Ask Jane, Column 11

Sharing Secrets With Family


I want to be honest with my son and tell him I’m a cross-dresser. I have been honest with him all of his life except in this one area. I feel his not knowing creates a wall between us. I would tell his girlfriend as well. In addition to the honesty question is the logistical one. My son and his girlfriend live with me in my house and I’d rather they not find out accidentally, if you know what I mean.

I have been tormented by my cross-dressing in the past and have sought out therapy to find some peace of mind. But I’ve had little luck. My first therapist put me into a group therapy with druggies and alcoholics. My second attempt at therapy was with a psychiatrist who gave me Valium and other sedatives. The third was just nuts; we talked mostly about hunting dogs. The fourth, and last, was a religious guy who tried to make me quit doing it.

I was 3 or 4 years old when I first tried on my sister’s clothes. I am 51 now and enjoy cross-dressing and going out in public. I was married 10 years to a non-understanding female. I told her before marriage, but she thought she could bring me around … and I thought she might eventually become understanding. We’ve been divorced 14 years.

Many years ago I would steal women’s clothes. I would break into apartments and houses and even retail stores and steal every bit of lingerie they had, and even dresses and shoes that were my size. I knew this was wrong and resolved to do something about it. I gave myself permission to cross-dress but not to steal. This worked for me, and probably kept me out of jail. I haven’t stolen anything in 30 years.

At this point in my life I’m pretty well adjusted about cross-dressing and love to go out. I’m amazed by how much like a lady I’m treated when I’m out and want to do it more.

But …. how do I tell my son?

Thanks for listening, Jane.


Dear JL,

I respect your courage. Cross-dressing is so misunderstood that it’s easy to be reticent about telling others. Because of the lack of knowledge about it, your son’s and his girlfriend’s first reaction might be to ask whether you’re gay. If you communicate openly, as it appears you do, you’ll be able to work through all this and all the many other questions they may have. After your initial talk, be sure to let them know the door is open for them to ask more questions and air their concerns and feelings. You might also give them books to read such as My Husband Betty, one of the best for the way it addresses loved ones’ fears and concerns about a cross-dresser they love.

I hope you feel free enough with your son and his girlfriend to share the history of your childhood and even theft. These details provide a glimpse into the drive you’ve had to satisfy your need to cross-dress and I think they’ll feel sympathy toward your need to do so. They will likely also feel for you as their father and as a man on this earth who’s had to bear the burden of a secret all these years.

Leave it to them, please, about whether they want to meet your alter ego. They may not and you need to respect this and not take it as a slight. You are “dad” and they may not wish to know you in any other form … Leave it up to them, and don’t engineer a meeting -accidental or otherwise- between them and your femme self.

I suspect your son already knows more than you think he does. Or, if he doesn’t, he’ll look back upon his childhood and put things together that didn’t make sense then but do with this new information. It’s funny, though. Kids see it all and what they don’t see they sense.

I respect your courage, JL. I’m sorry you had such lousy therapists! I was aghast when I read of your experiences, each worse than the one before, it appears. There’s so little understanding of cross-dressing amongst professionals … but surely one would think a therapist would at least offer understanding and sympathy for another’s pain and suffering. But not one of your therapists approached you as a man in psychological and emotional pain. Aaarrgghh! I’m so sorry you had to deal with those folks.

Would you please write and let me know how your life is proceeding, JL? I very much care how this meeting goes …

Actually, two last thoughts, in addition to any members of URNA might have: First, remember that you cannot control another person’s reaction. You must be telling this to your son and his girlfriend because YOU need to tell them, not because you anticipate a particular reaction or fantasize a particular outcome.

Second, approach this topic with dignity and self-respect. Do not apologize or disparage yourself (“I’m sick in the head,” “I don’t know what’s wrong with me,” etc.). There is NOTHING WRONG with cross-dressing and nothing wrong with you because you do it. Be good to yourself and to JL … show respect and kindness toward both your selves and never apologize or make excuses. You are the way you are, period, and it’s the way you’re meant to be.

Good luck!


Photo of Jane and Eve (Adam To Eve) by Jamie Fenton.


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