It all started with a casual ‘aside’ to a male friend of mine, with whom I am in a ‘friend without benefits’ sort of relationship. I knew he wasn’t gay but he was the sort of bloke a girl likes to take shopping for clothes on occasion, as he gives an honest appraisal of an outfit.

So I was telling him about a ‘clothes swap’ taking place in my square in South London, and how we drink copious amounts of wine and eat lots of food and then pile the wears on the floor and try on each other’s clothes in front of a long mirror. A really healthy enjoyable gathering of female friends, and coming home at the end of the day with new gear and a new lease of life. A ritualistic meeting in my book, and my friend agreed, and said how envious he was and wanted to be at the next one.

Without any probing he then went on to tell me that he enjoyed dressing in women’s clothes, but insisted it stopped there. I was fascinated as I had known him for some time, and he then went on to tell me that it is more popular than we imagine.

I was a little surprised, but my mind went back to a neighbour some twenty or so years ago who was married to a well known rock star, who frequently wore her clothes around the house. I am not going to spill the beans on who it was, but let me tell you she was not in the slightest bit fazed by his behaviour, and even encouraged it as they would end up having great sex and she said she would prefer it be with her than some willing groupie, who would no doubt agree to do anything he asked for.

Another experience I had was when I shared a flat with two males when studying Drama at Performing Arts School. One of the students would go out at night dressed from head to toe in women’s clothes plus makeup. It took a while for us to find it out, as initially he did it in secret, but my other flat mate discovered it first. Then Rob (cover name) got bolder and bolder, and ended up walking into the lounge fully clad one Sunday afternoon to say ‘Hello’ to both of us. By that time we both knew and treated it as if it were a completely normal occurrence, so our friend remained cool and continued to cross-dress and apparently still does.


I did actually see him on a TV show wearing women’s clothes some years later, so it had obviously become the norm for him by then.

I also enjoyed both Tootsie with Dustin Hoffman and also the late Robin Williams in Mrs Doubtfire – not particularly because of the cross dressing, but because it seemed so natural to both male actors who carried it off superbly. But as far back as the early fifties in ‘Some Like It Hot’ starring Marilyn Monroe, Jack Lemmon and Tony Curtis dress up in women’s clothes as as disguise to escape from their predicament.


Crossdressing has even been part of storylines in soap operas, who can forget Les & Pam’s story in Eastenders. Whilst Pam was shocked at first she learned to accept Les.

I am quite certain that the majority of us will have someone in our circle of male friends who either is a cross-dresser or knows someone who loves to wear women’s clothes.

I personally think it amazing that we have come so far and would encourage all of us to embrace it to the full.   By the way, my friend is coming to the next clothes swap.


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