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Dress to impress Ask Maura: My male pal likes to try on my clothes and now I fancy him

"He asked if he could try on a dress that I own. We found one with a shape that fitted. Next thing he’s putting on false eyelashes and lipstick"

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Some men enjoy wearing women’s clothes.

Some men enjoy wearing women’s clothes.

Some men enjoy wearing women’s clothes.

Solve your life dilemmas with expert advice from Maura O’Neill

Dear Maura: A friend loves to come over to my house to try on clothes and do make-up. He’s 32. I’m not his only female friend but he feels comfortable with me.

It happened so naturally when he was at mine one night having a few drinks. He asked if he could try on a dress that I own. We found one with a shape that fitted. Next thing he’s putting on false eyelashes and lipstick.

I put it down to the beers but then he dropped over another evening and off he went, trying on clothes. Six months on and I’ve got very close to him.

I fancy him a bit but don’t know what’s going on with him sexually. There’s a lovely friendship between us mostly because I know his secret.

And that’s the thing, is he close to me because he can be himself when he’s with me or is he here because of the kind of person I am? Is he attracted to me? Or am I just a friend?

Answer: How lovely for your friend to be with someone who accepts him for exactly who he is. This is his first experience of expressing this side of him.

He’s most likely dressed up in his own place but the bond that has developed between you has allowed him to drop his guard completely. You have given him a safe place to release his female persona. There is something special going on here.

However, you need to encourage him to talk about everything. How long has he been dressing in women’s clothes? Are you the first and only person to know about this? Is there an unhappy, unfulfilled female inside?

This will give you an opportunity to understand him and to see if a relationship is possible. Anything is workable if both people fully commit. Always show respect.

Email your problems to

  • Dr Angela Brokmann dr.angela@sundayworld.com
  • Maura O’Neill maura.oneill@sundayworld.com

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