Dating diary 16. I think this is the first time in my life I haven’t enjoyed sex. It is a disaster, at least for me
In his bedroom, he has a four foot tall teddy-bear on the bed. Odd for a man in his mid-fifties
November 20, 2015 | By:
Louisa, our 50-something columnist, is sleeping with two men, but she knows she has to choose one of them. So she stays over at her millionaire's to see how he performs
Dating. Sex in your 50s. Stocksy. 620x349

Louisa is left unsatisfied

I am dating two men, and have slept with both. But as I said in last week’s column, I don’t think men expect women to be checking them out in bed in parallel, so I must make a decision.

Wickedly, my plan is to check out Plane Man (the millionaire) in bed for the second time to see if things go uphill or downhill. Or get any bigger. And to decide within two weeks between him and the Delightful Dick.

And Plane Man did send me a huge bouquet after our first foray between the sheets, so I am equivocal between the two. And, frankly, jolly lucky.

I arrive at Plane Man’s house on a lovely, balmy, late-summer evening. First I am invited to drink champagne in a hammock in his garden where he reads me poetry. Then, having downloaded my favourite song and learnt to play it on the guitar, he sings it to me.

Then we go inside for him to cook me a really nice dinner. It’s a bit much but I have always liked a trier. Compensation behaviour? Maybe…


While he is preparing dinner, he suggests I sit on one of the bar stools. They aren’t comfy so I get up and wander about and pick at the salad ingredients. “No!” he says, irritated and very firmly, “I want you to sit on the stool. You can’t wander round the kitchen. Just sit there and stay put.”

I am, to say the least, taken aback. Nobody puts baby on a stool.

After dinner, I am instructed more than invited to come to the hot tub. Do I run out of the house? Or just see how we do later and accomplish the final DD vs PM assessment? Well, as a good time in bed can compensate for other deficiencies, I elect to go the distance.

Finally, we go upstairs to bed

After some canoodling and fondling in the tub, upstairs we go and, weirdly, he puts me in the spare room. Slightly odd, but actually I think might prefer my own space.

Then, in his bedroom, he has a four foot tall teddy-bear on the bed. Odd for a man in his mid-fifties, I remark. Poor Pooh is unceremoniously flung to the floor and dismissed as home decor. Now, cruelty to bears is a bit of a no-no in my book, but doggedly I decide to take this to the bitter end.

Louisa goes to an animal fancy dress party – and bumps into her ex (in a donkey costume)

Sex is, of course, a disaster, at least for me. He seems to be having quite a good time, as far as I can tell, until I am commanded to keep twisting his nipple if I want him to continue with the matter at hand.

Well, I do for a while and then, realising I am cutting my nose off to spite my face, I stop.

He then takes a little while to satisfy himself and, thankfully, it is then all over. I have spent most of the time wishing I wasn’t there. I think this is the first time in my life I haven’t enjoyed sex.

Good news! I have a bedroom of my own to go to so I decamp and lock the door. Well, this man is definitely not for me. I don’t care how many airborne vehicles he has. Nobody makes baby sit on the stool!

Easy, fast exit in the morning, as I have to go to work. But I am off the horns of my dilemma.

A weekend with Delightful Dick

Later that day, the Delightful Dick invites me for a weekend at his seaside home and I accept.

I cannot spend a weekend freely and joyfully with a man I like with another lover in the wings, but I keep putting off telling Plane Man. I decide to text and then call, so he can absorb first. Dumping a millionaire by text is one for the CV, I suppose.

Read more on dating in your 50s

I don’t like hurting feelings, so when it can wait no longer, as I am leaving for Somerset, I finally send the text. I truthfully tell him that he is the most impressive individual I have met for a while but that I don’t feel enough for him with my heart to continue. And that I will call him in half an hour.

He replies that he agrees there is something missing and then we have a very affable chat. We agree it has been fun and we will stay in touch. Somehow, I doubt it.

Dating second time around is somehow more calculating, more measured. You analyse what you want and don’t want and consider all aspects much more fully. I have decided to see where it goes with The Delightful Dick, a lovely man with a dodgy todger. That having been said, I feel relieved, excited and happy and inclined to trust that instinct above everything else.