Taboo confessions of men who date cougars: Boytoys tell JANA HOCKING why they’re really into older women

I have a friend who’s the madam of a very high-end brothel. I know – fabulous.

The other night, we were discussing who her highest-paid, most requested escort was. I had a few guesses. All wrong.

It was the oldest woman on her books. ‘By a long shot!’ she said. ‘All the younger men book her. I’m considering upping the age of my women. I need some older ladies to keep up with demand.’

It reminded me of a chat I had with Angela White, the world-famous porn star. We were sitting at Chateau Marmont in Los Angeles, hilariously watching men try to pretend they hadn’t recognized her while barely taking their eyes off of her.

I asked whether she ever worried she would ‘age out of the business.’

Her answer was blunt and to the point: ‘No! There’s a huge market for “Mommy” porn.’

Between Angela and my madam friend, I was beginning to wonder whether getting older might actually be good for my sex life.

Both had the same theory about the appeal: men love to be schooled between the sheets.

One of the kinkiest men I know credits an older woman with teaching him about sex. He was 18; she was a 42-year-old divorced friend of his mother’s.

Yes, this scenario is questionably icky.

But it left me wondering about the men chasing older women: do they fancy us, or are they looking to explore a kink and get an education?

The question popped into my head again this week when I devoured the pictures of Bunnie XO’s extreme PDA with her younger new man. She’s 46, and never looked hotter, and he’s 24 – and hot in a cowboy fantasy kind of way.

‘Play on!’ I thought to myself. Especially amid her divorce from Jelly Roll, she deserves a little fun.

While it’s perhaps great revenge for someone like Bunnie, I pondered about the other side. What exactly is going on in these men’s heads? So, I did what journalists do best and threw it out to my friends and followers.

One man, 29, had never dated an older woman until he met a 47-year-old through friends.

‘She was quite proper at dinner. Nice dress, asking about my job. Then we got back to her place and she opened this drawer beside the bed. I remember thinking, Jesus, there’s a lot in there.’

I asked what happened next.

‘She handed me the remote for one of the toys and told me to watch what her body did when I changed the setting. Then she took my hand, showed me exactly where she wanted it, and kept it there for about twenty minutes without saying a word. I’d spent my twenties trying to do more, and she had me doing very little for a very long time.’

Another man, 27, had changed the age settings on his dating apps before he matched with a 44-year-old divorcée. On their second date, she asked what he actually liked in bed.

‘I gave some vague answer because I was embarrassed. She waited, so eventually I told her I liked being bossed around a bit.’

I asked what ‘a bit’ turned out to mean.

‘She went straight into dom mode. She told me to take my shirt off and sit on my hands, and I wasn’t allowed to touch her until she said so. She tied my wrists with the belt from her dressing gown and then she took her time. I’ve never had to concentrate not to blow so hard in my life.’

A 31-year-old assumed his 50-year-old lover would be up for anything. It was one of the things that led him to explore the age-gap relationship.

‘I wanted to film us. I said it casually, like it was nothing. She looked at me and said, “I’ve been on the internet for twenty years, darling. I know exactly where that goes.” She said she’d happily try just about anything else, and she wasn’t kidding.’

The women I spoke to had their own reasons for seeking out much younger men, though the results were much more varied. A 46-year-old said her 28-year-old lover ogled her openly and enthusiastically, which was a novelty after her ex-husband.

Several weeks in, he called her a MILF.

‘I don’t even have children. We were lying in bed and he said he’d always wanted to be with one. I asked whether his friends knew about me, and he got a bit shifty. Suddenly I felt like I’d been discussed like a circus animal.’

So she asked him what he liked about her. He mentioned a joke she’d made at the dinner where they met, and the way she’d put her hand on his leg under the table.

‘That helped. He remembered the evening properly and in detail, but we never really recovered. No one wants to feel like a novelty act.’

A 45-year-old said she was delighted by her 27-year-old lover’s stamina and horrified by his technique.

‘He thought faster meant better. I had to say, very kindly, that I wasn’t trying to start a lawnmower. I put his hand where it needed to be and told him to match my breathing. He took it surprisingly well, and I often wonder if his next girlfriend benefited from my teachings.’

Of course, one older friend, who I might dare suggest is a little bitter about women of his age choosing to go younger, outright stated: ‘Do you really think this is a complex dynamic to analyze?’

He then gruffly suggested younger men find older women easier to get into bed ‘without as much effort or financial investment.’

Charming. Apparently, we become a budget option somewhere between our first grey hair and our second mortgage.

He also suggested women enjoy the attention until it stops making them feel good, adding that this ‘isn’t exactly one of those hard to explain phenomena.’

Is negging still a thing? Because that line felt awfully familiar.

Having read hundreds of replies, I think he might have benefited from asking a few questions himself. The majority of men who responded certainly had more to say about the appeal than how much they’d saved on dinner.

Still, the question of whether he fancies you or has an older-woman fantasy allows for an obvious possibility: both. I can live with being someone’s fantasy – and maybe skip my Botox appointment. I’d also just like him to take me to dinner after he’s caught his breath.

And if I’m expected to teach him everything I know, my madam friend has already established there’s a very healthy market rate.