by Rachel Stewart

Sometimes there are just no words. But I’ll give it go. Stay with me. This is all leading somewhere.

I’m of an era where men crossdressing as a woman used to be funny. By that I mean, in my youth, I’d sometimes find myself at parties where men would suddenly appear with a wig and dress and lippie on.

Even my father – a manly man – had no hesitation when he’d had a few about throwing a dress on and one of mum’s large bras stuffed with hay and mincing around the lounge at a family gathering – which we had a few of. He thought he was hilarious, and everybody laughed up a storm, and sometimes his mates would join in like it was a full-blown stag night.

In the 70s background soundtrack of my life, the wonderfully talented and very naughty Benny Hill was prancing about on tele not only chasing women but often playing them. It was a normal family event to watch his weekly show. And did we laugh. Here he is as Farah Fawcett-Major in the off the charts popular Charlie’s Angels.

In 2026, of course, he is considered a seriously sexist old creep, and reruns have been off the menu in the mainstream space for decades.

Then there’s the inimitable Les Dawson and Roy Barraclough (a.k.a. Coro Street’s Alec Gilroy) who together played ‘Cissie and Ada’. Here they are discussing menopause.

So why were these shows – and many more like them – wildly popular at the time? What’s funny about them?

Well, for me, I find something extremely amusing about men pretending to be women for comedic effect. These skits are overall witty, clever, and accessible. They know that we know that they’re taking the piss. They’re having fun and we’re having fun watching them having fun. Nobody is getting hurt and everyone’s having fun.

In other words, it’s more than okay to laugh at them. We all get the joke.

But here’s another clip. A deadly serious post that you are absolutely not allowed to laugh at. If I catch you letting loose with even one guffaw you will be in big trouble.

Some context. This next man suddenly decided to take his “whole self to work” a few days ago and turned up at his day job – as a lecturer at Oxford University no less – and straight-faced proceeded to go about his business wearing huge prosthetic breasts and a lacy red dress. His wispy beard and badly applied makeup would be funny if he wasn’t being deadly serious.

Here’s his work clip and, no, it’s not AI.

Frankly, it’s not his neck that’s sticking out. And, man, is he boring. I kept waiting for the punchline that never came.

Fellow Oxford professor Michael Biggs said there is ‘a strong case that Mr Rattley is creating a degrading and offensive environment, especially for female students, which would constitute sexual harassment’. ‘Adults should be free to explore their sexual interests in private with other consenting adults, but not to bring them to work’.

And that’s exactly what this new and growing weirdness is. A fetish. Mr Ridley is not trying to do anything other than enjoy his sexual fetish as a town milker, and test how far he can take that within his place of employment. He is, at least, not claiming to actually be a woman, but he is pushing boundaries in a space that should be all about professionalism and decency.

Of course, despite pressure, Oxford has so far done nothing about this overt display of male sexual dominance and kink. Because that’s what it is. Kink. But we are in an era where this man will display his kink proudly and expect zero pushback from the powers that be. And he’ll likely get away with it, even if his students are uncomfortable. Kink-shaming is out, don’t you know.

In other words, while he’s definitely no Benny Hill and is distinctly un-funny, you better not laugh at him or you’ll be a big, fat bigot.

But if you do inadvertently let out a sly chuckle in response to this weirdo, you might find a pair of prosthetic boobs squeezing you to death. And not in a good way.

Listen to the full episode of Riding Shotgun.