Tell Me About It

I cross-dress and I’m worried I’ll end up alone

I am sexually attracted to and date women who are fascinated by me, but it goes nowhere because they are just getting their kink on

PROBLEM: I am a 49-year-old man, married to my childhood sweetheart with a couple of kids. I work day and night to make sure they are provided for. I purchased properties during the boom, but I had to give them back to the bank, which has been a stress.

I don’t let that get to me because I have a safety valve. Since I was four years old, I have dressed as a girl. I never told my girlfriend because I was afraid she would not marry me if she thought I was a “weirdo”. I also believed that I could give it up for love.

However, I could not stop dressing as a woman in my spare time, and I took that time out of our relationship, as another man might for a hobby or a mistress.

When she found out she gave me an ultimatum – to stop or leave – and she kicked me out of our house. Because I love her and our children, I immediately burned all my wigs and dresses and turned my back on my secret life.

After more than a decade I started again, and we separated but live together for the kids. I still love her but lead a free and single lifestyle.

I am sexually attracted to and date women who are fascinated by me, but it goes nowhere because they are just getting their kink on. I date but don’t sleep with men, because I understand them, and they treat me like a lady. I don’t want to be a woman full time. I have two identities and it would not work for me.

I like my life but I’m worried about what will happen when the kids are gone. I will have no one and nothing. What should I do?

ADVICE: The transvestite life is often hidden and misunderstood. You are not seeking to be a woman fully, but enjoy the thrill, adventure and alternative identity that this life offers. The desire for love, commitment and a relationship is the same as for any human being, but acceptance and understanding may be denied to you.

In your female role you enjoy the attention and attraction of men, and yet this does not sound like your sexual orientation. This might be confusing for other people, and perhaps also for your children should you decide to tell them.

You say you are still living with your ex-partner, and you are clearly a devoted father who has sacrificed your own desires for their sakes. However, expression of your true self is one that is difficult to deny, and the need to be fully accepted for who you are will continuously push to the surface.

Having a dual identity can offer wonderful stress relief when the pressures of life become overbearing, but there is also a cost factor. Most people want to have an intimate relationship with someone who is a coherent whole, and this is available to you only if you are willing to be completely yourself with your chosen partner. This means that any future partners will need to have a relationship with you in your male and female identities, which will require vulnerability and risk on your part and openness and love on theirs.

It sounds as though you and your childhood sweetheart still have some connection, and I am wondering if you think there might be a dormant possibility in this relationship. Have you both sat down and reviewed the relationship as parents and cohabiters, and as people getting older?

If you feel this is not a possibility, then your isolation and loneliness will require you to create a community of care that will support you into the future. Are there others who have the same experience as you who might be open to a stronger friendship connection?

It might be difficult for you to instigate more intimate and enduring relationships, as you say that you are enjoying your single lifestyle at the moment. The motivation to involve yourself in the time and commitment that an intimate relationship requires might not be strong enough, as the excitement of the dual identity and the thrill of new encounters are hard to give up.

If you want steady and close relationships in the future, you must take steps now. This will require engagement with and full pursuit of that aim; this will involve some restriction of the single and free lifestyle you currently enjoy.

You clearly have the capacity for this, as you have shown dedication and sacrifice for your children in the role of parent.

The decision is yours as to what kind of future you want to set up for yourself and who you want to share that future with.