find that in life they identify as a woman, and thus live as a trans woman.

Other people, such as gender non-binary or genderqueer people, find that the divide between what is deemed feminine or womanly and masculine or manly is too limiting, and feel that they are neither exclusively masculine or feminine.

And then some people do identify with one gender, but occasionally like to play with their expression of masculinity and femininity. So a person like yourself could identify as a man, but enjoy playing with your gender expression by occasionally dressing in feminine clothes.

All of these things are common and should be celebrated. Our identities are wonderfully complex, multi-faceted things. Trying to reduce and define individuals by tiny, arbitrary checklist boxes like “sometimes wears dresses” deprives individuals and society of all the possibilities of expression.

I hope your partner holds a similar view. But sometimes people who have excellent intentions in theory fail to live up to these ideals when confronted with an issue in their own lives, and I’m guessing this is why you’re unsure of how she will react

Fear

Taking a two-step approach to telling your partner could be helpful. The first step is to introduce her to a range of different gender expressions generally. Often people fear expressions of gender or sexuality simply because they aren’t informed about them, and don’t know what it means. Share information and entertainment and media about people who defy traditional ideas of gender and expression, so that she grows comfortable with the idea and understands that people who do this aren’t any less human, any less fantastic, any less worthy of love.

Sharing this media together also means you can open up a dialogue about gender expression and cross-dressing, and address any concerns, misinformation or biases she may have, so that you can feel safer and more confident telling her about yourself.

When you are ready to tell her that you enjoy cross-dressing, be clear on what it means for you, so that she understands this isn’t something that will detract from your relationship, but add to it, as you live more honestly and authentically.

Tell her what role you see cross-dressing playing in your life and relationship, so that she knows what to expect and how to support you. Do you enjoy going out while dressed as a woman, or is it purely a private activity to indulge at home? What would you like her involvement to be, if any? Do you find it arousing, and want it to be part of your sex life with your partner, or is it a solo activity?

And tell her that you’re telling her this because you love her, trust and feel safe enough with her to be yourself, and that your connection and intimacy is reaching a new level.

It may take her a little while and some questions and conversations to fully understand and accept it, as is often the case when people encounter new information, so be patient as she processes. Hopefully, she’ll be supportive.

I do need to note one thing, however. I understand that if cross-dressing has so far been a private, hidden part of your life, you might understandably seek out some acceptance and validation online. However, there is a big difference between being part of a supportive chat-based community and being on a swinging website. Swinging is the act of being sexual with other couples, of engaging in non-monogamous sex practices – and you haven’t said that you’re in a non-monogamous relationship.

You might not intend on cheating, but it could well be seen that way. Being on a website designed to arrange sex with other people while in a monogamous relationship is not fair behaviour – no matter what you’re wearing.

Roe McDermott is a writer and Fulbright Scholar with an MA in Sexuality Studies from San Francisco State University. She’s currently undertaking a PhD in Gendered and Sexual Citizenship at the Open University and Oxford.

If you have a problem or query you would like her to answer, you can submit it anonymously at irishtimes.com/dearroe