Sunday 15 September 2019

Ask Brian: I've started cross-dressing after discovering my girlfriend cheated on me

Brian O'Reilly

Brian O'Reilly

Our no-nonsense agony uncle gets straight to the point of your most pressing issues.

Dear Brian,

I have been cross dressing for many years and it was more of a recreational bit of fun until a couple of years ago.

I stopped doing it for ages but when my long term relationship broke down due to my girlfriend being unfaithful I couldn't resist starting again ... I like dressing and acting feminine but recently have started going on to chat rooms and have been sexting lots of men and enjoy making them happy.

I really like the thought of them enjoying pics of me en femme ... I never thought of myself as gay but now I'm not sure if I am or if I may be transgender.

I am very shy around women and feel inadequate and this crossdressing and cyber sex is taking over my life. I am from a very conservative background so being gay or transgender will be a disaster for me ... I am struggling to find my true self but would appreciate your thoughts on what options are open to me.

Hoping you can help.

Brian replies:

Hi Anon,

Sexual orientation and gender identity are two separate and distinct issues, so try to separate them in your mind.

You can enjoy cross-dressing without being gay, or without being transgender. You can be a straight man and enjoy dressing in women's clothing for a variety of reasons.

From what you've described, it seems you enjoy the attention you get from men while cross-dressing - that doesn't necessarily translate that you're sexually attracted to them.

You say that you're quite a shy individual, so cross-dressing might be an outlet for you to feel more confident.

Only you know whether you derive any sexual satisfaction from it or feel any attraction to men, which of course might make you bisexual or gay.

There's also a big difference between enjoying dressing in women's clothes and actually feeling like you're a woman trapped in the wrong body.

From reading your Email, I get the feeling you treat this as your dirty little secret. Don't. There's nothing wrong with what you're doing, you're not harming anybody.

Do you actually feel sexual attraction towards to men you chat with? Or do you just derive satisfaction from their attention? Thinking about this will help you clear confusion you feel with your sexual orientation.

You say that you struggle with your confidence around women - is it possible that the attention you're getting from men while cross-dressing has filled a void? Do your confidence issues mean it's easier for you to dress up and enter the cyber world rather than go out in the real world as yourself?

One note of caution I would sound is that your experience thus far is very much confined to the cyber world; the real world is a very different place.

You should also explore the gender issues you have identified, but I think it might be worth talking to a qualified professional about it. It's quite a complicated issue and I'm not qualified to address it in any detail.

But I think once you are able to establish what you actually enjoy about the whole experience, it might shed light on the other issues you've raised.

What I can say is that everyone should live their truth and be happy in life.

I wouldn't worry too much about your family yet. You have a lot of thinking and discovery to do yourself before you start thinking about your family.  That's a long way down the road.

And if you choose never to tell them, that's fine and your choice also. It really isn't anyone else's business. Do what makes you happy.

Don't feel pressured to put labels on yourself, they're unnecessary.

TENI (Transgender Equality Network Ireland) is a fantastic resource and can offer you guidance and support.

There are details of support groups and numbers to call on their website, which you can visit by clicking here.


Do you have a problem you'd like some advice on? Email  to submit in confidence.

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