I want to cross dress for a Halloween party, but I'm afraid to go alone | The Sun

DEAR DEIDRE: AFTER many years of cross-dressing in private, I want to go out as a woman in public, but I’m scared to do it alone.

So I’m thinking of hiring an escort to come with me to a Halloween party.

I can’t really afford to pay her, but being with her will make me feel more confident.

And, at 44, I know I’ll get a thrill out of dressing up in the clothes I feel comfortable in for the first time, instead of wearing boring men’s clothes.

The irony is, while everyone else will be wearing a costume, I’ll be more myself than usual. And nobody will realise.

Is this is a good idea?

Get in touch with the Dear Deidre team

Every problem gets a personal reply from one of our trained councillors.

Send an email to [email protected]

You can also send a private message on the DearDeidreOfficial Facebook page.

DEIDRE SAYS: It’s great that you’ve found an opportunity to dress up in a way that makes you feel happy in yourself.

But paying a sex worker is very expensive and won’t help you feel accepted. A trusted friend would be better.

My support pack on Cross-dressing will help you to think this through and link you to people who will understand.


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