I want to try cross-dressing in public

I AM a reasonable-looking 50- plus-year- old man, divorced with three children. Two are midteens, the youngest is six.

My childhood was strange; not a lot of love around, but most certainly comfortable enough. I’m the middle one of three brothers. My mother always claimed she wanted a girl.

I suspect it was to compensate that she used to dress me in her lingerie (panties and nightie) and put make-up on me. I don’t suppose at the time I complained. Throughout my entire life I’ve had a fascination with women’s shoes and underwear, wearing them in secret.

I have always admired transgender and crossdressing people, but have never been attracted to men.

Now I have reached a stage where I want to pursue my dressing fantasy.

I adore dressing up, make-up and all the fun, freedoms and colours that go with it. I’ve also sometimes tried going out.

I have no idea if I want to make this change permanent. I certainly don’t want gender surgery, but I know I want to give it a real go for a couple of months maybe and see where it might lead.

I have given everything to my family and now I feel (rightly or wrongly) that before my appearance ages further, I would love to do this for ‘me’.

To cut to the chase — is this totally unacceptable, unreasonable or just downright selfish? It really is a now-or-never change. Am I being unfair to think I owe it to myself to try?

ADAM

AdAM, I know you have written ( which takes great courage) in search of affirmation from me. Yet I feel unable to give it — mainly because I have come thoroughly to dislike the modern mantra: ‘You can be anything you want to be.’

It’s trotted out all the time, and I suspect has done quite a lot of damage to young people, who take the dishonesty at face value.

Because very, very few of us get to be exactly what (and who) we want to be. We can daydream, of course. But problems can arise when we feel entitled to enact the fantasy, sometimes at a cost to others, but often also to ourselves.

I would love to know whether you are working and, if so, how you feel a decision to cross- dress in everyday life would be received by colleagues.

I would also like to know how you feel people respond to you when you go outside wearing women’s clothes, as you have recently tried, and (more importantly) how you feel your children might respond.

Those reading this who will say you are clearly transgender and should follow your dream will probably tell me that none of the above should matter.

But I think it does, since none of us lives our lives in isolation.

How would you feel if your children rejected you? Your feelings for them are of paramount importance. Would it be fair on them to live as a woman?

What kind of mother chooses to dress her little boy in her lingerie and puts make-up on his face? My only reply is — one with mental health problems.

Your uncut letter reveals you suspect your fascination for women’s clothing stems from her behaviour. Surely few people would argue with that.

I would love to know how your relationship with your mother developed as you grew older and whether now, looking back, you are grateful or resentful that she imposed her fantasy on you.

So many questions, but it’s vital to consider the implications of going 100 per cent public with your secret world. I’d counsel caution and compromise — that’s my usual approach to life.

To be absolutely honest, I’ve long had grave doubts about trans ideology and what it’s meant for young people.

It’s a big issue, too complex to unpick here. So I will make you a pledge. Once this is published I will forward to you all the responses I receive to your letter (unless I think they might be hurtful), so that you have as broad a range of views as possible to help you make up your mind about your future.