My girlfriend is not happy with my cross-dressing

Tell Me About It: I sense my cross-dressing is a touchy subject with my girlfriend as marriage looms on the horizon

PROBLEM: I am reaching out to you as a straight cross-dresser who is in a long-term relationship. We are coming to a junction in our relationship where marriage is a real possibility but my cross-dressing remains a touchy subject. I have always been honest about this side of me, but I sense my girlfriend has serious reservations which we find difficult to address, leading to rows.

If you were to meet me on the street I doubt you would suspect this feminine side of me. I work in construction, I play on the local football team every week, workout in the gym, I often go out with the lads and do other “stereotypical” masculine activities. I don’t buy into such stereotypes, but in this situation it is important.

To confirm, this is not an act or over-compensation. I enjoy these elements of my life. I just so happen to enjoy cross-dressing and participating in “traditionally feminine activities” too. This side of me is every bit as real and cannot be switched off. I can say with confidence that it is my more masculine side to which my girlfriend is attracted! Which I understand.

She tells me that she loves me, but fears that I may one day say that I want a sex change. The thing is that I know that I never will transition but have difficulty when trying to reassure her.

With marriage potentially around the corner I feel that this is now the point where we either do take the next step of the relationship or run the risk of it breaking down.

ADVICE: You are bringing up some very important insights regarding cross-dressing and some of the myths around it that need to be dispelled: cross-dressing is not a sexual orientation and those who engage in it can be straight, gay, bi-sexual, A-sexual or other. It does not indicate a desire to change gender, or transition, though some people might choose this.

The joy of cross-dressing is that it allows a person to play with an alternative identity that someone can engage or experiment with as they desire. It challenges our traditional ideas of gender in that one person can occupy male and female genders at different times of their choosing and with all the joy, flexibility and daring in it. It is sad that so much of our society is afraid of this desire.

It sounds as if you have to hide your feminine side when you are engaged in stereotypical masculine activities and while you might expect a reaction in these settings, it is in your close, intimate relationships where it really matters that you are accepted fully in all your aspects. If we can feel totally ourselves in our private lives, we often have the courage to take on the external world knowing that if we get battered or bruised we have a safe place to return to.

She may need to engage more with the world of cross-dressing so that her fears and concerns are allayed

You clearly see your girlfriend as this safe haven but while you have had many years to come to a place of acceptance and peace with your cross-dressing, she may be relatively new to this concept and her vision of what her married life might look like may be taking a hit. You sound very grounded in your self-knowledge but you may need to have patience and faith (in the relationship) while your girlfriend grows in understanding and knowledge.

I wonder if it is enough that you are reassuring. She may need to engage more with the world of cross-dressing so that her fears and concerns are allayed. It is possible that her fears may come from her own upbringing and your behaviour might be exposing some her own family-of-origin issues around gender and sexuality. Some sessions with a couple therapist or an individual therapist who has knowledge of this area could be very helpful in directing both your attention to the surface and underlying issues that exist in your relationship.

If you are planning on spending your life together this investment is very worthwhile as we create patterns in our relationships that can be very difficult to change at a later date.

There is also the greater picture: that of the community you both live in.

Ideally, that community supports your marriage through its rough patches but if your issues are hidden from them it means that your relationship is more vulnerable. Are there friends or family on both sides that might be trusted with what is going on? Not only would this disclosure offer more back-up for you both but it might also disperse more true knowledge of what cross-dressing is in general.

While men often believe other men will be prejudicial in their response to something like cross-dressing, this is very often not the case and increasingly men are opening up to speak about the diversity of desires and identities. Of course you need to choose who to disclose to with care but cross-dressing in itself challenges so much of status quo that speaking more openly should simply be another step in creating freedom of expression.